#115 – Tanay Kothari, Co-Founder & CEO of Wispr Flow: How a 27-Year-Old Founder Is Redefining Lea...

It is extremely important to make sure that you're treating people with respect in every step of the way. This is one of the things that I have to say. I wish I didn't have to, but this is not obvious

in a lot of situations. The second is you really need to spend time to understand how people would like to be treated, how they would like to be given feedback, how they would like to grow,

how they would like to be complimented.

So when there's a new person who joins my team who I'm managing directly or indirectly, this is the first thing I spend time with with them so that I can show up to them the way they would like

to be shown up to. It's basically like love languages but you do it for every one of your employees. Welcome back.

This is from Startup to Grownup. My name

is Alyssa Con and today I'm thrilled to welcome Té Cathari to the podcast. TA is

the co-founder and CEO of Whisper, the AI powered dictation company. He's also

a three-time founder who's been building products since he was 10 years old. TA

had a pretty dramatic journey with Whisper. It started as a piece of

Whisper. It started as a piece of hardware that you could speak to silently. That's right, speak to

silently. That's right, speak to silently. Although the technology

silently. Although the technology worked, TA realized the world was not ready for this and he made the painful decision to pivot the company to its current incarnation, AI speech dictation

that works elegantly on your computer and your iPhone. In this conversation, we talked about what it took to make that pivot, including the heartbreak of layoffs and what TA learned about

separating a big vision from the right next step. We also talked about his

next step. We also talked about his rather counterintuitive leadership practices and onboarding process. We

covered what it's like leading people who are older and more experienced than he is, hiring low ego people, and creating an environment of fast feedback. We also get into some real

feedback. We also get into some real talk about the personal side of the founder journey, the trade-offs, the pressure, imposttor syndrome, and why believes that in the end, the people you work with matter than anything else.

This is a deep and practical conversation with a founder who is truly wise beyond his years. So, please enjoy my fantastic conversation with Tana Cathari, co-founder and CEO of Whisper.

TA, welcome to the show. I'm so excited to have you.

Thanks for having me, Alyssa. It's great

to be here. I'm thrilled because as I told you, I am a fanatical user of your product, Whisper. So, we're going to

product, Whisper. So, we're going to talk all about that and how you got here. You're a threetime founder and

here. You're a threetime founder and you're now building Whisper Flow, an AI powered dictation software, but you're actually your first incarnation was like a hardware company. So, what were you trying to build and and what was the

moment that you realized you had to pivot? you know so January 2021 my

pivot? you know so January 2021 my co-founder Saj and I were talking about hey what are the most important problems in the world that nobody is solving at that point GPD3 had just come out right

this is before chat GPD and what we realized is you can actually start talking to your computers and they can understand you in a world where this is possible how do you make it so that

people can use voice everywhere and so we assumed somebody would build a good voice assistant and so what we decided to build was a way so you can use that

even when you're around anybody else.

And so we built a wearable device which you could speak to silently, which means you're not making a sound out loud. And

it would pick it up and it was the world's first thought to text device.

And so we decided to build this to make voice ubiquitous so you don't disturb others. You have privacy. And 3 years

others. You have privacy. And 3 years later, what we realized was, hey, we have this hardware. It works, but nobody until today has built a good voice

interface. You have Siri, you have

interface. You have Siri, you have Alexa. We know how both of those are.

Alexa. We know how both of those are.

And what we realized is this is the big problem that needs to be solved first before you can have any hardware that is voice first. And so that is what we

voice first. And so that is what we decided to build. And it really for me is building the foundation for every single kind of wearable technology that

will exist in 3 to 5 years from now. Cuz

the biggest thing that changes with that is they will be voice first than display first. And you need an extremely

first. And you need an extremely reliable high quality way to interact with them.

Yeah. I think that first of all that's so fascinating for so many reasons. Like

if I'm not mistaken, although there were problems with the product, your product actually worked that I could be thinking something and it would be somehow I guess transferred to either what the

page or to somebody else. I mean, that's like wild.

Yeah. If right now I'm just thinking like, "Hey, how are you doing?" It would just put that down on the screen or even say that out loud in your voice.

It was magic.

That is magic. Although kind of terrifying and very far-seeking. But

then I think it's amazing that you were like wait a minute no one has built this basic thing and I myself when whisper came out and I first started using it. I

myself felt like wait where has this been because I've been using the Apple notes app for a while. It's fine. It's

actually fine. It gets the job done. But

Whisper is so different because it really it can kind of interpret your meeting and it's clear that you're using a question mark or you want to speak in bullets or it's a new paragraph. I have

to say like why did it take if I may say so like why did it take so long if you will for that to come out for that kind of a thing to come out.

The problem and the solution is so obvious when you put it there you speak and it writes for you perfectly. The key

realization we had is hey people speak differently than they write. Like

speaking is more fluid longer sentences you go on rambling for a while. Writing

is structured to the point concise and also you write differently in different contexts. my messages to my brother

contexts. my messages to my brother sound very different than a formal professional email that I write even though it's the same human being writing it. And these were two key insights that

it. And these were two key insights that we took. And we realized that there's a

we took. And we realized that there's a kind of person who thinks about the user experience and designing those experiences very deeply. And there's a kind of person who works on all the core

machine learning models that is building that and those two people are often siloed in different teams within organizations. There's always an R&D arm

organizations. There's always an R&D arm that's working on it and there's always a product team that's working on something completely different. And I

think the biggest innovation we had from day zero was we made them the same person and that meant that we were always solving the most important problems which seemed so simple and

obvious in hindsight but nobody had kind of approached it from this very crossf functional way before.

Yeah. Wow. Well, I think that's really interesting. Just to go back again to

interesting. Just to go back again to your original product. You were building your original product and you had, I think, a team of like, I don't know, 40 or more people, very smart people, very eminent people, but then you had this

moment of realization. This is not the thing that's going to get us to where we want to be. We need to go back and build the AI dictation piece. And you had to lay off a whole bunch of people on the team. Obviously, that was like a bad

team. Obviously, that was like a bad news for everybody. And certainly, I'm I know that you yourself were heartbroken.

What specifically was that like? Can you

take us back to that moment that you realized you had to do that and the messaging you had to give?

Yeah. So, now we're in 2024, right?

Whisper is 40 people. Everybody's in

person and it's this extremely tight-knit team, right? I spent I personally spent a lot of time with every single one of them and their families. And in June was when we

families. And in June was when we realized we had this board meeting and we were talking about Whisper Pro, the hardware device, and then Whisper Flow, the software product in our in our board

deck. And at the end of it, one of our

deck. And at the end of it, one of our investors just remarked like, "It kind of feels like you're building two companies." And that was a very small

companies." And that was a very small off-hand remark, but that just stuck with me cuz I realized based on my personal actions, I was spending way more time with the software product and

I was way more bullish on that than I was with the hardware product going out right now. And that was a big, you know,

right now. And that was a big, you know, slap in the face moment for me and Sahed where to Sahed it was way more obvious before it was obvious for me that, hey, this is something that needs to be done.

