YouSaid · the spoken record

Katelin Holloway

lines on the record
79
first
2026-03-09
most recent
2026-03-09
sittings or episodes
1
sources
podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

  1. “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”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “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 hair brain thesis of giving an HR lady a checkbook. He hired me on as an investing partner and initialized. When we split that firm and started up 776, 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”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “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”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “Of the best bits of this is that my partner and the founder of this firm is Alexis O'Hanian. 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 Lucky 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's 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 for an initial.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “Growth and development was easy to reverse engineer. 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?”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “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”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “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?”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “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 I 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 stellar, 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 hyper growth and blitz scaling through eventual exit, that pattern alignment of playbooks”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “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 got to 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 inside.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “Leaving 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.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “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 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 Bad's 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.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “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 verse 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 accountability to the communities that they were a part of online. What I realized”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “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 is 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 undergrowth. The turn 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”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “In this company, this wasn't my usual playbook of come in and build and scale. This was a complete teardown and then rebuilt. 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”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “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.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “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.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “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.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “Something that I 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 and 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.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “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 Emoryville, he was there every day. He took each one of our senior leaders and he took them 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.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “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, where EdCat Molt, 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 love 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.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “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 that 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 designed culture as infrastructure. There were consistent, frequent feedback loops.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “Cat mole, John Lassiter, 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.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “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.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “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 was 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,”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “I got good at reading people, understanding power dynamic, that it didn't always match an or chart. It 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 and 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.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “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. Retail hospitality, I worked out in the fields picking cucumbers and green beans, but eventually made my way into things like law enforcement and banking. There are many, many industries.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  27. “I'm going to take you back to the very beginning. I was born in Fairbanks, Alaska, raised in Stockton, California. And 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.”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  28. “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?”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source

  29. “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 hyper growth and blitz scaling 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 Sage 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?”

    2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source