Chris Bakke's Net Worth is $25-50M. His Goal? Being a Present Dad Over Building the Next Unicorn

We spoke with Chris Bakke on Moneywise. Chris is a successful tech entrepreneur who worked his way up to a net worth of around $25 million, though if you count the value of his Twitter stock, it's closer to $50 million. After selling two companies and working directly with Elon Musk at Twitter, Chris has shifted his priorities to focus on being a dad to his three children under three.

Like all Moneywise episodes, Chris breaks down his net worth, income, portfolio, and monthly expenses and then I, your humble host, pick it all apart. We also went deep on: what it's like working with Elon Musk, how having children changes your ambition, and balancing wealth with family priorities.

Below you'll find my summary of the episode along with the entire transcript.

And by the way...this podcast, the concept of it came from Hampton. Hampton is the community I run. It's a community for entrepreneurs and our members do $25M a year in revenue on average. And our main thing is hosting events and retreats for successful founders. Meaning, if you're an entrepreneur who wants to meet other entrepreneurs with similar types of companies, Hampton will help you out. It works for me, because this podcast provides me with entrepreneurs to speak with and it helps you all understand wealthy people. Win-win. New Moneywise episodes come out weekly.

Now, below are the notes and the full transcript.

The Numbers

• Net Worth: $25 million (or $50 million including Twitter/X stock)

  • Conservative value without Twitter stock: $22-25 million
  • With Twitter/X shares: $45-50 million

• Monthly Expenses: $11,000-$18,000 per month ($150,000-$200,000 per year)

  • Property taxes: $70,000 per year (nearly 50% of all other expenses)
  • School tuition, food, travel, etc.

• Asset Allocation:

  • Primary home: $6 million (paid in cash)
  • Second home in Minnesota: $1 million ($500k purchase + $500k improvements)
  • Investment properties: $4 million (syndicated office buildings, apartment shares)
  • Stock market: $5 million (mostly index funds, mutual funds)
  • Private companies: $5-10 million (LP in 7 different venture funds, mostly Y Combinator)
  • Cash: $2-3 million
  • Some cryptocurrency
  • Two agencies generating ~$1 million in annual cash flow
    • First agency: $450,000 in 2024 cash flow
    • Second agency: $600,000 in 2024 cash flow

• First Company Exit (Interviewed):

  • Sold for $52 million at age 27
  • Personal payout: ~$10 million first wire, followed by $6-7 million through earn-out
  • Net worth at age 30: ~$15-18 million after taxes

• Second Company Exit (Lasky):

  • Sold to Elon Musk/Twitter for $50 million
  • Deal structure: $10 million cash, $30 million Twitter stock, $10 million X.ai stock
  • Current Twitter/X stock value: ~$20-22 million (assuming $15 billion valuation)

From Ambition to Contentment: Chris's Journey in Tech

Chris Bakke's path to wealth began with a fairly standard tech industry trajectory. After a brief stint in private equity that he found "terrible," he moved to San Francisco in 2010, inspired by Hacker News and the movie The Social Network.

"I was like, I got to be in the center of what's going on up here. So I just like, packed all my shit. Moved up to San Francisco in 2010 and then got a job in sales at a startup, and then kind of kicked off from there."

His first entrepreneurial success came with Interviewed, a company he describes as "hackerrank for non-technical people" that assessed salespeople, marketers, and designers. Just two and a half years after starting it, he sold the company to Indeed for $52 million at age 27.

Rather than trying something completely new, Chris followed a proven formula for his second company:

"The second company was Lasky... basically just rehired the same engineering team. And it was a recruiting automation company. So like selling to very similar... Same shit. Different company. Yeah. Same team. Like six of the ten employee, like first employees from the first company came and worked with us at the second company. Same co-founder basically raised from all the same investors."

This strategy paid off when Elon Musk acquired Lasky for $50 million shortly after buying Twitter, with the goal of integrating it into his vision for the "everything app" and taking on LinkedIn.

Working with Elon: The Reality of Extreme Ambition

One of the most fascinating parts of Chris's story is his firsthand experience working with Elon Musk during his time at Twitter. Chris describes Musk's ability to context-switch between entirely different business domains as "insane":

"Like a good example is when we were selling to him... in those meetings, like I remember Walter Isaacson who wrote his biography, would be like shadowing him around Twitter. And so Walter Isaacson would be in this conference room, and he would have like 12 members of the Tesla finance team... he would just be like screaming at these guys over, like different delivery numbers... And then we would go in and basically talk to him about like how we're going to defeat LinkedIn. And then his assistant would, like pop into the conference room... They'd be like, uh, sir, like Ted Cruz is on the line. Like, do you want to take the call? And he's like, yeah."

This extreme level of multi-tasking and the intense work culture had a profound impact on Chris's perspective. While he acknowledges the potential financial rewards of Elon's ambition, he also witnessed the personal costs:

"The sacrifices that he's given to, you know, his relationships and his family. I think you see that in a lot of super successful people where you only have so many hours in the day. And so if you're running seven different companies and jet setting the entire world and everybody needs you at all times, you just don't have that much time to give your spouse or your kids."

How Children Changed His Ambition

Having three children under the age of three has completely shifted Chris's priorities:

"Having kids is like it completely rewires your brain. It rewires, I think everything about where you live, for sure, like, where do I want them to grow up?... I think everything in my brain got rewired."

Chris openly acknowledges that his professional ambition has changed since having children:

"I for sure agree on the drop in professional or work ambition. Like, I think that before a kid you're able to jump on, like if you need to eat dinner with your, your spouse and then you need to jump back online from 7 p.m. and 8 p.m. or 9 p.m. and send a bunch of emails and do a bunch of stuff. You're like, okay, I feel like I'm productive in doing this, but then you have a kid and you're like, well, you know, 7 p.m. is bath time, and then 8 p.m. is bedtime, and then they wake up at 9 p.m. because they're scared and like, you just don't have that window."

Rather than seeing this as a negative, Chris has found contentment in shifting his priorities:

"I enjoy spending time with her and like, you know, dropping my son off at preschool and like doing all these little, like, fun things as a dad."

He believes that this change in ambition has come proportionally with each additional child, and he's comfortable with that trade-off.

