E245: From $0 to Billions in a Regulated Market

How do you build a multibillion-dollar company from scratch, walk away at the peak, and reinvent your life around purpose, generosity, and impact? In this episode, I talk with Pete Kadens, one of America’s most respected first-generation wealth creators and one of the leading philanthropists focused on closing education and opportunity gaps across the U. S. Today. Pete and I dive into how he built Green Thumb Industries (GTI) into a multibillion-dollar cannabis company, the unsexy strategies that made it work, and why choosing overlooked markets and consumers unlocked massive profit. We cover the power of ownership cultures, transparency, discipline frameworks, and why giving equity and education to employees creates extraordinary performance. We also explore the character transformation that led him to retire at 40.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00David Weisburd?

  So Pete, you're a first generation wealth creator, you're co-founder and CEO of Green Thumb, which you built from scratch, took it to $6 billion market cap. Today it's roughly $2 billion.

• 0:11David Weisburd?

  Tell me about founding Green Thumb Industries. Specifically, how did you build a business in the cutthroat cannabis space?

• 0:19Speaker 01

  Yeah, so I had a couple tours of duty as an entrepreneur. I started my first business at 24 and sold it at 29, was a millionaire before 30, and then had started another business in the commercial solar space and had another nice exit. And I was working, running a billion-dollar subsidiary of a utility, the same utility I had sold my solar company to. And I got a phone call one day from a friend, we weren't that friendly, but someone I knew in Chicago, and he just asked me, he said, "What do you think about weed?" And I said, "I love weed." And he said, "No, I'm not talking about the product. I'm talking about the business of weed."

• 1:01Speaker 01

  You know, it's starting to be legalized. And there's all these folks out in Colorado who are, you know, building $100 million-plus businesses who don't really even know what they're doing. Like, what if really sophisticated operators came into the space like you and I? And so I started doing some, you know, private equity-type due diligence on the current operators in the space with my partner and other people, and learned a lot about the space. And I figured out is that, yeah, indeed, there's a massive opportunity to do something really, really different in the space. And that's exactly what we did. The Green Thumb Industries is the largest cannabis company in the world today. Revenue-wise, we'll do, I think, $1.4 billion, $1.5 billion in

• 1:42Speaker 01

  revenue this year, operations in 15 states around the US. And, you know, we built this thing by just doing the unsexy things well. While everyone else was trying to be the Apple Store of weed, or the Starbucks of weed... We were just busy doing the blocking and tackling. Good example, David, we're, the company is headquartered in downtown Chicago. And we don't even have a dispensary. You're the largest cannabis company in the world. We don't even have a dispensary in our whole town. The reason is, is that the company is operated on the basis of profit. You know, profit above all else, basically, except for ethics and morality. And we do the unsexy things well. So instead of being in Chicago, we're in Joliet, Naperville, and Essingham, and on the line.

• 2:25Speaker 01

  Other cities that some people may not have even heard of that are, you know, 30,000, 50,000, 100,000 people cities in Illinois. And that's just a good example. It's like that all over the country. We sort of zigged while everyone else was zagging. And I think that's why we were able to take this thing to, you know, sort of to the moon, so to speak.

• 2:45David Weisburd?

  Tell me about what's unsexy about Greentown.

• 2:48Speaker 01

  Yeah, so being in Toledo, Ohio versus Cleveland or Columbus. Or being in Erie, Pennsylvania versus Pittsburgh and Philadelphia. That's pretty unsexy. But when you look at the math, you know, Erie, Pennsylvania is a great example. We, we got the first, we got the highest score in the state of Pennsylvania. We could have picked anywhere we wanted to go. We picked Erie, which again, not sexy, but when you look at the NSA there, it's about 500,000 people. And the way the state had chopped up the licenses, the next closest dispensary was going to be like 72 miles away in Bradford, Pennsylvania. Now, I don't know if anyone here has been to Erie, but if you have, you know that for about six months a year, you ain't going anywhere.

• 3:33Speaker 01

  Like you're not driving 70 miles to get, you know, pre-rolled joints that are $10 cheaper because the weather is very inclement. We went to places that no one else would go because our bias was we want a monopoly or oligopoly on a market. And that's why our margins are some of the highest in the world, in the industry, and certainly our profits. We are the most profitable company in the, in the world. And I'm saying we, I've been gone for, you know, five and a half years, but, um, you know, I still feel very much a part of it, obviously. The other thing is a lot of times people don't go after non-obvious opportunities. We got really good at going after non-obvious opportunities. So let me give you an example. In 2013, 14, when we started this thing.

• 4:13Speaker 01

  You know, the average marijuana consumer in that time was sort of like a 32 year old man who had been, you know, smoking weed since college. The consumer was not the American woman, mother of three kids aged 30 to 50. But what we know to be true, what we knew to be true then, and what we still know to be true is that we went after the, uh, the, the customer that was not yet the customer. And pull them over from that glass of wine at the end of the night after raising three toddlers to a gummy, uh, that that would unlock so much opportunity because the truth is, is that uh, American women, um, age 30 to 50 drive more consumer behavior than any other demographic in the world. Uh, I, you know, when my wife tells me we're going somewhere, we're going somewhere, you know? I think we all sort of feel that or acknowledge that.

• 4:57Speaker 01

  So, um, instead of going to where the market was, it's sort of like the Wayne Gretzky. You know, we weren't skating to where the puck was. We were skating to where the puck was going. That was just something that we did better than anybody else. And it was pretty unsexy at the time. And frankly, a lot of people even thought it was a little questionable at the time. We, we directed all of our products, all of our form factors, many of our taste profiles towards the female consumer and then ended up working out very well, obviously.

• 5:22David Weisburd?

