← Capital Allocators – Inside the Institutional Investment Industry
Capital Allocators – Inside the Institutional Investment Industry
Katelin Holloway – Human Side of Venture Investing at 776 (EP.490)
01:10:55
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- [00:00]
Caitlin Holloway
Here's my secret, Ted early stage investing is fundamentally about people and systems under conditions of extreme uncertainty and distress. After a decade of operating as an HR executive and helping companies from inception to hypergrowth and blitzscaling through eventual exit, that pattern alignment of playbooks I was using to support organizations. Turns out it was an exact match to growing and supporting a portfolio of organizations. I developed this thesis that if early stage investing is akin to every HR process that I was the godmother of in this new world of people and culture, why aren't there more people who look like me sitting on the other side of the boardroom table? If you break down early stage investing, there's some simple buckets. There is sourcing, which is how do you find the best founders in the world? That is the same as recruiting. We use the same word, sourcing. Sourcing. How do I source the top talent? To understand sourcing you have to understand community. You have to understand network. The third bucket is servicing. I've spent my entire career enabling people to fulfill their potential. Those buckets I was an expert in. So if that's what makes a great investor, why couldn't you give an HR lady a checkbook?
- [01:20]
Ted Seides
I'm Ted Seides and this is Capital Allocator. My guest on today's show is Caitlin Holloway, founding partner at 776 technology focused venture firm backing great early stage entrepreneurs that she started with Alexis Ohanian in 2020. Alexis was a past guest on the
- [01:42]
Interviewer/Host
show and that conversation is replayed in the feed.
- [01:45]
Ted Seides
Caitlin and I explore the intersection of human capital and venture capital. We cover her upbringing, work alongside Steve Jobs at Pixar, and turnaround of Reddit. With Alexis, we then turn to the application of her operational experience to venture investing. We discuss 776 is sourcing and underwriting of founders, interviewing approach, investment selection and scaling. The highly personal approach it takes to add value to portfolio companies before we get going. I recently returned from a week's ski vacation to Switzerland with my son E. The same son who shared his serendipitous encounter with the podcast last week. Snow conditions have been challenging almost everywhere this season, but we were excited to travel to Europe for the first time to ski. Our trip there and back was full on trains, planes and automobiles. We got a taste of the beauty, food and culture that everyone raves about in Zermatt. As for skiing, between snow conditions we're accustomed to in Vermont and a white out blizzard our last two days we only two full days of skiing, but we certainly left the mountain better off than we found it for skiers. The next week it would be safe to question my sanity for making the long trip to ski only two days. But the truth is, the number of full weeks I have left one on one with my 16 year old son are numbered. So I took in every moment, even when our plans for an active week were shot. What we did have was plenty of time to listen to podcasts.
- [03:20]
Sponsor/Advertisement Voice
Although, as you may have heard last
- [03:22]
Ted Seides
week, Eric wasn't about to listen to Capital Allocators. But that's okay. He's happy to encourage you to listen and to tell your friends and their friends to listen. What he doesn't know is that process will inevitably get back to him through his friend's parents, offering another opportunity for him to think twice. And one day, one day, just maybe, he'll listen too. Thanks so much for starting a butterfly effect by spreading the word about Capital Allocators. That butterfly may be flapping its wings in the winter in Switzerland and one day find its way to Eric Capital
- [03:56]
Sponsor/Advertisement Voice
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- [06:01]
Interviewer/Host
Caitlin, thanks so much for doing this.
- [06:03]
Caitlin Holloway
Thank you so much for having me, Ted. I'm really excited to chat.
- [06:06]
Interviewer/Host
I'd love to go back to your early career.
- [06:12]
Caitlin Holloway
I'm going to take you back to the very beginning. I was born in Fairbanks, Alaska, raised in Stockton, California. If you know anything about either of these great American cities, you'll know well enough that I can fend for myself out there. I'm pretty sure that our main export was grit for both of those towns. I wasn't born into a world where I had a ton of opportunity. My resume looks wildly nonlinear. In my early part of my career, I worked so many different jobs out of necessity and retail hospitality. I worked out in the fields picking cucumbers and green beans. Eventually made my way into things like law enforcement and banking. There are many, many industries that I've worked in just to stay afloat. What I didn't realize at the time I was getting this front row seat to how power incentives and trust operate inside of systems. Especially being so young. That was my place and the only thing I could do was watch and draw patterns.
- [07:07]
Interviewer/Host
What were some of those early patterns that you drew?
- [07:11]
Caitlin Holloway
I got good at reading people, understanding power dynamic that it didn't always match an org chart didn't matter whether I was out picking green beans or if I was booking someone at the PD up in Arcata. There was a cultural framework that was established within not just each of the industries, but within each of those companies or groups of humans coming together to do something that didn't always read in sequential order. I learned how to navigate quickly, keep your head down, make sure you make good with the right people, make sure that people know your name, that you want and don't that you don't. Those things shaped my career arc once I did graduate from undergrad.
- [07:53]
Ted Seides
And then what'd you do after undergrad?
- [07:55]
Caitlin Holloway
Teaching was the first job that really shaped me. This was back in 2001. I taught first and second grade and then I moved up to teaching high school, working in a classroom with 33 first and second graders, all of them with severe learning disabilities. Most of the students were English as a Second Language. This was in Stockton. I learned a lot about the consequences of bad systems on real people. That easily was the hardest job of my career to date. So I quit. I love teaching. I was raised by a teacher. My mom taught third grade her entire life. I deeply understood why. It was the most important job that we could have in our society. But I loved San Francisco more, man. I left Stockton, I'd saved up all those paychecks, and I moved to the big city. Pixar was my next big beat. I had not intended to go into film. I didn't have a creative background. That was a real inflection point, because at that point in my life, I'd finally collected enough beans to make a burrito. I had earned the privilege of being able to design my career as opposed to just taking the jobs that were in front of me or were available to me so that I could pay rent. Pixar. It's funny, I call that my true education. I was 25 years old and I'd already been working half my life. For most people, that's when they're getting their first jobs, when their early career is just starting to blossom and develop. I worked so much through school, I'd forgotten to learn while I was there. I knew how to get through the system. I didn't know how to absorb it. I didn't have the space to do anything. With that education, Pixar became my first unofficial master's degree in business. I spent five of some of the greatest years in life at that studio. I worked across dozens of films with some of the most incredible creatives of our generation, and also business leaders. I was working directly with and for Steve Jobs, Ed Catmull, John Lasseter. I fell so deeply in love with my work. That was the first time I had felt that through that love, I tried to understand what made that place different, what made it different than everything else I had done to that point in my life. It boiled down to how that company chose to operate.
- [10:04]
Interviewer/Host
What did you find was special about how Pixar worked?
