Ami: Venture can be a great way to capitalize a business that could become profitable— small or medium-sized enterprise. This approach is very different than unicorn hunting, right? This is very different than growth at all costs. This is very different than large, massive, high-priced rounds where VC kind of piles into a handful of startups. It’s based on a disciplined underwriting and requiring founders to be very focused on unit economics, which is quite different than that unicorn hunting credo of venture capital. I think when you approach venture capital that way, you will see a great deal of white space investment opportunity.
Aoifinn Devitt: I’m Aoifinn Devitt, and welcome to the 50 Faces Podcast, a podcast committed to revealing the richness and diversity of the world of investment by focusing on its people and their stories. This series is supported by BenefitStreet Partners. BenefitStreet Partners is a leading global alternative credit asset manager offering clients investment solutions across a broad range of complementary credit strategies, including in direct lending, special situations, structured credit, high yield bonds, leveraged loans, and commercial real estate debt and equity. This episode is also supported by PIMCO, a global leader in active fixed income with deep expertise across public and private markets. PIMCO invests their clients’ capital in income and credit opportunities to span the liquidity spectrum, leveraging their decades of expertise navigating complex debt markets. I’m joined today by Ami Ghilani, who is co-founder and managing partner of Tipt Ventures. A venture capital firm investing in companies reimagining sports starting with her. She is a board member of Beauty by Imagination, BBI, a PE-backed beauty platform, a strategic advisor to LCN Park Ventures, a venture capital firm backed by the ownership group of the LA Dodgers, and holds a number of other board roles. She spent over 10 years at Dick’s Sporting Goods, where she focused on identifying M&A investment and other strategic or non-traditional opportunities to enhance the Dick’s athlete experience. And drive Dick’s long-term strategy. Welcome, Ami. Thanks for joining me today.
Ami: Thank you for having me.
Aoifinn Devitt: Well, this is such a fascinating set of interests and board roles and involvement I’ve already cited there. I’d love to go back, though, to your background and how you entered into this investment area and hear whether there were any surprising turns along the way.
Ami: Yeah. You know, my turn into finance itself was surprising. I actually started my career as an M&A and capital markets attorney. I worked in big law for nearly 10 years before going to Dick’s Sporting Goods. And I went to Dick’s Sporting Goods as a corporate attorney, and I loved being a deal lawyer, but I was getting very engaged with my clients and on the deals, on the financial and strategic rationale for every deal. Like, I just, I was a deal junkie and I loved doing the work. And I was very lucky to have clients both when I was at the law firm and internal clients at Dick’s Sporting Goods who would spend time with me. Walking through the model and the strategy and really including me as a business partner instead of just a legal partner. And then a few years into my time at Dick’s Sporting Goods, Ed Stack, who is the controlling shareholder of Dick’s Sporting Goods and at that time both the chairman and CEO, asked me to be his chief of staff. This is in 2016 when Amazon was going to displace all, you know, big box retail, and there’s quite a bit going on both, you know, from a transformation perspective in retail. And I’d been on his radar because I’d shown a great deal of financial and business acumen in my legal work and in my deal work for Dick’s Sporting Goods and was in board meetings often talking about the work that we were doing from both a legal and non-legal side. And this was in 2016, and that was my turn into finance. You know, I didn’t ask for it. I was invited into it. And after 2 years as his chief of staff, I ultimately went on to lead corporate development, which is our M&A practice and building what is now known as DSG Ventures, which is Dick’s Sporting Goods Venture Investing Program. Look, it’s been, you know, over a decade now since I moved over to the finance side. And I have found that it speaks to my skill set in a more fulsome way than just being a deal lawyer. I love the numbers. And from time to time, I get asked by young attorneys how I shifted from the practice of law to the business side. It doesn’t happen very often, but it is known to happen. And so young attorneys will say, well, after I graduate from law school, how do I flip over to the business side? And over the years of answering that question, it has occurred to me that this really started for me when I was a kid. I’m actually the child of an entrepreneur. My dad, who has since passed, owned a small manufacturing business, and we lovingly called the business The Factory. And my mom was my dad’s business partner, and The Factory was essentially my sibling. And The Factory sat at the dinner table with me and my sister every night, and we talked about The Factory every night. And all through high school, my sister had left for college. It was the factory in me at the dinner table. And we would talk about successes, challenges. And my mom and dad had very different approaches to growth. And I was often the mediator. So my business and financial acumen was really honed at the dinner table. And I realize now that it was foundational in the development of those skills. And those skills are the skills that helped me be a good deal lawyer. And now help me be a good deal maker.
Aoifinn Devitt: Absolutely fascinating. I haven’t heard someone anthropomorphize the factory or a factory or a, a venture in quite the same way, but it is really interesting and of course very common. And I think it’s, it just totally illustrates how these entities and ventures sort of inhabit the, the fabric of who we are. And in light of that, um, how have you taken, say, some of these core beliefs that you grew up with into your approach to venture investing?
Ami: It’s a great question. My approach to venture investment is quite different than what the words venture and venture capital might evoke. I approach venture from my roots as a child of an entrepreneur of a small business. Venture can be a great way to capitalize a business that could become profitable, small or medium-sized enterprise. This approach is very different than unicorn hunting, right? This is very different than growth at all costs. This is very different than large, massive, high-priced rounds where VC kind of piles into a handful of startups. It’s based on a disciplined underwriting and requiring founders to be very focused on unit economics, which is quite different than that unicorn hunting credo of venture capital. I think when you approach venture capital that way, you will see a great deal of white space investment opportunity. And I would say when we look across our pipeline and what we are seeing cross our desk, we’ve been really pleased with the founder mentality and the shift of that mentality from growth at all costs to unit economics.