  It's well-known meme or idea that if you want to make a lot of money, you go after unsexy businesses. You go after waste, waste management or construction, things like that. I think it's much more difficult to implement it. Why? Because while you're building these unsexy businesses, you have, you're living in the real world. When you go to cocktail parties, people ask you where your dispensaries are. You say Erie, Pennsylvania versus downtown Chicago. So how did you have the discipline to stick to an unsexy strategies? And what are some lessons from that?

• 5:55Speaker 01

  My partner, um, in, in, in the green thumb industries was very, very operationally disciplined. He still is to this day, probably the most disciplined operator in the space. His name is Ben Kovaler. He taught me a lot frankly about operational discipline. And you know, when you have a partner, you know, Ben and I didn't always see eye to eye. But I think we respected one another because we each brought very complementary skills to the table. When I got out of line or was doing something that maybe didn't map to our, to our vision or to our discipline, he sort of course corrected me. And similarly, sometimes when he was too sort of focused on the books and on the spreadsheets and not thinking about the big vision, I was able to hold him accountable and challenge him.

• 6:40Speaker 01

  And so I do think that if you're in a, if you're in a good complementary partnership, you can sort of stay the course and stay disciplined. And, and you know, it's good if, you know, I think we've learned as a school of entrepreneurship, EOS, the Entrepreneurial Operating System. And you know, typically there's got to be one visionary and one integrator and a great partnership. And we had the visionary integrator balance going quite well. Ben has become the visionary of the business and now there's another integrator in there named Anthony Georgidas with him. And you know, it's just that, that partnership balance where you can hold each other accountable. I think is the way we did it. And again, when the North Star is we want to be the most profitable company in the space,

• 7:22Speaker 01

  you sort of set aside some of the more undisciplined approaches that don't make you money. And that was always our initiative. It's like, we want to, we want to sell to the mass market and we want to, you know, brands distributed at scale. And we want to be the most profitable company in the cannabis world. And so we just held true to that vision.

• 7:43David Weisburd?

  Perhaps what I'm getting to is you're also homo sapien like other people. Nobody does not want to make profits. You're limited to the same neurobiology that humans are limited to. How do you discipline your way into doing things that in the short term are not sexy? And what are some to do's in order to replicate the strategy?

• 8:06Speaker 01

  I'm a big believer in manifestation and building roadmaps. And you know, our roadmaps, my personal roadmap was always about reaching some level of attainable wealth. And, and you know, so I knew the specific destination and just like that, my companies have always known the specific destination that they wanted to get to. And then from there, you build sort of a disciplines framework to be able to get there. And, and, and then you hire really, really talented people to operate within that discipline framework. But, but the key is, I think, is you have the discipline framework to get to your North Star. And you let really talented people operate freely within that discipline framework. What we did at Green Tham is similar to what I'm doing now with my current companies, which is like, we give people a lot of autonomy.

• 8:50Speaker 01

  We say to people like, we trust you and therefore like you're sort of the CEO of your own domain. You sort of blow up the hierarchy, so to speak. And when you blow up the hierarchy and you give people agency and autonomy, magic happens. And you know, but again, it has to be done with a discipline framework. There were steps to get to our North Star. I'm, I'm a big believer in Jack Stack, uh, his approach. He wrote a book called The Great Game of Business, right? And, and he talks about, um, one of the best ways to keep everybody in the company on course and mission aligned and goal aligned is through full transparency. In fact, I will say like, I own a engineering company. We have about a hundred employees. The company is headquartered out of Philadelphia. I bought the company a couple of years ago and it was remarkable.

• 9:33Speaker 01

  When I first bought the company, we asked the employees, not me, but you know, we sort of did a survey, an anonymous survey. And we asked the employees, like, what are the most important things to you about working at this company? Uh, it's called mainstay. And, and we, and then we took all the responses and we built a word cloud. And it in, in the word cloud, right in the middle, in like 48 point font, where the next closest word was like 16 point font, was the word transparency. And I think, just like Jack Stack did in The Great Game of Business in Springfield, Missouri, like you just tell people what's happening, where they're at, where we're at as a company, and what we need to do to get to our North Star. If you walk through Green Thumb Ministries, there's a big whiteboard right in the middle,

• 10:14Speaker 01

  the headquarters, and it had the 10 KPIs that we had to achieve, and it measured them week by week. So, everybody knew the level of accountability and the standards we had to meet in order to meet our vision and North Star. So, that's sort of how we did it. I've adopted that strategy with all the companies I've ever managed.

• 10:29David Weisburd?

  That's an old school book. I just was looking it up. It was written in 1992. I think I read it in probably the late 90s. I used to go to bookstores and read business books in high school. Jack Stack talks about this ESOPs, which is Employee-Owned Organization. Is equity one of the secret sauces to making people do these unsexy tasks?

• 10:53Speaker 01

  Absolutely. A lot of people became millionaires at Green Thumb Ministry, not just the executive team, far downstream from the executive team. And at all of my companies, I have provided equity. I own a company now called Warmer, warmer.com. It's in the peer-to-peer support space, and every single employee at the company, it's only 20 of us, but every single employee at the company is an owner of the company. That's sort of a mandate, because you want people to act like owners. You better make them owners, in my opinion. And we want everybody acting like an owner. We want everyone at our company to pass the trash test, which is, you see a piece of trash on the ground at the office. Don't let the person, don't rely on the person who actually threw their

• 11:37Speaker 01

  trash on the ground to pick it up. Just pick it up yourself. You're an owner, right? And so, every company I've ever managed, everyone meets the trash test. And that's sort of a cultural norm at these companies. But you've got to take it a step further. And Jack Stack talks about this in his book, and you're right, he was very early on to this. KKR, the private equity firm, has now adopted this in many ways, and they've found that the companies where the ESOP, there's an employee stock ownership plan, the EBITDA is 3X what it was 10 years ago when they didn't have an ESOP plan, for example. And so, but you can't just, here's what I would say. This is what's interesting, is, and if there's, maybe there's one thing that employers take away from this call, maybe

• 12:22Speaker 01

  it's this, which is that Employees don't feel ownership based upon what you give them. They feel ownership in the company based upon what they give you. And so they have to feel like they're giving value to the company. They have to feel like they understand the financials so they can add value to the financials. Even the janitor, you know, as Jack Stack talks about in The Great Game of Business, understood the financial implications of wasting disinfectant, right? Cost of goods sold up, inventory down. Like, and, and he understood the balance sheet implications for that. And so it's great to have owners, but it's even better and more effective to have educated owners who understand the implications of the work they're doing. And that's what I've tried to do in all my businesses.

