Daniel Kivatinos Post-Exit: Why I Am Building Again
Episode - 59
Daniel Kivatinos Post-Exit: Why I Am Building Again
On this podcast we've explored many dramatic post exit stories. Tales of existential crisis, addictions to drugs, alcohol, sex and obsessive money chasing, extreme sports, mind blowing adventures and long spiritual journeys to faraway lands.
Daniel Kivatinos journey is different and just as important to hear. His pause after selling his company didn't push him into a new path. It gave him clarity that he was already on the right one.
Daniel built and sold DrChrono, one of the first mobile medical platforms processing billions in medical billing. His work even took him to the White House to help shape healthcare data policy.
Today, Daniel is building JustPaid, an AI powered platform changing how businesses manage accounts receivable.
In our conversation, Daniel shows us how he built that conviction about who he is and what he truly wants to do. In his case, to keep building highly impactful tech companies right in the heart of Silicon Valley.
What We Discussed:
00:00 – Fulfilment: “Some days I’m a five, some days a six”
00:19 – What would it take to feel like a 10?
00:58 – The illusion of a “perfect place” in life
01:17 – Mountain after mountain: why satisfaction always moves
01:37 – Introducing Daniel Kivatinos & his journey from DrChrono to JustPaid
02:14 – Can a life ever feel fully “satisfied”?
03:11 – Starting the conversation: Daniel joins the show
03:17 – How he discovered the podcast & why it resonated
03:36 – He sold DrChrono… and then started a new company within a year
04:05 – Why founders can’t take long breaks without losing their edge
05:40 – Did one year off give enough space for clarity? (Short answer: no.)
06:21 – Why entrepreneurs struggle with taking real time off
07:57 – The addictive nature of building companies
08:40 – Is the second company easier? (Spoiler: no, just “different hard.”)
10:10 – Is it ever easier the second time? Unrealistic expectations
10:43 – “You can’t hire people to build it for you”
11:40 – Even Steve Jobs struggled with his second company
13:07 – Why second-time founders often fail
14:33 – What Next actually gave Steve Jobs later
15:19 – Connecting the dots only works backward
15:44 – What Daniel did during his year off
16:40 – The Reddit founder told him to move to California
17:22 – Early Y Combinator days & why he never returned to NYC
17:39 – Considering moving away after the exit
18:01 – Missing family and exploring other states
23:15 – “What should I do with a year off?” His advice
23:59 – Driving across the U.S. twice — unstructured freedom
25:05 – The joy of having no plan
26:25 – Driving across the Great Salt Lake (the slightly risky part)
27:11 – Why unstructured time matters after a big exit
27:31 – Realizing he wasn’t “done” with tech or Silicon Valley
27:57 – Three years later: is he happy?
28:07 – Business as a game, not just work
29:32 – Creator vs operator: early-stage founders must be both
32:41 – Did his son influence the decision to start another company?
33:58 – Modeling meaning and fulfilment for children
36:08 – Why he became an entrepreneur in the first place
36:14 – Graduating into the 2008 crisis
36:40 – Discovering startup life and loving the creative chaos
38:23 – It wasn’t about money — it was about people
40:49 – Two failed startups in a row: learning without financial reward
41:11 – Motivation after exit: still driven by curiosity, not fear or money
42:13 – Curiosity as the true engine behind building companies
43:17 – Why no single motivator is enough to build a company
45:01 – “Stay hungry, stay foolish” — Daniel’s interpretation
46:36 – Work-life balance vs. work-life integration
46:45 – How he designs balance in his second company
48:40 – Why remote culture supports family life
49:26 – How much he actually works
49:35 – Comparing work intensity: first company vs second
50:16 – Why he set up the company so co-founders push each other
50:22 – Returning to fulfilment: the moving target
51:00 – The mountain metaphor: why fulfilment never stays
52:07 – What a “10 day” looks like for Daniel
53:42 – Finding joy in the small things
53:59 – Why the end goal will never create long-term fulfilment
54:18 – “How do you want to be remembered?”
54:29 – Family, impact, and acceptance
56:16 – Graveyards, billionaires, and perspective on legacy
57:13 – Closing reflections & farewell
-
Anastasia:
[00:00:01 - 00:00:06]
So on a scale from 0 to 10, how fulfilled do you feel?
Daniel:
[00:00:06 - 00:00:19]
Depends on the day. On average I would say a five. Okay, maybe a six. I don't know, it's, you know, it depends on the day. Some days I'm really happy.
Anastasia:
[00:00:19 - 00:00:57]
What would you need to get to 10? On this podcast we've explored many dramatic post exit stories. Tales of existential crisis, addictions to drugs, alcohol, sex and obsessive money chasing, extreme sports, mind blowing adventures and long spiritual quests to faraway lands. Daniel Kvatinus journey is different and just as important to her. His pause after selling his company didn't push him into a new path. It gave him clarity that he was already on the right one.
Daniel:
[00:00:58 - 00:01:09]
In your head there's always like this perfect place. And I'm like, I don't think I'll ever reach that perfect place. You think it's there. You're like, if I get this, you.
Anastasia:
[00:01:09 - 00:01:14]
Can still dream of it. So do you know in your dream whether it's realistic or not?
Daniel:
[00:01:17 - 00:01:36]
I think that there's a lot of hills. So like if I climb this mountain and I'm like, I got through the mountain, then I see another mountain over that, I'm like, let me get through that mountain and I climb over that mountain and then I'm like let me get. I think that you're never actually satisfied even doing the thing you like want.
Anastasia:
[00:01:37 - 00:02:14]
Daniel built and sold Dr. Kronal, one of the first mobile medical platforms processing billions in medical billing. His work even took him to the White House to help shape healthcare data policy. Today, Daniel is building Just Paid, an AI powered platform changing how businesses manage accounts receivable. In our conversation, Daniel shows us how he built that conviction about who he is and what he truly wants to do. In his case, to keep building highly impactful tech companies right in the heart.