Aoifinn Devitt: Really interesting. And we could maybe return to that as we look in particular, maybe at some case studies within TIP Ventures. But moving to TIP Ventures now, what is your core focus and what makes it unique?
Ami: TIP Ventures is an investment firm built on the belief that the next wave of sports growth will be based on women and girls in the sports economy. So let’s talk about what we mean by sports. Most people think about sports as a game on the field, and more specifically, most people think about the professional game on the field. We see sports very differently. We see sports as an economy of businesses that is enabling the game from from peewee soccer to the Super Bowl. And if you break that down, this economy is made up of consumer, content, and enterprise businesses. And if you break down sports even further, you deconstruct what sports is, it’s really just an engagement model, right? It’s how we engage in something happening around us or in content. And when you look at it that way, sports becomes a beachhead to the broader engagement economy and another way to capture and retain attention, which is such a premium in today’s consumer economy.
Aoifinn Devitt: That beachhead concept clearly spawns adjacent businesses, and I know footwear, accessories, clothing, apparel, that is all part of the, of this thesis. But starting on the sports side and women’s sports in particular, where would you say we are in terms of, let’s use the analogy of the innings of a baseball game? In terms of getting women’s sports to the same level of engagement and attention as men’s sports?
Ami: Yeah, no, that’s a really great question. I want to first talk about how sports has evolved. You know, these days, based on all the headlines we see, you know, sports, there’s like, you know, an echo chamber that sports is an asset class. If you were to rewind the clock, so you said use the innings of a baseball game as an analogy. In the first innings of the game, I would say that sports is really a vanity asset. Ownership class for these assets was quite small. And that’s how it was for decades. And it wasn’t really until probably the last 5 or 10 years that you have seen that shift and the echo of sports as an asset class start to reverberate. And what this has led to is a great deal of dealmaking. So tra— actual trading of assets. Sports assets, so teams, league investments, and that trading is now happening at higher and higher valuation. So nearly every time there is a new trade or ownership change of a team on the men’s or the women’s side, we are seeing record ownership valuations and record media valuations. Let’s say that’s the middle innings. I think we’re headed into the, the last innings of the game. So let’s say that the last 3 innings. And, you know, where I really see this going, and I think the conversation is evolving, is sports as a vanity play to sports as an asset class. And now I think sports as a theme, one of many ways to invest in sports. And that’s where those adjacencies, right? Thinking about sports as consumer, content, enterprise goes, and investing in those adjacent spaces are at the end of the day critical to the growth of the asset itself. Because if you’re not telling the stories, if you’re not finding the audience in venue, out of venue, and what I would say far out of venue, then the valuations simply break, right? They’re not supported. You need the growth of those adjacent spaces. You need the growth of that attention economy in order for sports to continue to grow and the valuations to be supported. So I like to say that sports is an investment theme instead of an asset class.
Aoifinn Devitt: And then in terms of women’s sports in particular, clearly coming from a lagging position, but getting increased attention. I’m sitting here in the UK. I know UK, British, you know, female soccer has got a lot more attention recently, a lot more popularity. It already is at that level in the US. A lot of controversy around pay and viewership. How do you compare the engagement trajectories of the two?
Ami: Yeah, no. So women’s sports is at a really interesting point. I like to say that there’s a confluence of events that has happened. One is from the United States perspective, we’re 50 years into Title IX. And so girls playing sports is just kind of the norm, right? And the girls really are playing younger, faster, harder, and longer than ever before. So the actual engagement of girls and now women— you and I are probably the first generation where we had equal opportunity to sports— is actually higher, right? They’re, they’re engaging in the econ— sports economy at higher rates. You combine that with the disintermediation of traditional media. Because now all of a sudden content is available beyond linear. So the engagement in the content is across social, and it’s deeply democratized. For women’s sports, this confluence, the confluence of those two things, is incredible fuel for their growth. And it can grow in ways that are quite disconnected and unconstrained by the men’s sports properties, where they might be tied to long-term linear deals, long-term corporate partnerships. Their data could be held and housed in systems that are quite, at this point, antiquated. Women’s sports has this opportunity to leapfrog a number of, call it, the structures and the platforms that men’s sports is built on. And really take advantage of that confluence of 50 years of Title IX and the disintermediation of linear TV, allowing women’s sports properties to show up in really great ways across spaces. They can show up on TikTok. They can show up in fashion and in culture. They can show up for the little girls. They can show up for women. It’s wide open. In a way that is unprecedented and is just really, really quite wide open for women’s sports.
Aoifinn Devitt: So interesting. And I don’t know if you could maybe continue to make this, I suppose, kind of visceral for us in terms of an experience by speaking about some of the case studies perhaps in, you know, in whatever form you can in terms of maybe examples of this. What occurs to me, you mentioned leapfrogging conventional structures and pipelines. Thinking of things like apparel, how the kind of indie brands can sometimes get the same attention thanks to social media influencers as maybe a large sports brand like Nike and Adidas, for example. There’s definitely a lot of influence of that. And equally so, any other ways we can see a lot of Serena Williams, for example, prominent female sports players, not only raising the profile of their sport and of women in sport, and the Winter Olympics was another great example of that. But also putting their money where their mouths are in terms of investing too. Any kind of case studies you can point to today to show this in action?