• 13:06David Weisburd?

  I was essentially asking you the question of, how do you build an organization where people are not going towards the flashy lights and the flashing headlines and the cool things you could tell their friends? And your answer was you build a much bigger purpose, which is we're building something, we're self-actualizing ourselves through the business. We get ownership over domains. We're all a part of this bigger mission. And we could also, you know, build, build wealth for ourselves and our families, which matters much more than telling some random person at a cocktail party, I have a dispensary in Chicago versus Erie. You just have a bigger why. So it's not that they're avoiding this other kind of cool, nice to have. It's that you're giving them something much more valuable.

• 13:52Speaker 01

  No question, no question. And, you know, like, I gotta say, I, I operate on sort of a sleep at night quotient. You know, like if I'm not sleeping at night, something's wrong. And, and something's bothering me and I need to figure out what that is. Cause I just wanna be able to feel good enough about myself and my decisions. And I sleep at night. And I gotta tell you, as I sit here in my beautiful home on Lake Michigan, which I earned, I worked hard for.

• 14:18Speaker 01

  I feel I can sleep so much better at night knowing that I didn't hoard all the the benefits. You know, yeah, I I benefited and I live in this big, beautiful home and I have a I have the type of life where I can do just about anything I want. But it wasn't just me. There are lots of people whose lives were altered in a in a really meaningful way and generational wealth was created. And I just sleep better at night knowing that I'm not selfish, I'm not greedy, I have a moral imperative to look out for others. And I I know we might touch on this later, David, but maybe it's a good time to say it is like I have always said, and when I speak in almost every podcast I do. I tell people the more generous I am, the wealthier I get.

• 15:02Speaker 01

  And that's not just about money and that's not just about equity. There's lots of forms of generosity. You can be generous with your energy, your intellect, your network.

• 15:12Speaker 01

  But I just feel like I I am a little spiritual in the sense that, you know, when I give to the universe, the universe repays me. And and I just believe that, you know, those of us who are very greedy, only looking out for ourselves and our own wealth and never share any of it. I question sort of the moral imperative there, you know, and and also the true fulfillment. I'm very fulfilled that lots of other people have benefited from my work.

• 15:35David Weisburd?

  Let's take away the morality of the equation from a purely rational standpoint. Give me an example of by not being greedy, by by being giving out the margins, how are you able to benefit? How are you able to scale that as well?

• 15:50Speaker 01

  The more people around me feel like owners, the more they feel like they can give and contribute. They're more committed they're going to be. And, you know, if you want to have build a successful company, you have to have committed people working on your team. And so I I think that, but instead of forcing commitment, it's better to sort of earn it through kind and generous gestures. And, you know, David. I don't really, to be honest with you, I don't really decouple my moral imperatives from making money, you know? I know you asked me to do that, but I don't do that. I always tell people, I do not love my businesses. I love my family. I love myself. I do not love my businesses. I see my businesses as a vehicle to help people and to help myself grow and learn and build wealth.

• 16:35Speaker 01

  And so I try my best not to decouple those things. And while I've had my moments where sort of my moral imperative may have been, you know, diminished a little bit while I made some hard or even ruthless decisions, I try to make sure that I invoke the moral imperative in every decision I make. Because the truth is, is like, you just get better results. When people like working for you, when people feel comfort, when people feel they can give a lot and be rewarded a lot, you build better companies. And I've done that a number of times now, and it continues to work for me. I always tell people, like, the culture I build of the companies that I've founded, it's all about a culture of compliments. I want people liking working together with their peers and complimenting one another and supporting one another.

• 17:16Speaker 01

  It's just a much more fun, much more advantaged way to play the game. I think it's a unique advantage, a distinct advantage in the corporate world today.

• 17:24David Weisburd?

  A lot of people fail to say, see that one of the main benefits or main structures and startups that make so many successful is the equity, is this alignment. It's not, they think it's a tech thing. It's not a tech thing, it's an alignment thing. I think a lot of places outside of specific use, like edge cases, like a McDonald's or franchises with existing built systems, I think a lot more places would have a lot more upside if there was more sharing and more alignment.

• 17:53Speaker 01

  Literally, KKR, the big private equity firm, has published their data on the companies where every single employee is an owner of the company. And just like, benchmark those companies. There's an overhead door company based in southern Illinois, I forget the town, that KKR owns. And like, benchmark that company since they gave all the employees ownership versus its biggest competitors. And again, they're like 3X outperforming their biggest competitors. And, you know, before KKR did this, they were sort of like performing on par with their competitors. So it's like, the proof is in the pudding, the data supports that when people are aligned through ownership and opportunity, they perform.

• 18:33Speaker 01

  The exact report is called Creating an Ownership Culture by KKR. So I'll take a look. The data is very suggestive and supportive of what I'm saying. So think about, you know, providing ownership to your employees and also again, educating them. Now just give ownership, educate them on what the financials mean, how to read a balance sheet, how to read a cash flow statement. That's really important.

• 18:54David Weisburd?

  You've been on 60 Minutes twice. I recently took a look at that and one of the things that talks about is your character arc, going from this ruthless business person to one of the top philanthropists in the US. Tell me about this character arc and what were your lessons along the way that changed essentially your character?

