Why Hustle Culture Is Broken - John Carbrey

John Carbrey is a Canadian entrepreneur and venture investor.

In 2005, he founded Intrafinity, which built powerful web content management tools used by universities, hospitals, and Fortune 500 companies across North America.

In 2008, he launched SharpSchool, a spinoff focused on communication and web platforms for K–12 school districts. It quickly scaled to serve nearly 10% of U.S. schools, delivering over a billion web and mobile views annually.

After selling both companies to West Corporation (now known as Intrado, an American telecommunications conglomerate) in 2015, John led the global tech team and helped grow West’s education division from $40M to $70M in ARR.

Today, he's building FutureSight, a venture studio that partners with SaaS founders to co-create the next wave of high-impact startups.

00:00 Intro & Teaser
00:55 Early Entrepreneurial Journey and Initial Ventures
04:42 Building and Scaling Companies in Canada
09:00 Transitioning from Founder to Executive
11:31 The Importance of Reflection In Your Career
13:35 Silicon Valley's Work Culture and Its Impact
17:56 The Psychological Tax of Hustling
24:11 Wanting Well: Redefining Success and Value
27:21 Understanding Mimetic Desire and Its Impact
33:41 Wounds and Their Influence on Our Desires
40:06 Wanting Well: Beyond Individual Desires
43:14 The Purpose of Business in Society
46:15 Finding Great Co-Founders
51:18 Example of An Excellent Founder
60:07 Advice For Fresh Graduate

Keith 00:55

John, thank you for coming on.

John 00:56

Delighted to be here with you.

Keith 00:58

You've exited companies in millions of dollars of value. I think I read on your website, even when I was doing my research, there's like Intrafinity, Civic Life, Telenova, Sharp School. I think in Singapore, most people are not familiar with these names because maybe it doesn't encroach on our geography. But could you help me understand back then when you first started your entrepreneurial journey, what were the problems you're looking to solve?

John 01:24

I started my first small ventures in high school. You could think of me as your prototypical computer nerd. I loved programming, writing software products—maybe not even products, just small software applications. I liked programming languages, so I was really kind of nerdy in that sense.

The first website I made was a programming website to teach people how to program C++, which is a low-level programming language. I didn't really start out saying I want to be an entrepreneur and make a lot of money. I was more delighted in the beauty of a well-architected system from a software perspective and the latest technology.

I was very lucky. I had a great initial co-op term—like an internship—in a company and started to get some experience, spent some time in Boston at an MIT startup at the end of high school. In my second year at university, I was in my dorm room coding some software when I got a phone call. Someone said, "Hey, I'd like to fly up to Toronto to meet you and your management team and all your software developers, and I'd like to use your software for our 10,000 employees."

I had the phone and didn't really know what to do with that. The prior time I'd sold software for maybe two thousand dollars, and they were going to pay two hundred and fifty thousand dollars for what they wanted. So I said, "Let me call you back." Eventually they came, and I decided to go ahead. Suddenly in second year of University of Toronto, I had to call my dad and say, "Dad, I know you had this idea for me finishing university, but what do you think we should do here?"

It's rare for a father to do this, but he said, "John, go for it. You can always go back to university." So I put university on hold and was thrust through that experience into an entrepreneurial journey.

Keith 03:45

When you started as a software company, back then you had this offer of maybe $250,000. You got the call, you want to start the company. What were the first five things you kind of thought you needed to do?

John 04:01

Well, it's an interesting story. I called a mentor of mine who was my high school computers teacher. He was a mentor who taught me software development. I said, "I don't know what to do with this." And he said, "Well, let me help you." It's a bit of a crazy story, but we were able to set up an office, and he was able to join and get involved with the company. We built something amazing together.

Keith 04:35

I assume this was Intrafinity, one of your first companies. What happened to Intrafinity? How did you build it?

John 04:42

We were in downtown Toronto with a small team, and over six or seven years we built 30 software products. It takes a lot of work to build software products, so just imagine it was nine to midnight, six days a week. We were putting out these different products with a small team.

After five or six years, I realized something was wrong. I had built a lot of products but didn't have a lot of customers—only a handful for each. I realized I was good at building products but not good at building companies. We needed to shift, so we moved into a mode where we would start to spin out companies. We took some of that technology and set up standalone companies. From that, we launched five companies. Two of them we shut down, three did well, and one did exceptionally well.