Daniel:
[00:02:14 - 00:02:36]
Of Silicon Valley, is there like a fully satisfied life? There are days like when I wake up and I'm like, this was a really good day. Everything went the way we wanted it and I just feel like a 10. And I'm like this is a great day and this is maybe how I work long term. That's why I can do it. So long is you look at like the little things to make your life happy.
Anastasia:
[00:02:37 - 00:03:11]
My friends, we are here to help each other make better decisions post exit with our time, energy, wealth and relationships. If what we share here resonates, let us know by subscribing or following it helps us bring on incredible guests and reach more exited founders who need these conversations. Do me a favor. Hit that subscribe or follow button. We're in this together. Hello, Daniel.
Daniel:
[00:03:11 - 00:03:12]
Hi.
Anastasia:
[00:03:13 - 00:03:17]
Thank you so much for joining me today. I have some really interesting questions for you.
Daniel:
[00:03:17 - 00:03:36]
So I'm very excited, awesome, excited to be on. I found your podcast randomly and it was really enjoyable to hear just some of the guests you had on. They were super insightful and I could relate in a lot of ways. That's why I think it's a really great podcast for people just to listen to, to hear about.
Anastasia:
[00:03:36 - 00:04:05]
Thank you so much. I wish everybody started an interview with a compliment. I love it. That's brilliant. Thank you so much. So Daniel, you sold Dr. Chrono in 2021, four years ago, and then you jumped into your next business within a year. Just in. In about a year. So let's talk about why you made this decision pretty soon after the first exit.
Daniel:
[00:04:05 - 00:05:40]
I mean, when you think about someone's career, if they take a gap year or two years, I think you begin to atrophy as like an industry expert. And I'm in tech, so I'm in AI, I'm in software. Things move so fast that someone who's kind of out of the business, who just is not working day to day, loses touch within literally months and, you know, self reflecting. When you move on from a company or a business, there's also this pressure to keep learning. That's just innate and natural. For anyone who's like running a business or like working in a business as an employee, there's a natural pressure to just continually make yourself better. How do I work better with people? How do I learn better technology? How do I understand how to be more efficient personally? And you know, when you release that pressure valve, I think it's hard for an entrepreneur or an employee to like step on the gas very quickly again and start to like move quickly. So, you know, for me, I felt like if I didn't step on the gas within like a two year, three year period, you kind of lose your way and you're like a, you know, a. That pressure point is not there.
Anastasia:
[00:05:40 - 00:06:13]
Yeah, I very much agree with you because it's my observation as well that if people take too long, it becomes harder and harder. And what happens is that we start developing new habits, we start developing this external scaffolding that supports life without business. And then it's so hard to break out of it. So that makes so much sense. But did you feel that that year was enough for you on the personal level to figure out what you want to do next?
Daniel:
[00:06:14 - 00:06:15]
The Answer is no.
Anastasia:
[00:06:18 - 00:06:20]
Thank you for your honesty. Why not?
Daniel:
[00:06:21 - 00:08:40]
I mean, you can always take more time off, right? You can always, like, relax more and enjoy life more. Life is not all about work. It's not right. But if you're not pushing yourself in an uncomfortable way, you tend to not want to do that again. So I understood my own psychology where I said, hey, you know, traveling is great. I can go into the details in a little bit of, like, what I did in that year off. But, you know, psychologically, part of, like, what an entrepreneur is is, like, putting that pressure on yourself to make something amazing. And if you get used to, like you said, the scaffolding, it's like you start to build new scaffolding. I wasn't quite ready to go fully commit to that because I felt like I wasn't done, like, building and creating. And for me, I get really addicted to the highs and lows, candidly, of building. And there's a real fun aspect to being an entrepreneur. And there is. It's not a lonely life building companies. You have community. The community is like the company you build, right? And that's a lot of fun in itself where you have, like, a sports team and you're all, like, going towards this specific goal. And I think when you remove that pressure and, you know, you're not part of that sports team, you know, you kind of. You start to change. And I think, you know, I see entrepreneurs who take two years off, three years off, five years off, and they basically make the decision they want to become an entrepreneur again. Not that it's harder. I just think that their scaffolding is in place for other things where they may not have the fortitude to do it right. Because there are nights where I'm up till 3:00am, 4:00am like, just specifically focused on work.
Anastasia:
[00:08:40 - 00:08:45]
Do you find it easier or harder the second time around?
Daniel:
[00:08:45 - 00:10:10]
I think it's just different hard. I think it's different in different ways. Where, say, you buy a car and you've used that car for 10 years, and you know where all the parts are and the buttons and the lights and you know where to fill the tires up, and you know, how long the car can run without, you know, before running out of gas, you get really comfortable in that. But then when you're in a new car, it's like, oh, like, I need to really understand, like, how this button works. That button works, like, so, like, you're building a new culture, you're building a new team. You're understanding the team dynamics. You're figuring out how do we all work well together? It's more nuanced. It's almost like a new relationship in a sense. It's like either when you're dating somebody new or like you're, you know, trying something new, like, I don't know, a sport or like just something that's just slightly different. And I think, you know, every company at the end of the day has its life cycle. And whether that's 100 years or 5 years or 10 years or 200 years or 300 years or 50 years, change is always happening. And I think that the best entrepreneurs can understand that change and move with it. So I just think the challenges are always there. It's never easier.
Anastasia:
[00:10:10 - 00:10:43]
Did you expect it to be easier? Because I hear it all the time when people are thinking, shall I start a new business? Shall I take a longer break? Shall I start doing something else entirely? And at the end of the day what they're trying to figure out is is it possible to make it easier on myself second time around? Did you try to answer that question or you were just prepared and willing to work hard again, as hard as the first time?