And for a couple of weeks, I was trying to really hold on to this idea, right?

cuz when you're a founder of a company, the company becomes part of your identity. And killing the product felt

identity. And killing the product felt almost like killing a part of myself.

And so I was trying very hard to kind of keep a hold on it, not make it die, find some way to keep it alive. But every

single one of the options that we came up with would have just led us to build a sub-optimal company and not really hit the goal why we started this off in the first place. We were thinking about,

first place. We were thinking about, hey, what if we build this as a defense business? What if we build this as a

business? What if we build this as a healthcare business? What if we just

healthcare business? What if we just become like this R&D shop and we kind of build these things for other companies?

You know, the the major kind of nail in the coffin was Sahes and me just coming up and taking a good look at the reason of why we started the company in the first place was not to build silent

speech, was not to build hardware. The

reason we started the company in the first place was I hate people looking down on their phones like this all day long. And to me, if we wanted to get

long. And to me, if we wanted to get people off of that, it's not a screen time app that's going to do it. It's

going to be a fundamental transformation of what personal computing looks like.

And so for that, what you need to do is you need to get people from here to there, which is this new way of computing. And that is what we were

computing. And that is what we were really building towards. And if we decided to kill the hardware product and focus on the software product, we

actually still had a shot of making it there. And that was took us basically 6

there. And that was took us basically 6 weeks to come to that realization with a lot of certainty. And then there was a good amount of mourning that had

happened personally in that time. But

the hardest thing was yet to come cuz I had to tell this to my team. Now this is what was happening with me and SG, right? If you looked at the company, it

right? If you looked at the company, it was the time of highest morale. We were

6 months ahead of schedule. No R&D deep tech company 6 months ahead of schedule.

We had the best people in the world. We

had tenured professors who had left their universities to join us full-time.

We had people who would previously have managed Nobel Prize winners. And this

was the core team that was working at Whisper. And at that time, we were one

Whisper. And at that time, we were one of the hottest companies in the valley.

Investors were super happy, a lot of money in the bank. and to go to this team and tell them like hey you all have done nothing wrong but we decided that this is not the right thing for the

business to do this is not the right way we will win and we just want to be respectful to everybody's time was just almost shell shock to everybody I

personally I mean it it hurt everybody else a lot more than it did for me but I personally lost maybe 20 lb in those like 2 months I could barely

eat, barely spend time with family when I went back home. Maybe one of the hardest, definitely one of the hardest couple of months of my life cuz I did like all these folks. And you know,

breaking the news to them and then coming back the next day into this like big bustling office that used to be 40 people, now just six people around a

desk and getting this team back up to speed to build this new kind of company that we believe could really work out.

It was really important to me then to make sure everybody was well taken care of. So I made sure everybody is, you

of. So I made sure everybody is, you know, I spend as much time with those folks, making sure they have good jobs.

I'm able to provide all the referrals, recommendations, and all that I can. And

the redeeming thing now is I'm back in touch and close to a lot of people who are back with the whisper team them. I

thought they would hate me for life, but I'm very glad that was not the case. And

one of them even joined us back for this next phase of the company. M

so I was worried this whole time of did I treat the people well or not and just seeing them be back seeing them kind of smile and hug me when we meet again now

that's at least like one feeling that I have like heart is at peace that I did the best that I could for the people.

Yeah. I mean I do think that that's so obviously such an important part and it's hard to let's say stick that landing. I guess I'm curious what did

landing. I guess I'm curious what did you learn from that process because the truth is that one would never learn never do layoffs because sometimes layoffs have to happen right so I just

I'm curious how that changed you in the way you're kind of going forward as a leader in so many different ways I think the biggest thing that we learned while looking at this was the fact that a lot

of times when you're starting a company right you have a large vision of what you want to achieve and you mistake that large vision for also what you should

currently be working on. And so a lot of companies when you talk about the vision with the founders and CEOs, it's here's where the world is, here's where we want to go. And then most founders make the

to go. And then most founders make the mistake of building this immediately without realizing there's actually steps you need to take to get there. Because

just because you want something to happen and you force it upon people, it doesn't work that way. you need to kind of usher the world with you almost like a shepherd and take them with you

through this journey and that to me was the most nuanced realization that I had and so when we start thinking about whisper now we always think about it

with these phases with every single approach that we're doing so that one we're always grounded in reality two where we're not trying to bite to more than we can chew and so kind of an

example here is take the example of Tesla Right? Tesla did this well. Tesla

Tesla Right? Tesla did this well. Tesla

was like, "We want the world to have electric self-driving cars." You do not get there by building the whole thing once in the first go. No, you first take an existing car and you just put

batteries in it. Let's see if this works and people drive this thing. Oh, great.

People do. Great. Now, we'll build just an actual like full electric car and that's it. Now, we'll make it drive in

that's it. Now, we'll make it drive in one lane. Now, we'll let it switch

one lane. Now, we'll let it switch lanes. Now, we'll get it to run on a

lanes. Now, we'll get it to run on a highway. Now we'll do this, now we'll do

highway. Now we'll do this, now we'll do this, and so on, piece by piece, you're actually getting there. But a lot of companies did this the other way around.

And you see the number of Teslas you see in San Francisco versus any of these other cars. And you can kind of see who

other cars. And you can kind of see who has definitely been the person like leading the charge here overall. And so

those are the companies that I now look up to even though we're building a software product which is completely different, but the principle still stands. So the idea of really step by

stands. So the idea of really step by stepping people into kind of the vision that you see as opposed to one fell swoop, tada, here's that vision where people can't necessarily process that.

And honestly, techn technologically speaking, it may not even be possible yet. Like there has to be a a ground.

yet. Like there has to be a a ground.

You have to sort of break the ground ahead of you. It sounds like Yeah, I think that's really interesting, especially given you and your background. So let's get a little bit

background. So let's get a little bit into your background because I can understand why you sort of just assume that the world will bend to your world bend to your will because you started

building and learning to code when you were 9 or 10 years old. You stayed up all night. You got to listen to this

all night. You got to listen to this everybody. Every other night. He could

everybody. Every other night. He could

only code when his parents were asleep.

So he stayed up all night every other night to get around the sort of one-hour screen time rule that your parents had.

And let's just stop there. What the heck was driving you like a crazy person at that age?

I just wanted to prove people wrong.

I just So that was the that was the first driving force.

Yeah.

When this this 12th grader looked at me when I was asking him about how he's building apps and he was like, "Oh, you're too young for this. No one says

that to me." And so I wanted to one show this kid up, right? I'm 9 years old. Of

course I'm wenchful. And that was the first thing that drove me. But then when I put that first product in the hands of people, I was at a party and I saw saw this other kid use it and show it off to

everybody else.

And I saw the excitement. I saw the spark in the eyes. And I think at that moment moving forward, that was and has

been the primary thing driving me all these years. It's the moment when you

these years. It's the moment when you and I hopped on the call and you were just talking about how much you love the product. Like that is honestly what I

product. Like that is honestly what I live for. That is what makes me continue

live for. That is what makes me continue to work 18 20our days even today. That's

what makes me sacrifice a lot more in life cuz this delight that I just have the opportunity to bring to people is just insatiable.