We worked in kind of boring industries—education for government, online learning for large companies. In the first six or seven years, we were building a lot of products. In the next six or seven years, we scaled these companies.

One that did quite well was in the education space. It was called Sharp School—today it's called Power School and School Messenger. We eventually got to over 10% of the US market, so 10,000 schools using it, and were able to sell that business. We joined the leadership team of the larger company and grew that to eventually 60,000 schools in the US, about 60% of the US schools. It was always fun—you'd sit down with parents who had kids in public school, and there was a 50-60% chance they were getting daily messages from our software about what was happening with their kids at school. That was really rewarding work.

The sale process was interesting. We were approached by two players. One called and said, "John, I hate competition. How about I give you a lot of money, buy your company, and then I'll have less competition." But I knew their playbook—they would buy the company, fire 80% of the staff, and move customers off our product onto theirs because we had competing products.

As I was prayerfully considering that, I thought, "I don't think that's the end of the story that I want." Another competitor showed up and said, "We don't have your products. It's complementary. We'll make this bigger company together. We'll keep your team. We'll grow it." I decided to go with that deal.

It was a great experience. I had never sold a company before. When I was in the larger firm, we were able to buy companies and roll them up. I had a team in seven different offices, including San Francisco, Toronto, Costa Rica. We bought a company, and I was over in Hong Kong and Zhuhai, China, where we had a team. It was a really exciting experience.

Many of my entrepreneurial friends said, "The moment after you sell, you've got to get out of there. You're not going to learn anything and you've got to start your next thing." But I decided to stay three years. I learned so much, including how hard it is for large companies to innovate. We were in a smaller unit in a bigger company, and it was stifling. I had to defend against all the bureaucracy so my team could be innovative.

Keith 08:00

You had to make a transition from a founder into an executive. You had to look at maybe the bigger picture in a much more detailed way. Can you help me understand, did you struggle during the transition?

John 08:16

As soon as I sold the company, I suddenly felt a little lost. Some people sell their company and the next day they leave. That's a unique experience. But in this case, I was now an executive, one of three people in the senior leadership team in this firm.

I felt this loss of identity. I was like, "I'm an entrepreneur"—I realized that was an identity I had put on, and suddenly I was now a senior executive in this firm. There was some sense of loss. It's like I didn't know who I was anymore.

In terms of skill set, there's a lot to learn. Founders, especially when you're acquired, can play a unique role. Everyone in a firm generally wants to keep their job—rule number one of being an employee is try to keep your job. But that means you're less disagreeable, you might not bring up innovative ideas because it's too risky.

Being a founder in these larger firms, you can have a strong voice. People know that you don't care if you get fired, you're going to say the right thing and call it the way you see it. So you don't have to be as political. It was a great experience. I learned a lot and grew a lot through it.

Eventually the time came where I finished my earn-out. An earn-out is when you've sold the company and they keep you there for a certain period, then the golden handcuffs fall off and you can sail into the sunset. That moment when you're done is really precious in the development of your career—these transition times are important.

I had a friend who had a company for 25 years, and I met him on the Friday which was his last day working at that firm. I asked, "Are you going to take time off, reflect on what you want to do in the next chapter, maybe take a year off as a sabbatical?" He looked at me and said, "Are you crazy? I already started my next company. I'm starting on Monday."

In that moment, I thought, "Whatever he's doing, I am not going to do it. I'm going to take a sabbatical, take a year off and try to figure out what I want to do." When I talk to that friend now, a number of years later, he regrets it. He says he should have taken time to reflect. He rushed into the next thing.

So I spent a year in transition in this sabbatical. I had a couple of questions. I was 37 years old, had done really well financially, had a lot of optionality. I love working—I love it so much that I didn't know how not to work.

The first day of sabbatical, I woke up in my home, went down to the main floor, and my wife asked, "What are you going to do today now that you're free?" I said, "I'm going to my home office to work." She said, "John, you don't have a job anymore. What are you going to work for?" I said, "I need to go find out what my work is." She responded, "John, something's wrong that you can't stop."

During that sabbatical, I started to develop skills around reflection. I really believe now that we grow at our pace of reflection. You can be busy, you can do a lot, but you need to have a practice to reflect, retool, see what you can learn, how you can redirect, and even introspect your own desires and wants. That was one of the things I started to explore in that sabbatical.

