[S03E03] Breaking It, Fixing It, Building It: The Mindset Behind Startup Success with Kevin Henrikson

In this episode of No Hacks Podcast, host Sani chats with Kevin Henrikson, an entrepreneur and engineering leader whose journey began on a pig farm. Kevin co-founded Acompli, sold it to Microsoft in just 18 months, and helped turn it into Outlook Mobile. He explains how to move fast without sacrificing quality, why your first-time user experience (“Kleenex user”) is so crucial, and how to adopt an “advisor” mindset inside big companies. If you’re looking to master the MVP philosophy, leverage AI for higher productivity, and cultivate a curiosity-driven mindset, this is the episode for you.

KEY TAKEAWAYS:

1. Ship Early, Learn Fast
   • “If everyone loves your MVP, you shipped too late.”
2. Kleenex Users Matter
   • You only get one shot at a first impression—make it count.
3. Advisor Mode Post-Acquisition
   • Offer ideas without bulldozing existing culture.
4. AI as a ‘First Pass’
   • Use automation to handle repetitive or initial drafts, then refine with human expertise.

MEMORABLE QUOTES:

• “If everyone loves your MVP, you shipped too late.”
• “Your first-time user is like a Kleenex—you only get that fresh perspective once.”
• “Be an advisor, not a disruptor, when you join a big company.”

SHOW NOTES & TIMESTAMPS:

• [00:00:00] Introduction
• [00:00:10] Kevin’s Background
• [00:00:22] Early Career in Tech
• [00:02:49] Rapid Decision-Making & Mindset
• [00:05:01] MVP Philosophy & “Kleenex Users”
• [00:08:21] Starting vs. Scaling
• [00:11:56] The Acompli Story
• [00:14:42] Post-Acquisition Life
• [00:20:14] AI, Automation & the Future
• [00:27:23] Rapid-Fire Q&A
• [00:33:00] Final Insights & Wrap-Up
• [00:43:42] End of Episode

CALL TO ACTION:

• Connect with Kevin: https://www.linkedin.com/in/kevinhenrikson/
• Subscribe to Kevin's newsletter (Founder Mode): https://foundermode.kit.com/
• Share Your Takeaway: Tag @nohackspod with your favorite insight!

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Transcript

[00:00:00] Sani: Welcome to No Hacks podcast. Today I'm joined by Kevin Henrikson, entrepreneur, investor, and engineering leader who's built and scaled teams in Microsoft, Instacart and Acompli. Kevin is a master at scaling the smart way, making rapid decisions and building businesses that last. In this episodes we talked about product market fit, automation in startups, and the biggest mistakes founders make when scaling.

If you're a builder founder or just love hearing from top tech minds, this one is for you.


Kevin, welcome to No Hacks. Such a pleasure to have you on.

[00:00:31] Kevin: Awesome, man. Good to see you. I think it's, uh, it's been crazy. We were just saying before the show, like it's been, uh, yeah. 15, 16 years now instead of be able to do a

[00:00:39] Sani: 16 years since we connected, we never met in person. Tell me about your background, like you, your engineering background, uh, piloting, uh, productivity, all that stuff.

But tell me about your career and professional background.

[00:00:51] Kevin: I grew up on a pig farm in Central California. Uh, went to school at UCLA in la. Uh, you know, when in high school I always loved working on cars and sort of like, uh, we had like a drafting kind of architecture class and, and. You know, so definitely liked building and you know, spend more time breaking things and building things, but you build it, take it apart, that kind of classic model.

And one of the teachers is you should be a mechanical engineer. And I was like, I've never heard of that. I'm like, that sounds cool. And so literally checked that box on my college applications, uh, got accepted to UCLA in mechanical engineering and started there working on. You know, what was early maths chemistry, all the kind of classic general education stuff.

But then the biggest thing was you had internet, right? Like, and growing up I always had this like dial up modem, kind of slow internet and just really wasn't really internet. Um, but at the dorms we could plug in, we had ethernet and it was fast and like, wow, like that was crazy. You could start to see computers and the days that, you know, swapping music and things like that in the early days.

But that to me was like, man, I really want to do this computer thing. And so just became fascinated with building computers, working on computers, um, at a time when, you know, kind of the internet was really kicking off there in the late nineties. Um, went to change my major and they're like, no, no, no, you need to have straight A's.

Like computer science is very impacted. Everybody wants. And I was like, all right, that's fine. I'll just finish my degree. But started doing all my internships and working on engineering. Um. And really, it wasn't even like, it was like pretty simple stuff, right? Self-taught like, hey, how do you connect a website database, PHP, uh, Apache, you know, setting up, you know, Linux servers and things like that.

And, uh, just really experimenting, um, and kind of stumbled into that. Worked at a small startup in la, uh, ended up going outta business, kind of the classic.com crash. Uh, got them. Moved to Silicon Valley 25, I guess years ago now, 26 years ago. Um, and sort of have been up here ever since. I think the, you know, typically doing the small company, sell it to big company, do another small company, start, you know, sell it to big company kind of round.

And so have a good sort of arc of like, um, you know, seeing what it's like to have nothing and start, and then, you know, sort of seeing that work. You know, seeing it get acquired and then when you're in the larger company sort of running really big teams and sort of that, uh, sort of shifting your mindset and learning along the way of what does it take to be successful in each of those environments?

I think, um, ha has kind of been the, you know, the last two decades.