Daniel:
[00:10:43 - 00:13:06]
I think I went in eyes wide open knowing that these don't, businesses don't just create themselves. And it's funny how like I spoke to somebody last week and they said, why don't you just hire people and they'll just run it for you, right. When someone asks that question, it's like a very, I'd say, naive question because like you can't just hire people to run and run with it and build it and try to build something that's very scalable like in a, I would say a venture backed type of company. And I think going in thinking it's going to be easier is silly. It's never going to be easier. Like take Steve Jobs and Next. Right, Next. Steve Jobs was, you know, at Apple and one of the co founders of Apple. He was fired from Apple, left Apple, started a company Next. And it was a real struggle even for Steve Jobs, someone that had ultra wealth. NEXT was almost a failure in a lot of ways. Yeah, yeah, it was a failure. So it tells you like, yeah, the best. And you know, is he one of the best entrepreneurs? I don't know, maybe, maybe not. I just know that he created Apple and Apple's one of the best companies. Yeah, he then he went on to create a failed company. What does that tell you? Like that's just one data point out there. And you know, I do think he went in eyes wide Open. I think he understood the stress. I don't know. He. He seemed like he was very hands on, like, worried that the company would fail if he wasn't involved. So if you're going to do a second company, you have to go in eyes wide open, realizing this is not going to be hard. It's completely different. I'm not going to name names. I was literally talking about an entrepreneur in San Francisco who's ultra famous, ultra famous guy and his first company. Everybody out there knows the name of his company. He started a second company, and it was a complete disaster.
Anastasia:
[00:13:07 - 00:13:08]
Happens a lot.
Daniel:
[00:13:09 - 00:13:12]
Yeah, yeah. And I'm talking to one of his. Yeah, exactly.
Anastasia:
[00:13:13 - 00:14:32]
Yeah. But even. Even with Steve Jobs, it's a great example because Next did almost fail, and maybe it would have failed if not for Steve's reputation and connections and all these other things. I think Jobs started it so early because he was so, so early after he left Apple because he was so angry. There was this momentum. And later, by the way, he did mention at least once that he wished he took a year off. So you are doing the right thing, Daniel. You're smarter than Steve Jobs. You took your year off, he didn't. And maybe if he did take a year off, maybe he would have started a different company, but it did end up well for him. But I see so many cases where people start a new company thinking it's going to be easier. I can have employees, I can throw money into the problem and it's going to work. And it does not work, actually. Oftentimes it's really tragic because that person throws so much money onto the problem and then gets stuck because they're not interested. Their heart is not in it, and the company cannot. You cannot lift it off the ground. Without that founder's passion, I don't think it's possible. So I'm very much with you on that one.
Daniel:
[00:14:33 - 00:15:19]
Got it. I mean, if Steve Jobs didn't start Next, he may not have become the CEO of Apple again. So there are some downsides from him saying that, that he doesn't realize he might have taken that year off because oddly, a lot of what runs in the Mac today is just. They rolled it into. They rolled in what Next had built. So, like, he kind of got to be CEO again because he built Next. And they had this beautiful design and architecture. And then Apple said, we need this. We need Steve Jobs back here because he's doing this. So there was a weird benefit that he doesn't realize from starting right away that happened.
Anastasia:
[00:15:19 - 00:15:44]
But, you know, There's a famous quote from Steve about connecting dots, something that's only possible when you look back. It's very hard to see it in front of you when it's happening, even for people like him. Very, very true, Daniel. I really want to go back and hear what it is you did during that year.
Daniel:
[00:15:44 - 00:16:38]
I mean, that was a really fun year. I started to research, like, where would I want, like, to live in the world? And I'm like, what's the right place? I started to research, like, where do I want to go in the US I started to look at just, you know, what type of life I want for myself. And, you know, I. I have a interesting story where I started my original company in New York City, and then the investors pulled us to California, and we moved to California for our first investors. Our very first investor was actually the. The founder of Reddit.
Anastasia:
[00:16:38 - 00:16:40]
Oh, okay, okay, okay.
Daniel:
[00:16:40 - 00:17:22]
Came to our offices and basically saw what we were doing and said, you have to come out to California. I want to introduce you to Y Combinator. They were small. This is 2010, and me and my co founder had heard of Y Combinator. It wasn't big back then. It was pseudo big. You know, their. Their batches were smaller than they are now, and that you got way less money than what it is now. But the founder of Reddit basically convinced us to come to California for three months, and we moved for three months and never came back.
Anastasia:
[00:17:22 - 00:17:24]
And you're in Palo Alto now, aren't you?
Daniel:
[00:17:25 - 00:17:26]
I'm right near Palo Alto.
Anastasia:
[00:17:26 - 00:17:26]
Yeah.
Daniel:
[00:17:26 - 00:17:29]
I'm right on the outskirts of Palo Alto.
Anastasia:
[00:17:29 - 00:17:37]
So. So let's go back. You were thinking about all these different places in the world and in the US to move to, but you are in Palo Alto today.
Daniel:
[00:17:38 - 00:17:39]
Yeah. Yeah.
Anastasia:
[00:17:39 - 00:17:40]
How did that happen?