It just like it just sounds like it's like an inner force that that is like for some reason that is a spark for you.

Yeah. tell us more about what that means that you're sacrificing because I think that people when they when they start a startup they don't always realize kind of the sacrifices they're making and the

choices they're making. So talk more about how you kind of perceive the trade-offs you're making and the sacrifices you're making as you're on this whisper journey.

Yeah, founding a startup, especially a ventureback startup, it's honestly not something I wish upon anybody. You know,

when you think about life, there's a ton of things that that matter to you. You

care a lot about your friends being there for them. You care a lot about having a really nice and loving and healthy relationship. You care about

healthy relationship. You care about spending time with your parents. You

care about having hobbies and traveling the world and getting a lot of experiences. And when you have a

experiences. And when you have a startup, it's basically you're always responsible for this baby of yours, right? That is always at the verge of

right? That is always at the verge of dying, right? You could be the hottest

dying, right? You could be the hottest company in the world and you'll still be like, "Oh, this company can die." Even

if you, you know, open Aai is one of the most well-known companies in the world at this point. And Sam Alman in his recent interview was like, "I'm stressed. Like, my whole routine is

stressed. Like, my whole routine is going gone for a toss. I can't work out properly. Like 3 days a week I used to

properly. Like 3 days a week I used to do is not happening anymore because yes, you're always stressed. And more than that, there are so many lives that depend on you. the kind of work

environment you create. Imagine you make this person feel very empowered. They

feel like they're doing incredible work.

Imagine the energy they go back home with. Imagine how they're shrinking up

with. Imagine how they're shrinking up back home and they're feeling like proud with themselves. How they have high

with themselves. How they have high energy to spend time with their kid and their spouses and all of that versus imagine if you create a stressful environment for them. Imagine what

happens when they go home then. Maybe

they're mad. Maybe that anger comes out on their kids. And so you're not affecting just the employees in your company. You are pretty directly

company. You are pretty directly responsible for a lot of their external families as well. And the thing is you can say like oh this was this other manager's fault or whatever. But at the

end of the day everything is your fault as the founder of the company and everybody joined here because of you and you're just carrying that that burden.

So this is kind of like what is the piece here, right? And so when you're kind of sitting at 10 p.m. about to go to bed and you're like, "Oh, there's one

thing I can do that can just be good for the company." You're not going to bed.

the company." You're not going to bed.

You're staying up another 4 or 5 hours until 3:00 a.m. in the morning. You

know, you have to get up at 7:00 for your next batch of meetings. But you

know, this thing is more important than like 3 hours of sleep. You know, this is more important than going to do a workout. Like last year I went to the

workout. Like last year I went to the gym a total of three times. For

reference, I have averaged 6 days a week in the gym for the 10 years before that.

Last year I was just gone, right?

Cuz there was so much to always do in the company. Working out never came top

the company. Working out never came top of my mind. My health was the thing I sacrificed the most cuz I was like, I can't sacrifice the time that I have with my fiance, right? We're just

setting up a new home, a new family, a new life together. I can't sacrifice the time with my parents and so the friends that I'm really close to just one or two

days a month I actually get the time to see them and when I see you know them posting all the trips they're going on all the bachelor parties and all the things that I am saying no to because I

have these responsibility on my shoulders it eats at you a bit but you know this is the these are the decisions you made yourself and that is just the

cost you have to bear for deciding to start a company and being responsible for all of this.

Did you have to come to that like like any normal person would still have like you chose this for yourself of course you're successful that's fantastic but it does then require these sacrifices

and trade-offs. Was there ever a point

and trade-offs. Was there ever a point that you felt kind of resentful like oh I can't believe I'm doing this or were you just like no I' I've I understood. I

must say to Nate like you're ridiculously mature. You're 25, right?

ridiculously mature. You're 25, right?

27.

Oh, 27. Sorry. 27.

I got I got another two years of older than me.

That's right. So, he got a little more mature. But like as a 27year-old, it's

mature. But like as a 27year-old, it's just a very mature way of looking at the world. How did you come to that?

world. How did you come to that?

I think part of it was requirements of the job. I cannot not have an extremely

the job. I cannot not have an extremely high level of emotional maturity, right?

That'll make for a worse company. Uh

it's just as important as working out.

So, that was something I had to I had to personally work on. And I think the second thing was this is something I had

known about myself since 9th grade that one I'm not emotionally mature. two, I

need to be way more emotionally mature because there are some people who I saw who had those traits and I could just see how much more effective they were

with their not effective just like they were better friends, better partners.

They were better like work colleagues to to work with. And I had a couple of role models in my life who I really really look up to. And one of them actually was

my fiance when we started dating. I was

14. I had the emotional maturity of a rock and she actually trained me and helped me get to the point where I could

start expressing my emotions. I could

point out what emotions I was feeling and I could start to show up for people in ways in which they wanted to. So that

was my first first boot camp in being more emotionally mature. The second was part of my my first internship which became my first startup at age 14 or 15

was this guy Arjun. He and I decided to start a company together. And it came from all the small things. The first

time I was heading out he was like okay by and I just shook his hand and he was like no that's not how you do it. Got to

give a hug. And so I gave him an awkward side hug, right? Cuz I'm this like very awkward, nerdy, introverted like 15year-old kid. And he was like, "Th is

15year-old kid. And he was like, "Th is not how you hug." So for the next 10 minutes, he was like, "Okay, T, you're going to like these like five people here. You can all hug them properly.

here. You can all hug them properly.

You're going to get used to it." Like

like stuff you don't expect, right?

A hugging clinic.

Yeah. No, hugging clinic. And then after that he was like okay T you're going to shadow my calls to see how I do small talk initially and build rapport with people when I'm meeting them for the first time because he was talking to VCs

and founders and all of that. So he made me sit beside him through all of that.

Then he was like okay T you're running this call I was 16 years old like like running a call with his like LPs who had invested in his fund. I was getting pitches from startups who were doing

that and all this. So again, good amount of teaching throwing me off on the deep end, but I don't think without mentors like this and also just just knowing that, hey, this is one thing I want to

be better at, I would have gotten to this point.

I first of all, as always, love of a good woman, right? Let's start there.

But also, I think it's so powerful that you kind of re you saw like, oh, this is kind of the way I want to be. And so

then you were open to that mentoring and melding. other people. Yeah, I think

melding. other people. Yeah, I think that's very powerful and I'm sure it's stood in goodstead and and I know that now so throughout your startup career and then now you manage people who are older and more experienced than you and

I'm sure this emotional maturity has to come into play. What's that like? And

what have you learned about managing people who are more experienced and older than you?

That and I think most things in life is very simple. It's not easy, but it's

very simple. It's not easy, but it's very simple. And the first thing that I

very simple. And the first thing that I learned about it is it is extremely important to make sure that you're treating people with respect in every step of the way. This is one of the

things that I have to say. I wish I didn't have to, but this is not obvious in a lot of situations. The second is you really need to spend time to understand how people would like to be

treated, how they would like to be given feedback, how they would like to grow, how they would like to be complimented.