- [10:09]
Caitlin Holloway
I truly fell in love with that company. I fell in love with the people that I worked with. I fell in love with the product we were producing. I fell in love with the creative process. Everyone else felt the same way. There wasn't a single person at that studio who didn't love their job as much as I did and didn't have that shared accountability, trust and respect across the organization. It didn't matter what role you were in. The passion and drive of the people who worked at the studio was palpable. That didn't just show up in the friendships that were built and the relationships made or the high fives over a job well done. In a film review, it showed up in the stories on the screen. When that passion and those stories were translated into the dark theaters across the globe, the business results were undeniable. This was the first time I saw a company intentionally design culture as infrastructure. There were consistent, frequent feedback loops. Creative trust, psychological safety. All of it was not because it felt good or because it was the nice thing to do. If anyone has read anything about Steve Jobs or Ed Catmull, they don't lead from that place. It was in service of excellence, full stop. That's where I learned that intentional cultures yield outsized returns time and time again. We were winning in the box office. We were winning at the award shows. More importantly, we were winning with our numbers. Not only were we making something that we loved in a way that we loved to make it, we were also incredibly successful financially. Those durable, outsized returns that we were able to create have everything to do with the intentionality behind how we decided to operate.
- [11:50]
Interviewer/Host
What was it like working with Steve Jobs?
- [11:53]
Caitlin Holloway
I had the privilege of meeting Steve later in his career, before the Disney merger acquisition, after he was sick. The Steve that I got to know that really helped shape who I am today in my career, he was a softer version of Steve that drove all of the incredible change and technology that we all know him for. Despite having multiple jobs, he was so present in the studio and cared about everything. When we redesigned our studio in Emeryville, he was there every day. He took each one of our senior leaders and he took him to the middle of the studio. This was the heartbeat of our studio, the common area. He pointed up and he said, see all of these windows? See all of those rooms with the windows? They're all looking down on this space. Because I never want you to be having a meeting in a conference room, making decisions without looking at the people that's going to impact. That's how hands on he was. He was in the right weeds. He still drove hard and gave critical direct feedback.
- [12:56]
Interviewer/Host
What led you to decide to leave a job that you so deeply loved around people that you love so much?
- [13:03]
Caitlin Holloway
It's something that I've become good at leaving because a lot of people don't. That's been deeply transformational for me. I left because I loved it so much that I wanted everyone else to have the opportunity to love their job as much as I did. That didn't mean vacating a position so someone else could go and experience in that one place. I wanted to take what I had learned and the way that company worked. I'd had so many jobs at that point in so many different industries, and this one was starkly different. So unique. What if we took some of these things, the magical ways of being really thoughtful about every step in the process, where we put people at the center of every system by design, in service of yielding outsized returns. That triple bottom line where you can have your cake and eat it too. What if we cared about people, the systems that supported them, and we translated that to business results? What I wanted to do was pack up my little backpack with all of that Pixar fairy dust and move into the world of young tech startups. What if we took all of the best of those things and applied them to a really young organization? I spent 10 years. That next chapter was a decade of this HR revolution. Dragging HR out of the back room, into the boardroom, treating human capital as a strategic asset rather than a cost center. My first tech company was a little company called Clout. I spent four years there falling deeply in love with the people that I worked with and how we were doing it. I was so lucky to have a boss there, a partner there. Joe Fernandez was our founder. He let me lead. I had this idea. He let me turn up the volume to 11. It was an inflection point, not just for our company. It helped shift the entire industry. That was a wild ride and I loved it. So I quit. My grandma always said, Katie, recognize when your cup is full. You were meant to be with people and have these moments in your life that teach you something. When you have achieved that, make space to teach others. Moving from clout becomes that next beat. That was impactful for me was late 2015 when I joined Reddit. Now I'm a seasoned operator executive. I had the wind at my back in terms of helping organizations change. I had this full operating model for how to build, repair and scale human systems and I walked into a mess. Every single person told me not to take that job. I thank my lucky stars every day that I did four years helping lead that turnaround as one of the first executives that they had hired on there. It changed everything.
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Sponsor/Advertisement Voice
I'd love to hear maybe in that
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Interviewer/Host
experience at Reddit about those systems to repair, in this case, build and then scale a business.
- [15:46]
Caitlin Holloway
There were so many things that I learned at Reddit, both online and offline. We had a product online where you could find your community for anything. People were self organizing and self governing within these communities. That was so healthy. Not necessarily healthy topics all the time, but the systems that they were operating within were very healthy. One of the first things I noted when I came in was that While we were able to support and help these online communities thrive, we were very bad at taking those same principles and turning them on ourselves and using them as a scaffolding to have our own thriving culture offline. At the time I joined, we'd had three CEOs in less than a year. This was prior to my tenure. The original founders had just come back. Alexis, my now partner. It was a team in crisis. There was a cultural crisis, a financial crisis. There were so many things that were broken within this company. This wasn't my usual playbook of come in and build and scale. This was a complete tear down and then rebuild. And the team was fatigued. They were 10 years old. Revenue was small and dropping. Being able to come in and be curious about what had happened, understanding the legacy of that business before taking a torch to it and burning it to the ground was critical for our ability to reset and then eventually build to the point of success that it ultimately achieved. Something that we learned early on was that you can't scale product faster than you scale trust. Taking that pause and that beat in those early days when I first joined, we had 75 employees. When I joined, I sat down with every single one of them. Multiple hours listening, trying to understand what had come before. A lot of investors that have a lot of capital at stake come in and it's easy to point from the outside in to just say cut the team in half, reduce it to whatever, preserve, burn, and then fix it. Most crises, the investor lends his financial. The solution at that point, from their perspective, was tech. Yes, we did need to rebuild our technology, therefore that would impact revenue, et cetera. Those were metrics that were suffering. What I learned were most crises within that organization weren't technical. They were human systems breaking down under growth. The churn in leadership. It was our opportunity to focus. My initial charge, despite being told by the board and investors that it was to fix it. Add, process, do this, create the right systems, grow this company up, mature this company. My job wasn't to add process. It was to restore social contract. From there. Once we healed and once we identified those broken parts that oftentimes get dismissed or disregarded as being soft, you could only then do that real high leverage work within organizations. It was a complete rebuild, top to bottom.
- [18:39]
Interviewer/Host
You come into the organization, it feels broken. What do you do to get morale moving in the right direction?