Daniel:
[00:17:42 - 00:21:53]
Well, the investor had a office here way back when in Mountain View. So Y Combinator kind of had this, like, small warehouse. The one of the founders, Paul Graham, like, found a really nice location in Mountain View, specifically because Mountain View had some of the most boldest investors. Sequoia Capital is here, Bessemers here, what you just mentioned. Every investor that's like a venture capitalist specifically is like, in this area, and they have, like, a footprint. And what happened with them is, I mean, they decided because all these investors are here, investors don't move to entrepreneurs, entrepreneurs move to investors. So they situated here, bought this warehouse, and then strategically went around looking for really good entrepreneurs and had them come join the Y Combinator investment portfolio. And for me and my co founder, candidly, when we first Got our first investment from them. It was not a lot of money. So back then, it was small amounts than what it is today. So I think I'd call it the true believers back then, where you just get a little money and you get a lot of support. Things change where you have a lot of support now and a little money. But we moved right near that area, and when I moved here, I realized the. The vibe is amazing. The infrastructure is amazing. The way that people move about the world here, it's like a really nice environment where you can, you know, work for a bit, then go grab lunch, then go back to work, then your home is not too far. I think some places where I live, like New York City, it's just. There's a different element of stress where you're hopping on the subway. You know, you hop on another subway, you walk five blocks, and then you're at your office. And then you. You leave your office, you grab lunch, you wait 25 minutes because there's a line of, you know, 60 people in front of you. So there's a different vibe. And I really liked the vibe in this area and the. The California, I'd call it, like, pseudo city vibe, where it's not quite a city. It's like a. I mean, technically, Mountain View is the city of Mountain View. Technically, it's a city, but it almost feels like suburbia, but with, like, more infrastructure. So I felt really comfortable in that. And we situated here, and I didn't move back to New York, and I just said, let's just stay here because the infrastructure's here and all the investors are here. And this is what. This is kind of how people get trapped in California. Like, there's a. You get, you know, love it or hate it, There's a reason why people keep coming here is because there's so much, like, situated in such a good way. And, you know, when you're here long enough, you run into people. Like, I've met at this point, thousands of angel investors that just are walking around the area. Like, yesterday, there were two angel investors. Literally, I never met them in my life. And I just went to an event and they just happened to be there, and they were doing investing. And I'm like, this is just the place where you've just run into people like that. And it's just the mindset. And I'm like, it's a really good, healthy, like, economy, in a sense. It's like a micro economy of, like, the boldness of the angel investors, the boldness of the VCs. Then you have Stanford right down the block, which is like a brain. It's basically like you're pumping out all these amazing smart people from there. And then you have Y combinators and the VCs, and everyone kind of just pooling together. Yeah, you have this great place, so it's hard to leave. That's my point.
Anastasia:
[00:21:54 - 00:22:01]
Daniel, after you sold your company, you did consider moving away. Why was that?
Daniel:
[00:22:01 - 00:23:15]
My family's on the east coast, and I think, you know, when you're away from your brother, sister, family members, you know, you kind of miss a lot of that, like, family life, I think. So that's probably the hardest part for me. But, you know, I looked at other places also. Like, just everywhere in the, you know, everything from, like, Wisconsin to, like, like, Washington to, like, Florida to just, you name it, Ohio. And I'm like, what's the. What would life look like in these different places? And I think it's great. I. That's one of the great things I like about where. About the US Is just the variety of places you can live and just, like, the different lifestyles you can have. And, you know, I considered buying a farm at one point. I'm like, oh, that looks interesting. But, like, you really have to be responsible for all of the animals, right? Like, you don't leave. You're just taking care of all of your, you know, animals that you need to care for. So I'm like, that would be really rough in some ways. So, you know, things like.
Anastasia:
[00:23:15 - 00:23:57]
So you considered all these other options. You went and visited and imagined yourself running a farm or doing this and that. And at the end of the day, you decided to stay in California and start a new business. What else did you do that year to, I guess, recover? Because I'm sure there was some burnout after the sale. Just physically, you probably needed to recover. How did you go about that? What else did you try? What worked? What didn't work? If I asked you, I just sold the company. I have a year. What should I do? What would you say, based on your experience?
Daniel:
[00:23:59 - 00:25:05]
I mean, you know, one thing that I did was drove across country twice. So I, you know, I bought a large car, essentially, and then decided, I'm going to just drive across the United States. And it sounds silly, but it was. It was probably one of the best, like, unexpected, like, trips that I took because there was no plan. There was no, like, we're going to stop here. We're going to do this. And, you know, you get to know, like, like, I'M married. I have a wife and a son. So, like, we went with our dogs, who on the. You know, we piled everyone into the car and just started driving across the country. I just think that that type of a thing, like, really, it's just nice to do. And driving is not for everyone, but it is for me. Like, when me and my wife and my son are like, driving, we just kind of all bond a lot. And our. The dogs love it. They just love, like traveling and so.
Anastasia:
[00:25:05 - 00:25:09]
Not having a structure or a plan. Did it make you feel free?
Daniel:
[00:25:09 - 00:26:25]
Yes. But we also had a destination which was like, to get to the other side where my other family was. So, you know, we. It was kind of chaos and, you know, disorganized chaos, just driving across the country. So it was. There was a lot of freedom in it because we just would pull over in random places. And I have just like really random memories. And I'll tell you a couple of them. Like, I forget the name of it, but we're driving through one state and there's just this like, lake of salt. I forgot the name of this. The Great Salt Lakes, I think it's called. Anyway, we're driving like past this and, you know, my wife's like, pull over, let's go look. So we pull over and, you know, the next thing she's saying is like, let's just drive on the lake. I'm thinking, this car's heavy and it's gonna sink. But there was so much salt packed it down on this lake. I don't know what I was thinking. We just like drove out in the middle of a lake. And I'm thinking, if the lake salt breaks, we're going down. And yet we did it anyway. And there was no police.
Anastasia:
[00:26:26 - 00:26:27]
Yeah, it was pretty crazy.
Daniel:
[00:26:27 - 00:26:40]
Yeah, she just wanted to do it. And I'm like, all right, let's do it. So it's, you know those crazy stories like that where you just. It wasn't planned, you know, so that.
Anastasia:
[00:26:40 - 00:26:43]
Was a good idea. You would recommend someone to do that?
Daniel:
[00:26:43 - 00:27:11]
I think it depends on someone's personality. Like if you're up for a long drive because it takes about seven, eight days, you know, maybe 10 days, depending on, like, if you're stopping places, could take 15 days. It depends on a person. I don't have a Tesla who knows self driving cars. Maybe you don't even have to look at the steering wheel. God knows if those work well. But I was driving and my wife was driving. We were trading off the whole time.
