Optimizing Life Post Exit

I recently joined a Post Exit Founders Group with over 1,200 members. They asked me to share lessons learned on my post exit experience. I shared my reflections on how to identify what’s next in your journey and find what truly gives you joy in life. I realize this is a 0.01% problem and that my lifestyle is unconventional and reflects my personal preferences. However, many of the approaches I cover from iterating in your personal life and outsourcing things you dislike are applicable to most.

Here is the timeline of what I covered:

  • 00:00 My Journey to Successful Tech Founder
  • 14:50 Unconventional Lifestyle and Work-Life Balance
  • 20:38 Finding Happiness Post-Exit: My Journey
  • 24:06 Investment Criteria and Team Importance
  • 28:21 Non-Traditional Family Setup and Work-Life Balance
  • 33:58 Outsourcing and Remote Assistants Strategy
  • 37:52 Remote Assistance and Mental Performance
  • 45:38 Entrepreneurship, Inequality, and the Future
  • 51:18 Balancing Work and Play: My Philosophy
  • 57:03 Founders and Leaders: Successes and Failures
  • 01:01:55 Decision-Making and Personal Experiences

You can find the presentation I share on unlocking productivity here. If you prefer to read the content, here is a transcript of my presentation:

Fabrice Grinda: What my posts, what my post exit strategy has been and became and also lessons learned along the way, and I’ll keep it brief enough that we can open up for Q and A. Brief: I’m French, though. I don’t sound French anymore, but basically, I fell in love with computers in 1984, the tender age of 10. It was love at first click.

And I knew we were meant to be together forever. I was one of the top students in France in high school. And when I went to talk at, I guess they tried to interview me for Le Nain. They asked me, what do you want to be when you grow up? I’m like, I want to be a tech founder, like my role models, Bill Gates and Steve Jobs.

And they were like, what? You would betray the ideals of the French socialist revolution. And I knew there and then that I did not belong in France. And that was under Mitterrand. And so, in 92 went to college, went to 17 at Princeton, finished top of my class, actually did not study computer science because I felt I knew it already, and graduated top of my class in 96.

And you wanted to be a tech founder but was I 21, was shy, was introverted, and so went to work for McKinsey and Company for a few years, which was kind of like Business school except they pay you. I thought I might miss the bubble doing that, but fortunately it didn’t. And in 98, I went on to build my first big startup.

I was 23, which was an eBay type company for Europe. It was called Auckland. I raised 63 million in venture money. I had 150 employees in the five countries, grew at a 10 million a month in sales. Had an amazing 300-million-dollar cash offer prior to raising all the money from eBay. But fortunately, or unfortunately convinced my VCs to take it instead We sold for a billion which sounds like more but for stock to a company whose stock promptly fell 99.98 mark a cap from 10 billion to 30 million during my lockup period. So, sadly grabbed Victory or defeat from the jaws of victory that went from zero to hero and cover of every magazine back to zero all over again, which led to a brief period of soul searching in 2001 about what I should do next, but I realized, you know, I’d like building something out of nothing.

I didn’t do this to make money. I’d like. I think this is the way to actually solve the world’s problems and harness the deflationary power of technology to make the world a better place, which is both inclusionary and addresses inequality of opportunity. And then with more recent tech, we can address climate change and the mental and physical well-being crisis.

And so even though tech was not going to be this big thing. There’s not going to be a huge opportunity. This is where I belonged, and so I decided to remain a tech founder. So probably went on, came back to the U. S., came back to New York to build my second startup, with a constraint that it needed to be capital efficient because capital was no longer available.

VCs would not fund anything in 2001. And upgrading company called zingy. I didn’t particularly like the product of selling, but it was a means to an end. It was a ringtone. So the heck, you know, one or two or three or four or five and it was extraordinarily tough. I missed payroll 27 times. I invested every last penny I had.

I borrowed 100,000 on my credit cards. I’d lived. I slept in the office and shower in the office. I lived in New York, such on $2 a day for almost 18 months. But ultimately grabbed victory from the jaws of defeat. And we went from a million of revenues in 02 to 5 million in 03 when we became profitable, you know, building companies the old-fashioned way without funding being some profits to 50 in on 04 and hundred in 05.

Sold that company this time for cash to a publicly traded competitor too early. But as we’ve all learned too early is better than too late. For 80 million of cash in the summer, in June of 04. And at about 50 percent of the company, I, I stayed on CEO for 18 months, and it’s interesting because at that point in time, it didn’t change anything in my life.

I think I bought a TV, an Xbox, and a tennis racket, but I still lived in my, like, tiny studio apartment because the same way that I’d been working 100 hours a week before, once we became profitable and it sort of became our rocket ship, you know, we did one to 200 in revenues in four years. We kept hiring changing offices.

I was working day and night ultimately left because I didn’t like the people I sold it to even though I liked being publicly traded and being, you know having to learn section four Well, I didn’t like it. I thought it was an ambition I had but then realized that being a publicly traded CEO didn’t mean the same thing in 2004 or 5 that it did 20 years earlier when you didn’t deal with section 404 and SOX compliance.

And many of you public CEOs out there have come to realize that the regulatory environment has changed. And so, I decided to go back to my first true love, which of course was marketplaces, which was the reason I built the eBay type company to begin with. I like creating, I like acid light businesses that were winner takes most.

That are highly deflationary and that bring liquidity and transparency in opaque fragmented markets. Craigslist at a ready come of age. And was large and larger growing. So, I went to try to convince Craig to either let me run Craigslist for free and they create a better user experience because I felt that they were letting down their community, even though they’re providing an amazing free public service.

And he said no. Then I tried to buy him for a couple billion. He also said no. So, I wanted to build my own. Ended up building a company called OLX, which today is the largest classified site in the world. It’s 11, 000 employees in 30 countries. None of you have heard of it because even though we are part of the fabric of society and we have 350 million unique visitors a month, we were only big in emerging markets where the leading player in Brazil and all Latin America.

And Russia, Ukraine, Poland, Romania, and all the Eastern Europe. Well, the Russian asset was kind of stolen recently by Uncle Vladimir, but that’s another story. India, Pakistan, Indonesia, Philippines, all the Southeast Asia, and UAE and all the Middle East. Company is ginormous. Today’s worth, I don’t know, at least 10 billion.

Would have been worth probably double that before the Russian asset was stolen. And, and, and doing really well. I sold it. So, I created that in 2006. I sold it. In a complex transaction over three years in 2010-2013 because I needed about a billion dollars to get it where it was because we had a publicly traded competitor in Europe.

That was coming after us and spending were investing hundreds of millions in TV and emerging markets, which are American VCs back in the day would not have funded in 2015. I think a tiger or a softbank might have funded me to do this, but in 2010, it was hard to go and convince my American VCs for founders funds and general catalyst ambassador to give me hundreds of millions to go spend on TV and Zimbabwe and Pakistan.

