Venture capital through an anthropological lens
In this alumni episode, Eli Cahan (2019 cohort) speaks with Rex Woodbury (2019 cohort) who imagines a world where technology and startups are a force for good.
Rex reflects on his decision to leave the world of investment to attend business school and on how he began sharing his ideas on social media. He discusses how writing on Substack helped him pivot from private equity to venture capital, where he now supports early-stage founders as they develop their ideas. Rex believes technology can have a positive impact on society, and he describes how this work has given him a sense of meaning and purpose. He explains how Knight-Hennessy expanded his understanding of impact, situating impact entrepreneurship within broader structural issues. The episode concludes with Rex sharing his favorite memories from his time at Stanford and offering thoughtful advice to prospective students.
Resources
- Daybreak, Rex's venture capital firm
- Daybreak Ventures unveils $33 million first fund, Fortune
- Digital Native blog
- Rex's LinkedIn
- How Imagine A World began
Guest
Rex Woodbury, from Tucson, Arizona, is pursuing a master’s degree in business administration at Stanford Graduate School of Business. He graduated summa cum laude and Phi Beta Kappa from Dartmouth College with a bachelor’s degree in economics. Rex is interested in emerging internet and software platforms, with particular interests in online learning, next-generation media, and the future of work. He has recently worked at Airtable and at Calm, where he launched new growth channels and business verticals.
Before Stanford, he was an investor for TPG Growth and The Rise Fund, TPG’s global growth equity and social impact funds. At TPG Growth, he invested in internet businesses and led board diversity initiatives. At The Rise Fund, he executed the first investment in Latin America and launched Y Analytics, a public benefit corporation to measure social impact. Rex is the founder and CEO of Worthy, a nonprofit organization providing mentorship to the LGBTQ community. He has worked on social innovation policy for Governor Gavin Newsom and as an analyst for Goldman Sachs. For his work with Worthy, he was recognized by The Ellen DeGeneres Show.
Imagine A World team
Imagine A World's theme music was composed and recorded by Taylor Goss (2021 cohort). The podcast was originally conceived and led by Briana Mullen (2020 cohort), Taylor Goss, and Willie Thompson (2022 cohort), along with Daniel Gajardo (2020 cohort) and Jordan Conger (2020 cohort).
Knight-Hennessy scholars represent a vast array of cultures, perspectives, and experiences. While we as an organization are committed to elevating their voices, the views expressed are those of the scholars, and not necessarily those of KHS.
Full transcript
Note: Transcripts are generated by machine and lightly edited by humans. They may contain errors.
Rex Woodbury:
I think I only started a Twitter account when I was at GSB, and started writing Substack, I want to say my first year there, and part of the reason was to convince people I could do early stage. I came into GSB, and I was like, "Look, I want to do early. I love startups. I love the zero to one." And everyone looked at my resume, and was like, "TPG, guy, why don't you go join our growth team and go build this model?" And I was like, "You know what? I'm going to start writing digital native, and I'm going to do it every week, and I'm going to outwork other people, and I'm going to put my frameworks and theses out in the world, and then hopefully someone will read them and they'll be convinced that I'm actually an early-stage person kind of trapped in a private equity resume." And to Index's credit, they were one that saw through that, I think, and was like, "Oh, we actually think you have good ideas and can do early stage."
And I've really tried to be consistent with it throughout then, throughout my career, just because you never know when you throw out an idea who reads it, or so much of this job is if I write a piece about how healthcare is changing in the world of AI, I hope that someone in my network reads it and they meet a great founder, and they're like, "Oh, you're building this space? Like, Rex just wrote about it. You should meet him." And that's such an important part of an early-stage VC's job. It's how do you find and stay top of mind for really great entrepreneurs?
My name is Rex Woodbury. I was a member of the 2019 Knight-Hennessy cohort. I did a degree in business, and I imagine a world where technology and startups are a force for good.
Willie Thompson:
Welcome to the alumni edition of the Imagine A World podcast from Knight-Hennessy Scholars. We are here to give you a glimpse of Knight-Hennessy Scholars who have graduated and are making a difference in the world through their personal and professional endeavors. In each episode, we talk with KH alumni about the world they imagine and what they're doing to bring it to life. Today, we'll hear from Rex Woodbury, a member of the 2019 cohort from Tucson, Arizona. In this episode, Rex shares his experience building a career in finance, leaping into leading a venture fund, offers an anthropological take on venture capital, and so much more.
Eli Cahan:
Hello, everybody, and welcome back again to another edition of Imagine a World, the alumni edition, the best edition. You hear it every time. It is true. It is true, this is the best edition. I am thrilled to be here with a dear friend, who I haven't seen in a very long time. We were catching up off air, but I am just geeked to have him here, Rex Woodbury. Thank you so much for joining us on the podcast.
Rex Woodbury:
Thanks for having me, Eli.
Eli Cahan:
Great. Do you want to introduce yourself for the audience?
Rex Woodbury:
Sure. My name is Rex Woodbury. I was a member of the 2019 Knight-Hennessy cohort. I did a degree in business, and I imagine a world where technology and startups are a force for good.