• 19:14Speaker 01

  I've always had a bias to action and I've always been charitably inclined, but you know, certainly there have been moments in my life where I was so focused on a business that I didn't feel I had the time to contribute to other causes outside of the, you know, my, my area of focus. I'm teaching a class at the collegiate level now called Mastering Wealth and I remind my students that, um, you know, when you think about someone who's wealthy, I know that you traditionally think about, you know, bank account wealth. But, you know, I, I spent a lot of time, I didn't then, but I spent a lot of time now thinking about the different permutations of wealth, health wealth, relationship wealth,

• 19:57Speaker 01

  family wealth, you know, network wealth, lots of different forms of wealth. And, you know, what happened, to be honest with you, David, is when I, when I reached my wealth goal, I'm a big manifestor, you know, a long time ago and I read Think and Grow Rich by Napoleon Hill and I set my wealth objectives and I did accomplish them and then some. And when I got to my wealth goal, I think I felt this sense of relief, but also this extraordinary sense of juxtaposition. Like, yeah, I'm bank account rich, but holy cow, do I feel really relationship poor. And, um, and I, I felt like I needed to do something about it. Ultimately that led to my, to my retirement.

• 20:39Speaker 01

  The other thing I'll say is this, like, if you made money the way I made money. Which is at the time, rich white man. I didn't grow up rich, but I came over my history of my entrepreneurial career, I became very wealthy. But you know, if you became rich the way I did, which is by selling marijuana, you can't look yourself in the mirror and and not acknowledge that you did this on the backs of black and brown folk who've been selling weed in their basements and garages for like four decades. And instead of creating a fortune, they created a criminal record for themselves. And and so I became, there was a lot of guilt. I've said that on 60 Minutes Live with Scott Pelley. A lot of guilt in in the sense that I really needed to pay it back.

• 21:23Speaker 01

  Like, who were the people and communities who suffered and sacrificed so that I could succeed? And when I woke up on this day with extraordinary wealth in my bank account, I felt a degree of guilt and I felt some sort of this relief of this hubris. And I said, I gotta go pay it backward to the people and communities who suffered for me to be able to to to actually actualize this. And that's how this happened. And it was just sort of a moment of real human clarity. And and I think I've I've really, I've become such a better human, much less ruthless, much more kind, much more empowering to people around me. And and the last thing I'll say is, um,

• 22:04Speaker 01

  you know, I used to give a shit about what I call extrinsic affirmation. I don't need extrinsic affirmation. I know the man I am. And so I to to to have the ability to stop caring about how other people see you or what they think about you and just do the things that make you fulfilled and feel good. And to live that as your life purpose, like my life purpose is to help myself and people around me who I care for, find the truest form of fulfillment.

• 22:28Speaker 01

  And so I I think the way I do that is through charitable endeavors. And I feel very happy and proud of what we've done. And I'm never ruthless anymore, which is which is good.

• 22:38David Weisburd?

  There's this nevallism that there's two ways to reach this this type of enlightenment. One is to be a monk and the other is to attain your goals and realize that you're good enough or you no longer need them. Would you have reached this kind of level of thinking and enlightenment if you hadn't achieved your goals? And isn't that a big part of why you're able to kind of do good and do these things today?

• 23:02Speaker 01

  I'd love to say that no, I didn't need to achieve my goals in order to sort of get to this point of enlightenment. By the way, I often call it enlightened self-interest because I do believe I achieved some enlightenment, but I believe that some of it is still self-interested and I'm okay with that. I wish I could say yes, but the truth is, is that I don't think I would have gotten to this place had I not achieved my business and financial goals. That gave me a sense of security and safety and comfort that allowed me to sort of flourish in other domains. I do think I'm a good human. I do think I care about the world, but I care about the world a ton more because I achieved my business objectives. Now, if I was giving advice to

• 23:45Speaker 01

  somebody else, I'd say probably not the most ideal way to do it. You could find, you could sort of stay committed to your more well-rounded objectives and be a thoughtful and charitable leader in your community outside of your business, even before you hit it big. But that's unfortunately not what happened with me. But I don't have any regrets, but the truth is, is that I had to hit my goals before I could sort of open up and become really enlightened.

• 24:10David Weisburd?

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• 24:55David Weisburd?

  I have a very heretical belief on this. So, one of my masters in psychology, and one of the things that I believe that almost nobody in psychology believes is that almost any disorder that people have is non-binary. Depression, I think everybody has trauma, all sorts of things. A very unusual belief that I have is that everybody has a form of multiple personality disorder. What does that mean?

• 25:21David Weisburd?

  Today it's called dissociative identity disorder. That's, that's, that's a new way people want, want it to be called. But we all have different drives within ourselves, which is oftentimes a time for conflict. Last time we chatted, we talked about your drive to succeed versus your drive to be with your kids. These are essentially different drives in ourselves. And if you subscribe to that, something like achieving your wealth can quell or satisfy that need. So you had this tough upbringing. You had this need to show people that, that you mattered and that you were good enough. Once that is satisfied, it kind of relaxes and allows you to kind of evolve yourself into a better human being. What are your thoughts on this?

• 26:06Speaker 01

  I couldn't agree more. I mean, I've never actually heard it described in, in that accurate of a way. And again, I wish it wasn't that, that, I wish that wasn't the case. It's at least not for me, but, but the truth is, is that, you know, sort of like, sort of like we, we have multiple personalities. You know, as we're talking about, we, there's, there's, there's, it's not just polar personalities. It's sort of, there's a lot of polarity in, in business success. And I, in this class I teach at the collegiate level, I was just reminding my students this week, like, you gotta sort of like, in order to be a really successful entrepreneur, you sort of have to smooth, you have to smooth out the edges. You have to become really emotionally stable and you have to strike some form of balance.

• 26:50Speaker 01

  I actually think that's a really overused word, a balance, but, because it's very, very hard to achieve that.

• 26:56David Weisburd?

  Yeah, what? Work-life balance.

