.@infoarbitrage and I are back with the 5th annual venture summit in Ann Arbor tomorrow! We will feature @fredwilson and @dickc discussing Twitter's growth years and a great panel on building winning teams which will include star basketball players @mckenneytrey1 and @SylaSwords and their coaches. +amazing founders, GPs, LPs. Please register in link and run of show below. venturesummita2.co/

WHAT IS YOUR GAME? A few days ago I was reflecting on the importance of blocking out the never-ending cacophony, engaging in self-care and playing your game (PYG). After re-reading the piece, I thought it might be helpful to share my own experience of how I figured out my game and the path I took to get here. Tl;dr: it wasn't easy, it wasn't linear and it is still evolving to this day. And that is part of the fun. I grew up in the liquid markets. Hedging and risk management were paramount to both my work with clients and managing large amounts of capital as a principal. This was the training I received and the culture in which I was immersed for the first 17 years of my career on Wall Street. When this period ended and I decided to focus on very early stage venture investing, I went from managing massive amounts of capital at scale with tight risk tolerances to investing my own dollars in the least liquid asset class known to humanity. To say this represented an abrupt phase shift is a gross understatement. No rational person would do such a thing. Well, perhaps you haven't met me! The day-to-day stress of being responsible for teams managing billions in liquid trading capital is very different from the stress of what feels like throwing a bag of money over the transom and believing that someday, perhaps 7, 10 or even 15 years in the future, someone will toss you 50-100 bags back. When managing a liquid trading business, you know how you're doing day to day, and sometimes minute to minute depending upon the strategy. When managing a seed-stage venture portfolio, you don't know if you're good or shit for sometimes half a generation. It takes a certain kind of steeliness to handle either psychological state, but I'm pretty sure that most of my former Wall Street colleagues would lose their fucking minds trying to do what I've been doing for the past 20 years. As noted above, who would do such a thing (lol). So this is part of the backdrop of how I eventually chose my game. When I started in venture, I noticed pretty quickly that my institutional-grade risk management and portfolio construction skills were uncommon. I hypothesized that these could be valuable but had no data to back up my assertions. But what I did have was capital to risk and time to run some experiments before I subjected others to my particular brand of investing. To ground the discussion, I am talking about the 2004-09 period, between the time I left Wall Street and started IA Ventures. I was an angel investor with the desire to see if I was any good at the venture investing business and whether I had a true edge relative to others. The edge I was looking for was some combination of smart founder selection (leadership identification), keen product insight (stock picking), and bet sizing and economic alignment relative to my bankroll (portfolio management). While these analogs to my prior activities weren't perfect, they did offer a solid framework within which to assess my fitness for choosing this as a career and potentially managing LP dollars (as well as more of my own). During this time my game could be characterized as an amalgam of the following: - Deep experience coaching and recruiting technical talent - Battle scars that could help founders avoid similar mistakes - Willingness to lead a round and corral other investors - Empathetic truth teller - Calming influence when situations get stressful - Roll-up-the-sleeves problem solver This was a pretty good place to start given that I had -0- venture investing experience and a limited reputation in the startup space. Through a crazy amount of networking among founders, VCs and builders, I began to see a flywheel effect where my reputation as a professional angel generated attractive opportunities from both founders and VCs who were excited to have me on their cap table, which in turn yielded social proof that caused the flywheel to spin faster. I also began to write my original blog, Information Arbitrage, which helped me find my voice and became a powerful platform for sharing ideas, enabling potential partners to understand who I was and how I thought. Though early, my game began to come into focus. I pursued this approach for almost five years before the disparate threads of how to be the kind of investor I wanted to be came together. I wanted to lead very early stage investment rounds and earn the position of the most important partner to founders on the cap table, from pre-seed through IPO. I wanted to build a concentrated portfolio where I was deeply involved in every company, especially during the 0=>1 period, and would, on average, buy 12-20% of a business with my first investment. I also wanted to be highly disciplined when writing subsequent checks, and very transparent with founders about my decision-making rubric to ensure there were no surprises when they went out for funding rounds. This meant every investment in a business had to stand on its own, with return potential aligned with my investment objectives. As a practical matter, this meant no naive pro rata follow-ons, though perhaps a smaller support check if we wanted the founder to be able to say I participated even if I didn't do my full pro rata or beyond. But if I had deep conviction when it came time to write that second check—or even before that, if I felt the founders had lightning in a bottle and I wanted to help them capture it sooner than a normally paced follow-on round might indicate—I wanted to be willing and able to "back up the truck" and