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We Asked a $15B Investor How to Survive the AI Bubble

My First Million

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  • Alpine Chased Number One Returns With A 5x Standard
    • Graham Weaver said Alpine set a goal 15 years ago to become the top-performing private equity fund by net MOIC.
    • He said the four funds launched after that goal all did 5x or better, while trying to treat people well and be a force for good. Transcript: Graham Weaver About 15 years ago, we set an objective to become the number one performing private equity fund in the world as measured by net moic you know the return on capital and our last uh since We set that goal the four funds we invested after that have all done 5x or better or the fourth one’s on track to do that so it’s been it’s been’s been great. Like it’s all the, all the content that I try to bring to my talks or to the students at Stanford, you know, I, I like to think they’re really based in stuff that really works. There’s a lot of, a lot of amazing people that are, have a lot of really good motivational content. I, I like to try mine out in the real world a lot and see what actually, what actually works. And I’ve, and I think that, you that I try to talk about is exactly what we do at Alpine. But yeah, we’ve had a really great run. And I’m really proud of how we’ve done it too. We’ve done it with people, treating people really well. We build our entire business around the people at Alpine and the people, the entrepreneurs in our portfolio. And try to be a force for good. The three goals are being the top performing fund, be a force for good, and be a place where the best people want to come and work and spend their careers. And I think hopefully we’ve done it that way. (Time 0:02:01)
  • Why Navy SEALs Running Plumbing Companies Works
    • Alpine’s buy-and-build edge is talent, not financial engineering.
    • Graham Weaver backs high-attribute operators, often military veterans, into boring industries like plumbing and HVAC, then repeats the model across huge fragmented markets. Transcript: Shaan Puri Are you guys buying like HVAC companies? Are you buying software companies? So, um, I mean, private equity is a very broad classification. There’s lots of different strategies. Graham Weaver So I’ll tell you specifically what we do. I know there’s a lot of talk around AI buy and build, if we can dive into it a little bit, but we do primarily buy and build. So we’ll find a really amazing CEO that a lot of times has worked with us in a smaller capacity. Maybe they were the CFO of a company we had, or they came through our training program, and then we’ll back them. We’ll go find an industry that we think is really interesting. We like the prosaic industries, like the ones you mentioned, plumbing, HVAC. We also do software too, because there’s a number of strategies where roll-ups and software can be really attractive. So it’s a small part of what we do though, smaller than the services stuff. And, but a lot of these really prosaic industries are massive. You know, the plumbing and HVAC industry mentions like, it’s like $170 billion industry. So it’s, so if you get it right and you actually figure it out, you know, you can, you can grow, you know, almost forever. Cause you just don’t run out of, run out of TAM, which is why we like the buy and builds because we’ll get it right once and then we’ll stamp it out a number of times. The other thing that’s really cool about buy and builds is it really is plays to our core competence, which is just talent, you know, so we’re the buy and build strategy, the way we do it Really is a talent strategy. You know, we’re in a lot of cases, we’re putting high attribute, like military veterans in to go run these, a plumbing business. And they’re just incredible leaders. And so our secret superpower is really training these awesome leaders and giving them an opportunity to do something they might not have had the opportunity to do otherwise. (Time 0:04:20)
  • Alpine Built A Search Fund With Infrastructure
    • Graham Weaver treats Alpine like a search fund upgraded with an in-house sourcing and acquisition machine.
    • Instead of asking one operator to build a PE firm just to buy one business, Alpine finds the CEO first and handles the deal work itself. Transcript: Shaan Puri The main part of your model that’s, I would say, kind of differentiated is you kind of, I don’t know if it’s not a search fund exactly, but you basically start with an operator or a CEO in-house, Which most private equity guys don’t do, right? They’re mostly like, we buy you. We hope the management team really stays on. That’s really important. Or we’re going to later install and do a search for an executive to run the company. But what you guys are doing is you start with the person, you kind of run a search with them, it seems like. Tell me what I get wrong. Is it not, like, what’s different about it than a search fund? They come in-house, basically, is the difference? Graham Weaver No, Sean, you nailed it. It’s like a search fund where we try to improve on the search fund model. Like, if you think about a search fund, and for those who may not know, you know, search fund is you’re backing a young person to go buy a business and then they’re going to go run it. But, um, the thing where it kind of falls down is the first part, which is someone has to go source and buy a business. They have to go build an entire private equity firm to buy one company. So we do all that ourselves because we are obviously doing this repeated on a repeated basis. But the general part about having a really high-attribute person betting their career on a business is a great formula. It’s probably a lot of what you talk about on this podcast. I mean, it’s the greatest formula there is. So we love that part of the DNA of a search fund model. We’re hiring very similar kind of high-attribute people, maybe a little bit older than the search fund, a little more experienced, bigger businesses. But generally it is what you just said, Sean. (Time 0:07:05)
  • Each Acquisition Adds Another Superpower To The Playbook
    • Buy-and-build gets stronger with each acquisition because every company contributes a distinct operating advantage.
