Last Lecture Series: How to Design a Winnable Game – Graham Weaver

The fan is blowing the sweat that he’s hitting into me. And I’m thinking, his sweat underneath him is starting to creep toward me. And I’m thinking, am I supposed to move? What am I supposed to do here?

Anyway, so this goes on. This routine that we have, the two of us go down to the boathouse. This goes on for about a week. He never acknowledges me at all. I would later find out that this person was Mike Teti. And Mike would go on to row in three Olympics and win a bronze medal. And then he would coach the U.S. team in 2004 to a gold medal. So he was a pretty big deal in U.S. rowing.

But anyway, he didn’t even acknowledge me until about a weekend. And he acknowledged me by giving me kind of one of these. Like this. And I played it really cool, so I gave him one of these. And then he kind of gave me one of these. And then that set us back another couple weeks.

But then three weeks in, we’re sitting in the locker room. And I think Mike’s curiosity just got the better of him. And he said, he’s like, “Who are you?” And I said, “I’m Graham. I’m a land warrior. Who are you?” And he said, “Well, I’m Mike.” And he said, “Well, Graham, what are you doing down here every morning? By the way, I also see you sometimes in the afternoon practice. Like what are you doing?” And I said, “What are you training for?” And I said, “I’m a land warrior. I’m trying to make the third string novice freshman lightweight team.”

And he said, “Well, Graham, your form is terrible. But I’ll tell you one thing. If you keep training the way that you’re training, you’ll make the Olympic team.” And I remember just this huge surge of energy came into me when this person I’d been watching, who was this Adonis of rowing, told me that.

Make No Little Plans

I love this quote by Daniel Burnham. He says, “Make no little plans, for they have no power to stir one’s blood.” The first blood that you need to stir is your own. And rowing stirred my blood. And being an Olympian, or even the idea of being an Olympian, stirred my blood.

And so what I knew back then about goal setting, I learned from this guy named Brian Tracy. I listened to one of his audio books. I think he’s one of the leading writers on goals. And what he said is, write down your three most important goals every day and write them in the present tense as though you’d already achieved them. And then write what you’re going to do to move toward it.

So I had this green spiral notebook, and I wrote down every day, “I am an Olympian.” And I wrote down the three things I was going to do to move toward that goal. And a funny thing happened. I started, a part of me started

believing that I already was an Olympian the day that I set that goal and started writing it down. And every time I did one of those things on that list, which is typically workouts or eating well or whatever it was, I started assuming more and more of the identity of an Olympian. And when you choose a goal that stirs your blood, there’s a part of you that will assume the identity of someone who’s already achieved this goal. And this is an incredibly powerful force.

And now, just writing your goal down doesn’t make everything rainbows and unicorns. I lost more seat races than I won. I didn’t make the boat I won in my freshman year, my sophomore year, my junior year. And so it doesn’t just happen overnight. My endurance didn’t change overnight. My strength didn’t change overnight. But I did get a lot better. And by my senior year, I made the varsity team. I was elected captain. Our team won nationals. And for one moment, I had one of, if not the top 2,000-meter time in the country.

So then I started thinking that night in October. I was looking back and saying, well, what are we doing at Alpine? What’s my equivalent of the Olympic goal at Alpine when things really weren’t going that well?

So this is what we had been working on. “Generate attractive risk-adjusted returns while maximizing the probability of capital preservation.” Let’s go. Who’s with me?

It’s humorous, but this is actually really, really scary. And this is a big part of what I’m trying to communicate today, which is what happens to all of us is that there’s a point in our lives where we have these incredible hopes and dreams. We have confidence. We want to go take over the world. We have all these amazing things that we want to do. And then life intervenes, and we might have heartbreak. We might have loss. We might have setbacks. Things don’t go the way we want. We might have people in our lives telling us that we can’t do things or we’re not enough. Or we might have a job where things don’t go the way we want. And little by little, we start to lower our goals. We start to not believe in ourselves and think maybe we’re not enough. And so we end up with a goal like this.

So rather than setting a goal of being an Olympian, we have the equivalent, which I would say this is, of trying to make the third string lightweight on this team. And we settle for this. And there’s two huge problems with this. The first problem is you will assume the identity of someone who’s working on this goal. And if you read this goal carefully, what it’s really saying is try not to lose money. And so I assume the identity of someone who’s holding on tightly to Alpine. We can’t invest in this. We can’t do that. And we’re not going to be big, and we have to stay in this little box. And that was the identity that I had assumed and why we weren’t winning, by the way.

And the second big problem is you’re setting off on a life journey that you don’t care if you win or not. And that might sound really obvious, but it’s not a winnable game if you’re not excited to win the game. And so many people, that’s the journey that you set off on.

