Jason Kirby: All right. Welcome back, everyone. Welcome to Fundraising Demystify. Today, we have Winter Mead with us, founder and CEO of Coolwater Capital. Welcome to the show, Winter.

Winter: Jason, thank you for having me on board and hopefully this is a show where lightning strikes twice.

Jason Kirby: I love the sound of that. Well, you have an interesting background. This is a little bit of a deviation from the typical guests we have on the show. You're supporting emerging fund managers in building and raising funds for venture capital. And I would love for you to tell the audience a little bit about your background and what you're doing at Coolwater.

Winter: Yeah, thanks Jason. The background, pretty simple. Spent 12 years in the Bay Area, worked at a couple of startups, but most of my career has been spent as an LP, a limited partner, investing into managers, fund managers, and mainly emerging managers, emerging venture capital funds. So that's kind of the perspective I'm gonna share on the podcast today.

I worked at a firm in San Francisco called Hall Capital Partners founded by Katie Hall, who was very involved with the Princeton Endowment. So it was a very traditional approach to learning how to be an LP, what LPs would call the endowment model style of investing. So investing mainly into alternatives, but through managers. And so I felt like I took the training wheels off there.

Built a lot of perspective, not only on venture capital and private equity, but across asset classes. Like what are the return drivers? What actually creates value depending on what you're investing into, right? Real assets, public equities, private equities, you know, within private equities, buyout versus venture, like what actually drives value. So I thought it was a good foundational experience.

I moved over to SAP, I helped them build a large fund-of-funds practice, so again, as an LP. But the nuance there was it was part of a larger direct investment venture capital firm team. So I felt like I got both the LP perspective as well as the VC, like the tier one VC investment perspective. And the other perspective I got there was actually as an intrapreneur.

Like an operator within a larger corporation, building an investment fund. And I think that's largely what contributed to creating Coolwater and looking to give back into the ecosystem and support emerging managers because even with a large budget as part of a large corporation, building a very large fund inside of an organization with tons of resources and perspective and expertise—

Winter: It was hard, right? And it took years, it took four and a half years, right? To really feel like it was starting to get dialed in. And so the empathy that created was immense, right? And so I shifted in 2018 to really dedicate my life to supporting the innovation ecosystem. And the strategy is largely through supporting emerging managers. So excited today to talk about emerging managers and why I'm spending time in this space.

Jason Kirby: So you had the fortune and ability to kind of tap into kind of all the different roles in the ecosystem in and of itself from LP operator to, you know, GP. So I think that's a pretty unique perspective that you bring to the table and, you know, led you to write a book on how to raise a venture fund and, you know, get access to, you know, emerging fund managers. But to kind of dive in a little bit more on kind of the LP front, you're talking about where you create, you know, where's value actually generated. I imagine you got exposure to all asset classes. What made you lean in harder on venture?

Winter: Venture felt like net new value creation, right? So I'm all for financial engineering because it's interesting, it's intellectually stimulating. But I was sitting on the private equity team as my first investment role and investing across, again, like I mentioned, buyout, growth, distressed, venture, established venture, emerging venture. And it did feel like venture capital was intriguing because you were business building, like you were creating the value and you almost had like venture, if you think about it, there's this dichotomy of business building and creating value out of nothing. And then there's like the capital markets. You're building into the capital markets from venture, but that was kind of what was intriguing to me. And I think my bias is more entrepreneurial. So for me, I was kind of drawn to that, where I was like, hey, yeah, you can do financial engineering, but what's actually contributing to solutions in the world? And aligning with those people, everyone's kind of playing in the economy, but who are the people that were, again, net new generating impactful companies?

Right, again, that would grow up into the capital markets and they would be valued at some point and the financial engineering would happen at some point. But at the beginning, it was like raw business building. And engaging with those people, like if you're living and talking and thriving alongside of those people, that's what got me excited. And I was like, how do I hang out with these people more? And how do I support them?

Jason Kirby: I think that explains why there's such a boom in interest in venture capital as a whole when it comes to people that would have gone to investment banks and or leaving investment banks where the money's at, typically finding their way into venture. But when we look at venture as the asset class in and of itself, in comparison to private equity and all the different options there are out there, how do you find performance and alpha as an LP in the venture capital game?