Keith 12:35

I thought it would be useful to go back in time to understand the meta culture that was driving Silicon Valley American corporate culture. Because I think a lot of the challenges that we see today are usually a byproduct of what happened maybe years ago or artifacts of the past.

For example, if you look at Silicon Valley, it's a place that drives extreme innovation but also celebrates a certain form of extreme overwork, grinding your teeth, and keeping working forever. Help me understand what was the culture like back then in terms of startup culture or corporate culture and its attitude towards work?

John 13:10

It's similar today, but there definitely was this push: work harder, work harder. I remember saying things like, "I'll sleep when I'm dead. We just gotta keep going. Sleeping's a waste of time."

In a sense, early startup building really does require an immense amount of work. It was 9 a.m. to midnight, six and a half days a week. I remember sleeping in a chair—the kind we're sitting on now—many nights. You might wonder how I slept on a chair, but I'd put my legs over one side, my head on the back, and fall asleep.

It seemed the business really required that level of work, or at least that's what I told myself. Because of that focus, we were able to push through. But at the time, I didn't have skills around how to partner with people. I was a solo founder doing it all on my own, and I hadn't yet built the emotional skills to have deep partnerships.

In terms of the context, there was absolutely this push to just work, work, work, never stop working. I think you see very high incidence of depression, even suicide among entrepreneurial founders even today. This culture persists.

There's a sense, especially in Silicon Valley, of this Superman/Superwoman type culture where founders are almost demi-gods. Like they have these special gifts and abilities, which they do, but the expectation that they're superheroes who can carry the world on their shoulders is too much. It's beyond what humans can really bear.

I think a way to work on that is to explore how you can co-create with other people. I've written a few different articles on co-creation—what are the skills you need to partner and co-create, and how do you develop this?

Keith 15:56

When you were taking that sabbatical and struggling to not work, what was that journey like of trying to understand yourself, where you fit in the work that you do, and what to do?

Because for me as a Singaporean, sometimes I read about founders who exited their business and a lot of them complain there's a void. There's this famous essay that I think the co-founder of Loom wrote after selling the business for close to a billion dollars, saying he doesn't know what to do with his life. How do you face the monster of, or stand at the abyss, as Nietzsche would put it?

John 16:29

That abyss is so fearful that many people, not just founders, will spend their whole life avoiding it and just working harder or letting other things take over them.

I started a number of practices that were new to me. A lot of people talk about them today, but I set a schedule for the morning. I wanted to do certain things every day—time to meditate and pray, time to journal to process what was going on.

During that time, I also developed a practice where I would monthly take a day away to find a retreat center. In Toronto, I found an Anglican convent—I thought nuns were only Catholic, but there's an Anglican convent with nuns. They had a ward where people could come for a day. You could rent a room, almost like a hotel room, for about $30, and sit there in silence. Those became really precious times for me because I'd bring different books and work in silence.

A precursor to this sabbatical was a couple years before when I had a psychological breakdown. We were running mobile apps and websites for about 7,000 schools in the US. Hackers started attacking our system with denial of service attacks. For a week, we just couldn't stop it. We tried so many things, but our system was off and on every hour.

Imagine an office with about a hundred employees, every phone ringing with furious customers saying the system's down. I was working 24/7 with my team trying to solve this. These hackers actually ended up taking down a big chunk of the Canadian telecom network.

Suddenly, I couldn't get out of bed the next day. My wife said, "John, I think you need to see a therapist." It had been a few days I couldn't get out of bed.

I remember going to my first therapy session and asking, "What's the point of all this? Is it just to make a lot of money and donate it?" There was a sense where I had lost all meaning and purpose in the work I was doing.

The psychological experience I had was as if someone had beaten me up in an alley. It's interesting—this is a company, it's separate from me, it's not me. But when it was being attacked, I felt like I got beaten up. I realized that my identity had fused with my business.

I've talked to many different founders. This isn't always the case—many have other jobs—but in my case, my identity had fused with the business. I had to start doing work to separate my identity so I could still be all in, but have a safer separation.

Keith 19:24

Do you think that this problem has gotten worse or has gotten better nowadays?

John 19:29

I think a lot of investors specifically select founders that have this psychological trait. Many investors will say, "I only invest in founders that have a chip on their shoulder." I've always wondered, what does that mean?

When you peel it back, it means this business they're starting will determine if they are a valuable person or not. If the business fails, the founder will be worthless. If the business succeeds, they will be really valuable as a person.