• 26:58Speaker 01

  Yeah, right. That, that's a hard one to achieve, but I gotta tell you, like, for me, it's, it's a lot about understanding polarity and acknowledging polarity and then trying to figure out like how to, you know, bring things a little bit closer together versus, you know, versus sort of to accentuate the polarity. I'll give you an example. It feels like in many cases, it's bank account wealth up, health wealth down. You know, bank account wealth up, relationship wealth down. You know, bank account wealth up, happiness wealth down, like. It doesn't have to be that way. Maybe for a period of time it does, you know, while you're really struggling or whatnot, but like, I definitely felt that polarity and it was hard for me to manage.

• 27:42Speaker 01

  But I mean, look, the truth is, is like, I was built, I was part of building a rocket ship from zero to a billion in revenue in a very short period of time. Like, you're going to be on a plane 200 nights a year? Like, how are you going to have family wealth and relationship wealth if you're flying around the country 200 nights a year? It's very, very hard to do. Maybe I'm not dynamic enough to manage that, but that's where my struggle was. In fact, that's why I retired at the age of 40s. I just couldn't, I didn't like the polarity anymore and I couldn't manage it. I needed to sort of get back in balance.

• 28:14David Weisburd?

  It's so interesting because the reason we're talking in many ways is because you are so one-sided because you had this extreme success because of the trade-offs that you made. Somewhat of a paradox is that oftentimes these stories are told from the side of somebody that has extreme lack of work-life balance and is able to do those things. At the same time, it is necessary. So if you think about any new industry, including cannabis, it was kind of the Wild West. There was going to be a winner and many of these games, for better or for worse, are zero-sum or have a lot of oligopolic-type tendencies. So you have to have this kind of lack of balance. One of the things that was really interesting is when we were chatting, preparing for this interview, you said that even though you didn't see your kids for the first couple of years, you did not regret that. Tell me about that.

• 29:00Speaker 01

  I'm not sure I want them to hear that, but so, but you know, as I look back on my life, when I was on this run, my kids were sort of ages like, you know, one to six, right? My oldest is in high school and so I don't have regrets. Maybe I could have done it differently. I certainly could have been a more compassionate husband and father. I really would, I really would have liked to have anchored around compassion. That would have been a better way to, you know, to operate. I didn't have a lot of that either for my wife, who was basically re-raising, you know, three toddlers at the time.

• 29:42Speaker 01

  But the reason I don't have regrets is because my push, my sacrifice, gave me an opportunity to be around, to retire at the age of 40 and to be around basically every day. From the time when I was 40, my oldest was, I guess, nine.

• 29:59Speaker 01

  Um, and for the, from nine years old and that I'm at a seven year old and a five year old when I retired. So like it really early ages, formative developmental ages, I was able to like quit and be around. I was totally around and engaged during COVID. Uh, we went and spent, you know, six months in Florida and had the best time. Like I didn't have to do anything, you know? Um, I didn't have to be at any meetings. I had the ultimate flexibility. My family and I could travel and experience. And I just feel like, you know, would I have been be able to take my kids to Spain or Italy or Costa Rica or Panama? All these places they have been able to see and go to. If I hadn't sort of pushed the envelope when they were younger? No, I wouldn't. And so I look back and while like I probably

• 30:43Speaker 01

  would have changed some things, I can't regret it because it's opened up so many doors and opportunities for me to foster better relationships with my kids and my spouse and others around me. Um, uh, over the last couple of years. And that's, I don't know if I would have been able to do it otherwise. And I still have lots of friends who I think my best friend here in Chicago and, you know, he does very well for himself, but he's in investment banking and he's still traveling like three to four days a week. And he's got four kids and that is really hard. Um, so I'm, I, I have no regrets, even though it pains me to say that in some way.

• 31:14David Weisburd?

  It's a heavy subject. I appreciate you going down this rabbit hole. I'm thinking as a future father, I recently got married. We want to have.

• 31:22Speaker 01

  Congrats.

• 31:23David Weisburd?

  Thank you. Thank you. It was a beautiful wedding. And what do I want to role model to my kids as a father? Because I do think the roles of a father or mother are slightly different. And as a father, what do you think going through this process? What is it that you believe that your role is? And what do you want your kids to remember or model from you?

• 31:45Speaker 01

  It's a great question. Fun question for me to answer because I spent a lot of time, spent a lot of time thinking about it. I want my kids to know and see my best and authentic self. You know, like if, if, if you have the time and capacity to bring your best self to your kids, it's amazing how they see you. Got a piece of advice from my friend, Amber Vans Box, who runs a multi-billion dollar company called LTK out of Dallas. And she's a fellow of mine at the Aspen Institute. Once she said something to me that stuck with me and I don't think I'll ever forget it. She said, Pete, she said, you're spending a lot of time being your kid's roommate. Maybe you should spend more time being their playmate. I was like, holy shit, like, I couldn't have said it better myself. I come home at the end of the day, I'm tired as hell.

• 32:31Speaker 01

  You know, we have dinner, we go through the motions, we go over homework and then I put them to bed. And it's like, that's not quality time. And so when your kid asks you to play basketball or play football or watch a movie with them or play a video game or whatever it is, like, just say yes, just do it. You know, be their playmate. That's the type of stuff they're gonna remember. That's the legacy that counts for them. They don't give a shit about how much money I made. Maybe later in life they will, but like, right now, they certainly don't care. They just want their dad and they want their dad to be present and they want their dad to be fun. And, and I've really endeavored to do that. And the other thing, though, is like, look, I want my kids to know that we do important work in this family. Like, we have a moral imperative. We have a moral north star. We believe in our family that a rising tide lifts all boats.