Ultimately sold the company. I say for three years after I they started investing in the company. I won the war with my biggest competitor. We merged 51 percent for us, 49 percent for them, and I left in 2013. Now, at that point in time, I was already an investor in 173 companies. Now, while I was CEO of a company of my first company in 98, I started being by virtue of being a consumer facing Internet CEO.

A lot of the founders were approaching me asking if I should, if I could invest in their companies. And I thought long and hard, should I do this? And ultimately decided, you know Even though it is somewhat distracting. If I can articulate lessons learned to others, it makes me a better founder. And number two, I’m running a multi category horizontal site.

If I can actually meet all the verticals and understand, keep my fingers on the pulse of the market, it makes me a better founder. So as long as investing in other startups doesn’t take more than one hour per startup, then it’s okay. And so, I decided to only invest in marketplaces and not work in back businesses.

And I created four selection criteria by which I evaluated whether I would invest or not in one hour meeting in startups and kind of that took a life of its own, especially after 2004 when I my other exit. So, by 2013 at 173 investors at 37 exits was doing very well. And with a friend of mine really created just a family office where we were going to invest in startups.

We were going to build startups. And in fact, since then, we’ve built in a studio model over 10 startups, one of which I ran a CEO founder. Grid became another unicorn sold that never expecting to be a VC. And in 2015, one of the people that I backed my competitor and when I was at OLX said, hey, we now own these different marketplace assets. We’d like to have exposure what’s going on and if visibility and what’s going on in the U. S. to bring to emerging markets and to perhaps defend against disruption, can we be an investor in you? And they actually offered to invest in my in my family office. I said no because I, A, I thought would be, if I kept raising, it would be infinitely dilutive.

So, I didn’t want them to invest in the operating company or the GP, if you want. So I said, it said, let’s create a GPLP structure. Let’s create a fund that you can be a, that you can invest in the funds. Created a first fund of 50 million, where they were the sole LP. Now, of course, not including all the capital I was putting in. In 2016 deployed that by the end of 2017, then they agreed to fund to in 2018; raised 175 million from 20 LPs.

And we’re finished pulling that mid 21. And then now we have a fund three, which is 290 million from 50 LPs. And LPs are either a combination of friends of mine that have been great tech founders, you know, the Reid Hoffman’s, the PayPal mafia, the Kevin Ryan’s of the world. You know, transfer wise founder, Wayfair founder, et cetera.

Number two, like family offices being disrupted by tech and three strategics like eBay and actually all the people that have bought my old startups like Naspers, Process, Adavinta, Shifstead or Axel Springer, Recruit, et cetera. Now, what’s interesting is I’m not a normal VC. I, this, I would describe what I do as angel investing at venture scale.

We write small checks. We don’t bleed. We don’t price. We don’t take board seats. We invest in every geography, in every industry, at every stage. And we decided two one-hour meetings using the exact same selection criteria that I defined 25 years ago, whether we best or not. So, every week we get about 300 inbound deals, and it’s all inbound based on our reputation and brand.

Third comes from VCs. A third comes from the founders. We back from the past. We’ve invested in 1100 startups. That’s about 2000 founders. They come back with the next company. They send us their friends, employees, and about a third comes in cold. We review cold inbound. Deals are randomly assigned to one of the 11 investment team members, and we decide if we take a call or not.

We take about 50 calls a week. The other all the other companies are like we have enough information decided that we don’t want to look at them right now. They’re out of scope, too early, too late, too expensive, whatever. Okay. We have an investment committee every Tuesday for the for the new deals after two hours.

And then we take a second call about five to 10 of them every week. Let’s say seven on average, of which I’m mostly taking. And on the second call, I will decide if we invest or not, basically. We do the same thing for portfolio companies. We, we have many things that are non-traditional. So, we have set sizes per stage.

We write 125K pre seed, 250K seed, 350K A, 550K B. Commitment checks are double. We don’t want to be a signal and we treat follow ons as though we were not existing investors knowing what we know now of the team of the company of the traction would we invest in this you ran at this valuation and very often the answer is no so we’ve only followed on in about 33 percent of the deals historically, and we often sell on the way up.

We sell our winners. It’s the anti BC strategy. But because we’re price sensitive, and we know where the median valuations are, and I’m happy to share what they are later. If you guys are interested, we you know, we come in a reasonable or nothing’s cheap, but fair valuations on if we feel something’s overvalued, which simply are the winners.

We sell 50 percent on the way up. Nothing’s magical, but 50 percent other than the fact that it’s a no regret philosophy. If the company goes to zero, we make five extra 10 X. We’re happy. And if it goes to infinity, we saw 50% and we’re happy to let it ride. And in a few cases will sell 75 percent of refields.

Really outrageous. You know, 100 X a R or whatever. We still build companies. I’m currently building a personally I mean, It is part of the funds, but I mean, I’m allocating 40 percent of my time to it. A yield bearing stable coin to try to replace USDC and USDT backed by U. S. T. Bills. We don’t have a formal studio program anymore for a variety of reasons, but the returns of the studio were less compelling and less scalable.

The returns on the investing side where, to date, we’ve had 1100 investments, 300 exits. We’ve been compounding at 37 percent IRR for 25 years, and of course, more of the capital has been deployed in the last six years than prior to that. We’ve deployed 600 million to date, of which 170 million, 179 million is for my partners and me, mostly for me, over 150 million of personal capital.

Things I’ve been pretty, beyond what I do professionally in the post-it era. So, in 2013, I made a lot of iteration, so I realized that most people don’t bring as much iteration in their personal life as they do to their business life. And I came to realization, you know, every I saw my friends less often than I would like, and the quality of the relationship has changed because as you get older, your friends become busy.

And as results, instead of like remaking the world that we did in college, when you see them, it’s a biographical update in the last six weeks since I last saw you, this is what our kids have been up to my wife, my husband, whatever my job, and but it’s not it’s okay, it’s not the reason we became friends.

And so I actually decided to go through a period of extreme iteration, wherein I gave all my non-financial possessions to charity in late 2012, and I went down to 50 items, everything I own. Fit in a carry on my backpack and my tennis bag. And I decided, okay, to go back from first principles, because, of course, if you have a place to go to a city in which you live, you just go there and you don’t ask yourself if I have infinite time and an opportunity to do whatever I want and meet whomever I want and be wherever I want, what is it that I really would like to be doing?

[Where is it I would like to be doing? And who is it I would like to be spending time with? I threw a lot of spaghetti in the wall, most of which failed, which is also true of startups in general. I started by going couch surfing on friends’ couches because I thought the idea was I could reconnect with them in a more meaningful way.

Now, that failed dramatically because, as Benjamin Franklin said house guests like Bish start smelling after three to four days. And the reason is if you’re embedding yourself in their life, but they’re not making room for it because they are busy with work and kids and whatever, then it doesn’t work.