put 10% or more of my entire fund behind a single company. This approach, I was convinced, was a style that fit my temperament, was great for founders and could help me generate exceptional investment returns for me and my partners. This was the game I brought to the founding of IA Ventures, and it was the game that has helped IA generate some of the better returns in the venture business. And it is, for all intents and purposes, the game we are playing at GCV—with one notable exception. Something happened during my time at IA that I'd like to share, and I am curious if other investors have had this happen to them. I can't put my finger on why it happened, but it did, and it changed the amount of fun I had during the latter part of my time there. It had nothing to do with Brad or Jesse: they were and are the best, full stop. It had nothing to do with our LPs: we were blessed with one of the best cap tables in the venture world. It happened within me, and it happened after we had achieved a lot of success, perhaps in the 2016-17 time frame. I STARTED TO BE AFRAID OF BEING WRONG AND LOOKING DUMB. It hurts me to write this because it is, frankly, pretty embarrassing. I thought I had overcome my strict Wall Street risk-management mindset over the prior 10-12 years, but for some reason, once we had objective success, my reaction was to fear losing it rather than viewing that success—and the demonstration of my instincts and skill—as having earned the right to play with even more chips. I couldn't articulate it back then, but I can see it with perfect clarity today. It really sapped the fun out of my work and was psychologically damaging because I had stopped being my authentic self. It made me a worse investor. So much of what had made me successful was the ability to say "fuck it" if I felt something was right even if it was crazy, and to be perfectly ok if my wild-ass bet was wrong because, you know, if one or two of my wild-ass bets hit, then I've made the fund and possibly the firm. But even though I intellectually knew this, I felt paralyzed to change it. And if I'm honest, this realization—combined with the knowledge that IA was no longer my firm, but ours—helped me conclude that it was time to give the firm to Brad and Jesse and begin the next chapter of my life and career, whatever that might be. I was sad to feel like I was leaving with a whimper, but I felt great about leaving the firm and our LPs (and most of my net worth) in amazing hands. So there is one key addition to the game I am playing today versus the one I played during the latter part of my IA career: LEVERAGE THOSE KEEN ANGEL INSTINCTS AND LET IT RIP! I never lost my sense of what made for great founders, orthogonal thinkers and bold ideas to create or disrupt large markets. I had just let it get covered up. No more. This new firm—mine, Simon's and Ethan's firm—is a combination of instinct, smart but not obsessive diligence, deep conviction, speed and risk taking. All the other stuff—helping crazy-driven founders working on interesting ideas get from 0=>1, providing calm, stable support in good times and bad, pushing them to be their best selves and having a good time working together in the process—is the same. But today I have no fear—only optimism, the willingness to trust my instincts and a relentless drive to win. Oh my, does it feel good to be back... @gamechangersvc @ssokol94 @ethanehrenberg #vc #founders

WHAT IS YOUR GAME? A few days ago I was reflecting on the importance of blocking out the never-ending cacophony, engaging in self-care and playing your game (PYG). After re-reading the piece, I thought it might be helpful to share my own experience of how I figured out my game and the path I took to get here. Tl;dr: it wasn't easy, it wasn't linear and it is still evolving to this day. And that is part of the fun. I grew up in the liquid markets. Hedging and risk management were paramount to both my work with clients and managing large amounts of capital as a principal. This was the training I received and the culture in which I was immersed for the first 17 years of my career on Wall Street. When this period ended and I decided to focus on very early stage venture investing, I went from managing massive amounts of capital at scale with tight risk tolerances to investing my own dollars in the least liquid asset class known to humanity. To say this represented an abrupt phase shift is a gross understatement. No rational person would do such a thing. Well, perhaps you haven't met me! The day-to-day stress of being responsible for teams managing billions in liquid trading capital is very different from the stress of what feels like throwing a bag of money over the transom and believing that someday, perhaps 7, 10 or even 15 years in the future, someone will toss you 50-100 bags back. When managing a liquid trading business, you know how you're doing day to day, and sometimes minute to minute depending upon the strategy. When managing a seed-stage venture portfolio, you don't know if you're good or shit for sometimes half a generation. It takes a certain kind of steeliness to handle either psychological state, but I'm pretty sure that most of my former Wall Street colleagues would lose their fucking minds trying to do what I've been doing for the past 20 years. As noted above, who would do such a thing (lol). So this is part of the backdrop of how I eventually chose my game. When I started in venture, I noticed pretty quickly that my institutional-grade risk management and portfolio construction skills were uncommon. I hypothesized that these could be valuable but had no data to back up my assertions. But what I did have was capital to risk and time to run some experiments before I subjected others to my particular brand of investing. To ground the discussion, I am talking about the 2004-09 period, between the time I left Wall Street and started IA Ventures. I