    • Graham Weaver said after ten plumbing deals, the eleventh business effectively inherits ten superpowers through a shared playbook and Alpine-installed leadership. Transcript: Shaan Puri The simplified way of thinking about this is you find a really high attribute person, We’ll call them the Navy SEAL for now. Just so you know, somebody who’s clearly a go-getter, a winner, organized, effective individual who’s willing to work really hard for five, six years to create like life-changing Wealth for themselves and own their own business without having to come up with a great idea from scratch. You go with that. You’re already looking at whatever, hundreds of deals. You have thesis around stuff. You go and you buy the best deal you could find there. Now, And then you do add-ons. So you go buy the plumbing company. It’s already a good business. That person should operate it maybe to be a better business growing organically. Graham Weaver And then you’re going to buy maybe more tuck-in plumbing businesses to grow the thing using the cashflow from the first business. Exactly. And then the other thing is once you bought 10 plumbing companies, you know what it looks like to run the best in the world. Cause this one company might do really well on training. This other company does great on customer acquisition. This other company has a purchasing advantage. This other one has a training advantage. So you steal the superpowers of each. Exactly. You grab, and usually that’s true. Usually each company has a superpower, but after, let’s just say 10 deals, you’ve got all the superpowers, you know, and now your next deal, your 11th deal has 10 superpowers. Often you can improve that business dramatically really fast just because you take that playbook. And the reason you can make that playbook consistent is because you’re putting your own people in to run it. This took me 10 years to figure out, but we would, we would back founders and then say, Hey, we have all these great ideas. And the founders would just smile and write stuff down and never do anything, you know? And, and that’s not that we don’t love founders, but you can’t, you’re not going to buy a guy who’s run a plumbing company for 35 years and be a, and then, you know, come in and tell them how Shaan Puri To run this business. (Time 0:09:03)
  • Lawn Mowing Self Help Rewired Graham Weaver Early
    • As a teenager mowing lawns, Graham Weaver listened obsessively to Brian Tracy, Tony Robbins, and Earl Nightingale on a Sony Walkman.
    • He says two ideas changed him: stop making excuses and write down goals every day. Transcript: Graham Weaver Like what’s, hard about this yeah well uh first of all thanks for the kind words i appreciate them but uh i grew up in a small town in ohio went to a public school and it was a blue collar town Outside of toledo called perrysburg nothing special about it and um I was, I was probably just average in just about everything, athletics, school, and this isn’t false humility. I mean, this is actually, I didn’t make the basketball team. I got cut, you know, from the wrestling team. I mean, I, I just wasn’t really, and I was, I was okay at grades, not nothing special. And just as you said, Sean, you know, I, I was mowing lawns and I started, Stoney Walkman came out and I started listening to tapes by guys like Brian Tracy and Tony Robbins and Earl Nightingale And guys like that. And so imagine you’re like a 14-year kid and you’re literally and figuratively brainwashing myself with this content because I listened to so many hours of it and walking back and forth. And the two big concepts, the first concept that they said was, you’re either going to be your own best friend or you’re going to be your own worst enemy. So you figure out you first, you know, like you think that the world’s happening. Like, for example, you think you got cut from the basketball team and all this stuff happened externally, but really it’s you you know and and that was a very hard message to hear because I was like wait what do you mean uh I had all these excuses lined up like I wasn’t tall enough and I hadn’t started playing early enough and my parents didn’t get me in wrestling early enough And all this stuff it’s like nope you don’t get to have any of that stuff. You gotta, it’s like, you gotta get rid of all that and just, you gotta accept total accountability for your life. And that was absolutely brutal. And I realized they were talking about me and I wasn’t doing that. And I was exactly who they were talking about. So if the first thing is kind of get out of your own way, the second one was like, figure out what you really want. And I give Brian Tracy the most credit for this about like how to set goals. And I think he may be the best, you know, at least back then was the best in the world at setting goals. And so I literally would write down my goals every single day, multiple times a day in high school. And it was just incredible. The combination of those two things, it’s like pretty undefeated formula, you know, get out of your own way. Don’t allow yourself to make excuses and then write down what you want. Be super clear. And then, and obviously you got to go do this stuff you write down. But that, that formula was like really powerful. And there was just something in me, I guess, that wanted more than what I had. And so I just kept plowing through. And then the story is definitely not even close to linear. I mean, everything you could imagine goes wrong. I mean, I wasn’t great at wrestling. I cut a ton of weight in wrestling. I mean, I was 125 pounds at six feet tall. I mean, do that math. And then with Alpine, I mean, our first fund lost money, drained my savings account. Then we started calling our way back, got smacked by the Great Recession, drained my savings account again. You know, so it’s definitely not been a linear story at all. But I think the story is just one of like being clear about what you want and then just this crazy amount of like persistence. (Time 0:11:23)
  • Why The AI App Layer Looks Most Fragile
    • Graham Weaver thinks the most overhyped AI segment is the app layer, where venture money is flooding in.
    • He argues many apps sit between customers and LLMs without durable moats, so today’s fast revenue can still end at zero. Transcript: Shaan Puri I want to hear from you kind of like, how do you see the world in the market? Like, where do you see opportunity? Where do you see destruction? And where do you see overhype I want those three categories from you. Opportunity, destruction, and overhype. Graham Weaver Okay. I’ll start with overhype. How about that? You know, I graduated from business school in 99, which was like, it felt like this exact time right now, but it was the dot-com era. That was the time when you had like petfood.com and web van and all this nonsense i think the i think there were 400 companies that went public and the only one that i’m aware of that survived Was amazon maybe ebay um but it was like it was a bloodbath and and so people were right that the internet’s going to transform the world and look at us right now we’re on a podcast having, You know, over wifi. Shaan Puri And by the way, I can order DoorDash, uh, just like Webvan might’ve wanted to do Instacart, right? Even the ideas might’ve not have been terrible, but the way they were burning money and, and, you know, that wasn’t. Graham Weaver And, you know, you think about today, I mean, your, your mobile phone and you think about like, imagine just your wifi doesn’t work for a week good luck you know like that so it transformed The world more than people could even imagine back then but there was a lot of like false starts and hype that people didn’t really know where to place it and they kind of misplaced it i Think that’s kind of where we are in ai and my example of i’ll just just to back up i think there’s kind of four places you could play in AI. You could be in the infrastructure layer, which is really, you know, all the chips and data centers and energy. And, you know, that’s a very exciting area. That’s going to have growth for as long as we can see. Then the next is the large language models. There’s really not a lot of those. So, you know, I don’t know that you can really play there unless you’re a big business and even