Finding Balance: Small Projects vs. Moonshots

One of the most relatable aspects of Chris's current approach is his pivot toward smaller, cash-flowing businesses rather than high-risk, high-reward startups:

"I want to be ambitious in the sense of like using my brain is fun, but I also want to work with interesting people. I want to enjoy the work that I do, and I just like running a small agency that ghostwrites for a bunch of people a lot more than I enjoy like running a big product org and like having to do everything that Elon needs me to do in a 24 hour period."

Chris challenges the conventional definition of ambition in the tech world:

"I've now seen, you know, enough founders go through YC and they raise millions and millions of dollars and they basically do zero revenue. And then they shut down. And that feels like an ambitious thing. But like running an agency or running a bootstrap business that does one, two, five, 10 million like isn't ambitious. I don't really buy that."

He's found joy in unexpected places, like starting a Whatnot channel for rare coins and currency that made just $500 in profit but provided genuine enjoyment.

Financial Comfort and Its Impact on Parenting

With a conservative net worth of $25 million and monthly expenses of only $11,000-$18,000, Chris has created a life that prioritizes financial security while allowing him to be present for his family. He sees this as a significant advantage in parenting:

"There is a huge divide in my friend group between people that are still like, especially in the Bay area, that are just like grinding to stay head above water... Both parents are working, but they have 2 or 3 kids. And it's like our son's preschool is $1,000 a month. Each additional kids preschool is going to be $1,000 a month... I think having a nice base of many millions of dollars where you don't have to feel like every little decision you're making is killing you financially. I think that that would be really hard as a parent, and that's for sure the way that 99% of parents are living."

Other Key Quotes

On what changed his life more, having kids or financial liquidity:

"Having kids for sure, without a doubt... Having a bunch of liquidity meant that we were able to go from a one bedroom apartment in San Francisco to, like, a five bedroom house in the East Bay and live the nice suburban life. But like outside of that, things day to day didn't actually change."

On his approach to wealth:

"With personal burn of $15,000 a month across a family of five... I'm not a huge car guy. I've never flown private. I don't want a yacht. And so it just feels like we have like a really nice house that I enjoy. We have many, many millions of dollars in the market and a few million dollars in cash where we can go buy anything that we need to at any point."

On the emotional impact of sudden wealth:

"It was awesome for like two weeks for sure. And even though I'm not a car guy, like, bought the cars and like, we bought a house all cash and like, did some like stupid financial stuff. But like after that you have like 8 or 10 million in the bank and you're just constantly watching it, which is kind of a unfortunate way to live, I think."

Links You Might Like

• Chris' Twitter

Full Transcript

[00:00:06] Chris Bakke: So I just like, packed all my shit. Moved up to San Francisco in 2010 and then got a job in sales at a startup, and then kind of kicked off from there.

[00:00:13] Sam Parr: Chris Bakke wanted to be the center of the tech world, and he actually almost made it there.

[00:00:18] Chris Bakke: Like a month after Elon bought Twitter. Elon bought Lasky and then merged it into Twitter and then like, formed X.

[00:00:27] Sam Parr: Chris worked his way up to a net worth of around $25 million, though if you count the value of his Twitter stock, it's closer to $50 million. The reason? He's got three kids under three. And by the way, those kids, they are not twins, so that's one after the other.

[00:00:41] Chris Bakke: So we have a two month old, one and a half year old and a three year old.

[00:00:46] Sam Parr: And so Chris's life. He's shifted it to optimizing for being a dad. And his drive for business success is not what it used to be. And that sounds like I'm insulting Chris. I'm not at all. I compliment him a ton and I think he's an amazing person. But what I mean is, after I had kids, frankly, I became less driven and I think Chris did as well. The good news is that Chris admits this and he acknowledges this, and he's genuinely happy and content with his life. And I'm envious of that. And I wanted to sit down and figure out how he thinks about that, because, frankly, a lot of people who have children, their ambitions change. And I think that's scary. And also in this episode, you see, Chris actually worked directly with Elon Musk when he was taking over Twitter. And so we're going to get a lot of insights on this. And if you're new to money wise, welcome on this podcast. I get wealthy people. So people who are typically worth $20 million plus and I get them to break down their portfolio, their monthly income, their expenses and all these numbers that typically are never transparent. And better yet, I'm actually going to talk to them about different problems and things they've got going on in their life and how they're solving them. And by the way, the reason I know about all these issues and the reason I know a lot of these people is I run this thing called Hampton. Check it out. It's called Join Hamptons.com. It's a community for entrepreneurs. The average entrepreneur in our community does something like $25 million in revenue. And so there's a ton of high net worth people. And so I'm able to see all these conversations that happen behind closed doors. And I thought it would be kind of cool if I made this into a podcast. And that's what Moneywise is. So all right, so let's get right into the numbers for Chris. What's like your net worth now?

[00:02:23] Chris Bakke: 50% of it is dependent on what you think Twitter or Z is worth. And so I think the conservative value like if you just take all of that stock out like 22 or 25 million, if you add that those shares in, it's like 45 or 50 million, and.

[00:02:39] Sam Parr: Are you spending a lot per month?

[00:02:41] Chris Bakke: No. We have pretty low personal burn. So we don't we don't have a mortgage on. We have two houses. We don't have a mortgage on either of them, which helps a lot. Uh, so like California property taxes are brutal. So we spend $70,000 a year on property taxes, which is almost it's about 50% of what we spend on all the other stuff. So we spend, I think about somewhere between 11, 11,000 and $18,000 a month, just dependent on school tuition, food, going out. Some travel here and there, but it's pretty low. It's like 150 to $200,000 a year outside. It's not a lot.

[00:03:18] Sam Parr: That's not a lot. And then of the 20 to 25 that is not Twitter stock. How is that allocated.

[00:03:24] Chris Bakke: Yeah. So it's we bought this house that I'm in now in the East Bay for 6 million cash about a year ago. We have another a second home in Minnesota that's like a lake house next to my in-laws that we bought for half a million. And then we put about another half a million into it. Let's call that a million. I have about 4 million in investment properties, uh, so own different shares, mostly through Twitter. People like different syndicates of office buildings in Dallas and little shares of apartments and Annapolis, and just sprinkle some money here and there. I have around 5 million just in the stock market. So mostly across like index funds, mutual funds. I used to do a lot of individual stock picking in 2020 and 2021 when when I thought I was a genius. I own no individual stocks anymore outside of, I think, Zillow stock, because they bought my first company and I kept a bunch of the shares over the last ten years, which has been good, but no individual stocks, and then have somewhere between like five and 10 million parked into some mix of private companies. So mostly as an LP in seven different venture funds. So Y Combinator is the vast majority of that.