- [18:48]
Caitlin Holloway
After you listen, you have to find the pattern of what drives people. Every single person at that company when I joined was there for a different reason. Therefore, no one could Thread the needle on what would move them as a group, what would move them to change and want to invest in anything new, was so fractured. My first strategy was to find that point of alignment. They retired. This was a group of people that didn't have a lot of turnover in that first decade, which was crazy. They all were there for a different reason, except for one, their love of the community. Each one of the employees in those early days, they were Redditors first and foremost. Not meaning people that work at Reddit, they were Redditors. They lived online, they cared for their communities, and they felt an alliance and allegiance and a accountability to the communities that they were a part of online. What I realized quickly was I had to translate that online experience and what mattered to them online, to our offline experience, to our work culture. There were several things that we did that were impactful. I'd asked everyone, what do you call yourselves? At Clout? We were the Clout laws. You have to have an identity. Every community, every group of humans, humans wants to commit to something. Part of that is, how do you identify? None of those employees identified themselves as Reddit employees. That was a problem. I held a number of workshops in brown bags, working sessions for people who cared and people who were curious and interested. I asked them to identify themselves. At that point, there were no values. This is work that's often dismissed as soft. The criticality of bringing people together. What motivates you, what drives you, why do you show up every day? Otherwise go do something else. The thing that drove them was this commitment to community. Then I could thread the needle and start weaving the web between everyone to say, this is also a community. Once we establish that, you establish the norms of that culture, you establish the rule set of that culture. It was everything that they were teaching other people how to do online by saying, who's going to be our moderator and what are the rules of engagement and what is not acceptable and what is acceptable. And this is how we engage around different topics. I took the playbook that they already had and applied it to us. That dynamically changed people showing up to work every day, therefore the quality of work that we're able to produce. Following that, we finally started to see a turn in the business.
- [21:15]
Interviewer/Host
How did that experience lead you from going from an operator to an investor?
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Caitlin Holloway
It was a really obvious next chapter. For everybody else, it felt like a 90 degree turn. Anyone looking outside in when I knew my cup was full. At Reddit, I loved everything about that job. I loved the humans I worked with. I loved what we were able to create online. There was no bit about it that made me disconnect. What I recognized was our business was developing. You gotta have some self awareness. I know that I'm not a public company girly. I knew that after we were acquired by Disney and we finally got incepted into that machine. God bless them. But public companies? That's not my place to shine. Reddit was preparing to ipo. That is something I had never led a company through before. I had taken the company to the place the best I could to prepare for that and I knew that it was time to pass the baton and bring in someone who knew how to do that. It was a happy parting. That was the business rationale. My cup is full. If I love it, I have to let it go and let it thrive and have that best possible chance for success. And it did. That team that came after me was seller. How that translated to investing for me is venture felt so natural. Here's my secret Ted early stage investing is fundamentally about people and systems under conditions of extreme uncertainty and distress. After a decade of operating as an HR executive and helping companies from inception to hypergrowth and blitzscaling through eventual exit, that pattern alignment of playbooks I was using to support organizations. Turns out it was an exact match to growing and supporting a portfolio of organizations. I developed this thesis that if early stage investing is akin to every HR process that I was the godmother of in this new world of people and culture, why aren't there more people who look like me sitting on the other side of the boardroom table? Every board that I sat on, every time I showed up, I was looking in the face of investors who were very smart at things that I was not very smart at. Which is good. That's what you want at your board table. But there was nobody like me in most of those rooms. When I say like me, I mean people that understand nodes and network. If you break down early stage investing, there's some simple buckets. There is sourcing, which is how do you find the best founders in the world? That is the same as recruiting. We use the same word, sourcing. How do I source the top talent? To understand sourcing, you have to understand community. You have to understand network. That was something that I'd been doing for over a decade. I knew where all of the top talent in the ecosystem was moving, and I also knew which ones were loose in the saddle that had been at large organizations or small ones that had an idea being dialed into that underground system of where and how talent moves. That was my source of finding founders. The second bucket in early stage investing is selecting. You have access to all of these incredible people. How do you make sure you're picking the very best? Well, again, this is a recruiting function. You're recruiting for a particular role. VP of engineering. How do you make sure that you're picking the best of the opportunities and people in front of you? That's when the behavioral science background comes in. I've hired tens of thousands of humans in my career and I have fired thousands. Understanding what works and what is needed for a particular time in a company's growth and development was easy to reverse engineer. And what are those archetypes needed to make a successful founder? The third bucket is servicing. There's debates about how much investors and our inflated egos can do to change the results of a company. I've spent my entire career enabling people to fulfill their potential. Those three buckets I was an expert in. So if that's what makes a great investor, why couldn't you give an HR lady a checkbook?
- [25:10]
Interviewer/Host
I'd love to dive into how you've applied those lessons at 776 to each of those three buckets. The sourcing piece, nodes, networks. How do you go about it now?
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Caitlin Holloway
One of the best bits of this is that my partner and the founder of this firm is Alexis Ohanian. Alexis's network is insane, second to none. He has one of the largest Twitter followings and social media platforms of any other vc. And what a range of people engage with him. Everything from Palmer Luckey and Joe Rogan to Barack Obama and aoc. Because he represents many things to many groups of people. Very successful founder, game recognized game founders appreciate Alexis perspective because he is a builder. He has failed publicly and he has succeeded publicly. Being the first graduating class of yc. That network is phenomenal. Becoming a partner at yc, starting Reddit, selling Reddit, coming back to Reddit, turning around Reddit, starting his first venture capital firm, Initialized Capital. That track record, phenomenal. He appeals to so many people because he is so engaged. Being the founder of Reddit, he knows communities better than anybody else. His ability to tap into those different variety of networks, whether that is founder to founder, being recognized as an incredibly strong investor and a partner, to being a human, which a lot of people forget about. The way he celebrates his family and celebrates being a girl dad and all of these things that make him human makes him accessible. Sourcing. From that perspective, we have a great foundation and a great bedrock.
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Interviewer/Host
How do you harness all of Those networks and ideas that are either sitting inside of Alexis's head or sitting as numbers on a X account into something actionable for a venture capital firm.