investing in those, like you’re already paying a price that assumes success for those. So I don’t think that’s really that interesting. Then there’s the app layer, which is where most of the venture money is going. And then there’s the use case layer, which is you’re a customer, like an HVAC company, and you’re going to use AI. And I think, and, and, and that’s, you know, that’s why I think a lot of these venture firms are jumping into these AI roll-ups because they’re realizing that the first three layers are Kind of tough and they’re going to play in that fourth one. But where the hype is, is the third one, which is the apps. You know, I’m going to be an app that I’m going to help law firms settle their cases faster. I’m going to make call center software that’s going to allow you to not use humans or I’m going to whatever. I mean, there’s a million of those applications. I think that’s where a lot of the hype is. We see all these companies as vendors to our businesses. So they’re pitching us all the time, these venture backed apps, and they’ll have 2 million of revenue and a $500 million valuation. And they’re going to go to zero like they’re going to be worth absolutely zero but a lot of them are a lot of them are getting like huge revenue fast are you saying that you think some of those Sam Parr Guys are going to also go to like is it is the churn going to be so high they’re going to go to zero i think that you have to say like ultimately what’s the barrier and what’s the moat that they’re Graham Weaver Going to be able to build there are there will be apps that will be successful, just like there were dot-coms that were successful, but they’re going to get attacked by above and below. You know, they’re getting attacked below from the companies that can have now, they can build their own stuff. They’re getting attacked also from the LLMs who are introducing interfaces and new products that are like literally just taking the business to some of these apps. So there’s going to be this constant pressure on them. I think if you can build proprietary data sets, which is harder than it sounds, or you can build really deep interfaces with your customers, which is also harder than it sounds, those Are moats you can build. But really, I think sometimes what you’re really, you know, you might be six months ahead of where the LLMs are going to ultimately go and that you can make a lot of revenue for a short period Of time. Again, going back to the internet, there was a ton of businesses in the, you know, 90s where it was like, get your marriage license online. And those businesses made a fortune and they grew really fast. Hundreds, I mean, they were growing at a hundred percent plus a year. They were until Google just absorbed all those rents, you know, what’s like that. And that’s a little bit of like the analogy of the LLMs, I think, absorbing a lot of the rent. So I’m not making a blanket statement that all apps are going to fail. I just think that’s, you asked where I think things are overhyped. (Time 0:15:17)
  • AI Roll Ups Still Depend On Old School Execution
    • Graham Weaver thinks AI roll-ups still win or lose on recruiting, culture, training, and integration, not proprietary tech.
    • In sectors like property management, he expects the technology itself to commoditize and flow through shared software vendors. Transcript: Shaan Puri There’s a bunch of like AI roll up. So it’s like, oh, let’s go buy these service businesses, smash in some AI, baby. Let’s put some AI in the front door. Is there a back? Let’s put some AI back there. Let’s shove some AI under there, right? It’s like me with a Thanksgiving plate. I’m just trying to put mac and cheese everywhere. They’re just like, we’re going to buy a company, we’re going to throw AI in it, and it’s going to be awesome. Is that a good strategy? Graham Weaver I think the reason that people are approaching the strategy is because they’re probably seeing a little bit of what I was describing about the app layer and saying, gosh, I’d rather Be the person using the AI than someone developing it. So I think that’s why they land in these AI roll-ups. I think you gotta be careful. I mean, we’ve been doing roll-ups for 15 years and AI is a huge thing. It’s important, depends on the industry, of course. Some in the trees are, AI is a much bigger factor than others. But the other basics of like getting the talent right, getting the companies right, integrating, doing the transition management, having your workforce stay on, you know, doing Training, recruiting, those are really the core elements. The technology, I mean, here’s probably a hot take. I think the technology in many, many industries is going to be commoditized. You know, like, I’ll give you an example. I’ll give you a real example. In property management, we happen to be in property management. I know there’s been a bunch of AI native roll-ups launched by venture firms in property management. What technology, like, what’s their real advantage? Like, are they going to have technology that’s better than anyone else? I would say the answer is no. So what’s the moat then? Exactly. Like, the moat in property management is all the stuff I was mentioning before, you know, hiring well, building, you know, good cultures, retaining, recruiting. But the technology, at least in that particular segment, is going to come through the, I think the software companies are going to. And so we’re all going to have access. And this is my take. You know, this isn’t, I mean, there can be other opinions on this, but I think ultimately, I think most people are going to have access to the same technology. It’s not going to be the thing. It’s not going to be the real differentiator. And so I still would go back to say, if you want to win in AI roll-ups, you got to win in all that other stuff I was saying. (Time 0:20:11)
  • Build Services Businesses Where Relationships Beat AI
    • Graham Weaver would start a services roll-up in an industry where deep customer relationships create stickiness.
    • His example was wealth management that bundles investing, taxes, trusts, and estate planning while using AI as a backend tailwind. Transcript: Shaan Puri If you’re teaching at Stanford, I’m sure somebody’s raising their hand and saying, hey, I graduate, you know, next semester. What should I go do? Like, where should I go? I’m a smart, hungry person who wants to be successful. You see the landscape and you know what’s going on. Where should I be going? What should I do? What’s the opportunity? Graham Weaver I would say if I were graduating right now, I mean, knowing everything I know now, I would go do a services roll-up because I know how to do that. It works really well. I think AI is a tailwind. I do that in an industry where you can build real moats and stickiness with the customers. Not all industries allow that. Shaan Puri What does that mean? Like services, you’re talking about like pest control. What are we talking about here? Graham Weaver Like take wealth management, for example, you know, if you go into that business and you’re like, okay, well, I’m helping people buy stocks or whatever, but what if you were helping People buy stocks and you were doing their trust and you were doing their taxes and you were helping them with all their estate planning and, and, and, and, and, and that’s your mode against AI. It’s old fashioned stuff. It’s, it’s your mode against AI is like the deep, deep relationships with your customers. So I would say go into something where you can really build those kind of customer moats and then AI is nothing but a tailwind for you because your customer doesn’t care how you’re doing Your backend, you know, but I would just be playing around with that. I think it’s like, it’s going to be a language that I would advise anyone, anyone, no matter what age you are, but it’s certainly if you’re a young graduating, like you want to know that Language extremely well. You want to speak that language because that’ll also allow you to look at an opportunity and say, okay, I know I could do this with it because I’m so facile in these tools. (Time 0:23:32)
  • Building Beats Financial Engineering Over Time
    • Graham Weaver argues ripping businesses apart can create quick gains, but building them creates durable upside.
