From a Snowstorm Pizza Run to $50M ARR: Matthew Vega-Sanz on Building Three Companies Before 30

Inside a VC’s Mind What Gets You Funded & What Kills Your Startup pt 2, John Forbes, Julian Capital

Send us Fan Mail [https://www.buzzsprout.com/2547291/fan_mail/new]  Startup Wins Podcast, Season 2, Ep 6, Part 2 of 2  The cold email is dead—or is it? In Part 2 of our conversation with John Forbes, Principal at Julian Capital and operator of Deep Checks, we go deeper into how VCs actually think, what's really happening to software in the age of AI, and why Austin might be the most underrated startup city in America.  Plus, John gets personal—sharing his heroes, his hard seasons, and the life philosophy that drives everything he builds.  💥 In this episode, you'll learn:  * Why a great cold email still beats every warm intro * How deep tech VCs do due diligence on brand-new, unproven technology * Why AI is compressing SaaS margins—and where the real defensibility is going * What LinkedIn spam is doing to founder outreach (and what actually works) * Why Austin's emerging startup culture beats Silicon Valley's for builders right now * John's personal hero (hint: it's a Founding Father) and what he borrows from him 🎧 Whether you're a founder trying to get your first VC meeting or an operator figuring out your next move, this episode is packed with actionable insight and rare candor from someone living it every day.   📩 Reach John directly: john@deepchecks.vc [john@deepchecks.vc] 🔗 Apply at Deep Checks: deepchecks.vc   🔔 Subscribe to Startup Wins for conversations with top VCs, founders, and operators shaping the future.   * Startup Wins on Apple Podcasts [https://podcasts.apple.com/us/podcast/startup-wins-founders-vcs-builders/id1846487087] * Startup Wins on LinkedIn [https://www.linkedin.com/company/startup-wins] * Startup Wins on Spotify [https://open.spotify.com/show/53rGFuX3m3Bg5B44iKJxLu] Hosted by Brandon Na [https://www.linkedin.com/in/brandonna/], Managing General Partner of Good Peoples Ventures [https://www.linkedin.com/company/good-peoples-ventures]

Startup Wins Season 2 April 2026 Update

Send us Fan Mail [https://www.buzzsprout.com/2547291/fan_mail/new] Hey Startup Wins family — and thank you, genuinely, for listening. If you've noticed we've gone quieter than usual, you're not wrong. And you deserve a real explanation, not a vague "we'll be back soon." This is my second serious podcast, and it's been one of the most rewarding creative journeys I've taken — full of unexpected highs, a few humbling lows, and conversations with founders who reminded me exactly why I do this work. But here's the honest truth: the work itself called me back in. A dear friend recently brought me into an incredible startup operating across 24 cities — and growing. The travel, the strategic support, the sheer energy of being in the trenches with founders again — it's the kind of opportunity I couldn't say no to. And as a one-person show here at Startup Wins, something had to give. So rather than pretend we're still on a bi-weekly schedule we can't sustain, I'm being straight with you: we're slowing the cadence intentionally. Fewer episodes, but every one will be worth your time. And speaking of worth your time — we have something great coming. Our next release is a 2-part conversation with John Forbes, Principal at Julian Capital and General Manager of Deep Checks — which he calls "the best place for deep tech founders to reach thesis-fit investors." It's a sharp, substantive conversation, and I think you're going to love it. Stay tuned. To every founder, future unicorn, and builder in this community — I'm sorry for the gap, and I'm grateful for your patience. This show exists because of you. If you have suggestions, founder introductions, or VCs and operators you think belong on this mic, please reach out. LinkedIn works, but the best way to get me is directly: brandon @ goodpeoplesventures.com. And if the show has meant something to you, a review or a subscribe goes a long way — not for vanity, but because knowing this lands somewhere real is what keeps me going. My only goal has ever been simple: add a few more smiles to the world, whatever form that takes. Sometimes it's this podcast. Sometimes it's a book on startups. Sometimes it's getting on a plane to help a founder figure out their next move. It's all the same mission. Happy days — as my partner would say. I'm Brandon Na. Thanks for listening to Startup Wins. * Startup Wins on Apple Podcasts [https://podcasts.apple.com/us/podcast/startup-wins-founders-vcs-builders/id1846487087] * Startup Wins on LinkedIn [https://www.linkedin.com/company/startup-wins] * Startup Wins on Spotify [https://open.spotify.com/show/53rGFuX3m3Bg5B44iKJxLu] Hosted by Brandon Na [https://www.linkedin.com/in/brandonna/], Managing General Partner of Good Peoples Ventures [https://www.linkedin.com/company/good-peoples-ventures]

How VCs Actually Think: Deep Tech, Founder Traits & the Truth About Venture Capital (John Forbes)

Send us Fan Mail [https://www.buzzsprout.com/2547291/fan_mail/new] Startup Wins Podcast, Season 2, Ep 6, Part 1 of 2  What do venture capitalists actually look for—and why do most founders get it wrong? In this episode of Startup Wins, host Brandon Na sits down with John Forbes, Principal at Julian Capital and the operator behind Deep Checks—the world’s largest deep tech funding platform. From building startups in high school to investing in cutting-edge hardware, climate, and AI infrastructure, John breaks down what separates founders who get funded from those who don’t. 💥 In this episode, you’ll learn: *The 5 traits top VCs look for in founders (and why most fail here) *What “market pull” really means—and why it matters more than your idea *The biggest mistakes founders make when pitching investors *Why deep tech (hardware, energy, robotics, AI infrastructure) is exploding *How Austin is emerging as a top startup + venture hub *Whether venture capital is actually “broken” (and the real truth behind it) John also shares real stories from the front lines—working inside a public safety platform startup, managing HR as Chief of Staff, and navigating the chaos every founder eventually faces. 🎧 Whether you’re a founder, investor, or operator, this episode gives you a rare inside look at how venture capital really works—and how to position yourself to win. 🔔 Subscribe to Startup Wins for more conversations with top VCs, founders, and operators shaping the future * Startup Wins on Apple Podcasts [https://podcasts.apple.com/us/podcast/startup-wins-founders-vcs-builders/id1846487087] * Startup Wins on LinkedIn [https://www.linkedin.com/company/startup-wins] * Startup Wins on Spotify [https://open.spotify.com/show/53rGFuX3m3Bg5B44iKJxLu] Hosted by Brandon Na [https://www.linkedin.com/in/brandonna/], Managing General Partner of Good Peoples Ventures [https://www.linkedin.com/company/good-peoples-ventures]