- [27:13]
Caitlin Holloway
Software. This is where Alexis and I have found our incredible partnership and our balance. If you distill 776 to its core ingredients, people and product and how people and product work together is exactly the foundation for everything that we have built. We've been partners for over a decade now. This is our third rodeo. Him hiring me at Reddit to then eventually supporting my harebrained thesis of giving an HR lady a checkbook. He hired me on as an investing partner at Initialized. When we split that firm and started up 77 6, we finally had an opportunity to build a firm the way we wanted to. The starting first principles were we didn't just want a platform to deploy capital, we wanted an operating system. We wanted to be able to scale the things that should be scaled appropriately with technology so that we could preserve our energy doing those high leverage things that are people centric. This is the creative, strategic, empathetic work that we believe adds leverage that could impact the most important part of a company's trajectory. In those early days. Every decision that we make at the firm is downstream of one question, which is how does this help founders win? A big part of that is technology. Alexis has had this idea from the dawn of time of leveraging software to access those nodes in his network in spreadsheets and pull those out. He developed an operating system called Cerebro. Today it's a wildly robust system. Founders can tap in and self service all of the things that most VCs spend their entire days doing. Whether that is spinning up a campaign to reach out to potential new customers, specifically targeting CMOs within a certain sector, or drafting up tweets and LinkedIn posts on behalf of the partners and other people at the firm and to help support with a fundraise going in and strategically saying hey, these are the folks that I'd like to meet. So our network is fully accessible via software to every single portfolio in the company. They can go in and self service the founders that have figured out how to unlock that and use it daily. You can go to our website, 776. Com and the numbers display the work that is done. So there is nothing that our firm does that is not reflected in Cerebro. From phone calls and support calls, everything lives in Cerebro. You can see the receipts of that. The exhaust of that engine that we've built lives on our homepage because Founders appreciate it. How many times have we heard VCs say, how can I help? What they're promising is an introduction to someone, typically from a large list of categories, and making sure that you're talking to the right people at the right time. They have to think about it. Oh, who do I know at Coca Cola? We gotta know someone over there. Oh, your app is blocked. At Apple, we have someone. Can someone reach out to them? No. And Cerebra Adjust is done. Go in, set your parameters, put in what you want, and then, of course, it all gets screened by us. This is not automatic. At any point, we leverage AI and all of the awesome things that we have available to us today. There's always a human component to it, but what it does is it allows our founders to achieve success and unlock doors in ways that we couldn't scale if we had to pick up the phone every time, or if we had to sit and go through the mental Rolodex of things. Cerebro really has enabled us to scale super efficiently, both in terms of our team size, but then also our portfolio and the amount of help that we're able to provide on an hourly basis. It has dynamically changed that.
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Interviewer/Host
How have you thought about. Of the flood of potential things that could come in from your network? How to start distilling both the people and then the ideas or the products, the themes?
- [30:59]
Caitlin Holloway
How lucky are we, Ted, to be in this industry today, at this moment in time, with everything that's happening in the world and everything that is about to unlock, and it is the process of unlocking. I just get so jazzed on the opportunity set that's in front of us. How do we distill it? How do we ensure that we are making the very best decisions? A part of that is that we do lead through ensuring that we have more eyes and ears on things. For example, everyone at the firm is invited to any pitch we take in the pitch process. Because we have Cerebro, we have software. Every individual that attends the pitch puts their notes into the system. And because Alexis is the Reddit guy, it's anonymous. You're rating these things. We have our own system of how we break down what we're trying to distill very quickly. These pitches. In the grand scheme of things, you're not spending a ton of time with founders before you have to make this decision of, are we going to deploy capital here? Is this a partnership that we want to support for the next decade? Plus? We have systems that are built into where we're analyzing and passing judgment on both. The idea is this the right idea at the right time and is the why there? Also the people on our partnership team alone, two of the three of us have deep HR backgrounds. Chris Vanzetta is our third partner. We've developed over the last five and a half years since the firm's inception what we believe makes a truly great founder. Once we've taken a pitch, we input everything into Cerebro. It goes into the backend before our next deals meeting. It's surfacing. Hey, there's high signal here. Our job is to get to truth as fast as possible. How we do that with software allows us to have better conversations and get to the heart of why we're going to rip our skin off for that particular deal or not.
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Interviewer/Host
From all that HR experience, how do you interview people?
- [32:50]
Caitlin Holloway
Part of this is repetition. Alexis has been investing for 20 years. There is an understanding of some of his basic philosophies and principles that he's able to distill quickly to say, is this person open to coaching? How do they take feedback in the moment? How do they articulate themselves? How are they selling? A big part of being a founder is your capacity and your ability to compel people. How are they presenting this? How are they presenting themselves? All of those things matter. We index pretty heavily on founder. That's not to say that we don't look at product or product market fit at all. In those early conversations. You have to have the right idea or what is a thoughtful idea at the right moment. We're all builders, we're all operators. We understand that a product is going to change 16 ways to Sunday before any liquidity event. What you're betting on is a soft part of the idea on that founder. The more I can build in dialogue that isn't status quo, isn't what every other investor on earth is asking them. I recently seeded a company called StarCloud. The founder is Philip Johnson. When I met Philip, it wasn't in a traditional pitch setting. We were at a conference meeting. Founders at conferences is super rare. But Philip was one of the most interesting people I had met in a very long time. We got seated next to one another at a dinner. We introduced ourselves. I had never heard of StarCloud. He had never heard of 776, Alexis or me. We started talking about things that were personal to him, some life milestones that were coming his way. I started asking him questions about the time space continuum and his thoughts on wormholes and weird things like that. And over the course of this dinner, I had a clear understanding of how Philip's brain worked. I have a clear sense of his value set, how he treats people, and how he expects others to treat one another. At the end of that dinner, I was like, what do you do again? That's what he said, oh, we're building data centers in space. And I said, philip, I don't know if you're raising. When you're raising. I have no clue what you're up to. I want to be a part of it. And if you're not taking capital or your round is closed out, if I could be of support to you, I think that you're it man. When you know, you know. Which is a terrible answer to how do you know? In that example, I walked out of there and saying, I don't give a rip if Philip is making dry dog food. I want to support Philip. He's going to make something incredible happen. I brought it back to the team. At this point in time, data centers in space was audacious. I got dragged so hard internally and externally for even asking about it. I was doing my diligence. I started asking people, what do you think about this? I was talking to founders of big, important terrestrial data centers about it. They dismissed it. People were salty and nasty about it. I kept coming back to the table. You gotta hear me out on this. They technically were not raising anything. I kept in touch with Philip. I kept my foot on the gas. I had such high conviction. We were able to get an investment done with him before the world exploded. With the love and support from Elon to Sam Altman to Jeff Bezos, anyone who's anyone. Within a month of that check that I was able to finally deploy into Philip and his merry band of space guys. They are now on such an incredible trajectory. That's a wild example. That was not. You've sent me an inbound and now I'm going to meet you. And then here's the team. And then this is what we think now. We're going to move forward. I won't give it to serendipity and luck, but my favorite way of getting to know founders is having conversations sometimes that have nothing to do at all with what it is they're building. And then eventually getting here,
- [36:33]
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- [37:26]
Interviewer/Host
How do you balance this deep focus on the person, the entrepreneur, with what it is they're doing? Is it a good market to be involved with? Do you have conviction on the theme that they're pursuing?