[00:04:41] Chris Bakke: So it became an LP in YC. I think eight years ago when I sold my first company, and so have been able to get into a lot of fast growing companies because of that. And then I also keep a ton in cash, like probably way too way too much in cash. So I think I have like 2 or $3 million in cash on hand right now that I'm just sort of like waiting to deploy either into personal companies or investments. And then a little bit in crypto. And I don't really count the value. I own two agencies that throw off about, I think in 2024, one threw off like 450,000 in cash flow to me. The other one threw off like 600,000 in cash flow to me. But I think agencies are sort of hard to value. Like each of those companies does around $2 million in revenue and ah, you know, hopefully both going to grow this year. But I don't really count that. And so that's where a lot of the cash comes from is like, I have cash coming in from dividends and from investment properties and from the agencies. And I just sort of sit on it until I find something interesting to do with it.

[00:05:41] Sam Parr: I have a lot of questions. First of all, that allocation is wild. That's different than how I do things. And I want to know, are you happy with that allocation? If you knew what you knew now and you could redo it, is that exactly how you would do it? How it is now?

[00:05:55] Chris Bakke: I'm trying to put more into the stock market, so I would love, I think a lot of that, like 2 or 3 million cash on hand, will probably go into just into more index funds like I, I've been super happy with the returns that I've gotten in the stock market over the last ten years, since I've been putting serious money into the market. Yeah, I mean.

[00:06:13] Sam Parr: It's been like one of the best bull runs of all time. So it's easy to say, yeah, yeah.

[00:06:18] Chris Bakke: So it's like maybe, maybe having more there would be good. I do feel very overexposed to small private companies for sure.

[00:06:26] Sam Parr: Well, that's what I was going to say was you have a lot in privately held things of which you have little to no control of, and they're illiquid. Yeah. But they are potentially moonshot or, you know, whatever you want to say Twitter is, is that a moonshot or not? Maybe. Potentially for sure. Why? See, I don't know which companies you're in, but historically that's a great investment. But it's just illiquid. But it is moonshot I guess. And then In real estate, that's pretty safe, but it's still also illiquid.

[00:06:56] Chris Bakke: Yeah, I think my my take on this is like with personal burn of $15,000 a month across a family of five, and we also have a full time au pair that that lives with us. And she's been with us for like two years and is sort of like part of that mix of, you know, needs a car and food and all that kind of stuff. It's like I just have no, I'm not a huge car guy. I've never flown private. I don't want a yacht. And so it just feels like we have like a really nice house that I enjoy. We have many, many millions of dollars in the market and a few million dollars in cash where we can go buy anything that we need to at any point. And then beyond that, I think one of the things that I saw from working for Elon was like, I don't have big desires to go be a billionaire. I don't really have the desire to fly private or like, we're not going to be chartering yachts in the Mediterranean with three kids. So it's like, as long as we have enough to, like, cover their tuition bills and like send them to summer camps eventually and keep buying food and like, do a couple vacations a year as a family. Like I'm fine having like a really long time horizon on stuff that I feel like is going to outperform the market or some of my individual companies. So it's a pretty boring allocation overall, but it definitely makes me sleep well at night knowing that, like the companies that I start or even like the agencies that I've started, are sort of the more like risk adjusted bets here that are going to throw off cash for the future.

[00:08:15] Sam Parr: So that's what he's doing with his money. But let's talk a little bit more about how he came to have it.

[00:08:20] Chris Bakke: I started in private equity out of college. I did it for a year. It was terrible. And then learned enough about tech from like, I was just following Hacker News. Like, I feel like it's super common. I was like, the guy that, like, read Hacker News all the time, and I, like, saw the Facebook movie, like The Social Network. And I was like, I got to be in the center of what's going on up here. So I just like, packed all my shit. Moved up to San Francisco in 2010 and then got a job in sales at a startup, and then kind of kicked off from there.

[00:08:46] Sam Parr: What was the first company you started?

[00:08:48] Chris Bakke: It was interviewed in 2015, so worked at two startups and then started interviewed. We went through YC with it and then yeah, it was like an assessment company. So we were assessing it was sort of like hackerrank for non-technical people. So it was like hackerrank, but for salespeople or marketers or designers. And then that was the company that indeed bought and spent a lot of time in Austin because of that.

[00:09:12] Sam Parr: How soon after starting it did you sell.

[00:09:15] Chris Bakke: Two and a half years later?

[00:09:17] Sam Parr: Wow. That's fast. And what did what did you raise, like $1 million?

[00:09:20] Chris Bakke: Yeah, we raised 1.7, 1.82 50 of it was from YC. And then the rest was like a bunch of random angels and then sold to indeed kind of got to know, indeed, because they were a small investor and then spent a bunch of time with them and then eventually exited to them.

[00:09:35] Sam Parr: Were you making any revenue?

[00:09:37] Chris Bakke: Yeah. I mean, I was actually like a pretty, I think, for not starting a company before we did a good job. It was all pretty much founder led sales, like a ton of hustle into cold email showing up at up at people's offices like less frowned upon back in 2015 than it is today. So we would just walk around San Francisco, like, write down the nameplates of all the buildings, and then I would like look them up in, yes, male, which was like an early, like HubSpot plugin type thing. And then I would just email the CEO and be like, dude, I'm down the street, let's get lunch, let's get coffee. So it was like very much like outside sales, even though we didn't know it. Outside sales was. And so we I think we were doing 2.3, 2.4 million IRR when we were bought.

[00:10:16] Sam Parr: And did you have any partners?

[00:10:18] Chris Bakke: I did, I had two co-founders.

[00:10:19] Sam Parr: So three of y'all what did you sell for?

[00:10:21] Chris Bakke: 52 million.

[00:10:23] Sam Parr: Which is a shitload of money. Yeah. How old were you?

[00:10:26] Chris Bakke: I was 27.

[00:10:29] Sam Parr: Wow. I mean, that's a ton of money. You just. That pie breaks up a lot.