And I’ve, as you can probably hear, Infinite energy. I go to bed very late. I don’t sleep very much. And so, my vision is like, we’re gonna, you know, we’re gonna like play tennis from like 8 p. m. to 10 p. m. We’re gonna remake the world. And, well, I try to sleep as much as I can in high quality sleep, but I am high energy and it wasn’t compatible with other people’s lives, especially since I was single and, you know, financially dependent and which is not the case of most people.

Iterated a lot to the model where I am today where because; And I was couchsurfing at friends couches. So not a real opportunity to meet a wives, but Where I ended up, today It is one where I feel that each city and someone made a comment about like leaving the snow or whatever Each city is a best period to live in.

You know, so I live in New York notionally, which means I’m in New York about four and a half months a year. I think New York is extraordinary in September and October, and it’s extraordinary like April 15 and June 15. But I don’t think it’s particularly compelling, even though I’m in New York right now in the summer or in the winter.

And so. I actually created a distributed life between three core locations where I home a place, and I rotate between them. I’m January, February, typically in Revelstoke, British Columbia, where I work from there during the day, but I’m heli skiing, backcountry skiing, et cetera, in the winter. March, I go back to Turks and Caicos, where I’m working during the day, but at night I’m like reading, writing, meditating, kite surfing, playing tennis, paddle, et cetera.

And then April. May, June, I’m in New York. June, late June to early July, I go to see my family and friends in Nice. Visit uncles, aunts, family, cousins, nephews. I mean, I have a ginormous multi hundred percent family. Go back to my birthday for a few weeks in Turks in August, then go to Revelstoke in, in August to mountain bike rock climb, et cetera, again, working during the day, but doing all these activities at night and the weekends.

Go to Burning Man every year, and then back to New York, September, October, and then back to Turks, November, December, and for New Year’s, usually go to Revelstoke. I add two weeks to a new exotic location every year. In 2023, for instance, the first two weeks of the year, I walked to the South Pole. I do a typically an off-grid category upgrade section every year where I completely disconnected. Usually alone, either doing, I know I crossed Costa Rica on bicycle from the Atlantic, the Pacific, but just my backpack, sleeping bag and tents and water filtration system and learned to start a fire.

And I’ve done a lot of these types of adventures and I do them regularly, often alone these days with a guide. And pass alone alone. But now with a guy because I’d rather not die, especially now that I’m a father to a two-year-old, very nontraditional life relationship and general setup, but works for me.

And I’m as happy as can be. Other thing. I know Jonathan Swanson from Thumbtack presented here, but I’ve structured my life to only do the things I love doing. And not do any of the things I don’t like doing. And so I have a virtual assistant in the Philippines which I pay 1500 a month who manages a big chunk of my online life, but more than you can imagine like if I’m going to play she’ll like I she knows I love tennis she’ll Fine, she’ll book free.

She’ll identify the best clubs, find partners my level, pre book the lesson, pre book lessons or partners to play with. If I’m in New York, she’ll organize, she’ll look at all the activities there might be for me to do. She knows I like to organize intellectual salons. So, for instance, I’m hosting a post exit founder dinner tonight with like, six sets. Well, eight people total. And I host these intellectual salons in New York. I’m going to like whatever magic shows off Broadway, you name it. And all this could be outsourced. In addition to having an estate manager that manages my offline life and I outsource things like creating helping create photo albums, videos.

But you name it, I’m happy to go in more detail on how, you know, I have four part time nannies that I’ve hired because French nannies are going to work more than 20 hours a week, but they, they cover 745 a.m. to 745 p.m. seven days a week, and they agree between themselves who works when and also who travels when and where.

And so, I’ve, I’ve created an entire system for basically making sure that I live as rich, passionate life as I can and not do anything of the things I don’t like. And there are a lot of things I don’t like in life. I guess from a work life balance perspective, probably worth mentioning, New York plays the role of intellectual, professional, social, artistic endeavors.

But I’ve come to realize that when you’re doing, you’re not being thoughtful, you’re not being reflective. And so actually, I like that alternation where I go from two months in New York, by the end of which I’m exhausted, because You know, it is 24/7, 7 days a week, basically to going to place like Turks, where even though I’m working during the day, the evenings are really meditating, reading, writing, being healthy, playing tennis, playing paddle, etc.

So would not have expected and where I am, neither from a life setup perspective, three different distributed locations where everything’s kind of replicated from an infrastructure perspective, would not have expected to become a BC. And again, I’m a non-traditional VC. Because I don’t lead enterprise, et cetera.

I don’t currently have institutional piece that that’s the objective for fund four, but I’m not changing my strategy. I don’t want to change. It is a reflection of my personal intellectual curiosity. I want to have the flexibility to continue to be building companies because I think it’s fun and interesting, et cetera.

I’ll pause here. I spoke at a million miles per hour, which is I am prone to but happy to yeah, answer any questions and keep the conversation dialogue going.

Barak Kaufman: That was amazing. Fabrice, for doing that. So firstly, just for everyone, feel free to post questions in the chat. I think we’ll prioritize everyone to raise their hand just like Sam just did.

I’ll come back to you in a second, Sam, but feel free to keep your hand raised and anybody else that wants to raise their hand in Zoom. Fabrice, just to kind of kick things off, kind of one question for me it sounds like you’ve kind of, like, tinkered and tried to perfect this model in the post exit life and you went through different iterations.

I think you used those words. If you were going to give advice. To a founder who recently went through an exit, what advice would you give them?

Fabrice Grinda: Well, obviously, the answer is personal, but take time to reflect on what it is you truly love to do, what is it you’d like to allocate your time to and what is going to make you happy? You know, for instance I’ve come, I came to realize that I’ve been overworking like probably many of us have, and, and I love working, but I didn’t value it in my, my friends and family as much as I would like to.

I didn’t, and they didn’t feel as valued. My grandmother, which had been the matriarch of the family, had used to host all of us at her place for Christmas, Christmas Eve, it was a tradition, like there’d be 20, 30 of us would come there, and we’d be organized by age, and she was really the rallying point of the family, and that had kind of gone away after her passing, and I decided, once I had the financial means to do that, to restart or rekindle the tradition, for instance, so for now, every year, Sometimes for my birthday, but definitely for Christmas or New Year’s, a big chunk of my family comes at my place in Turks and Caicos, and I literally, I’ll send a jet to pick them up in Nice and bring them over to Turks.

I’ll find tickets for everyone. I’ll rent eight different houses. This Christmas, for instance, or this New Year’s, for instance, there’s 50 of us, 50. I came for two weeks and we had a blast and it’s something that I it does. It takes a lot of work to make happen, but it’s something that I valued and prioritize.