The Power of the Right Question

So we started asking ourselves a better question. And the question, if you’ve taken my class or seen any of my content, is what would you do if you knew you wouldn’t fail? And this is my favorite question. I would encourage you to ask yourself this question maybe every month at least and answer this question in all the different areas of your life. What would you do if you knew you wouldn’t fail?

We had a hard time even answering this question. There were so many doubts and fears and limiting belief and past history and losses and things that kept clouding us that we almost couldn’t even answer this question. It took us months to come up with an answer.

But we came up with our equivalent of becoming an Olympian, and it was this. Be the number one performing private equity fund in the world and deliver 5X on every single fund. And just to give you an idea of the 5X, the top 25% of private equity firms in any vintage deliver about 1.8X to 2X. So we were going to be several standard deviations better. This was our equivalent of make the Olympics.

And by the way, at the time when we set this goal, it was the equivalently aspirational of me setting the goal of being an Olympian when I was a 135-pound mullet sporting novice who’d never rode from Ohio. That’s kind of where we were at the time we set this goal.

And a funny thing happened. We started showing up as though we were the people that were capable of achieving that goal. We started investing in different kinds of companies. We started attracting different people who wanted to come with us on the journey that we were on. And it hasn’t been rainbows and unicorns. We’ve had lost money on deals. We’ve had people leave. We’ve had CEOs not work out. We’ve had everything you could imagine. But we delivered 5X on the four funds that we invested subsequent to setting this goal, or three of them, and the fourth is on its way. And we did it our way.

The Counter-Intuitive Truth About Goals

I’ve been writing my goals down now for 40 years. And I want to share the most important thing that I learned. And if you take nothing else from today, I want you to take a picture mentally or physically of this, which is you will have a higher probability of achieving an aspirational goal that you’re excited about than you will of a more moderate goal.

There’s a reason for this. It’s because you will show up differently. You will assume the identity of someone capable of achieving that goal. You will crowd out unnecessary distractions. You will attract different people on your journey. And most importantly, you will stay with it a lot longer. Ironically, when you think you’re playing it safe by setting a more modest goal, you actually have a lower chance of hitting that goal.

I want to just address one thing. I think because I post a lot on social media about setting goals, on my feed, I get all these people talking about manifesting. I don’t know if you get that on your feed or not, but I do. And these people will say things like, close your eyes and say “money comes freely and easily to me” and then they’re going to see dollar bills everywhere and money’s just going to start. And I’m just like, I don’t know what these people are talking about. This is not what I’m saying for the avoidance of doubt.

What I am saying is have a North Star in your life that gets you out of bed. Have something that is your definite purpose that you’re excited about that is where you’re aligning your calendar and your goals and your emotional energy toward. Have something like that that you’re excited about in your lifetime and you’ll see your energy aligned behind it.

If you want to play a winnable game, choose a goal that stirs your blood.

Step Two: Design Your Own Game

Step two is design your own game. So we, by the way, for the avoidance of doubt, when we set that goal of five, we had absolutely no idea how we were going to do it. But we did know one thing, which is there’s no way we were going to hit that by doing what everyone else was doing. So we needed to design our own game.

The crowded path that is clearly marked is almost never where you’re going to find your winnable game. And yet the world will conspire to have you play exactly this game because it’s crowded and well lit and clearly marked.

If you think of the people that you admire, authors, musicians, poets, entrepreneurs, what you’ll notice if you look carefully is they all played their own game. They found a game no one else was playing. And in doing so, they lived into who they were. And that’s what I’m going to invite all of you to do.

Most games you’ll find have very few rules. When we started thinking about the rules, we thought, of rules in private equity, there’s all these conventions, all these things, you back existing management, you do this, you sell the company, you hold it, and none of that was actually true. It turned out we only came up with three rules,

which is investors give us money, we have to give them money back at some point, hopefully more than they gave us, and in between we wanted to act ethically and according to our values, and those are the only three rules that we came up with. All the rest was just conventional wisdom.

So we started asking some questions to try to unearth places that no one else was looking. We wanted to find diamonds in the rough. So here’s some questions we came up with. What do customers hate about this industry or experience? And there were a lot of things on that list. What are your competitors unwilling to do? What’s a problem that breaks your heart? What assumptions are you making? And finally, what do you believe to be true that not that many people agree with you on?

And when we started unearthing these questions, we found all kinds of diamonds. We found green shoots everywhere that were of places that no one else was looking. And then we came up with our most powerful question of all, which is what are your bright spots? What’s going well?

So we are all loss averse and we tend to look at what’s broken and want to fix it. We look at our weaknesses and want to correct them, but the real magic is not in any of that. Probably 90% of all the great things we’ve done at Alpine have come from scaling the things that are working.

