EP222: The Entrepreneur’s Roller Coaster: How to Stay Steady Through the Highs and Lows

Entrepreneurship is rarely a smooth ride. One day can bring momentum, validation, and growth; the next can bring rejection, financial pressure, or a problem that threatens to derail everything. In this conversation, Colin C. Campbell and Michael Gilmore explore the emotional reality of building a business through the lens of “the entrepreneur’s roller coaster.”

The discussion covers how founders can better manage the shocks that come with running a company, from broken deals and changing market conditions to team pressure, family stress, and personal burnout. Michael shares practical ways he protects his mental clarity, including setting firm weekend boundaries, taking periodic solo planning retreats, and finding trusted people outside the family to serve as a pressure-release valve.

Second-Time Founders: Repeat Is the Hardest Word

Six weeks after the wire hits, most founders feel nothing at all. Not relief. Not triumph. Nothing. That's the part of the exit nobody warns...

How to Scale a Startup: What Actually Breaks

Most companies don't die from lack of demand. They die from getting it. How to scale a startup is really one question: what happens when...

Focus on Something You and Others Love: A Founder’s Framework for the AI Era

Adapted for an AI world from Chapter 4 of Colin C. Campbell’s Start. Scale. Exit. Repeat. In 1993, I made a decision that looked questionable...

Global Startup Funding Has a Passport Now

Founders built 43.6% of the world's new billion-dollar companies outside the United States this year. You don't have to move anymore. Global startup funding...

Record Startup Funding Is Not a Strategy

Venture capital just set a record, and almost none of it is coming to you. July 2026 delivered $65 billion in record startup funding. Double...

Catch the Next Wave: Why AI Timing Matters More Than Ever

Part of Startup Club's ongoing series exploring Colin C. Campbell's Start. Scale. Exit. Repeat.—reimagined for the AI era. This post is adapted from Chapter...