Let me see if I can share my screen here just for a fun photo of the family. I can let’s go to Facebook for a second, not common moderation to do it. Not that Facebook is the best place, but I have that photo handy, so it makes it easier. Oh yeah, I did post it. Yeah. So, this is US 50 people for Christmas, for New Year.

And it goes from my son, who’s two and a half to my uncle back here who’s 87. And these are, are I saved? It’s the family I have and the family I choose. So, it’s it’s it’s a very, it’s a very big group and but it’s super loving and supportive and something that I valued. So, I’d go to as I said, I’d go to first principles.

I see a lot of questions. So maybe I’ll take I’ll take them 1 by one. Do you share the four criteria used to invest? So that’s a question for Michael Cassidy. The answer is I do. I will actually first put the link in with the actual criteria, but I will describe them as well briefly. So, wait a second.

How FJ Labs, so I blog, as you can tell, I just wrote my year in review blog posts which covers professional, personal predictions, et cetera. So, these are the four criteria, the four criteria. So, in a one hour call, I’m trying to evaluate number one. Do I like the team? Well, I’ll give you the four and I’ll go in detail.

Do I like the team? Number two, do I like the business? Number three, do I like the deal terms or number four? Is it in line with my thesis or vision of where the future of humanity is now? Number one, do I like the team? Every VC in the world will tell you I only invest in extraordinary people. The thing is it can’t be subjective.

It can’t be something you know if you see it. And so, for us, Or for me, I have an explicit sense of what that means for it to be an amazing founder. And I want the Venn diagram intersection of founders that are both extraordinarily eloquent and amazing salespeople because they’re going to raise better capital and hire better terms, they’re going to attract better people, they’re going to have more BD and more PR.

But that’s not enough, because if you only have that, maybe you don’t build a very profitable, sustainable company. Number two Do I want founders who know how to execute? And the way I tease out at one hour call if they can execute is the way they address the question number two. Question number two, which is, is this an attractive business?

So, it’s a combination of total addressable market size, but more importantly, unit economics. Now I’m mostly seed rather than pre-seed, but even pre-see. I want the founder to be able to articulate what they’re that they’ve done it. Lending page analysis that they understand the density keywords that they know what the CPCs look like, how much they can spend per month based on an estimated conversion rate.

What a cat looks like, and they better know what the average order value of the industry is and where the cost and margin structure looks like, and therefore get a sense of LTV to CAC. And if they’re alive while they be able to articulate what they are, and if they’re not good, and I want I like businesses where you recoup your fully loaded CAC on a CM2 basis in six months, and you 18 months, why it’s going to get there with skill.

And when founders cannot articulate that, it typically does not lead to amazing outcomes from the ability to execute. And so, I want both of these things to be true, and I care deeply. It’s not all the founder and only the founder. I think Warren Buffett once said when the reputation of an amazing founder means that of a terrible business, it’s typically the reputation of the business that wins.

And so, founders matter, but the business you’re in matters dramatically as well. Number three, deal terms. I know what the median is. The median these days for pre seed is about you’re raising one at four, five, pre, pre-seed seed you’re doing. If you’re a SaaS business, you’re doing 30 k at MRR or a marketplace, you’re one 50K and GMV and you’re raising three at 10 pre, and that’s or 12 free.

A’s these days, you’re doing 100k plus in MRR 500, 600, 700k in GMV, you’re raising 7 at 23 pre 30 posts, and the B’s, you’re doing 500k plus in MRR, or you’re raising, you’re doing two and a half million GMV, and you’re raising 15 at 50 pre. These valuations to many appear low, especially people based in Silicon Valley, or people that have been investing in the new, new hot trend of the day.

But that’s because the mean is higher than the median because they’re exceptional deals for second time founders that are raising these insane rounds. But what I’ve made money on half of my, so I’ve had 300 exits. I’ve actually made money in 50 percent of them 150 of them because I came in at a low price.

And so even when the company got acquired, I came in at five or 10 15 or 20. And I did okay. If you come in at a high price, your price for perfection. And yes, there are some companies you’d rather be in than not, and you’re willing to pay up, but I’d be extraordinarily careful. To mix it up because I’ve only been answering questions in the chat, I’ll take Sam’s question, and then I’ll go back to the chat.

Barak Kaufman: Alright, cool. Thanks so much. So, it’s interesting to hear how you balance the nanny situation and multiple locations. And it sounds like you have young kids, so have you considered what to do with respect to school? Because this is something that I’m struggling with my wife and figuring out how to do multiple locations in school.

Fabrice Grinda: So, I have a life partner. So, the school and I put the valuation matrix in the chat for schooling. So, we put my so until now, it’s been easy because my Some was too. So, you came with me everywhere and there was no school. So that was the the perfect setup. We decided to put so my big chunk of my family only speaks French.

So, the nannies were only French speaking because, of course, we live in the U. S or New York and they’re going to have English by default. I put my son in a school called The Ecole. The Ecole is a new school created by one of the renaissance hedge fund founders and the philosophy is the rigor of the French system with the creativity of the American system where you have like public speaking and teamwork etc and you have both an English speaker and a French speaker in both class in each class plus a helper to deal with like everything else so it’s three people per class they have a two’s program my son is in the two’s program and so what I’m changing to my current schedule to make sure i see my son more Is I’m with them full time from April 15 to basically November 5 because we spend the summers together and I’m in New York then.

Instead of going away for two months at a time, now what I’m doing is I’m making, I’m making sure, so we spend all of our vacations together but he, he and his mother doesn’t travel with me and, and she’s a partner at Kirkland the law firm. She’s working on like IPOs and M& A and public work. So, I go. I make sure that I’m not away for more than two weeks. So, I’ll go two weeks with you to Turks alone, which I need anyway for reflection, etcetera. And I’ll come back to York to spend a week or two with them full time. And again, we don’t live together. So, we have a non-traditional relationship. We have a philosophy called living apart together, which probably it’s worth mentioning it for a second, because I find that if you spend too much time around your partner, you become roommates. As opposed to becoming really lovers and life partners, and you’re not present in every interact, iteration, interaction.

And, you know, because if we’re together, if we live together, you know, maybe I want to be playing video games for a couple hours, or I want to be working, or whatever, and I’m not present. And so instead, we live separately, though I see my son literally every day, multiple hours a day, phone off, or we’re just playing.

And I will put the link to the school in the chat, it’s called the Ecole. But if you’re not interested in and you know, I just said French speaking. It probably doesn’t make nearly as much sense for you, but it’s an amazing school and I’m putting it here. Okay, so we don’t live together, and we choose to go together.

So, we do family night, maybe. Two nights a week. We do date night just us without kids two nights a week, and we do date night at my place. We do family night at her place, but I will see my son every day, multiple hours a day with phone off, but I don’t sleep there. And it works very well for us. And so, when, in the month where I’m traveling, where he’s in school, so October November, sorry, November, December though not the holidays because we’re together then I’ll be in Turks, we’re Revelstoke, so maybe say January, February, but I’ll come back to New York for a week.

