The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick

What's the most common mistake that people make when they're negotiating their call? Often will hide behind the

their call? Often will hide behind the easiest communication channel possible.

I might email you my demands. The

problem with that is I can't control tone. If I push back and the CEO that

tone. If I push back and the CEO that reads it's in the airport security line and pissed off and they read it, they might be like, "That bastard wants more money."

money." >> A lot of people listening to this are just afraid to ask for more. I'm going

to come across as greedy. It's all going to fall apart.

>> But when you look at the money that the company's making in comparison, like you're not being greedy. doesn't have to be such an aggressive thing. It doesn't

have to be confrontational. The simplest

advice is what's the chance there could be a little more. That's not greedy at all.

>> The core to your philosophy is make it very clear to the company, here's the pain I will solve for you and here's why it's worth paying me this much more.

>> These companies have significant leverage over you. They know what people make. They know what others make. They

make. They know what others make. They

know what they'll accept. You have to understand what value you can create.

And if you understand that value, you can have that conversation with confidence.

Today my guest is Jacob Warwick. Jacob

is a professional negotiator. He works

behind the scenes with his clients, mostly senior tech execs, professional athletes, and Hollywood celebrities. And

he helps them navigate their most complex career negotiations, including their comp, their bonuses and investments, also M&A and takeovers and enterprise sales deals and more. He's

helped his clients secure over $1 billion in additional comp. and he's

told me that he's negotiated against a number of guests on this podcast. He is

very much under the radar, is not on social media, rarely does interviews, and in this exclusive conversation, we get super deep on the specific tactics and psychology of comp negotiation,

including why you should never negotiate over email, who should speak first when the question of comp comes up, the most common and costly mistakes that people unknowingly make when they're negotiating comp, and so much more.

Jacob is also just a truly stellar human and I'm very excited to be sharing his story. Don't forget to check out Lenny's

story. Don't forget to check out Lenny's productpass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. Let's get into

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Jacob, thank you so much for being here.

Welcome to the podcast.

>> I'm very happy to be here and uh thank you for interfering with my sleep all week out of my excitement. Usually, it's

my newborn and toddler, but this time I was waking up at 3:00 in the morning thinking about and it's going to be a great chat. So, I'm very excited. Thank

great chat. So, I'm very excited. Thank

you for having me.

>> I really appreciate that. Uh it's going to be worth it. It's going to be worth it mostly to us to to extract all this wisdom from your head. So, we're going to be going deep on negotiation, uh, how

to better negotiate for comp. And this

will translate into all kinds of other ways of in your life beyond comp. This

is something I've personally been very very bad at in my career. Uh, like I don't know if I like maybe one time I pushed back and negotiated uh a higher comp, but I just like have always been

really nervous to do this and just really bad at this. And I imagine most listeners are nervous and bad at this.

And you do this for a living. you help

people negotiate, which uh I don't think people even know this is a thing that exists that somebody's out there that can help you negotiate. And so you've seen a lot of negotiations up close.

Most of the people you work with, just as context, are very senior people, but a lot of the stuff we're going to talk about is going to apply to anyone at any level. Let me start with this question

level. Let me start with this question just to give people a frame of reference. How much comp are people

reference. How much comp are people generally leaving on the table when they don't even try to negotiate? Yeah. So,

typically what I've seen is even without my help, just general push backs, not aggressive, a simple what's the chance there could be more here kind of push back. I mean, that's about as easy as it

back. I mean, that's about as easy as it can get. You get the offer, you say,

can get. You get the offer, you say, what's the chance there's a little bit more. Almost always see a 20%

more. Almost always see a 20% improvement on that. And that is across the board from earlier stage positions.

Let's say they gave you a $100,000 offer. 120 could be there just from a

offer. 120 could be there just from a simple push back which is when you're making that kind of money that's life-changing right I've noticed that when you make a million dollar W2 same

push back 20% sometimes more just on the what's the chance depending on how well you kind of navigated that interview process now on average when I'm calculating out what I'm looking for

with clients is about 40% movement on an increase we have seen as much as 100 200 300 400% increases from initial offers

most notably breaking salary bands, which we all treat as gospel, which is something we'll probably talk about through the course of this this podcast today, that uh you know, those that

challenge authority and challenge in a meaningful and collaborative way will win more than those that don't. And

what's interesting is I found that product product leaders, engineers, designers, uh some of the more tend to be more introverted and

thoughtful types negotiate more poorly than the obnoxious marketers and revenue leaders and the more extroverted types.

And it's frustrating because if you look back at the last say 25 years or so, product has really defined the tech generation in so many ways. This isn't

to discredit marketers or or anything like that. It's just to show that

like that. It's just to show that there's a couple of sides of the business and and everyone tends to negotiate a little differently. So, you

looking back at your career and say, you know, the great Lenny had a tough time pushing back. I think that's that's

pushing back. I think that's that's actually inspiring for a lot of the listeners to see that you're not alone in feeling this. It doesn't have to be such an aggressive thing. It doesn't

have to be confrontational. The simplest

advice that I can give you is what's the chance there could be a little more.

That's not greedy at all. That's just a simple ask. And even that 20 30%. So

simple ask. And even that 20 30%. So

again, a lot of people listening to this are just like afraid to ask for more.

There's like uh I'm going to come across as greedy. Uh I'm going to it's all

as greedy. Uh I'm going to it's all going to fall apart. They're going to be like what are you what are you talking about? No, no, forget it. or they, you

about? No, no, forget it. or they, you know, they join, they get better comp, and then they're like, "Oh, everyone kind of, they know that I pushed all this, and I'm this kind of greedy person, and now the expectations are higher." What do you tell people to help

higher." What do you tell people to help them get past that and actually negotiate and actually go for it?

>> Yeah. A couple things here. So, first of all, usually a company is extracting much more value out of you naturally, like 5 to one, 10 to one, 100 to one, right? If you're I know the audience is

right? If you're I know the audience is primarily product here. I mean, you're developing products that have infinite scalability in some capacity that's going to make the company a lot of money

and you're a big piece of that and product tends to be rewarded fairly well, right? But when you look at the

well, right? But when you look at the money that the company's making in comparison, like you're not being greedy and if you understand that value exchange, you can have that conversation with confidence. That's not to say that

with confidence. That's not to say that being a tall puppy isn't risky. That's

the term. You overnegotiate.

I would rather my clients overnegotiate, reach a couple rungs up on the ladder and they get slapped down, they're still failing forward and they're growing in some capacity. And

some capacity. And if you can ideally align work that doesn't feel like work, it feels a little bit more like play with strong compensation. You don't always need to

compensation. You don't always need to negotiate hellaciously for the top of the band or break the bands just because you can, right? This isn't to be greedy, right? Right? But it's just to

right? Right? But it's just to understand that this value exchange isn't fair for you regardless of how it works. Like the path to wealth is

works. Like the path to wealth is through ownership, right? And as a W2 employee, you're being taxed heavily.

And it it makes sense to push a little bit in this context. So that's typically where I start. I want you to just have the confidence to know that it's okay.

Let me come at it from the other direction. Uh a lot of people listening

direction. Uh a lot of people listening to this podcast are founders or hiring managers, managers. They may not be

managers, managers. They may not be super excited to hear we're giving people advice on how to negotiate harder for higher comp. What could you say to them to make them feel a little bit

better about us sharing this sort of advice?

>> So I will challenge them as well. Now I

how important of a priority is top talent in maintaining and retaining top talent to you right when we're thinking about how quickly the speed of innovation is happening. You've had a

lot of great AI guests on the channel recently, right? Like the exponential

recently, right? Like the exponential curve of growth is increasing. If you

hope to stand a chance, you need to attract the top talent and you need to keep that top talent because it's very expensive to replace them. I'm not

suggesting that people beat you up for the sake of beating you up. So, this is a a myth about negotiation that's adversarial. What I teach is how can we

adversarial. What I teach is how can we be more collaborative? So the

conversation is look Lenny as a founder can you help me understand what's important to you the value that this work will drive and then naturally we'll come to terms that make a little bit

more of a value exchange make sense there. So often times some of the ways

there. So often times some of the ways that we're breaking the boundaries of compensation isn't necessarily advocating for a busted base comp level

and bonus percentage. oftentimes we're

putting performance incentives, milestone triggers. If the company grows

milestone triggers. If the company grows to 100 million ARR and I contributed this to it, what would that outcome look like? Would that be another trunch of

like? Would that be another trunch of stock or would that be cash or would that you know we are getting more creative here? And so what's interesting

creative here? And so what's interesting is for the longest time I had I had a difficult time advocating for this. And

having been a CEO and founder myself, I understand why you don't want to do it because it's hard. It's hard to make this. And everyone also thinks they're

this. And everyone also thinks they're top talent. And when everyone thinks

top talent. And when everyone thinks they're top talent, somebody's got to be lying, right? It can be difficult to

lying, right? It can be difficult to understand that. So those that I found

understand that. So those that I found are more confident to push towards performance-based tend to have more skin in the game, tend to want to stick around and see that success happen. Those are the types of

success happen. Those are the types of people I want working for me if I want to be a very competitive organization. I

have started to have these conversations with a couple of Fortune 500 companies as well as some talent consulting companies, think big recruiting firms,

where they've brought me in to advise on the comp committees so that they can get more creative with their structure so they don't lose talent. Because nobody

wins when you hire a top performer and they leave in 10 months. The recruiting

firm loses their pay, right? Their

performance pay. the company now has to go back and replace that person. It's

usually cost hundreds of thousands and in some of the realms that we navigate in the Fortune 500, it will cost millions if not tens of millions to replace the lost IP there. So the

argument here is it's okay to get creative, reward it when you see it, right? I'm not suggesting give everyone

right? I'm not suggesting give everyone everything in the company and and totally ruin your business model, but if you want to be competitive, be competitive with your pay as well.

That's a great answer. And we were chatting before we started recording this and you shared that you've helped people negotiate with many of the guests on this podcast like people that they were hiring and you helped them get

higher comp. I won't mention any names.

higher comp. I won't mention any names.

Um some recently were in in the realm of 10 million plus on increases in compensation across a team of just a handful of folks. Uh again, Fortune 500.

Um, but the alternative was lose them to competitors and have the stock drop after the CEO made announcements publicly in their earnings calls. And so

they don't know that it may have cost them 10 million today, but it saved them 300 plus 300 500 in this business process. So the success

will be there and I would say almost anybody would pay 10 to save 300. And

the way you operate uh just so people understand is you're very behind the scenes. you work with clients and you

scenes. you work with clients and you advise them. You're never involved in

advise them. You're never involved in the negotiation. You just give them

the negotiation. You just give them advice on how to approach it.

>> I would call it fingerprintless and there's a reason for this. So, it's it's not yet popularized. Maybe it will be with some of these uh and AI IC's and

these hot scientists are pulling down hundred million dollar contracts. Maybe

this will change soon. In Hollywood, you have an agent negotiate on your behalf and they kind of are serving as that middle mediator. That's not common in

middle mediator. That's not common in the corporate corporate America right now. Right now, if that happens, it

now. Right now, if that happens, it almost dilutes the leadership and presence of the executive. And so, how I work is similar to an attorney where all

correspondence goes through me before it goes to the end recipient. So, let's say that you're going to talk to the CEO, you call me first. We prepare the game

plan. We strategize. You then perform.

plan. We strategize. You then perform.

Then we debrief. Then the CEO sends you an email. That email comes to me. We

an email. That email comes to me. We

draft it together. I usually test my clients instincts first rather than just doing the work for them. Test their

instincts. Polish the language because every step of the way is a negotiation.

Now, this also slows the process down.

We want to go slower. And I'm sure we'll talk a little bit more about that in the podcast, too. Haste equals risk. So as

podcast, too. Haste equals risk. So as

you slow down, often times we want to take a couple of days to respond. Not to

be a jerk or belligerent or to manufacture some fake urgency, but it shows a little scarcity and thought process to your time. And we get to calculate and collect information through the process. This is so

interesting. What What's the most common

interesting. What What's the most common biggest mistake that people make when they're negotiating their call?

>> They don't understand when it starts.

So, the it starts much sooner than you think. So, I've I've got myself in hot

think. So, I've I've got myself in hot water with this before, too, because a like a LinkedIn profile on your resume is a snapshot of what you've been in the past, but it doesn't help you negotiate

in the forward, right? So, if somebody can say, "Oh, I'm looking at Lenny and I'm looking at product manager." If

that's all they saw, they're not going to know all this work that you're doing in the future moving forward and what your visions, things like that. So they

stamp you as product manager Lenny, right? Now you're media, mogul, icon,

right? Now you're media, mogul, icon, whatever. Right? But there's a gap to

whatever. Right? But there's a gap to have to fill, right? So the things you say on LinkedIn serve as a perception.

The headsh shot that you have serves as a perception. I used to joke that I

a perception. I used to joke that I could scan profiles, I would know how much money someone made by the quality of their headsh shot. And you can see and it would like it was wildly

consistent. It was almost frustrating.

consistent. It was almost frustrating.