So when there's a new person who joins my team who I'm managing directly or indirectly, this is the first thing I spend time with with them so that I can show up to them the way they would like

to be shown up to. It's basically like love languages, but you do it for every one of your employees.

Yeah.

And this goes for young, old, all of them. And then what I try to do a lot as

them. And then what I try to do a lot as a leader is like, yes, I have veto power on everything. I can tell people like,

on everything. I can tell people like, we're not doing it this way, we're doing this other way. And I can use that, but that one is not scalable because people

haven't learned why you did the things you did. And two, they lose a little bit

you did. And two, they lose a little bit of respect for you. cuz you have to rely on your authority instead of your

reasoning or persuading abilities to get work done. And so instead, what I try to

work done. And so instead, what I try to do with everything that we we do is showing people why I make decisions the way I do and getting people on board

with those decisions. Now, that doesn't happen 100% of the time, of course, at which point you disagree and commit. But

the fact that they get this from me time in again and a lot of things go down to like, hey, I don't think you're making this decision talking with somebody

because you're incompetent or wrong or inexperienced. You and I have different

inexperienced. You and I have different beliefs in the world. So, let's talk about that first and align on that. So,

you understand where I'm coming from. I

understand where you're coming from. And

so we can make a decision together that we both feel happy about by first aligning on hey are we talking about the same things that are important.

Could you give us a specific example of where that where you would use that technique and exactly what they said and exactly what you said to come to this alignment?

Yeah of course. So let's take the example of my CMO right incredibly talented man. He's been doing this for

talented man. He's been doing this for the last 25 years. He was CMO and CEO of multiple companies before. And we

brought him on when we were 10 people.

And so he joined and now he's helped scale the company to 50 people and kind of hyperrowth period. And so he was spending about 60 70% of his time on

making sure our life cycle marketing is well on making sure our website is properly optimized on making sure our performance marketing engines were running well and all of the things that

you would generally consider like great hygiene for a marketing or I was instead telling him like okay we need to do these things to go viral on Twitter and

Instagram and we need to scale up these channels And to him initially it was like no T like we need to care about these core hygiene marketing things and you know these other things are other

channels and all that work and in my side I was like if we do the things that every other company does we're not going to have 10x outcomes like we want to and so this was creating a friction because

we were inherently working off of different very different basis and so what we did then and this is actually a very recent exercise this is as of a month ago was I I told him like why don't you put

down the different things that you think we should do as a company and why and I'll put down that list and that actually highlighted a couple of very

key things. The very key things that he

key things. The very key things that he highlighted were one I was really going off of, hey, if we want to be a company like the number of companies that have

gone from 1 to 100 million in revenue in under 18 months, you can count on fingers of one hand. If we want to be another one of those, we need to do things that other companies are not

doing. And so I was bringing up things

doing. And so I was bringing up things like that for him. He would always push back on it because I wouldn't mention how important kind of the base hygiene is. And so he would think I don't care

is. And so he would think I don't care about it. I only care about these things

about it. I only care about these things that are extreme. And so to him I was the CEO who was like go more viral do more viral things. And he was like no T we have to do these basic things also.

But the thing that surprised him was in my list I had put all of those things as important. I had just said these don't

important. I had just said these don't require executive involvement cuz our performance marketing team is fantastic, right? They're doing a great job. If you

right? They're doing a great job. If you

and I are in there, maybe it goes from 80% to 95% in effectiveness. That

doesn't measurably move the business.

But hey, in these other things, if we do these well and you and I jump in, we have the ability to 10x. And so, I actually think you and I should spend our time in these kind of higher risk,

higher reward pursuits. And that's when he realized I wasn't we were talking about something completely different.

And then what we did was we basically took both of our priorities. We went

through wherever there was something that one of us thought was important but the other one didn't. We had discussions on all of them. And now we have a consistent prioritization and ways to

make decision for everything in the marketing org that we have both aligned on. And so now our discussions never

on. And so now our discussions never have to spend be kind of deep in those conflicts cuz we know we have the same decision-m framework. Now we can spend

decision-m framework. Now we can spend our times way more productively. And the

biggest thing this has had in actual effect is our velocity of conversation has literally gone up by 4x. The number

of bullets we could go through in a single conversation has shot through the roof. We're talking about 16 17

roof. We're talking about 16 17 different topics in a 30-minute meeting and actually coming to an alignment and agreement on every single one of them because we have such a strong foundation set up.

I love it because you got on the same page philosophically. But wasn't that

page philosophically. But wasn't that challenging to do because again I I'm picturing somebody with 25 years of experience saying this is the way marketing works and this is the way marketing works today you wouldn't

understand because you haven't done marketing before. So I'm sure that you

marketing before. So I'm sure that you brought smart points of view. Obviously,

I'm sure he brought up Smart's points of view. Didn't you have tension at all in

view. Didn't you have tension at all in those initial conversations or even just defensiveness of like, hey, I've been doing this 25 years. Why are you why are you questioning me? That's normal.

That is normal. And it did come up. And

I think the key key thing I view this from, and this has shifted a bit on how I now lead and manage manage people when when new people are brought into the company, is like if you're a great designer, right, you know how to do

great design. What you may not know how

great design. What you may not know how to do is great design at whisper because there's certain ways in which we make decisions here. There are certain things

decisions here. There are certain things that are important to the company and it's my job to tell you what those are so that you can combine it with your other skill sets and be the best person

for this company. And that's the biggest thing I I realized as well cuz the other thing that happened like where I I'll tell you the wrong way to do this. The

wrong way to do this is either you believe nobody is great at their jobs and you need to micromanage everybody.

Then people don't feel valued. The other

wrong way is you expect people are great at their jobs. You expect people are going to be automatically great at the job you hired them for and then they don't meet your expectations and you're like, "Wow, I'm sad. I thought you were

a great designer." But you never told them how to properly function in your company. And so that little nuance and

company. And so that little nuance and it's it's a very small detail but when you learn that now whenever a new person joins the team I spend 30 minutes a day

for the first 2 to 3 weeks with them where I go through like tell me about the things that you think are important for us to do. Tell me about the decisions you made today and we go through and basically audit all of them

and I'm like okay this is how I would have done it. This is the other thing that's important for it cuz that is what I want them to learn. And I come up with this like totally upfront. You are an incredibly good designer. I know cuz we

brought you on and we interviewed thousands of people for this. Now I want you to be the best designer for Whisper.

So I'm just going to help teach you the core decision-m process. It's part of the onboarding. And a lot of the people

the onboarding. And a lot of the people on our team are extremely senior, right?

20 years of experience and so on. And

this I found works really well with them. because I also pose this as

them. because I also pose this as respecting their skills and that I'm on the same side as them.

Yeah. You've said so many things. I have

to like unpack all of them. It's so

powerful. How do you know they're going to be that kind of person when you bring them on board? Do you look for that kind of because you can be the most respectful person in the world and some

people just don't like that. You know,

like get out of my short CEO, young founder. I'm the adult supervision.

founder. I'm the adult supervision.

