How to Run Through Startup Challenges

The Moment When Your Heart Is Pounding (And Why It Means You're On the Right Track)

Every entrepreneur has been there. That moment when your heart is racing, doubt creeps in, and you wonder if you have what it takes to keep going. As a founder—and a (sometimes reluctant) runner—I know that feeling all too well.

Years ago, after a long break from running, I decided to get back into it. Not even a kilometer in, my heart was pounding, my lungs were burning, and I thought, “I’m completely out of shape.” But I kept at it, trained consistently, and pushed through the discomfort. And here’s the thing—even now, after years of running, that feeling still hits me in the first couple of kilometers. The difference? I expect it. I know that if I push through, my breathing will settle, my body will adjust, and I’ll find my rhythm.

Startups work the same way. Every founder faces moments that feel impossible. The difference between a first-time entrepreneur and a seasoned one isn’t avoiding challenges—it’s knowing those challenges are temporary, pushing through, and finding your stride.

Experience: The Ultimate Endurance Trainer

I learned this the hard way when the dot-com bubble burst and nearly took my first startup with it. Clients disappeared, budgets dried up, and raising capital became nearly impossible. It felt like the world was caving in. But instead of throwing in the towel, we looked for other opportunities—and found unexpected traction in Japan, where the economy was more stable. That experience was brutal, but it shaped how I approach challenges. Later, when other ventures hit rough patches, I had the resilience and confidence to navigate them, knowing persistence and adaptability always win.

Take Stewart Butterfield, the founder of Slack. Before Slack revolutionized workplace communication, he was building a gaming company that ultimately failed. But instead of walking away, he saw potential in an internal communication tool they had built and pivoted. That experience—the failure—helped him recognize an opportunity others might have missed.

Building Your Entrepreneurial Endurance: A Guide for First-Time Founders

You can’t shortcut experience, but you can prepare for those gut-check moments by learning from others and building mental resilience. Here’s how:

• Surround Yourself with Experience: Find investors and serial entrepreneurs who’ve been through tough times. Their insights can help you avoid mistakes and keep perspective.
• Hire Leaders Who’ve Weathered Storms: A great executive isn’t just someone with big wins—it’s someone who has battled through setbacks and come out stronger.
• Study the Journeys of Successful Founders: Don’t just focus on their wins. Understand the struggles they faced and how they overcame them.
• Trust Yourself and Your Team: When pressure builds, lean on your co-founders, key team members, and advisors for support and encouragement. Build a culture where problems are tackled together, not in isolation.

The grind is inevitable. That early-stage chaos, the uncertainty, the stress—it’s like the burning in your lungs at the start of a run. But if you expect it, embrace it, and keep pushing forward, you’ll break through.

So, the next time your heart is pounding and it feels like everything is falling apart—remember, this is part of the process, embrace the challenge, and keep running.