Breaking the Grade
Breaking the Grade is a thought-provoking podcast that follows entrepreneurs in the education space as they make their way to the top. Tune in for stories about breaking norms, introducing new ideas, and shaping our future society through every lesson let out.
Episodes
88 episodes
Best of 2025: Jolene Levine on How Education Founders Can Turn Betrayal, Burnout, and Chaos Into a Blueprint for Credibility, Alignment, and Lead Flow That Converts
Some episodes don’t just start conversations, they shift how education founders think about credibility, leadership, and lead generation. This one did.When Jolene Levin,...
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50:13
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Best of 2025: John Gamba on How Education Founders Can Rebuild Trust, Visibility, and Pipeline Through Authentic LinkedIn Strategy
Some episodes don’t just offer sales tactics; they redefine how education founders think about visibility, trust, and lead flow. This one did.When John Gamba joined Josh for a ca...
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49:15
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The Gratitude Episode: 22 Guests, 63 Countries, and a Community That Turned 2025 Into Our Most Meaningful Year Yet
Most founders rush to the next metric, the next meeting, the next milestone.But the truth is: you can’t scale what you don’t stop to appreciate.This episode is different.It’s the last show of 2025.It’s the Thanksgiv...
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20:16
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The Headline Mistake: How eight words on LinkedIn unlocked a $100k repeatable pipeline.
Most education founders think their LinkedIn headline is just a formality.A place to drop their title. List their company. Maybe add “passionate about education.”But here’s what they’re missing: your headline is where credibility ...
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15:12
Hesitation Is a $250K Mistake: Dr. Tamara Minott on How Education Founders Close Deals With Confidence
Most education founders don’t lose deals because their product isn’t good enough.They lose them because they hesitate, overthinking the pitch, second-guessing decisions, and waiting for “perfect” when progress is all they need.Tha...
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26:42
You Crushed the Demo—But Still Can’t Close: The $100K Mistake Education Founders Keep Making
You crushed the demo.The buyer smiled. They nodded. They even said, “This is exactly what we need.”And then… nothing.That silence isn’t harmless. Every “We’ll be in touch” costs you weeks of follow-up, lost momentum, and...
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18:58
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From Betrayal and Courtroom Battles to Closed Deals: Robespierre Reyes on Rebuilding Credibility, Team Alignment, and Education Deals That Close
Robespierre Reyes had funding, traction, and a winning idea.Then came the lawsuits, burnout, and partners who betrayed him.Four companies, three failures, one courtroom ...
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19:05
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From Confusion to Clarity: JD Mosley-Matchett on the Message Shift That Turns Unclear Offers into Scalable, Trust-Building Growth for Education Founders
Most education founders and EdTech leaders think their problem is marketing.But sometimes, the real issue is something more critical: ClarityIf your message isn’t clear, your market stops listening, no matter how brilliant your so...
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18:36
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The Mindset Reset: Mitch Weisburgh On How Education Founders Can Master Mindset, Beat Burnout, and Close Strong Deals
You’ve got the product, the drive, and the skills, but when pressure hits, your mindset starts to crack.Suddenly, deals stall, momentum fades, and even your warmest prospects go quiet. The harder you push, the less it seems to move forwa...
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36:54
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Stop Delegating Sales: Why Education Founders Must Sell Their Solution First Or Watch Their Pipeline Die
Most education founders think the next rep, agency, or AI tool will solve their sales problem. It won’t.Here’s the truth: if you can’t sell your own offer clearly, no one else can. Every lead you hand off too early...
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14:05
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From Lost Leads to Locked Contracts: Paul King on Niche Focus, Pilots That Convert, and Closing Education Deals
What happens when you stop trying to serve every school and start solving one urgent problem for the right schools?It’s the positioning shift most founders resist—but it’s the exact move that transforms “just another vendor” into a missi...
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32:38
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The Education Founder’s Blueprint: Kevin Chavous on Turning Setbacks Into Proof Points, Credibility, and Growth That Lasts
Most education founders think buyers want the perfect pitch, the flashy product, or the right political connection.But Kevin Chavous—national education reformer...
