Last Lecture Series: “How to Live an Asymmetric Life,” Graham Weaver

When working in a role that is not your authentic passion (private equity), even when executing successfully (early flights, bidding on businesses, full commitment), you are sacrificing personal life (time with family) without generating genuine engagement or fulfillment.

“I got on early flights you know would start bidding on businesses and they'd tell me which companies to go to and I would do those and I would I would throw I threw myself in with everything that I had and if I had kids at the time I would have been home late and I would have you know missed Little League games”

The industry, market, and competitors did not change during the transformation; only the company and its story changed. This demonstrates that writing your story and aligning to it produces material results, not through mystical 'universe response' but through measurable changes in alignment, goal-setting, and team attraction.

“by the way what didn't the industry didn't change the market didn't change our competitors didn't change we changed we just changed our story that's all we did we changed our story you know don't write a story about what happens write your story and then make it happen and there's so much magic in this you you put out the thing in the universe that you want to happen and the universe responds and it does and that sounds like woo woo you're like oh God here we go Universe responds but what what what's really happening what's really happening is you're putting on blinders to where you want to go you're making goals you're aligning your day to where you want to go you're attracting people that want to go to the same place that you want to go so it is the universe but it's actually there's some mechanics behind it too that make it happen”

The analogy between risk-averse dating and risk-averse investing: keeping emotional distance ('one foot in, one foot out') to avoid heartbreak paradoxically guarantees the outcome you're trying to avoid, and guarantees that even good outcomes won't be satisfying.

“it's kind of like imagine your imagine you're you start dating and your only purpose of dating is not get your heartbroken and you're going to have one foot in and one foot out and even if you have a even if you have a good date it's not going to be that great because you're not really in it but the more likely outcome is you're going to guarantee the very outcome you're trying to avoid which is you're going to get your heartbroken”

Any meaningful change (hard conversation in a relationship, career change, starting new habits) initially makes life worse. The largest cost of this 'worse first' phase is psychological fear, not objective difficulty. As you repeat hard things, the fear component shrinks, making subsequent changes easier.

“your life is almost always going to get worse for first any change that you want to make is almost always going to get worse first so you're in a relationship and you have to have a hard conversation that particular night your life is going to get a little worse and then you're going to come out the other and it's going to get better... but you need to realize that the thing that's keeping you there is the first move is always going to be worse and eventually you're going to eventually what's going to happen is these these uh downward curves are going to get a lot shallower because you know what the biggest part of that curve is it's just fear the biggest part of that curve is just fear”

Principle Three is 'do it for decades.' The speaker's peers at his time of graduation (early 2000s) thought trading meme stocks or day trading NFTs would outperform sustained business building. The speaker's advantage was willingness to compound returns over 20+ years; most people underestimate the power of n (time period) relative to r (rate of return).

“if you think of the equation for returns it's 1 plus r to the n n is quadratic n is the number of years you you you compound that's the most powerful part of the equation is n and and so if you think of me my rate of growth it almost doesn't matter I'm growing every year year three I'm a better CEO than I was in year two and in year five I'm better than I was in year four but you're 23 I'm in you're 23 and if you if you take that R which is how how fast you're improving and you can work on that r a little bit Executive coaching and writing out your goals and meditating and trying to work and be good at your job and now you put a 23 on it you can be the best in the world”

After the realization on the plane, the speaker decided: 'I'm going to play for the upside. I'm just going to go big.' He made a decision that he would never again say 'not me' or 'not now'—these words are now banned from his vocabulary.

“and like there's really ultimately there's no way to totally protect against loss or downside and so I said from this point on I'm going to play for the upside I'm just going to go big and from that point on I did I made a decision right then that I was never again in my life going to say not me or not now I was never going to say those words again so I landed I ended my relationship uh that night the next day I walked in and handed in my resignation at my firm”

The only question you need to answer is: Are you going to give yourself permission to lead/live that life? This question recurs throughout life, and the answer you give determines whether you live your asymmetric life.

“there's really only one question you need to answer which is are you going to give yourself permission to lead that life to live that life and to let that out that's a question you're going to answer over and over and over in your life from now on are you going to give yourself permission it's permission you need”

The speaker initially operated under the principle 'Rule One: don't lose money, Rule Two: never forget Rule One,' which caused him to play defensively, buy undervalued assets, and ultimately underperform—including three instances where he wrote investment memos claiming mathematical impossibility of loss but still lost money.