Ami: Yeah, sure. I’m going to actually give you two because they’re very different, but they speak to the same opportunity. The first is an investment that we have made. It’s called AIDA Sports. AIDA Sports is a soccer cleat designed for the female foot. We might say that that has existed before, but by and large, girls and women have been playing in shoes that suffer from pinky take it and shrink it, where the last of the shoe— the last is a foundation of the shoe— is actually based on the men’s foot, and then they shrink the sizing, add some pinks and purples or maybe some glitter, and they call it a girls product. As we mentioned earlier on the call, what girls are playing harder and faster and longer than ever before, and the injuries are showing up, right? Girls are 3 times more likely to have an injury, an ACL injury, than boys who play. The New York Times actually just ran a very big story on this and they put that risk percentage even higher. And we don’t really have good reasons, but we know that we need better gear. So AIDA Sports is providing performance footwear. This is not fashion. This is not lifestyle. This is what you’re playing in when you’re playing your hardest. If we look at the 3 fastest growing sports for girls, it is soccer, flag football, and lacrosse. These are all cleated sports. Cleats are rounding error for the big brands, right? Girls’ cleats are rounding error for the big brands. This is a use case and a case study where there’s a very specific need that is not being met at the quality that is required. And so we’re— that’s one that we think absolutely hits a white space. I’m going to give you a different example, which is very different, which is about YouTube. When we think about how to reach the audience, a YouTube-first strategy is a very, very viable strategy now. YouTube is replacing traditional TV, right? And if we kind of break up with models, or I will say pressure test models where games have to be shown live on linear TV or even behind a paywall, and we ask ourselves, What does it look like if we go YouTube first? It’s really interesting, right? That’s where young people are consuming content. That YouTube-first strategy really takes advantage of the viewership and engagement behaviors of Gen Z, Gen A, and now what we’re seeing in the earliest years for Gen Beta.
Aoifinn Devitt: We’re going to hear from one of the sponsors of the series, Benefit Street Partners, BSP. I sat down with Rich Byrne, President and CEO of BSP, and asked him why working at a firm of this size creates unique opportunities to set culture.
Speaker C: At Benefit Street Partners, we’re barely 250 people, and that’s still a size where you can have your fingers in all the pies and know all the people. I know the people less well maybe than when there was 100 people, but you know, you can still know all the people. I think there’ll be a point in our growth where that’s going to much more difficult to do. But while we’re at this size, I think that culture is something that we can carefully curate to, you know, be a powerful weapon for us. I think it involves, and doing that is, you know, just like I said, sort of leading by example.
Aoifinn Devitt: And now back to the show. That’s so interesting. I think, you know, again, back to that leapfrogging and not being able to take advantage of AI, et cetera. I’d love to just sneak in a question about one of your boards, Beauty by Imagination. Private equity-backed beauty platform, because it gets to this kind of share of wallet. You know, we’ve spoken a little bit about the lipstick index. I have at least in the past in terms of the, the beauty items that consumers are still willing to spend money on. And I would think equally one’s daughter’s cleats and the, the health of their, their foot is probably another thing that has become kind of non-negotiable. Based on your insights as a board member there, as well as your work in the, the sports area, do you have any comment on the evolution of spending preferences?
Ami: Yeah, it’s interesting. A moment ago you mentioned AI, and look, I think content is commoditized, and AI commoditizes content even more. And in that environment, sports, I believe, is a net winner because I think there is a premium to in real life content. And as a brand, when you’re thinking about marketing strategies and how you speak to your consumer, certainly there is going to be a segment of your brand marketing, performance marketing, and your overall marketing program that leverages AI, right? And that’s absolutely something that is necessary to do. But as you think about how to reach and engage your consumer and to get that, call it top of mind in order to get share of wallet, the association with sports in real life experience, right? Something that has that IRL premium, I think ends up being a very important part of your brand storytelling. And that storytelling will be more valuable, at least in my assessment, than deeply commoditized content that is AI-driven.
Aoifinn Devitt: Absolutely agree with you on storytelling. And again, probably the reason why the Winter Olympics were so fantastically popular and captured the imagination right at the, at the time, I think, when people needed distraction. And one last question on the venture space before moving to some personal reflections. It’s around whether you’ve perceived the LP use case, or at least what they’re looking for in their venture manager. Is there any combination of impact that’s sort of starting to come in and overlay the need for return? Is it long-term partnerships and just, you know, kind of access to innovation that, that LPs are seeking as well?
Ami: Yeah, it’s interesting. You know, based on the fact that we have a gender strategy, I would have expected more of a focus on impact, and we are not an impact firm. I would have expected more of a focus on that from our investors. But what we have found has really resonated is less impact and less gender, but more that what I would call the re-envisioning of venture as a good funding source for small and medium businesses, right? I think a lot of our LPs have venture in within their portfolios, They may have seen returns lower than expectations. Some of them are still waiting for returns as the cash has been slower to cycle back. And I think the awareness of the opportunities in that small and medium business environment and the need for funding sources and creating funding structures for that space has grown. And I think there’s a great deal of excitement around those spaces, particularly as middle market is, you know, call it more, less sensitive to externalities, right? Interest rate, macro environment, geopolitical risk, that, that middle market environment feels safe, where there still continue to be high quality opportunities. And we have found that LPs really like our focus in that sector.
Aoifinn Devitt: Lady, well, let’s move into some personal reflections now. So obviously venture capital is not immune from a certain amount of volatility and uncertainty as a career. I’d love to ask you, over the course of your career, moving from the corporate lawyer side into industry and now into your own firm, have there been any highs or lows you can speak to? And in particular, with respect to the lows, any lessons learned?