But anyway, what you're putting out into the world, the narrative you share publicly starts to become how you're known, your reputation. If you're

positioned as a commodity, you will be treated like a commodity, right? So often times, the less you share is better because when you're on the phone with somebody, you

can correct the narrative and steer the conversation where you want it to go versus have to live by the sins of what you did 10 years ago, as an example. So

the things you share with recruiters, they take notes. When a recruiter calls you and says, "Hey, Lenny, how much money do you expect to make?" And you say, "Oh, you know, 225, that sounds fair." You know, 5 years later, they

fair." You know, 5 years later, they call you and they expect you to make 225 again. Not recognizing that you've grown

again. Not recognizing that you've grown exponentially since then. So everything

you communicate starts to serve as that value chain across the board. Another

mistake that people make, and you mentioned this a little earlier, it feels uncomfortable to get quote unquote confrontational or to feel like you're asking for too much.

So often we'll hide behind the easiest communication channel as possible. So I

might email you my demands demands, right? Or my negotiation.

right? Or my negotiation.

And the problem with that is I can't control tone. I can't control,

control tone. I can't control, especially when you're negotiating at high levels. If I push back

high levels. If I push back and the CEO that reads it's in the airport security line and pissed off and they read it, they might be like, "That bastard wants more money." That's all

they take away. Even if you perfectly worded it, you got it all, you know, as clean as it can be. If you catch them at the wrong time, you have no control over how it's received, right? So, it's

always better to have at least a video call, if not in person, so you can share tone, you can read body language, you can correct every step of the way. Often times, we

also try to negotiate through recruiters, right? You could do that. I

recruiters, right? You could do that. I

Jake, I did the thing, Jacob. I talked

to a recruiter. I spent a half an hour explaining it. The problem with that is

explaining it. The problem with that is you're playing a game of telephone. So,

the same thing happens. I I explain it to the recruiter. I get the tone right.

The recruiter goes to the CEO and says, "That bastard wants more money." And

that's all they communicate. Right? So

people negotiate with the wrong folks.

You have to go to the one who has skin in the game. Who controls the P&L? Who

controls Ebida? What what's what's their motivation? That's who you want to talk

motivation? That's who you want to talk to. And so some people might also have a

to. And so some people might also have a concern with, well, how do I go around the recruiter? I don't want them to look

the recruiter? I don't want them to look bad. We have to do that respectfully.

bad. We have to do that respectfully.

And now we need to plan what that communication looks like. And so the important thing here is just because it's uncomfortable doesn't mean you don't need to do it. It just means you don't know how to do it. So when

something's uncomfortable, you have to run towards that because that's where the growth happens. I love how tactical we're getting here. So following this thread, so the advice here is when you

get an offer and you want and you should basically you're saying you should always negotiate in some way. You should

push back. Your advice here is don't do it over email. Make sure you find a way to do a video call with essentially the hiring manager or the person that is has skin in the game, the like the finances

and the budget. There are situations, especially at high levels, more deals are closed on the golf course than they are in a boardroom, right? So, there are situations where you pull someone into a different element. This is called

different element. This is called homefield advantage, right? So if you go to a company to have a conversation, you're out of your element in in a

situation where you may not perform your best. The other thing people don't do is

best. The other thing people don't do is they don't control the time of which they have a conversation. CEO wants to hop on at 6:00 in the morning. Get your

ass up, get that presentation, and go.

You need to say, "I'm not available at that time. I'm and you read your own

that time. I'm and you read your own body language. I'm strongest between the

body language. I'm strongest between the hours of 10:00 a.m. and and 1:00 p.m. I

want a meeting in that time." So I will say I'm unavailable until that time becomes available. That also

becomes available. That also communicates scarcity and that you won't get pushed around. Right? So it's scary to do that to say no to the CEO. I'm

actually only available here. But that

also creates a rubber band effect that makes you more attractive. Right? And so

oftent times and actually OpenAI did this which is funny and I didn't realize what the reason was but I had some clients interviewing for seuite roles at OpenAI and so pushing Sam Alman around a

little bit which I'm okay with. I'm okay

with that. Um but so they used to walk outside of the office and just walk downtown San Francisco instead. Right.

You take someone out of the element. You

get the endorphins going. You're walking

and talking. You're the important piece here is instead of you and I being confrontational like negotiating between each other, we're walking walking side by side. So it's almost like you could

by side. So it's almost like you could put your arm around the other person, you're solving the problem together.

These sound like minor things to consider, but the body language and the tone and the collaboration and the energy starts to flow more naturally when you do this is

all behavioral psychology, right? And so

what funny story why I found out OpenAI did that was because they didn't want any executives going into the office because it was such a mess. It was like the biggest startup you've ever seen. So

I used to joke that it was two midgets in a trench coat pretending to be a real company, right? And uh so anyway, the

company, right? And uh so anyway, the point was let's take them to a place where we can control and have an advantage over the conversation. So

that's a way that you can think about where are you going to feel most comfortable? What hours of the day are

comfortable? What hours of the day are you most comfortable? If you can bring someone to a lunch or a coffee where you're on even playing field or even your home field, you will perform better

in those situations and you have more control over that than you may think.

>> So the advice there is try to get this conversation out of their office.

>> It can be, you know, but if I'm a product manager and I'm talking to a director, that may not be possible.

>> Right.

>> Right. It might just say, look, you got to come into the office, you got to do this. Right. I'm pushing like when I'm

this. Right. I'm pushing like when I'm talking about a seauite level like you could pull them out of the office. Hey,

let's go get drinks.

>> Like sometimes these deals are closed at 8:30 at night after a concert or something like that. So, it's easing that situation. That being said, it

that situation. That being said, it doesn't mean you couldn't try. It's

like, hey, I've got a couple questions.

Are you open to, you know, take a walk down AT&T Park and and have a conversation about it? If you can pull them out of that, you can start to build a stronger relationship through that and you're more likely to get your way. talk

us through this the kind of this the process you would recommend from I get an offer recruiter sends me here's your offer 300k salary some kind of equity

what's kind of like the step by step you and I know this is depends on the role seniority type of company PE VC back startup because it's very scary to push

back and be like oh I want more uh what's like that first email slrely to that email look like typically like what are some phrases maybe you'd use and then what's the how do you open up a

conversation where you plan to ask for more if you're meeting in person especially because that feels so scary.

So, first we want to approach with gratitude, right? We're thankful that we

gratitude, right? We're thankful that we want to move forward, right? So, Lenny,

I appreciate you making me an offer, right? I'm excited to work with you. We

right? I'm excited to work with you. We

want to show enthusiasm, which also shows some confidence. We have to show that the deal is going to get done, even if you're on the fence about it. Right

now, it's not to say you're so excited that it's a sure thing, and you're not showing that you're disappointed, even if you are. Right? So, I'm grateful. I'm

looking forward to working with you. I

want to review this over the next couple of days, right? I'll talk to my wife about it, you know, talk to an adviser, so and so. Later on, when you're a high level executive, you're talking to legal, you're talking to adviserss,

you're talking to a coach, like you may have five or six people see that, right?

Employment lawyer, all that. That stuff

is expected, right? So, you're going through the process. I'm going to take a couple days to process this. I'll get

back to you. I may have a couple of questions, right? But we'll loop back

questions, right? But we'll loop back and it shouldn't be a problem. I imagine

we start working together in a couple weeks, right? So the point is you have

weeks, right? So the point is you have to sell that the deal is going to be done which helps them feel like it's going to move forward regardless

right so any ask that you make is not going to be egregious now often times the higher you anchor the better you're going to perform which can be frustrating because you don't necessarily want to be like oh I

increased it 40% or anything like that now this is where a lot of nuance comes in so we might say you know come back 3 days later I want to have the conversation. Let's take a walk in the

conversation. Let's take a walk in the park and talk through it. Right? You

know, I got to be honest with you where this offer stands right now. I don't

feel comfortable moving forward. It's a

little lighter than I expected. Right? I

may start saying something like that and then just wait and see what they have to say. Maybe they say, "Well, what did you

say. Maybe they say, "Well, what did you have in mind?" It's like, "Well, what's the chance you can share what the range looks like for this and what type of performance did you expect for each of

these levels?" Right? Or they may say,

these levels?" Right? Or they may say, "We we comped you in the middle part of the range, right?" You might say, "What does the top end look like? You know,

what what must I do to fit those needs for you? Can you help me understand?"

for you? Can you help me understand?"

Now, for a lot of folks, especially in this market, and if we talk about what it was like in 2021 versus what it's like now, there's some overleveling that's happened. So, there are people

that's happened. So, there are people that are seuite going back to VP and VPs going back to directors, especially as they go to bigger companies. oftentimes

I'll say, you know, as we had this conversation, I'm I'm likely a little more horsepower than you anticipated, right? What's the chance we can come in

right? What's the chance we can come in and restructure the comp for the type of talent we're bringing in here, right?

And so, this is a line that we used uh there was three folks last year that were in ranges of 185 to 285. That deal

landed at 1.1 million when we were done with increases in stock, big cash increases. Two deals that were comped at

increases. Two deals that were comped at 600 that landed at 1.1 and 1.2. So

doubled from that. And these were situations where the role started at senior director and were upleled to VP because they were reaching for top talent in that situation. So there are

opportunities where it's easier to steer if you're really really good. Right? I

can see why some listeners are like, well, I'm not there in my career yet. In

that case, this is just how it gets done, right? This is how bigger moves

done, right? This is how bigger moves happen. It doesn't mean you can't push

happen. It doesn't mean you can't push for maybe 20% more. Naturally, that I would start with what's the chance there's a little bit more here. I was

expecting this, right? Again, more

nuances because if you open up what you're looking for too early in the conversation, that can be difficult to come back from later on. It's not entirely egregious,

later on. It's not entirely egregious, but one of the first things out of a recruiter's mouth is how much money do you want to make? Which is eerily similar to an illegal question, which is

how much money do you make, right? But

if you say what do you want to make, then it's okay. And that's where a lot of people get hung up as well.

>> I love that phrase you just shared of what's what's the chance there's a bit more here. I was expecting number X. Is

more here. I was expecting number X. Is

that is that the phrase you recommend?

That approach of just a soft push back just to see. Uh sometimes uh again it really depends on the leveling. If you

are very senior I I typically don't want to reanchor with a number because you should ever be so sure of what you're worth that you wouldn't accept more.

>> Right? And when you anchor that's the ceiling. And what often happens is

ceiling. And what often happens is naturally they want to split the difference. And so I'll have a quick

difference. And so I'll have a quick there's a quick Hollywood story here.

So, we had a writer who had a $700,000 contract, right? So, 700. And the agent

contract, right? So, 700. And the agent that I was working with was was saying like, "This uh this writer has the most aggressive attorneys in LA, right?

They're super aggressive." Uh, and I said, "Well, how do you know?" First of all, if that's what they're perceived as. So, the production studio offers

as. So, the production studio offers this writer 700. The attorneys come back and say, "We want 1.3, right? 1.3 million." And the studio

right? 1.3 million." And the studio said, "Fine, we'll do a million." And

they settled at a million. And I find that really interesting because the studio came up 300,000 and the attorneys lost 300,000. So they

split the difference right in the middle. So if the attorneys said 1.5,

middle. So if the attorneys said 1.5, would the deal have come in at 1.1? If

the attorney said 1.7, would it have come in at 1.2? Right. How do we know?

The way I see it is those attorneys weren't aggressive enough. We didn't

find the ceiling there, did we? Like

that was lazy negotiating, right? So, it

still made the client 300,000. They were

excited, right? The attorneys were excited. They made more on their

excited. They made more on their commission. The agency was excited. They

commission. The agency was excited. They

got 10% of that, but we didn't find the ceiling, did we? That was lazy negotiating. Right? So, those are things

negotiating. Right? So, those are things that you got to slow down to really understand where is the value being made here. in that movie. Like that movie

here. in that movie. Like that movie could make $50 million. You think a1 million for writing was worth it for someone who controlled the creative there? I don't know. A 50 to1 value

there? I don't know. A 50 to1 value exchange. Why not push for more? Why not

exchange. Why not push for more? Why not

put some milestones in that if this movie makes more than 50, my milestone is increased? This is how like Tom Brady

is increased? This is how like Tom Brady had his contract at Tampa Bay, right?

Win eight games, get a half a million dollars. Win 12 games, get a million,

dollars. Win 12 games, get a million, five. Go to the playoffs, get an extra

five. Go to the playoffs, get an extra this. Win the division, get this uh get

this. Win the division, get this uh get this, get to the Super Bowl X, win Super Bowl MVP, two and a half million more.

Like, so performance-based triggers.

>> I love just how how much you love this.

It's just clear this is so interesting.

>> So, it's really nerdy. I know. Like I I like obsess over it in a in a weird way, but uh I don't know. It's uh it's been kind of baked into my my psyche for a long time. probably because I I felt so

long time. probably because I I felt so powerless growing up that I'm so interested in how how power works and I was so scared to advocate for myself and I was the least assertive person that

you knew until I met my wife and she taught me how to be assertive and now I'm like off to the races. So that's

been helpful.

>> Uh on that note, uh do these tactics work on on kids and wives? Is this

something that translates?