- [37:40]
Caitlin Holloway
If someone is showing up, they've got all of the right signals or signs that we believe is destined to be a great founder. But they show up with an idea that is so wildly off the mark from our perspective, our limited worldview. It's a do not pass go. There are plenty of people that I've met that I like. You've got the goods. But I'm not going to write a check because they were not barking up the right tree at the right time. You have to be within spitting distance of solving a problem that collectively makes sense to the firm. Something else that I really appreciate about how we designed 776 is that we are generalists. Back when we started this up there were questions from LPs, sometimes even founders. Why aren't you focused? Why aren't you going to be specialists? This is where I really lean on. Alexis's experience when he was building initialized with those partners. They were generalists because it was a less formal working group. In those early days they were still a part of yc. They were cutting checks into people that were hanging out at the same watering hole. As a result, you have such a unique variety of companies that move the needle, ranging from Coinbase to Instacart, a handful of others. It was a smaller fund that shaped and crystallized Alexis's philosophy and belief that he would always want to be a generalist investor. That is something that we knew we needed at 776 when we started. The spread of company type is awesome. You've got an incubation with a company called Athlos that is a track and field league right now focused on women. That was Alexis's brainchild. We have almost complete ownership of and was brought to life from an idea to now being a full fledged league. Changing the culture of track and field, hitting and making milestones like the largest purse prize in history for some of These athletes to a company that I invested in recently called LambdaVision. They're manufacturing artificial retinas in zero gravity that could feasibly cure all retinal disease. That is a wild spread. And the context shifting that we get to do every single day, Athlos to Lamb division and everything in between. That is the exciting part where I feel so lucky to be in this industry at this time. While Alexis and I both have our own interests and proclivities, as does Chris and other members on the team, our thesis lies more in the founder. We want to meet the very best founders exactly where they are, solving the problems that they think are most critical and most urgent for humanity. That's what we're seeking. At the end of the day I can look back at Fund 3 and say, oh, here were some trend lines or things that it was obvious we were more attracted to in that moment. But the reality is we're still looking for the very best founders.
- [40:29]
Interviewer/Host
What are the frameworks you might use to screen out things in a very, very wide remit?
- [40:36]
Caitlin Holloway
As a generalist, I don't think that we have any hard passes on any particular industry. Every single check that we write, we underwrite it to return the fund full stop. We lead deals. We have ownership targets. Those things are non negotiable. There's the rare event where we meet somebody maybe later or the stars didn't align and we might meet them later in their process and it doesn't exactly fit into our model or the ownership is simply not left but we still want to be able to participate at that particular moment. We will write a check that doesn't meet our ownership thresholds, but that's pretty rare. We do that with the explicit conversation with a founder of we're doing this now so that we can earn the right to underwrite your next round so it's never a little one off, itty bitty check. It's not spray and pray. It's very high concentration, very high conviction. Sometimes that negates us from deals entirely. Some companies are good ideas with great founders that are not venture backable businesses. Our core principles of being great fiduciaries. Honoring our commitments to our LPs is important to us. There's a ton of thought that goes into it. That's the first filter. After that there's no industry filter or business type filter.
- [41:48]
Interviewer/Host
Once you have made an investment in a company, that third leg of how you help them. We'd love to hear some of the challenges that the founders you work with typically face. As they begin to grow their businesses.
- [42:02]
Caitlin Holloway
This is my favorite part of the job. I love the thrill of the hunt. I love meeting new people. The best part is that now I get to work with Philip and his whole team who I've grown to deeply respect and get excited about every day. I am lucky to be a part of their journey. This is a relatively new investment. I don't have a ton of hours clocked boots on the ground with this particular team yet. We've been around for five and a half years. I've been an institutional investor now for seven. The relationships that I built with people through the hardest parts of their jobs, their lives, their work have been absolutely life changing. I've seen success, I've seen a lot of failure personally and through our portfolio. That's the power law at play. I view one of my primary roles as a partner to any founder is to not tell founders what to do. I am never directive suggestive, always. A big part of my job is to help them ask better questions. The more I can help a founder stay in a place of curiosity and growth, the better their product is going to be. The better they're able to connect with the people that are doing their work and bringing their vision to life. I default to my operational skillset a lot. It's unusual to have someone like me on a cap table. I'm the one who fields the 2am phone call from the back of a waymo when someone says we're wrapping up a company event and I think that my fill in the blank executive maybe just stepped out of line with an employee and I don't know what to do. A lot of VCs don't get those calls because VCs are designed to maximize for upside, they don't have the experience to help manage real risk. Financially, yes, but human work? No. It's my sincere belief that human capital work is risk management disguised as empathy. This idea somehow along the way life, business, society has decoupled business outcomes or even capitalism from humanity in a way that is incredibly destructive. When I reframe this idea that doing that human work is actually risk management disguised as empathy dynamically changes not just my relationship with individuals, but our collective relationship with the business.
- [44:23]
Interviewer/Host
What are some of the answers to sticky situations like that?
- [44:27]
Caitlin Holloway
This is why I'm not scared of AI creating mass unemployment, in that I think that our work as humans is being reshaped. The answer to your question is it's different every single time. Details matter. Nuance matters. Context matters. The players in the game that are involved matter. All of that impacts how you might guide someone through something. In my career, in 20 plus years of supporting humans in an organizational way, my partner was just diagnosed with something terrible which has come up multiple, multiple times. Fill in the blank. Divorce, death, all of these things that are very human that handbooks and HR policy doesn't cover effectively, that really matters. Having those conversations, knowing the individual as intimately as I get to know them by design, will change how I support them through something outside of work, but deeply impacts their capacity to show up as a great leader. In some cases, the answer is let's figure out succession. In other cases it's how do we help bring in support right now to help you be able to focus on your most immediate and most precious need, which is the person you love. How do we keep the business on standby for a moment at 776, we have a program that I'm proud of called our Growth and Caregiving Program. It's my belief that the best founders on earth care about their businesses so much they're always willing to put themselves last, just like a parent and a child. The reality is if you don't put your oxygen mask on first, you cannot help and save your child. We've created this financial program where we give grants. It's a separate pool of capital outside of the investment made for your first check in that we write at pre seed and seed stage that allows for you to have access to dollars to support you. If it has anything to do with your personal growth and development or anything to do with you supporting or caring for the people that you love most in life, please tap into it because I know that you're not pulling that off your balance sheet. Those more human scenarios, it's different every time. Things evolve and develop in ways that we can't predict. On the other side, where something maybe is more of a complex decision around termination, values alignment, these are things that you can't chat GPT your way out of. This is sincerely where I believe our
- [46:49]
Sponsor/Advertisement Voice
work is evolving as a company is growing.
- [46:52]
Interviewer/Host
You've interviewed so many thousands of people. What have you found or some of the lessons you've taken away that you help your founders with about how they should hire into their businesses?