was an angel investor with the desire to see if I was any good at the venture investing business and whether I had a true edge relative to others. The edge I was looking for was some combination of smart founder selection (leadership identification), keen product insight (stock picking), and bet sizing and economic alignment relative to my bankroll (portfolio management). While these analogs to my prior activities weren't perfect, they did offer a solid framework within which to assess my fitness for choosing this as a career and potentially managing LP dollars (as well as more of my own). During this time my game could be characterized as an amalgam of the following: - Deep experience coaching and recruiting technical talent - Battle scars that could help founders avoid similar mistakes - Willingness to lead a round and corral other investors - Empathetic truth teller - Calming influence when situations get stressful - Roll-up-the-sleeves problem solver This was a pretty good place to start given that I had -0- venture investing experience and a limited reputation in the startup space. Through a crazy amount of networking among founders, VCs and builders, I began to see a flywheel effect where my reputation as a professional angel generated attractive opportunities from both founders and VCs who were excited to have me on their cap table, which in turn yielded social proof that caused the flywheel to spin faster. I also began to write my original blog, Information Arbitrage, which helped me find my voice and became a powerful platform for sharing ideas, enabling potential partners to understand who I was and how I thought. Though early, my game began to come into focus. I pursued this approach for almost five years before the disparate threads of how to be the kind of investor I wanted to be came together. I wanted to lead very early stage investment rounds and earn the position of the most important partner to founders on the cap table, from pre-seed through IPO. I wanted to build a concentrated portfolio where I was deeply involved in every company, especially during the 0=>1 period, and would, on average, buy 12-20% of a business with my first investment. I also wanted to be highly disciplined when writing subsequent checks, and very transparent with founders about my decision-making rubric to ensure there were no surprises when they went out for funding rounds. This meant every investment in a business had to stand on its own, with return potential aligned with my investment objectives. As a practical matter, this meant no naive pro rata follow-ons, though perhaps a smaller support check if we wanted the founder to be able to say I participated even if I didn't do my full pro rata or beyond. But if I had deep conviction when it came time to write that second check—or even before that, if I felt the founders had lightning in a bottle and I wanted to help them capture it sooner than a normally paced follow-on round might indicate—I wanted to be willing and able to "back up the truck" and put 10% or more of my entire fund behind a single company. This approach, I was convinced, was a style that fit my temperament, was great for founders and could help me generate exceptional investment returns for me and my partners. This was the game I brought to the founding of IA Ventures, and it was the game that has helped IA generate some of the better returns in the venture business. And it is, for all intents and purposes, the game we are playing at GCV—with one notable exception. Something happened during my time at IA that I'd like to share, and I am curious if other investors have had this happen to them. I can't put my finger on why it happened, but it did, and it changed the amount of fun I had during the latter part of my time there. It had nothing to do with Brad or Jesse: they were and are the best, full stop. It had nothing to do with our LPs: we were blessed with one of the best cap tables in the venture world. It happened within me, and it happened after we had achieved a lot of success, perhaps in the 2016-17 time frame. I STARTED TO BE AFRAID OF BEING WRONG AND LOOKING DUMB. It hurts me to write this because it is, frankly, pretty embarrassing. I thought I had overcome my strict Wall Street risk-management mindset over the prior 10-12 years, but for some reason, once we had objective success, my reaction was to fear losing it rather than viewing that success—and the demonstration of my instincts and skill—as having earned the right to play with even more chips. I couldn't articulate it back then, but I can see it with perfect clarity today. It really sapped the fun out of my work and was psychologically damaging because I had stopped being my authentic self. It made me a worse investor. So much of what had made me successful was the ability to say "fuck it" if I felt something was right even if it was crazy, and to be perfectly ok if my wild-ass bet was wrong because, you know, if one or two of my wild-ass bets hit, then I've made the fund and possibly the firm. But even though I intellectually knew this, I felt paralyzed to change it. And if I'm honest, this realization—combined with the knowledge that IA was no longer my firm, but ours—helped me conclude that it was time to give the firm to Brad and Jesse and begin the next chapter of my life and career, whatever that might be. I was sad to feel like I was leaving with a whimper, but I felt great about leaving the firm and our LPs (and most of my net worth) in amazing hands. So there is one key addition to the game I am playing today versus the one I played during the latter part of my IA career: LEVERAGE THOSE KEEN ANGEL INSTINCTS AND LET IT RIP! I never lost my sense of what made for great founders, orthogonal thinkers and bold ideas to create or disrupt large markets. I had just let it get covered up. No more. This new firm—mine, Simon's and Ethan's firm—is a combination of instinct, smart but not obsessive diligence, deep conviction, speed and risk taking. All the other stuff—helping crazy-driven founders working on interesting ideas get from 0=>1, providing calm, stable support in good times and bad, pushing them to be their best selves and having a good time working together in the process—is the same. But today I have no fear—only optimism, the willingness to trust my instincts and a relentless drive to win. Oh my, does it feel good to be back... @gamechangersvc @ssokol94 @ethanehrenberg #vc #founders