>> Absolutely not. I would not recommend that. Especially if your wife knows what

that. Especially if your wife knows what you do for a living and hears you on the phone all the time and you try to say, "What's the chance?" And she's like, "No chance. What's Don't Don't pull that on

chance. What's Don't Don't pull that on me. I know what you're doing." Right.

me. I know what you're doing." Right.

And toddlers are terrorists. So, I don't I haven't figured that one out. I I

resort to bribes. And maybe that is a little Mavavelian on the on the toddlers. You can be you can be out of

toddlers. You can be you can be out of your mind working on that. But yeah,

don't recommend it with your spouse.

>> I would pay a lot of money for a version of you for toddlers. Oh my god. It's

like I try to show the other kid. I'm

like I'm like >> three minutes. He's like six. I'm like

four minutes. No, six. He never budges.

He's always >> five minutes. He's like eight.

>> Although sometimes my son does that, too.

>> Yeah.

>> I I go, "Do you do you want a binky?"

And he goes, "Five binkies."

>> I go, "I don't know if we have five."

And he's all 10 binkies. Like, "Whatever

you need, I'll get it if you go to sleep."

sleep." >> Yeah. Yeah. Please sleep.

>> Yeah. Yeah. Please sleep.

>> Yeah. Yeah, we need we need this for toddlers. I would I would I would

toddlers. I would I would I would subscribe.

>> Miss Rachel's the closest thing we got.

>> Yeah. Okay. So, coming back to this conversation number. So, you've touched

conversation number. So, you've touched on this a bit and I think this is an important part of your advice is when the number question comes up, who should speak first? What should your approach

speak first? What should your approach be if they ask you this question of how much do you want to make?

>> Yeah, there's there's a decent amount of nuance in this too. So, one thing you should realize is that especially earlier in your career, they're going to push on this harder.

And that indicates that the person asking is really more looking for a a commoditized or a price sensitive hire, right? That can be okay, right? There's

right? That can be okay, right? There's

nothing wrong with with sharing your number and getting a deal that that moves the needle early in your career and even middle of your career. That

changes the higher up the ladder you go.

And this is one of the reasons I want to share this is that what got you here won't get you there, right? So things

start changing as you mature in your career. And so when you're working with a top recruiter, they don't ask you about they won't. The

problem is top recruiters only reach out to you when you're very well known and they don't reach out to you very often.

It's like you it's very difficult to optimize for inbound attention the higher up you go unless you become very popular, right? And then what happens is

popular, right? And then what happens is you share less information because people come to you in a different capacity. Right? So nine times out of 10

capacity. Right? So nine times out of 10 a recruiter reaching out to you is going to ask that number. Right?

One time out of 10 they're going to just focus on the value creation. Those are

the ones you want to focus on the best possible. But it could be confusing

possible. But it could be confusing because so often you get a different side of the story, more of the commodity type stuff. So, typically I'd recommend

type stuff. So, typically I'd recommend you answer, right? I don't talk about compensation until we're ready to make an offer. It sounds like we're pretty

an offer. It sounds like we're pretty far away there. I'd love the opportunity to learn more about the team, understand where the value comes in and proceed kind of down that path to make sure

we're a good fit. Is that going to be a problem?

And then typically, they'll say, "Yeah, it is going to be a problem. I just need to know a number right now." I mean, this is what it's very uncomfortable to do this back and forth and to say no.

Especially Americans have a hard time saying no. I have noticed that other

saying no. I have noticed that other cultures can be more direct and just say, "No, I'm not going to do it." Like,

so be it. Right? So, culturally, there's a lot of differences in how this conversation happens. And so, they say,

conversation happens. And so, they say, "Look, we we need a number from you."

You might say, "Look, I'm uncomfortable doing that right now because I don't understand the scope of the role. Can

you help me understand what you had in mind?"

mind?" Right? The reason I learned this is I

Right? The reason I learned this is I used to be a marketing manager making $12 an hour in downtown San Francisco for series 8 companies, not knowing that $12 an hour wasn't a lot of money. I

just didn't know any better. But then I looked up marketing managers and I saw that they made 60 grand a year and I was suddenly got offended at how little money I was making. Right? Then I got promoted to director in that period and

was making $14 an hour. Good for me, right? And then I saw that marketing

right? And then I saw that marketing directors were making $ 110,000 at the time. So when a recruiter called me, I

time. So when a recruiter called me, I pulled that. I didn't want to tell them

pulled that. I didn't want to tell them I was making $14 an hour. They'd be

like, "Who is this kid? He's not very good. That's fake title." And instead, I

good. That's fake title." And instead, I said, "What did you have in mind?" And

they said, "Oh, we're looking at $110 to $130." And I'd say, "Oh, I'm on the

$130." And I'd say, "Oh, I'm on the upper end of that now." And so I went from $14 an hour to $120,000 a year in a single a single jump just like that.

That changed my life. One negotiation.

One of the reasons I'm so passionate about that. I hated the marketing work

about that. I hated the marketing work for what it's worth. But I thought like if I made a lot of money, it would make that pain go away of not liking my job.

Turns out that was a fool's errand. But

that's a story for another time.

>> Do things in your experience ever fall apart when you try to do that because that is a scary thing to push back on.

Just like no, I'm not going to tell you number. And you're giving us advice on

number. And you're giving us advice on how to say it in a nice way and then just like what did you have in mind? The

fear is like okay, they're going to hate me and they're going to be like this not worth it. We're going to move on. Has

worth it. We're going to move on. Has

that ever happened? What are the odds that might happen? A couple things about power, right? So, if you have the

power, right? So, if you have the ability to say no, you have infinite power right?

The nuance changes when when you don't have a job and you need to pay your mortgage, you might answer that differently because you want something, right? Now, this isn't to shame somebody

right? Now, this isn't to shame somebody who's feeling that way, right? If you're

out of work for six weeks in San Francisco, you're homeless, right?

That's just the reality of the situation. So, if I got to say a number

situation. So, if I got to say a number to get a job, I think that's fine, right? But understand that once you're

right? But understand that once you're employed and somebody's asking you and your needs are already getting met, why do you need to get pushed around? Right?

This is one reason that it's easier to find a job when you have a job. Now, I

think this is a myth for what it's worth, but this is easier because naturally your needs are getting met financially to a degree. So, naturally,

you negotiate more confidently. When

you're out of work and you have the uncomfort of being out of work six months, 12 months, 18 months, you have an identity tied to a chief product officer role or a VP of product. Like

that's your identity in our country. We

don't ask who you are and about your kids. We say, "What do you do for a

kids. We say, "What do you do for a living?" And when you're stripped of

living?" And when you're stripped of that title, it's uncomfortable. And we

want that pain to end. And so we give into these demands because it's an authoritative figure and we want that pain to go away. If we have the finances and the luxury of being able to say no,

we increase our power. If we have the ability to push back and practice these difficult conversations, you will increase your power and you'll you'll land at a higher rate because of it. So,

can it get frustrating? Absolutely. But

if somebody disrespects you through that process, doesn't that give you an indication of who the company's working with? Right now, again, I might accept

with? Right now, again, I might accept that because I need the money. I

understand. Right? But it's very telling how somebody's going to treat you depending on very simple push backs. And

one behavioral psychology hack here is we give someone a a positive reputation that they want to withhold whether they deserve it or not. So in this instance,

you'd say the recruiter, I want to thank you for being an advocate for me and for respecting that I won't share compensation figures right now. I

appreciate that.

And then they are trapped. They have to say, "No, I don't respect you. I have to do this." Or they have to say, "You're

do this." Or they have to say, "You're right. Like, that makes sense. Let me

right. Like, that makes sense. Let me

move you forward or not." Right? Another

option, you don't necessarily know if you're the best solution for that fit or not. And

so, we're obviously very ingrained when a recruiter reaches out to you and they say, "Look, we're going to pay 120." And

you make 150. And you're like, "Oh, I'm not interested. That's not even close."

not interested. That's not even close."

I would recommend continuing that process anyway to see as practice what you can negotiate, you can always say no later, right? Just because having that

later, right? Just because having that practice is going to make you hundreds of thousands if not millions more in your career.

Alternatively, if you feel bad about, oh, I wasted their time because I was too much for what they needed. Make

recommendations for them. So when the offer comes in in usage that gave us a senior PM role and what you realized is the JD and all of the work that you did is actually a director role but they're

not going to pay for a director role.

Right? How often does that happen? You

get to say look you know this role isn't in alignment with where we're headed.

Right? Would you like me to make an introduction to somebody that's a better fit? So you still get to help them. You

fit? So you still get to help them. You

remove yourself and then sometimes they say no actually we do want the role to be more senior. we're going to extend for you.

Like my first VP role came out of turning down a content manager position for 70,000 and 6 months later I landed a VP for a quarter million. Like that was

my my first realm into VP. The initial

offer was for content management. So

they came three four levels up the food chain. It was a long negotiation but

chain. It was a long negotiation but these things can happen if you don't say no too quickly. So along these lines I want to touch on it feels like maybe the core uh approach you take kind of the

core tier philosophy which is to kind of break out of this idea of some benchmark for a specific role and instead make it very clear to the company here's the pain I will solve for you that is really

important to you and here's why it's worth paying me this much more because it's such a big problem for you. Talk

about just that mindset. So, this really comes down to having curiosity and showing curiosity about the actual problem because usually if I'm speaking to a room of 400 people, right, which I

I'll occasionally do with some communities, I'll ask them who is actually doing the job that's on their job description.

Nobody will raise their hand. It's not

like you have your job description right there and that's what you do. Right?

There's always so much more that's not documented. Right? Now, when you're

documented. Right? Now, when you're going into a position, you see a JD, you're like, "Yeah, I could do all those things, but there's so much more, right?

This is another reason that anchoring to a number too early is tough because you anchor to, oh, this is this is fair for a senior PM role, right?

This is fair." Then you go through the process of the interviewing, it's very clear that it's a director role. You're

going to lead five people. They scoop

another team under you. Oh, we're going to put a productled growth motion under you, too. There's an whole engineering

you, too. There's an whole engineering pod and there's this and there's this.

All of a sudden, that's called scope creep, right? So, they scope creep the

creep, right? So, they scope creep the role. They talk about how they want a

role. They talk about how they want a senior hire. They're excited about you.

senior hire. They're excited about you.

They get you excited about it. And then

then they give you the offer and it's actually 20% under the number you originally shared.

And then you say, "Okay, well, this looks like a director role. I want X."

And they say, "But you said you only wanted 140." Now, they're using a number

wanted 140." Now, they're using a number against you and it's very awkward to come back from. And so, that's why we don't want to anchor too early. We want

to understand. And so this is one thing I wish especially product engineers, designers, that side of the the the product stack. I would love for you to

product stack. I would love for you to treat more of these like a sales conversation, right? You are an enterprise solution, a

right? You are an enterprise solution, a consulting solution that is several hundred,000 if not millions of dollars a year. If you were to sell that product

year. If you were to sell that product into an organization, think enterprise B2B deals. And I know I'm getting a

B2B deals. And I know I'm getting a little buzzwordy here. an enterprise B2B deal to Salesforce and you're going to sell a million half dollar product. It

would take you 18 months to develop the relationships and close that deal. You

have to develop champions in the organization. You have to understand

organization. You have to understand what value you can create for each of those people so that they can advocate for you. You don't come in and pitch

for you. You don't come in and pitch them the price right off the bat. You

need to understand the value. So through

the process, it's a discovery process.

Why am I here?

What gets you excited about me? Right?

That's how we start a conversation. Too

many interviews start with, you know, tell me about yourself, tell me about the stuff in the past. If you're talking about your past, you're on the back foot and you're losing that conversation.

You're the one revealing information.

You're not getting anything. We instead

want to have a conversation and say, "Look, some of the best interviews I've always had felt a little bit more like consultations or brainstorming sessions.

Are you open to having a chat like that today?"

today?" That's the first step. Typically, they

say, "Yeah, that sounds way better than me trying to drill you with questions."

So, let me ask you like, "What are some of the things that you're excited about?" I imagine, Lenny, you're excited

about?" I imagine, Lenny, you're excited to talk to me because I can help some of your audience negotiate. You've seen

proof where dozens of your subscribers have made more money with the article we wrote together. You've even seen that

wrote together. You've even seen that some of your guests unknowingly have been negotiated against with some of the work that I've done. Is there anything that I missed? What's exciting to you?

So, I want to clarify why I'm in the room with you. Right. So, we do that as a PMO. It sounds like now we move to

a PMO. It sounds like now we move to labeling. It sounds like you have a

labeling. It sounds like you have a challenge with this product line. It

sounds like we need to move or ship product faster. It sounds like AI has

product faster. It sounds like AI has been a problem and we need to shift towards native AI. Is there anything that I missed? Right? Then they're

revealing information. you take control of that conversation and then we want to share what have you done about it like how big of a problem is this in the organization. This is basically a SWAT

organization. This is basically a SWAT analysis like what are some of the things you've done well? What are some of the areas that the team failed? What

are some of the things we should be doing that we're not? And what are some of the things we absolutely shouldn't touch? So I want to add I want to ask

touch? So I want to add I want to ask all these discovery questions. They're

like, "Oh, look. It's a it's a $10 million problem, or we've we've gone through five different PMs in six months, and you're starting to understand where the dirty laundry in the company is."