Ami: Most corporate lawyers would disagree with what I’m about to say, but the practice of law is a very comfortable space. And I think most lawyers would, you know, because it’s a very high stress, high anxiety career, would disagree with the description of it as a comfortable space. But at the end of the day, it is comfortable because you don’t have accountability for the investment decision, right? How the money moves. And when you step into the business role and you take accountability for that decision-making, for the movement of capital, it’s scary. It is very scary. And so I would say the low points have been fear, right? The low points have been what I would say when I was unable to make the decision and I had to go to somebody else, you know, the CFO, the CEO, you know, to say, I, I can’t make this decision. And it’s overcoming that fear, absolutely critical in order to fully transition over to the finance side. You have to be able to make decisions on the movement of capital and brave enough to be accountable for those decisions. But once you get there, the highs are really great, right? So for me, I get to be a professional cheerleader in, in the sense that my job as an investor in businesses is to cheer for their success. And so my highs are when businesses and founders achieve milestones, even if they’re little milestones. It’s when the unit economics come within line of sight. It’s when there are promotions. There are celebrations. Those are the absolute high points in my work. And so I like to say being a VC is in many ways just being a professional cheerleader.
Aoifinn Devitt: I love it. And it’s a great segue to my next question, which is around cheerleaders that have been there for you. You think about VCs as being, as you said, cheerleaders as well as mentors, and just, uh, they’re your counselors almost for, for some of the founders. Has there been any key people in your career— and this does not have to be an exhaustive list in terms of people who have had a formative role?
Ami: Yeah, well, of course, I have to start with Ed Stack of Dick’s Sporting Goods. He took a bet on me. He’s the one who pulled me out of the legal department, let me sit on his right-hand side for two very critical transformational years for Dick’s Sporting Goods. And he invested a great deal in my development. He would sit down with me. I’d ask him a list of questions and at the end of the day, before it was time to go home, he would spend the time with me to walk me through some of his thinking. And more than that, he gave me voice, right? I wasn’t a silent chief of staff. I was quite engaged. I was quite vocal. And he gave me the space to do that. But I would say there was, in addition to him, somebody else. He was a CFO at the time, Lee Belitsky, now retired. And he said something to me when I left the Chief of Staff role and stepped into the corporate development role. And he said something to me that nobody had ever said to me and that has stayed with me. And it was very simple. He said, now you have to be a rainmaker. And it sounded silly at the time and obvious, but it has percolated. And really seeped into me. And what he was expressing was the shift in the role from a facilitative role that you are as a lawyer or as a chief of staff to that decision-making role where you bring new ideas and you evaluate new ideas and you make decisions about new ideas. So you have to be a rainmaker is something that has seeped in, and I remind myself, I would say at least once a month that I’m in this seat, I have this privilege of being a professional cheerleader because I was willing to step into that role.
Aoifinn Devitt: And I think a flip side of that is probably the dealing with failure, because as you mentioned, when you are a facilitator, you’re facilitating the successes and the failures, but you’re not accountable for them. And of course, in venture, not only as the perpetrator of these deals, but also as an investor in venture, you have to learn to stomach a certain amount of failure. And that’s a lot of what we talk about in these podcasts is, you know, building the thick skin and the mindset to cope with that and not see it as a permanent setback, but as a, I suppose, a natural learning experience, which is a theme that’s come up over and over again. Which brings me to the last question. And I think we’ve kind of echoing a little bit already your creed and motto, but if there’s any last words of wisdom you can leave us with or anything you maybe wish you’d known in those early stages of your career that you know now?
Ami: You know, believe in people. I wish— these two things will go together. One is, um, smile more, and the second is believe in people. And they go together. They go together because when you smile more, you get more from people, and it helps you build their belief in that person. You know, my dad believed every person has something, has a strength. We have to find it. And it’s much easier to find that strength when you smile, right? And I think for most of my career, I didn’t. For the first decade of my career, I can’t— I probably rarely smiled because my job was risk assessment and risk management and risk mitigation. That’s what a lawyer does. And so, you know, people tend to not be smiley when they’re talking about the downside scenario. But then when you have to flip to the upside scenario, right, the investment case, the why of the decision, you realize that you need to get much more out of a person, right? You need to understand where they’re coming from. And to do that, you need to be friendly and show that you are a safe space. So I would say smile more. And believe in people.
Aoifinn Devitt: Well, that is a wonderful way to bring this to a close. I’ve spoken with many sports stars actually who now have evolved and changed their career into finance. And one theme throughout is the importance of a coach. A really good coach can be formative for their entire life and their, their career, and not only in sports, elsewhere. And what you’re describing as your cheerleader-in-chief role is very similar to that coach role. And as we think about the exciting and dynamic world of women’s sports. I couldn’t be more enthusiastic to think about coaches and cheerleaders like you in the corner of this fast-evolving space. We would look forward to watching with interest what comes next. And thank you so much for coming here and sharing your insights with us.
Ami: Thank you very much for having me.
Aoifinn Devitt: I’m Aoifinn Devitt. Thank you for listening to the 50 Faces Podcast. If you liked what you heard and would like to tune in to hear more inspiring investors and their personal journeys, please subscribe on Apple Podcasts or wherever you get your podcasts. This podcast is for informational purposes only and should not be construed as investment advice, and all views are personal and should not be attributed to the organizations and affiliations of the host or any guest.
