Episode #1: High Heels on the Job Site

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  Narrator:
  In a world captivated by criticism and negative clickbait headlines, it’s easy to overlook the scope and power of technologies propelling us forward. At Tech Optimist, we delve into the vibrant intersection of technology and entrepreneurship, shining a light on innovators who are building a better future. As members of the most active venture capital firm in the United States, our unique vantage point offers us insights into the real-world impact of technology. Join us as we explore, celebrate, and contribute to the stories of those creating tomorrow.

  Mike Collins:
  Welcome to the first episode of the Tech Optimist Podcast. I’m Mike Collins, the founder and CEO of Alumni Ventures. The Tech Optimist Podcast covers topics at the intersection of technology, entrepreneurship, and venture capital.

  In this first episode, we have three blocks for you. In block one, I interviewed one of our founders, Janna Wanzdilak. I’ll tell you a little bit more about our company Bundle in just a moment. In block two, I talk to one of our young principals, Naren Ramaswamy, on three things that VCs and entrepreneurs are talking about. Finally, in block three, I get an update from Laura Rippy, a leading VC who talks about the status of women in the venture ecosystem. Enjoy the show.

  As a reminder, the Tech Optimist Podcast is for informational purposes only. It is not personalized financial advice and it is not an offer to buy or sell securities. For important additional disclosures, please see the text description accompanying this episode.

  In this block, I chat with the CEO of AV portfolio company, Bundle, Janna Wanzdilak. For this startup, which she founded with a Stanford Business School classmate, she’s working to bring tech-powered buying solutions to small builders. She’s still at the seed stage, but the Bundle team has made some real progress. Hi, Janna. Where does this find you today?

  Janna Wanzdilak:
  Yeah, I’m calling in from Oakland, California, actually about to go interview someone down the street and then heading to San Francisco for a meeting this afternoon. So hopping around, but the Bay Area.

  Mike Collins:
  Great, excellent. And tell our listeners about Bundle. What’s your genesis story? What do you guys do?

  Janna Wanzdilak:
  Yeah, totally. So Bundle is an end-to-end procurement platform—or a digital procurement platform—that makes it easier to buy, sell, or manage construction materials. We’re really focused on the SMB residential space, and we’ve seen that when builders are using Bundle, they’re able to run their purchasing process at 10x speed and also find between 10 to 20% cost savings on products.

  So, super cool—really addressing the problem that almost every construction project, 98% of construction projects, finishes over time and over budget. That results in almost $400 billion in spending annually in the US as a result of procurement issues.

  So myself and most of our team have come from the construction industry, really seeing the challenge in real time—how old-school and antiquated a lot of processes are in designing construction. I think for me personally, before coming out to the West Coast for business school, I had very much been feet on the ground in design and construction. I had project-managed the headquarters of the company I was at and had really built a cool project at the end of the day, but it finished way over time, way over budget, and opened my eyes to how antiquated and fragmented so much of design and construction really is—and how much we really need to step upstream and rethink how some of the processes happen to unlock better building downstream.

  Mike Collins:
  So just to play it back for my own brain: This is a small builder that’s building, what, dozens of homes a year, and they’re keeping track of all the stuff that goes into building a house—what, on spreadsheets and file folders? Do they typically have a person that does this or are they doing it themselves?

  Janna Wanzdilak:
  Yeah, great question. And exactly right—a lot of this is pen, paper, spreadsheets, phone calls, emails, sometimes faxes, the dreaded fax machine. They often will have someone managing the process. For a small builder, they’re often pulling someone off of a job site, which can be a challenge. That person has something else that they could be doing.

  I would say if you’re looking upstream at a bigger builder, they have the money to throw at a purchasing team who are negotiating relationships further up the supply chain. They have volume, so they can negotiate some of those relationships. That’s exactly right. As a smaller builder, you don’t necessarily have that money to throw at the problem. And a lot of your projects are different from one to the next, so you’re needing to call tens to hundreds of suppliers on every project, figure out pricing, basically run a bid process, then handle payments with all those guys, and then figure out where all your products are on their way to the job site.

  So Bundle allows you to do all of that in one platform. I would say the other value that we bring—hence our name, Bundle—is that we’re essentially aggregating small and medium builders or small and medium projects together and giving that access further out the supply chain. It’s almost like a buying group in that we’re hopefully getting them better pricing, lead times, availability, maybe even just better return policies or more direct communication to a manufacturer or wholesaler than they’ve had otherwise.

  Mike Collins:
  Cool. So tell us a little bit about the company. Where are you on your journey? Do you have a co-founder? How’d you guys meet?

