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Breaking the Grade
Josh Chernikoff
91 episodes
4 days ago
Some episodes don’t just inspire, they show you what execution really looks like. This one’s a real-time playbook in action. Originally LIVE from the University of Toronto at the Canadian EdTech Summit on 30th October, 2025, Josh breaks down exactly how education founders can stop wasting time and money at conferences, and start turning them into revenue-driving machines. After two decades in education and sales leadership, Josh has learned one thing: conferences don’t grow your business, a c...
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Education
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All content for Breaking the Grade is the property of Josh Chernikoff and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Some episodes don’t just inspire, they show you what execution really looks like. This one’s a real-time playbook in action. Originally LIVE from the University of Toronto at the Canadian EdTech Summit on 30th October, 2025, Josh breaks down exactly how education founders can stop wasting time and money at conferences, and start turning them into revenue-driving machines. After two decades in education and sales leadership, Josh has learned one thing: conferences don’t grow your business, a c...
Show more...
Education
Episodes (20/91)
Breaking the Grade
Best of 2025: How Education Founders Can Turn Any Conference or Summit Into a Sales Engine That Builds Trust, Authority, and Pipeline
Some episodes don’t just inspire, they show you what execution really looks like. This one’s a real-time playbook in action. Originally LIVE from the University of Toronto at the Canadian EdTech Summit on 30th October, 2025, Josh breaks down exactly how education founders can stop wasting time and money at conferences, and start turning them into revenue-driving machines. After two decades in education and sales leadership, Josh has learned one thing: conferences don’t grow your business, a c...
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3 days ago
24 minutes

Breaking the Grade
Best of 2025: Karim Kuperhause & Rose Hastreiter on Why Education Founders Must Sell First, Master Objections, and Build a Repeatable Process Before Delegating or Scaling
Some episodes can't just be missed… this one is one of them. Why? Because it shifts how education founders think about sales, delegation, and building predictable pipelines. Originally streamed as a LinkedIn Live in October 2025, this replay brings back one of the most tactical, mindset-shifting conversations of the year. When Karim Kuperhause, CEO and Founder of HierSales, joined Josh for a candid LinkedIn Live conversation, later joined by Rose Hastreiter, founder and CEO of Leo...
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1 week ago
1 hour 3 minutes

Breaking the Grade
Best of 2025: Robert Martellacci on How Education Founders Stuck Chasing Sales Can Turn Relationships, Setbacks, and Partnerships Into Scalable Credibility and Revenue Growth
Some episodes don’t just share insights, they show education founders how to turn relationships, strategy, and innovation into measurable results. This one did. Robert Martellacci, founder and president of Mindshare Learning Media, has spent 25 years shaping Canada’s EdTech ecosystem, mentoring leaders, and creating opportunities for companies to scale. From launching Kevin O’Leary’s school division to moderating the Canadian EdTech Summit, Robert has seen firsthand how trusted relation...
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2 weeks ago
44 minutes

Breaking the Grade
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, entrepreneur, innovator, and founder of NorvaNivel, shared how she built a global company, scaled too fast, got fired from her own business, and rebuilt from the ground up, it became one of the most replayed and quoted episodes of the year. Her story hit home for education founders who’ve seen their pipeline stall or partner...
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3 weeks ago
50 minutes

Breaking the Grade
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 candid LinkedIn Live conversation, it wasn’t just another talk about personal branding; it was a deep dive into how education founders can turn an authentic online presence into real-world partnerships, pipeline, and predictable revenue. John, entrepreneur, investor, long-time education innovator, and Entrepreneur in R...
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1 month ago
49 minutes

Breaking the Grade
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 Thanksgiving episode. And it’s the moment we zoom out, breathe, look at the year we built together, and acknowledge every founder, leader, innovator, and listener who carried this show to its biggest year yet. This isn’t a highlight reel. It’s a gratitude letter. To 22 guests. To thousa...
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1 month ago
20 minutes

Breaking the Grade
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 begins. Where confidence starts. Where clarity is born. And when you nail those three? Everything else follows. Your LinkedIn sharpens. Your offer becomes clear. Your messaging finally lands with the buyers you’ve been chasing. But getting your headline right? That...
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1 month ago
15 minutes

Breaking the Grade
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. That hesitation kills more deals than rejection ever will. And if you’ve ever felt imposter syndrome creeping in before a big call or proposal, you already know how fast confidence cracks under pressure. Dr. Tamara Minott, PhD, “Dr. T”, knows that feeling well. ...
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1 month ago
26 minutes

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...
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1 month 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...
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2 months 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 ...
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2 months 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...
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2 months 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...
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2 months 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...
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3 months 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...
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3 months 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...
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3 months 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...
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3 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...
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4 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...
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4 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’...
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4 months ago
17 minutes

Breaking the Grade
Some episodes don’t just inspire, they show you what execution really looks like. This one’s a real-time playbook in action. Originally LIVE from the University of Toronto at the Canadian EdTech Summit on 30th October, 2025, Josh breaks down exactly how education founders can stop wasting time and money at conferences, and start turning them into revenue-driving machines. After two decades in education and sales leadership, Josh has learned one thing: conferences don’t grow your business, a c...