Eli Cahan:
Great. Love that. Simple, punchy. Punchy, punchy.
Rex Woodbury:
Punchy.
Eli Cahan:
There it is. I think it's informative for folks to know a little bit about your journey, kind of everything that brought you up until the day that you wound up at Denning House on campus at Stanford.
Rex Woodbury:
Let's see. I would say every step in my career has been moving toward a bit more of my interests and what I'm interested in. So, I started my career more in late-stage investing. I worked at TPG before Stanford. I actually applied to Stanford when I was an undergrad, and so I was two plus two. I didn't apply to Knight-Hennessy until I was at TPG, but I did growth investing and impact investing before coming to Stanford. And the vision behind Knight-Hennessy, I mean, the reason I wanted to do it was because like any good millennial, I think I want to inject social impact into my career, and have a good purpose and a deeply fulfilled and impactful career. And I think Hennessy embodied that a lot, but I didn't know exactly what I wanted to do, and so coming to Stanford was my chance to try out a bunch of different things and figure out what, to me, is the authentic way that I can have an impactful career.
And I definitely tried out a lot of different stuff. It definitely took me a little bit to figure out what to do, but before it, I was late-stage investing more finance, and used my time at Stanford to reorient more toward the Bay Area startup world.
Eli Cahan:
I think one of the questions that probably you talk to a lot with just general mentees, people who are applying to business school in general, it strikes me that by the time you were thinking about applying to Stanford, you had a pretty robust resume. You had done a lot of really impactful things. You were on a pretty good trajectory. What made you think about wanting to come back to school?
Rex Woodbury:
I think for me, I started in a career where... I grew up in Tucson, Arizona. I knew nothing about business. I knew nothing about tech. I came to college and found myself, not accidentally, but definitely not on purpose, in investment banking world. Part of the reason was I went to college, and I think when I was a sophomore, there was an article about all of the valedictorians at the school going to Goldman Sachs and Morgan Stanley. And it wasn't even necessarily the most positive article, it was kind of just like, "This is where our best and brightest are going." But as the impressionable sophomore year, like "This is where the smartest kids are going." I don't yet know what I want to do with my life. And I think consulting, banking, those programs are really good about helping ambitious people understand that they're going to be trained for a general career in business without knowing exactly specifically what they want to do next.
And so I was like, "Great, this is a good place to go. I'll keep learning." And I went to Goldman, and then I was like, "Okay, I actually want to be on the investing side." I really liked the idea of working with people to build businesses, and dissecting businesses, and figuring out what makes a business tick. And so I moved over to the growth investing side of TPG, and that was one step closer to what I wanted to do, but I still was like, "I'm not really sure exactly." And I think you see that as a common career path of banking and private equity, and I think a lot of people then land at a place like Stanford GSB, and they're like, "Oh, shoot, what do I actually want to do? Now I actually have to figure it out." And I think for me, going to grad school was important because I was never really one of those people that came out of high school being like, "I want to be a doctor. I want to be in science, or I want to be a teacher."
I didn't know exactly. I knew that I was interested in people, and I knew I was interested in business, but it took me a little bit to find my footing. And Stanford, Knight-Hennessy, I mean, they kind of give you a safe place to explore a bunch of different stuff, and that was how I came into my years there. It was like, "I'm going to test a bunch of different theses of what I might want to do in the world, and I'm going to throw out the ones that aren't a fit, and I'm going to try to come out of here with a really good idea of where I want to build a career."
Eli Cahan:
I hate those doctors. Those lifelong doctor-types.
Rex Woodbury:
So, I come from a family of medicine, and both my parents are doctors. My brother's a doctor, and my brother's the opposite where-
Eli Cahan:
I'm so sorry. I'm sorry.
Rex Woodbury:
I mean, it's so funny, I am envious in some ways of... I think my brother knew he wanted to be a doctor when he was like eight years old, and he is one of those people who... We took AP chemistry together in high school. We're a year apart, and he would always be like, "Rex, oh, my God, can you believe that these types of molecules, and can you believe this, and the periodic table?" And he's just so enamored with science. And I was always a bit broader, where I was kind of like, "There was no school subject that I was super in love with, but I knew I liked people and reading about culture and technology," but I was envious that he knew from a young age what he wanted to do. And it took me probably another five or 10 years.
Eli Cahan:
Yeah. Well, I'm sure the test of time will vindicate that. I'm sure you guys are equally fun cocktail party guests, him with his molecules and you with your many adventures, which we'll get into. For somebody who... I read Liar's Poker. I similarly, I think, was interested in the world, sort of did this early investment banking path back in the day. I think a lot of people don't actually know what that entails, and nor do they really understand what the day in, day out of a role like growth investing at TPG would entail. Can you say a little bit about that, just again, to lay the foundation for where your mind was at as you were entering your experience at Stanford?