  Janna Wanzdilak:
  Yeah, definitely. So I met my co-founder, Edison, at business school. He had been an architect for about five years before coming to business school, so he’d seen very similar challenges in the industry but from a different angle.

  We’ve been around now for about two and a half years, which is wild—time flies. But we raised about a $1 million pre-seed at the end of 2021 and closed about a $4 million seed round last February, so about a year ago.

  We’re now a team of 11 with some contractors beyond that, churning away at a solid early product and customer base. 2024 is hopefully a big year of growth for us—we’re really focused on solving some of the go-to-market questions. We’ve obviously sold to a bunch of customers so far. The question is where’s the unlock there, whether it’s a market angle or just figuring out how to have a rinse-and-repeat process to really drive fast advancement there.

  Mike Collins:
  Tell me a little bit about when you bring technology to an industry or a customer base that hasn’t had a lot of it yet. Even if it’s clearly a better way to do it, you run into just change—people are busy, and this is the way we’ve always done it. How have you guys thought about addressing that kind of roadblock that all businesses like yours face in their journey?

  Janna Wanzdilak:
  Yeah, definitely. I would say two different things. One is I really think having a team that comes from the industry goes a long way—people that can talk and see around corners, people who have experienced the exact pain points that our customers have. That really helps in those early sales conversations.

  But even beyond that, I would say the other big thing is it’s an interesting time in construction tech right now because we are often convincing people to go from spreadsheets, no software, into software. But a lot of the builders we talk to have actually tried out some sort of software at this point, and many of them have been burned.

  So I would argue it’s almost more complicated than just getting them to try it because there’s often been software that was either over-promised to them or took so much time to onboard. Again, they’re small teams. If they’ve spent a ton of time getting everyone up to speed for a solution that doesn’t really help, they’re much more cautious about doing that again.

  One of the things that I think differentiates us in the industry is that we’ve built a tool that has almost zero onboarding. We honestly go from a demo call to “send us a list of products,” and you’re onboarded. It’s a really simple and streamlined process to get things moving.

  Part of that is we’re trying to take the workflow from you. So we aren’t a product that we’re expecting you to sit in every day. It’s a little bit more like you wake up in the morning, go to work, log into Bundle, do your couple of tasks, and then you’re out—hopefully in 10 to 20 minutes max. With that, we really focus on shaping an experience that’s lightweight for the builder to address challenges like that.

  Mike Collins:
  How has it been as a woman in what I’m guessing was a very male-dominated construction business? Is it, “Oh, they remember me because I’m a woman,” or does it make it more challenging? What’s been your experience in your real life?

  Janna Wanzdilak:
  Yeah, it’s a great question. I think it very much depends on who we’re selling to. The industry is definitely changing, for sure. I think being memorable is great. I actually wrote a blog at some point that was basically like, “I’m memorable because I walked across a job site in high heels,” and that’s not typical.

  I mean, I’ve definitely picked a sales team that looks a little bit more like the industry when we’re selling to some of those customers, and sort of dropping by a job site definitely goes a long way. I think when you can establish credibility, some of that is looking the part.

  But we actually work with a lot of different—what I would say are newer, kind of new-generation building designers. And so, it’s actually been nice to have a pretty diverse team to cater to a lot of different customer types as well.

  And it’s an interesting time in the industry, which has created this boom in construction tech in that a lot of people are retiring out of the industry that fit more of that old-school profile, and not enough new people are coming in.

  So the people that are in family businesses or are a little bit younger in the industry are really looking for solutions to bring their businesses forward. But there’s also not enough labor. It’s an interesting time to be in innovative tech. We have a solution for you—we market ourselves as your outsourced purchasing team. And with that, people are sometimes looking for something new or different from an industry-as-usual workflow. So our business has a huge role.

  Mike Collins:
  Take a step back. I mean, you’re a strategic thinker. What do you see as kind of construction tech? What are some of the big trends that are tied to macro things hitting the industry right now?

  Janna Wanzdilak:
  Yeah, definitely. I think digitization over the last 5 to 10 years—what you find on a job site—is huge, just something that has really unlocked a lot. For us directly, COVID was massive also. I think builders were already thinking about moving to software and the digital world, or at least a lot of them were, but the supply side was still pretty resistant.

  Mike Collins:
  Yeah, the supply chain got so screwed up. They were almost forced to change.

  Janna Wanzdilak:
  Exactly—and to sell a product, you had to not just be brick and mortar, so there was a big push there. But that’s a couple of years ago.

  I would say I’ve seen some interesting things in AI generally. I think a lot of the AI in the industry, in my opinion, is searching for a problem. We’re trying to leverage it as much as possible internally to make things smarter, better, faster, easier for our builders. But we’re already solving a big problem with a little bit more of an old-school tech approach.

