Stanford GSB Last Lecture 2025: How to Design and Play a Winnable Game

In June 2025, I delivered a “Last Lecture” to the graduating class of the Stanford Graduate School of Business. You can watch it at the link below or read the summary that follows.

The lowest point of my career was in October 2008. Lehman Brothers had blown up three weeks earlier, and the market was down 40%. One morning, I got a call from the largest investor in Alpine Investors, the private equity firm I’d founded several years earlier. He told me that, given market conditions, he couldn’t invest in the fund we were raising anytime in the foreseeable future. At the end of the call, he said something even scarier — that each of my remaining investors would likely make the same call. His prediction would quickly prove to be right.

That night, I couldn’t sleep. Around 3 a.m., I gave up tossing and turning and went upstairs to my two-week-old daughter’s bedroom, which was doubling as my home office. While Lily slept soundly — she seemed to be taking the collapse of the U.S. housing market in stride — I crunched the numbers to see how long I could fund Alpine’s payroll and pay my mortgage before I blew through our savings.

Twelve months. Not the answer I’d been hoping for. 

As I closed my laptop and looked across the room, I broke down. Lily needed her dad to figure this out, and Dad was not figuring it out. I desperately needed an answer to the question I had been asking myself my whole career, and in many ways, my whole life: “How do I play this game better, faster, and stronger than everyone else?” In that moment, it occurred to me that the right answer eluded me because I’d actually been asking the wrong question. In all my striving, I’d never stopped to ask myself, “Am I even playing the right game?” I knew in my gut the answer was a resounding “No.”

“In all my striving, I’d never stopped to ask myself, ‘Am I even playing the right game?’”

I came to understand that I had not been playing a winnable game. A winnable game is a game you can win — one you’re excited to play, and that brings you closer to who you want to be. It is a game where external success and internal fulfillment are in harmony, not in conflict. Learning to play a winnable game is what led me out of that dark night in 2008, and the actions I took can help you do the same. Here are the four essential steps to designing and playing a winnable game.

Step 1: Choose a Game That Stirs Your Blood

My freshman year of college, I tried out for the rowing team. I’d gone to a public high school in Ohio and had never rowed before. I didn’t even know the boats went backwards! Perhaps unsurprisingly, when they posted the kids who made the boats two weeks into the season, my name wasn’t there.

They told those of us whose names were not on the list that we could still be “land warriors.” We wouldn’t be in the boats, but we could use the boathouse gym and rowing machines. So, the next morning, I showed up at 6 a.m. to beat the rush of other would-be rowers. As it turned out, everyone but me realized “land warrior” was just code for “You got cut.” No one else was there.

After about 15 minutes of working out, someone did come in — not a fellow freshman, but a tall, mustached man who looked about a decade older. Without a word, he sat down a few spots over and started hammering the rowing machine. He rowed each stroke harder than I’d ever seen anyone row before, and he didn't stop for a solid hour.

After a week of early mornings together, this other rower finally gave me a head nod. I responded with the most over-enthusiastic wave you’ve ever seen, which set us back another couple of weeks — but eventually, he got curious enough to ask who I was and what I was doing there.

“I’m Graham,” I said. “I’m a land warrior. Who are you?”

His name was Mike — Mike Teti, as I would later learn. I also learned Mike and I were not training in the same metaphorical boat.  He was already a world class rower and would later go on to row in his third Olympics and coach the 2004 U.S. team to a gold medal. 

I shared with Mike my goal of making the third-string novice freshman lightweight team. Mike said, “Graham, your form is terrible. But if you keep training like that, you’ll make the Olympic team.”

A surge of energy came over me. I didn’t yet know who Mike was, much less whether he was right. But as the architect Daniel Burnham once said, “Make no little plans. They have no magic to stir men's blood.” I knew rowing stirred my blood, and the idea of becoming an Olympian really stirred my blood. 

With this new idea and encouragement, I shifted my goal, and I would later learn, I also shifted my identity. 

Back then, everything I knew about goal-setting was from an audiobook by the author Brian Tracy. He said that every day, you should write down your goal — in present tense — along with what you’d do to move it forward. So, each morning when I woke up, I wrote in a green spiral notebook, “I am an Olympian.” I then wrote the three things I was going to do that day to move toward that goal, and I did those three things. As this habit persisted, a funny thing started to happen. A part of me assumed the identity of someone who had already achieved that goal; my subconscious started to believe it. And each time I took a related step — working out, lifting weights, or eating right — I assumed that identity a little more.

“As I wrote ‘I am an Olympian’ in my little green notebook, a funny thing happened: A part of me started to assume the identity of someone who had already achieved that goal. I started to believe it.”

My path over the next four years wasn’t easy. I lost more seat races than I won, and I didn’t even make the boat I wanted my freshman, sophomore, or junior year. I didn’t continue rowing post-college, so I never tried out for the Olympics. But by my senior year, I was elected captain of what would become a national championship team, and I had one of the fastest 2000-meter erg times in the country. More importantly, I had learned the incredible power of setting a goal that stirred my blood. 