How did that get into someone's psychology? A lot of parents are very success-oriented: "I'll love you if you're successful. If you're not successful, my love is conditional." In our psyche, we can start to attach our worth to the success of what we create. In some sense that could be somewhat healthy, but often investors are looking for people where it's at an unhealthy degree.

They know what's a more powerful motivator than believing you'll be worthless if your business isn't successful? There's almost nothing more powerful to make someone go all in.

This is something I've really struggled with—do the top entrepreneurs, the successful entrepreneurs, have to be psychologically unhealthy to be successful? When you look at the biographies of Elon Musk and others—Walter Isaacson's book, for example—he leaves this question wide open. Did Elon have to have the level of trauma from his childhood with his father? Is that what made him successful?

I just don't accept that you have to go through deep, traumatic, unhealed experiences to be successful in the world. I think there's a better path forward.

Keith 21:11

Even as you recounted the story about being hit by denial of service attacks and going through that panic attack, you've come out on the other side and now you're seeing maybe a similar pattern repeat itself that's been dominant in maybe American or Western startup culture.

Even in Singapore, actually even in our part of the world, it's the same issue. We talk about the 996 in parts of Asia—working from nine to nine, six days a week. Is there a way to want well? How does one approach wanting well in the work that they do? You don't need to be a startup founder—you could be in a corporate job, could be a volunteer, could even be a startup founder. How do you approach wanting well in that case?

John 24:01

I have a friend—in North American language, a cowboy, kind of wild, spends a lot of time in Las Vegas—a very successful executive and business builder. Later, as he grew into his 50s, he got cancer.

He went through a process to treat the cancer. He had been my boss in an internship when I was about 18, and I reconnected with him about 20 years later after he had recovered. We had this powerful conversation where he said, "John, cancer was the best thing that ever happened to me."

I was floored. "What are you talking about? Cancer is terrible." But he said, "John, I was going down a path that was self-destructive, and cancer was this crucible experience that made me redirect."

It's interesting because he would reflect and say, "I wasn't wanting well, but now I'm wanting well." There's this sense where we look back at our younger selves and say, "I didn't know what I was doing. I was running after all the wrong things."

I think there's a journey to figure out if you want well. There are a number of layers to it, but one to start with is what I call "wanting from windows." In life, a lot of people go to the department store window or Amazon carts or social media, looking through that window and saying, "I want that."

There's interesting research on this from Stanford professor René Girard, who wrote a series of books. They're hard to read, fairly academic, but Luke Burgis has written a book called "Wanting" that makes a more accessible version of his theory.

René Girard basically said that as humans—and this is a shocking insight—we fundamentally do not know how to value things. We value things based on how other people value them. If I have a friend I trust and he says a new restaurant is amazing, I'll check it out and believe it's valuable. It'll even taste better because my friend told me it was amazing.

Girard argues that we have what he calls "mimetic desire." We don't have true desire ourselves. Mimetic means we copy—we copy the desires of others and adopt them as our own, and we don't know that's happening. It's a subconscious process.

You see this in financial bubbles. Why are there bubbles? Because there's momentum. Why is there momentum? Often because everybody's going for it. Meme stocks are things where other people said it's valuable, even though everyone knows there's no value to it, but you go for it anyway.

Girard observed that we don't actually know how to value things, which is shocking. If that's true—and I believe it is—the most important thing you can do is choose the right heroes.

Warren Buffett has a line—I won't quote him perfectly—but he said, "If you want to live life well, not just make money, if you can pick the right heroes, that's half the battle." That's consistent with Girard's view that our wants are determined by who our heroes are.

As we grow, our heroes evolve and change. We need to be deliberate about who the heroes are that we look to for triangulating what's valuable in life.

For example, a decade ago at a conference with entrepreneurial friends, one guy showed up and said, "I got the second Tesla in Canada." He was excited and drove it to the conference. About ten of us gathered around the car saying "ah" and drooling, wishing we had one too.

But I sat there thinking, "What is happening right now?" Later, I had other friends who said those early Teslas were terrible—falling apart all the time, needing constant repairs. But one of our friends who we all trusted was telling us this was the most amazing car ever, and we all adopted that perspective of valuing.

A second step, which is much harder, is recognizing that a lot of our wants come from our wounds. I was with a friend who had sold his business for hundreds of millions of dollars. He had finished about three months before, with a quick exit. He was trying to process this challenge of being on the other side of success and feeling lost and confused about the next stage.