[00:03:17] Sani: But is that the same mindset from break things apart and put 'em back together from,

[00:03:22] Kevin: is, I think, and I think part of it's like when you zoom out, you're like, well, what's the big vision? What are you going after? You know, how do you create shareholder value? And shareholder value looks very different in like a startup with two people, uh, in a garage kind of model, or three. And then, you know, scaling up to, you know, hundreds of people on an engineering team at Microsoft or Instacart.

Um. But many times when you get to that big vision, even with a big team, you have to kind of go down and say, what is the actual problem? Right? What is the like core little issue that's broken and how do you deeply obsess over some small thing? 'cause that becomes the most important thing. Um, and then sort of being able to zoom in and zoom out, um, you know, at some level learned it on the farm, right?

You know, you're riding a go-kart or riding a little motorbike around you race it, do some jumps, you break it, you're like, okay. Do we need to get out the welder or do we need to get, to get, you know, take apart the carburetor 'cause we got dirt in it. Right. You end up looking at different pieces to, to figure that

[00:04:15] Sani: Yeah, I love that. And I talk about mindset often on this podcast with almost all of the guests because. Basically all we're doing is optimization. You, you, you, you take a company, you optimize it, you build it, you, you grow. It, it, it's all about making parts of it better. One at a time or a few at a time, or all of them at a time, if that's even possible.

I like that. It all goes back to that mindset because that's the soft skill, that if you don't have that, I want to, I want to figure out how this can be better and bigger and, and like whatever else. Nothing's gonna happen. Nothing's gonna, nothing's gonna happen.

[00:04:47] Kevin: Optimism is like a key thing, so I think it's optimism and curiosity, right? You have to imagine like you're, you're riding this go-kart or you're riding this motorbike and. You wreck the thing or you're working on a website or you're working on a chunk of code or a business and it's broken you, you have to mentally be optimistic that it's gonna work.

And then just be curious of like, well, why didn't it work before? What could I try? Is there something different? Is it just more effort of the same thing? Or is there some new way that I can approach it? Um, but, but definitely wake up every day on all these problems and being like, wow, I'm still excited to work on the problem.

I'm still excited to see where it goes. Um. You know, when you run into problems, those just are opportunities to go figure them out. It's, it's just creative problem solving

[00:05:30] Sani: That's a great quote. Um, so let's talk about rapid decision making and execution because yeah, I've known you for 16 years now, which sounds insane. There are not a lot of people I've known for 16 years that are not from back home in Serbia. I. And I know that you are all about, let's just make a decision right now.

Let's move on and let's execute, and then let's change direction when we need to. Let's just figure it out. How do you stay disciplined in that approach? Uh, to problem solving and, and pattern recognition?

[00:05:59] Kevin: Yeah, I mean, you know, some people will say it's probably just as much of a feature as it is a bug, right? I have this sort of anxiety of like wanting to do the next thing and pushing sometimes to a fault. Um, and it allows me to get distracted easily, but it also allows me to say, Hey, let's just make a decision to move on.

Because at some level, you know, I finish my meals quickly because I'm excited to do the thing after the meal. And that's annoying. Like, you know, my brother lives in Europe as you know, and, and it's like, this is, and as you have your whole life and, and this notion of slow eating and, and the, and, and the pace is, is very different from like, you know, they always say like, Hey, the crazy American comes to Europe and then like the crazy American with like.

Anxiety or aggression or whatever you want to call it. I have, then you go and put that in Europe, it's like even more of a oil and water type mix. And so to me internally, like that's sort of the clock that's running is I'm excited to go do the next thing, um, to a fault. Right? And so that pushes me to make quick decisions 'cause like I'll wanna work on something else.

But when you zoom back and kind of think about it and why has it worked and why has it, I think been a more of a feature than a bug is that a lot of times. If you think back one year, five year, 10 years of something where you were obsessing over a problem, and it doesn't matter, honestly, like most things don't matter when you run it out five, 10 years.

And especially in technology where things are changing at this crazy rate, it, it doesn't matter, like the thing that you're worried about now. Like that website, that company, that thing, that product won't exist 'cause it will have, you know, version one is so different from version five or 10. And so to me it's.

It's, there's very few one-way doors, right? Where you go through, you're like, oh, that, that didn't work. Let's go back and do it again. Right? And so I think to me, now that I've seen that pattern enough. And yeah, the number of vacations that I can think where I'm in the hotel room telling the family to chill out 'cause I've gotta do this big thing.

I remember working on this one about page trying to center the fricking graphics on the team page. Dude, that company went bankrupt like a couple months later. Like, and so like yet I ignored walking in Central Park in New York with my family. 'cause I'm like, and so like now I'm like, man, make the decision.

Move on. And more than likely you'll get new information sometimes in an hour, but most times in a week.

[00:08:11] Sani: That, that's a great point. And, and a lot of times, like you said, with that about page, it will not even matter like six months from now, it, it will not matter. Also, building something and we, we've been building stuff together, uh, products together. Your version one, no one cares, like it's going to be so different compared to your version two, even a let alone version five, and.

Further, like no one cares, just ship it. And one I'll, I'll use one quote that I I got from you is if everyone says they love your MVP, you're fucked up. Like you waited for way too long and, and this, uh, decision should be made in my opinion. I, I agree on that as well. So, um,

[00:08:49] Kevin: Reid Hoffman always says, right, if you're not embarrassed with your version one, like, you know, you would, you ship, you would ship too late. I think there's also this version of like. You just, there's so many things you don't know, right? And, uh, you're working in your own head space, in your own brain or in the team's head space.