- [47:04]
Caitlin Holloway
Many successful venture firms have a talent team or a talent department where they are more or less glorified executive recruiters that don't have the autonomy, the context or the resources to really effective help companies scale and bring in top talent. But it is a solution. I'm not poo pooing it entirely. I'm standing up for the talent partners within other organizations from my seat in the house sitting on the other side of the boardroom opposite of investors. You look at the data of executive hires placed by a venture firm. Either an investor says like oh you got to hire this guy. He's going to come in and totally change your go to market. This guy's going to blow revenue out of the water. Or it's through a talent team that is helping you source and place these senior leaders. The data speaks for itself. The tenure is less than 18 months. Most of these people come in the body rejects the organ. They're incentivized to get to that first year of vesting that equity because they've been given sizable grants. It's not worth leaving before that. So they hang on. They sow cultural divide. Their total mismatch for what the company is doing not because they aren't great at what they do, but because they were not hired by the organization itself. You as a founder should be a part of your hiring process until the day you exit. Full stop. Founders who are disconnected from building the team that is designed to help them fulfill their potential, to realize their dreams, to capitalize on all of their brilliance. If you are disconnected from that, you're not going to make it. That is something that is not said often enough and something that a lot of investors and VCs haven't quite groked. The best founders I know never stop interviewing the great founders. The best organizations are constantly hiring. It doesn't always fit into a particular job spec that was posted. We're actively hiring for Rolex. The best leaders, they're constantly seeking connection with interesting people. That person that you talk to today might not be or fit any open job you have now. You might even be doing layoffs. I want you talking to people constantly. I want you to understand who's thinking about what. This is not just related to that curiosity piece. Cause that's what makes you better. Stronger. Iron sharpens. Ironically, it helps you understand what is available to you when you are limiting yourself to I just posted a VP of engineering job and then you're in that precise interview cycle. It's like finding an apartment or a home. If you haven't been searching for that apartment or home. Preparing for that moment when you know that's going to be time to pull the trigger. You only have what's available to you in that moment. How foolish would it be to not have been thoughtful and fantasized what might be available? Even if it's not that right moment to make that higher or it's not going to be on your roadmap for a significant amount of time. Having your finger on the pulse of great humans is only going to make you better. Whether it's you're taking a piece of advice from a conversation and that is additive to your business, or forging a great relationship that will build over time and you can capitalize on it when the moment is there for you. Anyone who thinks that interviewing should be left to a other people and then b only when it involves you or an active need that you had, you are missing out on 90% of the opportunity.
- [50:29]
Interviewer/Host
What are some of the other characteristics you found of great leaders?
- [50:33]
Caitlin Holloway
There are several and they are different amongst them. Specifically as it relates to building a high performing organization. Something that I tell people a lot is Hire when it hurts. Do not hire until you have been doing that job yourself for several months because one now you know how to better hire for it because you've done the job. And I'm speaking specifically about early stage. When you're building something, not only does that build that better understanding and articulation of the role that you need to fill, it also breeds sincere empathy for what that person is walking into. You can be a better leader to them, a better support them to get their job done, then the relief that you will feel and the brain space that it opens and allows for and lets in dynamic space for innovation and creativity. Higher when it hurts. It's something that I've done for the last 20 years at every company I've built every time I've compromised on it. Failure exists in meaningful ways. Alexis and I do that at our own firm. It's what we tell our founders to do. It breeds so many more positive things than negative. What can I do instead of airdropping in Senior executive bozo number 25? My job is to help you learn how to hire really well. If I can help our founders and then subsequently their leadership teams learn how to get really good at hiring and then really good at firing, my work is done. That impact is going to be far greater than me bringing in Joe Schmo. He was at Google for 20 years. He must be the best. I'm not saying if you're at Google for 20 years you aren't going to be the best. There was a pattern recognition thing that VCs were doing. Now they're using hypercharged words around. You're not a 10x or anymore, you're a hundred xer and blah blah, blah. This is the idea of teach a person to fish.
- [52:22]
Interviewer/Host
What are the lessons that you're teaching someone to make them great at hiring?
- [52:26]
Caitlin Holloway
One of my jobs is helping founders retain that sincere curiosity around everything. But it most certainly applies to hiring a great team. In a lot of these cases, I'm working with the broader leadership team as they grow and scale to help each one of them learn this skill set as well. Having the founder focus on more behavioral questions that are in alignment with their cultural values and norms. What happens is the company has hit that inflection point, maybe Series A, we have product market fit, we just got a huge injection of capital. I'm going to go hire like bananas. I'm just going to hire a ton of people because oh my God, we have so much work to do. I understand the instinct, but it's wrong. What happens is you have other people at this point that are screening and fielding and bringing talent into the pipeline. By the time a candidate gets to a founder or a CEO, because they typically were great operators, they oftentimes go back into that mode of early day hiring. So technical questions, getting in and saying, can you do the job? Are you really the best person to do the job? We translate the interview questions and the intention from tell me about how you work instead of tell me what you do and tell me why you're qualified to do this. It changes the nature of that conversation and therefore the results. Some founders are good at analyzing those results, others need more support around what signals am I looking for or where do red flags stand out or what do they feel like? What are the green flags and how do I move on those quickly? There are some basic systems you put in place and the groundwork that you can do ahead of the interview. Systems around compensation practices and philosophies and all of those things that help you move faster. Then focusing on behavioral science, getting our founders sharp around that is important to me.
- [54:15]
Interviewer/Host
The other side of that is someone not working out. And there's both an assessment piece and then a letting someone go piece. And would love you to share some of what you've learned in both of those. The assessment and then the action.
- [54:31]
Caitlin Holloway
The biggest mistake I see founders make is they don't move fast enough. Never once in my multi decade career of hiring and firing people and supporting founders and entrepreneurs and builders has anyone ever come to me and said, I regret letting that person go. What they do say 10 out of 10 times is, oh my God, I should have done that sooner. The muscles that I help build within organizations is how to move faster. It's not because people don't know how to identify it or how to assess it. Almost all people know there is a spidey sense, there is a direct work result. There are failures that line up to that. There are points of friction that don't go away with logic or with clarity. You know when it is not working. How do I help you move through the assessment phase to the action phase? In the early days for a founder who maybe is less experienced, first time founders, oftentimes younger founders that haven't worked in other industries, they are so careful and cautious, so risk averse because they're worried about optics, they're worried about the impact to the human, they're worried about compliance, they're worried about so many things that they prolong the pain and compound the failure. The faster I can get you to move and feel comfortable with making the decision. I will write scripts for people who have never fired someone before. I will sit down, I will coach, I will say, okay, how are you going to say this? What do you say if they say that, how do you go through this so that I can help them build confidence to move quickly? It never gets easier. As a human, I'm not saying boom, go in and execute. It's no big deal. If my founder doesn't have empathy or doesn't have feelings about this termination, they probably shouldn't be a leader anymore. I'm not saying that you remove the emotion from it. I'm just saying reduce the emotion of the impact to your team and to your business and to your business results and your own mental load and the load of the person. Brene Brown clear as kind man. They know it's not working too. The kind thing to do is to be as clear as soon as possible and and let them go. Every minute they're sitting in your organization. Compounding those failures for both of you and your business is a day they are not investing equity in a company they love. Rarely when someone exits an organization do they wind up in a place that is worse than the situation they were in with you. That's a part of the ego death for founders that is important to understand and learn too. If it's not working for you, it's not working for them. And if it's not working for either of you, it's not working for your business. How do I help you get there faster?