Winter: Yeah, great question. I think there's a way that Coolwater does it. So, I mean, I think you have to identify what alpha is and how it's generated. From my point of view, it's generated from really strong networks and decision-making processes. And so how do you identify people that have great networks, great discipline, great decision-making processes? I think that's what Coolwater is effectively. A little anecdote: I feel like I'm always trying to break things. And so I feel like my process for being an LP broke in 2016, where I couldn't meet with every single manager that I wanted to meet with because I was seeing public announcements of funds.

And I pride myself on meeting with everyone. Like I met with a thousand and ten managers last year. I want to see every single opportunity in the world. So then you can make really good investment decisions if you do that. But in 2016, I started to see the market was growing very quickly. Again, barriers to entry were coming down. The ability to start a fund was cheaper. It was easier to do that. Like you said, maybe there was this kind of cultural shift that was going on, but that was kind of a trigger in my mind where I was like the LP model is effectively broken or my model as an LP is broken. I need to see more people. So how do I, to your point, identify these alpha generators—shout out to Heather Hartnett over at Human—how do I identify these alpha generators in the ecosystem? And so I felt like there needed to be a new way. I'd almost identify Coolwater as a systems change operator, where we've kind of recreated the system of being an LP in a different way. And that's through the accelerator. Who sees the most startups in the world?

Winter: The best brands are YC, right? So you needed a change in the system of how to actually engage with managers to be able to identify them. So, okay, fine, let's rewind the clock. I'm back in 2015. Let's say I meet now with a thousand managers. I'm doing the old LP style of identifying alpha. Okay, try to find alpha for me. I need to look through your data room.

I need to read your DDQ. I need to read your PPM. I need to go through your pitch deck. I need to engage with you. I need to run a process. Fast forward a year, you've met with how many funds? Twenty-five, fifty. So you're missing like 975 managers that are in your funnel, but you actually don't have an opinion on them. So how does that make you a better decision maker? How do you actually optimize your investment decisions if you haven't changed the system?

And so that was the epiphanic moment where I was just like, it feels like I'm in the LP world, but it feels a little broken to me. Is there a way to change it? I'm not saying it needed to be fixed. I'm just saying is there another way to identify alpha in the market? And I think that's what I've tried to create over the last many years, developing this accelerator for funds.

Jason Kirby: How do you meet with a thousand people a year?

Winter: You take 20 to 40 calls a day for a few months out of the year. And then you also have a very tight filter on folks that you know just aren't relevant for what you're offering value to.

Jason Kirby: So these like 15 minute, just quick call to identify personality traits or just something about them, or are you actually reviewing the materials?

Winter: Sometimes. One of the meta concepts of venture is alignment. So what do we do at Coolwater? We offer value-added programs for emerging managers. And we just keep on iterating on those programs to try to add more and more value, to try to make them more and more valuable. We're in cohort nine right now, much tighter, much more focused than even cohort seven.

We're just never satisfied with the level of value that we're adding and just keep on recycling and reiterating into that. But yeah, I think creating the process—we definitely got some good feedback in the beginning from people that hadn't invested into similar models—just how do you create the top of funnel and the filter and the ability to know what you want?

Decision-making processes: if you have a good process, you can run it very quickly because it's tight, it's focused. You know what you like, you know what you don't like, or even if you like it, you know what's out of scope for the moment. And so, what do we do? We run effectively two core programs. We run a program for emerging managers: Are you an awesome investor and want to launch faster? And you are institutionally biased, meaning you want to create a great firm over time. Coolwater is a great place for you. And we run a core program that is largely focused on launching and fundraising and understanding the institutional LP perspective, in line with my first book, How to Raise a Venture Capital Fund. And then there's a core program around building your back office. I had the lucky experience of helping set up the operational due diligence processes and running those and really trying to understand what it means to make that jump from emerging manager to established. It's such a murky gray area. That's debated on all the panels—define emerging manager, what's an emerging manager? Well, when do you become emerged? It's the never ending debate. So the second program tries to support that jump: what is the operational due diligence process?

What do you need to set up to be buttoned up and check the boxes so that you can get the institutional check? And again, that's an iterative process. It doesn't just happen—you have to have the knowledge. You have to have the implementation. You have to build the organization around it. You have to manage that process over time. There are these pieces there. That's the second program of: hey, you want to do this, you're institutionally biased, how can Coolwater package it in a way that's digestible, where it makes sense, where it doesn't take you five or ten years to learn? So your go-to-market is that much faster. I think this process has already played out in the VC space. Fred Wilson blogging, Brad Feld writing books, people blogging for years, you selling your company, writing online, you doing podcasts. There's this massive amount of knowledge on how to build a startup company, but there isn't a massive amount of knowledge on how to build an investment firm. And that's what Coolwater stands for: if you want to build a great investment firm, what is the corpus of knowledge you need and what is the corpus of implementation and management skills you need to actually do that? That's what Coolwater offers through focus programming.