Typically, like when it gets to market or gets to users, you're gonna learn that something else is more important than anything else. You've worried about it. It's probably something in many cases you've never even thought or discussed. And that is what, how can you quickly go learn? What that thing is, is what I try to like push for

[00:09:20] Sani: That's a really good point, but Saudi State, you say you want to not think about the above page. You want to not think about those things that will not matter. In that form, in, in, in a week even. How do you stay disciplined to that approach?

[00:09:35] Kevin: I, I think so. It's two. So I think one is ha setting yourself a high enough bar or a goal, or being curious or optimistic about the big event. You're like, Hey, I'm trying to get to this launch. I'm trying to get to the next milestone. I. And reminding yourself that this small thing may have to be done.

You may need to do an about page 'cause you're gonna go, you need it to have something or, or you're embarrassed with 'cause you don't have something. But it's also like if you look at the ultimate thing you want to achieve on that next milestone, is that piece gonna matter? Or is there something that matters more?

And so constantly kind of going back and we talk about this a lot, like, okay, we don't have this particular thing polished and done. You're like, yeah, yeah, but is it good enough? To get there, or are we working on the website when like the onboarding screwed up? Like let's go fix the onboarding because that's where people are hitting a wall today.

Let's go work on that and not worry about the website because for whatever reason they're getting past the website and they're clicking sign up. Let's work with the people that are in front of us that are ready to give it. There was two analogies that we used to talk about when we were testing products, like one is this notion of the Kleenex user.

Like people get to be their first time user only once. So once you use a Kleenex, you can't like use it again and be like, it's the same, it's very different. Like it's been an impressioned. Um, and so the idea that when people come through the first time, the feedback that they give you is very, very, uh, different than if they're gonna come third, fourth, fifth time.

Like they get kind of bug lined. They get used to it. They kind of learn the trap of like how to go through it. Um, and so you want to really extract the most amount of insights from that specific use cases when people come through for the first time, and use that as an opportunity to go fix it, right?

And I think that's something that, you know, you want to be zoomed in on that, but then when you zoom out and say, Hey, what's the vision? Or is this even the most important thing for the next milestone? Whether that's a fundraising thing, whether that's a launch, whether that's, you know, Hey, I'm trying to get my first 10, first user first, a hundred, first thousand type of thing.

[00:11:39] Sani: Also, and I found this approach helps. If you are trying to make something perfect, you're not gonna make it perfect. But if you just, if I spend six more hours, this will be perfect. Hell no. Like there's no way you're gonna make it perfect. You, you know, you know nothing about what your users need with that feature and how they want it to be.

So just ship it and listen. Yeah, that there's a Kleenex. But if you're just testing with a few users to, and you get feedback, Hey, this clearly should be different. When the stakes are low, it's better to, to just adjust early than to try to spend like six months building something without showing it to anyone.

And then. You got slap in the face and, and, and it, it's just not good. But yeah, the Kleenex analogy, I never heard that one. That, that's really good. That, that, that's a great one. You said there were two, what's the other one?

[00:12:24] Kevin: I think the o, the other one is just, just this, the vision of like, you know, once people come through and they're using it, like how do you get away from like the minutia of fixing a specific thing versus like, what is the big next milestone? Then making sure that you're working on the most important thing for that big milestone, which many times it's just too easy to get distracted into some detail.

And whether that's polishing a detail or a bug that you're worried about or a thing fixing, it's like, man, after you spent so much time on it, you need to zoom back and be like, Hey, is this the actual most important thing I should be working on? Um, I think that helps, you know, sort of help you

[00:12:58] Sani: That's a good point.

[00:12:58] Kevin: to kind of reset what you're focusing on.

And whether that's resetting in a given day or a given work session, you

[00:13:04] Sani: So you've, you've, you've built and scaled, uh, quite a few companies. Which one's more difficult?

[00:13:13] Kevin: Yeah. I, I still think starting from scratch is harder, right? Because I, I think it's frustrating right? At times. 'cause you don't know what you don't know and, and what, you know, it's deciding what to do, deciding that that's important enough to enough people and kind of like, I, I think that's harder. Um, it's definitely less, uh. Less straightforward. When when you're scaling, it's pretty clear usually what's broken. It's not always clear how to fix it. It, but it's pretty clear what's broken. Like, hey, this, what, what is the, what is the bottleneck? Right? You know, at Instacart during the pandemic, it was like, you know how, how do we take more orders tomorrow than we took today?

And what is the reason for that? Oh, we didn't have enough shoppers. The website, you know, wasn't loading as fast as it needed to be. Oh, we ran out of inventory. That store was closed. I don't know, but like you could always pretty much fi figure out what the bottleneck was and now you, how do you fix, it's another problem, but.

Figuring out where that scale limit is usually pretty straightforward. Um, where I think at least there, you know exactly what to work on, typically where, or if you have a, you know, a big team and something's growing or hiring challenges or you're having like a cultural mismatch or something, again, you can kind of smell or see the issue pretty quickly how to fix it.

Sometimes they're very hard to fix. Um. But when you're starting from scratch in the white, you know, it's like the writer's block. You're like, I don't know what to write, I don't know where I am. You start to question, uh, a lot of things.

[00:14:39] Sani: That, that's a great one. I never thought about it this way, but yeah, you have your task ahead of you when you're scaling it, you know exactly where the bottleneck is. Like you said, with, with starting, you don't even know where the bottle is in, in some cases and, and yeah, you need to figure out a lot of stuff.