That's just like normal. And I don't mean that in in a derogatory way. I

mean, I think that's like actually a little bit of a meme. Also, they have had a lot of experience and been successful. So, how do you find how do

successful. So, how do you find how do you make sure that you're hiring the person who's going to enjoy that and really embrace that in the hiring process?

That's a fantastic question. So, we have one of our behavioral criteria for all our hires. You could call it low ego or

our hires. You could call it low ego or coachability. We've been going back and

coachability. We've been going back and forth on them. And there's one question that gets to the root of this, which is when you talk to them about a specific thing they've done in the past, you need to ask them, "How could you have done

this better?" And the person who was

this better?" And the person who was coachable with low ego often also have the self-reflection to give you a very good and thought out answer. Then if

they say, "Oh, this was like the best thing we've ever done. Couldn't have

been done better." No, everything can be done better. And so that's there there's

done better. And so that's there there's a right answer to this question and there's a wrong answer to this question.

But this helps us get that. And as a company, you may or may not want this, but we care a lot about hiring low ego personalities within the company. That's

just how Sahage and I work. That's just

how everybody in the company works. And

so we we optimize for that.

Yeah. Another thing that you do, which I think is a very interesting and innovative technique, it's adjacent to what you just talked about is that I think you sit with your employees while they do their work. So you actually

spend like maybe a full day, whatever it is, and watch the employees do their work and shadow them in order to talk through maybe where some friction is, how you can be helpful also maybe you

have other ideas how they can do it.

Where did is that first of all is it true you do that and where did that start and what have you gotten out of that?

So I do do that. I do do that a decent amount with every single team in the company one by one. So I'm a very hard guy to please, right? I have a I I have

very high expectations from everybody in the company and one of the jobs that I have for myself is I need everybody to execute at the bar I expect them to. Now

how do you do that? Option one is I just tell them do better. Some people it might work well but some people are just like but how? Like if you just tell me

do 2x better like do I spend 2x the amount of time working on it? Well, then

my family life is shot and then I'm burnt out or do I like ship worse quality work faster or like what do you want me to do? And so what I realized is

whenever I used to kind of try to motivate people that way for most people it wouldn't work out cuz people are already working really hard. They're

already at least from their perspective trying to do the best they can. And so

then I was like okay why don't I dive in? And so I'm not going to tell you

in? And so I'm not going to tell you like do 2x better. I'm going to tell you, I want you to do 2x better and I'm going to jump in the trenches with you and we're figure we're going to figure

out how. And then when we do that, a lot

out how. And then when we do that, a lot of things bubble up. Because the other thing I realized is my mentality with things is hey, anything is possible. If

you want to change this thing up, if we want to like build a new system, if you want to get somebody else, like we can just make things happen. And so that is the angle I approach this with. And I

just sit and I see them work because I can't give them advice without knowing the reality of what their day-to-day looks like, without knowing the reality of what are the obstacles, what are the blockers. I'll give you a very a very

blockers. I'll give you a very a very specific example. I was sitting beside

specific example. I was sitting beside one of my engineers. He was walking me through his work and every 10 minutes somebody else on the team would ping him to ask a question, right? It was

somebody on the customer support team, somebody on the sales team like, "Hey, how does this work? Hey, how does that work? Can you tell me like what the

work? Can you tell me like what the price is for like these people in these regions?" And he's going and figuring

regions?" And he's going and figuring out that in the codebase. And I was like, wait, this is terrible. You can do at max 10 minutes of deep work before you get interrupted. How do you get

anything done? And so what we did was we

anything done? And so what we did was we actually set up a a cloud code instance for the company that was connected to our codebase. And we did a session that

our codebase. And we did a session that onboarded every single person in the company on top of it. And now everybody has to go through that first before they ping an engineer. And so now engineers

get about two hours of deep work done before they need to respond to a query.

It's not perfect, but it's so much better than what they had before. And

this was just something where you're just in the zone. You just don't see at times. And so this is the kind of very

times. And so this is the kind of very simple product mindset that I also have.

This is how also I I build product and I sit beside my users to see what are the pain points and then go solve those. But

you just apply the same thing within the company. And so I think if I did not do

company. And so I think if I did not do this and I was trying to build a company and make hard level decisions without knowing what's important to people and individuals, I would just make worse

decisions. Yeah. Also, what an

decisions. Yeah. Also, what an incredible innovation because you're seeing with your eyes that your engineer and your engineers are getting pinged.

So, not only do you save them time and letting them kind of get into flow state and deep work, but also you create kind of your own automated sort of support

like like support system as a that which is a great innovation as a result of this, you know, studying and shadowing you're doing.

Yeah, that could probably be a company of its own. There's so many things within Whisper that people that could be companies of that order.

Yeah, I'm sure that's true. I'm sure

that's true. which is kind of why and I I have to say I'm a little blown away that you mentioned you have 50 people.

Yeah.

Yeah. I'm blown away by the fact that you have 50 people, but that is kind of what is going on right now. Tell me how you personally think about the fact that you're like growing like a rocket ship.

You have 50 people. Are you do you think you're going to add a whole bunch more people? Do you think No, with AI and

people? Do you think No, with AI and kind of the processes we're building, we're going to be very moderate in the way we build. What's different about startups today with a result of sort of what you're able to do with AI and how

do you see that in terms of the size of your company?

So what this has made incredibly clear is there are certain things where you definitely need a human for and there are certain things where you do not.

There are set of automatable tasks and we will keep scaling. We'll likely two to 3x in size by the end of this year.

But the kind of people that we're going to be hiring are going to be very different. Right? Let's take one

different. Right? Let's take one example. Let's take customer support as

example. Let's take customer support as an example. So some background. Whisper

an example. So some background. Whisper

is roughly 10xing its user base every 5 months.

The number of users also equally increases the number of tickets. Also

equally increases the customer support team you need to have. And so to handle our millions and tens of millions of users, we need hundreds of people on our support staff 3 years ago. But today

that's one thing when you look at it and it's like okay this is actually you know you can define the work you can define the playbooks you can run the playbooks

well and actually turns out AI today if you spend time building this right can actually perform at 90th percentile of your average support. It's like okay

fantastic. So that is the first thing

fantastic. So that is the first thing we're going to spend time automating. So

5 months ago, we had five support reps who were managing our entire user base and they were basically at capacity. Now

we've 10xed since then. We have the same five reps and they have twice the amount of free time on their hands and they're using it to build and train our AI systems even better cuz 75% of our

support tickets are managed by AI. And

here's the thing, we realized that people did not know that they were AI agents. We had called them, they were

agents. We had called them, they were called like Whisper, Whisper Flow AI support agent. People thought it was

support agent. People thought it was Whisperflow AI support agent. And so

they're like, "Oh, thank you. You're

like the best support team ever and all of that." And we're like, "Why are

of that." And we're like, "Why are people saying this to an AI?" And we turned out nobody knew that it was an AI responding. And we spent months and

responding. And we spent months and months making sure this this AI is like smart and helpful and empathetic and drives things in the way that we would want it to that I would personally want

to if I was doing this myself.