Anastasia:
[00:27:11 - 00:27:31]
So you basically took this year of pretty unstructured life, considering living in other locations. And then you realize that you don't want your skills to atrophy. You want to stay connected to technology, and you want to stay connected to.
Daniel:
[00:27:31 - 00:27:57]
The Valley, I would say so. There was a part of me that was tied here, and subconsciously, I felt like I wasn't done. Like, I'm not done. I need to figure it out, because there's a part of me that, you know, there's a part of me that likes a vacation, and there's a part of me that likes work. So you have to, like, find that balance for yourself.
Anastasia:
[00:27:57 - 00:28:06]
Like, okay, so now, three years in, are you happy? You're doing business and not having vacation?
Daniel:
[00:28:07 - 00:29:32]
It's not a matter of happiness. It's a matter of you want to stay in it for, like, the fun of the game. Like, business, in a sense, is like a sports game. Like, it is a game. Like, you have winners. Like, you have, you know, people like Jeff Bezos, who wanted the game of business. And then you have, like, other entrepreneurs who are really struggling. For me, I like the game of business a lot and figuring out, how do we become successful? How do we make this really thrive? How do we make an amazing product? Like, when I see someone use a product, I get, like, a natural endorphin hit. So when they're using our product, right today, we built, like, an AI agent to help collect revenue. I get an endorphin hit when I see someone using our product, and I'm like, this is awesome. Like, I love that this is working for them. And when I get that feeling, it, like, washes other feelings away. And every entrepreneur will lie to you and say, you know, I love what I do. This is great. There's a lot of bad times that come in being an entrepreneur, but, like, I knew going into this that that would also happen.
Anastasia:
[00:29:32 - 00:29:39]
If you had to choose whether you are more of a creator or more of an operator, what would you choose?
Daniel:
[00:29:39 - 00:29:42]
You have to be both at the early stages.
Anastasia:
[00:29:44 - 00:29:46]
As a company, everything at the early stages.
Daniel:
[00:29:46 - 00:32:39]
Yeah, as a company scales, and you're like Coca Cola. You need a lot of operators in Coca Cola because you're logistically shipping soda everywhere across the world. At the early stages, you really need to be everything all in one. Like, you have to be creative. You have to delight the user. You have to operate the company appropriately or you'll run out of money. You have to literally figure out what the culture is going to be. You have to figure out, you know, who, what the market is, you have to figure out who your investors are going to be. You have to kind of go through this journey and do all, all of it, like design your website, you know, design pieces of the product, what's the web, you know, the flow of the product. So I think it's hard in the early days to be like just to bifurcate. I do have co founders in this company so, you know, actively I felt like I needed to fill gaps where as a second time entrepreneur you have to fill areas where you feel like your co founders will push you. And I do think that there is a, I have seen this, like, I don't know, maybe it's a syndrome or something where some second time founders will do it all themselves, say, you know, I'll just hire people and I'll do it all myself. And for me, you know, I think having co founders is absolutely essential to like building a company because the days when I feel like this is hard or whatever, market forces outside of our control market is changing. You know, you have VCs scared because of market conditions, whatever it might be. You have co founders that are just covering bases when you're down because of something. Right. So for me, I look at it as like co founders will push me psychologically out of my comfort zone, I'll push them psychologically out of their comfort zones. And it's kind of a game of like pushing each other. So, you know, second time co founders, I mean, second time founders should have co founders at least in my opinion. And they should either be friends or past colleagues that you've worked with. I don't recommend just meeting somebody on the street that's like an expert in AI and saying let's do a company together. That's where it's a little dicey and dangerous. But if you had like a 10 year relationship, a five year relationship, a two year relationship, it doesn't hurt to ask.
Anastasia:
[00:32:41 - 00:32:46]
So Daniel, your son was eight when you sold Dr. Chrono, is that correct?
Daniel:
[00:32:47 - 00:32:50]
Around that age? Yeah, around that age.
Anastasia:
[00:32:50 - 00:32:59]
So your decision to go back to business, was it influenced at all by your thinking about what you model for him?
Daniel:
[00:32:59 - 00:33:58]
A little bit. Not totally, I think. I mean kids are going to watch what you do, right? And they're going to learn from you. But he also has to see that I'm happy, right? So like if you have kids, you want them to see your life have meaning. So for me it was more about like what's going to make me happy indirectly, he's going to see that and Then be influenced by that. And you know, I have a very open mind to like, he's gonna do what he's gonna do at the end of the day, like, I'm not gonna force him to be an entrepreneur. If he wants to be anything he wants to be, I'm just gonna support it. Like, you can't. I mean, this is just my perception, you know.
Anastasia:
[00:33:59 - 00:34:04]
But whether you like it or not, he will look at you as a model. And he does.
Daniel:
[00:34:05 - 00:34:05]
Yeah.
Anastasia:
[00:34:05 - 00:34:10]
So there is this responsibility if it's a son, especially for the father.
Daniel:
[00:34:10 - 00:34:11]
Yeah.
Anastasia:
[00:34:11 - 00:34:26]
Because for a mother it's a bit different. But sons do copy fathers to some extent, or at least not copy necessarily, but they learn from what their fathers do rather than what they say. Would you agree with that?