Uh, so just so you don't get too comfortable, we have rapid fire questions. Now, before we get into deep dive on sustainability versus cutting corners and smart scaling, which is what you excel at. Five questions, just run through them please. What's the best piece of career advice you ever got?

[00:15:11] Kevin: Uh, be curious.

[00:15:13] Sani: Love that.

Who was it? If you can share

[00:15:17] Kevin: Probably like an auto shop teacher or something. It was like, 'cause he was just like, because I was like, Hey, how do you, how does this work? Or does this work? And he's like, dude, you gotta stay curious. And

[00:15:24] Sani: let me share, let me share a story I have with you when I started back in 2009 OD desks and I, I would ask you that that was my first online project, as you know, first time working online, I was asking you questions and you sent me a link to let me Google that for you page with the answer.

And I haven't asked a stupid question. I, I, I've been curious since, and I've been sending that page for a long time. Well, not anymore. I, I dunno if it's around anymore, but

[00:15:48] Kevin: Need like a can. Let me chat GBT that for you right now.

[00:15:51] Sani: Basically Yes. That, that, that's, that's the thing. That is the thing. So that, you know, you need to have that mindset. Don't wait for an answer to come, just find it.

Because with the internet, even in 2009, you could find anything. 2025. Come on. Just be curious. I love that. If you were not in tech, what would you be doing?

[00:16:09] Kevin: Farming, man. I, I, I, and growing up on a farm was kind of dope. Like there's always this gentleman's farmer sort of still inside me of like, just chilling, you know, going out and feeding the pigs. And, uh, yeah, there's a, there's a, there's a, again, an, an unlimited number of problems when you live on a farm and things to go solve.

And so I think, uh, you know, again, some are easy, some are hard, uh, and so it maps a lot back to

[00:16:30] Sani: It's a more peaceful life as well. It's, it's a lot more chill. Yeah. What's the one thing you're currently learning?

[00:16:38] Kevin: Uh, I'm, I'm trying to do some, a lot more multi-agent stuff and so I think we, we've all become like incredibly good, you know, searching Google. I thought I was the best at searching Google for many years. Right. You know, or whatever. And then I think, uh, I, I think I've become pretty good at prompting various LLMs and chat or you know, or cloud or Gemini or whatever.

Pick your one. Or gr Now I then have been playing with Grok three a bunch. In the last 24 hours. But I think to me it's that idea of like, I have so many questions when I'm not at a computer or not at my phone that I want to ask and how can I create higher level frameworks or problems that I can give to multiple agents that, you know, my, my dream right now is to sort of.

We have a handful of agents in our companies and what we're doing, but is how can I give it some of the bigger prompts? And then every day check into the, check in with them like a board of directors or every week check in with them to see what things they've learned, give them direction. Just like I would give feedback to a real team.

Um, and there's a bunch of code, no code, a bunch of ways to approach this. Um. For various reasons, most of them don't achieve what I want, which is like, hey, I want to, you know, I have lots of things I wanna learn or, or be curious about, and I want to basically give those to a, to a swarm of agents to go work on, um, where I'm not having to prompt every step or I'm not having to like see it just kind of like blindly loop over the last prompt I gave it.

And so, yeah, slightly longer answer,

[00:18:07] Sani: Super interesting. No, no, no, no. No problem. What is one quality every founder should have?

[00:18:14] Kevin: Uh, yeah. I mean, I wanna say like passion or resilience, but I think that it's just this, it grit. Like there's, you know, a bunch of words for it, but, uh, yeah, I mean, you gotta want it, man, and you got, you gotta be, you know, you gotta have that sense of urgency, but also like the sense of urgency to where you're going.

Right? I, I think my quote in my high school yearbook was some version of like. Um, if you don't know where you're going, you're not gonna get there. And, uh, so you've gotta pick a direction and, and a, and then, and then you get to, you know, so you get to pick the direction and then you get to sort of like wake up every morning and decide on the velocity.

And I think that ability to sort of like, I have like this insane, like, sort of aggressive drive and so it's, um, yeah, I, I like the velocity part of it, but for me. When I see founders that are like, man, they have a direction or a passion, but not working hard, you know? And again, it's always varies, like depends on the space,

[00:19:05] Sani: There's a, there's a quote, a similar quote that I heard. I, I, I forget who it was, but when you want it more than you need it, like, that's when magic starts to happen. When you really are, have that psycho mindset, I'm gonna get this no matter what. And you can live without it. Like you, you're not like you.

Life depends on it. But you, you decided this is, I mean, you know, I'm a basketball freak and we talked about basketball. What Kobe had in Kobe in Mamba mentality like that. That kind of, he's crazy, but that's just what he was wired like and like he'll get his no matter what, when, if you have that, like dude, it's happening.

Favorite trick to maintain consistency in your life.

[00:19:44] Kevin: I mean, lately it's been by the calendar like, you know, a dumb thing. But sort of this year we. We'd set goals with each other and the team. And I think one of the things that I built is this kind of perfect calendar. So my EAs and I team up and, uh, you know, I literally have my sleep blocked out. And so, um, forcing hey to know that like that thing is scheduled when I should be asleep and it, and you know, it sort of moves when I, swift time zones and things like that.

Um, and so for me it's like if you can get a good eight hours of sleep. Then you can try to build your day and look at your week. Like when I look at a, you know, look at the week and say, Hey, are the things that we're doing this week or that we've worked on where I wanna spend my time and energy? Um, then it's great.

And if it's not, then we try to make a change. And so for me that's for at least personally, that's how I get consistency, you know, very calendar driven, but also like using the calendar as sort of a tool to sort of say, Hey, is the energy, you know, you're spending it the way you want to be spending it.

