Most education founders think buyers want the perfect pitch, the flashy product, or the right political connection.

But Kevin Chavous—national education reformer, bestselling author, and President of Stride, Inc. proves that none of those close deals. What does? Credibility, proof, and persistence.

This episode is extra special because Kevin was the very first guest we ever sat down with when we launched Breaking the Grade back on April 1, 2022. And his message then is even more relevant today for education founders, EdTech companies, and leaders chasing traction in a shifting market.

From losing a mayoral race in D.C., to leading one of the most influential school reform movements in the country, to shaping hybrid learning for millions—Kevin’s story is more than inspiration. It’s a blueprint for how to earn credibility, attract trust, and turn setbacks into traction.

Because here’s the truth: wins show your solution works, and setbacks—if you frame them right—make buyers trust you even more.

In this episode of Breaking the Grade, I sit down with Kevin Chavous and my co-host John Gamba, Director of Innovative Programs and Entrepreneur-in-Residence at Penn GSE, to unpack the journey behind Kevin’s impact—and why it matters for every founder chasing traction in the education market.

This isn’t just an interview. It’s a founder playbook for turning obstacles into assets, building buy-in that accelerates deals, and creating solutions that students and teachers actually champion.

🔑 5 Big Takeaways for Education Founders

1️⃣ Credibility Comes From the Hard Parts
Kevin’s wake-up call came in a prison where a warden said educating inmates was a “waste of money.” That story became his credibility anchor. For founders, your toughest moments are your most powerful proof points—buyers trust scars, not slogans.

2️⃣ Setbacks Sell—If You Frame Them Right
Kevin’s failed mayoral run didn’t end his influence—it multiplied it. By framing setbacks as fuel, not failure, he turned doubt into trust. Founders who position setbacks as lessons, not failures, win more trust with buyers and partners.

3️⃣ Student Voices = Buyer Signals
“The most dangerous phrase is, ‘We’ve always done it this way.’” Kevin shows why aligning with student needs is the ultimate credibility test for founders.

4️⃣ Community Buy-In Is the Real Multiplier
D.C.’s reform worked because it was built with community voices, not imposed on them. For founders, the same principle accelerates sales: champions in your market generate warmer, faster-moving leads than cold calls ever will.

5️⃣ The One Yardstick That Closes Deals
Kevin’s mantra: “Will this help a child learn?” If you can answer that clearly and back it with evidence, you’ve already handled the biggest objection in the sales process. If not, your pitch stalls.

If you’re still treating setbacks as failures, this episode is your reset. Kevin proves they’re your strongest growth story—and that the first guest we ever hosted on Breaking the Grade back in April 2022 still has the blueprint founders need most today.

📩 DM me “Journey” and I’ll show you how to structure your setbacks into proof points that attract buyers, partners, and investors.

📤 Know a founder struggling to turn challenges into momentum?
Send them this episode—it might save them from quitting too early.

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