Jason Kirby: In an oversimplified way to help correlate for our audience, it's essentially like Y Combinator, but for emerging fund managers in venture—giving them the resource, the access, the network and support for fundraising and the structure and credibility that comes with it. You're not accepting everyone, just like YC. You have tons of applications, and the more applications, that’s part of your process—get as many applicants as possible so you can see and meet with as many people as possible. Is that a safe assumption?

Winter: Exactly. That's totally fair. And again, a cultural affinity as well—you have to want to build a great firm and that's who we're looking for to join Coolwater.

Jason Kirby: And for the sake of education, maybe it's an exited founder who wants to start a fund. I see that happen all the time. It's a conversation I see pop up all the time. Or the founder that is chasing venture capital to raise and doesn't understand what it's like in the VC's shoes when it comes to actually raising capital on their side. What's the difference when it comes to running a company and raising capital for your company as a direct investment opportunity versus being a fund manager and raising capital for your fund?

Winter: Another opportunity to create empathy between founders and VCs. I think the process for raising for a company still requires an immense amount of time and effort and coordination and organization and discipline to be successful. But—and this is at the risk of getting in trouble here—I think it's easier to raise for a company than it is to raise for a VC fund. If you think about raising for a company, you're selling the hope and the dream. People like you, you're talented, they give you some money to build what you're going to build. Fast forward six, twelve, eighteen months—Is it built or not?

Jason Kirby: Yeah.

Winter: Is it working or not? Has the market validated it or not? A fund doesn't really have that luxury. Have you built the fund or not? Yes, I've set up processes, but the LP is going to ask: what's performance? We wrote checks into 10 companies—what are those 10 companies doing? Well, they're building. So what's the performance? Well, we took fees, so early on you're down on paper. Is an investor going to write more? If you're a startup and you're like, hey, I lost some of your money and I'm no further along in terms of performance and it's not clear if my product has been validated and the product isn't further along because I've just been fundraising instead of building product, and I'm a year and a half later—is a seed investor going to come in? They'll ask: what did you do with friends & family money? With a startup, you can point to KPIs and growth. With a fund, you make it tangible by what you're building as a business—your processes, your intention of building the organization, the policies and procedures, the infrastructure, reporting. Before you actually have performance, your go-to-market has to be much stronger. You still need to be excellent at sales in both, but it's probably more difficult for a fund.

It's also harder to blow up a category as a fund manager without domain depth. In startups, the outsider perspective can work; in fund management, saying “trust me with $20M in insurance, even though I’ve never done insurance” is a tough sell. There are nuances you have to internalize to be successful as a fund manager.

Jason Kirby: I'm glad you chose the controversial opinion that fundraising for a startup is easier than a fund because I personally agree. When it comes to emerging managers and that example you gave with the insurance person with no experience trying to raise money, what are you seeing in the market today that is actually getting funded from a fund perspective? So, emerging fund manager going out—what are you seeing that allows them to close fund one or fund two?

Winter: Great question. I'll break it into three buckets. First, the authenticity story: a narrative that sells well. Example: a former insurance executive who founded and sold fintech/insurtech startups launching an insurance-focused fund—everything lines up. LPs have always looked for that story. The fundraising market is more challenged in 2024 than 2021, but that archetype still gets funded.

Second, people who are persistent and incredible at fundraising—capital network, sales and marketing skills—are still getting funds off the ground. In this market, you need to be more disciplined and better at fundraising because it's harder: you'll work three times as hard to raise half as much.

Third, themes that match the zeitgeist: Nvidia/AI disruption, climate and sustainability. Top-down shifts are creating gaps to address. Sometimes teams in those areas may be less authentic but still get funded due to the theme—ideally you have authenticity, strong sales, and a world-positive theme together. Another trend we've seen through recent accelerators is operator-turned-VC—more of that behavior today than in 2021 when cost of capital was lower. With higher cost of capital, some dabblers exit; those with founder grit persist. Today’s fund starters look more like 10–15 years ago, not 2021.