- [57:10]
Interviewer/Host
What are some of the experiences you've seen when a founder goes from effectively controlling everything in the business to needing to bring in say a Leadership team and delegating out different tasks.
- [57:22]
Caitlin Holloway
This is one of the harder initial inflection points from a founder, development and growth standpoint. Depending on how the business develops, companies will peak in valley at different times. Sometimes with those peaks and valleys, there comes an expansion and a contraction. The crazy part is that a lot of founders think that once they successfully cross the chasm, the first time of, oh, that was really hard. But when I finally was able to push that decision making and that autonomy and that accountability down through the organization, that was hard for me. I made it to the other side. They don't expect to have to do it again. And so they forget that lesson. Oftentimes there is an expression of expansion and contraction. Sometimes that's in headcount. Physically, you actually are pushed back down into the weeds because your team had to contract. Oftentimes it's a business need expression of expansion and contraction. Maybe you are needed on this particular thing because revenue is suffering, something has shifted, something has changed, and what was working before is not going to work now. So you have to come back down into the weeds. How do you then gracefully reintegrate yourself into a system that you expressly have said, I should no longer be a part of this? It's not just that first time that you have to coach founders through this beautiful growth moment or milestone in their own careers and in the company's development, but you have to help them do it several times because it also looks different with scale, success and failure being that layer. It is hard. Having built 776 from the ground up. We're five and a half years in. There are two a.m. moments. I had one last night where I'm sitting there staring at my screen going, why didn't I delegate this? What about this did I think was so precious that no one else could do it? I have a stellar team. I built this thing with Alexis in our bare hands. I've hired people who are way smarter than me by design. And I'm sitting here at 2am cranking on some dumb thing. What's wrong with me? It is a lesson that you have to continue to learn time and time and time again. The reward and how you move through it is when you challenge yourself. When you see yourself falling out of that practice like I did last night, I challenged myself to say, why? Why did I have to white knuckle this stupid thing? Why did I box people out of this process? And when I could articulate to myself like, well, because I care about this particular outcome, or it's because I'm deeply committed personally to this founder. Or it's because the context is here and sharing it with someone would take longer than it would be for me to just do the thing myself. Whatever the thing is, identify it, name it, share it with the people that you should be bringing into the process. Own it humbly and take accountability for your being asinine about something. Watch them do it way better than you. Name it for the next time it comes around and say, hold me accountable to that. If you see me doing this, call me on it, man. Chris on the team, he'll knock on my door, he'll say, I saw you were in that document last night. Caitlin, what are you doing? Thank you for saying that. I'm a reward based individual. When I do challenge myself to let something go or to push it down as I'm supposed to do, to let it go and trust my colleagues, the reward is when they kill it. When Chris comes back and says, I spent a few hours noodling on this thing and this is what I came up with, the reward is saying, oh my God, that's such a better solution than what I was banging my head against last night. Thank you. I want that dopamine hit 10 out of 10 times. It exists, it's pervasive, it doesn't always go away. We can learn to be more aware about it.
- [60:52]
Interviewer/Host
When you start backing someone at the early stage and you've seen that pattern of those initial stages of growth of a business over and over again, how do you think about continuing on and supporting them in later stages of growth
- [61:06]
Caitlin Holloway
as an outsider for so long to the world of venture, being on the other side of the table as just an operator, I thought it was interesting. A lot of investors are bad at showing up in the early days and the really hard times when things are super messy and icky, things maybe aren't going well or they're going well, but you're just grinding really hard and they pop in and give you a very empty, how can I help? Then when things start to go really well, when you hit that inflection point of success, the rocket ship is starting to take off. Suddenly they all show up. And the irony is that's actually when you need them the least. I have a bias against how I think most of this industry moves, mostly because it's ego driven. You have a company that starts to take off and you want to be associated with it. You want to be a part of that good feeling. You're rewarding yourself for picking well and spotting it and oh my goodness, the carry check. Let's all get down with dpi. Yes, I'm here. I get it. I get how we get there. Our firm is still young. Our oldest fund is only five and a half years old. One of the first checks that we wrote into a space tech company and one of the first checks we wrote as a firm was into a company called stokespace. That CEO founder Andy Labsa. If I could copy paste that dude, I absolutely would. His co founders, phenomenal. When we wrote that check, just like my story with StarCloud, people were like, what reusable rockets you're going to take on SpaceX? That's a very interesting decision. They are one of the hardest working teams that I've ever come across. They're not just building and shipping software. These guys are building real rockets that are not designed for their maiden voyage every single time they go out. They're designed to be durable and lasting. It's literal rocket science. We had the privilege of partnering with them early on. We, just in case this isn't clear, are not rocket scientists. How do we show up? I don't even know how we can be helpful. They just closed a massive round. They are literally going to the moon. This is an incredible success story at this stage of the game. I was chatting with Andy, I was like, how lucky are we that we got to meet when we did. What a privilege it is to watch you fulfill your potential and do these things. The opportunity to unlock not just technology, but be the infrastructure, the logistics for an entirely new economy is what a charge, man. You are doing incredible work that I am so deeply proud of. He looked at me and he was like, Galen, you forget how hard it was in the beginning. I haven't forgotten that a big part of our help wasn't just our dollars. It was your conviction in us. You guys believed in us long before anyone else thought that it was viable. We were building rocket in Tim's front yard. Why are you thanking me? Andy and his team's needs in the beginning were really different. I remember taking calls with him about his parental leave policy, talking about how can they build out an office space that supported better work life integration but still help keep people focused on their mission at hand. I remember driving out to eastern Washington to a frickin dirt lot when they did their first test fire. What they needed from us was to show up. That's the easiest thing that any of us could do. Have the same mystery and wonder and excitement about what it was they were doing and just know that we were there. I'm not going to tell them to tweak this or that or turn that burner down or launch that thing up or just add a little bit of hydrogen here. No, I can't do that. But I can help you navigate what it's like to still be underestimated. Now, with all of their successes, Andy can't keep them away. His help now is very different because we built that relationship and because we had the closeness in those early days. Have the same reaction when I see his name pop up on my phone or I get a text or a ping in Cerebro. Yeah. What can I do with your history
- [65:02]
Interviewer/Host
and beliefs that at some point in time your cup gets filled and it's time to move on? How are you thinking about your trajectory from here after five and a half years at 776, I feel like I've
- [65:15]
Caitlin Holloway
lived 17 different companies within 776 in the last five and a half years. I don't know if it's possible for my cup to be filled here. The beauty of founding this firm with someone like Alexis. We're very different leaders. We have very different strengths that speaks to the strength of our relationship. He has the capacity to see around corners that other people don't even know exist. He understands communities intuitively. He has a wild sense of timing. My strengths are more about reading people, systems, incentives, psychology, empathy, execution under pressure. But we don't try to be the same kind of leader or the same kind of investor. We trust each other to be excellent in very different ways. What makes him a great partner for me specifically, is that he does take the things that I value very seriously. The core of that is people. He takes founders, operators, athletes, anyone who comes into his orbit. He treats their work and their ambition with respect. He's willing to back conviction early and stay patient when things take time. Patience is rare in our industry. I think this cup is really big. It can hold a lot of volume. It changes every single day. The amount of shifts and changes and evolutions that we've gone through and what Alexis and I personally have gone through. I know this is my life's work. It's going to take on several iterations that will solve and satisfy that question around, do I leave it when I love it the most?