But we spend all of our vacations together. So again, non-traditional setup. It’s also a setup that my partner loves and that works for us. I focus on quality of time, not quantity of time. And I revised the right to change my mind about the setup and in the future, but I’ve already changed it, right? I went from two-month, two-month, two months to making it to maybe three weeks, one week, three weeks, one week, et cetera, to make sure that I’m seeing my kids as often.

Well, kids plural, because I have a daughter coming February 15th. Not for everyone. Thank you. Not for everyone, but it works for me. And I have a dog as well, a white shepherd, a white German shepherd that travels with me everywhere. Actually, I’ll give you a sense of how it works by putting a, put a photo, a link to my urine review in here. Okay, let me go back to the questions.

I don’t know if anyone else has their hands raised. In the meantime, I’ll go back to this. How long did it take to donate everything? Rootprost, you’re thoughtful.

It took very little time, but, and I had to put zero thought into it, but when I went to my partner and I’m like, Hey, I’m going to do this for the next six, whatever, X period of time, I’m giving away everything away. And she was like you have like this 13,000 square foot house and bowl of stuff. Who are you donating to and how?

And she basically structured it for me. And so. It ended up being thoughtful, but not I was not very, but it took very little time because she really coordinated it. And that was back in 2012. And so, we, you know, from the books to the to that went to different schools or libraries to the furniture that went to either people.

We knew people that needed it to the clothes that we don’t. I mean, everything ended up being more thoughtful, but I have to admit, I took. I just made the executive decision, give everything away, and I didn’t deal with the details that my partner did. And she’s amazing. Da da dum. Left connected, yeah. Why remote assistant? Why not local? My remote assistant in the Philippines. I’ve so I’ve never talked to her. I’ve never met her. Because I my philosophy for hiring is I hired like multiple of the same on Upwork or elsewhere. And then I give them a partial task. I see how they do. And then I keep the best. And that’s I found someone in Bangladesh like a dollar an hour to help with my photo albums.

I’ve been someone in like Russia to help with my video editing, etc. In this case, it’s through a company called yourremoteassistant.com. I’ll put the link as well here. And you basically, so they send you one, they’re based on your specs. And if you’re not happy, you just change, get another one.

That’s why I never bothered to interview her. We’ve been working together at this point, at this point for a decade. It’s extraordinary because she’s like a PhD in creative writing. She’s way, way more skilled than any assistant I’ve ever had, including in person. She works exactly whatever hours I want to work.

So, when I change time zone, she changes time zone as well. She has access to everything from signatures to I mean, and I don’t know. I find that she’s been just more effective, harder working than anyone I’ve ever had in person. Not to mention it’s way cheaper. So, we at our firm, we have 10 of them.

And the amount of stuff you can outsource is greater than you think. You know, if you like, if you have an online Shopify, they can do customer care. They can do, they can do inventory management. I mean, you name it. In my case, she will help. She pretends to be me, stays on the phone with T Mobile, or gets to doctor’s appointments.

I mean, you name it. Everything is done, and it’s extraordinarily effective. And I actually like the working through WhatsApp with her. I find it. I don’t know. We have an office manager, and I used to have an in-person assistant. I’ve had many of them, including very well paid, super high end, and maybe that didn’t work nearly as well.

I think for that type of role, I have an estate manager, and my estate manager, actually, maybe I’ll share my screen for a second. This is something I’m presenting tomorrow. Take it to one second, predictively. Minimize this.

Life hacks. I mean, probably this is not obvious, but I don’t read any news whatsoever because, like, following the day by day of anything is actually not that relevant. So. Yes, it’s terrible and tragic what’s happening in Gaza or Ukraine, but you know it’s happening and then taking a step back once every six months understanding why, how, etc. is relevant, but like the day by day is completely irrelevant, you know, in COVID in the early days, it was all about like who violated the mandate, like there’s no real information, right? Like what I want to know in COVID is, you know, and it hasn’t come out yet is what would be the correct policy decisions to minimize health outcomes and economic and negative impacts and probably the answer is different in the early days.

We have no vaccine that later when you do have a vaccine, but like that’s an analysis. That’s interesting. The day-to-day use. It’s all sensationalist BS. So, I don’t read news. I don’t read newspapers. I don’t read online news. I do nothing. I follow tech news, but like against time as a day. Twitter and all that stuff.

It’s all negative all the time. They’re capturing your attention and focusing on outrage. I completely avoid it. I’m sort of saying so. You’re a remote assistant. The other very good one is Athena. That’s the one, that’s the company created by Jonathan Swanson from Thumbtack. You probably presented it here.

But she manages all of my Agenda pending meetings. Confirm meetings. This is what I get every day. Then this is my agenda. If I know what it’s about, there’s no conversation. There’s no detail. But if I don’t know what it’s about, she will put the detail of the context of why I’m having the conversation.

That’s for the next day. This is a typical day for me, by the way. So, yeah, and it goes to like, and it’ll include all the personal stuff. So, yes, I’m giving a speech or whatever here, but then. Paddle, which is a form of tennis. If you want 9 pm. to 11. Everything is in there. If I’m going to do a meditation, go to the gym.

Everything is in my agenda every day, but she will manage invites for dinner. So, for instance, the dinner I’m doing tonight, she’ll book doctor’s appointment. She’ll wait in line at my behalf. She’ll book meditations, gym. She organizes tennis. She helps create posts. So, she knows how to code as well. I will write the blog post, but she will write, she will post it and she will publish it and send the newsletter and she manage the Substack.

So, I do it in my WordPress, which I coded myself because I like doing that and I like writing, but she will manage the Substack on her own. She’ll buy stuff for me, including on Amazon, because it’s easier to just tell her. She’ll sign everything, do the KYC, do government research, look for shows for me to attend, manage my, she created a design for my birthday invite.

She manages the invite lists. She manages all travel things and then this I iterate for album creation, you know, like slide 27 do this. This this photo makes me look back, but a different photo, whatever. And then you have the full album that I print and give to my parents. I do the same with someone else.

By the way, I’ve been on UpWork for videos, and I create a video every year. And for every 1 of my major trips, and then for offline. I have an estate manager, so he’s my main estate manager. He’s a chef otherwise, but he drives, he cleans, car maintenance. If tonight for the dinner, he’s normally cooking, but he’s organizing the whatever, like waiters.

If it’s a big party, he will bring, he will bring chef, like everything offline, and he manages the other property managers. For each of my properties, I have a estate manager slash property manager, and that is also the chef, and they manage the staff and all the licensing, and I do sublets, whereas this house here generates 4 million in revenues, when I am not there. And I am there four months a year, and they manage that, but they don’t manage the reservations. They just manage the customer experience. I’ve outsourced to an offline the reservation manager. I created the site myself, and I moved all the traffic from Airbnb to direct reservations because that’s what I’d like to do.