Daniel:
[00:34:27 - 00:36:07]
I would say so. I would say so. I. He wasn't the deciding factor in my decision except me being happy. Like, I wanted him to see like, what fulfills dad, like. Right. And if he's happy, that's what I should do, is take that path that I feel like is what I want. And I think, you know, looking at my father and like just looking at his past, I don't think he was able to do what he wanted. So he wanted to be an airline pilot, my father, he wanted to like fly planes and travel and, you know, be an airplane, airline pilot. But his father, my grandfather, said, that's an unstable job. You're not going to do that. You're going to work for the government. And my dad did work for the government for many, many, many years, which was a really stable job. But he wasn't doing what he loved. And I think when he had me, he just said, do whatever you want. So like, he kind of just let me pick and choose and explore and just, he kind of embraced what I was just interested in. Yeah, he was trying to influence me here and there. Like, I remember him like being like, let's go get airplane airline, you know, let's go get some airplane lessons. That was like a 12 year old, you know, and he's sitting with me in a plane. So like there were, there were glimmers here and there, but he wasn't pushing me, like to do.
Anastasia:
[00:36:08 - 00:36:14]
So why did you become an entrepreneur in the first place? What was your original motivation?
Daniel:
[00:36:14 - 00:38:23]
I saw the world like falling apart. So this is 2008. Graduated college, got my first job. Was, was excited. I worked for a startup in New York City. So startups were not a big thing in 2003, 2004, but I just was fortunate. Like they liked Me, I liked the people there. It was a small group of people. I felt like I could have influence. I really liked the guy I worked for because he was passionate and we just kind of hit it off in my first job. And it was a startup, it was a true startup. So like I could code something. I was a developer, I could code and the code would be live within like a minute. So there was like real power in like making right. And I'm like, I like this because it feels like college. It's like unstructured chaos. And I'm coding this product and it's going live to, I don't know all the users that are using it. And it was a lot of fun. But I interviewed at some of the bigger companies, you know, before taking that job. I interviewed at Microsoft, I interviewed at Bloomberg, I interviewed at Google. Something was off for me. I don't. It was like the big company mindset where you're not going to have the impact that you want. So I, you know, interviewed with this guy who was effectively the only engineer at a company of 12 people and he hired me and the salary was egregious. So I didn't take the job just for the money. Like it was. It wasn't a high paying job, I'll just tell you that. And I'm like, it's a startup. I'll just take the job and I'll get this salary and I'll see how this goes. And he just was teaching me every day and I was learning on my own every day.
Anastasia:
[00:38:23 - 00:38:34]
And did you have any financial motivator in that at all? Did you feel this path will bring you a better financial result than being employed?
Daniel:
[00:38:34 - 00:38:41]
The answer was no. I didn't feel like I was going to have a good financial result, but I didn't really believe in it.
Anastasia:
[00:38:41 - 00:38:41]
Did you?
Daniel:
[00:38:44 - 00:40:49]
I just liked the people I worked with. I think that's really what it was because they were just really smart people and they were doing something interesting. That's what motivated me. And you know, they were. I don't know if you used Udemy or Udacity or Creative live or like YouTube is basically the learning platform of choice now, right? Like everybody learns everything on YouTube when you want to watch a video. We were doing that before YouTube even became big. And you know, it was a bunch of professors, Oxford, Stanford and Yale got together, funded a startup and we tried to create that. There was a lot of nuances there. Why it failed. I think one of the reasons why that failed was they were trying to charge a Lot of money when the Internet wasn't a thing yet really. So it was like doing too many experimental things all at once. Created this like it just wasn't the right time for that product. I think today if something came along like that, people are way more open minded to online, like education. It's just a thing now. Massive online courses. Back then it was really new and like innovative. Too early for its time. Anyway, that company failed and then I went to go work for another startup which was like these three guys and they were just building this thing and I just liked the people. It was the people for me. It's like I wanted to work with fun people that I could learn from and they were really smart guys. Like they were just savvy enough to get their company to a position to get acquired by a larger startup. So that small three person startup got acquired by a larger startup. The same thing happened where over time that larger startup didn't quite get product market fit and it went bankrupt. So I went from one failed startup out of school to another failed startup out of school.
Anastasia:
[00:40:49 - 00:41:00]
So if you had financial motivations, you would probably be quite devastated by this. But because you didn't, it probably didn't hit you that hard.
Daniel:
[00:41:00 - 00:41:11]
I mean I made no, candidly there was no money in what I was at that point in my life. It was me just like exploring like what I wanted to do. And I think, and it sounds like.
Anastasia:
[00:41:11 - 00:42:12]
It'S still the same now, isn't it? Your motivation seems exactly the same for your new company, which, which is fascinating because I talk to so many people whose motivation changes dramatically after they exit. And it can be one of two things really more often than not. Sometimes people had a financial motivation in the beginning. They had some kind of fear of poverty or they had a need for money. So that was the motivation. And after the exit, especially if it's a life changing financial amount they get through their exit, they have to go through the whole transition of finding another motivation to start a business and oftentimes they never do. And another group of people, which is very common are those who believe that if you don't have a chip on your shoulder, you would never become an entrepreneur in the first place. But I find you so fascinating because you don't seem to have either.
Daniel:
[00:42:13 - 00:43:17]
There's always a motivation to like all of those things are true all at the same time. For me, like everything you're saying, I'm like, yes to that, yes to that. But like without the underlying curiosity, like I like to learn, it's Fun. And I think that curiosity is like one of the legs of the stool. Like, you know, incentives like love it or hate it, anybody that starts a business is doing it for profit. Right. There is that part of it. And there, you know, the reality is like the United States is an open market and it's just designed that way. So if I am learning and I enjoying this experience, it should be also to make the team and the company better. But if I didn't have fun, I wouldn't do it. I would just give up doing that and do something else that I could have way more fun doing.
Anastasia:
[00:43:17 - 00:43:22]
So you're chip on the shoulder and the financial motivator wouldn't be strong enough to pull you through.
Daniel:
[00:43:22 - 00:43:45]
Yes, a hundred percent. Yeah. So you need all these different like pieces of it to like really push it forward. Because when an entrepreneur tells me they're doing this just for the good of the world, but they created a corporate structure, it's like there are other factors there. And you just have to remember, like, you created a corporation for profit. Right. And you know, it's just another reality.