Ami: Venture can be a great way to capitalize a business that could become profitable— small or medium-sized enterprise. This approach is very different than unicorn hunting, right? This is very different than growth at all costs. This is very different than large, massive, high-priced rounds where VC kind of piles into a handful of startups. It’s based on a disciplined underwriting and requiring founders to be very focused on unit economics, which is quite different than that unicorn hunting credo of venture capital. I think when you approach venture capital that way, you will see a great deal of white space investment opportunity.
Aoifinn Devitt: I’m Aoifinn Devitt, and welcome to the 50 Faces Podcast, a podcast committed to revealing the richness and diversity of the world of investment by focusing on its people and their stories. This series is supported by BenefitStreet Partners. BenefitStreet Partners is a leading global alternative credit asset manager offering clients investment solutions across a broad range of complementary credit strategies, including in direct lending, special situations, structured credit, high yield bonds, leveraged loans, and commercial real estate debt and equity. This episode is also supported by PIMCO, a global leader in active fixed income with deep expertise across public and private markets. PIMCO invests their clients’ capital in income and credit opportunities to span the liquidity spectrum, leveraging their decades of expertise navigating complex debt markets. I’m joined today by Ami Ghilani, who is co-founder and managing partner of Tipt Ventures. A venture capital firm investing in companies reimagining sports starting with her. She is a board member of Beauty by Imagination, BBI, a PE-backed beauty platform, a strategic advisor to LCN Park Ventures, a venture capital firm backed by the ownership group of the LA Dodgers, and holds a number of other board roles. She spent over 10 years at Dick’s Sporting Goods, where she focused on identifying M&A investment and other strategic or non-traditional opportunities to enhance the Dick’s athlete experience. And drive Dick’s long-term strategy. Welcome, Ami. Thanks for joining me today.
Ami: Thank you for having me.
Aoifinn Devitt: Well, this is such a fascinating set of interests and board roles and involvement I’ve already cited there. I’d love to go back, though, to your background and how you entered into this investment area and hear whether there were any surprising turns along the way.
Ami: Yeah. You know, my turn into finance itself was surprising. I actually started my career as an M&A and capital markets attorney. I worked in big law for nearly 10 years before going to Dick’s Sporting Goods. And I went to Dick’s Sporting Goods as a corporate attorney, and I loved being a deal lawyer, but I was getting very engaged with my clients and on the deals, on the financial and strategic rationale for every deal. Like, I just, I was a deal junkie and I loved doing the work. And I was very lucky to have clients both when I was at the law firm and internal clients at Dick’s Sporting Goods who would spend time with me. Walking through the model and the strategy and really including me as a business partner instead of just a legal partner. And then a few years into my time at Dick’s Sporting Goods, Ed Stack, who is the controlling shareholder of Dick’s Sporting Goods and at that time both the chairman and CEO, asked me to be his chief of staff. This is in 2016 when Amazon was going to displace all, you know, big box retail, and there’s quite a bit going on both, you know, from a transformation perspective in retail. And I’d been on his radar because I’d shown a great deal of financial and business acumen in my legal work and in my deal work for Dick’s Sporting Goods and was in board meetings often talking about the work that we were doing from both a legal and non-legal side. And this was in 2016, and that was my turn into finance. You know, I didn’t ask for it. I was invited into it. And after 2 years as his chief of staff, I ultimately went on to lead corporate development, which is our M&A practice and building what is now known as DSG Ventures, which is Dick’s Sporting Goods Venture Investing Program. Look, it’s been, you know, over a decade now since I moved over to the finance side. And I have found that it speaks to my skill set in a more fulsome way than just being a deal lawyer. I love the numbers. And from time to time, I get asked by young attorneys how I shifted from the practice of law to the business side. It doesn’t happen very often, but it is known to happen. And so young attorneys will say, well, after I graduate from law school, how do I flip over to the business side? And over the years of answering that question, it has occurred to me that this really started for me when I was a kid. I’m actually the child of an entrepreneur. My dad, who has since passed, owned a small manufacturing business, and we lovingly called the business The Factory. And my mom was my dad’s business partner, and The Factory was essentially my sibling. And The Factory sat at the dinner table with me and my sister every night, and we talked about The Factory every night. And all through high school, my sister had left for college. It was the factory in me at the dinner table. And we would talk about successes, challenges. And my mom and dad had very different approaches to growth. And I was often the mediator. So my business and financial acumen was really honed at the dinner table. And I realize now that it was foundational in the development of those skills. And those skills are the skills that helped me be a good deal lawyer. And now help me be a good deal maker.
Aoifinn Devitt: Absolutely fascinating. I haven’t heard someone anthropomorphize the factory or a factory or a, a venture in quite the same way, but it is really interesting and of course very common. And I think it’s, it just totally illustrates how these entities and ventures sort of inhabit the, the fabric of who we are. And in light of that, um, how have you taken, say, some of these core beliefs that you grew up with into your approach to venture investing?
Ami: It’s a great question. My approach to venture investment is quite different than what the words venture and venture capital might evoke. I approach venture from my roots as a child of an entrepreneur of a small business. Venture can be a great way to capitalize a business that could become profitable, small or medium-sized enterprise. This approach is very different than unicorn hunting, right? This is very different than growth at all costs. This is very different than large, massive, high-priced rounds where VC kind of piles into a handful of startups. It’s based on a disciplined underwriting and requiring founders to be very focused on unit economics, which is quite different than that unicorn hunting credo of venture capital. I think when you approach venture capital that way, you will see a great deal of white space investment opportunity. And I would say when we look across our pipeline and what we are seeing cross our desk, we’ve been really pleased with the founder mentality and the shift of that mentality from growth at all costs to unit economics.
