Startup Wins: Founders, VCs & Builders

Brandon Na
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Actionable Insights for Startups and Everyone in the Builder Ecosystem from Founders to VCs and Experts at building meaningful companies that track to become Unicorns and create multigenerational impact. Hosted by the former host of EduK8, Befm (Busan's English Radio) and the only SEO radio show on the internet in 2011. Brandon is also the author of UNICORN STARTUPS on Amazon.  https://amzn.to/47D9v1j Previous guests include VC & 8 Time Founder David Yi, Founder & Startup Expert Kevin Henrikson, 7 Time Founder Kimberly Kovacs, CMO Olga Denisova, LinkedIn Branding Expert String Nguyen, Micromarkets Expert & Payments Founder Mike King

  1. 2H AGO

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

    Send us Fan Mail  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 introHow deep tech VCs do due diligence on brand-new, unproven technologyWhy AI is compressing SaaS margins—and where the real defensibility is goingWhat LinkedIn spam is doing to founder outreach (and what actually works)Why Austin's emerging startup culture beats Silicon Valley's for builders right nowJohn'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 🔗 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 PodcastsStartup Wins on LinkedInStartup Wins on SpotifyHosted by Brandon Na, Managing General Partner of Good Peoples Ventures

    31 min

  2. SEASON 2, EPISODE 88 TRAILER

    Startup Wins Season 2 April 2026 Update

    Send us Fan Mail 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 PodcastsStartup Wins on LinkedInStartup Wins on SpotifyHosted by Brandon Na, Managing General Partner of Good Peoples Ventures

    3 min

  3. 4D AGO

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

    Send us Fan Mail 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 PodcastsStartup Wins on LinkedInStartup Wins on SpotifyHosted by Brandon Na, Managing General Partner of Good Peoples Ventures

    36 min

  4. MAR 1

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

    Send us Fan Mail 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 empireHow emailing 532 investors with almost nothing in the bank led to their first yes — and the exact email strategy that workedWhy Matthew believes fintech is the most important form of defense tech in the world right nowThe 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 systemWhy Miami might actually be a competitive advantage over Silicon ValleyMatthew's personal "happy routine" for staying mentally sharp when entrepreneurship gets brutalThis 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  🌐 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 PodcastsStartup Wins on LinkedInStartup Wins on SpotifyHosted by Brandon Na, Managing General Partner of Good Peoples Ventures

    50 min

  5. FEB 18

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

    Send us Fan Mail In this episode of Startup Wins, host Brandon Na sits down with his friend Bill Mastin, CEO of Cadient, 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 leadershipWhy startups demand resilience (and how to build it)The truth about product-market fitWhy SaaS is undergoing a massive transformationHow AI is changing hiring, recruiting, and workforce retentionWhy companies must now “fight AI with AI”What the future of microlearning and corporate training looks likeBill’s best advice to anyone building a company today🎧 New episodes of Startup Wins drop twice a month—subscribe and stay winning. Connect with Bill Mastin on LinkedIn Hosted by: Brandon Na Startup Wins on Apple PodcastsStartup Wins on LinkedInStartup Wins on SpotifyHosted by Brandon Na, Managing General Partner of Good Peoples Ventures

    48 min

  6. JAN 26

    4 Top Founders 14+ Startups, building UNICORNS, $200 mill exits, raising $100s of millions in startup capital, + $100 mill rev

    Send us Fan Mail A MUST watch Podcast:  Today's episode graces us all having 4 of the Top "Under the Radar" Founder Superstars in US history share:  how to build the "perfect" or imperfect team (Dan Shapiro, Kevin Henrikson)how to build 1 of the most important parts of startups: the cap table (Kim Kovacs)what are the keys to finding your perfect technical/engineering talent (Kevin Henrikson)secrets & creative ideas that could be worth thousands on the financing of your startups (Kim Kovacs)how do you figure out "tenacity", key trait for founding staff?  (Kevin Henrikson) what's the difference between a startup founder in terms of thinking (Alina Vandenberghe)what it's like to work with Steve Ballmer, Satya Nadella & Bill Gates (Kevin Henrikson)what it's like during the youth of a founder (Kim Kovacs) what it's like right before becoming a founder (Alina Vandenberghe) "Avenger" like Founders resumes:  Dan Shapiro, 4 Time Founder, Exited to Google for life changing money, $100 mill+ revenue w/ GlowforgeKim Kovacs, 7 Time Founder, raised more than $120 million, 3 successful exits OptionEase, MyJane, ORYXE Energy Kevin Henrikson, 2 Time Founder, 1 sold to Microsoft for $200 mill, Selling a company for 27x its total funding, Engineering Leader of Instacart++Alina Vandenberghe, Founder of a 1 time Unicorn, growing revenue to $50 mill ARR Subscribe & stay tuned to MANY MORE incredible startup founding advice like the aforementioned on Startup Wins hosted by Brandon Na coming up!     Startup Wins Host Brandon Na is Managing General Partner of Good People Ventures, former radio show host, and producer of the Edu-focused podcast EduK8, where he interviewed top VCs like Minnie Ingersoll (EduK8 S2 E12) and AI leaders like James Brady (EduK8 S3 E1). He is also the author of UNICORN STARTUPS, available now on Amazon. Memorable startup adages:  Dan: "Don't outsource your soul. Your first 10 hires are your company's DNA." Kim: "Watch your cash. Revenue is vanity, profit is sanity, but cash is reality." Kevin: "Ship today. Not tomorrow. Today." Alina: "Build for the world you want to see, not the world that currently exists." Startup Wins on Apple PodcastsStartup Wins on LinkedInStartup Wins on SpotifyHosted by Brandon Na, Managing General Partner of Good Peoples Ventures

