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

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“In some way destinies in the stars, time folding on itself. We're living in a black hole. The response to expectation of life turning out differently, you 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 can 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 life time moments, they stopped feeling singular and started to feel repeatable, not predictable, but available to me. I do wonder if this was written.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“Two. One is confusion 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, it'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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“Values aligned in a 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 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 way.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“And Chris are flying in for executive offsite, 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?”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“I feel like I've 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 were 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's 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“We were building a 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 freaking 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, burn her 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...”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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, Gaylin, 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Lapsa, if I could copy paste that dude, I absolutely would. co-founder's phenomenal when we wrote that check just like my story with StarCloud people were like What reusable rockets you're gonna 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“As an outsider for so long to the world of venture being on the other side of the table is 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 where five and a half years in there are 2 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 or bare hands. I've hired people who are way smarter than me.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“Is one of the harder initial inflection points from a founder development and growth standpoint, depending on how the business develops, companies will peak and 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 revenues suffer.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Renee Brown, clears, kind man, they know it's not working too. The kind thing to do is to be as clear as soon as possible 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 that they wind up in a place that is worse than the situation they were in with you. That's a part of the ego desk 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?”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 of 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 lying 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,”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 than focusing on behavioral science, getting our founders sharp around that is important to me.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 a broader leadership team as they grow in scale to help each one of them learn the 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 higher 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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? 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 Schmoe. He was a 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 anymore, you're a 100Xer and blah blah blah. This is the idea of teach a person the fish.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 higher 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 and 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, better support them to get their job done. Then the relief that you will feel and the brain space that it opens 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“Thoughtful and fantasize 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“Constantly hiring. It doesn't always fit into a particular job spec that was posted. We're actively hiring for Role X. The best leaders, they're constantly thinking 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 because that's what makes you better stronger. iron sharpens iron. 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”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 grocked. The best founders I know never stop interviewing. The great founders, the best organizations are”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“Many successful venture firms have a talent team or a talent department where they're 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 poop pooling it entirely. I'm not 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 work is evolving.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 precede and seed stage that allows for you to have access to dollars.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. The 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Dynamically changes not just my relationship with individuals, but our collective relationship with the business.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 skill set a lot. It's unusual to have someone like me on a cap table. I'm the one who fields the 2 a.m. 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 have 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. Have you one of my primary roles as a partner to any founder is to not tell founders what to do. I am never directive, suggestive.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“Venture backable businesses are 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 a 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 prey. 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“Like the largest purse prize in history for some of these athletes to a company that I invested in recently called Lamb Division, 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 aflows 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 interest and proclivities, as says 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“A less formal working group in those early days, they were still a part of YC. They were cut in 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 Aflos that is a track and field league right now focused on women that was Alexis' 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 milk.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 design 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' experience when he was building initialized with those partners. They were generalists because it was.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“You got to hear me out on this. They technically were not raising anything. I kept in touch with Philip. I kept my foot on the gask. 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 sent me an inbound and now we're 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 Locke, 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“To treat one another at the end of that dinner, I was like, what do you do again? He said, Oh, we're building data centers in space. And they 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Star Cloud. 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 Phillips' brain worked. I had a clear sense of his value set, how he treats people and how he expects others.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“Support for the next decade plus. We have systems that are built in to 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 back end 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 heart of why we're going to rip our skin off for that particular deal or not.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 jealous 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 cerebral, 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?”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“Scale if we had to pick up the phone every time or if we had to sit and go through the mental rollide decks 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.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 got to know someone over there. Oh, your app is blocked at Apple. We have someone. Can someone reach out to them? No. And cerebral just 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 could.”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source
“Tweets and LinkedIn posts on behalf of the partners and other people at the firm 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”
2026-03-09 · Capital Allocators · Katelin Holloway – Human Side of Venture Investing at 776 (EP.490) · IDENTIFIED FROM THE TRANSCRIPT · source