So we looked at our portfolio and we said, well, what’s working? And we cut the data every way we would imagine, growth rate, leverage, all this stuff. And the only thing we could find, our three best deals had seemingly nothing in common except one thing, which is that they happened to have gone so poorly that we took someone from our own team and put them in to run the company or someone from our network. And those ended up being our best companies.

By the way, they were also the most fun because we’re sitting in the board meeting with someone that we had put in and we’re together, we’re at the same values and we’re talking about how we’re going to build this incredible business. So it was not only our best deals, but it was also the most fun.

So we said to ourselves, what if we just did that? What if we backed our own teams every time? And then we get this flood of conventional wisdom, you shouldn’t change management, it’s hard. By the way, we don’t have management, we don’t know how to source deals. And so we kind of like let it go. We said, well, we can’t really do that.

And then the realization we had was, that’s the work. You know, that’s the work. The work isn’t to play the game everyone else is playing only better, faster, harder. The work is in using your creativity to create the capabilities to play the game you really want to play. And so we spent a lot of time on that.

And then when we started doing that, we realized the world needed this too. 80% of companies didn’t have a succession plan for management, so they needed someone to come in and run those businesses. When you can find the intersection of a problem that needs to be solved and a place that gives you energy, that’s where you’re going to find your edge. And some might even call this your purpose.

But this takes a little while and you have to look for this and you have to spend time on it. We spent a full day a week outside the office for about six months to come up with this idea. If you want to play a winnable game, choose a game that stirs your blood and design your own game.

Step three is play the game with people you admire

My first job on Wall Street, I had this boss and I will just to protect his name, I’ll call him Larry. And one Saturday night, it’s 8:30 p.m. and I’m working on a financial model. By the way, it’s a financial model for a company we didn’t own for a deal we were never going to do for a vice president who didn’t ask for it. Probably you all have worked on something like that.

So it’s 8:30 at night, I’m working on this. Larry is standing about three inches behind me and he’s barking out commands. I mean, “Go ahead, make that line thicker. Make that column narrower. Helvetica font, how many times have I told you?” You know, and this is literally the relationship that this is our date night on Saturday nights.

And I put up with this, you know, this is kind of our normal thing, except this particular night, I was really bummed because my mom was in town. And my mom and I are really close and she had driven out from Perrysburg, Ohio and she was a single mom at the time. And she had picked out some restaurants that she wanted to hang out with. And I’m picturing her being at one of those restaurants while I’m making lines thicker for Larry. So it was not a great evening.

Fast forward to the end of that year and it’s time for bonus. Larry completely dings me on my bonus. Like he gives me like a 25% haircut. And I said, “Larry, what the heck? You know, I worked so many hours. I worked 80, 90, 100 hours. I did everything that you ever asked.”

He said, “Well, you know, Graham, it wasn’t really your work. It wasn’t your hours. You know, those were all fine. It was, I just wanted to send you a message. You know, I wanted you to be hungrier. Because if you were hungry, you wouldn’t have asked to leave during an analysis to go have dinner with your mom.”

So that was my first experience out of work. That was my first year.

So fast forward to starting Alpine. And around the time I started Alpine, I also had my first son, Chase. And so two years in, Chase is two. And I don’t really know how to be a dad or how to, I was just a new dad and a new founder.

So anyway, my wife would take Chase to this program called Side by Side. And it’s like pre, pre, pre, pre-K. I mean, he’s two years old. Agenda’s like snack time, story time, recess. And she’s like, “Graham, you have to do this. It’s so much fun. It’s the cutest thing ever. You’ve got to come.” And like, at this point, I don’t know what I’m supposed to do. Like, am I, do you take time off work to go to do this in the middle of the day? Like, I’m trying to figure all this out, right? I’m a new dad.

So on Monday, so Side by Side was on Tuesday. So on Monday, we have our partner meeting with all the partners at Alpine. And we get through all of our business, whatever. And we have like 15 minutes at the end. And I’m kind of like poking around to see like what’s going to happen. So I’m like, “Hell, you know, there’s this thing. It’s Side by Side. It’s tomorrow. You know, they let dads go.” And I’m kind of like testing the waters. And I’m really nervous about doing this because I have some scar tissue from Larry.

And my partner, Billy, just interrupts me. And he says, “Graham, you mean they let dads go? That’s awesome. Yeah, I’ll take your meetings. Like, yeah, that’ll be so much fun. You’ll send me pictures. I can’t wait to hear all about it.”

And I just remember this wave of like relief just came over me because I’m like, I don’t know how I’m going to navigate all this stuff, but I know who I’m going to do it with. And I know I’m going to do it with people that really care about me as a person. And it’s been the most amazing journey ever.