Then we get to sell the vacation, right?

Then we get to say, "Look, all right, so fast forward 6 months from now and we're working on this problem together and we've solved the churn in the engineering department or in the design department or whatever. We've solved

that and we've got two product launches under our belt." when you head into that board meeting next, how can we ensure that your head is held high?

So, what I'm doing is I'm psychologically walking them to a position of like a painless position. I've removed

the friction and the pain from their shoulders and I forced them to visualize a utopian situation. And who was right next to them doing that? I was. So, when

it comes to your competition, there is no competition. I'm the only person who

no competition. I'm the only person who walked you into a vacation that you want to be in looking forward to your head held high in a board meeting that's usually stressful but instead this time

because you worked with me it's not stressful then all of a sudden when it comes to the offer stage there may be five other PMs but I can only imagine working with Jacob and so when I push back the likelihood that I break the

rules is significantly higher than if I hadn't done that. This is amazing. So

trying to just summarize what you're sharing here. And I think it's important

sharing here. And I think it's important for people to also note like you can do it in your own words. This is likely not something you'll just be able to pop out and do like this is something that takes time to do well and it feels awkward

probably and that's why people work with you that they like you probably roleplay and all these things but still like there's things people can pull out of this that they can do on their own. It

>> it could be tricky to understand where your value is, right? Because you're so close to it. You just do this every day.

And for, you know, product folks that only listen to product folks and and are in the product ecosystem in your bubble, Lenny, they're not seeing the impact on marketing. They're not having those

marketing. They're not having those conversations necessarily. So, it's so

conversations necessarily. So, it's so ingrained in everything that you do that you could functionally be excellent, but in order to break these boundaries, you have to be crossunctionally understanding how it impacts others and

the motivations of others. That's when

things really start to unlock. And

that's where just understanding a little perspective can be helpful in that outside influence there.

>> I I think this is important to just briefly summarize your approach. So the

idea here is uh figure out in many ways what matters most to them, what problems do they have, what they see in you, just like understand the landscape of where

you could bring tons of value. Help them

see that like here's the problem that I can help you with. Here's the problem that you have that we need. like here's

the many problems that we can help you with and then help them visualize you described it as sell the vacation help them visualize okay now that this was solved how is how how awesome would that

be and part there's like all this psychological stuff you're throwing in there just like how do >> I can really make this concrete with a quick story >> let's do it >> so

there's a very famous musician who was born the same year as me for those super sleuths out there who had a tour, a billion-dollar tour and a documentary.

And the director of said tour was a hot commodity in Hollywood. Every agency

wanted to sign this director. This

director didn't want to just do movie documentaries, right? Wanted to start

documentaries, right? Wanted to start producing actual movies. Like that's the dream, right? So, every agency wanted to

dream, right? So, every agency wanted to sign this hot director who just did this billion dollar deal with people already know who it is, right?

And so my client, the agent, asked me like, "We got to sign this. Like, it

would be stupid to go to any other agency, right? We've done this. We've

agency, right? We've done this. We've

done that. We've represented Julia Roberts and and Matt Damon and all these just naming name dropping, right?" Now,

this is actually a problem because if we're leaning on logic and credibility, we're losing, right? We need to sell the future and and own the emotion. And so,

she just asked me, "How do we close this deal?" And to me, this was very simple.

deal?" And to me, this was very simple.

I said, If you already had the job, who would you introduce him to?

If you already had it, the deal's already signed. So, put yourself in the

already signed. So, put yourself in the position that you're already doing the job. That's why in interview process, if

job. That's why in interview process, if you treat it like you're consulting, you're doing a value exchange and you're increasing your value and you're asking the right questions. If you feel like you're on the outside and you're having

to say, "Well, look, Lenny, I did this and I did that and did you see I have, you know, three million words written?

Like, why wouldn't you want to be the guest?" You're like, "I don't care about

guest?" You're like, "I don't care about what you've done. I care about what you'll provide my audience. Right? So,

in this deal, we get into the meeting.

It's a big day, right? And I said, make the make this schedule the appointment already. Work with the assistant.

already. Work with the assistant.

Schedule the appointment, right? With

whoever it is it needs to be. Needs to

be a big name person. So, we go into that interview and inevitably the conversation goes, "Why should I sign your agency?" And so, my client says,

your agency?" And so, my client says, "What are you doing on Friday? I cleared

a lunch with your assistant." And he says,"Well, I guess I'm going to lunch."

And she's like, "Great. I'll have you meet Stephen." And he said, "Stephen

meet Stephen." And he said, "Stephen who?" And she said, "Stephen Spielberg."

who?" And she said, "Stephen Spielberg."

And then some form after that, it was where do I sign?

Because the meeting was already set with Steven Spielberg. For somebody who wants

Steven Spielberg. For somebody who wants to get into film production, what better meeting to have, right? So for the other agencies,

have, right? So for the other agencies, they're like, "We're the greatest thing.

like we've represented this director that did this media tour and we did that. They lost because we sold a

that. They lost because we sold a vacation and we made it a reality right then and there and the value was clear.

>> So there's both this mindset shift of I am I'm going to try to actually help you figure out where I can be helpful and where the problems are and then start actually thinking about how to fix this.

And also there's like try to even do it.

It sounds like you could just >> if you can do it. So, one of the tricks of my business is >> like I I can plant seeds with my clients really easily because I'm on the phone with somebody and I'm understanding who

they need to connect with. And so, they might say, "Oh, I need, you know, I've been interested in getting to to Google or whatever." Let's say they're in

or whatever." Let's say they're in product. I said, "Oh, I I have somebody

product. I said, "Oh, I I have somebody in product at Google. Let me make a text for you real quick." And I'll just do it while I'm on the phone with them. Just

hold on a second. Hold on. And then what happens is they get the beep. That's

reciprocity. Like, I'm triggering a reciprocity imbalance. and then I'm

reciprocity imbalance. and then I'm making another one for them. So, I'll

sometimes do two or three introductions right then and there and they see the value before I'm even off the phone.

What I've also done is I've given three different touch points where I can make sure that that person is following through. I can get a 360 degree view of

through. I can get a 360 degree view of that person. I can ask one of those

that person. I can ask one of those people to prompt them to close with me if I need to sell a deal. I'm getting a reciprocity imbalance. So, what I want

reciprocity imbalance. So, what I want to do is show that I have the resources to support them whether they sign a contract or not.

And that's where we go in in this instance. Like, if you want to role play

instance. Like, if you want to role play with me for a second, something that would be really exciting like Lenny, I want to understand what's exciting to you. If today's podcast was the best

you. If today's podcast was the best podcast, the highest performing podcast that had ever happened, right? What

would that mean to you? And also, what did we do to make it so successful? What

are the comments that people had to put down below? Like what are the things

down below? Like what are the things they said to make you feel like my conversation with Jacob was the best conversation I had all year? What would

that look like to you?

>> Like I immediately love this question as a you know like it sounds to people like this as manipulative and like it could come across as that as an external observer, but to me I'm like this is exactly what I want to achieve and I

love that you're thinking about this and I want you to be focused on this and I would do a lot to help make this happen.

Uh, I guess to answer your question, I would just love it to be uh very concrete tactical advice that people can use to help negotiate their comp. And

they spread this with all our friends.

They're like, "This is the best thing I've ever heard around comp." And one of the things that we can do is that we plant what you want someone to say in that conversation as well. So when I'm

talking to these executives and I'm making the introductions, sometimes I'll ask or introductions come to me, I'll be curious like when you go back and you share with a friend, what are you going to say about me? Are you going to say

Jacob was really helpful or are you going to say that Jacob is an Right? I'm curious. And sometimes I just

Right? I'm curious. And sometimes I just make a complete reframe. So there's no other option, right? Well, I'm obviously not going to say you're an So I'm going to say you're the great thing that I want you to say. I'm controlling

the narrative I want them to perpetuate.

So, in this instance, and maybe some of your readers are going to be like, "This guy's a total manipulative jerk." Right?

I will say I hope that you use this for good and not evil, but this is just the way power works, right? I would hope that in the comment section you say, "Lenny, this was such a refreshing and

energetic podcast. Like, this is what we want more

podcast. Like, this is what we want more of. This is exciting. We've done a lot

of. This is exciting. We've done a lot of stuff in AI. This was very cool and different, right? So, I'm I'm suggesting

different, right? So, I'm I'm suggesting if you felt that way, share something like that below, right? Too many YouTube videos are like, "Oh, like and subscribe." And that's all they do,

subscribe." And that's all they do, right? Which does trigger action. It's a

right? Which does trigger action. It's a

very simple thing. But when it comes to navigating your net worth and negotiating for power, these executives at the top control what every other

person is saying naturally. They know

when somebody's talking about them when they're not in the room. And they've not only know about it, but they know what they said about them. Similar to when somebody's like, "Oh, Lenny, we're going to do reference checks on you." What's

the first thing you do? You call all those references and you say, "What are you going to say about me?" Right?

Ideally, you can control that to some capacity and improve the likelihood of you moving forward. So, we already do this. We just have to integrate it into

this. We just have to integrate it into some everyday conversations and you can better control outcomes. It's the same interview process. When you go back to

interview process. When you go back to your committee, are you going to say, "Jacob solved XYZ and we're excited like slam dunk. Let's move forward." And I

slam dunk. Let's move forward." And I like really quickly slam dunk, right?

Easy to remember. Or are you going to say there's a couple gaps here in some of the competitors that we have or some of the competition seems more fulfilling. And I want to ask for that

fulfilling. And I want to ask for that feedback while I'm still on the call with you. I don't want to wait for an

with you. I don't want to wait for an email to say, "I'm sorry, you're not a fit." And then you ask for feedback and

fit." And then you ask for feedback and you don't get any. I have to do it while we're live in person because you can't deny me in that moment without it being awkward. So, what are you going to say?

awkward. So, what are you going to say?

Is this a slam dunk? What's one thing I should have asked that I didn't? What

are some areas that the other candidates excelled that you wish I showed more of? Right? I want to understand where those gaps are so I have an opportunity to address them. And

then if I didn't make the mark, say, I'd love to have a conversation with you next Thursday to talk through that in more detail. Thank you for bringing that

more detail. Thank you for bringing that to my attention. and you close the next conversation. You don't give up

conversation. You don't give up necessarily.

Anyway, that was another monologue, but that was uh that was a little bit inside the mind how I think about these things.

>> No, this is so awesome. So, you know, if you think about a hiring manager, having someone like like I don't know, let's imagine I'm interviewing for a role. If

I come to them, if and say, "Here's the problem. I'm going to solve churn for

problem. I'm going to solve churn for you. I'm going to fix your onboarding

you. I'm going to fix your onboarding flow. I'm gonna figure out how to level

flow. I'm gonna figure out how to level up your design experience because I know that these are big challenges for you right now. Like if I was the hiring

right now. Like if I was the hiring manager, I'd be like, "Holy this is awesome. This is I just need someone

is awesome. This is I just need someone to come in and solve these problems for me. This is

me. This is >> and you better deliver, >> right?" And that's the other thing is

>> right?" And that's the other thing is >> it sounds like if this guy can't deliver, >> it's not going to happen. Or if this gal can't deliver, that's frustrating, right? I'm not suggesting go so far

right? I'm not suggesting go so far outside of your comfort zone that you feel like you can't, right? because that

reputation will haunt you, right? You

have to really understand. And I would also add that I wouldn't be so sure that I'm going to fix the onboarding flow. I

wouldn't be so sure that I'm not so sure that you know that's the problem yet.

The longer we can drag out the hiring process, and this sounds like pulling teeth, especially when you're unemployed, like I just want the pain to be over. I am asking you to slow it

be over. I am asking you to slow it down. The more you slow down the

down. The more you slow down the process, the more you fight back about the manufactured urgency of us needing to get into that role sooner, the more information you're going to understand

about that company and how you could really help. Right? So, you could say,

really help. Right? So, you could say, you know, Lenny, I hear that you want to fix the onboarding flow. I hear that. I

hear this. But it sounds like that product might be deprecated anyway in this wave of AI. Is that a possibility?

What I don't want to do is prioritize something that the team's going to cut, right? that's going to hurt the P&L or

right? that's going to hurt the P&L or whatever. Now, I can only ask that

whatever. Now, I can only ask that question if I've truly asked the right questions to understand, right? So, you

may come in, this is the same concept as never be so sure of your worth that you wouldn't accept more. You're so sure of the job description that they need these three things that you don't even try to ask the questions to understand what the

deeper problem is. And this going back also to why founders might be frustrated with my talk track. I'm not asking for you to take your pie and give them a bigger slice. I'm asking for you to work

bigger slice. I'm asking for you to work with somebody to expand the pie so everybody gets bigger slices. That's the

that's the plan. And if you train your candidates and you're more revealing and if their performance is tied to it, naturally they need to ask more questions to understand how to make it

true. That's what we want. That's

true. That's what we want. That's

putting companies up into the right. I

like that you went there around don't overpromise because it's easy to say we're going to solve all your pain for I'm going to I'm going to be the >> never over under promise overd deliver always under promise overd deliver.