From a Snowstorm Pizza Run to $50M ARR: Matthew Vega-Sanz on Building Three Companies Before 30

Send us Fan Mail [https://www.buzzsprout.com/2547291/fan_mail/new] What happens when two Cuban-American brothers from a Miami farm get snowed in at college and can't get a decent pizza delivered? They build one of the largest car-sharing platforms in North America — and that's just the beginning. In this episode of Startup Wins, Brandon sits down with Matthew Vega-Sanz, the twin co-founder and CEO of Gail, the world's most advanced AI for financial services. Matthew's story is one of the most jaw-dropping founder journeys you'll hear: a Babson College dropout who launched a peer-to-peer car-sharing app that hit the top 100 in the App Store within 7 days, watched COVID kill it overnight, pivoted into insurtech, scaled that business to nearly $50M ARR, exited in 2024, and is now back building what he believes will be his generational company. What makes Matthew different isn't just the résumé — it's the mindset. A self-described average student with above-average work ethic, he'll tell you straight up that reading obsessively, dreaming irrationally big, and staying maniacally focused on the customer are the real reasons he's still standing while most startups aren't. In this conversation, we get into: * The snowstorm that accidentally launched a startup empire * How emailing 532 investors with almost nothing in the bank led to their first yes — and the exact email strategy that worked * Why Matthew believes fintech is the most important form of defense tech in the world right now * The one thing that keeps him up at night (hint: it's not competition) * Gail's bold vision — from Miami strip malls to powering financial services across the solar system * Why Miami might actually be a competitive advantage over Silicon Valley * Matthew's personal "happy routine" for staying mentally sharp when entrepreneurship gets brutal This episode is part founder playbook, part love letter to Miami, and part wake-up call for anyone sleeping on the future of AI in financial services. If you've ever wondered what relentless looks like in human form, meet Matthew Vega-Sanz. 🎙️ Connect with Matthew: LinkedIn [https://www.linkedin.com/in/matthew-vega-sanz/]  🌐 Learn more about Gail: meetgale.com Don't forget to subscribe, leave a review, and share this episode with someone who needs to hear that the only way out is through.  (Audio)  * Startup Wins on Apple Podcasts [https://podcasts.apple.com/us/podcast/startup-wins-founders-vcs-builders/id1846487087] * Startup Wins on LinkedIn [https://www.linkedin.com/company/startup-wins] * Startup Wins on Spotify [https://open.spotify.com/show/53rGFuX3m3Bg5B44iKJxLu] Hosted by Brandon Na [https://www.linkedin.com/in/brandonna/], Managing General Partner of Good Peoples Ventures [https://www.linkedin.com/company/good-peoples-ventures]

Cadient CEO Bill Mastin on Resilience, Hiring AI, and Building Through Constant Change

Send us Fan Mail [https://www.buzzsprout.com/2547291/fan_mail/new] In this episode of Startup Wins, host Brandon Na sits down with his friend Bill Mastin, CEO of Cadient [https://cadienttalent.com/], for a candid and fascinating conversation on startups, resilience, and how AI is transforming the future of business faster than most people realize. Bill shares his journey from early education technology work and corporate experience to building and leading high-growth software companies. Along the way, he breaks down what most founders learn the hard way: supply doesn’t create demand, product-market fit is everything, and the startup game is not for the faint of heart. The conversation takes a deep turn into the future of SaaS, hiring technology, and AI-driven recruiting, including how companies are now being forced to use AI to combat AI—especially as job applicants use tools to optimize resumes at scale. Bill also shares insights into Learn, a microlearning platform he helped build that’s been described as “TikTok for workforce training,” and explains why the future of learning is contextual, social, and powered by community-generated knowledge. If you're a founder, operator, investor, or just obsessed with where tech is headed, this is an episode you don’t want to miss. In this episode, we cover: * Bill’s path from education tech to startup leadership * Why startups demand resilience (and how to build it) * The truth about product-market fit * Why SaaS is undergoing a massive transformation * How AI is changing hiring, recruiting, and workforce retention * Why companies must now “fight AI with AI” * What the future of microlearning and corporate training looks like * Bill’s best advice to anyone building a company today 🎧 New episodes of Startup Wins [https://www.linkedin.com/company/startup-wins] drop twice a month—subscribe and stay winning. Connect with Bill Mastin on LinkedIn [https://www.linkedin.com/in/bmastin/] Hosted by: Brandon Na [https://www.linkedin.com/in/brandonna/] * Startup Wins on Apple Podcasts [https://podcasts.apple.com/us/podcast/startup-wins-founders-vcs-builders/id1846487087] * Startup Wins on LinkedIn [https://www.linkedin.com/company/startup-wins] * Startup Wins on Spotify [https://open.spotify.com/show/53rGFuX3m3Bg5B44iKJxLu] Hosted by Brandon Na [https://www.linkedin.com/in/brandonna/], Managing General Partner of Good Peoples Ventures [https://www.linkedin.com/company/good-peoples-ventures]