• 33:15Speaker 01

  Like, in other words, you know, the better people are doing in the South Side of Chicago and the under-resourced underestimated communities, the better we're doing here up in the beautiful northern suburbs that are very wealthy, like, we're all in this game together. And I think we've been able to show our kids, especially in the last five, six years, my wife and I have been able to show our kids, like, we invest deeply in communities that are trauma-filled because we believe that when they're better, we're better too. And our kids see that and they live that, experience that. And, and I think that's the legacy that I want my kids to have for me is that my dad pushed the envelope, believed in helping others, went out of his way to help others. And, you know, like, the other thing, I'll just say one last thing on this, David, because this is an area of real passion for me. I tell my kids all the time, my kids have never sat down at a restaurant.

• 34:00Speaker 01

  I own two restaurants myself, but I'm talking about outside of my restaurants. Like, they have never sat down at a restaurant with me where I didn't look the server in the eye and say, excuse me, may I have your name? Never. My kids have never seen that like I there's never been a scenario where that hasn't happened. And and I explained to them that, you know, Dale Carnegie, How to Win Friends and Influence People, the sweetest sound in the English language is your own name. And we're going to treat this person like they're an equal.

• 34:27Speaker 01

  And and I say to my kids all the time, I am going to be judged and so are you by the way we treat people who can do absolutely nothing for us. And I really hope that is my legacy. And I hope my kids own that legacy too. Like, we're just going to treat people who can do nothing for us with kindness and dignity and grace. And if we all do that, not just me and my family, the world's going to be a lot better of a place.

• 34:48David Weisburd?

  You have a lot of parents. They say, you know, well, my kid's this, he's spoiled and rotten, and they don't think about their own behavior. Like, what behavior are you modeling for your kids? Because chances are, it's going to be very similar.

• 35:01Speaker 01

  Even like, I I I tell the teachers and the parents and principals of my kids, different schools or not, like, I my kid doesn't need to be valet d'entourant. My kid doesn't need to be the best athlete. My kid doesn't need to be, you know, the most popular. We we don't strive for those things for our children. But you know what we want our kids to be? We want our kids to be the nicest. We want our kids to be the kindest. And, you know, just to be super honest, like, when you're when you're the rich kid in school, now, there's plenty of rich people on the North Shore of Chicago, but people know we're we're, you know, meaningfully wealthy and, you know, my kids have caught some heat over that for the years, especially in the ways that I made my wealth in the cannabis sector. That's been a, you know, sort of a running joke for a number of years with, you know, teenagers. But, um, you know what?

• 35:45Speaker 01

  I've never, the thing I'm most proud of about my kids has nothing to do with their grades or athletic accomplishments. And my oldest is now fifteen. In fifteen years of being a parent, never once have I gotten a call from another parent, a teacher, a principal, saying that my kid was a bully, my kid was mean, my kid was disrespectful to somebody else. Because that's what we prioritize. We set the bar in our home that we are going to be kind, generous humans. And and that is the non like, that is, there's nothing else that's acceptable other than other than that. Uh, and so it's just about setting priorities and what matters, what matter. I don't give a shit if my kids go to a tier three college, to be honest with you, they're going to be just fine.

• 36:26Speaker 01

  Uh, but learning how to be nice and kind and generous to the world, like, that's something that they can't they can't not have.

• 36:32David Weisburd?

  Do you just assume kind of the assertiveness and the strength? And how do you not overdo it? How do you make sure your kids aren't soft?

• 36:40Speaker 01

  We hold them accountable to standards. Most importantly, the number one way you can ensure your kids won't be soft is by showing them how hard you work. You know, like, there's a reason, you know, I didn't want to go, I, I, I got the flu shot yesterday and, and I don't feel great. I really, I'm kind of a little off today if I'm being honest. But you know what? I was still the first person out the door at 5:45 a.m. on the way to the gym this morning to meet my trainer to bust my ass. And I do that every morning. And I run Spartan races and I, my kids see me putting the work in. And when your kids see you putting the work in and believing in yourself and giving of yourself and striving for better for yourself, like, they follow that

• 37:21Speaker 01

  lead, you know? And so in our home, you know, the mom and dad in this home, they just work really damn hard and they lead by example. And that's how we do it. And our kids have in many ways followed our lead. Our kids are very, very disciplined, which we're happy about.

• 37:35David Weisburd?

  There's certain things that almost has to be seen on a regular basis, like discipline, commitment, these unsexy things. You'll never see them on a viral tweet or viral short, but it's like this consistency that's so important to model, that's so valuable to understand. Like what it really takes to succeed is something that most people don't actually understand.

• 37:54Speaker 01

  And you know what? They may not understand it today, but upon reflection, when they're like in their twenties and out of college.

• 38:00David Weisburd?

  Your kids will understand it. Most people, most people's kids will not because they think it's about, they, a lot of people think success is about doing the spectacular triple axel, you know, at the Olympics every four years. They fail to see the thousands of triple axels to do that one triple axel. And also, most things are not the Olympics with a single race every four years. So I think a lot of people miss what it, what it really takes to succeed.

• 38:24Speaker 01

  We have a little bit of a idiom in our house that we say, we say that how you do anything is how you do everything. So you always show up. I don't give a shit if the homework assignment isn't worth many points. I don't care if you don't like it. Like you, you, you strive to do everything you do well. And that's a hard concept for a kid to, for a kid to understand. But when again, you know, I'm gonna be washing dishes. I'm gonna do it well in my hole there. I can't see that.

• 38:51David Weisburd?

  Me and my wife, Jessica, we have this concept of is it world class? We talk about everything. We go to dinner. Was that world class? Was this, you know, she'll put out social media piece. Was that world class? We hold ourselves to kind of this world class standard in most things. But sometimes you go to Whole Foods, you don't have to make it be world class. But we try, we apply this filter to a lot of things and it's kind of fun because it makes everything kind of like this pursuit of excellence. Um, and, and it makes every piece of your life me- meaningful and memorable.