  The other really big trend and tailwind is labor generally. Like I mentioned, a lot of people are leaving the industry and not enough are coming in. While we do directly impact that, we aren’t solving labor first and foremost, but we do kind of take the place of a purchasing team in some regards.

  You still need someone to operate the software, so if you have a stretched-thin person, we’re really empowering them to do their job better, faster, more easily, and run into fewer issues.

  Actually, an interesting customer story—one of our oldest customers, who’s been with us for about two years now, was piloting with us and lost their procurement person. They were like, “Do we even need to hire someone? Let’s just use a Bundle.” And that’s what they’ve been doing for two years now.

  They have their designers and construction team plug into the software where they need to, whether that’s from a job site or to actually order something, but they don’t actually have that in-house purchasing team anymore.

  We just finished our 2023 year in review with them and showed that we’re saving them the equivalent of one and a half full-time employees in procurement every year—which, for a small business, is huge. Not to mention the cost savings with products and getting them that bulk buying power, at least in some cases. So definitely interesting on the labor front, and I think we’ll continue seeing similar stories like that.

  Mike Collins:
  What are you most excited about for Bundle in 2024?

  Janna Wanzdilak:
  Yeah, I’m excited that we have a really strong product, a really strong team. I think we’ve proven out—with a couple of million in GMV last year and doubling GMV in revenue—that we have a roadmap for how we can keep growing this year.

  We just grew the sales team. Another salesperson started yesterday, so we’re kind of putting more fuel on the fire and really seeing what we can do with this, how many customers we can help solve these problems for.

  One of the big pushes for us over the last year has been growing our supply side of the business. Last year, we went from about 8,000 products in our system to 50,000, and that continues to grow every day.

  So we’re really starting to see more of the connections happen across what we think of as a managed marketplace, powered by the managed marketplace we’ve built on top of that with workflow tools on either side.

  What’s interesting about our business is that—well, I joke that my next company is just going to be a software company—because we’ve basically built a software product for our builders and a totally separate product for suppliers. It only works if everything is working well across the middle to create the marketplace dynamic.

  But we’re starting to see enough of those relationships and a solid enough product to really start seeing that marketplace hopefully take off a little bit.

  Mike Collins:
  Yeah, I mean, those two-sided marketplaces are hard and they take a long time. But if you can do it, it becomes really powerful and a huge moat, and then you start getting into really powerful flywheels.

  Janna Wanzdilak:
  Totally.

  Mike Collins:
  Just stuff that’s good is really hard and it takes a long time, for sure. Give me an ask for our audience—how can our investors, people who’ve invested in your company, or people who are just fans of cool companies and entrepreneurs help you? What’s your ask for our audience?

  Janna Wanzdilak:
  Yeah, so one of my favorite parts of the industry is that almost everyone I talk to is either directly related to construction or has a brother, cousin, or friend of a friend who is in construction and can relate to some of the problems that we’re solving.

  So my ask is I would love to talk to any and all of those people, both from a learning perspective and because I think go-to-market in an industry like this is the hardest piece. There’s a lot of direct selling, a lot of network effects, referrals, and things like that.

  So I would love to talk to those people. Feel free to email me.

  Mike Collins:
  Yeah, Janna—[email protected].

  Janna Wanzdilak:
  Yep.

  Mike Collins:
  Excellent. Okay, any questions for me, Janna?

  Janna Wanzdilak:
  How are you doing today?

  Mike Collins:
  I’m doing great, actually. Spring is in the air here in New Hampshire, the days are longer, and it’s super busy. The venture industry had a bit of a backlog of deals with companies putting off getting funded, and now it seems like everybody’s closing rounds. So, super busy—but that’s always fun.

  Well, thanks for your time today and giving us an update on Bundle, and we’ll talk again soon. Take care.

  Janna Wanzdilak:
  Awesome. Sounds great.

  Mike Collins:
  Have a good one.

  Janna Wanzdilak:
  Bye.

  Mike Collins:
  Just a brief interruption to tell you a bit about Alumni Ventures and our Doctors Innovate Fund. Alumni Ventures enables individuals to invest in startups shaping the future. We build diversified portfolios by co-investing alongside renowned lead investors.

  Today, we serve over 10,000 investors who have invested more than $1.3 billion. With our Doctors Innovate Fund, you can invest in a portfolio of around 20 healthcare technology companies. From transformative healthcare services to groundbreaking diagnostics, our founders are paving the way for a healthier future.

  If you’re curious about diversifying your portfolio and helping to drive the next wave of medical breakthroughs, visit us at av.vc.

  Thanks, Janna. Sometimes the best businesses are hard and grindy and take a long time, but bringing technology to a sector that has been slow to adopt can be hugely rewarding and valuable if you can crack the code. Bundle is off to a promising start, and we wish them continued success.