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There's this balance of being confident in your abilities to achieve something big and solve problems and then there's this other piece of just don't overpromise. Is there anything you help

overpromise. Is there anything you help people do to help feel more confident about they will actually be a huge asset to this company and they're worth all this extra money? How do you is it like a pep talk? How do you help people?

>> Yeah.

>> Part of my hat is hype man hat, >> right? You got to be a hype man to a

>> right? You got to be a hype man to a degree. And I work with some of the most

degree. And I work with some of the most privileged and successful people in the world, right? It's not that hard to say,

world, right? It's not that hard to say, look at your life and look at your choices. Most of the things you've done

choices. Most of the things you've done have been good, right? At least

financially, right? We could debate about the ethics of the companies they work for and those things. Right? Now,

most of the decisions that you've made in your career have made you a top tenth of a percentile of the earners on the planet. Don't tell me you're not

planet. Don't tell me you're not confident. like you can't pull that.

confident. like you can't pull that.

Another thing that I do is that I put it I I reframe everything in a language they understand. So if I'm working with

they understand. So if I'm working with a sales leader, a job search process is an enterprise sales process. Like if you understand enterprise sales, you understand how to do this. You just

don't know how to do it for yourself. If

you're in marketing, you should know about positioning and market research.

That's the same thing as going into a job market and understanding what to do.

You understand that an inbound lead is much easier to close than an outbound lead. If you're in product and you're

lead. If you're in product and you're orchestrating a PRD, right, it's the same thing. You're understanding the

same thing. You're understanding the user's demands. You're creating for

user's demands. You're creating for those demands. You're optim like you're

those demands. You're optim like you're developing the right flow. You're making

the design as simple as possible. You're

eliminating friction. That's a term I use a lot, which I know product leaders will use also. We want to eliminate friction, right? How does that look in

friction, right? How does that look in your job search? Well, what does the customer want? Who's your buyer? The

customer want? Who's your buyer? The

buyer is the hiring manager. Maybe it's

the chief product officer. Maybe it's

the CEO. What do they care about? When

you're doing it for a company, you know which customers to interview. You know

how to do that. Well, you need to interview lots of CEOs. You need to interview lots of sales people who are trying to solve this growth problem or lots of AI sign. And again, it's not just product, right? So, you're now

interviewing your customers. You're

understanding their needs. Now, you're

designing solutions for their needs.

Now, how do you make it as frictionless as possible? So, it's a no-brainer and

as possible? So, it's a no-brainer and they go through your user flow as easy as possible. So for product folks,

as possible. So for product folks, instead of thinking, "Wow, this stuff sounds like Machavelian manipulation and it sounds like a power trip and it sounds like something I could never do

because I'm not maybe I'm not as gregarious and maybe I'm not a 6'3" tall white dude in California who's got the sales persona and he's got that

extraversion. I'm not that. Don't Don't

extraversion. I'm not that. Don't Don't

be me. Don't be Jacob Light. Be you,

your authentic you, and apply it to what you already know. You know how to do this in product. Design it for your career. And you remember the early days

career. And you remember the early days of writing PRDs and how rough it was.

Remember how rough it was to go back to the engineering team and just little by little get product sprints out where the product is just moving a little bit at a time. Remember how hard that was? The

time. Remember how hard that was? The

early days of managing your career like this will feel like that, too. But you

also know that if you're 10 years in your career, this stuff becomes second nature, right? So I want to reframe to

nature, right? So I want to reframe to the experiences that you already know and that will develop confidence. I like

this framing you're referencing here for product people of this idea like you're basically trying to position yourself the way you would position a product kind of the value prop of the basically

as a product team. You're trying to sell people on here's why this product is worth paying money for. And in this and you do that by understanding you do user research you understand their pain points you understand how to position it

so that you make it clear this will solve your pain point essentially that's what you're describing from when you're interviewing is think about it that same way the part I don't want to gloss over

is making it frictionless right so interviewing is a skill on both sides most people don't know how to interview very well it's tell me about yourself like tell me about this product you built tell me about that how that looked

you don't get anywhere talking about the past like you you might build credibility and and all that. Great. You

don't start solving problems in that process. So they're like, "Okay, well I

process. So they're like, "Okay, well I saw that. Now you're going to go on to

saw that. Now you're going to go on to the next person. They're going to do the same crap, right? Same thing. Same

thing. Same thing." So you repeat your story, add nauseium, and you never learn anything and you never grow. So how do we make this frictionless? Well, I want to make it cognitively easier for you to

have a conversation with me by leading.

That's why I had that framework I was talking about earlier, like why am I here? What are the problems you have? I

here? What are the problems you have? I

suspect it's this. What have you done about it? What would it look like if we

about it? What would it look like if we solved it? Now, I'm taking so much of

solved it? Now, I'm taking so much of the pressure off of you. I'm controlling

the narrative and I'm collecting more information while revealing none about my comp expectations. And what I'm focused on is creating as much value as possible. Now, there are situations

possible. Now, there are situations where companies don't have the budget, right? Like, this isn't a miracle drug

right? Like, this isn't a miracle drug kind of thing, but I'm making it frictionless to at least get to the part where they want you. That's the first step. They have to want you for you to

step. They have to want you for you to have any leverage. Right? Then even in the interview processes, I might say, "Hey, Lenny, you know, I suspect the next person I talk to from your ecosystem is Mark Andre." Right? Can you

give me some advice on how I should work with Mark? I want you to coach me on how

with Mark? I want you to coach me on how to deal with Mark.

That's going to make it more frictionless. Right now, I also want to

frictionless. Right now, I also want to put you in a position to be a coach because coaches want their players to succeed.

So, if I'm having you coach me psychologically, you're going to go talk to Mark and you're going to say, "Hey, Mark, you're going to have to talk to Jacob for all these reasons, right?"

Then, when I talk to Mark, I get to say, you know, Lenny shared that I should talk about X, Y, and Z thing. Are those

is that really what you care about? I'm

making it frictionless across the process and I'm closing the next part of the conversation regardless of whether you wanted me to introduce me to those other people or not. So, you might say, let's say you're interviewing for a

product role. I suspect you want me to

product role. I suspect you want me to talk to the head of engineering. I

suspect you want me to talk to Clay, the VP of marketing. And I suspect you want me to talk to Katherine, the VP of sales, right? What would you like me to

sales, right? What would you like me to say to them? What's the message you want me to share? And they may not have had them in the interview process, in the cycle, but I'm putting them in the

cycle. Like, I'm making it easier for

cycle. Like, I'm making it easier for you to know who to introduce me to next.

And then I'll even go as far as saying I'm not available again until Thursday.

What's the chance that time works? So

I'm building scarcity about my time. I

can meet with this VP then, but I'm making myself stickier in the organization. I'm getting more knowledge

organization. I'm getting more knowledge about what people need, right? So this

is similar to selling an enterprise deal. You're building champions in the

deal. You're building champions in the organization that love you and they're all coaching you on how to coach like to work with each other. So you're getting the inside scoop on how to navigate

that. That's how you become

that. That's how you become hypervaluable. You need to create that

hypervaluable. You need to create that leverage if you want to take that standard 20% we talked about and make it 40 or more. That's why it starts much sooner because if you're not doing that,

if you come to me and you're like, "Jacob, I have an offer. I can get you maybe 40." Right? If you come to me

maybe 40." Right? If you come to me sooner, I might have elevated that initial offer 40 without you knowing it and then we moved it even further.

Right? So it's a big process that we need to be mindful of. So it seems like a big part of your process and advice is to flip it, flip the interview as much as you can to extract information so

that you can build a case of how you will solve their pain. Say you're like an IC product manager interviewing at Meta. What are the odds you can kind of

Meta. What are the odds you can kind of flip these conversations or take a big chunk of that talk from them asking you you know their standard questions to you asking them what problems what are the biggest problems what would be awesome

if I came in like all that stuff you shared about to extract to build this case later one of the things I found frustrated about IC roles is they're not often rewarded as well as leadership

roles which is frustrating because there are a lot of very talented IC's now I have seen specifically with meta I actually interviewed for a meta IC manager role like an I9 that was like

1.2 million a year. They were

specifically hiring former CEOs and I found that to be interesting. They hired

150 growth PMs at this I-9 level and they were rewarding them very well. I

don't think it changes. I think that whether you're a leader of people or you're a leader of process, you're still a leader. And the reason I propose

a leader. And the reason I propose taking ownership of the conversation isn't to be steamrolling or talking over people or or completely like I'm not saying do this devoid of context. You

don't just blow out and like talk over somebody and ramble, right? Which I'm

one to talk apparently, but uh you go into this conversation and you eb and flow with them, right? But you the reason I want you to take ownership is because I can't control who you're going

to get on the other side of the line. I

can't control the mood they're in. I

can't control their motivations. I

can't. So, as a coach, I can't control how they show up, but you can control how you show up.

and we can work to navigate. And then

you start to get some, I guess, u nuance skills where you read body language and you feel comfortable saying, you know, Lenny, I saw that that maybe wasn't the right thing to say. Can you tell me more about that? Then you start getting

about that? Then you start getting confidence. And I say assertiveness, not

confidence. And I say assertiveness, not aggressiveness. There's a difference.

aggressiveness. There's a difference.

And so that comes across as confidence.

And so I don't think there's a difference between being an IC and being a leader in terms of how you approach this. But I have noticed a difference in

this. But I have noticed a difference in the pay and that can be frustrating. So

that means if I were working with more IC folks, I would ask questions like it sounds like, you know, independent contributor roles are very valuable at Meta. Can you share a little bit about

Meta. Can you share a little bit about how they're valued compared to leaders on the team? I might ask a question like that because again, they can't say we value you less. I've given them a

reputation where they have to say we value you. Then you get your offer, you

value you. Then you get your offer, you check levels or you check some of these benchmarks because we all do it, right?

We look, we want to know, right? Maybe

we call about a couple friends that are similar level. Then you can use

similar level. Then you can use objective criteria against them. You're

like, you know, you mentioned that you valued IC's as much as leaders, right? I

just got curious, so I did a little digging and it it looks like this this is like about 30% under what a leader would make. Is that is that normal?

would make. Is that is that normal?

Right? I appreciate you being an advocate for me and pushing back. can

you help me understand if we could lift this to be uh more equitable?

Right? I'm using information I gathered for them and I'm not just beating them up with it. I'm just saying like you said we treat this fairly. Prove it

or prove to me that you lied.

>> And this and this works is what you're saying because that like if I was the hiring manager be like no I'm sorry that's just not how it is. I mean, in in many cases it can be, right? But I'm

trying to I'm trying to open up an emotional conversation more so than logic and credibility because you lose you'll always lose the logical and credible argument against a company.

There's information asymmetry here. Meta

negotiates thousands of times a day. You

negotiate four or five times in your career. That's it. Right? Thousands of

career. That's it. Right? Thousands of

times a day. Recruiters thousands of times a day. You are at such a disadvantage. This should also give you

disadvantage. This should also give you confidence to negotiate in the first place. you are at such a disadvantage,

place. you are at such a disadvantage, right? I just wrote an article on uh the

right? I just wrote an article on uh the game of werewolf as an example about how important information is. So the game of werewolves, pretty simple. Say there's

12 people sitting in a room, two, three of them are werewolves, right? They draw

a card at random, three people, two people, whatever. They get their card

people, whatever. They get their card and they know they're werewolves.

There's a day and night scene and the werewolves get to reveal themselves to each other. So they say, "Oh, you're a

each other. So they say, "Oh, you're a werewolf." Yeah. Okay. We're werewolves,

werewolf." Yeah. Okay. We're werewolves,

right? Then they go round by round and they politic to vote somebody off of the table, right? Only two two three people

table, right? Only two two three people understand, right? When the werewolves

understand, right? When the werewolves reach parody with the villagers, the werewolves win, right? In even a like a

six to1 or a 5 to1 situation, werewolves win 60 70% of the time, right? It shows

the power of information. They

understand everyone else is clueless.

They know who's dangerous. They know

who's not. And that's just a that's a outnumbered situation. Now these

outnumbered situation. Now these companies have significant leverage over you. They know what people make. They

you. They know what people make. They

know what others make. They know what they'll accept. They know their budgets.

they'll accept. They know their budgets.

They know how to change the budgets. And

what I find interesting, especially with executives, they push back on this process. And I'm not going to lie, it's

process. And I'm not going to lie, it's much easier for executives to do this than it is for middle managers or lower.

So if you are a hiring manager, Lenny, and you put your director hat on, like it's easy to deny somebody like that because it's a little bit easier to find another product manager a little bit, right? If we do our job to

right? If we do our job to differentiate, then we're doing better there. But executives that are afraid to

there. But executives that are afraid to push back, like your job is to make these rules, you know who to influence to change them. You understand how the

P&L works. That's what you do for a

P&L works. That's what you do for a living. And you're telling me there's no

living. And you're telling me there's no flexibility?

