Why would I give up? with Alina Vandenberghe episode artwork

EPISODE · Apr 14, 2026 · 22 MIN

Why would I give up? with Alina Vandenberghe

from Actually, I Can. · host Lindsay Tjepkema

Alina Vandenberghe gets asked constantly: "Why don't you seek an exit?" In CEO communities, at events, from advisors, the assumption is always that a $3 billion exit is the ultimate goal every founder should pursue. She's been building Chili Piper for a decade. She's not selling.What you'll learn:Why the standard exit advice completely misses the point for values-driven foundersHow Alina transformed from someone who "didn't comprehend human connection" to organizing intentional dinners and building real relationshipsThe daily pressure founders face (and the one thought that keeps Alina going when the arrows come flying)Why proving capitalism can look different became her actual mission - not the exit fantasyHow to withstand relentless pressure when you're building something that doesn't fit anyone else's playbookAbout Alina VandenbergheAlina Vandenberghe is the co-founder and co-CEO of Chili Piper, a company helping marketing teams and GTM ops people get more pipeline with agents. She started the company to create an environment where she and her husband could thrive, solving complex puzzles with fun people, remotely, with joy and compassion. Before Chili Piper, she climbed from intern to SVP at publicly traded companies across FinTech, healthcare, and education. She made a lot of money. She was very unhappy. Now she's building her own definition of success.This episode is a masterclass in what happens when you have the audacity to reject everyone's advice and discover your own path - and why the courage to simply be yourself might be the most important work you do as an adult.TIMESTAMPS[0:00] The Bad Advice[0:35] Who Alina Is and How Chili Piper Started[2:46] "The Most Important Thing We Do Is Have the Courage to Be Ourselves"[14:35] The Relationships Revelation: The Communication Course That Changed Everything[17:37] Why Exits Are Tempting (And Why She Says No Anyway)[18:13] "If You Can't Do It, There's No One Else Who Can Do It"[19:24] Advice for Founders Feeling the Pull📩 Subscribe to the newsletter: lindsaytjepkema.substack.com 🔗 Follow Lindsay on LinkedIn🔗 Follow Alina on LinkedIn🌶️ Learn more about Chili Piper: chilipiper.com

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Alina Vandenberghe gets asked constantly: "Why don't you seek an exit?" In CEO communities, at events, from advisors, the assumption is always that a $3 billion exit is the ultimate goal every founder should pursue. She's been building Chili Piper for a decade. She's not selling. What you'll learn: Why the standard exit advice completely misses the point for values-driven foundersHow Alina transformed from someone who "didn't comprehend human connection" to organizing intentional dinners and ...

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Why would I give up? with Alina Vandenberghe

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