Opening iGaming to New Founders, With Defy the Odds’ Kelly Kehn
Overview
What this episode is about
Kelly Kehn is co-founder of the startup launchpad Defy the Odds and founder of the All-In Diversity Project, and a long-time champion for women and underrepresented founders in iGaming. For the Season 2 finale, filmed in Lisbon, she makes a simple but pointed argument: inclusion is less about capability than about “the invite.”
Kelly breaks down how Defy the Odds connects founders, operators and investors, the fundraising truth of hundreds of conversations for a few yeses, the stage-by-stage metrics she actually watches, the ideas gaining traction (cinematic avatar live-dealer, skill games), what leaders forget when the numbers look good, and the trends she’s most excited about: women’s sport and regulatory tech. Her champion rule lands as the heart of it all: be kind, to others and to yourself.
The short version
Key takeaways
There's no shortage of capable people; what's missing is the invitation, plus the unfamiliar language of fundraising (cap table, CAC, LTV). Step one is making those resources available to everyone.
You'll talk to 300 to 500 people for a couple of yeses. Every no teaches you what investors care about and puts you on the path to a yes.
Early: is the founder capable, and do they understand the addressable market and the problem? At MVP: real interest and signed contracts. With revenue: are paying users sticking and growing? Awards in a deck mean little.
A black bottom line is worth celebrating, but bigger companies often lose sight of the vision, culture and people who got them there. The people you hire to go faster are human, and they build the brand and the fun.
Most pitches are too safe, or copy something that already exists (multiplayer blackjack). Do your competitive analysis, then get genuinely crazy, just not by ignoring the regulations.
In a small industry where everyone moves around, relationships are everything, and you have to forgive yourself when things don't go your way.
Full transcript
Read the conversation
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[00:00] 1. Intro: Kelly Kehn, founder of Defy the Odds
Host: Welcome to Bet It Drives, the show that drives you into the unexpected corners of iGaming. Our guest today is Kelly Kehn, founder of Defy the Odds and a champion for women in business. She helps grow iGaming companies and shows that inclusion is more than just words. Kelly, welcome.
Guest: Thank you. This is very exciting. I’ve never done anything remotely like this.
[00:35] 2. Pre-SBC mood and the Legends charity match
Host: We’re a day ahead of SBC, and today we’re attending the Legends charity match. Are you pumped up?
Guest: I am. This particular show, just after the summer, is so full of excitement because we’ve been away from each other. So many of my friends and colleagues are coming to this one. It feels like the rest of the year is about to start, and we’re going to have a great year.
[01:15] 3. Why industry events matter for startups
Host: These events are community-building factories, not just for the big boys but for new startups too, which is exactly your area.
Guest: Exactly. We love gaming, it’s so collegiate. Every time we come to one of these we make new friends and see old ones, and it’s hard to articulate to startups why it’s so important to be at the gaming events.
[01:56] 4. iGaming shows as full-scale entertainment
Host: I haven’t seen such scale and intense action anywhere, so much networking and so many parties. This is a show, not just an exhibition. I used to call out DJs, Randi Zuckerberg, Gary Vaynerchuk, celebrities, footballers. It’s totally different from standard shows.
Host: Tell our audience a bit about you.
Guest: My name is Kelly Kehn. I’m co-founder of Defy the Odds, with two business partners who are also well known in the space, Sue Schneider and Paris Smith.
[02:33] 5. Defy the Odds: a startup launchpad for inclusive entrepreneurship
Guest: This is our one-year anniversary this week, we launched at Lisbon last year. Defy the Odds is a startup launchpad focused on making entrepreneurship more inclusive, specifically to female founders and minority founders. We don’t see tons of founders who look different in our space right now. It’s not about capability, there are so many capable people across our industry, it’s about the invite, making sure they understand there are options if they have an idea or a business plan, and giving them the support and foundations they need. We do that through startup advisory, and we’re about to unveil an online community for startups, working to bring new money into the space so good ideas get funded and capital is readily accessible for those who need it.
[03:59] 6. Helping women and minority founders access funding and mentorship
Host: Are the barriers for women in this business visible?
Guest: I don’t know if there are barriers for women in particular. I think there’s a lack of an invitation. When you start your own business, it’s not just about knowing gaming and its revenue models, it’s about understanding the language of fundraising and speaking to investors. If no one’s given you that invite, or shown you who to speak to or what words to use, cap table, CAC, LTV, it’s a whole new language, and very uninviting. The first step is making sure everyone has those resources. The second is de-risking entrepreneurship. I spent the last seven or eight years working to get women into senior leadership and de-risking the C-suite for them. Seven years ago there were fears around it: how much time do I give up, is my reputation at risk, what if I can’t do it? Now women in the C-suite is commonplace, which is exciting. This is the next step: getting women to actually own their ideas and their business and benefit from that success.