You built it. Humans built this. This is

not concrete authority. This can be influenced. Why not try? Let's try to

influenced. Why not try? Let's try to summarize maybe the top five tactical tips that you've shared. If we were just to kind of go through in bullet points, just things people should keep in mind

when they're trying to negotiate. Like

one that comes to mind is don't speak don't share the number first. Try to get them to share a number first. Is that is that right?

>> Yeah. You also have to know how to respond if they share the number first.

I'd rather no numbers be discussed if you're open to just waiting it out and seeing. So important pieces. Uh so the

seeing. So important pieces. Uh so the first one is you'd never be so sure of your worth that you wouldn't accept more. That's I think Chris Boss quotes

more. That's I think Chris Boss quotes that quite frequent. Uh the other one is never split the difference. And I have a I have a good story about that. So just

because somebody says, you know, you start at 100, they you say 200, they come in at 150. That's lazy, right? One one brief

150. That's lazy, right? One one brief example of this, I had a chief revenue officer and they were paid $350,000 base

salary, 350,000 bonus. So 700,000 cash potential each year. Uh so that's called ontarget earnings. They'll make 700.

ontarget earnings. They'll make 700.

When we negotiated their severance, we said we wanted six months ontarget earnings. It was all agreed, right? The

earnings. It was all agreed, right? The

paperwork comes back and it says six months base salary.

not on target earnings. So that means six months of base salary is like 1875, right? So they cut his severance in half

right? So they cut his severance in half by doing that. Now his response was I'll just tell the CEO like let's up that 90 and it'll be down 90. He was going to split the difference to like 260 or

something whatever the mass out to. And

I said instead simply ask was that a mistake? Right? You know we had

mistake? Right? You know we had discussed on target earnings that was intentional. Was that a mistake? He said

intentional. Was that a mistake? He said

oh yeah it must have been. let me just tell the attorneys to fix it. Feel free

to redline it. See, he almost lost 90 grand just splitting the difference, if not more, right? And then turns out 12 months later he got fired and then he was able to recoup $350,000 over 6

months. So little things like trying to

months. So little things like trying to split the difference uh too early can be painful. So that was two points. I think

painful. So that was two points. I think

I know this is parts I'm bad at. Trying

to get a list of five.

>> This is great.

>> Patience is more important. Like things

need to slow down. Haste equals risk.

The slower you go, the more opportunity you have to collect information so that you can build a compelling case. Right?

That's important. Uh

I am a big believer in Aristotle and his principles of rhetoric and ethos pathos logos. And so I've mentioned a little

logos. And so I've mentioned a little bit of this in their more common tone of uh logic, credibility, and emotion.

Timing is another one that we don't often talk about. Chyros is important.

But too many executives lean on credibility and logic because we're trained to do that. We don't show emotion. We don't show the authentic

emotion. We don't show the authentic side of ourselves in corporate. I think

often times because we're working soulless jobs that we don't believe in and we're just trying to make do and survive for our families. I think

there's a greater need there.

The emotional side is where a lot of deals get unfair. So if we understand how to tap into that, I want to say Chris, I keep mentioning Chris Voss, but he I think he calls like tactical empathy, right? which does that sounds

empathy, right? which does that sounds more Mcavelian than anything I've ever said, right? But understanding those

said, right? But understanding those motivations and understanding how to play on that can be important, right? So

when we talk about giving people a positive reputation, we're playing into some emotions here. So if I'm a female negotiating with another female, I might say, you know, I appreciate that you've

always been an advocate for women and you support one another. Like that's

something I respect about you, right?

And then their cop comes in lower than a man's cop.

You can call them out on that and say, "If you were in my shoes, what would you do?" That's one of my favorite lines. If

do?" That's one of my favorite lines. If

you were in my shoes, like go backwards five years in your career. That's where

I'm at right now. If you were in my shoes, what would you ask for? I love

that when negotiations stall also, right? Like you know what's possible

right? Like you know what's possible here. You know what levers we have. It

here. You know what levers we have. It

sounds like we're capped out here. If

you were in my shoes, what else would you explore? And you start to go that

you explore? And you start to go that route as well. Um the other piece is this is a collaboration not a confrontation.

So if I could give visual advice oftentimes this is why it's also can be difficult in a zoom like you and I are kind of face to face like we have this problem between us right that's an

adversarial position. I want you to

adversarial position. I want you to physically pretend that you're in the same room and I walk to to your office and I put my arm around you if you're comfortable with it and I'm instead of

us arguing over something, we're whiteboarding a solution together. I

want collaboration in that's how we break down walls and barriers because you're sharing information, I'm sharing information, those types of things. The

I think that was four, maybe it was five. Another one is make it about we

five. Another one is make it about we not about me, right? So another

severance conversation uh with a chief marketing officer. This is a hundred and

marketing officer. This is a hundred and $200 million private company a couple years ago. So she comes in, she gets

years ago. So she comes in, she gets offered $340,000 base salary, 30% bonus equity, right? We tried to push on all

equity, right? We tried to push on all that and the CEO said, "Look, one of the things I pride myself in is that everyone here has $340,000 base, 30% and

the same equity package. Everyone on the executive leadersh need to push on more money. What we went for was severance protections, right?

And so we asked like standard is about six months maybe plus uh another month for every year served. And the CEO's like, "Oh, we've never done that before." And so instead of it being like

before." And so instead of it being like you're negotiating the terms of your divorce before you get married, that's what's awkward here. We said, "Well, given that we've had a problem with

talent being poached, you're going elsewhere and we just did a big riff.

Wouldn't it make us look good to proactively give everyone on the executive leadership team six months to show that they're safe and committed to the company? And then we fed that idea

the company? And then we fed that idea to the CEO so the CEO could look like the hero. More importantly, when my

the hero. More importantly, when my client came into that company, she looked like a hero because everyone's like, "That's the woman that negotiated us all severance protections, right?"

So, we made the company, we used the company's equitable policies to do that.

Now, I will say that's not common, right? So if f folks are like them

right? So if f folks are like them that's fantastical that may not happen like especially with private equity it usually doesn't right there are there are ways that we want to appeal to a

humanity more so if we can um bonus point I know I'm monologuing a lot don't be afraid to get creative like creativity is interesting and one time

we got someone a Gwagon after being like maxed out on comp. I like this story because it's so out of this world that you're not going to get a Gwagon.

promise you it is likely not going to happen. But we had this CEO who had two

happen. But we had this CEO who had two offers that were both 2.4 million and they were stalled like oh first world problem right like tiny violent 2.4 4

million a year this CEO deal. And she

told me, and this was just a joke, like this wasn't some Mavelian plan. She was

like, "Look, I don't know which to choose. They're both maxed out." And I

choose. They're both maxed out." And I was trying to say, "Which one would you like more?" She wasn't giving me

like more?" She wasn't giving me anything, right? They're both fine.

anything, right? They're both fine.

Whatever. I And I said, "Well, I don't know. What kind of car do you like?"

know. What kind of car do you like?"

Right? And uh she she's, "Oh, I love Mercedes." Right? Right. And I tell them

Mercedes." Right? Right. And I tell them that like jokingly cuz they they inevitably came to look what's it going to take to hire you? And she's like I don't know like oh maybe a company car.

And they said well what kind do you like? And then she said Mercedes. And

like? And then she said Mercedes. And

they're like done. What model? And then

she's like oh a G Wagon. And what

happened was all the budgets were capped but it was a company write off to have a 6,000lb vehicle. So, it was a $350,000

6,000lb vehicle. So, it was a $350,000 car added to her contract that was a company ride off that reduced the tax expense. So, like that's not going to

expense. So, like that's not going to happen. I don't suggest people go ask

happen. I don't suggest people go ask for G Wagons, but the fact is we came to a stall point and we found a solution for that.

>> I love these stories. Uh, another tip you should just want to double down on is don't take is don't negotiate over email. Make it in person as if possible

email. Make it in person as if possible or video call, right?

>> Yeah, absolutely. You just you have to be more comfortable understanding the body language and the tone you're picking up these things that you can't control when somebody opens their phone.

Like the worst thing is they're on their way to pick up their kids at school and they open your email and it just doesn't sit right with them and they're in traffic. Like you can't control whether

traffic. Like you can't control whether someone's going to do that or like I said earlier being busy at the airport rush through security or they just got off a call with somebody that's frustrated. But if I hop into a video

frustrated. But if I hop into a video call and I can see that you're visibly frustrated, like if for whatever reason you look like your toddler kept you up all night, I'd say, "Hey, Lenny, would

you like to reschedule to a time that feels more comfortable for you, right?

So that we can get the most out of our time together." Like that is a blessing,

time together." Like that is a blessing, right? You couldn't do that over email.

right? You couldn't do that over email.

Say things actually do fall apart. Say

you just push too hard and they're just like, "Okay, we're going to move on with another candidate." where they make you

another candidate." where they make you an offer and they just they rescend it or they promise something and they don't deliver. How do you approach when things

deliver. How do you approach when things go sideways? Couple couple elements to

go sideways? Couple couple elements to that story. One that the not delivering

that story. One that the not delivering pieces that's more common. Rescended

offers I have never had a client with a rescended offer. The what I will get is

rescended offer. The what I will get is a no. This is a top take it or leave it.

a no. This is a top take it or leave it.

Right? Fine. They go they get an ultimatum. Fine. I have however helped

ultimatum. Fine. I have however helped somebody. They weren't a client, C also

somebody. They weren't a client, C also a CMO and she was offered an $800,000 contract total

cash-wise and it was rescended. And so I I took this case on proono. I got a phone call. I

was like, I I just want to see how this plays out, right? And she was in tears.

She lost this deal. She turns out she had a career coach that said, you need to negotiate like a white man. Like that

was her advice. Like you need to be aggressive. You need to do this, you

aggressive. You need to do this, you need to do that. Like you need to negotiate for your worth, which you know I understand the appeal of that as like if I would understand like a woman that wants to negotiate like a man and get

hers, I respect that. Right? In this

situation, the context that was missing is that she was negotiating with other women. So she was negotiating with this

women. So she was negotiating with this female CEO and three other females on the executive leadership team and they rescended the offer because it sounded like she was a bad cultural fit.

because she was acting like a man. Like

she wasn't being her authentic self. She

was acting in this persona that she wasn't comfortable with. And to be honest, she said to me, I wasn't comfortable with that advice, but I did it anyway because women should stand up for each other. We should push, right?

And I commended her for that. And so

what we did was I said look call the CEO explain what happened share that you know obviously it's important that women take care of

each other right and it's clear to me that you have there's that positive reputation right I got to be honest with you I hired a coach to try to understand

what to do because in the past I've failed in the past I haven't been my best advocate in the past I've done less I suspect you know what that's like.

Boom. Shared identity, right? They all

know. All women know this together collectively. This is a shared identity

collectively. This is a shared identity tribe thing, right? I made a mistake and I I I disagreed with the advice, but I did it anyway because I had to try and

brought the offer back on the table for her authenticity and transparency. It's

like that was the path that we It was two phone calls to come up with that idea. She got that deal back on the

idea. She got that deal back on the table is now happily making 800,000 a year. Right? So when things go south,

year. Right? So when things go south, approach it with honesty, integrity, say like, I made a mistake. Take ownership.

Extreme ownership really helps here.

That could probably be one of those those points. When you fail to live to

those points. When you fail to live to deliver, take ownership of that. Take

that note. It may mean you're getting level set a little bit in your career.

That's okay. You're still growing. That

is so I love that approach of just like, okay, I hired this coach. They gave me bad advice. It wasn't actually.

bad advice. It wasn't actually.

>> It made me feel good, too. I was like, she should have hired me.

>> It's interesting how negotiation is different if you're a man versus a woman. Do you take a different approach

woman. Do you take a different approach if it's a female client versus a male and it's just like here's you should approach it this way or or it depends on the person.

>> I take a different approach on every person. Yeah. So whether you're a

person. Yeah. So whether you're a product leader or a marketing leader or a sales leader or you're from San Francisco or you're from Dubai or you're from New York or you're from LA like or

you're German or everybody is different culturally. So male, female, like every

culturally. So male, female, like every little nuance is is important. If

you're, you know, you're gay or you're black or you're there different challenges that everybody has to overcome, right? And I remember this was

overcome, right? And I remember this was a powerful one. I was speaking to chief.

There's about 400 women in chief, and I'm the I'm the white dude manplaining to all these women about negotiation.

It's like the scariest position for me to be in. And I remember there was this African-American gal and she said, "Jacob, should we just negotiate for 84% because that's what we're going to get

anyway, right? Like that's defeist. Like that

right? Like that's defeist. Like that

sucks to have that feeling." Right now, I don't know what that feels like. Like

I have I have done fairly well for myself and there are some advantages that I had. But I said, "Look, like how many of you in here are mothers?" Many

of these women raise their hand, right?

How many of you are mothers to daughters? Right? Many of them raise

daughters? Right? Many of them raise their hands. I said, 'Could you look

their hands. I said, 'Could you look your little girl in the eyes and say, "Sweetheart, just get 80% out there.