Aoifinn Devitt: Really interesting. And we could maybe return to that as we look in particular, maybe at some case studies within TIP Ventures. But moving to TIP Ventures now, what is your core focus and what makes it unique?
Ami: TIP Ventures is an investment firm built on the belief that the next wave of sports growth will be based on women and girls in the sports economy. So let’s talk about what we mean by sports. Most people think about sports as a game on the field, and more specifically, most people think about the professional game on the field. We see sports very differently. We see sports as an economy of businesses that is enabling the game from from peewee soccer to the Super Bowl. And if you break that down, this economy is made up of consumer, content, and enterprise businesses. And if you break down sports even further, you deconstruct what sports is, it’s really just an engagement model, right? It’s how we engage in something happening around us or in content. And when you look at it that way, sports becomes a beachhead to the broader engagement economy and another way to capture and retain attention, which is such a premium in today’s consumer economy.
Aoifinn Devitt: That beachhead concept clearly spawns adjacent businesses, and I know footwear, accessories, clothing, apparel, that is all part of the, of this thesis. But starting on the sports side and women’s sports in particular, where would you say we are in terms of, let’s use the analogy of the innings of a baseball game? In terms of getting women’s sports to the same level of engagement and attention as men’s sports?
Ami: Yeah, no, that’s a really great question. I want to first talk about how sports has evolved. You know, these days, based on all the headlines we see, you know, sports, there’s like, you know, an echo chamber that sports is an asset class. If you were to rewind the clock, so you said use the innings of a baseball game as an analogy. In the first innings of the game, I would say that sports is really a vanity asset. Ownership class for these assets was quite small. And that’s how it was for decades. And it wasn’t really until probably the last 5 or 10 years that you have seen that shift and the echo of sports as an asset class start to reverberate. And what this has led to is a great deal of dealmaking. So tra— actual trading of assets. Sports assets, so teams, league investments, and that trading is now happening at higher and higher valuation. So nearly every time there is a new trade or ownership change of a team on the men’s or the women’s side, we are seeing record ownership valuations and record media valuations. Let’s say that’s the middle innings. I think we’re headed into the, the last innings of the game. So let’s say that the last 3 innings. And, you know, where I really see this going, and I think the conversation is evolving, is sports as a vanity play to sports as an asset class. And now I think sports as a theme, one of many ways to invest in sports. And that’s where those adjacencies, right? Thinking about sports as consumer, content, enterprise goes, and investing in those adjacent spaces are at the end of the day critical to the growth of the asset itself. Because if you’re not telling the stories, if you’re not finding the audience in venue, out of venue, and what I would say far out of venue, then the valuations simply break, right? They’re not supported. You need the growth of those adjacent spaces. You need the growth of that attention economy in order for sports to continue to grow and the valuations to be supported. So I like to say that sports is an investment theme instead of an asset class.
Aoifinn Devitt: And then in terms of women’s sports in particular, clearly coming from a lagging position, but getting increased attention. I’m sitting here in the UK. I know UK, British, you know, female soccer has got a lot more attention recently, a lot more popularity. It already is at that level in the US. A lot of controversy around pay and viewership. How do you compare the engagement trajectories of the two?
Ami: Yeah, no. So women’s sports is at a really interesting point. I like to say that there’s a confluence of events that has happened. One is from the United States perspective, we’re 50 years into Title IX. And so girls playing sports is just kind of the norm, right? And the girls really are playing younger, faster, harder, and longer than ever before. So the actual engagement of girls and now women— you and I are probably the first generation where we had equal opportunity to sports— is actually higher, right? They’re, they’re engaging in the econ— sports economy at higher rates. You combine that with the disintermediation of traditional media. Because now all of a sudden content is available beyond linear. So the engagement in the content is across social, and it’s deeply democratized. For women’s sports, this confluence, the confluence of those two things, is incredible fuel for their growth. And it can grow in ways that are quite disconnected and unconstrained by the men’s sports properties, where they might be tied to long-term linear deals, long-term corporate partnerships. Their data could be held and housed in systems that are quite, at this point, antiquated. Women’s sports has this opportunity to leapfrog a number of, call it, the structures and the platforms that men’s sports is built on. And really take advantage of that confluence of 50 years of Title IX and the disintermediation of linear TV, allowing women’s sports properties to show up in really great ways across spaces. They can show up on TikTok. They can show up in fashion and in culture. They can show up for the little girls. They can show up for women. It’s wide open. In a way that is unprecedented and is just really, really quite wide open for women’s sports.
Aoifinn Devitt: So interesting. And I don’t know if you could maybe continue to make this, I suppose, kind of visceral for us in terms of an experience by speaking about some of the case studies perhaps in, you know, in whatever form you can in terms of maybe examples of this. What occurs to me, you mentioned leapfrogging conventional structures and pipelines. Thinking of things like apparel, how the kind of indie brands can sometimes get the same attention thanks to social media influencers as maybe a large sports brand like Nike and Adidas, for example. There’s definitely a lot of influence of that. And equally so, any other ways we can see a lot of Serena Williams, for example, prominent female sports players, not only raising the profile of their sport and of women in sport, and the Winter Olympics was another great example of that. But also putting their money where their mouths are in terms of investing too. Any kind of case studies you can point to today to show this in action?