• 39:23Speaker 01

  Absolutely. And then, you know, we have a different sort of permutation of that in our hole, which is I say to myself all the time, Pete, you're better than that. You know, you're better, like whatever you're doing, sort of like you're better than that. And I tell my kids, you're better than, you know, you can do better than that. And like, when you think of, when, when, when you, when you realize that I haven't reached the summit, despite my success, I haven't reached the summit yet. I haven't reached the pinnacle. I got more, I'm on the rise, but I got more climbing to do. And that means that every single day you gotta be a little bit better than the day before. And, and, um, you know, so maybe not world class for me, but just better than yesterday.

• 40:01David Weisburd?

  I'm not, no, you mentioned Amber Van's Box from LTK, who's one of your fellows at the Aspen Institute. Arguably one of the most prestigious fellowship in the world. You also have other fellows, Reid Hoffman from a founder of LinkedIn, Reed Hastings, founder of Netflix. You have these like really world-class entrepreneurs, like another level, you would argue. What have you learned from them?

• 40:25Speaker 01

  It's almost like what have I not learned? I, I, I, you know, so I was a 2019 fellow. There's 20, 21 of us in my class. Um, and um, I, I almost all the things I, the skills and knowledge I deploy today comes from my experiences in the Crown Fellowship at the Aspen Institute with people who are brilliant. I, I would say one thing I learned is this, I learned I was too judgmental of a person. You know, because when you walk into a room, a seminar room of really brilliant people, it's hard. Like when you're a CEO and you're building these big companies and everyone is telling you how great you are. And every meeting starts when you enter the room and every meeting is about you taking oxygen out of the room.

• 41:06Speaker 01

  Like you start to think that, you know, you're the greatest and, and you matter a lot. And the truth is, is like, when you sit in a room of 20 people who are your equals, as successful, as rich, as smart or better on all those fronts than you are. It's a humbling experience. Um, but it took, and it took me a little while to get acclimated to it. But the truth is, is it like, hey, you know, just being honest, like some of my friends have different political ideologies than I do, like very different. And instead of dismissing those, what I have to say to myself is, is like, no, my, my, my peer here is brilliant. Like, and they're smarter than me. They've been more successful than me. How can I not listen and learn from them, listen to them and learn from them?

• 41:49Speaker 01

  And so I, I think like probably the number one thing is suspend assumptions and suspend judgment when you meet people, especially people you respect. Um, and, and just really listen effectively. I used to, David, I used to spend a lot of my time when I was talking to someone, even someone who's really brilliant. You know, I was spending a lot of my time thinking in my brain how I was going to respond to them versus listening to what they were actually saying and digesting it. And my fellows have taught me that they are worthy of being heard. Uh, and then if I actually suspend assumptions, suspend judgment and suspend the desire to like, think about what I'm going to say next and really listen to them first. I'm going to, I'm going to become a much more whole and complete individual. And so it's been a remarkable journey with my fellows.

• 42:33David Weisburd?

  Suspending disbelief, especially when you're looking to level up your skills is so critical. You mentioned Spartan races, just to use that example. If let's say you're top 5% in the world and you meet somebody in the top 10, the point 001%. You start interviewing them about what they're doing. Almost everything is going to seem counterintuitive and you're going to have this egotistic drive to say, "Well, no, I do it this way," not realizing that the way that they do it is the reason they're the top 10. It's not only some weird side effect and some quirk is actually the reason you're not on the next level. In other words, it's not that they're training five times harder or that they're biking for 20 hours in a day versus four hours. It's that they're doing something fundamentally different

• 43:18David Weisburd?

  and that difference is the reason why you're top 5%, they're the top in the world.

• 43:23Speaker 01

  Yeah.

• 43:23David Weisburd?

  Yeah, in fact, there's an argument to make it. For those of you who have read the Harvard Business School case study, "The Making of the Corporate Athlete" by Schwartz. What he says is sometimes you realize that the reason people are superior to you in whatever domain you're interested, in whatever domain you're thinking about, is because, not because they work harder, it's because they rest harder. And the Harvard Business School case study talks about athletes like Usain Bolt, who for 10 years was the fastest man in the world, right? And what Bolt would often say is, "I take my rest as seriously as I take my training." And so I learned from that. Like, I wasn't big on rest. I was big on sort of being a 24/7 CEO. But now I know that I'm better and I can perform better when I get my rest

• 44:08David Weisburd?

  and I spend my time away and I'm absent from time to time. But yeah, lots to learn from other people. Sometimes, like you said, counterintuitive. But if you suspend judgment and you suspend assumptions, you can really grow. Another thing that I found really surprising about just excellence in any field is oftentimes it's idiosyncratic in a certain way. So to use Usain Bolt, he might be the best runner in the world, but he might be boring conversationalist or he might not even be a great dad. And like, just from movies, we assume that these packages come in these like perfect people. Like, he's Bruce Wayne, he's Batman, he's super intellectual, all these things. But oftentimes, they're just extremely good at one thing.

• 44:54David Weisburd?

  And sometimes even that one thing in Silicon Valley, it's well known, some of the top entrepreneurs have some degree of autism where they're able to go against the grain. And that like autism basically helps them ignore the herd like behavior of their peers. So sometimes not only are they different in other ways, but sometimes that difference is actually the source of their competitive advantage. Have you found that? And do you have any examples of that?

• 45:16Speaker 01

  I myself am neurodivergent. And have some learning challenges. One of the scariest things about the Aspen Institute is when I walked in and you have to do tons and tons of reading, hard reading, and really digest it and process it for the Aspen Institute every time you go into the seminar room. And like, I kind of felt so much different because I had to read, because of my learning differences, I had to read the text four times to, you know, the one time that my colleagues had to read, my classmates had to read it. And so I do believe that my brain zigs while other people zags. I like to be a contrarian. I like to think different, thinking different is fun, it's fulfilling. One of the things that drives me more than anything, David, is being underestimated.