  Our community often asks me, “What are you seeing, hearing, thinking about?” I thought others in the audience might find this interesting as well. In this segment, I picked three things that I recently talked about with fellow entrepreneurs, VCs, or others in the ecosystem. This segment is an experiment—let me know what you think. Hi, Naren. Why don’t you introduce yourself?

  Naren Ramaswamy:
  Hey there. My name is Naren. I work as a principal on the Spike Ventures Fund for Alumni Ventures, and I cover enterprise AI and deep tech. Mike, I’m excited today to talk about what’s on the mind of VCs. So why don’t you tell us: What are three things on your mind with regard to the market right now?

  Mike Collins:
  I think the Oprah special about GLP-1 drugs is getting a lot of buzz. Everybody talks about AI—appropriately—as a huge transformational technology. But I think there’s a lot of folks who think about this class of drugs, given that such a huge percentage of the population struggles with obesity and a lot of our economy is driven by cheap food and dealing with exercise, weight loss, body image, and all of that… It’s happened before that Oprah has created a waypoint in societal conversations—mental health, equal pay, literacy.

  Her superpower is she moves the conversation. She has been very open about her own struggles managing her weight, and America has followed that journey alongside her for 40 years. When she comes on and says this is a big deal, that we now understand more that this is a chronic disease, and that there’s now the beginning of a class of drugs fundamentally empowering many patients to address their disease in a way that has never been done before—where you can really decide what your ideal weight is and get there without people testing your character, willpower, or anything that doesn’t do justice to the fact that this is a chronic disease—well, I think it’s a seminal moment in our discussion of obesity as a society.

  And then, as a venture capital person, everything’s a nail—so venture people are thinking about: What is the investing opportunity? What is the investing horizon if we have this drug out there? I mean, our job is to think three years ahead.

  Clearly there are issues about availability, cost, and insurance companies not covering this drug. I guess they’d rather someone have a heart attack or be treated with diabetes for 15 years. But money will talk, and that will get addressed. If you look at the pipeline of other drugs—drugs in pill form, drugs addressing other receptors—it is a very robust pipeline.

  So again, I think the way the world’s going to be five years from now based on this technology is transformative. The Oprah moment for GLP-1 drugs would be number one on what people are talking about this week.

  I think if there was a second point, Naren, I would say what’s going on with Apple and AI is also getting a lot of buzz. There’s a long-anticipated lawsuit by the Justice Department hitting. I think that is within the climate of a very different regulatory environment where big tech is really in the crosshairs and a lot of M&A is being chilled by a much more aggressive regulatory environment.

  I also think there is a lot of buzz about Apple’s strategy when it comes to AI and rumored talks with Microsoft and Google. Again, smart company—they know they have to play. They lean into privacy, chips on your phone, AI on your phone. I think that is clearly something a lot of people are thinking about and talking about: What’s Apple’s play in the AI world going to be?

  And number three: I hear a lot of people talking about Lex’s interview with Sam Altman. Lex is a great interviewer, and Sam is one of the great innovative minds of our generation.

  Clearly there are lots of good nuggets, perspectives, tidbits on AI—where ChatGPT is going, what ChatGPT-5 might look like, AGI, how to define it, where it’s going. But for me, the very human part of that conversation stood out: Sam talks very personally about the weekend when he was fired, the emotional roller coaster, the fact that to this day it has impacted trust and the way he thinks about his board and governance.

  As an entrepreneur, I was struck by the fact that he was fired at 10 AM and by 6 PM he was already thinking about his next startup. There was so much of the personal side of Sam’s conversation with Lex about that weekend that a lot of entrepreneurs and board members can relate to and learn from.

  So for me, those are the three things I’m hearing, talking about, and personally thinking about this week.

  Naren Ramaswamy:
  That’s great. Thanks for sharing. I’d love to double-click on those. Starting with GLP-1’s Oprah moment, where do you think the ripple effects are for VC investors to really see where the puck is going and invest accordingly?

  Mike Collins:
  Yeah, I mean, I think there’s two parts to that. First, you have to have a prepared mind. If you envision that can be the future, then when you’re getting pitched by entrepreneurs, you’re prepared to fold that into the reality of the future they’re building their company in— the same way you think about the world through the AI lens.

  Part of being a VC is you don’t have to come up with all the ideas or areas, but you need to hear when someone has nailed it and be prepared to back their journey.