In this moment of reflection, he said, "John, when I was a kid, my parents fought about money all the time. We didn't have enough money. My mom and dad were fighting all the time." You can imagine him in middle school with his parents fighting about money. He said, "I resolved when I was young that I never wanted to fight about money in my whole life."

Then he said, "John, I think I just spent the last 15 years of my life trying to solve that problem. But I need something better to live for now."

What I see in that story is a wound. Now he has a different problem—he has too much money, not too little. But there was a wound from his childhood, and he spent 15 years trying to solve it. That ended up looking like a company that made him financially rich. But he spent 15 years operating from this subconscious layer. He was blind to it, and only figured it out after he sold the company.

In my own journey, there's something similar. I was the oldest of six children. My mother was a homemaker, my father was in finance as a CFO in a distribution business. Our family was crazy and busy with so many people. We did not have hired help like you'd have here in Singapore.

I remember a moment at the dinner table when my dad was exhausted from work and whatever problems we created. I was trying to engage him in conversation, and it was hard—he wasn't talking much. Then I asked a question about his work, the business he was in. He lit up and started sharing all about what was going on.

A little light bulb subconsciously went off: "If I talk about work stuff, I can really get my dad's attention." I didn't know it at the time, but that thought rooted deep inside my subconscious.

About 15 years later, I was in Canada at a national dinner celebrating a Young Entrepreneur of the Year award. My dad was next to me, with one of the ministers of innovation for the country on my other side. Suddenly they announced, "Winner, Young Entrepreneur of the Year Award goes to John Carberry."

I went up to give a speech, not really knowing what to say since it was the first award I'd ever received. When I sat down, my dad said, "Good job, son. You did a good job."

There was some sense where I had spent 15 years trying to get my father's affirmation, building that company and getting to that national award level. So we want from our wounds. I had this wound of wanting more of my father's time, and I did a lot to get it.

This is challenging stuff—how do you get on the surgery table and start to work on these wounds? One suggestion I'd give is a book called "The Grief Recovery Handbook" by two psychologists who run a center to help people process different losses.

I had one of the most beautiful experiences of my life related to this book. Someone who had been a mentor to me for many years, about 20 years older than me, came to me and said, "John, I know your mother passed away recently." His wife had just passed away. He said, "This loss recovery handbook has a six-step process to take a loss—like loss of your spouse."

There are many other kinds of losses—loss of a job, traumatic things, loss of safety, loss of relationships, loss of trust. He asked, "Could you go through this book with me? The book is set up where you pair up with someone and work on your losses together."

The book has a process where you list all the losses you've experienced in your life. The first week teaches that no one knows how to process loss. We just carry these losses around with us our whole life. A loss I experienced when I was 10, I'm still carrying at 40 or 50—the losses don't go away.

The book argues there must be a process to heal or "complete" losses. We went on this journey to realize we don't know how to process or complete losses.

When I listed all 40 losses I'd experienced, it was interesting—for many, I had no emotional reaction. But there were about five where I felt an emotional reaction. I realized these were losses I was still carrying, and the book gave us a path to process them.

So I think it's important to understand that yes, we want from windows—the department store of things we're looking at from our friends—and we need to pick good heroes. But we also carry these losses and need to work to heal them. Otherwise, we might spend 15-20 years of our life just trying to heal these losses.

Keith 34:06

Even as I was hearing you talk about René Girard, I can't help but recall what Peter Thiel talks about—exploiting mimetic desires to build companies with strong network effects.

It seems inevitable that with that philosophy as an operating principle, you'd eventually want to strive to be a monopoly as Peter Thiel suggests every startup should. But with monopolies, you create a lot of negative externalities and market distortions. When entrepreneurs start their business, they don't really think about negative externalities or the ecosystem around them. It's only about what they want.

John 34:49

One of the stages of wanting well is what I would call wanting from wovenness. I'm just finishing up an article on this, but essentially wanting well does involve a very individual process. We need to tune our wants and work through these wounds and losses so we're not operating from distorted desire.

But ultimately we need to be in community to do something amazing in the world. I think there's a two-dimensional layer to it. One is that we want to be in high trust relationships. There are different cultures that are very transactional, but I want to be in transformational relationships, not transactional ones.

Transactions have their place—I want to use Grab or Uber for a quick transaction to get from here to there. But for the meat of my life, I want transformational relationships. There's a journey to build and foster trust.