“what I thought I knew at the time was rule one don't lose money and Rule two never forget rule one so I spent all that time I spent all that time just playing for like playing small like just trying to protect my downside trying not to lose really hard so we bought businesses like at a discount to their net asset value and even when things went right it didn't go that right but there were three times I wrote literally an investment memo that it is mathematically impossible to lose money on this investment and we lost money all three times”

Great investing can be summarized in a single word: asymmetry. The goal is the biggest possible outcome relative to your downside risk (typically losing one times your money), achieved by stacking multiple criteria logarithmically rather than linearly to create 10x, 20x, 50x, or 100x return potential.

“in 30 years of being a professional investor I can summarize great investing in a single word which is asymmetry and you are looking for the biggest possible outcome relative to your risk and your risk typically is just losing one times your money that's all you're going to lose so you want to be stacking criteria on top of each other where it becomes asymmetric so for example if you have the criteria of an amazing management team that is going to work super hard and hire well and they're going to be in this industry that's got infinite capacity they redeploy Capital at high rates of return and and and and you can hold it for 10 years and they want to keep going and you stack those on top of each other they don't stack linearly they stock they stack logarithmically and and you can have an almost infinite outcome”

In rowing, completing a 2,000-meter erg test (the measure of fitness and boat placement) requires pushing until you cannot pull another stroke. The training process involves months of conditioning, but the first two weeks produce half the annual improvement (10 of 20 seconds) despite minimal physical change, coming entirely from increased comfort with discomfort.

“throughout the course of the the season like the day that I'd show up which would be like September 1st from that date all the way through March I would improve my urg time by 20 seconds roughly from the first day with all conditioning everything we do but so a big part of that would be rowing stadium stairs uh L lifting weights and on and on it was grueling and it was it was a lot but all that stuff I just said would take about six months and only 10 seconds of that 20 would come from that the other 10 seconds would come in the first 2 weeks you're like what so what happened in the first two weeks to give you 10 seconds I'll tell you what didn't happen you didn't change your cardiovascular fitness you didn't change your strength you didn't change your v2x or your Technique all you changed is your comfort to be uncomfortable”

At a dinner with other private equity professionals, the speaker's peer 'Dave' was enthusiastically discussing deal mechanics and debt covenants while the speaker felt no connection to the content. The speaker realized that Dave was living his own passion ('colonizing Mars'), while the speaker was performing someone else's dream and therefore would lose to Dave despite equal effort.

“Dave starts going off Dave is like I just won this deal you won't believe this here's what happened there was this debt this is what we did on the debt covenants... and he's going on and on and on and I'm thinking Dave thinks he's colonizing Mars you know he's so excited about this like he's in his head you know he's colonizing Mars and I'm thinking to myself two things I'm thinking first Dave is going to kick my ass because I don't care at all about any of this stuff and and the other thing I realized is that this is what Dave had written his business school essay about he was living it he was doing the thing that he wanted to be doing and what what you're you're not you're not going to win doing someone else's dream you can survive for a little while but you're not going to win”

The speaker's immediate response to the ambitious story was skepticism: 'that was aspirational' (meaning: no way that's going to happen). The coach replied that the first step was simply to hire a CEO, and that 2008 (a recession) was actually a good time to attract top CEO talent.

“and I was like and that was really fun and then I started saying well that that was great you know you know but that that there's no way we're going to do that like it it was just so aspirational aspirational by the way is a euphemism for how the hell we going to do no way that's going to happen it was it was aspirational so he's like well what's the first step first step is hire a CEO it turns out in 2008 a recession that's a pretty good time to hire a CEO”

When making a choice between two paths with uncertain outcomes (expected value calculation), most people fail to factor 'you' into the equation—specifically, whether you are 'turned on' (excited, energized, intrinsically motivated) by the work. This variable is asymmetric in importance but invisible in typical decision analysis.

“the other thing you're missing in this equation of your is is you're going to do an expected value calculation right but there's one thing you're not factoring into that equation which is you're not factoring in you when you're turned on”

Executive coach JP Fulm taught the speaker Principle Four through a structured exercise: write a story about the company's status five years in the future, following three rules: (1) set it 5 years out to escape the fog of war and current crisis; (2) start with 'Nirvana'—the best-case scenario, not something mediocre; (3) forget about the 'how' for now, focus on the dream.