  I think there’s a lot more thought that we all need to give to—and this is trite and flippant—but what does a “skinny America” look like? Because we have an obese America today. From how people eat, how they exercise, how they interact with each other…

  Very smart hedge fund guys with public equities have had the Ozempic trade kind of paired in place for a while now, which is to simplify: I’m short McDonald’s and I’m long Lululemon. Because when somebody goes from being 100 pounds overweight to what they were when they were 30, that changes buying behavior, eating habits, exercise. You need fewer hip replacements, you want to travel more—there are all kinds of very interesting, thoughtful, deep ideas out there.

  So I think there are flavors of the Ozempic trade that VCs need to think about and invest behind.

  One of the things that was even in the Oprah special, Naren, was a brief but powerful interaction with the CEO of WeightWatchers. I think a company like WeightWatchers—or new companies in that space—need to think not just about providing the framework and tools to help you lose weight, but about becoming your partner to deal with all the other things that go into you being 100 pounds lighter.

  That includes the psychological part, exercise, healthy living, relationships—there’s a lot that goes into how people look and their energy levels. So I think that’s an example of just one slice: there’s a whole new generation of people that will help partner with people through this journey, beyond just the drug making it an order of magnitude easier to lose weight and keep it off.

  Naren Ramaswamy:
  Absolutely. And you alluded to this, but Morgan Stanley reports that up to 25% of Americans have expressed interest in GLP-1 drugs, and right now it seems like it’s only 1 or 2% of the population actually using them. So we are on the cusp of a large consumer trend here.

  Mike Collins:
  Yeah, I was joking with somebody in Hollywood actually yesterday. If you look at the early adopters of these GLP-1 drugs, it’s disproportionately Hollywood and the Upper West Side of Manhattan. And those people are losing that excess 20 pounds. They’re not the people who truly need it most.

  There’s a big class of people who need this but can’t access it—it’s too expensive, they’re not confident, or their doctor isn’t educated enough. We haven’t hit the big part of that curve yet. There’s much more ahead for sure—we’re in the first inning.

  Naren Ramaswamy:
  Absolutely. Switching topics to AI: You’ve previously talked about “AI in your pocket” as an investment thesis—that AI will become more and more ubiquitous. Apple seems well-positioned with their tech prowess and distribution. If 40% of Americans own an iPhone, how do you see this playing out over the next five years?

  Mike Collins:
  Yeah, I don’t think there’s one-size-fits-all. I think there will be corporate solutions, public solutions, open-source solutions.

  This is again where I think the buzz is. Apple, because of the intimate relationship they have with you and your phone, strategically and philosophically leans into privacy. With the biometric security already in Apple phones, I have no inside information, but I think it’s a natural marriage. They’re collecting information from my watch about my walking—it’s a very intimate piece of technology for all of us.

  I think there are a lot of issues people have with AI and sharing personal stuff. Just take health information, for example: Do I want that up in the cloud? On some website? Or do I want that in a very private, locked-down, secure place where my personal AI gets to know me and my habits in a way I feel is safe and secure while giving me advice?

  I think AI in your pocket—very personal, growing with you over years—is natural. I think Apple will either make or buy and become a player in the space. It’s inevitable. How and why? The execution? I trust they’ll figure it out, but it’s a very interesting space.

   

  Naren Ramaswamy:
  And that’s a good segue into Sam Altman talking about this in his interview with Lex about the ubiquity of AI. He alluded to the fact that OpenAI will be releasing another new model this year, and that GPT-5 is going to be miles ahead of GPT-4 with infinite context length and models like Sora, which help convert text to video. So definitely a lot of activity there. How do you see AI playing into the physical world?

  Mike Collins:
  Yeah, I think one of the takeaways from Sam, who’s dealing with things that are probably two years away from us seeing—what he’s working on, seeing, and knowing is reality—is that he looks at what ChatGPT Turbo or whatever the latest release is and thinks it’s awful. And all of us dealing with the public versions of this say, “Hey, this is powerful already.”

  Listening to him, you really get a sense of the slope we’re still on—we’re still in the deep part of this slope. It was very exciting hearing him talk about where he sees the crossover between robotics and AI as just a natural marriage. We’re going to bring all of these great innovations in robotics right now together with all the great innovations in AI.

  I think it’s inevitable. That combination is going to be a very powerful enabling technology that will again take the most dangerous, repetitive, and mundane jobs in our society and replace them. I think that’s a good thing.

  If you just take the most dangerous jobs, those are going to be attacked first. I was looking at a startup doing work in fruit picking, which requires very fine motor skills but is also repetitive, tough work. You need a physical tool to actually grab the plum or apple and pull it from the tree, but you also need to pick the right one, at the right time, in the right way. Those are all machine learning and AI systems.

  I think it’s so exciting—it’s a golden age to be at these companies or to be investing behind these kinds of management teams.