    • He says firms that cut teams and raise prices may earn 1.5x to 2x, while strong teams let time compound toward far larger outcomes. Transcript: Shaan Puri You must be great at the ruthless analysis of business and finding the levers, cranking out that gross margin and doing all of that stuff while still like clearly not getting, not becoming What the caricature that Sam’s painting. Yeah. Graham Weaver You know, like if I had to keep it really simple, I would, I would say like, let’s pretend for a second that I wasn’t interested at all in being a force for good. And I was just interested in generating returns. I’d run my business exactly the same way. A lot of it is for me is like, it’s, the confidence in building something that’s going to be durable and enduring. So like, I’ll use a real example. Let’s say that I have this strategy. I won’t use any names, but let’s say I’m a software buyout firm. And my strategy is I go into a business, I buy a software company, I fire people and I double price. I’ll make money in the short term, but you look at a time like now where AI is coming, like you really want, the companies that are going to win in software have incredible teams that are On top. They’re making, you know, agentic products on top of their software. And they’re going to, they’re going to, they’re going to have AI be this incredible tailwind for them. And, you know, if you, if you just destroyed your, your, your team and your cost structure, you’re going to get attacked from, from both sides, from your customer side and from, you know, The LLM. So we found that building things, it’s a lot more durable than ripping things apart. Cause you can make like one and a half times your money, or maybe even two times your money ripping stuff apart if you’re lucky, if you time the exit just right. But if you actually build something, time’s your friend, and it could be, I mean, you can make a hundred times your money. And so I do think a lot of it is time horizon. I think underneath that is even deeper. Like, why are you in this business in the first place? Like, if your goal to be in the business is to make money and you want to do it as fast as possible, then maybe that behavior does flow from that. But in terms of just being good at private equity, I don’t think ripping things apart, I don’t think you’re going to be the best in the world, you know, doing that. (Time 0:26:12)
  • The HVAC Deal That Went From 8M To 500M
    • One Alpine HVAC deal grew from $8 million of earnings to $500 million in six years.
    • Graham Weaver credits a trio: AJ Brown on talent, Will Matson on finance and M&A, and Ira Pruitt on the operating playbook. Transcript: Shaan Puri The best deal you guys have ever done? What’s the hero deal? Graham Weaver You know, we’ve had, we’ve had a few really, really good ones that rhyme with what I’ll describe, but you know, you picked the plumbing and HVAC example at the beginning. That’s one of our best deals. I mean, we, we back to people that we, we hired right out of a business school. They joined our CEO and training program. They went through that program. They became eventually the co-CEOs of the business. We bought a small plumbing and HVAC business that had like $8 million of earnings. This year, that business will do 500 million of earnings. Sam Parr How many years did that take? It took six years. Six years to $500 million. You have to break that down. Shaan Puri $500 million of earnings, not earnings. Graham Weaver Yeah, $3 billion of revenue, $500 million of earnings. And we, I think importantly, that happened without us putting in any additional money. Shaan Puri Wow, so an initial buy of like what, $30 million or something like that? Graham Weaver How much was the initial buy? We put in a total of 50 in the first deal. We might’ve put in like that first year, like another maybe nine or so that first year. Shaan Puri And then that was it. Then we never put in any more. What was going on? Was it that you guys just went on an acquisition spree and picked up all the mom and pops? Or was it that they weren’t doing any sale? They didn’t know, they didn’t have a good website. Like what was missing that you guys added? We got we got fortunate that the third deal that we bought, we partnered with this guy. Graham Weaver So the CEO is our name, AJ Brown and Will Masson. And then the third deal we did, we partnered with this guy named Ira Pruitt, who was like the the grizzled HVAC veteran. And just this wonderful guy. He had seven of his kids in the business and like, and he gave us a lot of the playbook levers. And then the next deals after that, we were adding to that playbook. So eventually we just ended up with this amazing playbook about how to run those businesses. And then we began that talent program we were talking about earlier, where we started attracting a lot of incredible leaders, a lot of, not all of them, but a lot of them veterans. And then that allows us to go buy businesses that other people can’t buy because like really the line of people that wants to go buy a $12 million revenue plumbing business in the middle Of Louisiana that requires a management change is short. Sam Parr It’s a short line. You have to address this. So you just, you described one of the guys, I forget his name, as a grizzled HVAC guy, which in my head, I have a picture in my head of what that is. So I looked up, the company you’re talking about is called Apex Service Partners, I assume. And I looked up Will Mattson. Sean, go ahead and look up Will Mattson. Graham Weaver Yeah, he probably looks like the opposite of a grizzled HVAC guy. Sam Parr Will is a baby-faced guy. Honestly, he looks and he might actually be 28 years old. I think he, he looks very young and he worked at JP Morgan and went to Wharton and worked at McKinsey. Graham Weaver So the grizzled guy is named Ira Pruitt and, and the combination of AJ, Will and, and Ira is like amazing. So that’s what I want to ask about. Sam Parr I want to ask about what makes this such a high-functioning team to go from $8 million to $500 million in profit. Teach me what makes such a powerful team and what attributes are needed in order to grow a business that fast because these guys look like the fairly odd couple. Graham Weaver They are an odd couple. So the combo in this particular instance, the combo is AJ is incredibly focused on the talent and he’s the one that rallies the Navy veterans and flies around and gets them excited. Will does the finance and the M&A and a lot of the hold co-functions. And then Ira is the one that’s like, hey, this is how you actually run a plumbing business. Here’s the playbook we got to implement. So that’s how the combination works. (Time 0:28:24)
  • The Trait Alpine Screens For Above IQ
    • Graham Weaver says the strongest predictor of leadership success is a white-hot will to win.