Rex Woodbury:
I think a place like Goldman, I mean, really what it does is I think it teaches you how to be a professional. Sometimes I'm like, "Wow, I feel like I learned how to write a good email and handle a good meeting, and all of the kind of intangible things." And I think that's true of consulting and banking. And I don't think you need to stay in those jobs for long to get it. I think a lot of people can be successful doing a year of training in banking and consulting, and then moving on to something that they really want to do. It was definitely good to cut my teeth. It was a lot of financial modeling. It's a lot of analysis. I mean, it was a good skillset to build. The growth investing side, I mean, it is kind of similar skillset to investment banking, but I would say much more rigorous, because what you're really trying to do is you're looking at, for me, it was a later-stage business, so in growth or private equity.
I mean, it's really a mature business, and can you dissect it to its component parts? And can you understand, at TPG, we would call it the what really matters questions? I mean, in every business, there are probably two or three things that really dictate the success of that business. And it could be the market size, it could be the timing of the product, it could be competition. But I think really understanding how to take a business and build it down into a few things that matter, that was the skill I took away, and it's a good foundation for anything you want to do in business. So, the goal there was really just train to understand businesses and what make them tick.
Eli Cahan:
Yeah. It sounds like a very particular kind of critical thinking.
Rex Woodbury:
Yeah. I mean, I joined as the first associate class that worked on the RISE Fund, which was TPG's Social Impact Fund. Largest impact fund in the world. I split my time between TPG growth, doing a lot of everything from consumer, to industrials, to technology businesses. And then on the social impact side of the RISE Fund, we did a lot of, quote-unquote, impact businesses, so those were businesses that would qualify for kind of mission-driven underwriting impact outcomes, think like hospital systems or education businesses selling to schools. And it's pretty broad. I mean, I think there are a lot of impactful companies in a lot of different sectors, but that was the dilemma I came into Knight-Hennessy. I called it my growth versus rise dilemma. I mean, a lot of the things that I was interested in, and finding myself reading about, were kind of more of the Airbnbs and Ubers of the world at the time.
But then I also felt this tension, where I really wanted to build a mission-driven impactful career, and so I came into Knight-Hennessy trying to square those two and figure out how do I follow my interest, but also feel really good about what I'm doing.
Eli Cahan:
Yeah. I seem to recall you talking a little bit about that in your GSB talk. I forget what it's called. I remember, you did just this... There's a tradition in GSB, Grad School of Business, which is the business school at Stanford, there's a tradition that folks in the class, I think, raise their hand to give these TED Talky-type of lectures. But again, I was on the outside looking in. I was only GSB curious and invited. I was always a plus one in the party, but my impression was these were so personal, so deep, and I do remember yours as one that sticks out very clearly in my mind as something that was pretty profound.
Rex Woodbury:
Thank you. Yeah. I mean, I feel like I came to GSB not having thought too critically about my career. I sort of had found myself from Arizona, and then college, and banking, and PE, and sort of was kicking the can down the road of what I really wanted until I got there, and the talk was a way to explore what actually interested me, where my mind went when I thought about the problems I wanted to solve, the people I wanted to work with, that kind of thing. And really, my whole time there, I think, was trying to take a step back, and be like, "Who was Rex? What do I want to do? Let me figure these things out." I'm like 27, 28, and I think it was productive in figuring those things out.
Eli Cahan:
Yeah. You kicked the can down the road, and eventually you sort of wind up juggling all the things that you're juggling now. And I want to talk first about what you're doing now, and then we'll back into how did Knight-Hennessy, and how did your Stanford time affect your thinking, and maybe give you answers to some of these questions. But I wonder, can you share a little bit about what you're doing now? Maybe start with the clearest thing on your LinkedIn, which would be your work with Daybreak Ventures.
Rex Woodbury:
Yeah. So, I started a venture fund two years ago, called Daybreak Ventures. After GSB, I worked at Index Ventures, one of the big venture firms in the world, amazing firm, and then started Daybreak. Really, I call it kind of a back to basics adventure. A lot of the thesis was ventures actually become a lot more private equity, like more asset management. It's become huge funds doing late-stage consensus sort of growth checks in great companies, but it's a different asset class than the root of venture, which is what I call more artisanal, more craftsman-like. It's very much the two founders in the proverbial garage, and their first believer who gets to work with them and kind of squint and believe that this can be a really big business. And I have moved earlier and earlier in my career, because I just get a lot more energized by seed stage, when it's non-obvious, when you find really spiky, ambitious people who aren't yet discovered, and you can help them shape the business, build the early team, those kinds of things.
And so we're a first-check fund. We started the fund in late 2023, and $33 million fund one, we invest as pre-seed and seed, and it's been fun.
Eli Cahan:
What does non-consensus mean to you? I mean, I saw this strewn all over your website, all over the amazing articles that Fortune Magazine and other people-
Rex Woodbury:
I feel like every VC firm probably says the same words.
Eli Cahan:
Well, it's interesting, because everyone says it and I think only a couple people actually exemplify it. So, I'm curious how you think about actualizing that every day, and how if people are listening here, who might be builders rather than funders, how you might think about encouraging and think about this in a way that is not contrarian for contrarian's sake, but non-consensus and visionary in a way that is a value add.