WHAT IS YOUR GAME? A few days ago I was reflecting on the importance of blocking out the never-ending cacophony, engaging in self-care and playing your game (PYG). After re-reading the piece, I thought it might be helpful to share my own experience of how I figured out my game and the path I took to get here. Tl;dr: it wasn't easy, it wasn't linear and it is still evolving to this day. And that is part of the fun. I grew up in the liquid markets. Hedging and risk management were paramount to both my work with clients and managing large amounts of capital as a principal. This was the training I received and the culture in which I was immersed for the first 17 years of my career on Wall Street. When this period ended and I decided to focus on very early stage venture investing, I went from managing massive amounts of capital at scale with tight risk tolerances to investing my own dollars in the least liquid asset class known to humanity. To say this represented an abrupt phase shift is a gross understatement. No rational person would do such a thing. Well, perhaps you haven't met me! The day-to-day stress of being responsible for teams managing billions in liquid trading capital is very different from the stress of what feels like throwing a bag of money over the transom and believing that someday, perhaps 7, 10 or even 15 years in the future, someone will toss you 50-100 bags back. When managing a liquid trading business, you know how you're doing day to day, and sometimes minute to minute depending upon the strategy. When managing a seed-stage venture portfolio, you don't know if you're good or shit for sometimes half a generation. It takes a certain kind of steeliness to handle either psychological state, but I'm pretty sure that most of my former Wall Street colleagues would lose their fucking minds trying to do what I've been doing for the past 20 years. As noted above, who would do such a thing (lol). So this is part of the backdrop of how I eventually chose my game. When I started in venture, I noticed pretty quickly that my institutional-grade risk management and portfolio construction skills were uncommon. I hypothesized that these could be valuable but had no data to back up my assertions. But what I did have was capital to risk and time to run some experiments before I subjected others to my particular brand of investing. To ground the discussion, I am talking about the 2004-09 period, between the time I left Wall Street and started IA Ventures. I was an angel investor with the desire to see if I was any good at the venture investing business and whether I had a true edge relative to others. The edge I was looking for was some combination of smart founder selection (leadership identification), keen product insight (stock picking), and bet sizing and economic alignment relative to my bankroll (portfolio management). While these analogs to my prior activities weren't perfect, they did offer a solid framework within which to assess my fitness for choosing this as a career and potentially managing LP dollars (as well as more of my own). During this time my game could be characterized as an amalgam of the following: - Deep experience coaching and recruiting technical talent - Battle scars that could help founders avoid similar mistakes - Willingness to lead a round and corral other investors - Empathetic truth teller - Calming influence when situations get stressful - Roll-up-the-sleeves problem solver This was a pretty good place to start given that I had -0- venture investing experience and a limited reputation in the startup space. Through a crazy amount of networking among founders, VCs and builders, I began to see a flywheel effect where my reputation as a professional angel generated attractive opportunities from both founders and VCs who were excited to have me on their cap table, which in turn yielded social proof that caused the flywheel to spin faster. I also began to write my original blog, Information Arbitrage, which helped me find my voice and became a powerful platform for sharing ideas, enabling potential partners to understand who I was and how I thought. Though early, my game began to come into focus. I pursued this approach for almost five years before the disparate threads of how to be the kind of investor I wanted to be came together. I wanted to lead very early stage investment rounds and earn the position of the most important partner to founders on the cap table, from pre-seed through IPO. I wanted to build a concentrated portfolio where I was deeply involved in every company, especially during the 0=>1 period, and would, on average, buy 12-20% of a business with my first investment. I also wanted to be highly disciplined when writing subsequent checks, and very transparent with founders about my decision-making rubric to ensure there were no surprises when they went out for funding rounds. This meant every investment in a business had to stand on its own, with return potential aligned with my investment objectives. As a practical matter, this meant no naive pro rata follow-ons, though perhaps a smaller support check if we wanted the founder to be able to say I participated even if I didn't do my full pro rata or beyond. But if I had deep conviction when it came time to write that second check—or even before that, if I felt the founders had lightning in a bottle and I