    • Alpine runs three-hour life-story interviews from high school onward, looking for repeated examples of setbacks followed by persistence. Transcript: Graham Weaver What they all have in common, and then to answer your question, like what we look for in these leaders, number one is just this white hot will to win. And that’s more important for us. We found that to be way more highly correlated than any other factor, IQ or background or experience. But like each one of these three in some version of their life has just demonstrated this crazy will to win. We learned this from a book called Who, which was the sequel to the book called Top Grading. And it’s about basically how to hire. And so we do like a three hour interview and you start with the person in literally like in high school and you go through yesterday and you’re just walking through their background. It’s kind of a conversation just like this. It’s not, it’s not super formal, but you’re, you’re collecting data on this person and you’re, you’re in, in A.G. And Will’s case, you know, you’ll, or, or Ira or really any, anyone that had gone through our program, you you’re just going to see example after example of like, hey, this thing went Really wrong and it was a bummer. And here’s how I handled it. I got up, I plowed through, I put my shoes, boots back on, and I kept marching forward. And you’re going to see that again and again and again. We always say, it’ll leap out of that interview. And if it doesn’t, then they probably don’t have it. (Time 0:32:10)
  • Turn Hidden Fears Into Solvable Problems On Paper
    • Ask what you would do if you could not fail, then write down every fear blocking that answer.
    • Graham Weaver says fears hidden in your head cause paralysis, but once written down they become solvable problems like rent, loans, or runway. Transcript: Sam Parr So you have this question of what would I do if I couldn’t fail? What would you say is the most common reason why people are really bad at answering that question? So there’s a few things I’d say. First is, I think people don’t ask the question. Graham Weaver So that’s probably 90% of people. It sounds crazy, but they never ask themselves, what do I really want? And they haven’t given themselves the permission to even think about that. Or, or, or like, I think it’s almost like the highest form of self-love is to trust yourself enough to say, I’m going to be on the path that excites me. You’re asking why people fail and say, so I’d start with people haven’t given themselves the permission to even think like that. So let’s, let’s now you have done that. But I would say for your audience, give yourself that permission. You matter. What you get excited about in this world matters. Shaan Puri What are some example answers to that question? You’ve obviously helped a lot of people go through this process, I assume, when you teach at Stanford. Graham Weaver I’ll give you a couple just from my class in the last couple of years. Last year, I had a student who’s building a theme park in Dallas, in Texas, like literally a theme park. Let’s give them a shout out. That was her dream. What’s that called? Yeah. I think it’s called Texas Land. I’m not sure. Maybe they haven’t finalized that as the name, but that was her thing and she’s going and doing it. I have a student this year who is, he is brilliant. He could go to any consulting or finance firm. He’s going to India, um, where his, his family’s from to help them build free hospitals. And like, that is his thing. Like it’s super clear that’s that’s his answer to the question i give him so much credit that he has the courage and commitment to go do that and it’s going to be very hard but that’s his Answer you know what you guys are doing i mean you guys are building a podcast that’s like really helping people and you can just tell from being on this podcast you guys love it you’re Having a blast like you’re doing it, right? I mean, you’re, you’re doing the thing that you follow that energy and gave yourselves permission to be like, Hey, that’s a good place. Sam Parr And but I, but I almost hate saying it that way, because I don’t want people to think that there aren’t doubts yelling at us or anyone who’s successful all the time. Because I think in another talk, maybe the same talk, you were like, I do this exercise and Alpine is a $20 billion fund. And I think you said for the first 14 years, you thought it was going to fail or you weren’t confident that I forget the phrasing, but you weren’t confident that it was going to be a home Run. Yeah. Graham Weaver I think all of us have these like crazy, um, limiting beliefs, like that run through our minds all the time that are like beating us up with like, I shouldn’t do this. I have to do this. I should do that. I might fail. Oh no. And the thing about that is that’s very normal. Like having that fear and those doubts is a hundred percent normal. Everyone has it. It’s just what, like, what do you do with that? And I think one of the things I try to help my students do is like, we have an exercise where literally, we like spend an entire class writing all that down. Like we like, like empty your mind of all the limiting beliefs that are getting in your mind. Just let them flow out. Okay. I might fail. I might run out of money. This, no one might watch my podcast. You know, Alpine might not make it. AI might not work, whatever it is, write all that down. And then, and then once it’s down on paper, you’ve removed it. Like it does the most damage to you when it’s in your subconscious and you don’t even realize you have it. So if you’re, if you’re walking around with some fear and you don’t even know you have that fear, it just looks like inaction and paralysis. And I’m not going to go forward and I’m going to stay stuck. But once you have it down on paper, let’s say one of your things is I want to start a company, but I don’t know how I’d pay myself or pay my loans or whatever. Okay, so fine. If that’s in your head, you’re just not going to start a company. But if you write it down, you’re like, you can rephrase and say, how would I start this business in a way that I could service my business school loans and still pay my rent? And now that’s a problem to be solved as opposed to a fear that is creating complete paralysis. (Time 0:34:16)
  • Test Career Paths By Energy Not Early Traction
    • If you do not know your path, list several exciting options and test them on nights and weekends.