• 45:57Speaker 01

  So I was a really good basketball player growing up and, you know, as a 5'9", you know, kid, growing up in Toledo, Ohio, I wasn't sort of, I probably didn't meet the profile for, you know, really good basketball player. But because people questioned my ability, I worked even harder. I demanded more of myself and that underestimation has always, has always driven me. So I like proving people wrong. I'm on a journey now with this new company to prove to people that I think social media can be kind, that social media, social media can be offered without the side effects. A lot of people think I'm nuts and I'm sort of trying to go up against Facebook or Instagram and, and, and the way you think about, you know, social media. But, but I think there can be a form of social media that is a social antidote. I'm thinking about it way differently than everybody else.

• 46:42Speaker 01

  Like, why do we need ads and influencers and likes and followers? Like, that's been my entire upbringing with my dad telling me, don't be a follower. And now the entire world is a damn follower. So like, so I, um, yeah, I think thinking differently is fulfilling, it's fun. And because of my neurodivergence, I get the benefit of thinking differently and being different. Uh, and while at times that can be hard and people can question you or give you diminishing stares. Uh, again, because I've learned that I just don't give a shit what people think anymore. Like, you know, I, I leverage the fact that my brain zigs while there's zags. Cause I think it, it builds moats and moats are ultimately what builds successful enterprise.

• 47:22David Weisburd?

  What is one piece of timeless advice that if you could go back to before you started Green Thumb and you could give yourself one piece of advice that either accelerated your success, avoided your weaknesses, what would be that one piece of timeless advice?

• 47:36Speaker 01

  John C. Maxwell, who was an author on leadership, you know, had a quote and I, when I first read this quote, I was like 29. It really, in so many ways, changed me. And he says, "The biggest gap in the world is the gap between I should and I did." And I'll repeat it again, "The biggest gap in the world is the gap between I should and I did." And you know, like, look, if I had a dollar for every entrepreneur, wannabe entrepreneur came up to me and said, "You know, I should start this. Here's a great idea. You know, I'm gonna quit next week," who like never ended up actualizing themselves, never ended up quitting next week, never started the business, like, I'd be way wealthier than I am right now. Like, I just, there are too many people who say I should. And what I

• 48:21Speaker 01

  learned is like, if I'm thinking something, I'm just gonna do it. I'll give you a good example. Like, I have this discipline now, where if like, I'm thinking about a friend or a loved one over the course of a day, I don't let that thought, thought become a fleeting thought. I don't let that thought go. I simply text them. It's like, my friend Yvonne, the other day, she's, she's sort of in a career transition and I hadn't heard what she was, you know, gonna be doing. And she's a brilliant woman. I hadn't heard what she was gonna be doing in her next go around. And so I was like, you know what? I'm just gonna text her. Be like, "Hey, haven't heard from you a while. Like, what's next for you?" You know, I stopped like not doing things that I said I should do a long time ago. And if all of us adopted that mindset of like, I don't stop at I should, I proceed

• 49:04Speaker 01

  directly, straight to I do. I think that helps eliminate a lot of the, the issues and inefficiencies today for most people.

• 49:12David Weisburd?

  We've actually operationalized at our firm, which is, how do you change I shoulds to I dos? You have to celebrate version ones. So we call it like the shitty version one. So anytime we have the shitty version one, which is every single version one in the history of time. We celebrate it and we celebrate the mediocrity of version one because doing it is actually exceptionalism. So it's a bit of a paradox.

• 49:37Speaker 01

  It's an exceptional execution mediocre output.

• 49:42David Weisburd?

  And if you just, if you just operationalize that, you will have an organization that builds, that does versus shoulds.

• 49:50Speaker 01

  Absolutely. You know, it's like, uh, there's lots of quotes on this, but my favorite is from Joe Gebbia and Brian Chesky to Airbnb. They had this line that I love and they say 80% equals done. You know, like, don't, don't spend in a winner take all market where speed to market matters. Like, don't try and get to 100. Don't make perfect the enemy of good, right? Um, just like, do it. Get it to a place that's the best possible place you can get it to. I, I don't call it the shitty product. I call it the MLP, the minimum, minimum lovable product. What is something that is minimally, minimally lovable about this offering and get it there and, and then you don't need to get to the rest of the way. Then you iterate and learn and sort of get

• 50:32Speaker 01

  the feedback loop going and, and grow from there. But I, I, I always ask people like, all right, you submitted this work product. Like, where are we at? Like 50%, 70%, 90%? Like, you don't need to be at 100. I want to make sure we celebrate 50 and 70 and 80 on the way to getting to 100.

• 50:50David Weisburd?

  Well, Pete, oftentimes with podcasts, and I find myself biased in this way, we take just extreme excellence for granted. I have the, the dream of interviewing people like you, but you know, just talking to somebody in the flesh, somebody that's come from nothing, built, took a company to $6 billion, now multi-billion dollars. Although you could have balanced work-life balance, arguably, I would argue you couldn't. And you could always tweak things, just the exceptional outcome that you've had and exceptional kind of philanthropy that you've done. It's, it's truly an honor to sit with you and appreciate your time and I look forward to continuing this life.

• 51:28Speaker 01

  This is awesome. I appreciate it. And, uh, I'm, I'm eager to learn more from you and from others who are listening. So please reach out to me and let me know what I can learn from you.

• 51:38David Weisburd?

  What would you like listeners to know? Or how should people follow you?

• 51:40Speaker 01

  Uh, I would say follow me on LinkedIn, reach out to me through email on LinkedIn and, uh, my new business, warmer.com, just the word warmer, uh, like a temperature warmer. Um, check out what we're doing there. I think it's going to be pretty game changing. Uh, if you're interested, sign up and, you know, start to meet some people on our new platform of social media.

• 51:58David Weisburd?

  Perfect. Well, thank you, Pete. Thank you, David. That's it for today's episode of How I Invest. If this conversation gave you new insights or ideas, do me a quick favor. Share with one person in your network who'd find it valuable or leave a short review wherever you listen. This helps more investors discover the show and keeps us bringing you these conversations week after week. Thank you for your continued support.