But I have someone managing all the reservations for my dog. I have a full-time dog trainer and who actually travels with me. Gets all the documents. Gets the vaccines. Now that’s not forever. My dog is six months old, but for the first two years.

And then for the nannies. So, I find them on care.com and also in a French. I make sure they speak French. They have a website to group routine themselves. I only take one for travel. They all have a shared calendar app. And I need them to be able to speak French verbally, can travel, can drive, because they need to be able to drive the kid. And everything’s organized here.

Then there’s a nanny handbook that I created where everyone is following it. And so, there’s like instructions of what needs to be done, etc. So that model works.

Barak Kaufman: You’ve just wowed this entire group. I think everybody’s gone just throughout wherever they were at the level of optimization.

So, thank you for sharing that. And there are quite a few requests if you’re comfortable sharing the presentation after.

Fabrice Grinda: Yeah, I will. I think I’ve put the link. I put the link to the presentation and Dropbox, I think somewhere. But it’s gonna be on my blog. I’m also going through this in detail tomorrow on my podcast at noon, but it’ll be on my blog shortly.

How do you manage all these companies and positions? Oh, I have a tool called EDA, but also more importantly, I have a big back office. So, the tool we use, let me put it here. It’s EDA.CA. Let’s see. Yeah, there, but it’s pretty cheap. It allows us to manage. Not everyone needs it, but also, we’re 34 in the firm. Of which, I mean, obviously 10 virtual assistants, but like 13 or like back office, COO, CFO, legal, all that stuff. And I don’t deal with any of that. Like, I don’t, life is too short to read legal documents.

Life is too short to spend time doing admin work. So that’s why I have a team around me to do all that shit that I hate. Someone wrote. Life is too short to deal with assholes. Completely agree. I do not tolerate jerks. If you’re a brilliant founder, but you’re an asshole, I will not back you, I will not fund you.

I will not invest with you. I will not hire you if you’re an amazing employee. Life is too short. You only work with people that you love working with.

Let me go back to higher on the let’s see if I miss anything. What’s your most impactful mental performance practice? I do meditate. I meditate I have a 20, well,10-to-30-minute meditation practice every day. It is I will write a blog post on how it is.

I do four or five different things, but they’re very quick and efficient, but I’m very good at being present. I have aphantasia. I cannot visualize and so whatever I’m doing, I’m doing that and nothing else. I also have no notifications on anything at ever my I don’t get email notifications, WhatsApp notifications. My phone never rings, never vibrates. Even a vibration takes you away from the present of what you’re doing. It’s like, Oh, maybe there’s something I should be looking at. You don’t want to have FOMO. Whatever you’re doing is that you’ve chosen to be doing the best and most important thing you should be doing right now, and so I have no notifications whatsoever, and I’m very good at, like, going from context to context in the present. Humans cannot multitask.

You monotask. You want to monotask effectively. So, I will book time for emails. I will book time for whatever. And I will be present in that interaction, but I will not, but you don’t want to be doing many things simultaneously. Meditation, I like guided meditations not with, and I follow, I don’t have an app. I have a few meditations I do, a few breathwork practices. I read a lot, but I read for fun. I don’t read to be more productive. I read mostly sci-fi but I read biographies. I read every 50-100 books a year. But I read for fun. I read one hour every day before bed, which is why I ended up that school. I think we discussed how we’re going to change when school changes.

How do you plan to school the child? Yeah, probably worth mentioning. I’m a laissez faire parent. It’s all about I want to encourage positive risk taking. I’m not a helicopter parent. I will. I wanted them to learn to fail and learn to fail in a positive way.

And you need to fail repeatedly to succeed. And I will encourage and reward work and effort over outcome. And I’ve already worked with that pretty effectively. And yeah, and the anti-helicopter parent. But I provide love and presence to the fact that my partner and I love each other. I mean, we’ve been together for 11 years, and we’re like life partners.

Even though it’s a non-traditional relationship, we have an open relationship, which is very non-traditional. And as I mentioned earlier, we don’t live together. It’s not for everyone, but it works for us.

Will you start more companies? If I’m inspired to do it. So, the problem for me, sorry, company at this point is the opportunity cost of my time is infinitely high, and I find that the amount of leverage I have by working with founders and helping them. And helping that many founders where my impact is actually meaningful, both either strategic advice and or helping them fundraise, which is my superpower because I’m not leading. I share a deal with all the top pieces of the world is massive. And as a result of that, it’s very hard for me to justify being founder CEO versus doing this.

But I like being founder CEO. So, I’ve created this hybrid model where I’m executive chairman, but not CEOs of companies that I like. Now, why do I do this? Right? I could have retired. 20 years ago. Actually, literally exactly 20 years ago. I was 29 when I got my first ginormous exit. It’s purpose driven.

Oh, wait, I forgot to mention number four of the selection criteria got distracted. Number four was like; does it meet my thesis where the world is heading? And I have a very clear perspective on the future of work, the future of mobility, the future of food, the future of every category you can think of. And ultimately, it’s purpose driven.

Are we solving a big problem? And there are three problems that I care about. Inequality of opportunity. Which I’m mostly addressing through marketplaces, because obviously they’re deflationary by virtue being deflationary. They’re inclusionary. Number 2 climate change, and I’m so optimistic that we’re going to solve it.

I mean, I’m seeing so many improvements, especially in solar and batteries and many other things, right? Like, and this is 100 different subsectors that I’m beyond optimistic and happy to double click on that at some point. And number three as I said, the mental and physical well-being crisis.

So why do I do these things? I think the political system is broken and is structurally incapable, but it’s broken, by the way, by design. I think it’s a feature. It’s not a bug. I think it’s the way the founding fathers intended it to be and people who think that the politics are so partisan, et cetera, it’s not worse than the past.

I mean, we had a full-blown civil war, we had, like, race riots, we had, like you know. The desegregation movement, the anti-war movement in the 70s, all these were actually just as acrimonious as what we have now, just we have recency bias and we think now is worse, but actually life is amazing right now better than it’s ever been, even though our politics are broken, but they were always broken and I suspect they will continue to be broken, and so because the political system is, is incapable of addressing these systems and these issues, it’s up to us, doers, founders, investors to go and solve the world’s problems. And so, but I’m so optimistic. I mean, we are going to rise to the challenge of the 21st century and we are going to create a better world of tomorrow for our children and for ourselves, a world of equality of opportunity and a plenty.

What is your relationship with money? it’s a means to an end. I don’t chase more of it actually. It doesn’t make any difference in my life. I’d more money is irrelevant, but I, so look, I do a lot of non for profit, right? I donate a lot of money. I fund the education of 10,000 kids K through 12 in Dominican Republic. But when I think of the impact I have, like the last company I built as 350 million unique visitors a month, we have 50 million people would make a living off the site.