Jason Kirby: And do you think those operator-turned fund managers have a higher probability of success or a higher probability of getting funded?

Winter: If it's an authentic story, yes for getting funded. For success, it depends, but the market has shifted to transparency and value-add. Founders want perspective on product, strategy, business-building. Former founders may have more empathy and functional expertise, and can be more helpful to early-stage companies—potentially changing outcomes. Founders are more savvy about constructing a syndicate and look for additive investors. Authentic operating background resonates more today than 20 years ago.

Jason Kirby: From a founder perspective, especially second-time founders, capital becomes a commodity. Differentiators beyond capital—like hands-on help—matter. Operators can earn earlier access and better terms, and build long-term relationships, which is appealing versus purely financial backgrounds. I agree.

Winter: Definitionally, this is why many operators-turned-VCs focus on early stage, and many with more traditional finance backgrounds gravitate to growth-stage firms, where investing is more financial. Early stage is about navigating ambiguity—no obvious right answers—so experience in the gray matters.

Jason Kirby: Going back to supporting the ecosystem and emerging fund managers, when these fund managers come to you—whether it's raising capital or their overall structure—what are some common mistakes GPs make in the early days of setting up a fund?

Winter: A big one is not being self-reflective enough. On authenticity: have you asked how others will perceive your story? On readiness: are you at the right stage to manage other people’s money? Maybe the answer is no, and more reps are needed—let your angel portfolio mature, stay longer at a VC to build attribution, or take another swing as a founder to increase your GP commit and tighten your go-to-market. That takes self-awareness.

Another is not trialing your narrative with trusted advisors. Sit down with people who can offer multiple perspectives and examples, not just a single “my way or the highway” answer. The iterative process helps avoid being the person who starts a call with a 20-minute monologue. Slow down and think: what is the product I’m creating at my venture firm—both at zero (selling the dream) and over time? Strengthen that fund product continuously.

Jason Kirby: I went through that self-reflection myself after exiting my last company. I loved the idea of running a fund, but asked: do I really know portfolio construction, delivering returns, managing others’ money over time? The answer was no, so I sought more reps and exposure first. I'm glad I did—starting a fund going into 2022 would have been a nightmare. I hope everyone has someone in their corner to ask that question. You mentioned a cohort model—how does it work for a potential fund manager who thinks they're ready to apply?

Winter: We have programs built around core concepts emerging managers need to understand and key problems to solve. It’s grown into a long list of topics to learn, build, implement, and manage. For the core program for fund managers, why a cohort model? Venture succeeds because of information sharing and strong networks—the speed and breadth of information, and the nodes you know to get things done. The cohort model enables network effects and lets us deliver more impact faster.

But you must manage those network effects. If you just put people in a room and expect someone to drive, it likely won’t happen. We curate 20 of the most select next-generation managers—immensely ambitious and already successful—and then we manage that group and layer in a constantly iterating program. That compounding effect of community + curriculum is powerful. Fundraising conditions change every six months; we bring in 50+ teachers across LP archetypes for perspective, and GPs from diverse geographies share insights. We’ve helped launch 200+ funds and 350+ GPs; the knowledge base is huge, and we translate it so it’s digestible and actionable.

Jason Kirby: Sounds incredible for anyone launching a fund. Do you typically see only first-time managers, or also fund two, or spin-outs starting a new firm?

Winter: If you’re not ready to be a fund manager, we have a program focused on doing deals and building track record (you need to be accredited). In the core program, we’ve had funds one through four. If you’re fund three or four, you’re often joining for the community access. If you’re fund one or two, you’re focused on best practices and ensuring you’re doing everything to build the right product from the start and increase your fundraising odds.

Jason Kirby: As we conclude, what’s the best way for someone to learn more about Coolwater or about you?

Winter: Reach out on LinkedIn. Say you heard me on Jason’s podcast. If you’re a fit for the show, Jason can assess that, and I’ll also share information on Coolwater—what we offer based on where you are in the journey: aspiring angel building track record, ready to launch, or launched and seeking to build out your back office. Give me some context and I’ll point you to the right path.

Jason Kirby: I’ll leave links in the description to your website and LinkedIn. Winter, it’s been a pleasure getting a different conversation than usual—empathy for both sides of the equation: founders raising capital and fund managers raising capital. Thanks for sharing with our audience.

Winter: Jason, thanks for having me on. This was fun.