The Exchanges

Q price sensitivity when entering, and how do you think about effectively pricing these assets? And also, is it challenging because they're tech founders, and they see tech crunch, and they see hundreds of millions of dollars of valuation, and it's a very different thing if you're doing a social networking. A fisherman or whatever that may be. How do you think about price sensitivity and communicating that to the founders?

A I mean, at the end of the day, the price to the founder, we're not talking typically about venture backed businesses. We're often talking about businesses that have been bootstrapped or started by accident by a founder. And they're often five to 10 years in, they have a nice income from the business and it's profitable. And so what we do is we basically pay a fair price based on where the business is at. And that's typically based on what earnings are expected to come out of the business over the next five to 10 years. And then the other way we think about price is just risk. So yes, it's paying us a million dollars a year in profit, but will that million dollars a year disappear as soon as the Google SEO algorithm changes or ad rates go up? And so if it's risky, we're willing to pay a lower multiple. And if it's less risky and there's a competitive moat, we'll pay a much higher multiple.

AI assessment note: “we basically pay a fair price based on where the business is at”

Q price sensitivity when entering, and how do you think about effectively pricing these assets? And also, is it challenging because they're tech founders, and they see tech crunch, and they see hundreds of millions of dollars of valuation, and it's a very different thing if you're doing a social networking. A fisherman or whatever that may be. How do you think about price sensitivity and communicating that to the founders?

A I mean, at the end of the day, the price to the founder, we're not talking typically about venture backed businesses. We're often talking about businesses that have been bootstrapped or started by accident by a founder. And they're often five to 10 years in, they have a nice income from the business and it's profitable. And so what we do is we basically pay a fair price based on where the business is at. And that's typically based on what earnings are expected to come out of the business over the next five to 10 years. And then the other way we think about price is just risk. So yes, it's paying us a million dollars a year in profit, but will that million dollars a year disappear as soon as the Google SEO algorithm changes or ad rates go up? And so if it's risky, we're willing to pay a lower multiple. And if it's less risky and there's a competitive moat, we'll pay a much higher multiple.

AI assessment note: “typically based on what earnings are expected to come out of the business”

Q too interested. How does COVID impact the revenue models and kind of revenue protection that you have? Because when you have venture-backed companies, you know, some of them have three to five years of runway and often large fundraisers. With this model, it's obviously leaner, and although profitable, the profits can and often do get hit. How do you think about COVID's impact on the kind of profitability and margin?

A So like anybody else, we don't know what the second and The consequences of the lockdown will be. I'd like to think that most of our businesses participate in a knowledge economy online, and so we have a huge advantage in that all of our companies operate remotely. That's always been part of our DNA, and if they're not remote, maybe they have an office, but everybody's free to work remote, so we've been able to pivot really easily into that. Some of our businesses will certainly be affected, but generally their low Fixed costs. And so we can scale costs down as needed to make sure that we can continue to be sustainable. And then there's other businesses that kind of be anti-fragile in an environment like this. So one example of that is Dribbble, which is the largest social network for designers. Where do designers go when they're stuck at home, but they want validation and feedback and a sense of community? Well, they're going to go to Dribbble. We also own the largest remote job board in the world. I think that's going to do very well in this environment as more companies start hiring remotely. We also own a meal planning app called me lime and people are cooking a lot more. They're trying to plan their groceries out. They're trying to make a dollar go further. That does well in an environment like this. The places where we're going to be hit are more on our services businesse…

AI assessment note: “Some of our businesses will certainly be affected, but generally their low Fixed costs.”

Q too interested. How does COVID impact the revenue models and kind of revenue protection that you have? Because when you have venture-backed companies, you know, some of them have three to five years of runway and often large fundraisers. With this model, it's obviously leaner, and although profitable, the profits can and often do get hit. How do you think about COVID's impact on the kind of profitability and margin?