[00:10:32] Chris Bakke: Yeah, I was on my honeymoon when we sold, so I was, like, in Spain. I was just, like, refreshing. Wells Fargo I feel like everybody that sells a company has this, has this moment at some point. Like, it's the same kind of surreal experience, but it's like sitting in, like, Barcelona in some In some hotel being like, we could be in a way nicer hotel right now when this wire hits. But you're just like, you don't really know when the transfer is going to hit. They're like, yeah, within 48 hours. But that's like a long 48 hours.

[00:10:56] Sam Parr: Yeah. I remember going to the bank in advance and I was like warning them. And I was like, you know, multiple eight figures are going to come to the bank account. I'm not a drug dealer. And they're like, yeah, dude, we don't care. We're chased like, yeah, yeah. We're like the biggest bank in the world. Like, who gives a shit about you? Yeah. Uh, how much did you end up making at 27?

[00:11:13] Chris Bakke: I think the first wire was like, right under 10 million. I think it was like eight something. And then through the earnout, I stayed three years. I think basically after taxes netted another like 6 or 7 million in the, in the earnout.

[00:11:27] Sam Parr: So after taxes you would have been like at the age of 30 and worth like $18 million or something.

[00:11:34] Chris Bakke: Something like that, like 15 I think. Yeah.

[00:11:36] Sam Parr: I mean, that's a lot, right? How did that feel?

[00:11:38] Chris Bakke: It was awesome. But it was also, um, I think it's such like a rich first world problem. But I think everybody talks about the idea of like past a certain point. You don't know what to do. Like you're like, should I manage my own money? Am I, like, screwing my like, should this all just sit in like a betterment account? Should I just put this in Wealthfront? Like, should I be doing I need to go to Goldman with this. And like, you meet with Goldman Sachs and you're like, dude, we don't care about like $15 million. And then you're like, well, if I go with a wealth manager, are they just going to screw me on fees? And you like, read all these horror stories about people that, like, manage their own money and lose it all. You read stories about people that give it to a bank and they lose it all. And so I'm just like, how do I not lose it? And then it became this, like kind of sick game about just like constantly checking like E-Trade and Vanguard and Fidelity and like it was awesome for like two weeks for sure. And even though I'm not a car guy, like, bought the cars and like, we bought a house all cash and like, did some like stupid financial stuff. But like after that you have like 8 or 10 million in the bank and you're just constantly watching it, which is kind of a unfortunate way to live, I think.

[00:12:39] Sam Parr: How much house did you buy?

[00:12:41] Chris Bakke: We bought this house in Black Hawk. Like our first house for 2.25 or 2.4. Something in there?

[00:12:49] Sam Parr: Oh. That's not. I mean, you could have spent maybe more if you wanted to, right? I mean, a lot more.

[00:12:53] Chris Bakke: Yeah, I was I was just scared, like I've heard, like buying a house in all cash is dumb. But I also I was like, just had gotten married. So I wanted my wife to feel like she had, like, a more comfortable life. So I was like, people were like making fun of me because I, like, bought a house in all cash versus getting a mortgage. And I was like, but I don't want a mortgage because it makes my wife happy. And so, I don't know, there was a weird dynamic of just like, I've never had this much money. I was renting an apartment in San Francisco. Like, how does one live with this amount? It was strange.

[00:13:20] Sam Parr: There's something really funny about Chris's story, which is he made roughly $7 million on that sale, but he wasn't done yet. You see, the interesting thing is this instead of trying to find something new, something fresh, or make a bunch of money investing, Chris just looked at the business that he had launched before the business that worked, and he thought, well, that's kind of a winning formula. It's a winning product. It's a winning business model. I'm just going to going to repeat this business. I'm going to do it again.

[00:13:44] Chris Bakke: The second company was Lasky, so I started it with one of my one of the two co-founders that I started the first one with, and we basically just rehired the same engineering team. And it was a recruiting automation company. So like selling to very similar.

[00:13:58] Sam Parr: The same shit.

[00:13:59] Chris Bakke: Same shit. Different company. Yeah. Same team. Like six of the ten employee, like first employees from the first company came and worked with us at the second company. Same co-founder basically raised from all the same investors. But it was 2020, so they were giving us like four times the amount of money that they were back in 2015 the first time. So like getting things going was like ten x easier.

[00:14:21] Sam Parr: And just like the first time, it worked really well for him. But there's a twist.

[00:14:26] Chris Bakke: Like a month after Elon bought Twitter. Elon bought Lasky and then merged it into Twitter and then like formed X. And so we were this like tiny minuscule part of like the big vision to become the everything app. And so because we had all of this recruiting and hiring data, he was like, I want to go after LinkedIn. And he didn't have LinkedIn money, but he had $50 million to go buy Lasky. So that's that's sort of what happened there.

[00:14:54] Sam Parr: That was the price 50 million.

[00:14:56] Chris Bakke: Yeah.

[00:14:56] Sam Parr: Yeah. What was the breakdown? I mean, did he offer you any Twitter stock or is it 50 million cash?

[00:15:01] Chris Bakke: It was pretty 50 over 50. Like, I actually, I felt like in acquisitions before, like from the startups that I worked at and from my first company, I think if we would have taken Indeed's stock versus all cash, like it would have been worth a ton of money. I think a lot of companies that are selling to a or a lot of founders maybe that are selling to a fast growing company. It's like, I want to de-risk and take a lot of cash. But I think at the end of the day you're probably better off. And so we ended up taking.

[00:15:26] Sam Parr: Better off if you take stock. You're saying.

[00:15:28] Chris Bakke: Yeah, I'm better off if you take stock. Yeah, yeah. And so because it was an Elon company and I felt like the valuation of Twitter when he bought us was super compressed. I wanted to wanted to maximize the stock. And so I think the breakdown was 10 million in cash. It ended up being about $30 million in Twitter stock and 10 million in X.ai stock. We were also then vesting like I worked there for a year and a half. So we were also upper managers at a company. You're making a couple million dollars in shares in a private company that you also can't sell. So I think like I personally own, if you say that X or Twitter is worth like 15 billion, I think I own like 20 or $22 million in X stock right now.

