Breaking the Grade

Josh Chernikoff

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.

  1. Best of 2025: John Gamba on How Education Founders Can Rebuild Trust, Visibility, and Pipeline Through Authentic LinkedIn Strategy

    4D AGO

    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 Residence and Director of Innovative Programs at Penn GSE, broke down how today’s founders can win attention without losing authenticity.  Together, they unpacked what truly builds credibility in the digital age, and why education founders who lead with voice, vulnerability, and value always outperform those chasing trends. From leveraging platforms like ERDI to connect with district leaders, to mastering LinkedIn commenting and storytelling that drive genuine engagement, this episode turned into a masterclass in credibility-based marketing. And when the conversation shifted to AI-generated “slop,” John didn’t hold back. He reminded every education founder that your humanity is your headline, the thing that separates connection from noise and trust from vanity metrics. Originally streamed as a LinkedIn Live in March 2025, this replay captures a moment when authenticity wasn’t just a buzzword, it was the difference between being seen and being sought after. 🚨 Your next contract won’t come from another cold DM,  it’ll come from consistent, credible visibility. What You’ll Learn in This Episode 1️⃣ From Presence to Pipeline How to use LinkedIn to build relationships that convert, without ever sounding salesy. 2️⃣ Visibility that Builds Credibility The difference between posting and positioning, and how authentic engagement outperforms paid ads. 3️⃣ The Power of Platforms, conferences and summits  Why relationships with decision-makers still drive the education market, and how to show up where they are. 4️⃣ Avoiding AI “Slop” How to balance technology with authenticity, and make sure your content sounds like you, not a bot. 5️⃣ Consistency as a Growth Strategy Why education founders who show up daily, with clarity and value, always attract the right clients and partners. If you’ve ever felt invisible online, struggled to turn posts into pipeline, or questioned if authenticity still works in an AI-driven world, this episode will reignite your voice and your strategy. 📩 DM me “LINKEDIN” and I’ll show you how education founders inside the EdSales Elevation Experience rebuild credibility, community, and consistent lead flow through LinkedIn. 📤 Know a founder who’s posting but not converting? Share this episode, it’s the clarity they’ve been missing. ✍️ Love the show? Subscribe on Apple Podcasts and Spotify so more education founders can turn presence into profit and authenticity into advantage. #EdSales #EducationFounders #BreakingTheGrade #ClarityConverts #LinkedInStrategy #FounderMindset #LeadGeneration #JohnGamba #JoshChernikoff #EdTech #AuthenticMarketing

    49 min
  2. The Gratitude Episode: 22 Guests, 63 Countries, and a Community That Turned 2025 Into Our Most Meaningful Year Yet

    NOV 23

    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 thousands of listeners across 63 countries. To the founders who shared their stories, their vulnerability, their setbacks, and their victories, and left fingerprints on this community. In this episode, I walk through the people who shaped the year, the episodes that shifted perspectives, the conversations that changed founders’ confidence, and the personal moments that defined 2025, including the support this community gave me after my father passed in June. This is the season wrap. The celebration. The thank-you we all need before stepping into 2026. If you’ve ever been part of this community, on the mic, on a LinkedIn Live, or in the comments, this episode is a tribute to you. 5 Big Takeaways for Education Founders 1️⃣ Your Community Is Your Credibility You don’t grow because you post more. You grow because people trust you, share your work, and bring others into the room. This year proved that: every guest, every comment, every share expanded our reach. 2️⃣ Gratitude Builds Momentum Education founders underestimate the power of reflection. When you acknowledge how far you’ve come — your pipeline, your progress, your resilience — you move forward with clarity and energy instead of fear and pressure. 3️⃣ Every Story Strengthens the Ecosystem From Ernie Delgado to Dr. Tamara Minott, every guest brought a perspective that made another education founder feel understood, inspired, or equipped to take the next step. When one founder grows, the whole community levels up. 4️⃣ Clarity Grows When You Slow Down This episode is a reminder: pause. Look back. Identify what worked. Those insights build stronger frameworks, better decisions, and clearer offers in the year ahead. 5️⃣ You Can’t Scale Alone 2025 proved it — collaboration, mentorship, community guidance, and shared experience are the multipliers. No founder wins in isolation. The people around you shape your breakthroughs. 🙏 If you listened, shared, commented, DM’d, or showed up this year — thank you. This show is stronger because of you. This community is growing because of you. And 2026 will be bigger because of the foundation you helped build in 2025. 📩 If this episode resonated, send me a message. I’d love to hear what you’re grateful for as we wrap 2025. 📤 Know a founder who needs encouragement going into the new year? Send them this episode — it might be exactly what they need. ✍️ Love the show? Subscribe on Apple Podcasts and Spotify so more founders can turn clarity into action, and gratitude into fuel for their next breakthrough. #EdSales #BreakingTheGrade #EducationFounders #Gratitude #Leadership #FounderMindset #CommunityGrowth #ClarityConverts #JoshChernikoff