    41 min

  7. JAN 19

    How Alina Vandenberghe Sold Her House to Build a $1B+ SaaS (Chili Piper)

    Send us Fan Mail The "Everything On The Line" Story of Chili Piper How do you go from selling your house and every personal possession to leading one of the most innovative companies in B2B SaaS? In this episode of Startup Wins, we sit down with Alina Vandenberghe, Co-Founder and Co-CEO of Chili Piper. Alina takes us behind the scenes of her radical journey—from her childhood in communist Romania to co-leading a near-unicorn startup with her husband. We dive deep into the "Chili Piper Way," exploring why they rejected traditional management hierarchies, how they pioneered a global remote-first culture across 40 countries, and the gritty reality of bootstrapping a company when you have no safety net. In this episode, you’ll learn: The Power of Radical Resilience: Why Alina’s upbringing in Romania gave her the "builder" mindset needed to survive the early days of bootstrapping.Company of the Future: How Chili Piper operates with a flat organizational structure and why they believe traditional managers are often unnecessary.High-Stakes Bootstrapping: The real story of selling their home to fund the company and why they stayed "all-in" despite the risks.Building Brand through Authenticity: How Alina used LinkedIn and personal branding to drive millions in revenue without a traditional ad spend.Remote Culture at Scale: Tactical advice on managing high-performing teams across dozens of time zones and cultures.Whether you’re a founder looking for scaling tactics or a leader interested in the future of work, Alina’s "no-nonsense" approach to business and life is a masterclass in execution. Startup Wins Host Brandon Na is Managing General Partner of Good People Ventures, former radio show host, and producer of the Edu-focused podcast EduK8, where he interviewed top VCs like Minnie Ingersoll (EduK8 S2 E12) and AI leaders like James Brady (EduK8 S3 E1). He is also the author of UNICORN STARTUPS, available now on Amazon. Alongside his MGP partner Vikki Meyer Fininen, Brandon entered the venture world and built Good People Ventures. Shortly before forming GPV, he launched Startup Wins to deliver actionable, real-world insights from startup founders, VCs, and world-class experts who are actively shaping the future. Startup Wins on Apple PodcastsStartup Wins on LinkedInStartup Wins on SpotifyHosted by Brandon Na, Managing General Partner of Good Peoples Ventures

    51 min

  8. JAN 5

    Product Is Everything: Building What Matters with 8 Bit Spark's Founders Liz Hunt & Michael Li

    Send us Fan Mail What if every business you touch is both a product and a service—and treating it that way unlocks the results you’ve been chasing? Startup Wins sat down with product veteran Liz Hunt & healthcare technologist Michael Lee, co-founders of 8 Bit Spark, to pull back the curtain on how real innovation happens inside messy constraints, heavy regulation, and shifting incentives. Startup Wins Host Brandon Na prompts Liz & Michael to unpack healthcare, founder fit, and a practical playbook for innovation from idea to impact along with:  • Market traction through relationships & narrative • Enshittification and incentive-driven platform decline • AI as data intake and the power of fine-tuning • Startup lessons: founder fit, selling first, vows • Healthcare incentives, capital misallocation, EMR risks If you’re serious about product-market fit, innovation under regulation, or deploying AI where it truly helps, this conversation will sharpen your approach and your decisions. Subscribe, share with a builder who needs it, and leave a review with the one change you’ll make this week. Brandon is Managing General Partner of Good People Ventures, former radio show host, and producer of the Edu-focused podcast EduK8, where he interviewed top VCs like Minnie Ingersoll (EduK8 S2 E12) and AI leaders like James Brady (EduK8 S3 E1). He is also the author of UNICORN STARTUPS, available now on Amazon. Alongside his MGP partner Vikki Meyer Fininen, Brandon entered the venture world and built Good People Ventures. Shortly before forming GPV, he launched Startup Wins to deliver actionable, real-world insights from startup founders, VCs, and world-class experts who are actively shaping the future. And if you want product experts to help you out with your startup, email Liz at liz@8bitspark.com or Michael at michael@8bitspark.com.  Startup Wins on Apple PodcastsStartup Wins on LinkedInStartup Wins on SpotifyHosted by Brandon Na, Managing General Partner of Good Peoples Ventures

    1h 8m
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Actionable Insights for Startups and Everyone in the Builder Ecosystem from Founders to VCs and Experts at building meaningful companies that track to become Unicorns and create multigenerational impact. Hosted by the former host of EduK8, Befm (Busan's English Radio) and the only SEO radio show on the internet in 2011. Brandon is also the author of UNICORN STARTUPS on Amazon.  https://amzn.to/47D9v1j Previous guests include VC & 8 Time Founder David Yi, Founder & Startup Expert Kevin Henrikson, 7 Time Founder Kimberly Kovacs, CMO Olga Denisova, LinkedIn Branding Expert String Nguyen, Micromarkets Expert & Payments Founder Mike King

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