[00:16:17] Sam Parr: Now a lot of you who are listening, who have got children, you are listening to this because you want to get to the kids stuff about money and children. We're gonna get to that, I promise. But the Twitter stock thing that's really interesting, especially considering how much Chris has of it. Also, Elon is a very unpredictable guy, even more so recently. And so there's a lot of different opinions on his businesses and how to value them. I mean, Elon has built Tesla, which is a very valuable company, but he's kind of a loose cannon. And so, you know, his business with Twitter, it might be worth a ton of money or it could be worth next to nothing in a month. Who knows? And just to reiterate, Chris owns $25 million of Twitter stock. Now, I asked him how he felt about owning stock in an Elon company, and he's feeling okay about it.

[00:17:05] Chris Bakke: I think, you know, we're way up on the on the Z component of that just simply based on like fundraising because we basically were granted shares at effectively the seed stage where the seed stage is like they had only raised 300 million and now they've raised like 15 billion. So on paper, like the Z stuff is way up and on paper the Twitter stuff is like it's either probably worth zero or a lot of money. And I also think like that's fine. I think the good thing about Twitter from a like shareholders perspective Div is. Ellen brought all of his friends into the deal. So Andreessen Horowitz, Sequoia, like everybody who's ever backed an Elon company, is in Twitter and I. And so I think he has a history of like not disappointing shareholders. And I think he's very determined, given all the like public and private scrutiny of like what he's done at Twitter to make this eventually worthwhile. And the way that it may end up being worth a lot of money is that they just become like a massive data repository for X.ai. And they just like train X.ai based on Twitter and like Twitter, becomes a reasonably valuable aspect of X, Y and Z becomes a huge company is probably what I think the outcome is.

[00:18:16] Sam Parr: Was working with him as crazy as it seems?

[00:18:19] Chris Bakke: Yeah, yeah.

[00:18:20] Sam Parr: For what reason?

[00:18:22] Chris Bakke: I think it's talked about a lot. Like if you've read his biography, I think his ability to context switch is insane. And I also think he just he has these like.

[00:18:31] Sam Parr: What if context switching mean.

[00:18:33] Chris Bakke: Like a good example Is when we were selling to him. He did the acquisition personally because he had fired the whole corp dev team. So there was no like traditional like corp dev like welcome to Twitter. It was Elon being like, I don't know, get to work. But in those meetings, like I remember Walter Isaacson who wrote his biography, would be like shadowing him around Twitter. And so Walter Isaacson would be in this conference room, and he would have like 12 members of the Tesla finance team, and we would be standing outside of this conference room, and we could kind of hear the meeting, and he would just be like screaming at these guys over, like different delivery numbers and like, get your shit together. This is ridiculous. And then we would go in and basically talk to him about like how we're going to defeat LinkedIn. And then his assistant would, like pop into the conference room while we're talking about how we're going to defeat LinkedIn right after he's been like reaming the Tesla finance team about like Chinese car deliveries. And they'd be like, uh, sir, like Ted Cruz is on the line.

[00:19:29] Chris Bakke: Like, do you want to take the call? And he's like, yeah. And he's like, just talking about, like, how to get Trump elected for like 15 minutes. And all of this is in the in the span of like 45 minutes. And you're like this guy, you know, literally goes from like digging tunnels to Neuralink, which is like brain chip implants to launching rockets into space to colonizing Mars, to electric car deliveries, to he was working on, like, Tesla Solar a bunch at that point to running Twitter. It's like he doesn't actually sequence his days. I think in a way that makes logical sense, like he just jumps from thing to thing and then plays like a shitload of Diablo in between. And so it's like wild to see somebody who can actually, like, pretty fluently talk about LinkedIn, although it's like 15 minutes of his day, like, here's how we're going to go defeat LinkedIn. Here's how we're going to go defeat YouTube. Here's how we're going to get like the next rocket into space. It's very jumpy. It's crazy.

[00:20:24] Sam Parr: Chris spent a year and a half working for Elon at Twitter, but this is when his life started to change. He had started his family and the contradictory lifestyle of working for Elon and wanting to be a good dad. They were not meshing well.

[00:20:39] Chris Bakke: It's not easy working for Elon, man.

[00:20:42] Sam Parr: You gotta grind.

[00:20:43] Chris Bakke: Yeah, it's a grind. And I think, um, you know, a big part of it was we had our second kid right at the start of the acquisition. We had our third kid, or we were about to have our third kid, like, right after a year and a half of working there. And so, like, having three kids under three and running to, you know, meetings in New York with Elon to like, go save a customer relationship or like flying to Austin and being in San Francisco in the office. It's just a lot. And so I think it was really fun. It was a super valuable experience for that year and a half and learned a lot through proximity. But it was just totally a grind. And so I think, uh, at that point in my life, six months ago, I was just like, I want to focus more on a relaxed pace of business. Like, I don't really care about chasing where the next million dollars is coming from? I really wanted to do work that was flexible so that for me that meant like working remotely or semi remotely or at least having like the freedom to sort of travel when I wanted to. And so all those things just became like a top priority versus like, how do I rise through the ranks of Twitter, which seems like a hard job?

[00:21:53] Sam Parr: Working with someone like Elon or someone in that ballpark can make anyone feel small. And when I hear these stories, it's kind of weird. Part of me definitely thinks about my own drive, and I actually kind of feel guilty sometimes about not pushing myself a little bit harder. Like my last company was The Hustle. I ended up selling it for a lot of money and it worked out for my life. But it was just a newsletter business. It wasn't some like big trillion dollar company or something where I was trying to go to Mars. And because of that, every once in a while when I hear stories about these super ambitious guys, it kind of makes me feel a little bit guilty for not being more ambitious. Us. But lately Chris has shifted to really love smaller scale projects. And this is something, by the way, that I empathize a lot with. And Chris actually stepped back from a lot of the high stakes grind that he used to do, some of these startups that maybe don't make a lot of cash flow, but you can sell them for a lot of money. He actually began to focus on really smaller projects that make a lot of cash up front or each year, and I wanted to know about that decision of focusing on some of these cash flow businesses that maybe don't require too much work and maybe aren't like some huge moonshot ideas. And if it makes him feel guilty.