    20 min
  3. The Headline Mistake: How eight words on LinkedIn unlocked a $100k repeatable pipeline.

    NOV 16

    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’s the hard part. It seems simple, just 220 characters, right? But distilling your value into one clear line takes a level of clarity most founders haven’t reached. It’s some of the toughest positioning work you’ll ever do. That’s exactly why it matters. Because if you can’t clearly say who you serve and what you deliver in one line, how will you do it in your offers, your sales calls, or your content? Your headline isn’t your job title. It’s the foundation of everything else. And right now, if yours reads like a résumé, “CEO of…” “Passionate about education…”, you’re not just losing clicks. You’re losing trust before anyone reads your profile. You’re leaving money on the table with every scroll. Josh breaks down exactly how founders inside the EdSales Elevation Experience turned vague, invisible headlines into $100K+ in new contracts, not by posting more, but by getting brutally clear on positioning. From Edwin Blanton, Ph.D at University of Texas San Antonio to Paul King in NYC, he breaks down the exact framework these founders used to go from vague and forgettable to scroll-stopping and lead-generating. This isn't copywriting magic. It's clarity work. And it's the beginning of your credibility, your confidence, and your ability to communicate your value with precision. 🔑 5 Big Takeaways for Education Founders 1️⃣ Your Headline Is Where Credibility Begins Before anyone reads your content or takes a call, they read your headline. If it's vague or generic, you've already lost them. This is where trust starts, or dies. 2️⃣ Clarity Here = Clarity Everywhere When you can nail your headline, something shifts. Your offers get sharper. Your messaging lands harder. Your confidence grows. It all starts with 8 words. 3️⃣ This Is Hard Work (And That's Why It Matters) Don't let the simplicity fool you. Condensing your value into one clear line is some of the toughest positioning work you'll do and most founders skip it entirely. 4️⃣ The 3E Framework: Credibility, Confidence, Clarity Josh walks through the exact framework that turns invisible headlines into pipeline-generators. Every word has a job. Every word matters. 5️⃣ One Line Can Transform Your Entire Business Founders like Edwin Blanton and Paul King didn't just change their headline. They changed their positioning, their pipeline, and their revenue – $100K+ in new contracts from getting this one thing right. Your headline is either building your credibility or killing it. It's either giving you confidence in your positioning or leaving you guessing. It's either creating clarity in your business or keeping you stuck in vagueness. Make it the line that stops the scroll, builds trust instantly, and starts the conversations that turn into contracts. 📩 DM me "Headline" and I'll send you the exact framework we use inside the EdSales Elevation Experience to turn clarity into contracts.

    15 min
  4. Hesitation Is a $250K Mistake: Dr. Tamara Minott on How Education Founders Close Deals With Confidence

