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Breaking the Grade

Josh Chernikoff

83 episodes

6 days ago

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 deals that should already be on your books. In Part 1, “Your Demo Is the Problem” with John Gamba, Entrepreneur in Residence and Director of Innovative Programs at Penn GSE, Josh and John exposed a hard truth: most EdTech demos fail before they even start. Founders pitch p...

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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 deals that should already be on your books. In Part 1, “Your Demo Is the Problem” with John Gamba, Entrepreneur in Residence and Director of Innovative Programs at Penn GSE, Josh and John exposed a hard truth: most EdTech demos fail before they even start. Founders pitch p...

Show more...

Episodes (20/83)

Breaking the Grade

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 deals that should already be on your books. In Part 1, “Your Demo Is the Problem” with John Gamba, Entrepreneur in Residence and Director of Innovative Programs at Penn GSE, Josh and John exposed a hard truth: most EdTech demos fail before they even start. Founders pitch p...

6 days ago

18 minutes

Breaking the Grade

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 showdown. His confidence, credibility, and pipeline of leads were all at risk. Most founders would quit. Rob didn’t. Instead, he rebuilt everything that actually drives qualified leads and closed deals, team alignment, credibility, and trust, with radical honesty, clear boundaries, and a repeatable playbook for education fou...

1 week ago

19 minutes

Breaking the Grade

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: Clarity If your message isn’t clear, your market stops listening, no matter how brilliant your solution is. That was the hard truth JD Mosley-Matchett had to face. As the Founder & CEO of InforMaven.AI, JD’s mission was bold: help underfunded, overregulated colleges and universities harness the power of AI to operate more efficiently. But even her biggest ...

2 weeks ago

18 minutes

Breaking the Grade

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 forward. Most education founders panic. They double down on demos, CRMs, late nights, and new pitches, thinking more effort will fix it. 🚫 Big mistake. When your mindset cracks, hesitation costs contracts, fatigue kills momentum, and fear turns every objection int...

3 weeks ago

36 minutes

Breaking the Grade

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 is wasted time, lost money, and a pipeline headed for collapse. Every day you delay founder-led sales is another day your growth stalls and another day your competition pulls ahead. In this episode of Breaking the Grade, you’ll hear the reset education founders don’t want but desp...

1 month ago

14 minutes

Breaking the Grade

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 mission-critical partner. That’s why this episode of Breaking the Grade is essential listening: Josh sits down with Paul King—Founder & Director of Neighborhood Educational Partners (NEP) and Founder of King Education, who pivoted from one-on-one tutoring to l...

1 month ago

32 minutes

Breaking the Grade

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, 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 toda...

1 month ago

47 minutes

Breaking the Grade

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. They hide behind buzzwords. And the buyer walks away unconvinced. But here’s the truth: In today’s market, whether it’s K–12 districts or higher ed institutions, leaders don’t buy hope—they buy guarantees. That’s why this episode of Breaking the Grade could be one of the m...

1 month ago

44 minutes

Breaking the Grade

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, and a meeting into a deal. In this episode, I’m joined by Michael Campbell, president of Advancing Global EDU, Inc., Chief Executive Officer of Dual Bridges Academy and Advisory Board Member at edWeb.net, LIVE from the ASU-GSV Summit (the edtech conference eac...

2 months ago

28 minutes

Breaking the Grade

$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 attract the right leads. That’s the cycle YourWay Learning set out to break. Back in January, at the IFE Conference in Monterrey, Mexico, I sat down with Jaime Palés, co-founder and president of Yourway Learning, with 20+ years of global experience scaling educa...

2 months ago

27 minutes

Breaking the Grade

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. That’s why this live Breaking the Grade episode from ASU-GSV (the edtech conference each April in sunny San Diego) is such a win: I sat down with Paul Vallas——nationally recognized education leader, former superintendent of Chicago, Philadelphia, and New Orlean...

2 months ago

23 minutes

Breaking the Grade

(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 actually have is this: ❌ An offer that’s vague ❌ A proven model that’s undefined ❌ And no document that makes buyers say “yes” on the spot We first aired this episode on March 4, 2024 — and the response was so strong, we’re bringing it back. Because the Signature Solution isn’...

2 months ago

17 minutes

Breaking the Grade

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 NorvaNivel proved it’s the other way around: your sales reveal your growth problem. Jolene founded a classroom furniture company in Australia, scaled it across schools, and then brought it to the U.S. Three months after launching in the U.S., she closed $10M in deals. No sales team. No systems. No safety net. Just conviction, urgency—and operational chaos catching up fast. And two years...

3 months ago

26 minutes

Breaking the Grade

(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 deal. That’s where John Gamba changes the game. John isn’t just an expert in EdTech innovation—he’s coached thousands of education entrepreneurs through founder-led sales. As Director of Innovative Programs and Entrepreneur-in-Residence at Penn GSE, he’s helped founders...

3 months ago

35 minutes

Breaking the Grade

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 takes to reclaim relevance, rebuild trust, and restart traction when everything you built gets wiped off the board. Robert Martellacci—founder of MindShare Learning—joins me LIVE from the Education Research & Development Institute (ERDI), one of the most influent...

3 months ago

33 minutes

Breaking the Grade

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 Needed If your EdTech offer sounds “nice” but never gets past your perfect client to respond… this episode is your wake-up call. Carlos Zapata, founder of Unicorn Academy, joins me live from the IFE Conference in Monterrey, Mexico — and pulls back the curtain on the exact moment his company stopped stalling and started closing. And here’s the kicker: it wasn’t the product that changed. It was the pitch. Carlos went from selling English upskilling a...

3 months ago

15 minutes

Breaking the Grade

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. You can recharge and still generate leads. But most EdTech founders go dark. They hunker down. Rebuild ops. Tweak product. And completely disappear from LinkedIn. Then they roll into Q4 hoping “back to school” will bring the momentum. Spoiler: It won’t. In this episode of Breakin...

3 months ago

14 minutes

Breaking the Grade

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 consistently—with clarity, credibility, and the kind of messaging school leaders actually respond to. The result? No gimmicks. No funnels. Just a pipeline built on trust. Bolstered by LinkedIn consistency. 🎯 When Anissa started posting on LinkedIn, she wasn’t playing the influencer game. She was speaking directly to curriculum directors, bilingual program leads,...

4 months ago

41 minutes

Breaking the Grade

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: 📉 Motion ≠ Momentum 📉 Hustle ≠ Clarity 📉 Activity ≠ Conversion In this episode, Josh goes solo to unpack a hidden truth in EdTech sales: Your burnout might be bottlenecking your lead gen. He shares a real story from inside the EdSales Elevation Experience—Ken Spiegel, founder of Lo...

4 months ago

14 minutes

Breaking the Grade

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 episode, Josh sits down with Mitch Weisburgh—a lifelong educator, EdTech veteran, and founder of MindShifting with Mitch—to unpack what really happens when education founders try to grow… without adjusting their communication to match their audience’s mindset. Mitch isn’t j...

4 months ago

36 minutes