Ami: Yeah, sure. I’m going to actually give you two because they’re very different, but they speak to the same opportunity. The first is an investment that we have made. It’s called AIDA Sports. AIDA Sports is a soccer cleat designed for the female foot. We might say that that has existed before, but by and large, girls and women have been playing in shoes that suffer from pinky take it and shrink it, where the last of the shoe— the last is a foundation of the shoe— is actually based on the men’s foot, and then they shrink the sizing, add some pinks and purples or maybe some glitter, and they call it a girls product. As we mentioned earlier on the call, what girls are playing harder and faster and longer than ever before, and the injuries are showing up, right? Girls are 3 times more likely to have an injury, an ACL injury, than boys who play. The New York Times actually just ran a very big story on this and they put that risk percentage even higher. And we don’t really have good reasons, but we know that we need better gear. So AIDA Sports is providing performance footwear. This is not fashion. This is not lifestyle. This is what you’re playing in when you’re playing your hardest. If we look at the 3 fastest growing sports for girls, it is soccer, flag football, and lacrosse. These are all cleated sports. Cleats are rounding error for the big brands, right? Girls’ cleats are rounding error for the big brands. This is a use case and a case study where there’s a very specific need that is not being met at the quality that is required. And so we’re— that’s one that we think absolutely hits a white space. I’m going to give you a different example, which is very different, which is about YouTube. When we think about how to reach the audience, a YouTube-first strategy is a very, very viable strategy now. YouTube is replacing traditional TV, right? And if we kind of break up with models, or I will say pressure test models where games have to be shown live on linear TV or even behind a paywall, and we ask ourselves, What does it look like if we go YouTube first? It’s really interesting, right? That’s where young people are consuming content. That YouTube-first strategy really takes advantage of the viewership and engagement behaviors of Gen Z, Gen A, and now what we’re seeing in the earliest years for Gen Beta.
Aoifinn Devitt: We’re going to hear from one of the sponsors of the series, Benefit Street Partners, BSP. I sat down with Rich Byrne, President and CEO of BSP, and asked him why working at a firm of this size creates unique opportunities to set culture.
Speaker C: At Benefit Street Partners, we’re barely 250 people, and that’s still a size where you can have your fingers in all the pies and know all the people. I know the people less well maybe than when there was 100 people, but you know, you can still know all the people. I think there’ll be a point in our growth where that’s going to much more difficult to do. But while we’re at this size, I think that culture is something that we can carefully curate to, you know, be a powerful weapon for us. I think it involves, and doing that is, you know, just like I said, sort of leading by example.
Aoifinn Devitt: And now back to the show. That’s so interesting. I think, you know, again, back to that leapfrogging and not being able to take advantage of AI, et cetera. I’d love to just sneak in a question about one of your boards, Beauty by Imagination. Private equity-backed beauty platform, because it gets to this kind of share of wallet. You know, we’ve spoken a little bit about the lipstick index. I have at least in the past in terms of the, the beauty items that consumers are still willing to spend money on. And I would think equally one’s daughter’s cleats and the, the health of their, their foot is probably another thing that has become kind of non-negotiable. Based on your insights as a board member there, as well as your work in the, the sports area, do you have any comment on the evolution of spending preferences?
Ami: Yeah, it’s interesting. A moment ago you mentioned AI, and look, I think content is commoditized, and AI commoditizes content even more. And in that environment, sports, I believe, is a net winner because I think there is a premium to in real life content. And as a brand, when you’re thinking about marketing strategies and how you speak to your consumer, certainly there is going to be a segment of your brand marketing, performance marketing, and your overall marketing program that leverages AI, right? And that’s absolutely something that is necessary to do. But as you think about how to reach and engage your consumer and to get that, call it top of mind in order to get share of wallet, the association with sports in real life experience, right? Something that has that IRL premium, I think ends up being a very important part of your brand storytelling. And that storytelling will be more valuable, at least in my assessment, than deeply commoditized content that is AI-driven.
Aoifinn Devitt: Absolutely agree with you on storytelling. And again, probably the reason why the Winter Olympics were so fantastically popular and captured the imagination right at the, at the time, I think, when people needed distraction. And one last question on the venture space before moving to some personal reflections. It’s around whether you’ve perceived the LP use case, or at least what they’re looking for in their venture manager. Is there any combination of impact that’s sort of starting to come in and overlay the need for return? Is it long-term partnerships and just, you know, kind of access to innovation that, that LPs are seeking as well?
Ami: Yeah, it’s interesting. You know, based on the fact that we have a gender strategy, I would have expected more of a focus on impact, and we are not an impact firm. I would have expected more of a focus on that from our investors. But what we have found has really resonated is less impact and less gender, but more that what I would call the re-envisioning of venture as a good funding source for small and medium businesses, right? I think a lot of our LPs have venture in within their portfolios, They may have seen returns lower than expectations. Some of them are still waiting for returns as the cash has been slower to cycle back. And I think the awareness of the opportunities in that small and medium business environment and the need for funding sources and creating funding structures for that space has grown. And I think there’s a great deal of excitement around those spaces, particularly as middle market is, you know, call it more, less sensitive to externalities, right? Interest rate, macro environment, geopolitical risk, that, that middle market environment feels safe, where there still continue to be high quality opportunities. And we have found that LPs really like our focus in that sector.
Aoifinn Devitt: Lady, well, let’s move into some personal reflections now. So obviously venture capital is not immune from a certain amount of volatility and uncertainty as a career. I’d love to ask you, over the course of your career, moving from the corporate lawyer side into industry and now into your own firm, have there been any highs or lows you can speak to? And in particular, with respect to the lows, any lessons learned?