    • Graham Weaver says do not judge by traction from five hours a week; judge whether those were the five hours you most wanted to do. Transcript: Shaan Puri Mercury is a fintech, not an FDIC insured bank. Banking services are provided through Choice Financial Group and column NA members FDIC. For the person who’s like, I want to build the theme park in Texas. Awesome. I want to build the hospital in India. Sounds great. I’ve been in that position before where it’s like, I’m ready to have that answer, but I have no idea. And I’m kind of saying one out loud. It doesn’t even feel right. I’m just making it up. And I had to, I’ve taught myself to basically go through this process of sort of dabbling. Like, you know, just take this mentality of a dabbler. Like, how do I go and run either lightweight experiments or brainstorm, or just not feel like I needed to commit right away, but like, go try to see where the energy is. How do you advise people to, if they don’t have the answer of, oh, this is the thing that would light me up. Like, maybe you don’t even know. Where do you go to figure that out? Yeah, I love that. Graham Weaver Well, here’s one idea is maybe don’t have one thing. Make a list of like nine things that would light you up. Okay, I think I’d like to go to India. I also think I’d like to start a podcast. Maybe I really want to, I don’t know, become a DJ. I don’t know. Write down your things. And then, like you said, you know, keep your day job and devote X number of hours a week to testing those things out. Maybe you’re going to do some work on it, take some classes. You’re going to start hanging out with people that do it. Maybe you’re going to get trained. Maybe you’re going to do podcasts and nights and weekends and see if it’s as fun as you thought it was. And you’re not looking there for, this is what I think is really important. You got to, you got to be careful that you’re not going to get a false negative on the outcome. So like a student who says, okay, I want to start a company. So I’m going to spend five hours a week this quarter. And if I get traction, I’m going to do it. Like, no, no, no, no, no. You’re going to get no traction. Like five hours a week. If you could build a business in five hours a week, like it wouldn’t be worth building, you know? So it’s not that you’re looking for, like, does it light you up? It like in that five hours a week, was that the five hours you were looking forward to that all week? Or was that five hours where you were like, kind of like, oh man, I got to do five hours on this thing. You know, like that’s what I think you’re looking for in those like experiments because by and large if you are lit up and you I mean you plus being lit up plus a long time frame there’s very Few things that won’t yield to that and that was me at Alpine you mentioned you know it took 14 years for us to know it was going to succeed yeah but I was fired up I was willing to do it for a Long time. And I was in it. I was excited. Sam Parr And like most things will yield to that formula with enough time. (Time 0:39:59)
  • It Took Graham Weaver 14 Years To Feel Liquid
    • Graham Weaver said it took 14 years from starting Alpine to have $1 million in the bank.
    • Fund one lost money, investors still re-upped because Alpine was transparent, and his first real liquidity came only after the last company in fund two sold. Transcript: Sam Parr No? Well, we lost money on our first fund. So fund one was 2001. Graham Weaver We lost money. How’d you get a second fund when you lose money on the first? Well, we were very transparent with our investors about what was going badly, what we were fixing, what we were learning. So they were like, okay, we see you’re on the right trajectory. You’re transparent. You know, at one point that fund was marked at 40 cents. We ended up returning like 95 cents. So they appreciated that and they gave us another shot. Thank God, you know? And, um, but, but what I was going to say is, so we had fund one, was it, you know, we had that anchor for more than a decade because these business you have to go in you buy the companies you Run the companies you sell the companies it takes probably 10 years and then fund two comes along and so it was kind of another 10 years after that after fund two where we actually had some Success you know where where we could have the outcome of that fund you know proving out that it was working. And so that’s the 14 years I talk about. But to give you the numbers, we were 14 years in, I want to say managing maybe two or three, three or $400 million, something like that. That sounds successful, right? It might sound like a lot, but we’re trying to run an entire team and we have all these portfolio companies. Shaan Puri Well, let’s ask the question. So we called the podcast, my first million. And when we started, there was a tradition. We would always ask every guest when, when and how did you make your first million? And we, we like to really put that in reference because a lot of times the answer was longer than people think you try to get, you know, when you’re 20 years old, you think it’s going to be When you’re 20 and a half, you know, you think it’s right there and it takes a lot longer. It took me, I was 30 when it happened to Sam, I think same thing, 30, 31. And so it takes a little longer. And also we talk about how did it feel? Like, what, did anything change? Graham Weaver And what changed? I love to hear that. That’s such a great question. All those are such awesome questions because it’s so not what I thought it was going to be. So a couple of different ways to answer the question. One thing to be a millionaire on paper, it’s another thing to have a million dollars in the bank. They’re different. They’re different feelings as you, as you guys probably know. One pays the rent, one doesn’t. Yeah. So I’ll say a million dollars in the bank. Cause I think that’s the, that’s when I actually felt like I had a million dollars. Yeah. And that was the, that was year 14. That was one week. No shit. That was year 14 of start. So I’m, I was 29 plus four. So yeah, I’m in my forties, I guess when I, when I made my, actually had a million dollars in the bank. But to put that in context, by the way, that is pretty slow. Sam Parr Love like having a, having like a PE firm, your job is to get good returns and to not having like that. Graham Weaver Well, yeah, I want to say what we had what’s called a European waterfall, which means we have to return all the money in the fund plus an 8% return before we take any profit. And so we had to, first of all, fund one generated no carry at all. And then fund two, we needed to sell. It was really the very last business in that fund that we sold until we got paid. So it was, that’s what I was saying, like the part about on paper versus in the bank. You know, I was a millionaire on paper before that, but actually in the bank, it was 14 years. (Time 0:42:44)
  • Wealth Depends More On Your Denominator Than Income
    • Graham Weaver thinks the biggest wealth mistake is letting your denominator grow with your income.