[00:20:43] Sani: Having a system and sleeping as like those two. Okay. Let's talk about, let's talk about scaling smart. I, I mean, this is something that I really wanna ask you about and there are, you know, there are many ways to move fast. Sometimes moving fast will not get you where you wanna go. It'll just get you somewhere faster.

So what are. You know, some, some keys when you're trying to be sustainable versus just cutting corners in the way you move.

[00:21:10] Kevin: Yeah, and I think this, when you're scaling at all, and I get this answer's changed, right? Like the kind of things that we were doing in the early two thousands to scale, you know, buying servers and how do you, you know, get things ordered ahead of time and supply chain, and then sort of in the, you know. 20, you know, kind of pre covid days, you know, hiring the valley was really a big thing.

And how do you hire and how do you build pipelines for hiring lots of people and like really high quality people through a, through a funnel. And then I think today I'm much more obsessed with like, what can a couple people do with the right tools? Um, a lot of AI and the way you scale there is really thinking about the things you're working on more directly because.

A lot of things that used to be hard five years ago, um, are not hard today. And so I think, um, you know, just like it was silly to buy servers, you know, 10 years ago, where in 20 years ago, that was the only way to do it. I think today, you know, 10 years ago, five years ago, it was really important to hire a really large team, be able to scale and understand, you know, how it cost to build a team and how do you sort of arrange a really top team now that that's different.

Um, and so I think for me. The framework for scaling is the same, right? What is the thing that I, what is the thing I want to do more of? How do I get more of that? I think the resources and the building blocks of how we do things today in 2025 has dramatically changed even, you know, from 23 to 24 to 25, just as we've seen sort of the change in how things are built.

Um, and it's also what I'm the most excited about for, you know, the next year, the next two years is where. We're seeing such a raft evol, um, evolve in like how resources are managed and how, and how sort of teams come together and what does it even mean to be a team or a company, um, or an entity in, in, in this world.

[00:23:02] Sani: Do you think that will be completely different in five years than, than it is now? What it means to be a company?

[00:23:07] Kevin: Yeah, because I think the, the, the things that you really deeply needed to like start a company, start a startup, start a project. Becoming easier and easier at levels that are unprecedented and, and the types of things that are like, oh, we're no longer gonna need that. Like, who would've thought like, you know, you can go to Atlas for $500 and create a company in a two days.

Right. I think, uh, one of our companies I created, like I was in Dubai on vacation at four in the morning. My wife woke up, she's hungry. She's like, Hey, let's order a hamburger. And I was like, oh dude. Like, okay, this is cool Room service 24 7. And then I was, I'm like, man, I wanna start this company. And literally did it in Atlas in Dubai with the thing KYC, all the like docs through Zoom like this, where that's like.

Dude, like the number of times to drive to the lawyer's office to meet, to get paperworks, to get notary, to go all that stuff virtualized. And so to me, like that was several years ago now, um, was kind of eyeopening. And now we're seeing that with huge amounts of resources and work where, you know, AI's either doing it or there's a service that, you know, uses AI or something behind the scenes where you can replace that.

And, um, that just continues to evolve. And so I think, um. A lot of what's gonna happen in the future is you're gonna have an idea

[00:24:26] Sani: Mm-hmm.

[00:24:26] Kevin: or you're gonna have an ask, and you're gonna be able to kind of prompt your way through that, whether that's through a service or through, you know, somebody that's helping you with the prompts.

In a way that, you know, everything is virtualized, I guess is another way to look at it. Where in the old days, like, hey, we virtualized servers, we moved that to the cloud, we virtualized lawyers, we virtualized, you know, setting up a company. We've now virtualized the human and the last kind of piece of that puzzle that, you know, it was one thing to kind of be on the internet and we're no longer having to walk down Main Street to buy a cup of coffee.

Or to, you know, uh, transact in business. We, the internet made a lot of that. You know, sort of EE whatever, the etailer kind of push. Um, now we're seeing this, you know, kind of e-business, if you want to call it, go to some, a new level where, you know, there's like arguably e consciousness, right?

[00:25:12] Sani: So what does the world look like if anyone? There's no skills gap and resource gap. It's almost non-existent or getting close to non-existent at this

[00:25:21] Kevin: I think it's non-existent. No, I think for anybody, any skill you are missing, you can literally get pretty damn good at it just by asking chat, GBT, like how do I learn this skill?

[00:25:31] Sani: That's an excellent way to put it. So what does that mean for the future? If everyone can have a business that is functional, let's not say successful, but functional? Isn't that noise at that point, like what is, is it more difficult to build and scale and grow your own business?

[00:25:48] Kevin: Yeah, so I think if we look back in history when productivity is increased. Typically two things happen. So one, people have more time, and when people have more time, they can choose to do that. You know, the old days used to spend, you know, 15, 20 hours of your day, you know, between getting food and fetching things.

So now I, I click a button and DoorDash brings it, right? If you, you know, fast forward all the way to the day, um, or delivery, if you're in a different country, you know, it doesn't offer doors. But I think the next piece of that is like, so people are gonna get more time back. A small percentage of people.

Are gonna spend that time working on the next thing, doing more things. You know, kind of think about it, investing that productivity. A lot of people are gonna find entertainment. So live events like going out and spending time with friends and family. So I do think there's going to be a new class of sort of approaching the world where it's like, hey, the business is running, or there is a way that this thing is working and I'm controlling some resource.