The other dimension is: can we have a creative moral imagination of how the world could be a better place? There are many groups that involve creating trust—you can be at a country club where you have meals together and build trust. But there aren't as many groups that have both trust and a creative moral imagination of what they could do in the world.

Ultimately, I think the highest level of wanting we can have is when we can merge with other people and want something together—have this imagination of the new world we want to create.

That brings us to business itself and creating businesses and entrepreneurship as a vehicle. What is a business? Is it just an entity that creates money? Money and profit are byproducts of what the business does. There has to be some purpose, some challenge it's solving, something new in the world it's creating.

The entrepreneurial process is amazing because we get to imagine. If you're an executive hired into a cigarette company, what do you do? You say, "Can I be transferred to the reduced harm division? To the vaping division because it's not as bad as the cigarette division?" The DNA of that business is already baked in. You can't do that much, you can't imagine a very different world.

But in the entrepreneurial journey starting from scratch, you get to craft the DNA of what you create. The way I'd articulate it is that the purpose of business is to solve problems or bring from the future to the present this new reality for people and planet—to profitably solve these problems.

With that in mind, we're searching for how we can solve an amazing problem. How can we bring the future to the present? That's an amazing journey, and we get the opportunity as our businesses grow to do it with co-founders and other people. It's an absolute privilege.

Keith 38:11

You're doing something very contrarian to what most typical venture studios or investors are doing. One, you're trying to create a business with a richer moral imagination. Second, you're finding well-adjusted founders, which is almost not what people look for because they're ultimately looking for the highest return on investment.

By definition, and alluding to your earlier points, they usually look for the most obsessive founder that really ties themselves to the ship. Regarding moral imagination, it's seen as a luxury, not a necessity.

So what do you think makes a good ideal founder in the partners you work with? What makes a good founder in building that kind of brighter future?

John 39:15

My role as a managing partner at FutureSite—we're a venture studio, or another way to say that is "team co-founder." We get about a thousand founders a month applying to us saying they'd like us to be their co-founder in the next thing they build. Generally, we're picking about one person every one or two months to co-create our next venture with.

Then our whole team wraps around this individual or two individuals to maximize the success of the venture we create. It's all in the AI space around how we can take reasoning—with its dropping cost—and do something brand new, typically in a very vertical industry.

We get excited about founders who have built companies before and have unique expertise in certain verticals. The whole process takes about a year and a half to two years. We start at an ideation stage, trying to find the best opportunity. Then we go into a validation stage where we test many versions of the idea to ensure we have the highest breakout opportunity.

After that, we form the company, build the product, get initial customers, invest ourselves into the business, and through our network go through a fundraising process to bring more capital into the business to make it successful.

One interesting area is what I would call "return on character." What's the return on investment in someone's character? There's some interesting research that highlights that leaders with higher levels of character—which you can break down into many different attributes—have much higher returns. Some good research has been done in the public markets on this. So character and different attributes around that is one thing that does produce higher returns.

In terms of strapping yourself to the mast, I think you can do that in a healthy or unhealthy way. You can strap yourself to the mast out of a wound, or memetically. I did that—I was strapping myself to the mast of my business, with the wound of wanting my father's affirmation as a primary motivator.

But if you can connect deeply to the purpose of what you're doing, of the business you're creating, that is beautifully positive and can also have you strap yourself to the mast. Another term for this would be "having skin in the game."

Skin in the game is one of the most positive moral traits. If you think of financial markets generally, investment managers take in capital and manage it with a standard fee structure—they take 2% a year of the fees and get 20% of the upside. But how much downside do they have? If they lose a lot of money, there's no downside. They might have to get a new job, but they're not losing their own money.

The financial services industry has designed a system where you can get upside with no downside. A lot of people would think that's amazing, but fundamentally, I think the most moral force is where we have skin in the game—we get upside and take downside in whatever we're doing. That's a very powerful thing.

Your motivation could be from wounds, but it can also be from purpose. If you can latch onto a beautiful purpose that your business is fulfilling, that can be really meaningful work and more sustaining long-term than strapping yourself to the mast.

Keith 43:18

Have there been founders that you've backed or supported that you think live up to or exemplify the kind of virtues that you've espoused so far?

John 43:31

There's a business we've been working on in the construction technology space with an amazing founder, Calvin. When we started to dig into the construction technology industry together, we realized—at least in North America, I don't know about other markets—that there was suddenly a new problem.