    • He says bigger houses, cars, schools, and commitments erase freedom, while a small lifestyle preserves the option to start something meaningful. Transcript: Graham Weaver But I want to, I want to talk about wealth for just one second. The interesting thing is like, I felt wealthy way before that because my denominator is, has always been small. So, you know, like there’s two parts of, of wealth. There’s the numerator, which is what you make in your denominator and what you spend. The biggest mistake, and this is something everyone who listens to this podcast can benefit from, the biggest mistake people make is the denominator. And so they go, like, here’s a perfect example. I really want to start a business. I’m going to go take this other job first. And then I’m going to make some money. And then I’m going to start my business. Okay, that’s what they say. Never happens. Because they go take that job. Then they get a new house. Then they get a new car. Then they move to this other city. Then they have kids. Then they have kids’ schools. Then blah, blah, blah, blah. And their denominator is keeping pace or even surpassing their numerator. And they’re never, they’re never actually feeling wealthy. And ironically, they’re creating less freedom every year, you know, because there’s fewer, fewer things they could do to maintain the lifestyle. And there’s no way they could, they could start that business. And so probably like one of the most underrated things that happened in my life is I married my wife who was an elementary school teacher and made $18,000 a year pre-tax. And like our first apartment that I think was like 900 a month, you know, she thought it was the Taj Mahal, you know? And like, so we never, I never really- Does the IRS just send you money if you’re making 18,000 pre-tax? Do you actually just get a bunch of money every April? That’s awesome. They literally should. They should. I mean she would drive around for like 30 minutes to save you know two dollars on parking i was like okay well we gotta not do that but but but that so yeah the denominator i so i felt wealthy Way before that because i i just had a big cushion between my (Time 0:46:03)
  • Money Solves Stress Better Than Self Worth
    • Graham Weaver found money’s steepest utility curve in peace of mind and freedom to spend time on work he actually wanted.
    • Beyond that, he says wealth disappointed him because external milestones could not fix the internal feeling of not being enough. Transcript: Sam Parr But I remember there was freedom in that. Graham Weaver I love that. I love that. And the freedom part is so true, Sam. Know, like the steepest curve of utility with money was going from like, the first one was having peace of mind of like not having to worry if I had to fix my car or whatever, you know, some, Some unexpected expense happened, but I’ve got money saved away and I don’t have to stress. That was, that was actually steep because that wasn’t always true for me. You know, like my car would break, I’d be like, oh no. You know, and then the next curve that was really steep was, I have enough money to do what I really want to do with my life. I mean, how magical is that? Like, that’s really where the utility, it’s flattened out after that. Sam Parr You know, so that’s really where the utility of money comes for me. But when you’re giving advice to your students, what do you tell them that number is? For example, some people say that financial freedom is 25 times your annual spending. Some people will say as long as you have six months of savings, that you’re good. Is there a threshold? Yeah, there is. Graham Weaver I would say having three to six months of savings is level one, which is the peace of mind. Because then, like I said, you have some unexpected expense and you’re, you’re fine. You don’t, you don’t lose sleep over that. You know, you don’t have to decide if you’re going to pay your rent or fix your car. That’s like three to six months of savings. That doesn’t sound like much. It’s dramatic. It makes a huge, huge difference in your life. And then the next one, I think it’s lower than that. Like when I say freedom, I don’t mean like the, like, okay, I’m going to live off the interest of my money. I have in treasuries, you know, that, that, okay. Sure. That that’s nice if you get there, but, but I’m not even talking about that level. I’m talking about, I’m spending, I’m still working, but I’m spending my day doing something that I enjoy that is the job that I want to have. I think that’s probably nine to 12 months of savings. It’s not that. So I think both of those are really within people’s grasp. People who are like, oh, I really want to get to the like you money where I never have to work or anything. And then what? You know, like, then what are you going to do? And I want to go back to the other question you asked. Did it feel the same that you thought it was going to feel? No, it did not. So when I actually had wealth and I’d worked and I’d go back all the way back to the lawn mowing and all the sacrifices I made and getting good grades and getting to the right school and then Getting the job and then suffering through fun one and then finally getting on the other side and then finally getting this big liquidity event it was it was like the most disappointing And like it because because i thought it was going to change everything it didn’t really change hardly anything and and like what was still there was like maybe the thing i’d been running Sam Parr From which is like i’m not enough you know like well so what what like what career milestone since everyone listening to this is interested in business but it could and family it’s too Easy to answer uh but like what career milestone actually did move the needle on happiness if it wasn’t like a financial thing is there anything else like for example you probably have Hundreds or thousands, I don’t know how many employees you have, whatever it is, like you’ve created like an institution. Has that made you feel good? What, what, what teaching at Stanford, what career milestone have you had that a listener can like, be like, okay, that’s like a cool idea on how he actually got happy via career? Graham Weaver Good question. There are two ways to answer it. First is, one answer is, you’re not going to solve an internal problem with the external outcome. So if I feel like I’m going to be enough when, whatever you answer that with is going to be disappointing to you. So on that answer, you can’t kind of get there with the career and, and you, you have to, at least for me, I had to do a lot of internal work, therapy, coaching, journaling, um, meditation And, and start to just like let go of this, you know, I’m not enough part. Created more happiness and peace of mind than the, than the career, probably the career achievement that I remember the most. (Time 0:48:58)
  • Use Meditation To Stop Letting Thoughts Run You
    • Most battles are you versus your own interpretation of events, so train the filter before trying to change the world.