“he's like all right here's what we're going to do we're going to write a story okay and there's three rules to writing this story the first one is it's going to take place five years from now we're going to get out of the fog of warri you're right you can't you can't look past where you are six Ines in front of your face let's go out five years the second rule is let's start with Nirvana I don't want to hear something that's mediocre I want to hear what would happen what would you do if you would knew would not fail what would be your genie goal as as Logan said and third he said the how is the killer of all great dreams forget the how I don't care about the how right now I just want to hear about the dream”

The biggest obstacle most people will face in their lives is fear. Fear disguises itself as practicality ('I'm being practical'), helpfulness ('I'm helping you'), or self-protection ('I'm saving you'), and most dangerously, it disguises itself as 'not me, not now.'

“the biggest thing that you're going to face um as you graduate for most of you and through your lives like the biggest obstacle you really have is going to be fear if you really boil it down and fear is very very manipulative and it shows up in all these kinds of different ways and it tries to disguise itself okay it disguises itself as being practical I'm being practical right now it disguises itself as I'm helping you it disguises itself as I'm saving you and most of all it disguises itself as not me not now”

The speaker lost 50% of his largest investor's personal capital early in his fund management career, which was devastating because the investor had backed him based on belief in him as a person, not track record.

“I tell Joe that his investment in my firm is down 50% he's lost half his money and it wasn't his firm's money it was his personal money and I can just see the energy drain out of him”

After the 2008 experience, the speaker and Alpine began writing stories about everything: becoming CEOs, building cultures where people want to spend whole careers, sourcing strategies. The speaker claims that 'pretty much every single thing we ever wrote came true from that point on.'

“after that experience this I was like on to something I was like this is Magic pure magic we started writing stories Alpine about everything we wrote stories about how we could have NBAs become CEOs right when they graduate we wrote stories about building cultures where people would want to spend their whole careers where where people could feel like they mattered and feel like they're their their life you know had meaning and that they were contributing we wrote stories about companies we wrote stories about sourcing and just pretty much every single thing we ever wrote came true from that point on”

Weaver realized that his 30-year evolution from downside-focused investing to asymmetry-focused investing mirrored his personal life, where he was 'playing small' and 'playing not to lose' rather than optimizing for upside in relationships, career choices, and personal growth.

“as I started realizing that this was how I was living my life invest invest thing it also was how I was living my personal life and I was just playing small I was playing not to lose I was just trying to just trying not to lose”

Principle Two is 'do your thing.' The speaker had a choice between joining a large private equity firm (clear path, salary, bonus) and pursuing an entrepreneurial label-printing venture with uncertain outcomes. He chose the firm, and this was a mistake.

“when I graduated from school probably like many of you I had a choice to make there were two basically two options there was uh there was a firm that came to recruit on campus and I knew I could do it is what I did before business school it was a big private Equity Firm there was a a number of my classmates went with me there was a salary and a bonus and free lunches and it was it was really clear and then there was there was another path which is i' done these as L Logan I started doing this crazy stuff in business school with buying companies on my credit cards... so so I chose I chose uh the path of of going to the big firm”

The speaker spent six months finding and hiring Mark Stout as CEO. Mark became a great friend and later partner at Alpine. After 18 months, Mark and his team won every single contract that came up in that business for the next two years except one, and began to dominate competitors.

“we spent six months and we brought on the best CEO his name is Mark Stout he's been and he he's a great friend of mine now he's a partner at Alpine now and so we brought him on we started doing exactly what we talked about we started building the team we started building the technology we had better up time and then when Mark and his team got going after 18 months we won every single contract that came up in that business for the next two years except one and we just started stomping on our competitors”

The speaker recently met with his original investor Joe, 20-23 years after the initial loss story. Joe had left the hedge fund to work on climate change and was visibly excited about that work. Joe graciously acknowledged that the speaker's Alpine fund had performed well, and thanked the speaker.

“I had the privilege of meeting with Joe very recently from the very first story I told you and this Joe Joe this is 20 20 year 20 years after the first story I told you ande Jo stayed I didn't tell you what Joe Joe was incredibly gracious I could tell how hard it was for him to do that but he was gracious because he too had had some struggles in her in her his early days and he understood that things take time and that they're hard so he stayed with us and he was a supporter of us for for the last 20 years so Joe left the hedge fund and and he devoted his life to climate change so we sit down we and we had an hour meeting we spend the first 55 minutes hearing all about climate change and all the stuff he's working on he's just bouncing off the walls he's so excited he was doing his thing and then as we do every single time that we meet you know I give him our Our Deck and our performance sheet and Joe's been a big investor of ours and you know his foundation that does climate change is is our investor and he looks at this sheet and he uh and he just he just looked at me and he just said you know go Grand you did it you did it you know 20 23 years later like this is amazing he said thank you”

The speaker has had the privilege multiple times of hearing from college endowments and university boards that Alpine's investments have funded 10+ years of financial aid or major building projects. Similarly, investors running cancer foundations and climate change work have also benefited.