A So like anybody else, we don't know what the second and The consequences of the lockdown will be. I'd like to think that most of our businesses participate in a knowledge economy online, and so we have a huge advantage in that all of our companies operate remotely. That's always been part of our DNA, and if they're not remote, maybe they have an office, but everybody's free to work remote, so we've been able to pivot really easily into that. Some of our businesses will certainly be affected, but generally their low Fixed costs. And so we can scale costs down as needed to make sure that we can continue to be sustainable. And then there's other businesses that kind of be anti-fragile in an environment like this. So one example of that is Dribbble, which is the largest social network for designers. Where do designers go when they're stuck at home, but they want validation and feedback and a sense of community? Well, they're going to go to Dribbble. We also own the largest remote job board in the world. I think that's going to do very well in this environment as more companies start hiring remotely. We also own a meal planning app called me lime and people are cooking a lot more. They're trying to plan their groceries out. They're trying to make a dollar go further. That does well in an environment like this. The places where we're going to be hit are more on our services businesse…

AI assessment note: “we can scale costs down as needed to make sure that we can continue to be sustainable.”

Q Can I ask, in the cases where there is like these huge outcomes available, like Dribbble, I mean, Dribble, the largest social network for designers, that is absolutely a venture outcome, and it could be a venture play in many respects. How do you feel about VCs encroaching on the tiny portfolio, and how would you like to work with the venture community?

A I'm not anti-venture. Like, I really want to make that clear. We just haven't run our businesses that way, and we haven't raised venture. So I would say that if we had a business that was obviously in need of a large amount of capital, And we needed somebody at the table who was willing to take a big risk where we knew that in order to grow it into a billion dollar business, we'd need to burn a hundred million dollars, but that's the only way to capture the market. I would absolutely do that. I would be calling benchmark and Excel tomorrow, but I just don't see that. We haven't observed that in our portfolio. And I think about Dribbble is one of those New Zealand businesses. Every single day, hundreds of thousands of designers wake up Every morning, and they punch Dribbble into the URL bar. You know, we don't need to go out and buy customers. They just naturally organically appear, and because Dribbble is the largest, the largest network is generally where people go. People want to be in a social network with others, and so when I think about what we could do if we had fifty million dollars in the bank, it doesn't look very different than where we're currently at bootstrapping the business and continuing to ensure its Profitable. But again, like, if we saw an opportunity, we absolutely would. That just hasn't been something we've seen yet.

AI assessment note: “if we saw an opportunity, we absolutely would.”

Q So do you think like, hey, this isn't a sink the boat decision. Let him realize that on his own, or this is, and I have to intervene. Is that the decision making for you?

A In the businesses that we own, I'm never going to let a CEO make a sink the boat decision, right? But if it's a two-way door, if it's something where, look, I think this business model idea is hokey, but they've got it in their head as the greatest idea ever. If I go in and I say, we're not doing that, that's a bad idea. They're just going to resent me, and they're always going to bring that up at future board meetings. Well, we could have done that thing, and we would have grown this year, but You know, you held me back from doing that, and so as long as it's a two-way door, I will always let someone make a mistake, and I might register, like Bezos, what does he do? It's like, disagree but commit, right? Saying, I don't agree, but I'm going to commit to let you do this. So we do that a lot. If a CEO is to come along and say, I want to go spend ten million dollars on a cryptocurrency strategy with a five percent chance of success, I think we'd have a very different conversation.

AI assessment note: “I'm never going to let a CEO make a sink the boat decision”

Q because you said about kind of the growth of some of those businesses there, and I had someone on the show the other day, and they said about kind of growth versus profitability and it being levers and really them being fundamentally at odds. You increase growth, you decrease profitability, and vice versa. I'm intrigued. How do you think about this, given your perspective, and would you agree with that?

A So I would say like we just have a culture of profitability. So because we started in Canada, we really had no access to capital. We had to focus on profitability and understand our P and L and make sure that if we had 30,000 dollars in the bank at the beginning of the month, we had a little more than that at the end. Because that's so part of our DNA, we really exclusively buy profitable businesses or at the very least businesses that can be immediately pivoted to profitability. Now, Obviously, we think there's many instances where a company should forgo profitability to grow, but the key here is sustainability. If I can spend a dollar on marketing and make it turn into a dollar 50 in three months, then absolutely, we should check that and cut that check a million times. However, if it's one dollar turning into 30 cents over two years, I really don't think that's a good use of capital, and I see way too many venture-backed Buying 30 cent dollars to show growth and get their next round of funding. So we aren't anti-growth. We're just anti-unsustainable growth. And, you know, regardless of our focus on profitability, almost all of our businesses are growing their top line and their bottom line at 30 or 40% a year and doing it profitably. I think it's one of these odd beliefs that people think they need to burn money to make money. We just haven't seen that in reality.

AI assessment note: “We aren't anti-growth. We're just anti-unsustainable growth.”