[00:23:05] Chris Bakke: I have at times for sure, like it's one of the agencies I own. Like we go straight for founders and some of those founders. It's like there are times where I'm like, I would love to have that person's life because he just raised $180 million series A like, that's amazing. And then I'm like, yeah, but the work that it took like, I know this from starting companies, you know, this from starting, you know, venture backed companies and going after like competitors in like a super fierce way, just like the sacrifices that you have to make. I just think past a certain amount of money. I've been I want to be ambitious in the sense of like using my brain is fun, but I also want to work with interesting people. I want to enjoy the work that I do, and I just like running a small agency that ghostwrites for a bunch of people a lot more than I enjoy. Like running a big product org and like having to do everything that Elon needs me to do in a 24 hour period, just like having that control over my time. It's sort of, I think is a good sacrifice for the ambition. Like, I don't I don't think about the fact that I'm not super ambitious because I think, like you said, it's like if you've, you know, built and sold a couple of companies before the age of 35, like, I've sort of like checked that box, it feels like over my life. And now I do just want to chill for a little bit.

[00:24:21] Chris Bakke: And I think it's totally possible that, like, once my kids get a little bit older, like I'm very much in the thick of it, like I'm getting Pooped and peed on by our two month old every day, and so it's hard to context switch from that into like, let's crush the market and like, build some. I think it's like I enjoy spending time with her and like, you know, dropping my son off at preschool and like doing all these little, like, fun things as a dad. I think it's possible once they're all in school and I just have a lot more time on my hands, I will feel unfulfilled by how I'm spending that time and I'll want to do something. Quote unquote, more ambitious. But I also think, like, you know, with you and Hampton or with me in like the Twitter Growth agency. It's like I've also seen the opposite side where I've now seen, you know, enough founders go through YC and they raise millions and millions of dollars and they basically do zero revenue. And then they shut down. And that feels like an ambitious thing. But like running an agency or running a bootstrap business that does one, two, five, 10 million like isn't ambitious. I don't really buy that. So I think that balance of like, just because you've raised venture, just because you're working on something in AI means that you're ambitious. I just it doesn't really compute to me.

[00:25:24] Sam Parr: I also think a lot of those people will make a whole lot less money than you have, probably, and be a lot more miserable. Were you ever like, eh, let's take over the world, let's get after it type of guy? Or were you always this way?

[00:25:36] Chris Bakke: I was like, I think in college I was, or maybe even at like the first startup that I started, I think I was like that a little bit. And then I was like, yeah, sales is pretty hard. Hiring is pretty hard. Like, I would read all the, like, Fast Company and Inc. 5000 list and be like, I'm going to end up on one of these lists someday. And then I've met, you know, a couple of the people who've been on those lists and like, dude, you just pay like $5,000. They're fucking frauds, you know? And I was like, okay, like, I don't really care about the list anymore. I don't care about, you know, I've missed Forbes 30 under 30. I think I'd end up in jail if I ended up on Forbes 40 under 40. So it's like, you know, those lists are all like, you know, pay to play. I don't care about, like, the professional external accolades. I like making money. It's fun to try to use your brain to make money on the on the internet. Like that's always satisfying. But like, one of the more interesting ways that I made money in 2024 is I started like a whatnot channel, like the live shopping, live selling channel, like Ecom Channel. And I made like $12,000 of revenue in the month of December and like probably $500 in profit. But I really, really enjoyed it. Like I was like, oh, this is fun. Rare coins and currency.

[00:26:49] Sam Parr: That's awesome. Yeah, dude, I'm you and I are really similar. I'm like obsessed with vintage clothes and.

[00:26:55] Chris Bakke: Like, oh.

[00:26:55] Sam Parr: Nice. So often I tell my wife I'm like, dude, fuck this internet bullshit. I just like, honestly just want to go thrifting and find treasures and put it on eBay.

[00:27:03] Chris Bakke: It's fun. I am not a well-dressed guy by any stretch of the imagination, but I sometimes get like sucked into like the YouTube rabbit hole of those people that like thrift. So fun. And they'll be these like 19 year old kids and they're like hitting these like, flea markets and like, I bought 50 shirts for two grand and I flipped them for 2200. And I'm like, you go, man. I'm like, wait, he made $200 for $200 for a day's work. That's not very good. And if you or I were doing it, we'd be like, oh, my God, this is like a massive waste of our time. But it's pretty fun to, like, think about that stuff.

[00:27:30] Sam Parr: It's super fun. You know, I have this little thing called Copy That. And it does like a quarter of a million bucks a year in revenue. I spend no time on it, but like, I'm like, all I want to do is spend time on this. And like, the money that I make from that, I get more joy out of that than I have out of running other things that make eight figures. Totally. It's just like it makes me happy. I want to ask you about children. When I had a kid, I found myself way less ambitious. And I have a sense of guilt around that, but also a sense of, um. Man, life was a lot easier when I. It was a lot more straightforward when I just wanted to go out and kill people every day now. Now I just don't know. I just don't care.

[00:28:14] Chris Bakke: Yeah. Yeah.

[00:28:15] Sam Parr: Did that change for you when you had children?

[00:28:18] Chris Bakke: I for sure agree on the drop in professional or work ambition. Like, I think that before a kid you're able to jump on, like if you need to eat dinner with your, your spouse and then you need to jump back online from 7 p.m. and 8 p.m. or 9 p.m. and send a bunch of emails and do a bunch of stuff. You're like, okay, I feel like I'm productive in doing this, but then you have a kid and you're like, well, you know, 7 p.m. is bath time, and then 8 p.m. is bedtime, and then they wake up at 9 p.m. because they're scared and like, you just don't have that window. You know, after maybe your 9 to 5 anymore. But I also think that a lot of that for me, looking back, I'm like like a lot of that was just work for the sake of work. Like, I didn't have anything better to do and I didn't really like watching TV shows. And, you know, we would like, go out to nice restaurants to eat when I was like, dating my wife and stuff. But like, beyond that, like, you just sit around or like go to a bar or something.

[00:29:08] Chris Bakke: And I wasn't, I wasn't ever super interested in that. And so it was like, well, if I like, sit here and like sit my ass in the chair and I just send a couple more emails or I, you know, like do a late night meeting at like, makes me feel good. But it didn't like, was that actually moving the needle? I mean, maybe to a certain extent, I think working hard, especially in your first company to make it successful is like valuable. But I think for me it's a balance. Like, I think I want my kids to grow up knowing that both of their parents, like, worked very hard and that their dad worked super hard and like, having a nice house, like, just doesn't come super easy. And so but it's hard. Like, I don't know in terms of the nature versus nurture, like how much of that they will actually understand is like really hard to say. And so yeah, I for sure think the ambition dropped after our first kid. And I think it's dropped. I think it's dropped proportionally with every additional kid, for what it's worth.