And this is one huge area where we don't need to scale anymore. So the who are the people who I'm bringing onto my support team? It is the most senior and

support team? It is the most senior and entrepreneurial per people you can imagine who will be basically managing

an army of 70 AI support agents, right?

You don't need those low-level workers as much anymore as you need managers who can manage these people. Let's take an example of engineering. We don't hire junior engineers anymore. I would hire

somebody who's young who has the kind of like entrepreneurial like mindset overall. But apart from that, we have

overall. But apart from that, we have staff engineers who then are managing a team of five claude agents. And so we're launching our Android app soon. And that

is being built by one person who is managing these six claents who he delegates work to every couple of hours.

They do this work and his job is to review, manage quality, define what needs to be done, take higher level important decisions. And so that is

important decisions. And so that is going to be the kind of people that we hire who can make these decisions, have good taste, have good decision-m abilities overall. And then the workers

abilities overall. And then the workers who just execute on these tasks and who historically have been kind of entry-level jobs, that is just kind of gone.

Well, welcome to the future everybody.

Where we are. It's terrifying.

So, how do you personally kind of reflect on that considering that it really is terrifying? And then what advice do you have for, you know, people in college right now or even in high school about what this new future means

for them and what they should do? So,

first of all, how do you kind of reflect on that? And then what advice do you

on that? And then what advice do you have? I think the first thing is it's

have? I think the first thing is it's going to be such a rude awakening especially for everybody in college today cuz they made those decisions on what they're going to be spending their four years doing based on a completely

different world that no longer exists today. And for people who are there the

today. And for people who are there the biggest thing I would say is so so in in college people would take that as like training grounds to learn things and then after that hey I'm going to do an

entry- level job and actually learn how to do this work. Companies aren't going to hire for that anymore. So I would basically say that hey this this entry levelvel learning and training period

you had that is actually now completely on you and that is what you really need to spend time doing in college because here's the thing people haven't stopped

hiring they're just hiring for a different kind of people and you need to match that and the biggest thing that gets you to match that is hey go pick

something and just get deeply obsessed about it build taste learn enough so you can make good decisions. Cuz if you have that, then you can have 10x leverage and

do everything else. If you don't learn that, then you're kind of stuck because nobody else is going to give you that opportunity to. I was on a panel at MIT

opportunity to. I was on a panel at MIT talking about AI and one of the insights was that what you need to build right now is an entrepreneurial mindset and that's really what you're talking about.

self-study, teaching yourself, going deep on something on your own, just on your own time and on your own vition and I think that's such an important lesson and I can understand you know if if I

would give someone advice go deep on something that makes sense but build taste is something else you said what's your advice for someone to build taste what do you mean by that so a lot of people think taste is

something that you're just born with you just have either good taste or bad taste and that's kind of it but taste is something that I think is one of the skills that you can just genuinely

build. And the way you build it is the

build. And the way you build it is the same way you learn any other skill which is by trying something and then getting immediate feedback.

Let's take you're writing stories, right? You're writing short stories. You

right? You're writing short stories. You

could decide to spend a year writing a bunch of stories and then you just, you know, put it in a book and you publish it. you likely have like learned a

it. you likely have like learned a little bit if you're kind of reflecting yourself what that is. But the first thing you do is, hey, you read your own stories and a year later and just be

like, hey, what do I like? What do I not like? And then go off of that. Or what

like? And then go off of that. Or what

you could do is with every single story, you share it with an audience. You see

what they like, what they dislike, you get that feedback, and then you do again. And that has now taught you how

again. And that has now taught you how to write good stories that people engage with. And that is now you can call

with. And that is now you can call taste. The same thing literally with

taste. The same thing literally with food. The same thing with building

food. The same thing with building products. Like the reason Whisper Flow

products. Like the reason Whisper Flow feels so good and delightful and people call it one of the most tasteful products designed in 2025 is because I

built garbage for 10 years and I know I know now what good products should feel like because I have done all the wrong things over the years. And so now when a wrong decision is made, it's so obvious

to me the moment I see it.

And that is I think something again just repetition and obsession gets you there.

But once people realize that, hey, it actually teaches you taste, it completely changes how passionate they are about diving in.

Yeah, I think that's really good advice.

I mean, you could you could really apply that to anything. You said food, but you could also say poetry or plays. You

could also say coding, building product.

How do you folks at Whisper get fast feedback cycles?

So, we basically run the company continuously like it's a two person startup. Say we're building a new thing.

startup. Say we're building a new thing.

This is this is happening with a couple of internal products right now. We first

put together a group of 50 people who desperately want this, right?

Outsiders.

Outsiders.

Okay. How do you find them?

Right now, it's easier because they have messaged us to our support channels or messaged me that, hey, I would love to get this feature. I was like, great, let me go find all those people who have wanted this thing that we're starting to build right now. And we put them in an

iMessage group chat or a WhatsApp group chat. And then we build the simplest

chat. And then we build the simplest version of this thing, just give it to you like, hey, does this thing solve the job cuz it does what it what you wanted it to, but then they give more feedback.

Hey, it's a little slow. Hey, it's this I like, you know, this time it made a mistake, so I stopped using it. It's

like, great, keep that feedback coming.

And we ship new versions almost twice a day, if not more frequently. And these

people are very engaged. Now, here's a couple of things that happen. First, if

these people are not engaged, we kill the whole project immediately cuz like you said you wanted it, now we gave it to you and you don't care. That means we should also not care. Second, if we see

heightened emotions, right? The moment

it crashes once, people are mad. The

moment it works once, they're like, "Oh my god, this is the best thing in the world." Those heightened emotions are

world." Those heightened emotions are what I personally look for because I know that is what are signs of solving an important problem for people. Once I

see that, then I was like, this is going to be a banger and a massive money-making machine. We got to just

money-making machine. We got to just double down on this and make this an incredible experience for people. There

is usually three or four of these running at any given point in time within the company. And these are built very closely with all of these people.

And these people also feel really special, right? They're actually getting

special, right? They're actually getting to shape a product that is going to be used by millions of people and these people are ones that I I personally care a lot about and you know we give them

what like lifetime whisper flow for free all of that cuz to me like the product wouldn't have existed with these people.

Yeah. They're super fans obviously.

Yeah.

Yeah. And so you look for heightened emotions. That's really interesting. And

emotions. That's really interesting. And

then you sort of just do these sort of feedback loops. And I guess I'm going to

feedback loops. And I guess I'm going to come back to, by the way, you can hopefully tell that I mind your LinkedIn and No. Yeah.

No. Yeah.

Couldn't you tell? Yeah.

You've done a good amount of homework.