And what is that resource? Right? We can debate whether that's energy or thought. Or, um, creativity and I'm able to get a lot of time back myself to spend on entertainment or to spend as I choose. And so I think if you look at, like the app store is a great example, right? For all of the productivity apps and like get work done, go work out apps, what is there actually more of time wasting apps, right?

Just going and looking at things, games. Most people when given extra time will, will choose leisure, will choose entertainment. And so I think. There's also an opportunity in that to go build new forms of entertainment and new forms of leisure that, you know, longer travel, like much more, like longer adventures, like longer games.

It's not like the casual game where you just have 10 minutes on the subway getting to work. It's like, no, no. What's the casual game that like you have all week off?

[00:27:46] Sani: so the. Playing field might be different, but the game is pretty much staying the same.

[00:27:50] Kevin: yeah, I think so.

[00:27:51] Sani: I like. That's a great answer. Uh, now let's talk of all of this in mind. Your scaling smart principles, your, your approach to productivity and scaling. Tell me about the journey of building a accompli and I mean, it became Outlook Mobile.

I mean, I remember that was like 10 years ago now.

[00:28:09] Kevin: Yeah, it's

[00:28:09] Sani: I remember when it

[00:28:10] Kevin: for the 10 year anniversary, I think was just of launching Outlook was, uh, January 29th. And so just, uh, yeah, just a few weeks ago.

[00:28:19] Sani: So how did that go?

[00:28:20] Kevin: It was crazy. So I think if you think back how it all started, right? Like had worked at email companies and had, you know, had a lot of context around email and was sitting there, venture capitalist office and being like, wow, this company called Mailbox, which had come up with this really cool video and they had like, this is like viral video where they would just swipe the emails away and they had come up with this really cool like way of like navigating email, but they had built it just for Gmail and so we're like, wow, that's cool.

But we know this 'cause we had just come out of like the email business that most businesses at that time, you know, this is going back, used Microsoft Exchange, especially big businesses. Um, there was, you know, our friends, you know, all used Gmail as personal accounts and a few new companies used Google for email, but very few.

Um, and so our view was, hey, could you build an app that combined those? Also the iPhone had sort of like exploded. The app that you know was traditionally Outlook and so on, on your computer you had like email calendar, contacts, tasks, all that stuff in a single app. 'cause like email and calendar were in particular were very tied together and contacts like are kind of like in implicit feature.

Um, but on the iPhone they had decided to separate them. You had these really weird interactions of like calendar and email not working well together, context being kind of separated. And so we were like, wow, let's just, if we put all that back together and then did both your work email and your personal email, like that could be pretty cool.

And then just started picking things that happened where it's like somebody, um, would send me a PowerPoint or a deck or some kind of file. Then I would have that file and need to respond to a different person and a different email with that file. Like doing that on your phone was a crazy gymnastics, like hard to save it.

How do you copy? There's no copy pay. And it's like, man, can I just like browse like the attachments 'cause the, you know, my email knows where these attachments are. And so creating some new UI constructs, um. Hey, when can we meet? Being able to like look at my calendar and generate like I'm a avail, you know, kind of like old school before Calendarly had like a link.

Just be able to look at my calendar and pick stocks I wanna offer and then send those back to people. Um, so again, a couple really simple things. Um, and it started to take off, you know, kind of fast forwarding through it. Microsoft got attention. They were like, Hey. They had a mobile app for, for Hotmail, which was their consumer thing, and they wanted to license Acompli to be the new Hotmail app.

Um, and got into that discussion and realized it wasn't gonna make sense, like they would be obviously a very large customer and so big. That they would overwhelm anything we wanted to do at that point. 'cause now we would be working, you know, we would have to scale the team massively to handle this CU customer.

Um, the company would essentially be a vendor for just Hotmail. Um, and so we said that doesn't work. And then, you know, they kind of went down the, Hey, let's acquire you and, you know, made an offer at 40 million. We're like, no. Winter, our lead investor offered him a hundred. They said, n no, go talk to the founders.

And then said, Hey, let's, you know, my co-founder was, you know, had over lunch, was like, Hey, can you make it start with a two? And the next offer was 200. And, and that's kind of how it stuck. Um, and then, you know, somewhere in that kind of first 30 days of diligence, they were like, oh, we we're just gonna rename your app to Outlook and relaunch it.

And that was like, oh wow. Like now it's, we thought

[00:31:35] Sani: now it's big. Now it's official. Right.

[00:31:38] Kevin: So that was a big change. And so yeah. Then got to Microsoft and uh, yeah, we had. Like 10 engineers, four business people. And we showed up and, uh, yeah, by the time we left, I, you know, it's five, 600 people on the Outlook team kind of running all of non Windows, iOS, Android, and Mac.

[00:31:52] Sani: That, that's amazing. And, and from, from long. From from idea to acquisition. How long did it take?

[00:31:58] Kevin: Uh, 18 months. Yeah. So from the time we started the company until we closed, the Microsoft transaction was 18 months, which is pretty fast. Uh, we raised a little over 7 million and then, yeah, sold for 200. Um, so yeah, pretty, pretty quick. And then, uh, we're at Microsoft, uh, for about three years.

Um, and, and that sort of was the time

[00:32:18] Sani: Mm-hmm.

[00:32:19] Kevin: know, it went from zero Outlook users to a hundred million plus, and I think today hundreds of millions of people, you know,

[00:32:25] Sani: Incredible.

[00:32:25] Kevin: mobile phone.