Q Can I ask, in the cases where there is like these huge outcomes available, like Dribbble, I mean, Dribble, the largest social network for designers, that is absolutely a venture outcome, and it could be a venture play in many respects. How do you feel about VCs encroaching on the tiny portfolio, and how would you like to work with the venture community?

A I'm not anti-venture. Like, I really want to make that clear. We just haven't run our businesses that way, and we haven't raised venture. So I would say that if we had a business that was obviously in need of a large amount of capital, And we needed somebody at the table who was willing to take a big risk where we knew that in order to grow it into a billion dollar business, we'd need to burn a hundred million dollars, but that's the only way to capture the market. I would absolutely do that. I would be calling benchmark and Excel tomorrow, but I just don't see that. We haven't observed that in our portfolio. And I think about Dribbble is one of those New Zealand businesses. Every single day, hundreds of thousands of designers wake up Every morning, and they punch Dribbble into the URL bar. You know, we don't need to go out and buy customers. They just naturally organically appear, and because Dribbble is the largest, the largest network is generally where people go. People want to be in a social network with others, and so when I think about what we could do if we had fifty million dollars in the bank, it doesn't look very different than where we're currently at bootstrapping the business and continuing to ensure its Profitable. But again, like, if we saw an opportunity, we absolutely would. That just hasn't been something we've seen yet.

AI assessment note: “I'm not anti-venture. Like, I really want to make that clear.”

Q this is totally off the bat, but I'm too interested. I constantly oscillate between thinking that we'll see the unbundling of social networks into your Dribbble-like communities of the world, and then I also think, absolutely no, we won't. We'll see the bundling into Facebook groups, LinkedIn groups, whatever, incorporate into the main platforms. Where do you sit on the unbundling versus bundling of very specific niche communities and groups?

A Well, that's a really tough one. Like, you think about meetup.com, for example, which is a business that we looked at buying, and we just couldn't wrap our heads around it, because ultimately, when it comes to social networks, usually the largest network always wins. So you could see this with Google versus Yelp. Yelp had built this originally niche community. It had gotten to scale. It became very large. Everyone looked at it and went, okay, well, they have this tremendous moat, which is all of these user reviews. It would take 10 years for anyone to recreate these user reviews. Well, it turns out with Google, having Android and Google Maps, they can just ask every single person on earth how the restaurant was that they went to last night, because they know that they'd visited it via Google Maps, and suddenly Google Maps has better data and blows Yelp out of the water. So I think in instances like that, absolutely, it can be highly disruptive, but I always think, like, Dribbble is a bit of a unique snowflake. I mean, designers are Are very, very sensitive to anything seeming corporate or being part of something big or commercial, and I think that because it's a creative community, there's a risk in that, you know, maybe we mess it up and do something that's too aggressive, but there's also this huge blessing in that they don't want to be part of something big. They want to set…

AI assessment note: “ultimately, when it comes to social networks, usually the largest network always wins”

Q Not at all, but I would love to kick off with a little on you. So tell me, how did you make your way into the wonderful world of tech and startups? And what was that founding moment for you with Tiny in a very succinct three to four minutes?

A Yeah, I've really had three careers. So accidental entrepreneur, CEO and operator, and then now investor. Basically, when I was in high school, I started a tech news site, and it just totally took off, and so I started getting hundreds of thousands of visits to this site. I started writing news. I hired a team of writers. I started selling ads and negotiating ad deals, and so I basically got my MBA in high school running this website and pretty much skipped all of high school, and so through that, I got to interview Steve Jobs. I got to Travel all over the world and have all these incredible experiences, but at the end of it, I was kind of left not sure what to do. What I ended up doing when I graduated high school is I decided to move to Silicon Valley. I really wanted to go work at Apple or Google and learn how a big company was run, but I didn't have a ton of money, and I decided that I would start freelancing to make some extra money, and one really great insight I had was that If I pretended to be an agency, I could probably win more work. And so I came up with the name metal lab. I designed a very, very slick looking site that made me look like a big agency. And I started using the sales skills that I learned running this website. And I called up founders of Silicon Valley companies that had raised money. I'd go on tech crunch and see that someone had done a raise and I'd…

AI assessment note: “Basically, when I was in high school, I started a tech news site”

Q kind of burning money to make money, we've seen many do it over the last five or 10 years in venture. It's said to a lot of, you know, sadly, companies shutting down. I am intrigued, because as we said there, it's a very different model to venture. How do you think about loss ratio stay within the portfolio, and then diversification in terms of portfolio construction as a result?