So, that night in my daughter’s room in October 2008, I asked myself, “What is Alpine’s goal?” At the time, this was our vision statement:

“Generate attractive, risk-adjusted returns while maximizing the probability of capital preservation.”

Woo! Who’s with me?! So inspirational, right?

It’s funny in retrospect, but actually it happens to all of us and it's terrifying: We have big dreams, and then the world intervenes. We have setbacks and failures, losses and heartbreak. People tell us we can’t do something, and, over time, we sell ourselves short. We lower our bar. We settle. And we wind up setting a goal that we don’t even want to achieve. We play a game we don’t even care to win. 

Remember, though, that your identity flows from your goal. Alpine’s goal was essentially, “try not to lose money.” Just like a part of me assumed the identity of an Olympian, I had assumed the identity of someone intent on holding on tightly and playing small: “We can’t take this risk.” “We can’t make that investment.” 

That was the first problem. The second problem was that we were playing a game we weren’t even excited to win.

We began asking a different question. (Students who have taken any of my classes know this is my all-time favorite question.) We started asking, “What would we do if we knew we wouldn’t fail?”

It took us months to clear away all the doubts, fears, and limiting beliefs to even give ourselves permission to come up with an answer to this question. But eventually, we landed on:

“Be the #1 performing PE firm in the world. Deliver 5x on every fund.”

For context, the top 25% of PE firms in any vintage deliver about 1.8x to 2x; this goal was the equivalent of winning the gold medal. And, given where we were at the time, it was as aspirational as transforming from a 135-pound mullet-sporting land warrior to an Olympian. 

But just like before, a funny thing happened: We started showing up as a team that could achieve that goal. We started attracting a higher caliber of people and investing in better companies. We held the companies longer and were more aggressive in building them. It wasn’t all rainbows and unicorns; people left, too, and we lost money on some deals. But of the four funds we’ve invested since setting that goal, the first three delivered 5x, and the fourth one is well on its way.

If you take nothing else from this post, remember this: You are more likely to achieve an aspirational goal that you’re excited about than a modest one. This is not just a platitude. There are specific reasons for this. You will show up differently when you’re working toward a goal you’re excited about. You will attract people who are excited to go where you’re going. You will crowd out unnecessary distractions and align your energy and calendar more clearly behind your goal. And most importantly, you will stay with it far longer. 

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

Step 2: Design Your Own Game

When Alpine set that 5x goal, we had no idea how we’d achieve it. But we did know one thing: we wouldn’t get there by doing what everyone else did. The crowded, clearly-marked path is rarely where you’ll find your winnable game. And yet, the world will conspire to have you play this game (because it is crowded and clearly marked). The people we admire most — the authors, musicians, poets, entrepreneurs — all found a game no one else was playing. They lived into who they were and played their own game.

The games we play in life have far fewer rules than you might think. In private equity in 2008, everyone bid on the same companies, backed existing management teams, held companies for about the same number of years, and then sold them to the highest bidder. But we recognized that private equity actually had only three essential rules: 1) investors give us money, 2) we give them money back at some point — ideally, more than they gave us, and 3) in the interim period, we act ethically and according to our values. All the other so-called rules were nothing more than conventional wisdom.

“All the other so-called rules were nothing more than conventional wisdom.”

Next, we started asking questions to help us design our own game. “What are our competitors unwilling to do?” “What assumptions are we making?” “What do customers hate about this experience or industry?” “What do we believe that others don’t?” These questions, by definition, led us to places no one else was looking, and we found green shoots everywhere. Then we asked the most powerful question of all: “What are our bright spots?”

Humans are loss-averse; we look for broken things to fix and weaknesses to correct. But the vast majority of Alpine’s accomplishments have come from scaling our bright spots — doubling down on the things that already work.

At first, it wasn’t clear what those bright spots were. We cut the data every which way (industry, purchase multiple, growth rate, etc.), and the only thing our three best deals had in common was that they’d initially gone terribly! They had gone so terribly that, in each case, we’d sent in a member of our own team or network to right the ship, and each time they’d turned things around. These not only became our best companies, but they were the most fun, because everyone on the team was working from shared values toward a shared goal. And we were winning together. 

It was tempting to defer to conventional wisdom, even with this newfound information. At the time, everyone said you shouldn’t change management, and we didn’t have management talent to put in, anyway. On top of that, investment banks only sold companies that came with management teams, so we also had no deal flow sources for companies without management teams. But then it hit us: That is the work. Building a sourcing engine to find these deals, and building a pipeline of talented leaders to run these companies  — that is the work. We needed to use our creativity to design a system to play the game we wanted to play, not just work harder to play someone else’s game. 

We started building a plan to source new companies and back our own teams in every new deal. It took months — we dedicated a full day per week outside the office to working on the idea. Carving out all this time away from the day-to-day was tough. But it worked. And it wasn’t just good for Alpine, it was solving a problem that the world really needed someone to solve. Most small companies in the US have no succession plan, so we offered a liquidity and succession solution for those owners. They needed someone to step in to run their companies. 

The intersection of a problem that the world needs solved with the thing that gives you the most energy — that is where you will find your edge. And some might even call this your purpose. 