[00:32:27] Sani: Some of the lessons you learned during this process, do they still apply today?

[00:32:33] Kevin: Yeah, I, I think, I mean, there's a variety of ways to, to kind of pick lessons out of like that experience right. Um, I'll highlight three. I think the, the first one is this idea that, you know, if you're building for something that's, you know, gonna be sold for businesses or sold for consumers, right? So I talked to founders today and it's like, are you building something that a million users, you know, kind of a true consumer product?

Or are you building something that you can sell to the Fortune 500? Right where it's like that may not be where you go as a startup or where you start, but it's like, could you imagine what you're building being relevant to like the, you know, 500 largest companies on the stock exchange? Could you imagine something where a million people are using this?

And that is amazing litmus test. And if you think back, accompli solved both of those, right? It was like something that millions of consumers. Theoretically could used, even though we didn't have that many users when we got acquired today. Obviously there is. And then could you sell, you know, build something that was worked for business?

We kind of hit both, which again, as a lesson, you're like, man, if you build something that consumers love and businesses need, that's a pretty impactful thing. I think the second thing was something I actually learned at Yahoo when we got acquired. Uh, so Zimbra got acquired by Yahoo and went in there and we're like, Hey, we're the smart startup guys.

We're kind of cocky we're, we know everything and. We didn't really make a lot of friends early on, um, but also didn't, uh, spend our time really taking stock and valuing the various pieces of like the broader company. And we were like still running to our own, you know, tune to an extent. And it ended up working because through a couple CEO transitions we ended up getting pushed, uh, out to a, uh, you know, and resold to VMware, but. that point on, and then VMware, similar sort of organ rejection, I think to to some extent. When we got to Microsoft, it was like, no, no, no. We're here to help. We're here to be advisors. And I was just talking to a founder earlier and he was like, man, I'm really struggling with kind of fitting in with the big company.

I'm not sure how it works. And I'm like, look man, you need to wake up every morning and you're an advisor. If they tell you to shovel. Your help, your advising, you help, you have better ideas how to shovel. You can offer those ideas, but don't be offended when they don't take them. Don't be offended if they don't listen.

And I think that to me, um, is something that if you click into advisor mode where you're there to help and you're there to offer ideas and offer assistance, but not be offended when people don't do it your way, that that's going to be a much more satisfying way to achieve it. And then I think the final sort of third thing that, you know, we learned at Microsoft is that, you know, big organizations take a long time to change.

And so now when I've worked with, like I worked with a number of large public companies now, and um, you know, you have to understand that the inertia of turning a ship that big and hey, I've been doing it for this way for 30 years, is an incredibly strong force. And so you have to be pretty creative. Both on the human side and the vision side of how do you turn a ship where you have a lot of people that are deathly scared of doing something different.

And I think for AI in particular, we're coming in and saying, Hey, AI can do everything you've done for 30 years and actually do it better and do it 24 hours a day and do it for pennies on the dollar. Like that's a very scary situation, um, for people. And so you need to understand that as you're sort of navigating those, uh, you know, choices.

[00:35:53] Sani: See, this is good advice, especially the advisor. You know, when they tell you to shovel, tell them how to do it better, but don't fight them like this. This is so broad and applies to any consultant. Even working with a company. When they, when they pull them in, you're there to advise and not to fight them on, on their ways.

[00:36:09] Kevin: Yeah. Oddly I learned it with my father on the farm.

[00:36:12] Sani: Oh, wow.

[00:36:13] Kevin: right, in the old days, right? It's like, Hey dad, I, I think we should do it this way. And if he is like. False. And you know, and the cane comes and you're like, Hey, no, we're, and we're gonna do it his way, but at least we offered the advice. But you're okay doing it someone else's way.

And so I think there's a, there's a sense that the company is kind of your boss or your dad in this case. And you, you've gotta kind of do what your parents say, um, even if you think they're completely wrong. And then someday you'll get your choice whether you go build a new company or do something else to do it your way.

But there is this sense of you're going to reach a lot less resistance. Um, if you treat yourself as an advisor where you can offer your ideas or your tips based on your experience, but realize there may be reasons, good or bad, that the other person just doesn't accept your advice.

[00:36:54] Sani: This is excellent advice. Um, let's talk about building a founder brand. 'cause it, I mean your, your, your newsletter founder mode. I'll post, post the link in the description in the episode notes. Why do you think this is important, especially now in 2025, where. You know, if anyone can build anything, I, I'll let you talk, but I have my thoughts on this as well.

[00:37:13] Kevin: Yeah. And so coming out of the last year I was thinking, I was like, man, you know, ha have LinkedIn account, have Twitter accounts, and um, but really wasn't, it was way more view only. Right? I think there was stuff that was out there and it was like promoting different products or different companies or different things.

You know when you made a job change or something, but, and more and more it was like, man, when you do build something or launch something, the days of just being like, Hey, I'm gonna go put it on some website, or you know, it was dig or product hunt. We can go back through the here history of all these places.

You would launch something or I'm gonna get a tech crunch when I announced my funding I think are kind of dead. And so my view was like, well the best way to do this is sort of. Reconnect with the people that you already know and then people that are sort of aligned with your thoughts. And these new social platforms, whether it's Twitter or LinkedIn, they, the algorithms are actually pretty good, like surprisingly, right?

Like I'll see stuff on my feed from like a very small niche thing of something I searched on or something I liked that was on a different feed. And so the idea of like, well, why don't I just try to get better at it? And so the initial thing was like, Hey, I'm, I'm just gonna try to post more on Twitter and LinkedIn.