A So we don't really think a lot about portfolio construction. We really just try and focus on Individual companies and buying wonderful companies. We look deal by deal and evaluate whether we think this is a business that can stand the test of time and exist in two to five years. I mean, for me personally, I'm very comfortable having a few eggs in a basket and watching it closely rather than diversifying to death. For 10 plus years, one of our biggest business was Metalab, and that was kind of one big egg. I'm pretty comfortable if I deeply understand the business and And so we don't really think about that. In terms of loss ratios, I'm not counting on having losses. We occasionally will, and we will have business failures, but they'll more look like softness and bad returns. I doubt we're going to have zeros. It's just not like a venture game. These are generally businesses that will continue to exist. They might just be less profitable than we expect.

AI assessment note: “So we don't really think a lot about portfolio construction. We really just try”

Q So do you think like, hey, this isn't a sink the boat decision. Let him realize that on his own, or this is, and I have to intervene. Is that the decision making for you?

A In the businesses that we own, I'm never going to let a CEO make a sink the boat decision, right? But if it's a two-way door, if it's something where, look, I think this business model idea is hokey, but they've got it in their head as the greatest idea ever. If I go in and I say, we're not doing that, that's a bad idea. They're just going to resent me, and they're always going to bring that up at future board meetings. Well, we could have done that thing, and we would have grown this year, but You know, you held me back from doing that, and so as long as it's a two-way door, I will always let someone make a mistake, and I might register, like Bezos, what does he do? It's like, disagree but commit, right? Saying, I don't agree, but I'm going to commit to let you do this. So we do that a lot. If a CEO is to come along and say, I want to go spend ten million dollars on a cryptocurrency strategy with a five percent chance of success, I think we'd have a very different conversation.

AI assessment note: “I'm never going to let a CEO make a sink the boat decision”

Q How to think about your relationship to money, and you'll always think, when I have X, I'll be happy. When I have one million, I'll be happy. Ten million, I'll be happy. And that moment never comes. It never came to him, and it doesn't come in human nature. I'm intrigued. One of your core principles is people over profits. How do you think about your personal relationship to money?

A So, I grew up in Vancouver, and my dad was an architect, and money was always really tight. He'd run his own architecture firm, and architecture is just a difficult industry. And so, Money was always this thing that my parents fought about and were stressed about, and at the same time, growing up in Vancouver, it's quite a wealthy city, and I happened to be in the catchment area for a wealthy public school, and so I ended up going to this public school where I was surrounded by the children of millionaires, and everybody's dad drove a Porsche, and they had ski chalets, and they went to Hawaii for vacations, and, you know, I'd go over to their houses, and they'd be these palatial mansions, and I just looked around and went, This is bullshit. I want this. I can't believe I've been so hard done by. And all I wanted was to get the things that all these other people had. And so when I started making money, I went out and I bought a fancy car and I bought nice clothes and fancy stereos and all these things. And I didn't find that it had any impact on my happiness. The only thing that had an impact on my happiness was not stressing out about rent and Knowing I had enough money in the bank that I was comfortable for two or three months. I could go and eat when I wanted and drink what I wanted. And so once I kind of achieved Maslow's hierarchy of needs, I realized, well, there's no addi…

AI assessment note: “once I kind of achieved Maslow's hierarchy of needs, I realized, well, there's no additional benefit”

Q Yeah, absolutely. They can, which is absolutely why my question on price I was so interested by. I'm also interested because I've read a lot of your writing and as we were chatting about before the show, listen to many of your podcast episodes before, and you've said before on paper, I'm a terrible CEO. So why is that?

A Well, I think like a lot of founders, I'm very urgent and I love Doing things quickly. I love ideas. I love strategy. What I don't really like is implementation and follow through and managing people. And what I've realized is that I'm very good at laser focusing for a short period of time on one company, deal, idea, strategy, whatever it is, but I don't enjoy spending the next 60 days implementing a plan and building that plan. To be honest, yes, I can run a company. I've done it. I did it for 10 plus years, and I was very successful at it, but I find one company, for me at least, isn't enough. I wanted more diversification of thought. I wanted to be able to jump into different ideas and different types of businesses, and I realized I just love business. I'm like an inch deep and a mile wide, and so it really suits me well to invest because it allows me to be on a High board level and interact with all the CEOs and understand all their businesses and help them grow them. But at the end of the day, I'm not managing people. I'm not overseeing implementation of ideas. And at the end of the day, there's people who love doing that. And I love to just step out of their way and let them do it because I would just not be happy doing it. I didn't enjoy being a CEO and running a large company. I like running a five person company or a

AI assessment note: “What I don't really like is implementation and follow through and managing people.”

