Starting Up Again: The First 6 Months of Entrepreneurship

Entrepreneurship is like flying a plane in mid-air while it's on fire. As the plane descends, you repair a few critical parts. Gradually, it stops burning as fiercely. With more fixes, it starts to glide.

In the beginning, every problem feels existential:

• Should I add a co-founder?

• What industry should we target, and what product should we build?

• Can we raise money, or do we need to bootstrap?

• Can we afford to build the technology the world needs?

• How do we set compensation in a principled manner?

• Why are investors ghosting us after chasing us for years?

• What does our dream team look like, and how do we find and convince them to join?

These questions pop up daily, and you can't let them marinate for too long. They need action and, inevitably, failure. The worst thing you can do is let these questions linger in your head. The longer they stay, the less likely you are to act.

This inertia is why many people don't pursue entrepreneurship. It's not a lack of world-changing ideas but a hesitation to act quickly enough. Some start but don't see immediate success and quit. Entrepreneurship requires trying things and being comfortable with failure. It's easier said than done—failing repeatedly can be overwhelming and disheartening.

To break this cycle, build a reflection process to recognize achievements and celebrate failures. Our team sets three individual priorities each week and shares them. This reflection helps us learn from successes and bask in failures to glean lessons. Every month, we spend an hour celebrating these failures.

Tackling three things weekly, learning from successes and failures, and taking action are keys to success. This builds confidence that you can fix the plane and fly it to the moon.

Startups thrive on relentless momentum. Losing momentum can stall progress, demoralize the team, and erode belief in the dream. Momentum can come from small wins—an investor's note of confidence, an extended offer to a candidate, or a new AI model's release. Recognizing and sharing these wins and connecting them to the bigger picture is crucial in the early days. The CEO must generate and sustain momentum.

Six months after launching Sage, we've come a long way in answering existential questions. We've targeted healthcare with AI, closed a funding round with incredible early backers, gathered compensation data, and built an amazing team. We have designs, models in the cloud, and even an office with humanoid robots roaming 24/7. We've also added a co-founder, though we're not ready to share details yet.

To outsiders, it may all look easy and effortless.

I am reminded of Roger Federer’s recent commencement speech at Dartmouth. Federer, an eight-time Wimbledon champion, was known for his elegant game.

"People would say my play was effortless. Most of the time, they meant it as a compliment," he said. "But it used to frustrate me when they would say, 'He barely broke a sweat,' or, 'Is he even trying?'

"The truth is, I had to work very hard to make it look easy. I didn't get where I got on pure talent alone. I got there by trying to outwork my opponents. Most of the time, it's not about having a gift. It's about having grit."

Grit. Perseverance. Resilience. Onward and upward!