Rex Woodbury:
I mean, often the biggest companies were controversial at the start. What are famous examples? We're sitting here in San Francisco, I mean, Uber, it's like, would we get in a stranger's car? Airbnb, would we stay in a stranger's home? I mean, even now, this week, we had funding news of Kashi and prediction markets. I mean, those were very contrarian and non-consensus, and very binary, right? A lot of these can either be huge and generational companies or they just might not work, and I think those are the kinds of companies that really change culture, change how people live, change how people work. I think non-consensus unfortunately has become challenging, because a lot of the incentive structures in venture are almost like a playing a game of hot potato. We invest in the company so that someone else, we can pass it off to someone else, and they'll mark us up, and I'll get promoted.
And I think that's what happens when an asset class institutionalizes, it becomes much more of an echo chamber. And I think true original thought is rare, and I think that's what's nice about pre-seeds. You can find people who have really out-there views, and they might sound crazy today, but hopefully, if we squint, that's where the world is in 2030 or 2040, and that's our job.
Eli Cahan:
It strikes me that in some of the things that I've read about you talking about this work, you've also talked about that this is its own social anthropology, especially if you're funding, I think it said somewhere in the materials, "Before the first line of code is ever written." How do you think about getting behind people with big ideas rather than big ideas with people attached to them?
Rex Woodbury:
I think you can approach venture from a few different angles, and you see great venture capitalists come from all of these angles. Some people are true technologists, they were former engineers, or they live and breathe the technology. Some people are true finance people, and this is kind of the way I was trained, which is more... You maybe came from later stage, you moved earlier. I've always viewed myself in a third bucket, which is more anthropologist. And I think that's one of the fun parts about venture, it's really a study of people. And I mean this both in understanding how are consumers, or customers, of a company going to respond to new technology, but I also mean it in, really, it's about analyzing people and understanding people. I mean, if there's no product, or if everything is pre-everything for a startup at pre-seed or seed, it's really just the founder.
And can you understand what makes them tick? Why did they have that chip on their shoulder? Why did they have the X factor that's going to make them a generational founder? That's what I like. It's like spending time with people to understand them, and then also convince them that you're the right partner to help them realize their ambition.
Eli Cahan:
We're going to air this episode later, but we are recording this around the holidays, and I think it's non-coincidental that venture capitalists have some of the best holiday parties that I've been to. I guess it's part of the job description. You expense all of it and say it's for work that you're hanging out with people. But I certainly have heard from my other venture capital friends that getting to know people, and getting to evaluate people and their ideas, is such an important part of the job.
Rex Woodbury:
I mean, it's such a social job. And that can be exhausting and draining at times, but all of business is really just, I always say manufacturing serendipity. It's how do you surround yourself with smart people and share ideas? And then smart people tend to hang out around other smart people, and introduce you to others, and that's what startups are. I mean, even if you're looking to join a startup, it's really around did someone at that holiday party mention their friend who's starting this crazy thing? And that's why I think being in places like New York or San Francisco is so important for technology, because it has such density of talent, and really, it's who are those magnets, which companies become magnets for the best engineers and product people and salespeople.
Eli Cahan:
I want to get back to manufacturing serendipity, because that is very much a Knight-Hennessy ethos as well. That's something that I know people talk about. I think the terminology was "Planned serendipity" on campus and in Denning House. But before we go there, in the spirit of manufacturing serendipity, you have come into a couple other roles in your life that occupy your day-to-day, that feel deeply serendipitous, and yet are a huge part of your identity. I'm thinking about both the digital native newsletter, the Substack that you write, as well as your influencing presence on social media, which I'm thrilled that I get to say I saw you sweating after a run before the internet saw you sweating after runs in a [inaudible 00:18:28], on the initial retreat for Knight-Hennessy. But can you tell me a little bit about how those branches of your professional identity evolved, what they do to fill your cup, and why you keep doing them?
Rex Woodbury:
I mean, I generally think when it comes to venture, quality of VC is probably inversely proportional to number of Twitter followers. I think that is also true for founders. The exceptions are some of the great VCs like Bill Gurley or Keith Rabois, or some of these people who are quite prolific in putting their thoughts out there. But I grew up reading Fred Wilson from Union Square Ventures, and Bill Gurley wrote a blog called Above the Crowd, and Sarah Tavel at Benchmark also wrote a blog. I mean, I really was a student of these at a time when fortuitously, I was coming up alongside the internet, and I think all of a sudden you had all of the world's best founders and VCs doing podcasts, and doing YouTube channels, and doing interviews, and I was just a voracious learner and tried to soak that up.
And when I came to Stanford, I came from Goldman and TPG, where like, God knows, no one had a Twitter. I mean, that would be anathema. And I don't think writing a Substack would help you win a deal at TPG, it was much more a competitive bidding process, and you bid the highest price, or things like that. And Venture was very different. I think I only started a Twitter account when I was at GSB, and started writing Substack, I want to say my first year there. And part of the reason was to convince people I could do early stage. I came into GSB, and I was like, "Look, I want to do early. I love startups. I love the zero to one."
