Build, Scale, Exit, Repeat: The Real Story Behind Earning It | Riggs Kubiak | #49

Everyone celebrates the exit. Nobody talks about what it costs you to get there. Riggs Kubiak built and sold a $50M construction tech company, and he's here to tell you what the highlight reel left out.

In this episode of I Can Fit That In, Erin sits down with Riggs Kubiak, entrepreneur, investor, and author of the new book Earned, a raw behind-the-scenes look at what it actually takes to build something meaningful. Riggs founded Honest Buildings, scaled it to 120 employees, raised over $50 million in venture capital, and sold it to Procore, which later went public on the New York Stock Exchange. This conversation isn't a success story in the traditional sense. Erin and Riggs dig into the emotional realities of entrepreneurship, the burnout, the self-doubt, the identity questions that most founders are too afraid to say out loud. If you're building something, leading a team, or standing at the edge of a big leap, this one is for you.

What You'll Take Away

Why you can't outwork your way through every stage of building a business, and what actually moves the needle when hard work alone isn't enough

How to recognize when your drive to perform is crossing into burnout territory, even when you think you're fine

Why the inner critic shows up loudest at the highest levels, and how naming it changes your relationship with it

What Riggs wishes he'd known about protecting his identity, relationships, and wellbeing while scaling a company

How vulnerability in leadership isn't weakness. It's the thing that gives other people permission to be honest too

More About Riggs

Riggs Kubiak is the founder of Honest Buildings, acquired by Procore Technologies, and the author of Earned, a founder's guide to the stages, mistakes, and real growth that entrepreneurship demands. He now invests in and advises early-stage founders.

If this episode resonated, subscribe so you never miss a conversation that goes beyond the surface. And if you know a founder, leader, or professional who needs to hear this, share it with them.

Connect with Riggs:

💼 Linkedin: RiggsKubiak

Twitter: riggskubiak

Connect with Erin Coupe:

💫 Instagram: @authenticallyec

💼 LinkedIn: Erin Coupe

🌐 Website: ErinCoupe.com

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