The impact of that for profit entity on the world is dramatic. I mean, we are part of the fabric of society in Pakistan, right? Like these are, and this is true for all the investments I make. I don’t invest because I think they’re, I do think they’re going to make money. And I like the fact that because they’re profitable, they’re scalable and sustainable, but they actually are all making a positive difference to the world.

So, the objective is not to make more money. As I said, I could have retired 20 years ago. The objective is to solve the world’s problems. And I use the vector for profit technology enterprises to do it because their acid light scalable and can touch billions. Normal companies cannot touch billions of people that easily.

Any thesis on how to bring back knowledge, truth and facts to the masses? Well, truth, I don’t know but knowledge for sure right like we are now in an extraordinary period of democratization of information, right? If you want to have access, if you want a class by the World Nobel Prize winner, it’s on Coursera and it’s free. If you’re a K through 12 student, you wanna improve in math, you can use Khanmigo, which is the AI by Khan Academy. It’s amazing! So, if you’re motivated self-learning, it is easier to learn anything that it’s ever been. YouTube videos on every topic, extraordinary. And if you wanna start a startup. When I started back in the 1990s, I needed like Oracle databases and Microsoft web servers and millions to just turn the lights on.

I needed to build my own data center. Now you have no code, low code ai, like to, I could build you anything for sub 25K, probably. It’s amazing. It’s, it’s leading to a massive democratization of startup creation and entrepreneurship. That is beautiful.

And so yeah, any advice for a founder starting a year off. I should have taken a year off. The problem is it doesn’t suit my personality particularly well, I’ve always been doing things. So I went from thing to thing to thing, but yeah, beat, think through the things you love doing and go pursue them. Like look, I work hard, but I play hard or like I’m kitesurfing and I’m a fantastic kitesurfer, heli-skier.

I’m still a competitive tennis player. I’m still like college level tennis player. I’m 49. I beat like beat up on the 25-year-olds. You know, I exercise. When I’m in Turks, for instance, I was averaging three and a half hours of sports a day, every day to stay as fit as I can be. And yeah, just do fun, do crazy things. You always want to do like go to. I go to burning. I think psychedelics once in a while. You know, I drop acid. It’s amazing. Go do a deep go take Ayahuasca and do a deep journey. I mean, like, I don’t know, like, there’s so much to do and to be done and to live. It’s a privilege to be alive and it’s a privilege to be alive in this in this time period.

It’s a privilege to be post exit. So, money is a tool for freedom. It’s not something to pursue more of, but to actually enjoy and use it to make the world a better place.

Barak Kaufman: I just want to say someone was messaging me directly on the side and said, I want to ask him if he takes psychedelics, but I don’t know if it’s appropriate.

And then almost like on cue, he answered the question directly. So, thank you for that.

Fabrice Grinda: I am an open book. Nothing is secret. And everything’s transparent. Yeah. So, at psychedelics, I’ve probably taken everyone in the world from 5 MeO DMT to Peyote to 2C B to Acid to Psilocybin and whatever to Ayahuasca.

I take them rarely. I take them intentionally. So, it’s set, setting, intention. Crescents. I don’t microdose. I find microdose, you open yourself up to whatever, and then you’re going to work, and you have a stressful day. I think that’s idiotic. I like to macrodose, like, real, and either for fun, like, you know, let’s say, one, one and a half grams of mushrooms if I’m burning, man, or, like, if I were to do a real deep meditative journey, like, I did a nine gram psilocybin journey with music that was just, like, basically, you know, beautiful meditation for, like, seven hours.

A very introverted that’s alone. You don’t do I don’t think both are interesting. I did a couple times a year. I wouldn’t recommend a huge amount of time because it takes time. It’s distracting whatever but I think it’s worth doing on a you know what a couple times a year basis. So, at burning man, I’ll do acid for sure acid is like the one thing to do at Burning Man.

I know we’re probably overtime.

Barak Kaufman: I think as long as you’re willing to, yeah, it’s your call. It’s your call, your calendar. I think everybody’s enjoying it.

Fabrice Grinda: I can give a few more minutes.

Barak Kaufman: All right, let’s do it.

Fabrice Grinda: What do I think about AI and the future of AI? So, here’s so here’s what’s interesting. I think AI in 23 went to, we were at like the top of the hype cycle. Where clearly there is a transformation in the quality of AI with GPD 3. 5 and obviously not before and Gemini and Bard, etc. And I do think it will ultimately transform society in a more meaningful way that we can imagine today. But I also think it’s going to take a lot longer than people think it’s going to take.

And so that’s why I think we’re at the top of the hype cycle. And there’s going to be the period of delusion in the next five years. Because before. You know, when do we think governments who really integrate AI for improving its operating capacity or even large enterprise, right? Like if you’re a health medical claims processor, the hallucination problem is real.

And like, you don’t want to have like, you don’t want to be liable for, for having bad results. And so, while I suspect in 20 years, it’ll be so transformative. We want to be able to recognize a lot of things, the way we work and a lot of things, humanity, and the next five years, I think it’s going to be the period of like disappointment.

So, what I’ve been, and because AI overvalued as an investment category in businesses with no business model, no modes and no differentiation, I shied away from investing in AI other than a few specific vertical applications with proprietary data and in reasonable valuations, but they’re very far and few between, but everything we’re doing.

These is a is a I everyone’s using a I write like every company is using it for customer care and to be better and programming. I use it every day, right? Like what? I am not a great coder anymore. So, when I’m coding my blog and I forget some functions that just ask a GPT. Hey, what do you need us? What’s the correct code? Don’t ask to code entire thing that it sucks at that. But like specific functions very easy.

I have your investments done over time when you compare first time founders the second time. Yeah. Same average IRR, second time founders who, well I can actually wait, so second time founders fall in two buckets.

Second time founders have been very successful the first time, often become more purposeful and mission-driven of the second time and it leads to both better outcomes and worse outcomes, meaning more companies fail because they’re taking more risks and when they succeed, they succeed bigger by their blended IRs is the same.

Second time founders who failed the first time on average have done better than both, than just general founders and the second time founders who’ve been successful the first time because they are hungry and have a point to prove it if they’ve learned the lesson why they failed.

So, if they learn that, okay, oh, I spent too much money. I raised too much money at too high of a price, whatever, whatever it was, they need to learn, or they didn’t focus enough product market fit or uni economics, then it’s fine.

Barak Kaufman: Who’s the most impressive founder that you’ve ever backed.

Fabrice Grinda: I’m not going to do the most impressive founder, but there was a few very impressive founder and founders and some, some have failed, some haven’t failed. So, for instance, Alex Gardner, who built a zoom pizza, which failed completely, he is so eloquent and such an amazing salesperson and very proud of Ryan from Flexport is extraordinary. He’s a machine and visionary is amazing.