And everyone looked at my resume, and was like, "TPG, guy, why don't you go join our growth team and go build this model?" And I was like, "You know what? I'm going to start writing digital native, and I'm going to do it every, week and I'm going to outwork other people, and I'm going to put my frameworks and theses out in the world, and then hopefully someone will read them and they'll be convinced that I'm actually an early-stage person kind of trapped in a private equity resume." And to Index's credit, they were one that saw through that, I think, and was like, "Oh, we actually think you have good ideas and can do early stage."
And I've really tried to be consistent with it throughout my career, just because you never know when you throw out an idea, who reads it, or so much of this job is if I write a piece about how healthcare is changing in the world of AI, I hope that someone in my network reads it and they meet a great founder, and they're like, "Oh, you're building this space? Like, Rex just wrote about it. You should meet him." And that's such an important part of an early-stage VC's job, it's how do you find and stay top of mind for really great entrepreneurs?
Eli Cahan:
You now have about 70,000 followers, I think. Why do people read you?
Rex Woodbury:
It's interesting. I mean, the growth was very linear. We've done it, I've written it every week for six years now, and I would love to have a team and build out a content engine in Daybreak soon. I think that's a fun two initiative. But for me, it's I like doing it. I think even if no one read it, it would be a worthwhile exercise in synthesizing how I think about the world and keeping myself intellectually honest. And then it does have the added benefit of helping our companies by getting them customers or talent, and also attracting new great founders. So, I think it is helpful, but I think the reason, to answer your question, is I try to have a point of view. I think a lot of VC content out there is like the meme of people avoiding lasers, of people trying not to say something controversial, or trying not to say something that they'll be wrong about, and I think that gets it all wrong.
I think founders respect people who have a point of view and who have strong opinions weakly held, and I just put out a predictions piece for the next year. I'm like, I'm sure half of them will be wrong."
Eli Cahan:
Famous last words, yeah, yeah.
Rex Woodbury:
That is okay. I would rather be wrong but have a point of view. And so I think that's the reason. I think a lot of VC content is a little bit filler and trying to do no wrong, and I've always tried to just take a stance and have a point of view.
Eli Cahan:
How do you decide what to write about? I mean, you've written about everything. Just scrolling through the feed recently, you wrote about Nano Banana Pro, and I think you met Nancy Pelosi, I guess, apparently at an airport.
Rex Woodbury:
I mean, we're now in an age where you can fake anything.
Eli Cahan:
Anyone can Nancy Pelosi. You wrote about 10 charts that capture the world, you wrote about lessons from sci-fi. How do you decide what to write about? Where do you draw your inspiration, and how do you synthesize that onto the page?
Rex Woodbury:
I think I just try to follow my interest. I mean, this is why I like venture as a career. For anyone who is curious and likes to learn from really smart people, some of the smartest people in the world, who are living in the future, venture is a great career. I kind of started my career in late-stage world, where you'd be staffed on a project, and someone would say, "This factory makes paper bags, and you have to go learn about it and diligence it." And it was good training, but I never felt that energized by a lot of the stuff I was working on. In venture, I think there are no rules. You can just follow smart people and follow smart ideas, and form a point of view, and that's how I decide really. I'm trying to meet people and I start seeing patterns, and I'm like, "Oh, a bunch of people are building in legal tech with AI because of these reasons, and agents can now change this about the workflows." And then I'll follow that thread and maybe write about it and meet more people.
And that's one of the fun parts of the job. And I don't think there are many jobs in the world that pay you to just hang around smart people and think of big ideas and learn.
Eli Cahan:
Yeah, yeah. And in the spirit of predicting the future, you wrote in this newsletter on sci-fi, you wrote, "Clearly, sci-fi has done a good job predicting modern day. We shouldn't be surprised by this. There's a recurring theme. We can learn a lot from fiction about what the future might look like." I am curious, in the wake of that, what sci-fi are you thinking about to predict the future most recently? Is there a TV show you watch, or something you've consume, where you're like, "This is it. I got to follow this investment thesis?"
Rex Woodbury:
I think it's tough, because so much of sci-fi is so dystopian, and that makes for good entertainment, but I am very much of the believer that technology is a force for good, that startups are a vehicle for positive social change at scale, and so obviously, I'm a techno-optimist. I think you have to be in venture. I wish we had more world-positive sci-fi out there. If I ever have a second career as a film producer, I'll try to do maybe a Black Mirror equivalent that is more techno-optimist. I think with Black Mirror, we look at San Junipero as the only positive episode that comes out of four or five seasons there. So, to answer your question, I love Black Mirror. I think there are actually quite a few startups that have been predicted through Black Mirror, including in the AI world.