“I have the privilege of having this meeting over and over and I meet with college endowments and boards that are like that that will say literally like you've helped us fund 10 years of financial aid for our school or another another University like shows us that this is going to go a huge part of the budget toward the buildings that they're building or you know we have investors that are running cancer foundations and are doing uh climate change work and it's it's been it's been a long ride but a really glorious one”

The speaker's life changed dramatically after learning that his friend Monty from his rowing team was killed in a plane crash at age 23. This event shattered his ability to remain emotionally distant and forced a reckoning with his life choices.

“my friend calls me on the phone and says you know hey sit you need to sit down which nothing ever good comes of of that first intro and a phone call and he says hey your friend you know Mon's gone um he he was killed in a plane crash he was 23 and uh I I was just like I couldn't even process this information I was just like it it just couldn't register I I I was just devastated but also I was kind of like just not dealing with it”

The four principles (do hard things, do your thing, do it for decades, write your story) are 'the antidote to fear' and provide tangible, tactical ways to 'look fear in the eye and say to fear: not today.'

“what I have given you today is the antidote to fear that's been my goal the four things that we talked about are ways that you can tangibly and tactically throughout your lives look fear in the eye and say to fear not today today I'm going to play Big today I'm going to play for this asymmetric life”

Write your own story. No matter where you're starting or what role you have after school, you can start today writing your story. You have magic, you have your own life, you have something special for you.

“finally write your own story no matter where you're starting and no matter what your role you have after school or where where you are right now it doesn't matter you can start today writing your story inside of you you have you have a you have magic you have your own life you have something that's special for you”

You are graduating from Stanford Business School. You did not come this far to play small. You came this far to move the world. Now is the time.

“you're about to graduate from Stanford freaking business school Stanford freaking business school you did not come this far to play small you came this far to move the world now is the time now is your time”

Principle One of an asymmetric life is 'do hard things.' Life comfort (ease of consumption and entertainment) produces only short-term dopamine hits and is not the path to happiness or fulfillment.

“principle one is do hard things so we have this view we have this thought that life is supposed to be easy and that there's and that and that Comfort is where we're going to gain uh happiness so you can order Harmony Bowl from sweet Greens on your on your app you can you can you can Bing binge watch succession and Ted lasso and you can have you can have you can have a life of ease and and and that will give you a quick hit of dopamine but make no mistake that is not the path it is exactly the opposite”

In 2008, during the financial crisis, the speaker's company Alpine was flattened: unable to raise funds for 5 years, savings drained to meet payroll, and seven companies in default (including the largest). The speaker hired an executive coach, JP Fulm, at great financial cost to himself during this crisis.

“in 2008 we had just started we finally got going at Alpine things are start you know we're starting to get going and Bam we just got flattened by the recession I mean flattened we were not well positioned it turned out we wouldn't raise a fund for 5 years drain my savings account to make payroll we had seven companies in default including our largest business was in default at the time”

Immediately after the realization on the plane, the speaker ended his relationship that night, resigned from his private equity firm the next day (leaving behind the salary, bonus, and equity), and drove to Steamboat Springs, Colorado to be with his ex-high school girlfriend Cindy, who is now his wife of 21 years.

“so I landed I ended my relationship uh that night the next day I walked in and handed in my resignation at my firm that I'd been working at left my crude equity and bonus and everything didn't have any come coming in and then few days later I packed up my car and drove out to Steamboat Springs Colorado where my ex high school girlfriend Cindy was living who's now who's here and my wife of 21 years”

Years after Monty's death, the speaker had dinner with rowing colleagues in New York. They talked all night about Monty, stories, and processed their grief together—something none of them had adequately done before. This cathartic experience was necessary for each of them.

“so long I go with my life year after year and as I said I worked at this firm and a little bit of me was you know I was that that Dreamweaver character that that Monty had found in me was was nowhere to be seen and so around that time right at right as I was in this large private firm I flew out to New York and I ended up having dinner with a bunch of uh our colleagues who who had rode crew with Monty and we ended up talking all night and I think all of us kind of needed a process uh what you know what had happened and none of us had really done that and uh so we start talking all night and and we were drinking and we're telling stories about Monty and this went on pretty much all through the night and it was awesome we needed it you know we needed to we needed basically to kind of clear this out and and and deal with the this LW that we had”

Monty Raeser was a rower and friend of the speaker in college. He gave the speaker the nickname 'Dream Weaver' (combining the speaker's last name Weaver with the concept of dreams), which represented the person Monty saw in the speaker at the time.