  So yeah, the trajectories of both robotics and AI are clear. And just a little inside baseball—we have an AI Fund that’s now on its fourth vintage here at AV. I think for our next fund, probably in spring 2025, it’s going to be AI and robotics. We’ll likely merge those investing areas as a statement that there’s groundbreaking work in both. They’re different but related enough that I think investors will want a portfolio covering both.

  Naren Ramaswamy:
  Absolutely, and I definitely agree—it’s a very exciting time to be an investor. Thanks for your thoughts.

  Mike Collins:
  Yeah. And we’ll talk again in a couple of weeks. Thanks, Naren.

  Sophia Zhao:
  Hi, everyone. I’d like to take a quick break and tell you a bit about Alumni Ventures and our AI Fund. Alumni Ventures offers smart, simple, and accessible venture portfolios for individual investors. We build diversified portfolios with low minimums, co-investing alongside established lead investors.

  It’s a strategy that has mobilized over $1.3 billion from a community of more than 10,000 investors. With our AI Fund, you’ll have the opportunity to invest in startups focused on AI, including areas such as machine learning, natural language models, speech recognition, machine vision, and more.

  AI has the potential to revolutionize multi-billion-dollar sectors such as healthcare, education, and transportation by improving efficiency, accuracy, and productivity—while also potentially solving complex global challenges like climate change and disease outbreaks.

  So if you’re interested in a portfolio of companies focused on revolutionary AI investments, visit us at av.vc.

  Mike Collins:
  Thanks, Naren. A powerful thing within the venture capital ecosystem is cross-generational learning and collaboration. I just hit 60, but I really love spending time and learning from the next generation. It energizes me, and I look forward to many more conversations with young people in the business.

  In this block, I chat with Naren Ramaswamy, one of our managing partners, about the state of play of women in the venture ecosystem. Bringing together women VCs, founders, and capital has never been done at the scale that Laura and her team plan to do it.

  Laura, welcome to the Tech Optimist Podcast. Let’s just kick things off. Tell the audience a little bit about yourself and your role at Alumni Ventures. What do you do day to day?

  Laura Rippy:
  Yeah, thanks, Mike, for having me on board. So I wear a few hats here. Today we’re talking about the Women’s Fund, and I am so excited to share more about it. But my other hats at Alumni Ventures—I run two of our flagship funds: the Green D Fund for Dartmouth alums and the Yard Ventures for Harvard alums.

  I’m also on the board here and just a long-time fan of what we’re building at Alumni Ventures, so I couldn’t be happier to be joining you today.

  Mike Collins:
  Excellent. So yeah, today we’re talking a little bit about women in the venture ecosystem. What’s the state of play? I mean, there are women founders, women investors, women VCs. Where are we in spring of 2024?

  Laura Rippy:
  Yeah, there is a funding gap, and that to me means an opportunity. At this point, about 25% of venture-backed startups are led or co-led by women, but they only get about 15% of capital. So what’s the flip of that? That means 75% of all startups have only male founders, and 85% of venture dollars go to all-male leadership teams.

  I think that’s an opportunity because if you actually unpack the female leadership of those startups, you learn that female-led startups tend to be more capital efficient and they exit sooner. Combine that with the fact that most partners in venture firms—call it 90%—are male, and you realize that we’ve discovered an opportunity here that should really be addressed by the investors coming into Alumni Ventures and the Women’s Fund.

  Mike Collins:
  Yeah, it seems that we’ve made somewhat more progress with the number of women entrepreneurs. Again, I’m an old-timer, and if you look at startups at the pre-seed and seed rounds, that ratio is improving and much more diverse along many dimensions than it was 15 years ago.

  Laura Rippy:
  Correct.

  Mike Collins:
  But it seems there’s still a much bigger lag in other parts of the ecosystem—people like yourself who are investing professionals, VCs. As you point out, there’s still a funding gap and, frankly, a business opportunity.

  I think the other thing is really the capital side of this equation. We’re all familiar with women controlling more and more capital in our society, and there’s a huge generational wave coming—that’s mind-boggling in scale, tens of trillions of dollars—that will be passed on from baby boomers to the next generation. That wealth transfer is going to be gender-even, frankly.

  Laura Rippy:
  That’s right.

  Mike Collins:
  So for me, there’s entrepreneurship and women starting businesses, women controlling capital to invest in those businesses…

  Laura Rippy:
  Correct.

  Mike Collins:
  And women partners at venture firms and LPs, and just women writing checks. I think we’re making progress, but it’s uneven and there’s still a huge gap.

  Laura Rippy:
  Well, I see that in my own career, candidly, Mike. When you’re harkening back to times where there were fewer female founders, I can share a personal story. I’m in the process of moving, and I found this publication from an investment bank where I was one of the presenters when I was a CEO.