Anastasia:
[00:43:46 - 00:44:46]
To be fair, there's a different argument in this potentially because I do talk to people who say exactly that. They had big exits, they really don't need the money, yet they do create. They choose to do a business and not philanthropy later on. And oftentimes the reason is because they actually want this entity to be self sustaining. Right. And if there is no financial health, then this company will not survive for very long. And sometimes also these people would so much love the game of the business that it would inspire them much more than the philanthropy world, which tends to be much slower and more like a government organization. So I don't necessarily think that if someone chooses to create a business and they're definitely after the money, they may just do it very rationally for a different reason.
Daniel:
[00:44:46 - 00:45:01]
Yeah, everything you're saying is so true in that. So I agree with you there. The money has to come to sustain the business. But there's a lot of fun in the business side of it. All of the things we're learning to build this business.
Anastasia:
[00:45:01 - 00:45:12]
So you mentioned Steve Jobs before, so I'm curious, his famous quote about stay hungry, stay foolish, what does it mean for you?
Daniel:
[00:45:12 - 00:45:16]
Personally, I agree with. I mean, that's one of the really smart things he said.
Anastasia:
[00:45:16 - 00:45:21]
But what does it mean for you? Because I found that people interpret it very differently.
Daniel:
[00:45:22 - 00:45:24]
I think it means, is it financial.
Anastasia:
[00:45:24 - 00:45:28]
Hunger, is it curiosity hunger? And what is foolishness?
Daniel:
[00:45:29 - 00:46:36]
I think it means just keep pushing yourself to grow and like, learn, experience new things and don't get complacent. You know, when water is like, still, it's not moving, but when you have flowing water, it's like always continually moving. You're learning. You shouldn't just be complacent with what the world is. You shouldn't just be complacent with who you are. I don't think people should just stay hungry and like, keep working. To just work, I think you have to find joy in life. And for me, like, learning is part of that joy. I think learning in general, the things that I'm curious about, is a joy. Like, I like that. So staying hungry means, like, for me, it's like continual learning about the things that you want to learn about, being curious about how to make the world better or your life better. But there's a caveat in there where, like, you don't want to just live to work. You need to find balance.
Anastasia:
[00:46:36 - 00:46:45]
So how do you do that, Daniel, today? How do you build a balance? That elusive work lifestyle balance?
Daniel:
[00:46:45 - 00:49:22]
I think it's never totally know you're not going to have this balance. You know, I've heard people say, like, work life integration, there's always a constant struggle, like, do I spend time working on this project? Do I spend time working on that for the company? You know, do I spend time with my son or my wife? Like, so you're constantly figuring out how to keep your life together, right? And there's no right answer because I think you're always ignoring one of the pillars that makes your life happy. Like, maybe you're ignoring, you know, what are other family members that you need to help. But, you know, some of the strategies that I've started for this company was this is going to be a pseudo remote company in some senses, where we're not just going to hire in one location. So for some of the employees of my new company, they have a really nice family life because they don't want to move away from their family. They wouldn't move to Silicon Valley, they never would. They want to stay where they're at. So, like, I see that they're having this better life because of, like, the way that we're designing this company. Um, I mean, it falls, you know, there's a waterfall effect. It's like, for me, it's the same thing where actively I wanted to have this remote company because it also helps me in the way that I operate, right? So, like, if I want to go to an event or if I want to Spend time with my family at night. I don't have to commute three hours to like, be home. So I design. I'm designing my life around, you know, working a lot, but also being able to see my family when I need to quickly. But, you know, I'm also seeing friends a lot more than my first company. So, like, I think I'm designing my life in a way where I'm like, I need to just carve out some of that time for like some of the friends that I have in my life. So I've been building in like walks at night with some of my friends. I've been meeting up with people a lot more than my first company because I'm like, if I don't do that, those friendships will die, right? They won't die. It'll just be harder to maintain them. So again, it's not perfect, but the reality is building a business is building a business and it just takes up abnormal amounts of your time.
Anastasia:
[00:49:22 - 00:49:26]
There are sacrifices for sure. So how much do you really work?
Daniel:
[00:49:26 - 00:49:34]
It ebbs and flows. Like, some days I'll work 15 hours, some days I'll work 4 hours, some days I'll work 10 hours.
Anastasia:
[00:49:35 - 00:49:38]
Is it approximately as much as with the first business?
Daniel:
[00:49:39 - 00:50:16]
Yes, I would say so. Like, the reality is if you don't push yourself, the business won't make progress. So like, it's this innate stress and it also comes like part of the structure of the design of this company. The DNA was let me get co founders who will push me hard. So like, if I slack, they will call me out. They'll be like, where are you? What are you doing? Get back to work. I love it because I'm like, this is pushing the business forward. I appreciate that. And I do the same with them where we're all kind of pushing each other towards the end goal.
Anastasia:
[00:50:16 - 00:50:22]
So on a scale from 0 to 10, how fulfilled do you feel?
Daniel:
[00:50:22 - 00:50:35]
Depends on the day. I would say a five. Okay, six. I don't know. It's, you know, it depends on the day. Some days I'm really happy.
Anastasia:
[00:50:35 - 00:50:37]
You need to get to 10.
Daniel:
[00:50:39 - 00:50:43]
I don't know. In your head there's always like this perfect place.
Anastasia:
[00:50:43 - 00:50:45]
Of course. And I'm like, that's fine.
Daniel:
[00:50:46 - 00:50:51]
I do. I don't think I'll ever reach that perfect place. You think it's there. You're like, if I get to dream.
Anastasia:
[00:50:51 - 00:50:56]
Of it, you can still dream of it. So do you know in your dream whether it's realistic or not?