Yeah. I'm going to ask you also, how did you learn to write on LinkedIn? But

before I go there, one of the things you talked about was that your NPS score I love such a good hook for LinkedIn. Our

NPS score dropped dramatically and that was the best thing that could have happened to us. So tell that story about what happened and what you learned from it. NPS is net promoter score for those

it. NPS is net promoter score for those of you who don't know and really it's a sort of like the view of how people are viewing your your product and it's either high which is good or low sadly which is bad but according to today it

was like we got a bad NPS grade and it was a the best thing that happened how come so NPS we get from asking people how likely are you to recommend this to a friend right and if you're like a 10 fantastic that means you love the

product zero I'm never telling anybody about this thing it's like okay we we need to do better our NPS score was 70 which is incredibly high amazing for any product out there and it was 70

for many a while and then we saw it one day drop to 35 now a lot of alarm bells ringing it's like what happened and the thing we realized is hey we had gotten

very excited about this new product that instead of doing this exact thing that I told you hey we should like do fast iterations with a couple of people like small group no we we'd put half our

company on it because we thought hey this is going to be the next big thing and Hey, dictation isn't a good solved point. That's fine. What happened was

point. That's fine. What happened was there were a lot of feedback from users and issues that of course come up as you're building software that we just did not have to time to pay attention to. The velocity that people were seeing

to. The velocity that people were seeing from that product was lower because of course we moved half of our people to work on the new thing. And that just very clearly reflected in how people

viewed the product, what they thought was the quality of experience that they were getting. And to me, the best things

were getting. And to me, the best things in the world are ones that teach me a really good lesson very quickly. And the

one that this taught me was everybody thinks like, hey, I'm going to build this company and I'm going to we're going to ship a bunch of products and it's going to be incredible. We're going

to have a whole product suite. But if

you look at the best companies out there, they don't have a product suite.

They have one product that is incredible and might have a few things on the side with it. That is because building just

with it. That is because building just one product really really well is incredibly hard. Take a look at Slack.

incredibly hard. Take a look at Slack.

Only Slack is fantastic. They write

canvases and a few other things and it's it's okay. Huddles is okay. If they were

it's okay. Huddles is okay. If they were like, "Okay, we're going to go build a Zoom competitor without like properly thinking about the resource allocation for it." You bet Slack was going to

for it." You bet Slack was going to start seeing a lot of bugs because you just took the people who were maintaining this thing. And so that was the big realization that we had is is actually like no we are not going to

ship a new product every 3 months. What

we are going to do is make sure that this core thing that we have that people love. We're able to maintain to the

love. We're able to maintain to the highest bar of quality possible. Keep

scaling this thing. And whenever we are building anything new, this thing really needs to prove itself. And it cannot take away resources from the core thing that we're working on. Which is why this

kind of testing philosophy that I talked about right now we're building new things from scratch. That is where this came out of which is hey no it's just one engineer working on this with a core group of people and just keep iterating

on it until you know this is extremely important and then we can do this and again keep it close to the core product so it doesn't take away a lot of resources from that and so it it changed

my mental model of what I prioritized how we think about shipping new things and overall just the product road map which imagine if we didn't see that signal for a while and we went further

down that road and learned it six months later, it would be so much harder to undo.

Totally true. Or if you were like, "Oh, I'm sure it's just a a month. I'm sure

it's just like a little downgrade for some reason, right?" Like not to really look into what happened. Is that also how you decided to have I think you have two person teams that are launching something. Is that also part of your

something. Is that also part of your kind of lean fast feedback loop iteration concept? Tell us about that

iteration concept? Tell us about that because you have a lot of very interesting management processes. I

would say that you know are very they're just very unusual and I'm curious about how you learned them but I'll talk about that that twoerson teams launching products.

Yes. So we have our core product team right that's focusing on this this experience and then we have a concepts team and this team is just you know people cycle in and out of this but it's

just always two people one is likely a PM or a designer the other one's an engineer and they're given one specific we call it jobs to be done but basically

like a use case or a product experience we want to solve for and they just keep experimenting and solving that. So

here's the good thing. It needs a very different mindset than the core product team does cuz the core product team like cares a lot about reliability. It needs

to work all the time. It needs to work at scales of millions of users. And

there's a lot of things that are like the post PMF scaling era of a company that you really need to focus on. But

this concept team has a very separate mindset. So the other great thing that

mindset. So the other great thing that happened by kind of moving that away was we always have this mini skunk works like engine that is always working, always building new things, always never

taking things for granted and you have this kind of core scaling engine that's going on as well. This is what a lot of companies end up doing, you know, when they're a thousand, 5,000 people, they

have a small like skunk works like team that they do and we realize like that's too late. No, we need this right now cuz

too late. No, we need this right now cuz this is a muscle that you learn really well as a startup and then you just lose somewhere along

the way and that's when you stop seeing that level of innovation and all and that excitement that you have at an early stage company and I just don't want that to die.

I love it. So it's like both intentional but also you see the results of it and it's so true. Startups very quickly calcify.

Mhm. That's a beautiful word. I love

that.

Yeah, it's it's just the truth. And then

it's like how do we kind of rec re that muscle? But you're saying we just don't

muscle? But you're saying we just don't want to lose that. We don't want it to atrophy. I love that today. So I'm not

atrophy. I love that today. So I'm not an Instagram girl as much. Maybe that'll

change in the future. I'm a LinkedIn girl. My 107,000 followers strong and

girl. My 107,000 followers strong and strong and mighty. And I That's right.

And I'm like looking at your LinkedIn and I'm like what the heck? How did a startup founder like you learn to copyright so well? who's helping you?

How are you kind of how did you think about your positioning? Because building

a personal brand is such an important part that some people don't realize.

What's your been your journey about kind of building your personal brand online?

The first thing to answer that is why why LinkedIn? Why choose to invest time

why LinkedIn? Why choose to invest time in here? Cuz I have limited time in

in here? Cuz I have limited time in life, right? And so the thing we

life, right? And so the thing we realized early days with whisper is when we ask people where did you hear about the product? A lot of them heard about

the product? A lot of them heard about it on LinkedIn cuz the main kinds of people who use Whisper are white collar professionals, right? you're a manager,

professionals, right? you're a manager, executive designer engineer lawyer etc. And all these people hang out on LinkedIn together. So like interesting.

LinkedIn together. So like interesting.

I never thought of LinkedIn as a great organic channel for us. But okay, this is good. And the second thing I realized

is good. And the second thing I realized was whenever I posted, I I would only post for our big launches. We would get a lot of talent applying through LinkedIn and we would see the massive

spurt in extremely highquality people reaching out to join the company. I just

wanted to juice this engine. a lot more because I knew this was working. And so

the question is like okay, how what's important? How do we get this to work?

important? How do we get this to work?

And so I went and I picked a few people who I really respected whose LinkedIn I wanted mine to be like and then I was looking at them both at hey what are they writing about? Who are the people

who are responding to them in the comments? What are people writing in the

comments? What are people writing in the comments? Right? Cuz every post is not

comments? Right? Cuz every post is not just the post itself or the message you're delivering, but it's actually a conversation that you're starting. So

that's that's one like learning about it from looking at others. The second thing is how does the LinkedIn algorithm work and that's the thing I dove into. So

here's what you see all the social media feeds they care about one showing you content from your following and then they rank that based on some metrics but like okay if a post is doing well people

are engaging with it they will show it to you. Fantastic. The next hardest

to you. Fantastic. The next hardest thing if you want to grow your following is you need to understand what is the kind of content that LinkedIn is showing you from people you don't follow. And if

you scroll through LinkedIn, it's very clear to see somebody you follow commented on X. And so what you realize is the thing that LinkedIn really optimizes for is comments. This is

different from Instagram, different from Twitter. I can go into rabbit holes of

Twitter. I can go into rabbit holes of each of them, but this is really about understanding the specific algorithm for this thing. And so what I got was this

this thing. And so what I got was this is the kind of content that works.