wanted to help them capture it sooner than a normally paced follow-on round might indicate—I wanted to be willing and able to "back up the truck" and put 10% or more of my entire fund behind a single company. This approach, I was convinced, was a style that fit my temperament, was great for founders and could help me generate exceptional investment returns for me and my partners. This was the game I brought to the founding of IA Ventures, and it was the game that has helped IA generate some of the better returns in the venture business. And it is, for all intents and purposes, the game we are playing at GCV—with one notable exception. Something happened during my time at IA that I'd like to share, and I am curious if other investors have had this happen to them. I can't put my finger on why it happened, but it did, and it changed the amount of fun I had during the latter part of my time there. It had nothing to do with Brad or Jesse: they were and are the best, full stop. It had nothing to do with our LPs: we were blessed with one of the best cap tables in the venture world. It happened within me, and it happened after we had achieved a lot of success, perhaps in the 2016-17 time frame. I STARTED TO BE AFRAID OF BEING WRONG AND LOOKING DUMB. It hurts me to write this because it is, frankly, pretty embarrassing. I thought I had overcome my strict Wall Street risk-management mindset over the prior 10-12 years, but for some reason, once we had objective success, my reaction was to fear losing it rather than viewing that success—and the demonstration of my instincts and skill—as having earned the right to play with even more chips. I couldn't articulate it back then, but I can see it with perfect clarity today. It really sapped the fun out of my work and was psychologically damaging because I had stopped being my authentic self. It made me a worse investor. So much of what had made me successful was the ability to say "fuck it" if I felt something was right even if it was crazy, and to be perfectly ok if my wild-ass bet was wrong because, you know, if one or two of my wild-ass bets hit, then I've made the fund and possibly the firm. But even though I intellectually knew this, I felt paralyzed to change it. And if I'm honest, this realization—combined with the knowledge that IA was no longer my firm, but ours—helped me conclude that it was time to give the firm to Brad and Jesse and begin the next chapter of my life and career, whatever that might be. I was sad to feel like I was leaving with a whimper, but I felt great about leaving the firm and our LPs (and most of my net worth) in amazing hands. So there is one key addition to the game I am playing today versus the one I played during the latter part of my IA career: LEVERAGE THOSE KEEN ANGEL INSTINCTS AND LET IT RIP! I never lost my sense of what made for great founders, orthogonal thinkers and bold ideas to create or disrupt large markets. I had just let it get covered up. No more. This new firm—mine, Simon's and Ethan's firm—is a combination of instinct, smart but not obsessive diligence, deep conviction, speed and risk taking. All the other stuff—helping crazy-driven founders working on interesting ideas get from 0=>1, providing calm, stable support in good times and bad, pushing them to be their best selves and having a good time working together in the process—is the same. But today I have no fear—only optimism, the willingness to trust my instincts and a relentless drive to win. Oh my, does it feel good to be back... @gamechangersvc @ssokol94 @ethanehrenberg #vc #founders

Six months ago, we formally launched @gamechangersvc. It feels good — really good — to be back building a firm from scratch around ideas and domains where I have deep conviction. Even better is doing it with @ssokol94 and @ethanehrenberg, and with the founders we’ve had the privilege to back so far. Early-stage venture, when done right, is not a transactional business. It’s a deeply personal one. Our job is to help founders become the best versions of themselves — as leaders, as decision-makers, and as humans — while they attempt something very hard. I believe we’re doing that the right way. I also believe what we’re building into is not cyclical, but secular. AI will reshape almost everything about how we work and create. Paradoxically, that will only increase the value of being human together — gathering, belonging, cheering, participating, identifying with something larger than ourselves. Sports, entertainment, live experiences, and the technologies that power them sit squarely in that shift. To us, it looks like a generational opportunity. When I first announced the firm, I mentioned that we would eventually add one more partner-level person. That remains true. There is no job description. There is no timeline. There is no “process.” What there is: openness. We are looking for someone who is AI-native in their thinking, intellectually curious, comfortable with ambiguity, and genuinely passionate about sport, entertainment, community, and culture. Someone who wants to build a firm — not just join one. Someone who extends how we think rather than simply amplifying what we already do. This person may not currently be in venture. They may not even be in this sector. In fact, that could be a feature, not a bug. The goal isn’t incremental horsepower. It’s new perspective, judgment, creativity, and values alignment. There is also no rush. The right partnership is discovered, not hired. We’ll get to know this person over time, and they’ll get to know us. In all likelihood, this will be the last person we ever add. The aspiration is a very small, very high-trust, very long-term partnership — similar to what we built at @iaventures. That model worked pretty well, and it was a lot of fun. If this resonates with you — or with someone you think we should know — my inbox is open. roger@gamechangers.vc #LFG #vc #builders