Daniel:
[00:51:00 - 00:52:07]
I think that there's a lot of hills. So, like, if I climb this mountain and I'm like, I got through the mountain, then I see another mountain over that, and I'm like, let me get through that mountain and I climb over that mountain and then I'm like, let me get. I think that you're never actually satisfied even doing the thing you, like, want, which is just the innate nature of maybe me and, like, the human thinking, like, is there, like, a fully satisfied life? Enjoying the day, I think, is what makes it, like, nice for me. Like, it sounds so silly. Sometimes I wake up and it's like, go, go, go. Like five meetings in a row. Sometimes I have a really, like, relaxing morning, which I absolutely love, right? So, like, I'll wake up and I'll be like, okay, good. I have, like, think time. I love that. I love it when I, you know, again, a business is a business, like my calendar. I control it. But also at the same time, I'm really trying to work with other people, so I have to, like, work around other people.
Anastasia:
[00:52:07 - 00:52:11]
So something pushes you. So you control your calendar, but something challenges you.
Daniel:
[00:52:12 - 00:53:41]
Yeah, but you know, there are days when I have, like, a lot of joy, like, a good day. This is like a 10, a 10 day. It's like I spend the mornings walking my dog, have some coffee, spend a few, you know, a few minutes with my wife, see my son for a minute, a few minutes. He goes to school. And then, like, I have that baseline and then I go into work. And then it's just a great day because things are going our way. And you are always putting out fires at a company. So it's like, not every day works like that. But there are days when I wake up and I'm like, this was a really good day. Everything went the way we wanted it. And I just feel like a 10. And I'm like, this is a great day. Then there's days where just things are just happening. And you're like, okay, I didn't expect that. I didn't expect this. And, you know, you have like a 2, and you're just like, oh, man, that was just rough. And it could be, like, it could be personal, it could be work, you know, But I think it's like, enjoying the little things that I appreciate more. Some people have this, like, end goal in their head, and, you know, that's their. They're going to attain this and then they're happy. For me, it's like, my car didn't break down. Like, my car broke down last week, and I'm like, okay. My car's good. I feel good today. Or like, ah, that, that guy. So he bought our product today. This is great. Like, he's using it.
Anastasia:
[00:53:41 - 00:53:42]
Yeah.
Daniel:
[00:53:42 - 00:53:58]
Like, that totally makes a day worth, like, everything. Like, and, you know, I get these glimmers of just excitement from those things. So I think it's like, and this is maybe how I work long term. That's why I can do it so long is you look at, like, the little things to make your life happy.
Anastasia:
[00:53:59 - 00:54:03]
I think it's wonderful. I think it's such a wise approach. I love it.
Daniel:
[00:54:03 - 00:54:17]
Yeah. Yeah. I mean, you know, of course I have end goals, but I don't think that if I hit that, if I get that, I still don't think I will be a 10. It doesn't. You don't stay a 10. It's like, I've gotten that thing. It didn't fulfill me. It's like.
Anastasia:
[00:54:18 - 00:54:27]
So, Daniel, I'll ask you the same question I ask everyone at the end of the interview, which is, how do you want to be remembered?
Daniel:
[00:54:29 - 00:54:46]
I mean, I think for me, like, having my family, like, appreciate, like, the hard work that I put in, I think them missing me as opposed to, like, not right. I think, like.
Anastasia:
[00:54:48 - 00:54:52]
You want to feel needed. I love it. But your family.
Daniel:
[00:54:52 - 00:56:16]
Yeah. And I think, like, family is like, probably the most important piece of it. And I think, like, having good friends remember you and like the good times. But it is, it is kind of crazy. Part of the reason why I work on, you know, these companies is people don't remember you that fast. Like, your immediate family will remember you. They'll fondly remember you if you, like, take care of them. But like everyone else, really, they just go about their life. So it's like, I don't know if I'm going to have the Steve Jobs impact in the world, which is totally fine with me. You kind of just have to do what you want to do in your life and try not to let people judge you for what you're doing. I think that's more important to me. And just people remembering that that are in my immediate family and being like, okay, he did what he wanted to do in his life. One of my friends, it looks like he's going to be going through a divorce now, and he's a very wealthy guy. And I'm like, it's not the money. It's not making him happy. He's, like, miserable. He's not happy in his life. And it's like, you think when you have all of these resources you're just going to have this great life. Me and my wife sometimes go to the graveyard. We go to those graveyards down wherever we travel. This is a weird thing we do is we go to grave sites. And I can tell you, you know Hewlett and Packard, right? Hewlett Packard, the printers?
Anastasia:
[00:56:17 - 00:56:18]
Yeah, yeah.
Daniel:
[00:56:19 - 00:57:13]
I live down the block from their grave site. The same grave site that Shirley Temple is at, the same grave site that Steve Jobs is at. People don't, you know, their immediate family remembers them really like, Hewlett Packard's a printer to some people. But, you know, everybody is in the same spot. You had all of these billionaires literally next to people that are just, you know, that weren't ultra wealthy and that people didn't know. And their gravestones are so not different in the sense, like, you're all going to the same place and it's just all. You're all like. So it's like, just live the life you want to live and take care of, like, your immediate family and everyone around you and try to do good in the world. But I think over time, a lot of people are forgotten, which is sad. We all, like, are forgotten, but so live the life you want to live.
Anastasia:
[00:57:13 - 00:57:20]
This was probably the longest answer I ever got to this question, but it was fascinating. Thank you.
Daniel:
[00:57:20 - 00:57:23]
Awesome. Well, thank you for having me on. This was great.
Anastasia:
[00:57:23 - 00:57:28]
Absolutely. Daniel, thank you so much. I love the conversation. Hope to talk to you soon.
Daniel:
[00:57:29 - 00:57:31]
Yeah, that sounds great. Thank you so much.
Anastasia:
[00:57:31 - 00:57:53]
Absolutely. Bye. On this podcast, we are building a real post exit playbook together. If Today helped hit, follow or subscribe so you don't miss the next one. And please share it with one exited founder you care about. Thank you.