A related one that is lesser known is a show called Pantheon, which I think is very good. It's an animated show. It's on Netflix. It is dystopian, shocker, but basically the premise is a girl's dad passes away, but before he passes away, he actually has his brain scanned by a big tech corporation that creates a digital clone of him, an AI clone that lives in the cloud, and so she's able to still converse with him. Now, of course, these nefarious corporate titans start abusing his intellect and using him for bad things, and other people are abusing this technology. A hedge fund, for instance, clones top trader before she passes away, and then basically has her for eternity making trades that are very profitable for the hedge fund's behalf. So it kind of becomes this interesting, like is that slavery? Is that entrapment?
There are a lot of interesting social and ethical issues that stem from it, but we also have started to see some AI companies do this, where it's like, I have AIs that can learn about me and get to know me, and then you, as Eli, can chat with Rex's Delphi, as an example of a company in this space. And so I think there are obviously dystopian elements that we need good policy guardrails, and we need to put the right kind of things in place to make sure these are done in the right way, but I think shows like Pantheon actually do give you a glimpse of pretty cool technologies that are now possible.
Eli Cahan:
Yeah. It's all fun and good, and all techno-optimism until you accidentally clone like Larry David, or my Jewish mother, and you just get nagged for attorney. Then you're in trouble. Then, oh, God, you know what, let's go back to mortality. Mortality was really good.
Rex Woodbury:
It's so funny, because it has been interesting to watch this pessimism and skepticism and distrust of tech pervade America. It makes me sad. I mean, our lives are so much better because of technology. I think what that gets at, it's still this same vein of the rise in socialism and anti-capitalist sentiment, which I think is misplaced. Even Elizabeth Warren always says, "I'm a capitalist to my bones." What people are not liking is tech with no guardrails, or capitalism without good policy to reign it in. And so I do think AI is an amazing technology, I think our lives are going to get a lot better, but we also probably need some good policies and regulations in place.
Eli Cahan:
Yeah, yeah. We can have a whole conversation about this in healthcare. I know there's a lot of... Even recently, Center for Medicare and Medicaid Innovation came out with some new guidelines to try to promote use of AI in healthcare, and there's so much NIMBY-ism that's keeping costs high and making sure people unfortunately can't get the care they need, that they potentially could through AI. But anyway, conversation for another day. Last thing I want to touch on is influencing. This is something that I think it's interesting. A lot of people plan this. This is a very in vogue thing, especially among undergrads at Stanford's campus that I talk to. You have over 200,000 followers on Instagram at least, I guess the question is where does that fit? And again, what do you try to say there between the dog pictures and the Joshua Tree pictures, and why does that occupy some of your very scarce time?
Rex Woodbury:
It's interesting. I mean, I don't post very much on Instagram anymore. I think the reason that I have a lot of followers there, and I don't know, not something I'm super proud of, again, I'm going back to VCs being inversely proportional to number of Twitter followers. I do think generally, quality of human, probably inversely proportional to number of Instagram followers. I think that is generally true. And some of my best friends are instills and probably happier. I think for me it was in my 20s, I was in a public gay relationship, and there weren't that many very openly gay couples on Instagram. This is probably like 2015, 2016, 2017. And we were posting more, and I think people liked seeing themselves in another couple. And we just stumbled into it, I would say, and then tried to do some activism around it, and some LGBTQ mentoring organizations, and things like that.
I would say when I came to GSB is when I tried to make a conscious pivot of away from an Instagram to more Twitter and Substack, where I think you're rewarded more for your ideas. And those kinds of networks are ones where I'm like, "I would rather have a really long-form blog post that changes a lot of people's perspective on something versus a popular photo." So that was kind of one evolution for me and my relationship with different platforms, and now I think I view Instagram as a utility. It is very much Instagram DMs have replaced a lot of texting with a lot of my friends, and we have group chats and we share Reels. And I think it is so ingrained in our lives that it's hard to displace, but I would rather put my conscious efforts into more intellectual, like deep thinking, career-oriented stuff.
Eli Cahan:
Where did Knight-Hennessy fit into all of this? How, if at all, is any of what you're doing influenced by what you you learned, intentionally or unintentionally, during your time on campus?
Rex Woodbury:
I feel like for me, I've treated my time, I think, pretty intentionally, which I think is what people should do with grad school, around you come in with some hypotheses of what you think you might want to do, and you try to just figure out, in the course of one, two, three years, what are the things that energize you? It's almost like that Japanese concept of ikigai, that one of, "What am I good at? What do I like doing? What can I do well at?" I feel like for me it was a lot of understanding that. I mean, I actually worked in government my first term. I worked for the California governor. I pretty quickly was like, "That's not at least my near-term plan. I'm pretty set on going back to business and tech world, and it's faster moving and less bureaucracy." So I sort of threw out a lot of different things that were hypotheses, and then I realized were a little misguided.
Eli Cahan:
You're just mad because he didn't invite you to the French Laundry during COVID.
Rex Woodbury:
Exactly.
Eli Cahan:
Yeah.