So, there are many amazing people out there. I don’t think there’s one that’s like, oh, you know, but like people Yeah, [00:55:00] there’s like let’s say oh, yeah Brett Addock. He’s extraordinary. So, Brett built Vettery, which was a labor marketplace, which we sold for, like, 100 million at echo. Then he went on to build Archer, which is an electric vertical takeoff company, which is which took public and now he’s building Figure.

Figure is made creating these humanoid robots who replace humans in warehouses. And the problems he’s solving to do that are so extraordinary. I guess I could put an Elon in the category as an early investor in let me put the figure link in here.

Barak Kaufman: I don’t remember if he’s in the community or not, but his it was twice shared as like SPDs to invest in at least a dozen founders from the group invested.

There was a recording of like his pitch for it. I have sent that recording that he did for like fundraising to dozen right from Attic exited Repeat founders. But yeah, like he’s just it was the best pitch I’ve ever seen in my entire life. He’s just yeah.

Fabrice Grinda: So, I think Brett is up there. Good. Amazing. Better. Obviously, I backed the Elon back in the day. I invested in 2007 and space X. Still an investor. I didn’t sell any of my shares. I’m not selling any of my shares. Yeah.

Who do you look up to and why? I guess historical role models, Octavian, or Augustus, who basically single handedly created the Roman Empire and brought an end to the civil war in, in, in, in Rome and created the basis for 500 years of Pax Romana and a significantly improved livelihood for humanity writ large for 500 years. I mean, at least the first two, 300 of that.

Alexander Hamilton, and not even American, but ultimately you know, reap. Trying to convince it forced the US repay his, that which created the treasury and li put the US on a path to becoming the world dominant superpower that it’s today would, would’ve been funnily different if he had lost these arguments back in the day.

So, you know, and it depends. And then it’s like just geniuses in different forms, like Da Vinci, even though he’s, we know so much less of him that, you know, none of the biographies are super compelling. But yeah, I obviously am a fan of Walter Isaacson and Rod Trudeau biographies and the people that they cover.

Barak Kaufman: What about anybody current, currently alive?

Fabrice Grinda: You know, I think someone who gets, doesn’t get enough credit. Well, two people. Well, Deng Xiaoping, he passed not that long ago, but Deng Xiaoping, who basically transformed China from a communist say to a thriving and enriched a billion people in the making, right?

Like decreased extreme property significantly by transforming China into capitalist country. Now, sadly, his legacy is being undone by Xi Jinping. So, if I if someone like Deng Xiaoping was in power in China today, I think China would actually be on track to become the wealthiest country in the world, but also I think would be an ally of the US.

Sadly, we have a counter, we have a Mao descendants in Xi Jinping who cares more about nationalistic power and his own personal power than he does about the well-being of his people. And that is a lot of it. So, I think China is no longer going to be the dominant superpower of the 21st century, given the choices they’re making right now.

It is sadly and. We have a cold war to not only brewing, but we’re actually active right now. So, thanks shopping would have been that in the recent decades. Bill Gates doesn’t give enough credit either. I think both for the role he played in the democratization technology. You know, a PC in every home, which has been massively deflationary and inclusionary as well, and actually the role he’s playing right now, it is not for profit initiatives.

What’s the best life decision you’ve made? What are the examples of wrong decisions? I’ll start there. I try. I wanted to build an off-grid community. Where I could where it could let founders come and build, you know, with no real business model artists come and create and virtual leaders come and lead and maybe do it.

And if it got too busy, do it maybe through applications, you know, where I see sell. And I bought a couple hundred acres of land in Belize, and well, first I got, I bought hundreds of thousands of acres in Belize, several percentage points of the country. Then we realized that in a, but in a republic, they can just take it away. What do you think you own? You don’t actually own, and they can take it away from you. So, then I’m like, Oh, I’m going to this much safer, more developed country, Dominican Republic. But I didn’t go in Punta Cana, Casa de Campo, I went in Cabarette, which because I like the kite. And I bought a couple hundred acres of land and turns out that it was still too banana republicy.

I did that in 2013 to 2019, but Everyone from the mayor to the minister of environment, tourism, they all wanted bribes, which I know is not willing to bribe them because I told them my time. I don’t want to be a real estate developer. I want to be using my time to the betterment of humanity through harnessing the deflationary power of tech.

And I’m not going to play the political game. Either you realize what I’m doing is amazing for you and your country and you’d let me do it legally, or I’m not playing. And I guess they decided not to let me play. And so even though I had 100 million development that I wanted to do in the Dominican Republic where I and I bought this one-mile beach friend hundreds of acres of land.

I never got to get it off the ground because of I never got all the licensing because I didn’t want to bribe anyone, and it ultimately became starting to become dangerous. I mean, normally do all my guests catch the catch and yeah, dengue, et cetera. Attempted rapes. Many burglaries. I got full on attacked by people with shotguns. There was a blowout shootout in my garden. Because I mean, it’s beautiful. It’s Ross authentic. It’s like the average GP there is like, you know, 2000 a year, but my family hated it. They felt it was dangerous. And I guess I, because I like going at these upgrade places where I’m like, you know, very poor countries and I don’t have any, I don’t have any displays of wealth on me.

I don’t appear where, you know, if you see me there, I’m like shorts and T, shorts and T shirt. I don’t have anything. I don’t have a watch. I don’t have. So, it never occurred to me, but, yeah. That was a mistake. It took six years and then I was like, okay, after we got it out, they murdered, they killed my dog.

I mean, it was a disaster. So eventually I left, I moved to Turks and Caicos, which is now my like family retreat. And I should have done that way, way faster. Should not have waited six years. Lesson learned, best decisions, you know, best decisions never came immediately. It’s always through iteration that I ended up finding what was right for me, but best decisions, you know, just be true and authentic to yourself and who you are and what you want and pursue that like and whenever I’ve done that, it’s always paid off.

I think I need to end it there. I’m meeting and very dear and I need to get there. But this is super fun.

Barak Kaufman: This is amazing.

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  • I subscribed your newsletters years ago and there are the only ones I like to click on and read or listen.
    Because even if we are living a different life I like how open minded you are, how you talk about your own experiences, and advices you give. To be honest in terms of personal wealth we are very far each other but there are some advices you I can personally apply. This kind of itw is a real lesson for me, because like you I always knew that I wanted to create my own company, not to be rich but to be free to do what I like only but I was not as brave as you 🙂
    So again thank you very much! Please keep writing and sharing videos like this one 🙂 !
    Wish you the best for 2024!

    • Thanks for the kind words. I do think many of my life lessons are applicable to many regardless of wealth. Obviously the conclusions I reach are personal, but the process is generally replicable.