  This publication had all 75 of the teams that were presenting at this conference. To date myself, it was back before Salesforce was public—Marc Benioff was one of the presenters, and I was a presenter as a CEO.

  In this document, they had not just the CEO, but the top five executives of each company. I went through this book page by page—75 companies—and my name was the only female name on the mastheads.

  Mike Collins:
  Yeah, crazy.

  Laura Rippy:
  Not just the only CEO, but the only executive. So I do think we’ve moved forward, and I think you’re right—we’re improving on many fronts, starting at seed and moving along.

  I also think your point about this particular moment and the way Alumni Ventures comes into the opportunity hits those elements. We’re investing in female founders, we are an all-female team of VCs choosing those investments. But more than that, because it’s Alumni Ventures, we empower individual accredited investors who want to address that funding gap to put their capital to work in these high-quality deals that we fund.

  So we stir the pot—we bring it together. It’s women and allies who have been very successful in their careers. They know that the female leaders they’ve met and want to support are fiery, capital-efficient, and ambitious. They want to put their capital to work in those businesses, and we enable that with the Alumni Ventures Women’s Fund by investing in those amazing female founders and giving investors an opportunity to participate.

  Mike Collins:
  I think it’s incredibly exciting. I think it’s the only situation I’m aware of in the whole venture ecosystem where we’re talking about women capital, women VCs deploying it, and women founders. Some people have a slice of that, but I think this is the most vertically integrated community capital source.

  So the AV Women’s Fund is really going to break ground, and I think there are tremendous flywheels in that kind of vertical integration.

  Do you want to talk a little about how our community gets involved with all of our funds in sourcing and helping portfolio companies?

  Laura Rippy:
  Yeah, absolutely. The Women’s Fund has a suite of scouts helping us surface more opportunities. I’m really flattered—many of those scouts are our portfolio company CEOs.

  The Women’s Fund at Alumni Ventures starts from a position of strength: we have 357 companies that are either founded, co-founded, or led by women that are already in the portfolio. These companies went through our rigorous process, all of the diligence, all of the scrutiny we do.

  We weren’t even really looking at whether the CEO was a woman or it was co-founded by women. They came into our portfolio because they were really high-quality deals. Now, some of those women have stepped up to be venture scouts for us. That, to me, is incredibly special—that they care about this mission.

  Laura Rippy:
  They’ve seen what Alumni Ventures does as an investor, and they want to encourage other female CEOs to work with us so that we can invest and put our capital to work on their cap tables. So that’s one piece of it.

  I think the other part is the community. For instance, yesterday I was speaking to an investor who’s coming into the Women’s Fund. She has been a CFO—I think she said around 20 times—for PE-backed companies. She comes in during turnaround situations. This woman is a powerhouse.

  She said, “I know how women lead, and I know that I can help some of these women with my capital. But give me a call, Laura. If any of them are raising money, let me know. Maybe I can help them with their pitch deck. Maybe I can help them open a door or give them some counsel and advice.”

  So that virtuous cycle I was talking about—investors fueling the Alumni Ventures Women’s Fund with their capital, helping us invest in these amazing founders, leveraging venture scouts who are opening doors, and of course, the team you mentioned (myself, Mira, Sophia, Brittany)—we are excited to compose this portfolio and to be those female investors that founders can turn to as the portfolio comes together.

  Mike Collins:
  Yeah, you touch on the fact that Alumni Ventures has backed 350+ companies with women in leadership positions. The fact is we invested in those companies because we thought they were great investment opportunities, led by top-tier VC firms, which happened to have women founders.

  That’s a position of strength from which to launch this community and fund. It’s really powerful. Are there—though we love all our portfolio companies equally—just a few sample companies that you can share with listeners to give them a sense of the types of companies we invest in, who the lead investors are, and the problems these founders are solving?

  Laura Rippy:
  Yeah, happy to share some stories because they’re so dear to my heart. I hope you’ve got a few hours for me to tell them all!

  One that comes to mind is Carry1st. This is a gaming and payments platform in Africa. In the round we joined, Andreessen Horowitz (a16z) doubled their pro rata. We followed the leading gaming VC into that round. How did we get access to it? Female founder—and specifically because we’re Alumni Ventures, we followed the alumni thread. In this case, it was a Dartmouth female founder, and that was our entry point into the deal.

  Another example is Kindbody, a fertility platform led by the indomitable Gina Bartasi. When we invested back in 2018 during the Series A, the lead VC from RRE was a woman, my team was all female, and Gina’s team was all women. Fast forward to today: the company’s valuation in its most recent round, led by JP Morgan Health, is $1.8 billion. That early belief in the company is a piece of what we do.

