🚀 10 Lessons I’ve Learned From Watching Founders Pivot

Hey Founders,

The founder journey is rarely a straight line. It’s full of twists, turns, and—at some point—a pivot.

I’ve worked with countless early-stage founders, and I’ve seen pivots that saved companies… and others that came too late. The best pivots aren’t about giving up—they’re about unlocking new growth.

Here are 10 lessons I’ve learned from watching founders pivot successfully (and unsuccessfully). 👇

1️⃣ Pivots Aren’t Failures—They’re Strategy

The best founders don’t see pivots as quitting. They recognize that adapting is part of the process. Airbnb, Slack, and Instagram all pivoted before they found success.

🔥 Takeaway: The faster you embrace change, the stronger your company becomes.

2️⃣ Data (Not Emotions) Should Drive Your Pivot

Too often, founders wait too long to pivot because they’re emotionally attached to their original idea.

📉 Look at the data:
✅ Are customers actually paying?
✅ Are investors hesitant because of traction?
✅ Is revenue growth stalling?

🚀 Pivot when the numbers—not your ego—say it’s time.

3️⃣ Pivot Small Before Pivoting Big

Not every pivot has to be massive. Sometimes, a small shift in pricing, audience, or positioning can make all the difference.

🔄 Test small changes before you throw out your whole business model.

4️⃣ Customers Will Tell You What They Actually Want

Founders who listen closely to customers often pivot toward something better.

🗣️ If people keep asking for something you didn’t originally plan to offer, pay attention.

💡 Slack started as a gaming company. Their internal messaging tool became the real opportunity.

5️⃣ Your Team Needs to Be on Board

A pivot is an all-hands-on-deck moment. If your team doesn’t believe in the new direction, execution will suffer.

🛠️ Over-communicate the "why" behind the pivot and make sure your team is aligned.

6️⃣ Some Investors Will Lose Confidence—And That’s Okay

When you pivot, some early supporters may not be thrilled.

💡 But here’s the truth: Great investors bet on teams, not just ideas.

🚀 The right investors will stick with you if you can articulate the opportunity ahead.

7️⃣ Speed Matters—But So Does Thoughtfulness

I’ve seen pivots happen in a weekend and some take six months—both have worked.

🏎️ Speed is important, but clarity matters more. A rushed pivot without a plan is just panic.

8️⃣ The Best Pivots Aren’t Just Defensive—They’re Opportunistic

Most founders pivot because something isn’t working, but the best pivots happen when they spot an untapped market and move fast.

👀 Stay alert—sometimes a pivot isn’t about fixing a problem. It’s about seizing an opportunity.

9️⃣ If You Have to Pivot Again, Do It

I’ve watched founders pivot twice, even three times before hitting product-market fit.

🔁 If the first pivot isn’t right, refine and pivot again. Some of the best companies took multiple attempts before they found their winning formula.

🔟 The Strongest Founders Reinvent Themselves Too

A pivot isn’t just about changing the business—it often means evolving as a leader.

💡 Founders who succeed through pivots are:
✅ Adaptable
✅ Self-aware
✅ Open to rethinking what they thought they knew

🔥 Final Thoughts

Pivots aren’t easy, but they’re often necessary. The best founders know when to shift, how to listen to the market, and how to bring their team along for the ride.

💡 If you’re considering a pivot, don’t panic—just make sure it’s driven by insight, not desperation.

Have you been through a pivot? What’s the biggest lesson you learned? Drop a reply—I’d love to hear your story!

Until next time—keep building!

Cheers,
Steve Walsh
Founder, Hands On Angel

P.S. Want actionable strategies to ace your next investor meeting? Join The Funding Accelerator and take control of your fundraising journey! 🚀