- [66:49]
Interviewer/Host
As you talk to Alexis about what's coming around the corner, what are you together hoping to achieve? For 776, he and Chris are flying
- [66:59]
Caitlin Holloway
in for our executive off site, which is something we do every 90 days. We work remotely, bringing the three of our noggins together as our current leadership team. To talk about this on a consistent enough basis is really important. When you're a young company that is as hungry as we are and as driven as we are, our appetite for growth and development is insatiable. The conversations we're having are not around what should we do? Or what can we do? The conversations are actually what should we not do to really ensure that we're focused on the long game. In the midterm view, when I look down the next three to five years, it really is to just continue to develop the portfolio, to continue to develop the team, to continue to be at that moment, at the zeitgeist, living on that bleeding edge of what is next. What makes it different for all of us is that we're at such an important moment in time. You've got a generational shift with Gen X and elder millennials coming face to face with a lot of life, a lot of unfulfilled promises and careers built, oftentimes not to the extent that everyone had hoped and dreams. You add to that economic pressures, raising small children and growing adolescent children and now managing parents that are perhaps ill or passing. It is landing at this moment of massive technological shift. This is a platform shift that we are living through. You're watching the tidal wave and it is here. Our biggest charge right now as an early stage VC firm is not to just continue the job that we were entrusted to do by our partners and our commitment to ourselves and our commitment to our founders. It is to ensure that we are stewarding this change and this shift in a thoughtful, intentional, values aligned and gracious way. Life as we know it. It is actively changing. Being present, being thoughtful, the readiness to be able to capitalize on these moments and on these opportunities, and not just as investors, but as humans, to make sure that we are being thoughtful. As this next chapter is being set for generations to come, we have a big charge to help shape that outcome. It's our responsibility. There are firm goals, there are firm wants, dreams, desires, all of which are more audacious than the quarter before. We have to get good at being focused and knowing what to say no to. Then there is the more global galactic challenge of making sure that we're being great stewards of this change.
- [69:34]
Interviewer/Host
Kaylin, before I let you go, I want to make sure I ask you a couple of fun closing questions.
- [69:39]
Sponsor/Advertisement Voice
Before we get to the closing questions, I want to tell you about one of our strategic investments. We've made a few and each are working on a product or service we
- [69:48]
Interviewer/Host
think will be valuable to our community.
- [69:50]
Sponsor/Advertisement Voice
One is Oldwell Labs or owl. OWL is the very best software I've seen for allocators to find and track managers and I've seen a lot of them. Trust me, it'll be worth the look. There's a link in the show notes so you can learn more. And here are those closing questions.
- [70:06]
Interviewer/Host
What is your biggest pet peeve?
- [70:09]
Caitlin Holloway
I have two One is confusing motion for progress. The duck analogy. I hate it when people are just busy and they're operating at low frequency because they aren't able to distill the critical leverage from critical mass. You're doing too much. You're not doing it well. Knock it off. Nine times out of ten I'm the one who has to clean it up Sometimes I'm talking about my children when I say that that's not just work related. The second one is I hate when people accuse me of not being thoughtful where they ask questions. That insinuates that I have not completely 1000% overthought in every single Doctor Strange 10,000 possible iterations of outcomes and trade offs and every single detail of every single event that has ever happened or will ever happen. Super insulting.
- [70:56]
Interviewer/Host
What's a mystery you wonder about?
- [70:58]
Caitlin Holloway
I've talked a lot about space. It's obvious that I'm interested in how things are changing with this evolution and this opportunity for humanity to go off planet as I become better acquainted with people who have gone to space. The perspective that gives humanity. This is a mystery that I think about way too much is this idea that time might not be linear, that it actually folds on itself and potentially exists all at once. That negates the idea that cause and effect are structured in the way that we think about it, that the time space continuum is cohesive as opposed to linear. And then you couple this with this new theory that our galaxy is living inside of a black hole and how that might impact the way time is currently moving. I could go very deep on that, but that is a mystery I think about a lot.
- [71:47]
Interviewer/Host
Caitlin Last one.
- [71:48]
Ted Seides
How's your life turned out differently from
- [71:50]
Interviewer/Host
how you expected it to?
- [71:52]
Caitlin Holloway
I don't know that I ever had a clear picture of what my life was supposed to look like. I talked about growing up in Alaska and Stockton. Having expectations of life was a luxury I don't think I had. That's not to say that I didn't have incredible parents who didn't help me have hopes, dreams and desires because of my parents. I definitely had a sense I had something important to do. I didn't really know what it was yet. Instead of planning my life, I mean, you could tell by my wild resume, I stayed curious. I followed the work. I followed the people. I followed the problems that pulled at me. None of the things that we talked about today happened because I mapped them out in advance. They happened because I was open to discovering them. I started to notice as I grew and as I aged that the good things around me started to compound those things that were once in a lifetime moments. They stopped feeling singular and started to feel repeatable, not predictable, but available to me. I do wonder if this was written in some way. Destinates in the stars time folding on itself. We're living in a black hole. The response to Expectation of Life turning out Differently I feel incredibly lucky. I get to do the work that matters to me with people I admire. I live a life I could not have imagined. So maybe not differently, but certainly not expected.
- [73:08]
Interviewer/Host
Caitlin, thanks so much for sharing this very human way of thinking about venture investing.
- [73:13]
Caitlin Holloway
Thank you so much for having me. Ted.
- [73:15]
Sponsor/Advertisement Voice
Thanks for listening to the show.
- [73:17]
Caitlin Holloway
If you like what you heard, hop
- [73:18]
Ted Seides
on our website@capitalallocators.com where you can access
- [73:22]
Sponsor/Advertisement Voice
past shows, join our mailing list and sign up for premium content. Have a good one and see you next time.
- [73:30]
Disclaimer Voice
All opinions expressed by TED and Podcast guests are solely their own opinions and do not reflect the opinion of Capital Allocators or their firms. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Capital Allocators or podcast guests may maintain positions in securities discussed on this podcast.