If you want to play a winnable game, 1) choose a goal that stirs your blood and 2) design your own game.

“The intersection of a problem that the world needs solved with the thing that gives you the most energy — that is where you will find your edge. And some might even call this your purpose. ”

Step 3: Play Your Game With People You Admire

In my first job on Wall Street, I spent most Saturday nights with my boss, whom I’ll call Larry. At 8:30 p.m., you’d find me hard at work on a financial model of some company we didn’t own, for some deal we were never going to do, with Larry standing three inches behind me, barking out commands. I’d mostly accepted our late nights, resigned to the industry status quo. But one weekend in particular, my mom had driven nine hours from Ohio to visit me in NYC, and I asked Larry if he could spare me for a couple of hours to take her out to dinner. He said no, and I stayed at the office, making this column narrower and changing that font from Times New Roman to Helvetica.

At the end of the year, Larry gave me a 25% haircut on my bonus. I asked why: I’d worked 80, 90, 100 hours per week. I’d done everything he asked. He told me it wasn’t my work or my hours. He just thought I wasn’t “hungry” enough. He said someone who was hungry wouldn’t have asked to have dinner with his mom in the middle of an analysis. 

Fast forward to 2005, when my new company, Alpine, and my first son, Chase, were both a couple of years old. My wife had been taking Chase to a Pre-K program called Side by Side. It was, she promised, “The cutest thing ever. You have to come.”

I was both a new dad and a new founder. I had no idea what to do. Could I really take time off work for this? The Monday before the next Side by Side, at the end of our partner meeting, I nervously tested the waters. I started describing Side by Side to my partners, too afraid to ask for the time off. 

My partner, Billy, quickly interrupted me: “Graham, that sounds awesome! I’ll take your meetings. Send pictures. Can’t wait to hear all about it.”

A wave of relief came over me. I still didn’t know exactly how I was going to navigate work and fatherhood, but I knew I was going to do it with people who cared about me. Billy went on to have kids of his own; he coached them and took them around the country playing sports. I took all three of our kids — Chase, Lily, and Blake — to Side by Side; was home almost every night for dinner; and went to their music recitals, sporting events, and parent-teacher conferences. My boys are both in college now, and I wouldn’t trade those moments with them for anything in the world.

“I still didn’t know exactly how I was going to navigate work and fatherhood, but I knew I was going to do it with people who cared about me.”

I often reflected on what that Monday conversation at the end of that partner meeting would have been like with Larry. And I know the answer: It never would have happened. I would have put work first and worn it as a badge of honor. I know this because, after that bonus conversation with Larry, I stayed on Wall Street for two years. Not wanting to get dinged on my bonus again, I played through. I didn’t ask for time off to see my mom again because I didn’t invite her to visit me. I played through my girlfriend’s surprise party for her promotion. I missed several of my friends’ birthday parties and even two of my closest friends’ weddings. 

That’s not the worst part. The worst part is, I started to become Larry. I think that if I had stayed on Wall Street much longer, I might even have become the associate telling the analyst they couldn’t have dinner with their mom when she came to visit. My entire life would have been different. 

Listen to that voice inside you when it tells you something isn’t right. Over time, I learned that you become the people with whom you share your life. The people you surround yourself with shape your goals, your values, and, ultimately, your identity. Choose them wisely.

If you want to play a winnable game, 1) choose a goal that stirs your blood, 2) design your own game, and 3) play the game with people you admire.

Step 4: Play Now

The greatest trick the devil ever pulled was convincing you life will start “when.” When you pay off your student loans, when you find the right job, when you’re married, when the kids are older, when, when, when, when, when. I spent a lot of time thinking about the things I needed to get through before life got started, before realizing those things I was trying to “get through” were my life.

In 22 years of teaching at Stanford, I’ve never heard a student say, “There’s something I’m excited about, but I’m never going to do it.” Instead, they say the two most dangerous words: “Not now.”

But here’s the thing about winnable games: you don’t always know where you’ll find them. I never thought I’d find my purpose running a private equity firm. So, you might as well start looking where you are. Because I can assure you of one thing: you’re not going to find your game by standing on the sidelines. You’re not going to find it by hedging. You’re not going to find it by being half in and half out. And if you’re not careful, you will spend your whole life in that place — waiting for the perfect moment, which, of course, never arrives. 

“You’re not going to find your game by standing on the sidelines.”

“Not now” is just fear in another form. Resist the temptation to need the perfect situation to start your life. You are only going to find your passion by being passionate about the life you have right now.

If you want to play a winnable game, 1) choose a goal that stirs your blood, 2) design your own game, 3) play the game with people you admire, and 4) play now.

When you design and play a winnable game, you get to follow your energy and do something that matters to you. Just by playing the game, you get to be the person you want to be. So go figure out what stirs your blood. Design a game that combines that excitement with something the world needs. Play your game with people who light you up and share your values, and steer clear of the people who don’t. And start looking for your game right where you are — today.  If you follow these steps and find that alignment, that’s what winning really looks like. Playing big is the real you. You’re ready. You are enough. And the game starts now.