Q I mean, yeah, I totally agree. David is just so cool. Tell me, your father pointed to a gas station on a drive with you once and said, if you don't go to college, you could work there. Do you find you give similar career advice? I guess, what career advice do you find yourself often giving?

A No, my, for the record, my dad was dead wrong. I think school is often a waste of time, especially if you're in tech. My number one piece of feedback to people is, Get experience. If you want to be in business, start a business. Don't do an MBA. It's a little bit like someone coming to you and saying, I'd like to be an Olympic runner, and that person would not go to running school. They would just start running every single day longer and longer, and I just find it totally insane because you get all these kids that have spent four years learning about business, but they've never actually been involved in a business or learned anything.

AI assessment note: “My number one piece of feedback to people is, Get experience.”

Q kind of burning money to make money, we've seen many do it over the last five or 10 years in venture. It's said to a lot of, you know, sadly, companies shutting down. I am intrigued, because as we said there, it's a very different model to venture. How do you think about loss ratio stay within the portfolio, and then diversification in terms of portfolio construction as a result?

A So we don't really think a lot about portfolio construction. We really just try and focus on Individual companies and buying wonderful companies. We look deal by deal and evaluate whether we think this is a business that can stand the test of time and exist in two to five years. I mean, for me personally, I'm very comfortable having a few eggs in a basket and watching it closely rather than diversifying to death. For 10 plus years, one of our biggest business was Metalab, and that was kind of one big egg. I'm pretty comfortable if I deeply understand the business and And so we don't really think about that. In terms of loss ratios, I'm not counting on having losses. We occasionally will, and we will have business failures, but they'll more look like softness and bad returns. I doubt we're going to have zeros. It's just not like a venture game. These are generally businesses that will continue to exist. They might just be less profitable than we expect.

AI assessment note: “So we don't really think a lot about portfolio construction.”

Q because you said about kind of the growth of some of those businesses there, and I had someone on the show the other day, and they said about kind of growth versus profitability and it being levers and really them being fundamentally at odds. You increase growth, you decrease profitability, and vice versa. I'm intrigued. How do you think about this, given your perspective, and would you agree with that?

A So I would say like we just have a culture of profitability. So because we started in Canada, we really had no access to capital. We had to focus on profitability and understand our P and L and make sure that if we had 30,000 dollars in the bank at the beginning of the month, we had a little more than that at the end. Because that's so part of our DNA, we really exclusively buy profitable businesses or at the very least businesses that can be immediately pivoted to profitability. Now, Obviously, we think there's many instances where a company should forgo profitability to grow, but the key here is sustainability. If I can spend a dollar on marketing and make it turn into a dollar 50 in three months, then absolutely, we should check that and cut that check a million times. However, if it's one dollar turning into 30 cents over two years, I really don't think that's a good use of capital, and I see way too many venture-backed Buying 30 cent dollars to show growth and get their next round of funding. So we aren't anti-growth. We're just anti-unsustainable growth. And, you know, regardless of our focus on profitability, almost all of our businesses are growing their top line and their bottom line at 30 or 40% a year and doing it profitably. I think it's one of these odd beliefs that people think they need to burn money to make money. We just haven't seen that in reality.

AI assessment note: “We aren't anti-growth. We're just anti-unsustainable growth.”

Q a couple of things that are striking. I think the first for me would be, you mentioned, obviously, also being on boards before. I've recently become a board member, you know, over the last 18 months on my first couple of boards. What would your advice be to me on what makes a great board member, and how do you think about being the best board member you can be?