[06:47] 7. Opening the industry to new ideas and perspectives
Guest: We’re at the right time in gaming. The US has gone through its regulation, more people and ideas are coming across, and at the same time we’re seeing big companies and consolidation. So how are we going to serve gaming with innovation going forward? We have to open it up. When we open the space to more people, perspectives and backgrounds, we all win, the pie gets bigger. We’re not shoving anyone out, we’re trying to get more ideas in. Across my business partners and me there’s 80 years of iGaming experience. We love it, we want to see it grow and be more globally accepted, and we want customers to think of it as part of their entertainment spend.
[08:05] 8. Crazy ideas that worked: cinematic live dealer and skill gaming
Host: What’s the one crazy idea that paid off wildly?
Guest: One that’s really impressing me, and it’s crazy because it’s not for my generation, is a startup doing Hollywood cinematic live-dealer with tie-ups to global media companies like Netflix and Universal. I don’t understand why I’d need an avatar or anime character as my dealer, but the younger generation is really into it, whether the game is video, social or real money. Those Hollywood motion-capture suits with all the sensors, it’s insane, and you think, we never thought of that in gaming before. We’re also working with a female founder of a studio called Thunder, whose background gives this magical outside perspective on gaming, and they understand blockchain and are building skill games. You can actively see these founders making their own luck. Skill games at a time when sweeps are under fire and US regulation makes it hard and expensive to get games to market, because skill games aren’t subject to some of that regulation. Lots of new operators want something innovative and easy to integrate, so it’s fun to watch that momentum.
[10:29] 9. What leaders forget when the numbers look good
Host: I remember your quote: if you can’t measure it, you can’t manage it. What does the owner stop noticing when the first numbers look good?
Guest: That quote should be attributed to Peter Drucker, the management author. I probably quoted him a couple of years ago when I was running the All-In Diversity Project, a nonprofit that gives gaming companies the same boardroom tools for their people that they have for every other topic. If you say you want diversity or inclusion, it has to be something the boardroom can take on board like digital transformation or managing risk, with benchmarking, data and research behind it. As for what leaders forget when the bottom line is black and things look good, which is worth celebrating, what often gets lost, especially in bigger companies, is the vision and culture of why you started this and who you started it with. Sometimes we hire fast because we’re scaling, and we forget the people we bring in to go faster are human. They contribute vast amounts beyond the bottom line, to your brand and to making it fun. That’s why we’re in this industry, so don’t lose sight of those people.
[13:47] 10. Champion’s rule: be kind to others and yourself
Host: What’s your top champion rule in business and life?
Guest: Be kind. Be kind to yourself and be kind to others. It’s a very small industry that we love, people move around, things happen, people succeed and people have bad eras of their life. At the end of the day it’s got to be fun, we’ve got to build relationships, and you never know what comes around. You also need to be kind to yourself, forgive yourself, and move on when things go wrong.
[14:37] 11. Feel the Beat: songs that inspire and motivate
Host: What song plays in your mind when you celebrate a big win?
Guest: I’m on a Beatles kick right now, so I’ll say “Ob-La-Di, Ob-La-Da.”
Host: And before a tough coaching session with your startups?
Guest: If I don’t know what to play, I go to Dolly Parton. I love Dolly Parton, probably “Jolene.”
Host: Jolene. And Miley Cyrus.
Guest: Dolly Parton is Miley Cyrus’s godmother. Did you know that?
Host: If one song described your whole career, what would it be?
Guest: An anthem in my life would be “This Is Me” from The Greatest Showman.
[16:16] 12. Why we need more bold, less “safe” startup ideas
Host: What was the most wishful, beyond-reality pitch you’ve seen?
Guest: To be fair, I’d like to see more crazy stuff. We see a lot of safe stuff, and a lot of founders who haven’t done their competitive analysis, which is really important. The opposite problem is people pitching me multiplayer blackjack, and I’m like, I’m pretty sure that’s existed for a long time, or multiplayer slots. So understand the landscape first, then get crazy. The genuinely crazy stuff is people who don’t want to work within the regulations while operating in a regulated market, and you’re like, you probably should.
Host: What’s your guidance for those crazy ideas?