    • Graham Weaver uses meditation like mental reps: notice thoughts, return to the breath, and build separation from self-attacking stories. Transcript: Shaan Puri Yeah, a hundred percent. And I’ll give you a couple things that I learned. Graham Weaver So one is almost all your battles that you have are you against you. It’s true. It seems like this whole thing is happening out there and you’re, you know, you’re winning this or you’re doing this and like, but you’re remember all that stuff that happens goes through This filter, which is called like the story you’re writing about it. Then it goes internal. And like, you can, you can change it. The easiest part of changing your life is to change that filter. You know, it’s, it’s way easier than changing what’s going on out there. It’s a lot easier to change how you’re interpreting it. And so you can either be your own worst enemy, or you can actually be your own best friend. And I can tell you that I was my own worst enemy. Like it did, it almost didn’t matter what was going on out there. I would look for what was wrong. I would have a bad story about it. I would beat the crap out of myself. And then I would tell myself another story, which is me beating the crap out of myself is why I’m successful. Total bullshit. Um, it was just what made me miserable it’s like running through life with your foot on the brakes so one is just that awareness like that wow i’m i’m having more to do with my peace of mind Meaning success uh happiness than anything that’s happening external i think if you really think about it you’ll realize that’s true and then and then the formula for like actually Programming, actually changing that, I finally understood like in a simple way why to meditate and how to be, how to be, how to make it work and how to have it actually impact your life. So you go to the gym and you work your bicep and your bicep, you break it down, it gets stronger, and then, you know, it regrows and is bigger. So meditating is very similar, except the muscle you’re working is your, basically your mind and your self-awareness, your presence. So you pick your meditation, you’re counting your breath, you know, that’s a simple one, right? You just close your eyes, you count your breath. And then your mind starts going off and talking about, thinking about whatever, you know, I’ve messed up this conversation or I should do this or I’ll get tomorrow, I’ll get to this, Whatever. And then you notice that and you, it might take you a while, but you notice that your mind just took off and you bring it back to your breath and you do that again. You’re basically building this muscle. You’re building a muscle. The muscle is like, I’m going to two things. One, I’m separating from my thoughts. I’m realizing those thoughts that are happening aren’t me. I’m creating this muscle of observing my thoughts versus just, you know, succumbing to them. And second, and even more powerfully, I’m building the muscle being present. Like if you want to have a great life like be present like if if everyone in the world was present and here right here all the time and not in their head like people would be like in this great State of joy like and so building that muscle of of watching your thoughts coming back and being present um is the same muscle of being your own best friend because you’re seeing like, Oh wait, I see that this thing happened and maybe I didn’t answer this question really well or I could let that thought go and just be here and like doing that over and over. (Time 0:54:54)
  • How Graham Weaver Helped His Son Choose Lacrosse
    • Graham Weaver used a future-simulation exercise to help his son decide whether to keep playing lacrosse after a brutal freshman season.
    • Instead of persuading him, he had him vividly imagine the next three years without lacrosse until the answer felt obvious. Transcript: Sam Parr I ask you really quick before we wrap up about parenting? I saw that you’ve got three kids. You blogged about how one of your kids went to college. Do you do any of these exercises with your children? And at what age did you start doing that? Or were they like, you’re my dad. I ain’t listening to you no matter what. Graham Weaver Above my kids are definitely like you’re my dad you know it’s funny because in most circle like worlds I’m I’m you know I’m a professor I’m running a firm or whatever at home I’m I get you Know I have teenagers like they’re ruthless right they make fun of everything I do um and uh I I do it in a in a way that’s not maybe as obvious but you know I’ll give you a real example it’s Easier you know my son was like trying to decide his friend he had a really tough year his freshman year and he was deciding if he was going to play lacrosse the next year because he had a Tough season it didn’t go how we wanted and it was brutal and so you know we i did a exercise with him and we said okay i said okay blake like let’s go through and talk about, like, I want you To play out your next three years as though you didn’t play lacrosse. Like, let’s go through it. Like, I want you to really like think through, okay, we get home from school. Here’s what you do. You know, here, here’s lacrosse season comes along. Your friends are playing, you’re doing this. Now I want you to go through and you go through the season, but it’s hard. You do this. After that he’s like i i definitely want to play lacrosse like i know for a fact that’s what i want like by the end you know when i get done with my my four years like i want to have gone through That and so yes i use these tools but it’s it’s more letting them kind of it’s in service of their, their lives. And, and it comes up more like as when they ask, almost when they ask for it versus me saying, okay, it’s Tuesday, we’re going to sit down and do this. Having said that, my kids also watch, you know, your kids watch what you do more than they listen to what you say. And so, you know, my kids have goals, they work hard, they write down their goals, they try their best, I like to think. (Time 0:58:59)
  • Motivation Must Be Hired But Systems Can Be Taught
    • Alpine does not try to teach raw motivation; it screens for it and then layers in battle-tested operating tools.
    • Graham Weaver says business results correlate almost perfectly with how fully leaders apply Alpine playbooks like Kaizen, process maps, and one-page planning. Transcript: Sam Parr What about your employees? Because when I listen to your stuff, I listen to your stuff because I’m looking to change my behavior. Most people don’t change their behavior, though. And you talked about hiring these operators, these people who have these wonderful backgrounds and who have a track record to where they have this white hot will to win. Are you able to change any of their behaviors ever when you hire someone or are you looking for someone who already has it? Graham Weaver So I’m definitely not looking to teach someone how to be motivated or to care or to run through walls. Like I can’t teach that. However, we’ve bought 800 companies. I’ve been doing, I’ve been in private equity 31 years. We built some incredible businesses. So we have incredible frameworks and tools and playbooks that we use that have been battle tested. And if one of the things we’re screening for is, do they have a growth mindset? Are they open to learning? And so if you look at our companies that we have in our portfolio, there is a pretty much a 100% correlation between how much of the playbooks they’re running and how successful their Businesses are. So they’re coming into Alpine wanting to say, hey, look, I’m 32 years old. I want to run through walls, but I don’t know how to run a business. Can you help me do that? And that’s a great partnership because we have so many great tools. Now, they will take our playbooks and they’ll make them their own. Five years from now they’ve added to it they’ve they’ve you know changed it they’ve they’ve they’ve made them better and they’ve made them work for them but but we’re definitely providing A lot of the foundation of like here’s some amazing tools you know like we have kaizen projects we run we have process mapping we have a one-page planning planning tool we use have you Ever published this and can i have it just like colonel sanders chicken recipe or is this yeah i’d be happy to share with you it’s probably come through in some of my materials but um but Yeah we, we’ve, we’ve, we’ve definitely codified a lot of this and over the years and yeah, I’m happy to, happy to share with you. (Time 1:01:13)