And Billy would go on to have kids of his own and coach them and travel around the country with his kids playing sports. I would get to go to all my music recitals of my kids and parent-teacher conferences. I took all three of my kids to side-by-side and went to lots of sporting events. And it’s just been an amazing journey. And my two boys are in college now, so I don’t have as many of those opportunities. But I wouldn’t have traded, there’s nothing I would trade for those opportunities.

I look back sometimes and I think to myself, what would that conversation on Monday have been like with Larry? How would that have gone? And I can say how it

would have gone, which is I never would have had it. Instead, I would have just played through and I would have worn it as a badge of honor that I could just play through these things that were going on in my life and prioritize work. And the reason that I know that is because I stayed on Wall Street for two more years after that. And I played through. My mom didn’t come to visit again in the next two years, so I didn’t ask for time off to go see her. My girlfriend had a promotion and her roommate threw her a surprise party. I played through. I had multiple friends of mine have big birthday parties and I played through, I didn’t go to those. And I even missed two of my best friend’s weddings. So life would have been a lot different had I aligned my life with people that had very different values than I did.

That’s not the worst part. The scariest part is I started to become leery. And I wonder if I had stayed on Wall Street for another year or two, if I would have been the associate telling an analyst that they couldn’t have dinner with their mom when she came to town. The people in your life will shape your goals, your values, and ultimately your identity. So choose the people with whom you share your life very carefully. If you want to play a winnable game, choose a game that stirs your blood. Design your own game and play with people you admire.

Play Now: The Greatest Trick

My final point is play now. The greatest trick the devil ever pulled is convincing you your life will start when. And I know many of you having lunch and coffees with you say very similar things to that I say all the time, which is my life will start when, I’ll do this when, when I finally pay off my business school loans, when I finally get this promotion, when I get this new job, when I’m actually in the right job, when I have the right relationship, when I have kids, when my kids are older, when I pay off my mortgage, when, when, when, when. And for a long time, I always thought that there was something to be gotten through before my life was really going to start. And what I’ve realized is those things that you’re getting through, that is your life. And your life starts now and it starts in those things.

The two most dangerous words that students say and I hear them all the time are, “Graham, I have this thing I really want to do, I’m excited about it, just,” they never say, no, in 22 years, no student has ever said I’m not going to do it, they say “not now.” Winnable games aren’t found, they’re designed and you never know where you’re going to find them. I never thought I would find my meaning and purpose in a private, running a private equity firm. So you don’t know where you’re going to find it, so you might as well start looking for it right now. You don’t need to start your own firm to start trying to design your own winnable game.

But I can tell you where you’re not going to find your winnable game. You’re not going to find it on the sidelines. You’re not going to find it by being half in and half out. You’re not going to find it by, waiting around for life to really start and being hedged. If you’re not careful, you can spend your whole life there. And you’re going to find your passion by being passionate about the life that you’re in right now, no matter what the situation is.

The Four Steps to Designing a Winnable Game

So what I shared with you today are four steps to designing a winnable game. A game where you can combine something that you’re really excited about, something that matters to you, something that you’re really excited about, something that matters to you, a game you can win, and ultimately a game where just playing the game alone allows you to be the person that you really want to be. If you follow these steps and can find that alignment, I think that’s what winning really looks like. So class of 2025, let’s play now.

Now is the time to choose a game that stirs your blood. Ask yourself the question, what would I do if I knew I wouldn’t fail? Ask yourself that often until the answer becomes really clear to you. And then write that down and start moving toward it. And you will assume the identity of someone who’s already achieved that goal. Remember, you will have a higher probability of achieving a goal that you’re excited about than you will have a more moderate goal. And playing big is the real you.

Now is the time to design your game. Realize that most rules aren’t rules at all, they’re just conventional wisdom. And most games really have very few rules. Look for problems that break your heart. Look for places that other people aren’t looking. Scale your bright spots, both your wins and the things that give you energy. When you can combine something that the world needs with something you’re excited about, that’s where you’re really going to light up, that’s where you’re going to find your purpose.

Play the game with people you admire. Find the people who give you energy and share your values and share your life with them and avoid the people who don’t. Your goals and values and ultimately your identity will come from the people with whom you share your life. And I can promise you when you look back, almost every single one of your favorite memories will involve someone that you really care about.

And finally, play now. The two most dangerous words are “not now” and waiting on the sidelines is not where you’re going to find your winnable game. Waiting on the sidelines is just fear in another form. You never know where your winnable game is, so you might as well start looking for it where you are right now. You will find your passion by being passionate about your life that you’re leading.

Conclusion: Your Game Starts Now

Class of 2025, you’re ready. You are enough and the game starts now. What game will you play with this one precious life of yours? Thank you. Thank you. Thank you.

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