Ami: Most corporate lawyers would disagree with what I’m about to say, but the practice of law is a very comfortable space. And I think most lawyers would, you know, because it’s a very high stress, high anxiety career, would disagree with the description of it as a comfortable space. But at the end of the day, it is comfortable because you don’t have accountability for the investment decision, right? How the money moves. And when you step into the business role and you take accountability for that decision-making, for the movement of capital, it’s scary. It is very scary. And so I would say the low points have been fear, right? The low points have been what I would say when I was unable to make the decision and I had to go to somebody else, you know, the CFO, the CEO, you know, to say, I, I can’t make this decision. And it’s overcoming that fear, absolutely critical in order to fully transition over to the finance side. You have to be able to make decisions on the movement of capital and brave enough to be accountable for those decisions. But once you get there, the highs are really great, right? So for me, I get to be a professional cheerleader in, in the sense that my job as an investor in businesses is to cheer for their success. And so my highs are when businesses and founders achieve milestones, even if they’re little milestones. It’s when the unit economics come within line of sight. It’s when there are promotions. There are celebrations. Those are the absolute high points in my work. And so I like to say being a VC is in many ways just being a professional cheerleader.
Aoifinn Devitt: I love it. And it’s a great segue to my next question, which is around cheerleaders that have been there for you. You think about VCs as being, as you said, cheerleaders as well as mentors, and just, uh, they’re your counselors almost for, for some of the founders. Has there been any key people in your career— and this does not have to be an exhaustive list in terms of people who have had a formative role?
Ami: Yeah, well, of course, I have to start with Ed Stack of Dick’s Sporting Goods. He took a bet on me. He’s the one who pulled me out of the legal department, let me sit on his right-hand side for two very critical transformational years for Dick’s Sporting Goods. And he invested a great deal in my development. He would sit down with me. I’d ask him a list of questions and at the end of the day, before it was time to go home, he would spend the time with me to walk me through some of his thinking. And more than that, he gave me voice, right? I wasn’t a silent chief of staff. I was quite engaged. I was quite vocal. And he gave me the space to do that. But I would say there was, in addition to him, somebody else. He was a CFO at the time, Lee Belitsky, now retired. And he said something to me when I left the Chief of Staff role and stepped into the corporate development role. And he said something to me that nobody had ever said to me and that has stayed with me. And it was very simple. He said, now you have to be a rainmaker. And it sounded silly at the time and obvious, but it has percolated. And really seeped into me. And what he was expressing was the shift in the role from a facilitative role that you are as a lawyer or as a chief of staff to that decision-making role where you bring new ideas and you evaluate new ideas and you make decisions about new ideas. So you have to be a rainmaker is something that has seeped in, and I remind myself, I would say at least once a month that I’m in this seat, I have this privilege of being a professional cheerleader because I was willing to step into that role.
Aoifinn Devitt: And I think a flip side of that is probably the dealing with failure, because as you mentioned, when you are a facilitator, you’re facilitating the successes and the failures, but you’re not accountable for them. And of course, in venture, not only as the perpetrator of these deals, but also as an investor in venture, you have to learn to stomach a certain amount of failure. And that’s a lot of what we talk about in these podcasts is, you know, building the thick skin and the mindset to cope with that and not see it as a permanent setback, but as a, I suppose, a natural learning experience, which is a theme that’s come up over and over again. Which brings me to the last question. And I think we’ve kind of echoing a little bit already your creed and motto, but if there’s any last words of wisdom you can leave us with or anything you maybe wish you’d known in those early stages of your career that you know now?
Ami: You know, believe in people. I wish— these two things will go together. One is, um, smile more, and the second is believe in people. And they go together. They go together because when you smile more, you get more from people, and it helps you build their belief in that person. You know, my dad believed every person has something, has a strength. We have to find it. And it’s much easier to find that strength when you smile, right? And I think for most of my career, I didn’t. For the first decade of my career, I can’t— I probably rarely smiled because my job was risk assessment and risk management and risk mitigation. That’s what a lawyer does. And so, you know, people tend to not be smiley when they’re talking about the downside scenario. But then when you have to flip to the upside scenario, right, the investment case, the why of the decision, you realize that you need to get much more out of a person, right? You need to understand where they’re coming from. And to do that, you need to be friendly and show that you are a safe space. So I would say smile more. And believe in people.
Aoifinn Devitt: Well, that is a wonderful way to bring this to a close. I’ve spoken with many sports stars actually who now have evolved and changed their career into finance. And one theme throughout is the importance of a coach. A really good coach can be formative for their entire life and their, their career, and not only in sports, elsewhere. And what you’re describing as your cheerleader-in-chief role is very similar to that coach role. And as we think about the exciting and dynamic world of women’s sports. I couldn’t be more enthusiastic to think about coaches and cheerleaders like you in the corner of this fast-evolving space. We would look forward to watching with interest what comes next. And thank you so much for coming here and sharing your insights with us.
Ami: Thank you very much for having me.
Aoifinn Devitt: I’m Aoifinn Devitt. Thank you for listening to the 50 Faces Podcast. If you liked what you heard and would like to tune in to hear more inspiring investors and their personal journeys, please subscribe on Apple Podcasts or wherever you get your podcasts. This podcast is for informational purposes only and should not be construed as investment advice, and all views are personal and should not be attributed to the organizations and affiliations of the host or any guest.