Um, and started doing that and like got a ton of good feedback and maybe people are just like being nice. Um, but I think it extended beyond that, and in the first month, like 35 kind of people that I would've said that hadn't talked to in at least three years, sometimes more than 10 years, reached out in, I reconnected and had a, you know, meeting with them or something.

And to me I was like, wow. All by just me saying something about Twitter and again, writing a thread on AI or writing something, um. That I thought about startups or founder stuff or even just my health and just being healthier, kind of alerted people that, Hey, I'm still here. And I think part people are like, oh, you're gonna do something 'cause you're now writing.

Other people are like, Hey, it's just good to remember that you're there. Let's just chat and see what you're up to. Um, and so now then I was like, let's make the newsletter. And that sort of turned into this idea of like, you know, here, here we are a, you know, five, six weeks in, I have a thousand people in a newsletter.

You know, it's not a ton, but like pretty quick growth. For like, you know, writing four, four newsletters, right? And again, the amount of connections, the amount of feedback, number of replies, I'm like, oh, that's really good. That was helpful. It's just created conversation. And then to me, like the thing I really started was just like I wanted to get better at writing and communicating.

'cause I think part of it is we're not gonna go in the world where you just wait for tech Crunch to write your article. You gotta write your own story and you've gotta have your own sort of megaphone or your own voice. And so to me, and you look at it today, and I mean, you can read all the studies on founder brands, right?

Like the, you know, the, the Elon is bigger than SpaceX. Tim cook's bigger than Apple. Like, people listen to people, um, more than they listen to companies, right? And then they have a connection. 'cause the companies can, you know, we've seen companies do good things and do bad things. And, um, there's not that same level of connection and loyalty and trust where a, a human that you've built a connection with, um.

And that you sort of vibe with it is, is hard to replace. And so for me, I think I started it more as an experiment to see, but I think like I'm really all in on it and excited about it and you know, probably extend that to, you know, like yourself doing podcasts

[00:40:19] Sani: Another thing about that is you want the people who are interested in whatever you're doing to know you're there and to know you're doing just that. And you want to be the first to their mind when they need a person for that specific thing. Like if you can do that, if you can achieve that. You did half of your job, basically half of your work.

I was watching a diary of a CEO episode this morning. Part of it with, uh, Mr. Beast. It, it's great. It's really, really a great interview. And we talked about this building one of the products last year. Like it's about your attention. 'cause you can beat the best tech startup in the world if Mr. Be. Mr. Beast decides to build that same product.

Guess who's gonna have more users like you don't have, you don't send a chance if people don't know what you're doing. And that megaphone, but also one-to-one conversations, which are extremely important in building an audience. In my opinion. The trick is how to do them scale, but being able to talk to the audience and being able to get their ears and them listening to you when you have something to say.

I, I think that is a trick. And that building the product is only half of the equation. Marketing it and, and getting people to care about it is really what's, what's going to be even bigger in the future. One final question. So, um, how do you balance automation versus human pure human input and that automation could be, ai, could be anything in your life, work.

[00:41:45] Kevin: Yeah, I, I think for, you know, again, if, if, if I was operating on my body where I'm not a doctor, I'd probably be a lot more careful to just like, ask, chat to go like surgery. I, I, I definitely would ask, chat their opinion of what kind of surgery I can get or what doctor, or what's the, you know, better question to ask my doctor.

But I think most things that we do in the world are not working on operating on our bodies or are, um, you know, launching the space shuttle where there's just higher risk. And so for us, most things I try to automate first, right? I try to make that first pass of like, can you reduce the cognitive load of figuring out the, the best thing by automating or at least getting, you know, some chunk of the way there.

And then being willing to use human, you know, sort of input or resources or effort to sort of close the gap. And so for me. The, my first move always is like, ask chat, like, what, what would chat do? How do I get there? And literally talk to it as if it's my smartest friend. Make that, you know, they're an expert in a lot of things and just see like, Hey, does that make me ask a better question?

Um, so it's created me to ask better questions, but also be a lot more. Thoughtful in my sort of delegation and sort of giving out instructions. 'cause the more detailed you are with Chad, of like giving it more context, you actually get better answers as we've all learned. And so I think that's very true with working with humans or working with a team as well, right?

Like the more specific and the more context you can give on like, hey, we're gonna go do this thing. Right? Like, are we shoveling because we're, you know, putting in a gas line or are we shoveling because we're trying to unclog, you know, or put in grass or whatever, right? Like how deep you dig, what, what workarounds you're gonna hit to.

And we hit a root, like that's a different problem. We're gonna cut through the root and keep going. Maybe in some cases, in other cases, like, no, no, no, we're gonna save the tree. Like do something else. So I do think this idea of automating, being ask great questions and give a lot of context. And then using the human to sort of fill the gap and, and we'll sort of see over time as those, the percentages of each change.

[00:43:51] Sani: love that. Kevin, thank you so much. I cannot believe this hasn't happened until now. Like it's been four years of this podcast. We've known each other for 16 years. This was such a good episode, such an amazing episode. Uh, and for my audience, go, uh, delinquent. Be in a description of subscribe to founder mode.

There's a lot to learn there. Kevin. Thank you. Thanks so much.

[00:44:11] Kevin: Awesome, man. I appreciate the time and uh, yeah, good to chat and, uh, yeah, an incredible sort of time and, uh, yeah, I've been following No Hacks forever and so it's kind of funny that we've never done this, but, uh, thank you again for setting this up.