LinkedIn really wants you to click on that see more button for the long post.

So everything beside the see more has a single job to make you click the see more button. Which means if your title

more button. Which means if your title says guess how much money we raised and an image is saying $50 million, no one is going to click on your see more because there is no suspense. There is

nothing in it for people to kind of hook on and and spend more time with your post. And so these are all the things

post. And so these are all the things that started to become obvious as I was just studying this. And basically for me all of social media is not an art, it's a science. you can break it out into

a science. you can break it out into very specific rules that you need to follow. And if you follow these rules,

follow. And if you follow these rules, the algorithms will like you more cuz at the end of the day on the other side is also a scientific algorithm that is running to optimize your your post to other people. So it's kind of opening

other people. So it's kind of opening the black box to learn that and then getting your content to be there. And if

you actually like or it's a waste of time, but if somebody were to like go through and read my older post, you could see the the evolution of it not hitting for a while until I started to find like, okay, this is the kind of

content that my audience loves to engage with. These are the things they look up

with. These are the things they look up to me for. These are the kinds of things that I can uniquely share with the world. And it's actually very different

world. And it's actually very different for different people. There's some

people on LinkedIn who just write unhinched content like this is what I learned from B2B SAS about something something and that wouldn't work for me because my audience cares a lot more

about the insightful thoughtful things that I have to share with them or the wins that I want to share with them cuz there's a lot of people rooting for me and so that's what I put out on my LinkedIn but that was a a learning

experience and now I'm helping my co-founder build his and for him people have very different expectations he is seen as a technical leader and a

technical visionary and so his content is going to be more focused that way. So

it's a lot of these learnings and then iterations. That's why I post every

iterations. That's why I post every single day because this to me is continuous learning. And even though

continuous learning. And even though right now, you know, my LinkedIn is incredible, brings in a lot of impressions, all of that, it's still something that I never take for granted.

And it's always with every post I'm looking at what's going on to recalibrate and continue basically delivering the same like more value week after week.

I love it. The same analytical approach.

It's so helpful. And also I think it takes your ego out of it. People are

like, "Oh, people don't like me or whatever." You're like, "No, it's just

whatever." You're like, "No, it's just an algorithm. Get over it.

an algorithm. Get over it.

It's just an algorithm."

Although when when people don't respond to me sometimes I'm like, "Nobody cares about what I have to say."

It happens.

That's right. That's right. We're just

human today. Just a few more questions.

I could talk to you forever, but just a few more questions. Have you ever experienced imposttor syndrome or severe self-doubt?

When when do I not? It's every single day. No. Um, genuinely though, I think

day. No. Um, genuinely though, I think part of this is I never want to be overconfident. I'm absolutely terrified

overconfident. I'm absolutely terrified of being overconfident. And I always hold myself to an incredibly high bar that I often can't personally reach

either. And every day, every other day,

either. And every day, every other day, thoughts come to my mind. Am I

like what?

Am I good enough? Am I extremely incompetent and everybody's just going to figure it out very soon? And they

just don't know it yet or why am I qualified to do these things? And the

one thing that kind of gets me out of it is realizing that we are all just people. And what I need to think about

people. And what I need to think about life today is, hey, here's this opportunity that I have in my hands.

what is the most I can do with this opportunity today and just leave it like that. Don't try to make it too much

that. Don't try to make it too much about, you know, my ego or my capabilities and all of that. That's one

thing that helps me get out of the rut, but the rut exists.

Yeah, you're not alone, obviously. Any

other sort of suggestions for founders about how to handle imposter syndrome?

I wish I had more suggestions, but I haven't figured it out too well myself either. You know, it it really helps

either. You know, it it really helps when you have at least one person who can give you positive encouragement. I

think this is especially true for CEOs and founders cuz nobody in my company is going to come and tell me like, "Oh, Tana, you did a great job with this cuz it's like, oh, the CEO doesn't need

compliments." CEO needs compliments, you

compliments." CEO needs compliments, you know, like they're like, "Oh, like am I going to be dumb if I tell the founder like, "Hey, you did a great job at X cuz you're you're supposed to be and and so

on." And so it's kind of like part of

on." And so it's kind of like part of the job. Also, most of the work that you

the job. Also, most of the work that you do like other people can't see. And so

there's hard things to kind of latch on to cuz you're working on long time scales, right? If your company didn't

scales, right? If your company didn't die for another year, like you did a great job. The one thing that helped me

great job. The one thing that helped me was opening up about this to my co-founder and it's like, yeah, dude.

kind of feel underappreciated a lot of the time like in the company generally because one like nobody knows what I do and two is like there's some level of

this this this corporate barrier that inadvertently comes up and so the great thing that's happened is he now he heard me and now he is my biggest cheerleader

in the company for all those things and and that makes it better that makes it better just somebody I can fully open up to with all of this and they always cheer you back so yeah My main advice for founders is try

to find somebody like that for you. Make

life so much easier.

Very powerful. So true. Today, what do you wish you had known earlier on your journey?

That is just a company. It's just a company. It's just a product. You

company. It's just a product. You

personally are so much more than that.

Yes, you should take it very seriously, but not make it your whole identity for the benefit of you and everybody working for you and the whole company and

everybody else. Now that I know that, I

everybody else. Now that I know that, I can do some more specific things to kind of hedge myself against it.

What can you do now that you know that?

If the company is not going well, that doesn't mean that you suck. You start to look at it a little more objectively. If

you Yeah. And I think that is the the biggest day-to-day thing is being able to detach from it. And one big thing that lets me do this is always make sure there's at least one thing outside of

work that you're doing on a consistent basis. So there's at least something

basis. So there's at least something else that you your identity isn't 100% on your company. Maybe it's going to the gym and you're hitting a new PR. Maybe

you're just playing a game, right? And

you see yourself progress in that game.

Could be anything. But that is one of the hedges that keeps you from just having 100% of your emotions being managed by the company. Because what you really need to optimize for is when when

everything is going poorly, what do you do then?

Totally. What advice do you have for other founders as they embark on their journeys to grow into leaders?

Your product changes, your market changes, but the people you work with don't. And so if there is something that

don't. And so if there is something that you're spending time investing in, make it that more than anything else.

Amazing. TA, you're amazing. Your

product is amazing. Everyone should go download it right now. Whisper Flow.

I've used it so much. I'm personally a power user and as I said to you at the beginning of our discussion, a fan girl.

So, thank you for joining me today. It

was so great to talk to you and so great to hear your insights.

Alyssa, thanks so much for the insightful questions. I really, really

insightful questions. I really, really enjoyed this.

Thanks for listening to From Startup to Grown-Up. If you like what you heard,

Grown-Up. If you like what you heard, give it a review on Apple Podcast so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a

line through my website, alyssakone.com.