A Well, I think the biggest thing to remember is that you're not the CEO's friend, that you're not there to be a buddy. You're there to actually ask probing questions. And to rub their nose in the consequences of what could go wrong. But one of the things I've also learned is that on a board, even when you own the entire company, you can't dictate what they need to do. You can only guide and you can set guide rails. And so at the end of the day, you're ultimately deciding, is this the right person to run the business or not? That's the key question. You're also thinking about incentives. How do I align this person with the outcome that I want? And ensuring that they're totally aligned with your goals. And other than that, like you could see one of the things that's been interesting to me, and I've been on venture boards, I've been on private equity backboards, and then the boards of our own companies. And I've seen this over and over again, where I've experienced something and I see the CEO making the same mistake and I try and tell them, and I've found that generally the CEO needs to actually go take the fork and Stick it into the electrical socket and realize that he gets zapped, which is unfortunate and infuriating because you're sitting there like a slow motion train wreck saying, oh my God, he's making this mistake. I don't want him to do this. It's going to ruin the company…

AI assessment note: “the biggest thing to remember is that you're not the CEO's friend”

Q Can I ask, we mentioned the hiring element there. How do you determine greatness in a role where you're not equipped yourself? So... Be it for me, I'm not an engineer. If I'm doing CTO candidate interviews for portfolio companies, how do I determine greatness in those candidates when I'm not an engineer myself? How do you think about that?

A Well, I think you look at the outcomes, right? So we've learned this with hiring CEOs. So when we're hiring a CEO, we're looking at their resume and going, have they done this before, right? So if you're going to go and build a new deck, you're going to hire a red seal carpenter. And so I'm going to go, well, how many decks have they built? How many years have they been a carpenter? And so we'll go out and we'll recruit somebody who has run a similar business at a bigger scale. And we'll say, okay, this is going to massively increase our odds of success. Whereas if you hire somebody for potential, which is what I used to do, I'd meet somebody and go, I love this person's moxie. They're really sharp. They move really fast. They seem to kind of understand marketing. I think they can be a good CMO. We'll grow them into that. That's always failed. Which seems like such a simple concept of just hiring people who have done it before, but, um, for some reason we don't do that because we don't know what those people look like. So I like to try and flip it around and just go, have they achieved the outcome I want in the past?

AI assessment note: “have they achieved the outcome I want in the past?”

Q a couple of things that are striking. I think the first for me would be, you mentioned, obviously, also being on boards before. I've recently become a board member, you know, over the last 18 months on my first couple of boards. What would your advice be to me on what makes a great board member, and how do you think about being the best board member you can be?

A Well, I think the biggest thing to remember is that you're not the CEO's friend, that you're not there to be a buddy. You're there to actually ask probing questions. And to rub their nose in the consequences of what could go wrong. But one of the things I've also learned is that on a board, even when you own the entire company, you can't dictate what they need to do. You can only guide and you can set guide rails. And so at the end of the day, you're ultimately deciding, is this the right person to run the business or not? That's the key question. You're also thinking about incentives. How do I align this person with the outcome that I want? And ensuring that they're totally aligned with your goals. And other than that, like you could see one of the things that's been interesting to me, and I've been on venture boards, I've been on private equity backboards, and then the boards of our own companies. And I've seen this over and over again, where I've experienced something and I see the CEO making the same mistake and I try and tell them, and I've found that generally the CEO needs to actually go take the fork and Stick it into the electrical socket and realize that he gets zapped, which is unfortunate and infuriating because you're sitting there like a slow motion train wreck saying, oh my God, he's making this mistake. I don't want him to do this. It's going to ruin the company…

AI assessment note: “the biggest thing to remember is that you're not the CEO's friend”

Q do I focus on my strengths and just get better at them? I often hear, hey, just focus on your strengths and be world class. Or someone said to me the other day, no, people arrogantly think that competitors killed you through your weaknesses. How do you think about that, and how would you advise me in terms of doubling down on strengths versus really coming back and nailing weaknesses?

A We always say every CEO has a superpower, right? I don't know if you know the saying to a person with a hammer, everything looks like a nail. And I'd say each of us as a CEO or a leader or an investor or whatever has a lens through which they view the world. And we say, you know, generally it's product, sales, marketing, finance, or operations. And they're basically looking at it and going, well, product is the secret to everything, or marketing is the secret to everything, or Sales or whatever. What I've found, you know, I'm generally a product person. That's how I started when I was building my companies. I was the guy who would always say, well, we'll do better once we launch this feature. We'll do better once we redesign the marketing site and make it look prettier. And that's where I kind of default to. And fortunately, product often is the key thing. If you have a really shitty bakery, that's ugly as hell and located in a bad location, but you have the best cinnamon buns in the city. People will probably line up and go there. But what I've learned over time is that I understand enough about marketing and sales to know what the right incentives and the right people to do those things are. And I've seen the results that can come from it. So what I'd say is you want to double down on your strength, but then you also want to be able to identify and know enough to know what th…

AI assessment note: “you want to double down on your strength, but then you also want to”

Q Yeah, absolutely. They can, which is absolutely why my question on price I was so interested by. I'm also interested because I've read a lot of your writing and as we were chatting about before the show, listen to many of your podcast episodes before, and you've said before on paper, I'm a terrible CEO. So why is that?