“so I rode crew in college and uh as I mentioned before and uh I I had a nickname in in rowing which was Dream Weaver and my last name is Weaver and so my friends call me Dream Weaver and like what a great name right cuz I mean like who doesn't want to be Dream Weaver so the person who gave me this name was a guy named Monty Razer and my sophomore year he was a senior”

Weaver advises that there is 'something you fear right now that's exactly where you should go' and that things people are 'putting off right now' are the 'thing' they should be doing, because 'everything that you want is on the other side of worse first.'

“now is the time to do hard things there's something that you fear right now that's exactly where you should go you should be doing that thing there's something you're putting off right now you should be doing that thing everything that you want is on the other side of worse first”

There is no obstacle that will not yield to sustained excitement about something for a decade or longer. This is the most powerful statement the speaker can make about the 'do it for decades' principle.

“there is no obstacle that will not yield to you excited about something for a decade or longer if you want to have an asymmetric life do hard things do your thing and do it for decades”

On the flight home to San Francisco from the dinner with rowing colleagues, the speaker had an emotional breakdown (crying hysterically for 3 hours). Afterward, sitting back down, he realized that Monty would be disappointed in him: the Dreamweaver character Monty had seen in him had vanished while the speaker played it safe.

“and I just lose it you know I'm in one of these huge planes going from San Francisco to New York and it has two seats and then five seats and then two seats and I'm not right in the middle I'm like one over but in the middle and I'm just balling hysterically and like people on both sides of me are like trying to help me and tell me if I'm okay and the flight attendant keeps bringing me water... finally I kind of get my act together and I'm go to the you know splash some water in the bathroom it's like 3 hours now into the flight and I sit back down at this point and I just remember thinking to myself so I sit back down and and like I close my eyes and I can kind of still see that visual where Monty says dream when I walk into the you know the the uh locker room and I just remember thinking Monty would be so disappointed in me right now like I'm so far from this person that he thought I was this Dreamweaver like I'm I haven't seen that person in years”

In the 20 years since the plane flight, the speaker has never again said 'not me' or 'not now.' This commitment has had amazing consequences, though he acknowledges it has not been easy.

“in 20 in 203 years years since that plane flight I've never I've never once again I've never said again not me not now never and it's been amazing and it hasn't been easy as I've as we talked about”

You cannot win while doing someone else's dream; you can survive for a short period but you will not achieve asymmetric success.

“what what you're you're not you're not going to win doing someone else's dream you can survive for a little while but you're not going to win if you want to live an asymmetric life do hard things and do your thing”

When you ignore the 'how' and write an aspirational story with full permission to dream, you can pick anything you want; this is inherently a fun exercise that removes the weight of feasibility.

“turns out with those three rules it's pretty fun exercise I get to say ex I get to go out five years I don't have to worry about how I'm going to do it and I get to pick anything I want like that who doesn't want to do that”

You should be doing your thing (your authentic passion); there is suffering either way, so pick something worth suffering for and realize you are underestimating your power when you're excited about something.

“now is the time to do your thing there is suffering you will suffer so pick something worth suffering for and realize that you are underestimating yourself at your full power when you're excited about something that's not going into your equation”

At the private equity firm, Weaver's boss provided explicit career goals (becoming vice president) that Weaver then pursued aggressively by working early flights, bidding on assigned businesses, and throwing himself in completely, which would have meant missing family time if he had children at the time.

“my boss is like here's what you need to do to be vice president you know here's your gold post so I'm gonna like Sprint like hell to those gold post as fast as I can...I got on early flights you know would start bidding on businesses and they'd tell me which companies to go to and I would do those and I would I would throw I threw myself in with everything that I had and if I had kids at the time I would have been home late and I would have you know missed Little League games”

Reflecting on the dinner conversation with Dave (who was excited about debt optimization), Weaver notes that while Dave thought Weaver was 'buying these stupid label printing companies and thinks he's changing the world,' Weaver hopes 'maybe having a little bit of an impact' after 20+ years, suggesting modest vindication of his unconventional path.

“I go back to that meeting with Dave who said you know Graham's buying these stupid label printing companies and thinks he's changing the world and I'm may be having a little hopefully a little bit of an impact”