Rex Woodbury:
I mean, I think it was literally right before that. And this was during primaries of Pete Buttigieg was rising up, and I was like, "Oh, being a mayor, a governor, that sounds impactful." And then I think I became a bit jaded and realized you can actually have a lot more impact through business world and tech world, I think. So a lot of it, for me, was just reorienting what I think of as social impact. Stanford, in general, is big on social innovation. Knight-Hennessy, of course, the whole program is built around this idea of empowering leaders to change the world for the better. For me, I think it was really changing my understanding of what is impact. It's not just the Rise Fund definition of investing in a hospital system or an education business. I would argue a lot of the biggest technology companies are deeply impactful.
Even like a YouTube, that's probably the biggest ed tech business in the world, right? Or Shopify. I mean, we don't think of that as impactful, or Etsy, but they underpin millions of small businesses. And that was kind of key to me of reframing, "Okay, these are the things I'm intellectually interested in, and these are the kinds of businesses that I'm fascinated by, and the kinds of founders I want to study." But it's not exactly where I thought I was going to be from a, quote-unquote, social impact perspective, but I actually find meaning and purpose in this, and that's exciting to me. So it was about figuring that out.
Eli Cahan:
How did Knight-Hennessy help you figure that out, and where did it fit relative to GSB? I mean, I think we'll bring alumni on, and I think there are characteristically different Stanford experiences. The PhD, or small master's program life, it's a very different kind of community that you have inherent to your degree program compared to any of the big professional degrees, like the GSB. And certainly, the GSB is notorious for having a very active and very beautiful community, probably the strongest amongst all the professional schools. Where did Knight-Hennessy fit both in your social life, as well as how did the programming that was happening through the pedagogy in Denning House differ, and perhaps support in a different way the questions you were trying to answer compared to the coursework and the hidden curriculum that you were going through at GSP?
Rex Woodbury:
I think being able to talk to people in a lot of different disciplines gives you appreciation of how impact comes in different forms. And even going back to my brother as an example, who's a doctor, I mean, he is someone who is so focused on depth of impact. He's like, "Rex, if I help one patient, that's enough," and that's what gives him energy and gets him excited every day. I was always a bit more probably indoctrinated into the business tech lens of impact at scale, why don't Carson, that's my brother, "You fix the broken healthcare system, AI," these things, and kind of realizing that both are meaningful. And when I was at Stanford, I got to interview Priscilla Chan from CZI, and I asked her the same question. I was like, "How do you think about depth of impact and breadth of impact?" And she basically-
Eli Cahan:
Priscilla Chan, the physician who is married to Mark Zuckerberg, and they co-founded the Chan Zuckerberg Initiative.
Rex Woodbury:
Chan Zuckerberg, yep, exactly. And amazing philanthropists, still practicing, I believe, a couple of days a week in San Francisco General Hospital. I'm not sure if that's still true, but it was at the time. And she basically was like, "Rex, you have to understand the depth to go broad." And her example was if she wasn't working in San Francisco General Hospital, she wouldn't have realized that the most important reason that her patients weren't getting care is the BART wasn't running on time. And then she was like, "Oh, actually, through CZI, I have to fund a billion dollar transformation of BART to make sure it runs on time, because my patients are not going to take the BART to the hospital to get care if they think they're going to miss a shift of work." And that was her example that really stuck with me of the depth then giving you the ability to go broad.
And I think in conversations at Knight-Hennessy, with people who were doctors, and who were teachers, and who had started nonprofits, gave me such broader appreciation for how actually the structural issues can be solved in a broader scale. And that came through exposure to... I mean, I remember really cool talks. Obviously, Phil Knight came and spoke to us, and learning from him, and getting perspective of what it was like to be an entrepreneur, and building Nike, and those kinds of things. And I mean, we had just an amazing kind of exposure to different speakers, and that just gave me more conviction in the path I was on.
Eli Cahan:
Yeah. Let's move into our last segment here, a popcorn segment. I'm going to hit you with a couple questions, and we'll just do sort of Rorschach test here.
Rex Woodbury:
All right. I'll do my best.
Eli Cahan:
What was your favorite King Global Leadership Series speaker? You mentioned Phil Knight. Are there other folks who stand out to you in the speaker series that we got through Knight-Hennessy, who shaped your-
Rex Woodbury:
Oh, man, putting me on the spot. I mean, I'm trying to think. This was five, six years ago now.
Eli Cahan:
Yeah, we're ancient.
Rex Woodbury:
I don't think he was at King Global Leadership, but talking to Steve Denning stands out to me. I remember talking to him, and he had such a good perspective on he'd come from the investing world, in private equity, and then moved into philanthropy, and I think that gave me good appreciation of moving from private equity world to venture world. John Hennessy too. I mean, also not officially in the King program, but I think being so available, and he is the polymath who speaks education and technology and business, and has done it all, and exposure to him every day. So those were probably the most memorable ones. I'll have to think during the rest of these popcorn questions, of who else jumps to mind.
Eli Cahan:
What was your favorite Knight-Hennessy trip?
Rex Woodbury:
It's a good question. Probably that first retreat. Where did we go? It was like up north in the Bay, or was it down south?