  Mike Collins:
  Yeah, the analogy is that this is where we created Alumni Ventures—around community and the idea that we could do better together than any of us could individually. In our society, there’s affinity—we connect with people, and that creates powerful connections, flywheels, and value-add.

  Laura Rippy:
  It gets us into places. Another example is a cybersecurity company called [inaudible]. That round was led by Accel, and we were the only other institutional investor in the round. The only reason we got in is because the female CEO went to Tuck, Dartmouth’s business school. That was our entrée.

  It’s also important for listeners to note that the categories we invest in span the full venture spectrum: cybersecurity, machine learning, robotics—you name it. It’s exemplary to see female founders succeeding in these deep tech categories, securing impressive venture capital leads from firms like a16z, Accel, Sequoia, and Bessemer. Those are the types of deals we hunt our way into.

  Mike Collins:
  And that’s really what it’s about—getting access to fantastic companies. Yes, there’s a funding gap for women, but the great companies are still competitive deals. If you’re an entrepreneur running a great company and deciding who to bring into your financing, there has to be a value-add, especially from a co-investor.

  Through the Alumni Affinity and what we’re building with the Women’s Fund, yes, we’ll write a check on the same terms as your lead, but we can help you disproportionately to our check size.

  Laura Rippy:
  That’s right, Mike.

  Mike Collins:
  I’m proud of how we’ve done that. I think the promise to a female founding CEO—that you’ve got Benchmark leading your A round, we want to do 15%, and on top of that we have this tremendous network of alumni connections, other female entrepreneurs, 350 of them already backed by AV, and a source of capital from women who not only want returns but want to support and empower other women—is incredibly compelling.

  Many of these investors are now in positions of power and expertise. From a CEO’s perspective, that sounds pretty good to me.

  Laura Rippy:
  I’m on board as well, Mike.

  Mike Collins:
  Yeah, so we’ll wrap this up, Laura. Thanks for your time today. For any listener thinking, “This makes sense,” and wanting more content, company updates, or to explore investing in our funds—how can they get involved?

  Laura Rippy:
  Absolutely. The website is av.vc/funds/womens. If you’d like to email us directly, it’s [email protected], and we can start the conversation there.

  We also have a LinkedIn page—reach out to us. We’re building a community here, and we succeed because of the strength of that community—stirring the pot between our founders, venture partners, and investors.

  We welcome participation, and I’m so glad to have this opportunity to talk with you, Mike. I hope it inspires folks to join us for the AV Women’s Fund because, as you say, it’s both: great return potential and putting your money to work backing fiery female founders.

  Mike Collins:
  Yeah, excellent. Thank you, Laura.

  Laura Rippy:
  Thanks, Mike. Hey, everyone. I’d love to take a moment to tell you a bit about Alumni Ventures and our Women’s Fund. AV offers individuals the opportunity to invest in startups shaping the future. We build intentionally diversified portfolios, co-investing alongside established lead venture investors.

  Today, we serve over 10,000 individual investors who have invested over $1.3 billion. With our Alumni Ventures Women’s Fund, you’ll have the opportunity to help us invest in fiery female founders.

  We’re starting from a position of strength: AV has already invested in over 350 startups founded, co-founded, or led by women. We see the Women’s Fund as a great opportunity. PitchBook reports that female-led startups are more capital-efficient and exit faster, yet only receive 15% of all venture capital dollars.

  Join us to invest in female-led startups innovating in sectors like cybersecurity, machine learning, space, FemTech, AI, and robotics. Join us in the Alumni Ventures Women’s Fund to back a diversified portfolio of female-led, high-velocity startups as they change the world.

  If you’d like to learn more, visit us at av.vc/funds/womens.

  Mike Collins:
  Thanks, Laura. I haven’t been this excited about a new AV community and its potential since we started our first alumni fund almost a decade ago. I think Laura, backed by her team and our community, is going to create the most powerful women’s fund in the world.

  I hope you consider supporting them and getting involved. I hope you enjoyed this episode of the Tech Optimist Podcast. If you share an interest in technology, entrepreneurship, and venture investing, please subscribe and send us your comments.

  In a capitalist system, VC and entrepreneurship are the tip of the spear. We look forward to talking to phenomenal VCs and entrepreneurs who are solving problems and building companies. Join us.

  Narrator:
  Thanks again for tuning into Tech Optimist. If you enjoyed this episode, we’d really appreciate it if you give us a rating on whichever podcast app you’re using, and remember to subscribe to keep up with weekly episodes.

  The Tech Optimist welcomes any questions, comments, or segment suggestions. Please email us at [email protected], and be sure to visit our website at av.vc.

  Thanks again. Until next time.