[00:29:58] Sam Parr: Now going back to being in the same room with Elon or someone like Elon, a lot of Chris's growth and contentment with his life. He says that it comes from what he learned with Elon, which is that it's very easy to be jealous of someone who has billions of dollars or is super powerful if you don't really know them. It's kind of easy to feel that envy. But when you take a take a closer look at that person's life, things change.

[00:30:22] Chris Bakke: The money games seem very different at like a business level. Like when I was getting off the ground, I remember this one email that I was copied on that. Like it just blew me away. Like a couple of the engineers were like, hey, Elon. Like, I feel like we're falling behind. I don't even remember who it was, if it was OpenAI or perplexity or something like that. Like we need to get like more GPUs up and running ASAP. And Elon's like, how much do we need? And they're like, we want to buy like $350 million worth of GPUs. And we want like to spend an extra $40 million to have the like Taiwanese manufacture expedite it. And he just replied, okay. And that was it. That was like a $400 million decision that was done over like 3 or 4 emails. And so I think at the business level, like the money, that's.

[00:31:03] Sam Parr: Like a $10,000 thing for you maybe, or.

[00:31:06] Chris Bakke: Yeah, yeah. It's like, hey, Sam, like I want to I want to like, upgrade to like first class on this flight. And you're like, okay, it's a long flight. You deserve it. Go do your thing. The way his assistant put it, uh, I'm not sure if this number is true, is true, but when we first joined Twitter, she's like, hey, just remember, Elon's companies collectively do $20 million in revenue per hour. So if you grab an hour on his calendar, just make sure it's like a $20 million decision or more. And I was like, it's kind of a weird way to look at it, but I like it. Uh, and so I think at the business level, like, that's insane to think about like that, pretty much everything that he's doing has to be I think, you know, Elon is a very like zero sum person. Like, this is either going to go to zero or it's going to be the biggest company in the world, and there's not really an in between. And so he didn't care about like building an average sized social network. Like he wants to build a social network that crushes all others and goes and dominates PayPal and YouTube and all these things like very, very, very ambitious.

[00:32:02] Chris Bakke: But in his personal life, like he's making these decisions while living out of a 400 square foot house in Starbase, Texas. That's a two bedroom, one bath because he, like, got rid of all of his personal belongings and, and homes and all and all this other stuff. Now he's like bought like a 6 or $7 million house in Austin, I think since then. But it's like, okay, he's worth $300 billion, I'm worth $30 million. And we both live in a $6 million house at the end of the day, like, yeah, he has a sick jet. It's really nice. But like, he only uses that. It's not like he's going anywhere interesting. He's using that jet to go fly to Dubai to go raise more money for SpaceX. He's using that jet to go fly to France, to go, like, spend all day meeting different European government officials and begging them to not ban Twitter like he's just running around the world asking people for favors, shaking hands, kissing babies. And I kind of realized like that. I don't need that. It actually is super stressful, I think, to live that way. I think he does a really good job of balancing all that, but I think that.

[00:33:04] Sam Parr: He does a horrible job of balancing that. But he's okay with that.

[00:33:07] Chris Bakke: Yeah, for sure. I mean, the sacrifices that he's given to, you know, his relationships and his family. I think you see that in a lot of super successful people where you only have so many hours in the day. And so if you're running seven different companies and jet setting the entire world and everybody needs you at all times, you just don't have that much time to give your spouse or your kids. And ultimately, that decision is like way more important to me to invest like time and resources there than it is to be like running around on a $85 million jet.

[00:33:39] Sam Parr: Now, I think there is a balance of being a go getter, ambitious person and having drive, but also still being a great father, being present and not being overworked because life without some type of ambition, it can feel super empty. Maybe some people are wired to be happy without striving for any personal growth or success, but for most people, I think it's healthy to be challenging yourself and pushing yourself. As long as it feels rewarding and it doesn't compromise your wellbeing. I say that because I do think there's a lot of people who never really see any success in their lives because they just talk themselves out of it before they even try. But that's not Chris. He says that he's content and he's stable now, and he made this joke about how he's not ambitious, which, by the way, is nonsense. The guy has a business that does something like $1 million a year in profit, with just a couple employees. That's amazing. That is very ambitious. But the reason he is where he is in life is because he was super ambitious early on, and he put in a ton of work to get to where he is now. And this allows him to focus on being the dad that he wants to be.

[00:34:42] Chris Bakke: Our first was born when I was 32, so was had left. Indeed, like Post-acquisition first company was just starting my second company and it was just really nice. Like I think that there is a huge divide in my friend group between people that are still like, especially in the Bay area, that are just like grinding to stay head above water, like a lot of people in our friend group will make three, 4 or $500,000 a year combined income. Both parents are working, but they have 2 or 3 kids. And it's like our son's preschool is $1,000 a month. Each additional kids preschool is going to be $1,000 a month. Diapers aren't that expensive, but it adds up and you need a bigger house when you have a bunch of kids. And so I think having a nice base of many millions of dollars where you don't have to feel like every little decision you're making is killing you financially. I think that that would be really hard as a parent, and that's for sure the way that 99% of parents are living. And so it's really nice having having money and feeling established when you have a kid, I think.

[00:35:46] Sam Parr: Do you intend to leave your kids any money, or do you intend to help them out as they grow? Or if it's a spectrum of like making them suffer and giving them nothing or giving them everything? Where do you fall on the spectrum?

[00:35:59] Chris Bakke: It's a tough one. I think for sure. Helping my parents were never, you know, millionaires or multi-millionaires when when I was growing up. And but they helped me like, they were like, wherever you want to go to go to college? Like, if we can. Whatever we can do to help. We've set aside money since you were little to, you know, help you with that. Your grandparents have to. So that was, like, very helpful. It meant between, like a college scholarship that I got and their money. I didn't have any student loans coming out of college, which was a total game changer. You know, back to the money conversation. Like I wasn't having to make my first career decisions based on like, where am I going to maximize the amount of money so I can quickly pay off these student loans. So I think stuff like that can totally be a game changer for kids. It's a mix of de-risking their life, but also asking them to be ambitious if they like, really want to live a great life.

