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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 Podcasts
• Startup Wins on LinkedIn
• Startup Wins on Spotify

Hosted by Brandon Na, Managing General Partner of Good Peoples Ventures

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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 Podcasts
• Startup Wins on LinkedIn
• Startup Wins on Spotify

Hosted by Brandon Na, Managing General Partner of Good Peoples Ventures

Send us a text

Xania Wong shares her 13 year journey founding 4 Startups that are not always about building a Unicorn. Read her LinkedIn profile and find she's won or final'd 16 different Startup competitions from the Chivas' the Venture Competition HK where we met [winner (2016)]to Google's Empowering Young Entrepreneur competition [winner (2014)].

Host Brandon Na explores the amazing journey she's had from Hong Kong to Instanbul and many other international destinations on the pursuit to help the world obtain affordable healthcare, secure work & provide businesses with their immediate labor needs.

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.

If you’re a founder, operator, or innovator looking for an edge, this episode with Shaun Gold is one you don’t want to miss.

Amazing guests include:

• Olga Denisova - ep 1
• Kevin Henrikson - ep 2
• String Nguyen - ep 3
• David Yi - ep 5
• Kimberly Kovacs - ep 6
• Mike King - ep 7
• Beth Massa - ep 8
• Dan Shapiro - ep 9 Pt 1 & Part 2
• Ellie Sarmadi - ep 10
• Shaun Gold - ep 11
• Startup Wins on Apple Podcasts
• Startup Wins on LinkedIn
• Startup Wins on Spotify

• Startup Wins on Apple Podcasts
• Startup Wins on LinkedIn
• Startup Wins on Spotify

Hosted by Brandon Na, Managing General Partner of Good Peoples Ventures