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47:41
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The Guarantee Shift: Karim Kuperhause on How Education Founders Build Trust and Win Qualified Leads Without Sounding Desperate
What happens when a superintendent or a higher ed leader—looks you in the eye and asks: “What happens if this doesn’t work?”For most education founders, that’s the deal-killer moment. They freeze. They dodge....
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44:59
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From Invisible to Irresistible: Michael Campbell on Using Research and Proof to Build Trust, Generate Leads, and Drive Education Growth
Every education founder, EdTech CEO, and school leader wants growth. But here’s the mistake almost everyone makes: they chase revenue before they’ve earned trust.In education, trust is the real currency—it turns a pitch into a meeting, a...
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28:31
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$9M Raised, Zero Guesswork: How YourWay Raised $9M by Solving the Lead Gen Problem Most Education Founders Ignore
Most education founders don’t fail because of bad ideas.They fail because they lean too hard on “AI-powered” buzzwords, skip the research-to-practice proof buyers demand, and don’t form the partnerships that give them credibility and att...
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27:14
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From “Great Pitch” to Signed Contract: Paul Vallas on the Buyer’s Lens That Closes Education Deals
What happens when you finally land the big meeting… and walk out with nothing but “We’ll think about it”?It’s the growth killer most founders don’t see coming—your pitch isn’t aligned with how education buyers actually make decisions.
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23:56
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(Re-Air) The Signature Solution: Your Proven Blueprint to a Clear Offer That Generates Leads and Wins the Education Market
What if your biggest lead gen problem isn’t visibility — but the fact that your offer isn’t clear enough to close?Most EdTech founders think they have a marketing problem.Some think it’s a sales problem.But what they actual...
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17:08
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From $10M in Sales to Losing Her Company: What Education Founders Learn the Hard Way About Selling, Scaling, and Staying Aligned
Most founders think their growth problem is sales.But Jolene Levin, entrepreneur, innovator and founder of No...
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26:12
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(Best of) Your Demo Is the Problem: What Education Founders Must Do—and Stop Doing—to Close More Deals With Their Demos
Most EdTech demos fall flat because they focus on product—not pain. They walk through features—but skip the funding strategy.They sound polished—but feel disconnected.And when the call ends? No buy-in. No follow-up. No...
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35:20
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From Collapse to Credibility: Robert Martellacci’s Blueprint to Win Back Influence and Close Deals in the Education Space
What happens when your billion-dollar success story ends—and the market forgets your name?Robert Martellacci knows. And he didn’t quit—he reinvented.This episode isn’t just about resilience.It’s about the bold mindset shift it ta...
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33:37
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From Dead-End to C-Suite: An Edtech’s Messaging Framework That Converts Education Conversations into Contracts
Here's the Messaging Fix You Didn’t Know You NeededIf your EdTech offer sounds “nice” but never gets past your perfect client to respond… this episode is your wake-up call.Carlos ...
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15:33
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Your Summer Fix: How Education Founders Can Rebuild Lead Flow Before Back-to-School
Let’s get one thing straight:September doesn’t start in September. It starts now—in June, July, and August.Because the biggest mistake founders make in summer isn’t taking a break.It’s confusing rest with silence.
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14:38
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From Quiet Posts to Real Revenue: How Anissa Used LinkedIn to Build Trust and Attract Qualified Leads
Most EdTech founders are still chasing views.Anissa Bouderraoui is closing pilots.She didn’t wait to go viral.She showed up consistent...
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41:07
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The Rest Advantage: How Education Founders Use Strategic Pauses to Spark Lead Gen Breakthroughs
Most education founders treat traction like a treadmill.When the leads slow down, they don’t stop to ask why—they sprint faster.More posts. More emails. More calls. More grind.But here’s what most founders miss:📉 Mot...
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14:31
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Clearer Messaging, Consistent Leads: What EdTech Founders Can Learn from MindShifting
Most education companies don’t lose leads because their product is weak.They lose them because the message doesn’t land.They try to sound professional. Strategic. Smart.But polish ≠ presence.And clever ≠ clear.In this ...
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36:11
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