A Well, I think like a lot of founders, I'm very urgent and I love Doing things quickly. I love ideas. I love strategy. What I don't really like is implementation and follow through and managing people. And what I've realized is that I'm very good at laser focusing for a short period of time on one company, deal, idea, strategy, whatever it is, but I don't enjoy spending the next 60 days implementing a plan and building that plan. To be honest, yes, I can run a company. I've done it. I did it for 10 plus years, and I was very successful at it, but I find one company, for me at least, isn't enough. I wanted more diversification of thought. I wanted to be able to jump into different ideas and different types of businesses, and I realized I just love business. I'm like an inch deep and a mile wide, and so it really suits me well to invest because it allows me to be on a High board level and interact with all the CEOs and understand all their businesses and help them grow them. But at the end of the day, I'm not managing people. I'm not overseeing implementation of ideas. And at the end of the day, there's people who love doing that. And I love to just step out of their way and let them do it because I would just not be happy doing it. I didn't enjoy being a CEO and running a large company. I like running a five person company or a

AI assessment note: “What I don't really like is implementation and follow through and managing people.”

Q Not at all, but I would love to kick off with a little on you. So tell me, how did you make your way into the wonderful world of tech and startups? And what was that founding moment for you with Tiny in a very succinct three to four minutes?

A Yeah, I've really had three careers. So accidental entrepreneur, CEO and operator, and then now investor. Basically, when I was in high school, I started a tech news site, and it just totally took off, and so I started getting hundreds of thousands of visits to this site. I started writing news. I hired a team of writers. I started selling ads and negotiating ad deals, and so I basically got my MBA in high school running this website and pretty much skipped all of high school, and so through that, I got to interview Steve Jobs. I got to Travel all over the world and have all these incredible experiences, but at the end of it, I was kind of left not sure what to do. What I ended up doing when I graduated high school is I decided to move to Silicon Valley. I really wanted to go work at Apple or Google and learn how a big company was run, but I didn't have a ton of money, and I decided that I would start freelancing to make some extra money, and one really great insight I had was that If I pretended to be an agency, I could probably win more work. And so I came up with the name metal lab. I designed a very, very slick looking site that made me look like a big agency. And I started using the sales skills that I learned running this website. And I called up founders of Silicon Valley companies that had raised money. I'd go on tech crunch and see that someone had done a raise and I'd…

AI assessment note: “when I was in high school, I started a tech news site”

Q do I focus on my strengths and just get better at them? I often hear, hey, just focus on your strengths and be world class. Or someone said to me the other day, no, people arrogantly think that competitors killed you through your weaknesses. How do you think about that, and how would you advise me in terms of doubling down on strengths versus really coming back and nailing weaknesses?

A We always say every CEO has a superpower, right? I don't know if you know the saying to a person with a hammer, everything looks like a nail. And I'd say each of us as a CEO or a leader or an investor or whatever has a lens through which they view the world. And we say, you know, generally it's product, sales, marketing, finance, or operations. And they're basically looking at it and going, well, product is the secret to everything, or marketing is the secret to everything, or Sales or whatever. What I've found, you know, I'm generally a product person. That's how I started when I was building my companies. I was the guy who would always say, well, we'll do better once we launch this feature. We'll do better once we redesign the marketing site and make it look prettier. And that's where I kind of default to. And fortunately, product often is the key thing. If you have a really shitty bakery, that's ugly as hell and located in a bad location, but you have the best cinnamon buns in the city. People will probably line up and go there. But what I've learned over time is that I understand enough about marketing and sales to know what the right incentives and the right people to do those things are. And I've seen the results that can come from it. So what I'd say is you want to double down on your strength, but then you also want to be able to identify and know enough to know what th…

AI assessment note: “you want to double down on your strength, but then you also want to be able”