Eli Cahan:
Asilomar. Yeah, yeah, yeah.
Rex Woodbury:
Yeah, Asilomar. That was fun, because it was just the first quarter of school, and we were all together, staying in those cabins, and there was good curriculum there. And I loved always, we had the improv and the humor stuff to bond and learn to come into our own, so that one comes to mind.
Eli Cahan:
Yeah, totally. What was your favorite Denning House snack?
Rex Woodbury:
I probably had a lot of protein bars. I'm a big sparkling water guy. I don't know. You clearly have an answer to this. What did you say?
Eli Cahan:
There's a wrong answer to this, which is the answer that Ayo Dada gave us, which was making a sandwich out of microwaved yogurt, raisins, and bread. So, I have more wrong-
Rex Woodbury:
Yeah, that's the wrong answer.
Eli Cahan:
That is, yeah, a totally wrong answer.
Rex Woodbury:
I seem to remember a lot of peanut butter-filled pretzels. I believe I probably ate 10,000 calories a week in those.
Eli Cahan:
You know what they say about 10,000 hours?
Rex Woodbury:
Exactly.
Eli Cahan:
We need the depth of peanut butter pretzel experience to invest in peanut butter pretzel companies. As you probably remember, there's a tradition that when you leave Knight-Hennessy, you leave a book in the Denning House Library. Do you remember what book you left, or is there a book that if you were to do it again, you would leave now?
Rex Woodbury:
I think I left Americanah. I'm not sure. I was really into Chimamanda at the time. And I mean, my type of book has always been kind of a memoir, or a fictionalized book that reads almost like a memoir, and gives you insight into how a different person has lived. I think that's the one I left then. But if I left one now, actually the book I gave most often to friends now, is one called Tiny Beautiful Things. Have you read this book by Cheryl Strayed? The book is basically, she wrote it under a pen name, so she's a relatively famous author now. She wrote this book called Wild, which Reese Witherspoon was in the movie of, but for many years, she wrote an anonymous blog online called Dear Sugar. And the book, Tiny Beautiful Things is a compilation of some of the best essays.
And people will write in with all sorts of things, like, "Hey, I don't have a relationship with my dad. Do I invite him to my wedding?" Or, "Hey, I had a miscarriage, how do I get through this?" And she writes back with such beautiful, elegant, meaningful prose, and weaves in her own life story. And it reads almost more like a memoir, but also kind of a self-help book, and that is probably one of the books that gave me the best sense of humanity, and actually I feel like made me a more empathetic and compassionate person, so I recommend to anyone listening, Tiny Beautiful Things. It's an amazing book.
Eli Cahan:
If you had to get stranded on a desert island with one scholar from our cohort, or from a different cohort, who would it be and why?
Rex Woodbury:
Oh, I have to go with Emily Savage. I mean, never a dull moment with Emily. I mean, she was great because she was in the business program with me, but she was also doing the dual degree with Harvard Kennedy, and now she works in healthcare. I mean, I just adore her. She's full of hot takes. She's full of opinions. I like opinionated people, and Emily's as opinionated as you get, and just has the driest sense of humor out there, so that's my answer.
Eli Cahan:
Good to match that sense of humor with the amount of water on the island. She's definitely, yeah, lots of entertainment. I don't know how useful she'll be in building catamarans. But anyway, we do love Emily. Last question for you, what advice would you have for prospective applicants and potential future scholars?
Rex Woodbury:
I feel like it's such a cliche, but I feel like everyone's trying to think about what do other people want to hear? What does a Knight-Hennessy Scholar look like? What should I try to look like? And then also coming into the program, you're like, "What do people expect of me? What should I do?" And I don't know, honestly, I think it's just being authentic is such a buzz word now, but actually following the problems you want to do, reframing impact in the way you want to do it, trying to figure out what makes you tick, what's the ikigai there. And I wish earlier in my career, probably out of college, I'd given more thought to what actually is Rex passionate about? What does he want to do? What's he good at? Instead of kind of following a path, it took me probably a little bit later. It all ended up working out, but I think the sooner you can actually look yourself in the mirror, and be like, "What do I want to do with my life? What's authentic to me," the better.
Eli Cahan:
This was a great conversation.
Rex Woodbury:
Thanks for having me, Eli.
Eli Cahan:
Thanks so much for coming on. Thanks to our audience for tuning in. That's all she wrote. We'll see you next time.
Willie Thompson:
Thank you for joining us for this episode of Imagine a World, the alumni version, where we hear from inspiring graduates of the Knight-Hennessy community who are making significant contributions in their respective fields, challenging the status quo, and pushing the boundaries of what is possible as they imagine the world they want to see. This podcast is sponsored by Knight-Hennessy Scholars at Stanford University, a multidisciplinary, multicultural graduate fellowship program, providing scholars with financial support to pursue graduate studies at Stanford while helping equip them to be visionary, courageous, and collaborative leaders who address complex challenges facing the world. Please follow us on social media at Knight-Hennessy, and visit our website, at kh.stanford.edu, to learn more about the program and our community.