Just go after that. Do that, right?" And

it kind of like shocked the room a little because I I can't compete on that level, right? I don't know what that

level, right? I don't know what that feels like. I can't do that. But I said,

feels like. I can't do that. But I said, "Look, if we don't learn to grow together, we're never going to solve this problem." So, what we're trying to

this problem." So, what we're trying to do here, and this is what I encourage all listeners to do, fight back. There's

a big power imbalance, right? Here,

here's the founders coming in again.

Like, Jacob, don't tell them to do that.

I don't want to revolt, right? Take care

of them, right? Push back because a rising tide raises all ships, right? If

companies want to rely on precedent, have the audacity to raise the precedent because the next people in line will will do that. To the point about collaboration, this was actually with uh

one of your readers that read the that first article we did.

Um, we made a lot of money on this deal >> and they came to work with you. Oh, I

love this.

>> Yeah. So that this is fun. Um,

>> but so this is kind of like a private equity hostile takeover situation and this reader of yours was getting pushed out of the company and if you try to go headto-head with the PE, you're going to

lose, right? He had a great relationship

lose, right? He had a great relationship with the CEO, 10-year relationship and but the CEO wouldn't take any action to support him, right? Intel, we made it

about we. The CEO had made comments that

about we. The CEO had made comments that I'm probably going to get fired, too.

Right? So, what we did was we talked to the CEO and we said, "Whatever precedent you help me deliver, you're going to get two to three times that. So, we need to set this up." Right? So, then they were

full on. You had the CEO and the CPO

full on. You had the CEO and the CPO putting together a game plan to advocate against the private equity, right? To

support that transition plan. We got a retention bonus and a severance bonus on the table because of that, right?

Because now the CEO is protected as well. Can point back to some precedent,

well. Can point back to some precedent, right? So not everybody does it out of

right? So not everybody does it out of the goodness of their heart. Not in a capitalist society, right? You have to show them your motivations here are important, right? So women negotiating,

important, right? So women negotiating, if you want women after you to have an opportunity, have opportunities and better opportunities than you have, you have to have the you have to have the

guts to do that. And that's very easy for me to say. I'm not in your shoes.

But naturally, we have to be a rising tide. And there are folks that aren't

tide. And there are folks that aren't going to take that challenge. And that's

okay, right? Let's all push for those to help it make it easier for everyone.

>> I love this point you made about how there's no one way to approach this. The

way I was originally thinking we'd do this chat is like a step-by-step guide to negotiating. Here's what you do. 1 2

to negotiating. Here's what you do. 1 2

3 4 and this is how your comp goes way up. And what you told me is that just

up. And what you told me is that just doesn't exist. There's so many

doesn't exist. There's so many variables. There's so many types of

variables. There's so many types of companies role seniority people's backgrounds. Maybe speak to just like if

backgrounds. Maybe speak to just like if you ever see someone telling you, "Here's your steps to negotiate comp just that's probably not real." That was one of the things that was hard about

the article we wrote together was that I have gains, right? It's a it's a process that I follow. It's not a concrete step-by-step process. But one of the

step-by-step process. But one of the reasons I'm so hesitant to go this route is because negotiation comes off so complicated. It's so complicated and so

complicated. It's so complicated and so academic when you look at the books that were written. You have well Chris Voss

were written. You have well Chris Voss has kind of popularized it lately. But

it's like imagine there's a gun to your head in an FBI situation. You're like I don't have a gun to my head. I just have dealing with my boss and I want to understand how to do this. Or you read Getting to Yes. And it's like, well,

what you need is a strong BATNA and a good ZOPA and it's like very academic and you're in the moment trying to have a conversation and have empathy and listen, but then you're like, what's my zone of possible agreement? What's my

best alternative to like those things are all very true, but it comes off intimidating, right? And

intimidating, right? And when we when we try to focus so much on frameworks and and academic, we stop listening.

And that's one of the most important parts is curiosity and empathy are the two things you need to have the most.

Right? If you're reaching a block, why does that block exist?

If you don't know the answer, you haven't asked the right questions.

Right? You don't necessarily know. It's

that information imbalance that you have. And really what negotiation comes

have. And really what negotiation comes down to information and timing. That's

what creates power, right? Those are the three things. That's all you need to

three things. That's all you need to know. You have to have the information.

know. You have to have the information.

when we were talking about that game of werewolf, even when you're outnumbered five to one, if you have more information, the odds are you'll win, right? So, I don't want it to be overly

right? So, I don't want it to be overly complicated. One of the

complicated. One of the I I guess I have to say it. So, I'm

trying to write a book this year. I'm

going to write it, right? I'm going to write it.

>> Now, it must happen.

>> Now, it must happen. I know. Like, I

just kind of clinched up a little bit because like I got I got to do it.

>> It's still early in the year. You got so much time.

>> Oh, yeah. Thanks. Right. I I'm a prolific writer. I'll get after that.

prolific writer. I'll get after that.

But the book title is called predetermined.

And I wanted it to be predetermined like with a question mark, right? Because

none of these outcomes are predetermined. No matter what situation

predetermined. No matter what situation you are in your life, how you were raised, it will it could be more difficult for you, but it's not predetermined. And it's it's one of the

predetermined. And it's it's one of the reasons I love this work is that I don't know what the outcome can be. We don't

know. You should never be so sure because then you start putting a ceiling on your life. And one of one of my favorite things to ask somebody and they're like, "Oh, Jacob, I want to do this in five years." I say, "What would

that look like if it was done in one?

What must be true?" And like truncating that experience just to think through it. Not necessarily that I'm asking them

it. Not necessarily that I'm asking them to rush through it or whatever, but I have clients that they'll have 10 or 15 million in the bank and they'll be in their late 50s and they're like, "Oh, I

need 10 to 15 more to retire."

What? What do you mean you need 10 to 15? Like if I had a million dollars I

15? Like if I had a million dollars I would retire. Like give me a break. Like

would retire. Like give me a break. Like

that seems like so much money to me. Why

is that the case? Right. Um so I like to challenge those those notions there.

Right? Um it's an important thing to think about like it's not as step by step as it needs to be because sometimes another one of my favorite questions, what would your life look like with

less? Maybe a minimalist or stoic type

less? Maybe a minimalist or stoic type philosophy. one of these Hollywood deals

philosophy. one of these Hollywood deals we did, uh, we had a director and a Marvel superhero that got in a spat on a big franchise.

>> Cool.

>> This is a estimated 500 million to billion dollar franchise opportunity.

>> This A-list celebrity uh, and their writer uh, on this third installment of a movie didn't like it. So, think celebrity kind of being a primadonna. I hate it. I

don't like the direction it's going.

They're not writing me right. Fire them.

right? Offended the original director because they wrote the first two movies and they were very successful, right, to build this franchise. So pissed off, right? Next writer comes in. This is

right? Next writer comes in. This is

worse than the one before. Can we just hire back the first one and get work through it? Right? So 6 months later,

through it? Right? So 6 months later, money, production delays, all that. Go

back to that original writer. And the

agency's like, "We got to throw money at this guy." like to get him to say yes or

this guy." like to get him to say yes or here's a million more dollars, right?

Didn't do it. Like a million dollars wasn't enough to mend this relationship.

The important lesson here is it's not always about money. That individual was making $10 million a year. A 10%

increase to have to go back to somebody they didn't like. Not powerful. Right?

My suggestion was, can you ask the actor, this A-list celebrity to humble themselves and apologize?

And that is what moved the deal across the line. Actually came in and

the line. Actually came in and apologized for the behavior. It's not

going to be like that. That's what got the deal back together and the million dollars was saved. So, it's not always about money. I use a lot of money in the

about money. I use a lot of money in the stories because it's kind of shock and awe. It's like, wow, like that's going

awe. It's like, wow, like that's going to have big impact. Like at the end of the day, if you're making $18 an hour and you negotiate to 24, that's such a material difference in your life. That

is so magical to maybe be able to afford gas for the first time, right? And then

I'm telling stories where people haven't thought about how much gas costs ever, right? So like there are situations I

right? So like there are situations I remember that I like just 10 years ago, well 12 years ago, I was homeless like fighting through all this stuff and didn't know if I could pay for gas. So,

it's one of the reasons I'm inspired to do that is that you can make a material difference and it compounds throughout your life, but it's not always about money.

>> I want to follow this Hollywood thread before we wrap up. Uh, I love that you work with Hollywood folks, uh, celebrities and also tech people, which is most of the audience here. Is there

another uh, wild story from your Hollywood life uh, that might be fun to share? I think what's interesting about

share? I think what's interesting about Hollywood is that it's so far-fetched in you were talking about what happens

when offers get rescended, right? And I

before I was working in Hollywood, I would I would try to talk people into asking for $20,000 more, right? Which

after taxes is like eight, right? And

then when you look at it's like $400 a month or whatever, you're you're struggling to maybe ask for 10 20 grand, right? in Hollywood like we did this

right? in Hollywood like we did this deal with I can't share who al-ist celebrity and the company said we want

to pay her $5 million for this movie and the attorney came back we want $22 million like talk about being aggressive right

and the production company's like all right how about 13 and this was in like a twoday span so they went from 5 million to $13 million in two days and

the other they're like well instead of 22 how about 18 right like they're moving $4 million chunks at a time and we're over here in tech going like oh I wonder if I can get 10,000

right so like that's something that I just find absolutely wild the bigger the op like this is just like you want to make money solve rich people problems right that's what happens right it's

it's just escalated I can only imagine what a negotiation with like Elon Musk would be like, "Throw a hundred billion at it." And you're like, "Oh my gosh."

at it." And you're like, "Oh my gosh."

Like, I also found out that a million seconds is like 11 days. Like, have you ever heard this? A million seconds is 11 days. Do you know how Do you know how

days. Do you know how Do you know how long a billion seconds is?

>> Like probably hundreds of years.

>> It's like 30 >> 30 years.

>> 31 years.

>> So between 11 day, that's the discrepancy between a million and a billion, >> right? And so these are just like these

>> right? And so these are just like these things scale so exponentially. It's just

that what you say and how you negotiate just kind of changes. So, if you want to really increase your comp, you do have to move rooms, right? You have to start networking and making connections with

folks that can do that with you.

>> Maybe as a last question, just to get very tactical, somebody that maybe is about to get an offer, got an offer, will get an offer in the near future, what's like what's the first thing they should do to help them increase the

comp? Is it just reply with is there

comp? Is it just reply with is there room for more? What's like what should they do when they get that email?

>> You always give me these nuanced ones, huh? So, it's

huh? So, it's they get it from the recruiter or they get >> let's say the recruiters probably Yeah.

>> recruiter is going to again they're probably going to have that 20%. We have

a room there.

>> If you're okay with that, I might again just say what's the chance we can we can bump like this is what I was looking for, right? I would probably knowing

for, right? I would probably knowing that the recruiter is going to split the difference. I would probably anchor

difference. I would probably anchor higher versus lower. There have been some studies and I was reading some I've read a lot of negotiation books. There's

like one from the 70s on these negotiation games and those who those who anchored egregiously high won 75% more than those who just tried to be

reasonable. Right? So it's like look I

reasonable. Right? So it's like look I was hoping for 150,000 more. Sometimes

you get 70, right? Sometimes you get 50.

But if you asked for 50 more, you would have got 15, right? So if you are going to re-anchor just say hey I was kind of in the ballpark of this again with the nuance you may have

already committed to a range before and it can be difficult to have that conversation right so I might say hey after we've had the conversations with hiring manager and yada yada it sounds like the scope of the role has increased

are you open to revisiting the comp structure on this that's likely how I would respond if the recruiter says this is all we can do and you have the

audacity to do this. I may send a text message or an email to the hiring manager and say, "Hey, we're almost across the line. It sounds like we had a sticking point. Are you open to have a

sticking point. Are you open to have a conversation?" That's who I want to

conversation?" That's who I want to close with. And I don't want to put the

close with. And I don't want to put the recruiter down and say, "It just sounds like we're at a sticking point here and I'm really looking forward to working with you. Are you open to chat real

with you. Are you open to chat real quick?" I don't need to have a big

quick?" I don't need to have a big laundry list of I'm going to do this for you and I'm going to do that. Like that

will not work. And I've noticed this in our back and forth and in your emails, like you'll respond with two words.

That's all you need, right? You don't

often need more. So like the more confident you get, the shorter your communication gets. And sometimes it can

communication gets. And sometimes it can be as simple as texting the hiring manager saying, "Open to chat." You

don't give them any reason. It's just

open to chat. And then you control the conversation.

Hopefully that was tactical enough. If

it's not, I do have a I have a lot of written scripts that are out there that you can copy and paste so you don't have to just rip the transcript down from all of Lenny's videos, right? I do have written scripts and guides for this and

I have a free course on how to do this, too, that's on YouTube. So, it's not like you're uh if you need the actual specifics, there are a lot of scenarios I've already kind of covered you can go.

>> Amazing. And we'll link to all that. And

I think it's I asked you what you were hoping to get out of this before we started recording. And uh just to be

started recording. And uh just to be clear, you're not looking for new clients. You're booked up. You're you um

clients. You're booked up. You're you um this is like you share all of this stuff out there. You have this free course.

out there. You have this free course.