In the past, construction firms really just wanted to get sales contracts and then deliver. But there started to not be enough construction workers in North America. They were getting older, retiring, and suddenly everything changed. The job of construction firms became to retain these workers in the field.

As we dug into it, we talked to people in the head office who would say, "We just lost another foreman, and we have more contracts than we can handle. We don't have the staff to deliver it." Then we'd talk to the workers, who would say, "This company doesn't value or appreciate me. If I get paid 25 cents more, I'm out of here."

There was this gap where the leaders needed their workers and wanted them to stay, but the workers were completely disenfranchised. That was a very interesting space, and Calvin had worked in the construction industry before. He knew that gap viscerally.

We were able to build a system that, when Crewscape goes into construction firms, gets 15% labor productivity improvement. The margins on these projects are often 4-5%, and 50% of the cost is labor. So you're doubling the profitability of these projects when you put this system in.

This system fundamentally solved that gap where there was better alignment between the folks in the office and the workers in the field. That was a really amazing journey that we're still on together, where we were able to identify this gap where workers needed to be led better and more aligned with the outcomes. When we did that, we got this beautiful outcome where everyone's so much happier.

Keith 48:04

To zoom out a little bit, I've interviewed a lot of VCs and they all have different theses. You seem to have a very high premium on the character of the founders that you work with and a belief in this creative and moral reimagination of a world where your business can positively improve not just the clients you work with but the greater ecosystem around it. So what do you look at, what are the filters or criteria you use in terms of project selection or the startups that you choose to help?

John 48:50

This vision of a creative moral imagination is something that frames my whole life. There are many areas where I am partnering, not just in the work in FutureSite building companies, but in nonprofit areas and impact investing that I'm involved with on behalf of my family. This desire to be at that level of wovenness where I'm in high trust relationships with some creative moral imagination.

When I take this down to business building, it practically means we're building AI-focused software businesses. I'm very open-tented on what makes a better world—if we make something more efficient, that's a small movement towards a better world. So don't get me wrong—everything doesn't have to be just about peace or solving climate change. I think if we're creating value, even in the smallest things—helping someone be more compliant, helping people get into better universities that fit them, helping something in the doctor's office, or building a company on how to better assess elderly people for dementia so they can get care earlier—there are so many small things where you can have a positive impact.

Actually, if someone's going to pay you for something, as long as you're not a drug dealer, generally you're getting paid for something positive. I just frame my life around wanting to be in that space.

Specifically for FutureSite, we see a unique opportunity around AI. We're partnering with repeat entrepreneurs who want to build their next thing. They're going through a process of trying to pick who their co-founder is. They can look around at people they've worked with before, but there's also this new opportunity to co-found a business with a venture studio.

It's an interesting comparison—you can have an individual, but with FutureSite, you get a whole cross-functional team with different capabilities that we bring to the table from day one. When founders look at that comparison, they say, "Yes, I want to work with FutureSite" because of all these capabilities that will maximize the success of what we're doing.

What I'm most excited about right now is this interesting space where the cost of reasoning is going towards zero. What does the world look like when you have unlimited reasoning ability? A lot of us, especially in Silicon Valley, are trying to imagine what that new world looks like.

Some things are easy to see—there are certain roles today that we could just replace with AI. But there are also cases where if you had a hundred times more reasoning ability for the same cost, you might do entirely new things. That's a really exciting world.

I'll give you an example. We're building a company called Addy with a founder, Andrew, out of San Diego. Andrew realized that the wealthy 1% in the US and globally have the ability to hire college admissions coaches or advisors. These coaches can be really expensive—sometimes families are paying $20,000 a year for four years of high school to have their kids coached to get into better schools.

He looked at that and said, "This is a really unfair financial advantage." It's a professional services business—the college advisor charges hundreds of dollars an hour, and there just aren't enough of them. But what if we could, using AI, create a hundred times more of these college advisors?

That's exactly what we're doing. It means that the whole middle class could have access to this level of coaching that wasn't available before—maybe the next 50% of the population. That's a different world. It could be a really exciting place.

Keith 54:07

My last question for you is, if you had one piece of advice to give to a fresh graduate entering the workforce, what would it be?

John 54:14

Be excellent at what you do. And then the sky's the limit.

Keith 54:20

Well, with that, thank you.

John 54:21

You're welcome. Thank you.