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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.

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