Guest: If you’ve got a crazy idea and someone’s told you it’s crazy, don’t listen to them. If I tell you it’s crazy, don’t listen to me either. Go for it, if you really believe in it and understand how people would love that product. Getting a hundred “this is crazy” reactions is who changes the world. If you’re raising money, understand the person you’re talking to and their perspective, and it’s okay if you don’t agree. You’ll talk to 300, 400, 500 people and get a couple of yeses, that’s just how it works. Get those nos out, because every no puts you on the path to a yes. You learn what people care about and what their motivations are. Call me, actually, call me first.
[19:17] 13. Key metrics for startups: founder fit, MVP traction, paying users
Host: Which metrics give you an immediate signal a startup could be huge?
Guest: At the very early stage, when you’ve just got your idea and deck, we look at whether the founder is capable and has the experience to take the idea forward, whether they understand the competitive landscape and their addressable market. We see a lot of “it’s a gazillion-trillion market and we’ll get 20% of it,” and probably not, at least not this year. So we want a realistic understanding of the addressable market, the team or advisers to get there, and a clearly articulated problem and how you’ll solve it. At MVP stage, the KPI is real interest: do people want to use it? I honestly don’t care if you’ve won an award at a conference, that’s always in the deck, it’s good PR, but it’s really about signed contracts or people interested in working with you. Once you’ve got revenue, B2B or B2C, we want to see that they keep paying you and it’s growing. So it’s a staged approach; the KPI changes at every stage.
[22:07] 14. Network or Not Work
Host: A big sponsor offers a big cheque to a “minority” female founder, but still labels women a minority, as a bit of a power move.
Guest: If you want more female founders and you’re putting your energy there and just need a bit more education on the real situation, then network. If you’re trying to make yourself look like something you’re not, then not work.
Host: A founder comes to you for a grant and sponsorship but refuses mentorship.
Guest: Not work, and I’ll tell you why, and it’s not because I’m desperate to give my advice. A founder will be successful if they’re always open to learning. If you close yourself off from the very start, that’s a big red flag. We call it overconfidence, and we know where overconfidence leads.
Host: A startup that, in the name of diversity, picks the “inclusive” token candidate over the talent.
Guest: Not work. If you have no women on your board and you work in an industry or country where that’s required, and you can’t find one capable woman, the problem isn’t finding the women, the problem is you. In most civilised countries there are capable women to sit on a board. That’s just laziness.
[24:55] 15. Next big trends: women’s sport and regulatory tech
Host: Which area is about to explode that the industry underestimates? Give me the sexy one and the boring one.
Guest: The sexy part is women’s sport. Media is picking up on it, sponsorships are picking up on it, and any professional women’s game, whatever the sport, is great. The boring part is reg-tech, regulatory tech. So many jurisdictions everywhere are regulating now, and it’s hard to be compliant and build a team and a brand around. With the dawn of AI and new technologies that help on the regulatory side, those will be the companies that win. It’s boring but we need it, because the cost of not doing it is worse, and technology can remember more and act quicker than we can.
Host: Regulators themselves aren’t always equipped with enough people to issue licenses or run compliance checks, so this is going to be big too.
Guest: It’s not a sexy sell, but technology can eliminate a lot of our human mistakes, particularly in that sector.
[27:25] 16. Confession Lane: the scariest moment
Host: Halloween’s approaching. Was there anything in your career that scared you the most?
Guest: If you’re not scared, you’re probably not living up to your potential. The scariest thing for me was having my first child in 2015 and becoming a mother in a career. Before that, my whole life was my career, and it changes very quickly when you have a kid. Balancing what I was with who I was becoming, while saying the hard things out loud, like maybe I don’t want to work full-time, or maybe I need a break, when you have other people you need to keep alive, that’s really scary. What I learned is there are probably tons of women suffering because no one’s telling them to say the hard thing out loud, and no one’s there for them to say it to. That became my north star: to do that for women in our space. At a time when very few people were talking about supporting women into senior leadership, I had to say “I think we should do that, and we’ll all benefit, even the men.” Saying the thing when no one ever has is really scary, but it gets so much easier, and there’s so much respect and love on the other side.
Host: How did you like your ride?
Guest: So much fun. Thank you for inviting me, in a city I never get to drive around and look at, because we’re usually in the hotel or the conference. You’ve broadened my perspective. Thank you for your insightful questions and for caring about what we’re doing at Defy the Odds.
Host: The season has come to an end, but you bet we’ll keep driving iGaming forward. Until next time, stay great.
On the show
About the guest
Guest
Kelly Kehn
Co-Founder at Deffy the Odds
Kelly Kehn is the co-founder of the startup launchpad Defy the Odds and founder of the All-In Diversity Project, with two decades spent championing women and underrepresented founders in iGaming. She helps new founders access funding and mentorship, convinced that inclusion is less about capability than about the invite.
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