You have all these Substack posts. So So

that's what I love about you. It's not

like, you know, you're trying to it's not like some deal leaf flow here. My

mission is to make what I've learned from very successful people more accessible, right? And if you put a pay

accessible, right? And if you put a pay band on all of that, you're not making it accessible, right? And my hourly fees are very high, right? So, it's like I

don't want to push for that and feel like I'm unobtainable. So, I want to give away as much as I can. And it's

these things shouldn't be gatekept. They

often are. But, um, yeah, I was mentioning a little bit in the green room. I just I felt a little powerless

room. I just I felt a little powerless growing up. Um, there's like some little

growing up. Um, there's like some little substance abuse and trauma as I was growing up and I never felt comfortable or safe. And so when I became a little

or safe. And so when I became a little older, I started to understand psychology a little bit differently because the same fear I'd have as a

child, I could see in the boardroom. I

could see the same fight orflight mechanisms, but that was far less scary, right? So it's just money. Money is

right? So it's just money. Money is

like, I'm not going to get hit, right?

Nobody's going to get hurt here, right?

So I could start to see that and I could see the body language and I can understand when somebody was in a tense moment. And all I ever wanted to do

moment. And all I ever wanted to do because I I felt that from a little kid was help that person feel safe, right?

Help them feel safe in that moment. And

so I've been obsessed over how to solve that for my entire career. First for

myself and then what became natural for me is for other people because I could see their growth and that's what became most fulfilling.

>> There's a whole uh other conversation we could have about that whole >> We got to be careful about that one.

Yeah.

>> All right. That one. I might start crying on that one.

>> Okay. Well, that makes good content.

That could be part two. Jacob,

>> that'll be the comments. Like, next

time, make Jacob cry, Lenny. Go for the kill. Go for the kill.

kill. Go for the kill.

>> I I hope not. I don't think my people want that. We'll see. Oh my god. Um,

want that. We'll see. Oh my god. Um,

okay. Before we get to our very exciting lightning round, Jacob, is there anything else you want to share?

Anything else you want to leave listeners with?

>> Just that if if you're going to take a chance, take a chance on yourself. I'm

sure a lot of these folks are parents or a lot of these people are are are parents and you want to you want to be the best version of yourself and show that your kids that you could survive anything. You're going to you're going

anything. You're going to you're going to get a couple bruises along the way, right? Like these are great first world

right? Like these are great first world problems to try to fight for, right?

Like it's not it's not going to it's not going to take away your home. It's not

the thing is you're only going to make life better around you, right? If your

cup overflowth, right? you'll be able to give more to others. So it's not about am I worth it is that it's like if you are a generous person naturally you can

be more generous if you have more wealth right if you're afraid of wealth this is something that really screwed me up like I used to despise wealth they despised

it right and I don't know why it was like miss like I didn't trust people with money I felt like they all had to be dirty or they all had to do something and to be fair a lot of people do things

that are highly questionable and unethical Right? And we see that in the

unethical Right? And we see that in the world around us. But if you fear it and you don't understand it, you'll never have an opportunity to change it. And so

you need to take some chances on yourself with this. And if I hopefully that's another piece, just having the confidence to go out and try. Even if

you fail, you're failing forward. You're

learning, right? You're going to find a style that works best for you. It's not

that Jacob Orwick's style is the style that's awesome or Lenny's style is the style. You don't need to copy anyone

style. You don't need to copy anyone else. You need to find that center that

else. You need to find that center that that works well for you and what you're comfortable.

>> That is beautiful. Uh I'm also realizing as we're talking, we haven't mentioned AI once in this conversation, which is incredible. I love

>> the the listener the listeners are like, "Oh, thank goodness."

>> Yeah, that's right. Thank goodness.

>> Just once in a while.

>> It's cuz I don't want AI to replace me, Lenny. I don't want it.

Lenny. I don't want it.

>> I Yeah, I like I don't even know. Anyway,

we're getting to it. Okay,

>> good. I got you speechless. That's the

job. If you get the podcast host speechless, you're doing your job.

That's great.

>> Okay. Well, we did it with that. Jacob,

we have reached our very exciting lightning round. I've got five questions

lightning round. I've got five questions for you. Are you ready?

for you. Are you ready?

>> All right. I will I will do the best I can. Yeah.

can. Yeah.

>> Here we go. What are two or three books you find yourself recommending most to other people?

>> Influenced by Robert Chaldini.

Sweet. That's the one. That's the one. I

mean, I like uh Herb Cohen's You Can Negotiate Anything. It's a little dated.

Negotiate Anything. It's a little dated.

>> Uh like old white dude in the 80s dated, so be mindful. It doesn't suit all audiences, but it's what I like about it is they talk about like negotiating dishwashers and stuff, not like going to

market with Meta versus Instagram and the acquisition. Like, it's not

the acquisition. Like, it's not complicated. It's like here's an apple

complicated. It's like here's an apple and here's an orange and here's the concept of negotiation. Really spelled

out simple. Um, I did just do a podcast with John Lowry and he wrote a book called Negotiation Made Simple and I remember reading it and I was pissed off

because I'm like I wanted to write a book a couple years ago and then I read his and said this like this is what I wanted to write. So I was frustrated and then I was like I'm going to reach out to him because I have a lot of respect

for him. So I did his podcast that'll be

for him. So I did his podcast that'll be live soon but yeah that was negotiation made simple. really breaks it down in in

made simple. really breaks it down in in an easy way and that could be like a bible. Uh then I like radical cander. I

bible. Uh then I like radical cander. I

know some of your guests put that on.

I've met Kim Scott. She's phenomenal.

Like that radical cander really gave me the confidence to be assertive in the ways that I never had been before. So my

wife taught me that. Kim Scott embraced it in the corporate world and like those two pieces like really helped elevate my career. I think Radical Cander is the

career. I think Radical Cander is the second most mentioned book on this podcast behind high output management.

>> Yeah, I have not read that. Uh

admittedly, I'm bad at consuming content.

>> I'm not I I only create I've got this rule that you create 10 times more content than you consume.

>> So I read like one book a year and now apparently I'm going to write one book.

>> So maybe that'll be the new goal.

>> That's a great that's a great framework.

Okay, next question. Do you have a favorite recent movie or TV show you've really enjoyed? I've been really liking

really enjoyed? I've been really liking watching Luca, the Disney movie.

Uh, having a toddler and a newborn, I really just watch cartoons now. So, I I actually for low stimulating things, I really like minuscule.

Uh, it's like a a YouTube short that's like French made and it's like spiders and flies and like bugs just very low

stimulation hanging around. Um,

>> sounds not not appealing, but uh, >> no, that's why it's so good because you're so overstimulated having kids that it's so mellow. You can be like, "Oh, I actually get to think a little

bit."

bit." >> You know, like, >> okay, >> you know, finding finding a little boredom and creativity. That's how you get creative. If you're constantly if

get creative. If you're constantly if it's like >> Coco Melon and Paw Patrol and you're like you can hear the beats in your head, like you can't do that. I'm not

gonna I can't do that to my kids.

>> Uh favorite recent product you've discovered that you love?

>> Cloud Co-work.

>> I mean I love Cloud Co-work. Sorry for

mentioning AI, but like I really only use a handful of products. So uh Cloud Co-Work is one of them and uh macroofactor for macro tracking. And uh I got a Whoop

this last year and I've lost almost 50 lbs just paying attention to my Whoop stats and like trying to sleep and you could tell I'm a pretty obsessive guy.

So data like still geeks me out a little bit on that. But uh those are the three products that I would use every day and and a little bit of Gemini too. Those

are the two in my opinion winning the race.

>> Do you have a favorite life motto that you find yourself coming back to in work or in life?

>> Always give more than you expect to receive. It's like a golden rule plus

receive. It's like a golden rule plus plus.

>> That's that's how networking works.

You don't you don't network with someone trying to take you say how can I help you? And that's a that's a principle

you? And that's a that's a principle from Shelini also, right? And uh

how to win friends and influence people, right? That's not why I do it. I'm just

right? That's not why I do it. I'm just

I'm just suggesting that's an area where you can read more on that.

>> Final question. Uh you you're starting a foundation, a nonprofit.

>> Yeah, I'm I'm working for or I I'm on the board of the Cody de Roof Foundation and that's in Bosezeman, Montana. And

what we do is um my son has cystic fibrosis and cystic fibrosis is a genetic condition. I'll actually talk a

genetic condition. I'll actually talk a little bit more about it in predetermined because his life was quote unquote predetermined. We were not

unquote predetermined. We were not really accepting that. Um, but in with our foundation, we help rural parts of Montana get access to the health care

that they need. And so they they got me with this. So like we we helped this

with this. So like we we helped this family, this this woman, she had three boys. This is a sad story, so bear with

boys. This is a sad story, so bear with me. So one of her boys, 29 years old,

me. So one of her boys, 29 years old, needed a lung transplant. This is what cystic fibrosis does. So made it to 29 is good. Life expectancy used to be 7 to

is good. Life expectancy used to be 7 to 10 years old. So made it to 29, needed a lung transplant, she couldn't afford it, and her son passed away. She had two

other boys with cystic fibrosis. And

then so her 27-year-old son, two years younger, needed a lung transplant. And

she actually found out that our agency existed in that that period. And we

funded the Lifellight to Denver Children's Hospital to get that life-saving surgery and saved her son's life. And

life. And that sounds like a great story. The part

that got me was that now the mama's feels all this guilt because she could have saved her son's life if she knew we existed.

And that part like I was in tears thinking about that. Um I did I've talked a little bit about my son's diagnosis like it's not defining our life but my wife and I prayed about this

and it was if it would happen to anyone it should happen to us because as soon as that happened I I made a handful of phone calls. I've I did all this

phone calls. I've I did all this networking to be selfish and build my career and do these things and and that give before you ask to receive philosophy. I've always kind of lived by

philosophy. I've always kind of lived by that underell overd deliver. And within

24 hours of his diagnosis, I had a phone call from the chief medical officer at Denver Children's Hospital at Stanford at uh I got a call from the FDA that said, "Don't worry, the son your son's medication is getting lowered to

oneyear-old and the triricft is going from six to two. So he may never experience a symptom in his life because this has changed now. So like I felt

just this immense blessing and support through that. So that's that foundation.

through that. So that's that foundation.

We we support these rural areas that don't have access to that healthcare.

And then I've also started conversations with the cystic fibrosis foundation which uh really helped funding. They

helped fund the life-saving medication that changes the life expectancy from 7 to 70 years old. Like they are expected to have full lives now. So, that's

something that I'm very passionate about.

>> Incredible. Oh, man. There's so many so many topics and directions we could have gone with this. Uh, Jacob,

>> I know I blew you out. I blew you out of the water, man. Sorry. I uh I monologue like nobody's business.

>> There is It's I've had I've had worse.

Um, okay. Where can folks find you online if they want to reach out, maybe follow up on some of this stuff? And how

can listeners be useful to you?

Listeners can be useful just by advocating for themselves. Rising tide

for everyone. That's important. Uh I

don't I guess I don't really have social media. I deleted LinkedIn. Uh the post I

media. I deleted LinkedIn. Uh the post I wrote about that kind of went viral on Substack. It's cool. I share I think I

Substack. It's cool. I share I think I shared that one with you. Uh I have execsandthe.com which yes is a play on sex in the city.

It's kind of explaining some of the things that uh people are afraid to talk about. So, Execs in the City is my

about. So, Execs in the City is my Substack and I write once a week on Thursday morning and I share little thoughts on what's happening.

Occasionally, I'll share case studies on what clients have done. I'll share

playbyplays and the actual scripts.

That's also where I have a free job search course. It's about eight hours

search course. It's about eight hours that I filmed. I used to sell it for like a grand and now I just give it away for free. That's also available on the

for free. That's also available on the YouTube, which is Execs in the City, which I have like a hundred subscribers, so don't expect a lot of content from me. I'm not I'm not pumping out video

me. I'm not I'm not pumping out video content all the time. Um, and then there's a a small paid tier if somebody wants to get discounts on coaching. They

also get access to Jacob GPT. Well, it's

another AI mentioned that's digitally trained on I think you have one too, right?

>> It's like trained on all my content.

Lennybot. Yeah. So, it's it's like a jigabot, which is a minor Lenny bot, >> right? Trained on my content. And um

>> right? Trained on my content. And um

then I do some additional case studies for them. Uh, and then my actual

for them. Uh, and then my actual business is thinkwarwood.com.

Uh, which just tells you outcomes that that we've been able to deliver. So, uh,

I'm not going to ask you for Instagram or anything like that. Just real simple.

Try to keep it Substack only. Really,

>> Jacob. This was awesome. Thank you so much for being here.

>> Thank you, Lenny. I appreciate the time today. And again, I was real giddy about

today. And again, I was real giddy about it. And your motto was to have fun. I

it. And your motto was to have fun. I

had a lot of fun today. Thank you.

>> That's right. Here we go. People don't

see this if they're waiting till the end of this podcast. I have this little pocket to show all the guests that our goal is to have fun. Uh, so Easter egg.

All right, Jacob, thank you so much.

Bye, everyone. Thank you so much for listening. If you found this valuable,

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