[00:36:49] Sam Parr: Having kids or or getting liquidity. What changed your life more?

[00:36:54] Chris Bakke: Oh, having kids for sure, without a doubt.

[00:36:57] Sam Parr: Why is that?

[00:36:58] Chris Bakke: Having a bunch of liquidity meant that we were able to go from a one bedroom apartment in San Francisco to, like, a five bedroom house in the East Bay and live the nice suburban life. But like outside of that, things day to day didn't actually change. Like, we moved, we lived in like a bigger place. Again, we weren't like jet setting. It's not like we were going to like Michelin star restaurants every night. It just like, I don't know, like you, you settle into your liquidity, especially maybe at that level of like having, you know, 5 or $10 million, like pretty quickly having kids is like it completely rewires your brain. It rewires, I think everything about where you live, for sure, like, where do I want them to grow up? Do I want them? Like living in a big city would be cool, but like, there's a lot of crime in some of these cities. Like, do we want to expose them to that? But we also don't want them to be too sheltered. Like, I think everything in my brain got rewired. You're spending tons and tons of time with them. Hopefully. So it just it means that you have to cut like friendships drop off for a couple years. I think especially like in the first couple years of, of life, like you're more everybody always says like when I tell people I have three kids under the age of three, they're like, oh, dude, you're in the trenches. I'm like, it sometimes feels that way for sure, but it also feels the.

[00:38:07] Sam Parr: Trenches is dope.

[00:38:09] Chris Bakke: Yeah, the trenches is awesome. Like, I don't know, it's fine. Yeah. Having kids though, because I mean it. Your whole schedule, your whole mind. You think what you think about what you care about. Your ambition all changes. I don't think it changes with liquidity.

[00:38:21] Sam Parr: By the way. I'll take the opposite of that. I think kids made me happy. Dude, make them money. Made me pretty happy. I don't know.

[00:38:29] Chris Bakke: Yeah.

[00:38:29] Sam Parr: The money thing changed my life more than the kid thing. I think I've been blessed that my kid is very well behaved and that she sleeps through the night and all that. And I had a dog forever. And I had, like, an elderly dog. And like, having an elderly dog is like 10% of having a child because you got to, like, carry it everywhere.

[00:38:49] Chris Bakke: And yeah.

[00:38:50] Sam Parr: You got to like, oh, we got to get it home because like, I gotta handle this or that with him because he can't go to the bathroom by himself. Whatever. But having liquidity definitely changed. Like, I wake up every morning and I'm like, I'm grateful, I guess. But I am that way with a child too. But yeah, it like was pretty game changing. And I and I don't like when people downplay it.

[00:39:08] Chris Bakke: They both are, for sure. It's hard to know. I mean, look like I would I would probably say to your point, like, yeah, if I was still living in a one bedroom apartment in San Francisco now with three kids and a wife, I'd be like, I would do anything to have some liquidity from this company that would change my life a lot more. But yeah, I think they both are big rewiring forces for sure.

[00:39:29] Speaker3: I swear you're the gold. I've been running on it like I woke up and won the top prize.

[00:39:36] Sam Parr: So the reason I enjoy talking to Chris is because I think this is kind of a weird thing to say. Or maybe a lot of people do feel this way and I shouldn't feel weird. But after I had a kid, I think having children was the biggest change of my life. And I think after I had a kid, I think there was some confusion because life was simpler before, meaning I was very ambitious. I wanted to make a lot of money, I wanted to try big things, and I wanted to work really hard. That's simple. Once I had a kid, I definitely want it to work, but I for sure wanted to spend more time with my child. I want my child to be proud of me. I want them to see me. I want to be present. And it made me feel weird. It made me feel like things have changed. It made me feel confused. Why do I not want to go out and kill people and get after it and go big and do all this shit, and instead just be like a soft dad and that kind of confused things. And I like talking to Chris because he's very confident in what he's saying, and he's saying he feels happy and that's okay that he's not like this big shot Elon guy. Although again, Chris is absolutely a big shot to have that much money that he has at his age. You're a big shot, you're a big deal. But it was cool to hear his perspective on life.

[00:40:47] Sam Parr: And I'm actually curious what you guys think. I'm on Twitter at the Sam Parr. I want you to tweet at me. Or if you're watching on YouTube, put it in the comments. I want to know how you guys feel. I want to know, did you actually have these, like, strange feelings after you had a kid? I had another friend who I think might come on the podcast who sold his business for $900 million, and he said after he had a kid, he wanted to make even more money because he wanted to show his kids how it's done. And also, he had less time. And so because of his less time issue, he was way more efficient with his time and more productive. And so he was driven to make more money. But right now that's not me. But maybe it will change when my kid becomes like 5 or 6 years old and they can actually see me work. And so I want to know your opinion. Again, I'm at the Sam Parr on Twitter. Let me know or comment on YouTube. And of course I have to do my plug. The reason I make this podcast is I have got this company called Hampton. It's Join hampton.com. So we do hundreds of events a year and we host all types of in real life core meetings, meaning people who have similar sizes and types of businesses as you do. Oftentimes because the world is remote, we don't get to hang out and be in real life with a lot of people who are like us, running companies, and so it's lonely.

[00:41:53] Sam Parr: And also it's super hard to get information like what we do on this podcast money wise. We uncover information which is about wealthy people talking transparently. You don't get that anywhere else. And with Hampton, you get all types of information that you can't get anywhere else. And you're able to meet people in real life. And if that interests you and you run a company, check it out. Hampton join hampton.com. Our average member does something like $25 dollars a year in revenue. And everyone has some type of like internet or technology company. So again, if that is you, if you're a CEO, a founder, anything like that, check it out. Join. And of course, if you want to make a podcast like this, you guys know where to go. You've listened to this podcast before. You know that I always plug Lower Street, Lower Street Moneywise. They are the production company that makes this podcast and they make it super easy to make podcasts like this. I just pay them a fair fee and they have me record. And then next thing you know, this is somehow on the internet and it sounds great and it works. And the story is wonderful, and I've got guests to talk to for the next week. And so if you want a simple thing like that, that gets you more customers, lower Street Moneywise always go.