    NOV 9

    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. Before becoming the Director of College & Career Readiness at Coney Island Prep, she was a higher-ed expert with a doctorate, a dream, and a business idea, ClarifyEd LLC, that never seemed to get off the ground. She’d filed the LLC back in 2019 but kept delaying, caught between planning and perfectionism. When she joined the EdSales Elevation Experience, everything shifted. Week by week, she went from isolated planning to structured accountability. She mapped her offer, faced her imposter syndrome head-on, and discovered that confidence isn’t inherited, it’s built through execution. Twelve weeks later, the founder who used to overthink every decision was leading strategy sessions, pitching schools, and shaping a college-readiness program for the same Brooklyn community she grew up in. Her confidence didn’t just return, it scaled. If you’ve been questioning yourself instead of closing with conviction, this is the episode you can’t afford to miss. Because clarity, confidence, and consistency aren’t just mindset wins, they’re what drive revenue that lasts. 5 Big Takeaways for Education Founders 1️⃣ Confidence Is a Skill, Not a Trait Dr. T didn’t “get” confidence, she built it through structure, accountability, and small wins that proved her authority to herself. 2️⃣ Clarity Comes From Action, Not Planning You don’t think your way into confidence, you act your way into it. Dr. T learned to ship before she felt ready. 3️⃣ B2C to B2B: Scaling Starts With Self-Belief When she stopped playing small (“one family at a time”) and started pitching schools and districts, everything changed. 4️⃣ Your 9–5 Can Fund Your Confidence Her new director role isn’t a distraction, it’s an accelerator that builds credibility and multiplies long-term business value. 5️⃣ Community Builds Courage Confidence grows faster when founders stop pretending they’ve got it all figured out. Real experts still need real support. Dr. T’s story is your wake-up call: hesitation costs contracts. Because until you believe in your expertise enough to act on it, no buyer will either. 📩 Want to turn confidence into contracts? DM me “Confidence” and I’ll share the exercise we use inside the EdSales Elevation Experience to help founders find their conviction fast. 📤 Know a founder stuck in overthinking or self-doubt? Send them this episode, it could be the reset that saves their next quarter. ✍️ Love the show? Subscribe on Apple Podcasts and Spotify so more education founders can turn confidence into clarity, and clarity into revenue. #EdSales #FounderLedGrowth #BreakingTheGrade #EducationSales #K12 #ConfidenceShift #LeadGeneration #ClarityConverts #EdTech #FounderSales #EdTechStartup #SalesMindset #ImposterSyndrome #Leadership

    27 min
  5. You Crushed the Demo—But Still Can’t Close: The $100K Mistake Education Founders Keep Making

    NOV 2

    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 products, not pain. They confuse polish for persuasion. Head nods happen… but deals don’t. Part 2 picks up exactly where that left off. Now that your demo is solid, the real question is: what happens after the head nods? This is the next leak in your funnel, the moment when enthusiasm quietly turns into indifference if you don’t take control. Because in founder-led sales, praise isn’t pipeline, confusion costs money, and every vague next step is a lost opportunity. This episode is your wake-up call. Josh reveals how the top 10% of education founders, leaders like Paul King, Kathryn Adabonyan, and Wayne Bovier, stopped collecting compliments and started collecting contracts. They replaced feature tours with funding-aligned conversations that moved buyers from interested to invested. If your demos impress but don’t convert, this is your reset before another quarter disappears. 5 Big Takeaways for EdTech Founders 1️⃣ Why Praise Alone Doesn’t Close Deals Head nods, smiles, and “This is exactly what we need” don’t guarantee contracts. Josh explains why enthusiasm stops short of intent and how silence after the demo is actually a polite no. 2️⃣ The One Step Founders Often Miss After a Demo It’s not the demo that fails, it’s the next move. Josh shows why every vague next step costs weeks of follow-up, lost momentum, and deals that should already be booked. 3️⃣ How to Turn Your Product Pitch Into a Partner Conversation Shift your mindset from “here’s my product” to “here’s how we solve this together.” Josh breaks down how funding-aligned conversations make buyers see the value and act on it. 4️⃣ Clarity Is the Secret Weapon in Founder-Led Sales If your pitch is clear, buyers can retell your value to their team. Josh shows how tying outcomes to KPIs like attendance, test scores, and funding makes your offer tangible, urgent, and impossible to ignore. 5️⃣ Urgency, Fit, and Proof Drive Decisions Josh walks through the exact elements buyers scan for: clarity, proof, fit, confidence, and urgency. Miss any one of these, and the deal stalls, even after a perfect demo. Your buyers aren’t ghosting because they don’t care. They’re ghosting because your demo stopped one step too soon. 📩 DM me “Demo” to see the exact framework education founders use inside the EdSales Elevation Experience to turn clarity into contracts, and conversations into cash. 📤 Know a founder stuck after “wow”? Send them this episode, it could save their next quarter. ✍️ Loved the show? Subscribe on Apple Podcasts and Spotify so more education founders can stop losing deals after “wow” and start turning demos into dollars. #EdTech #FounderSales #LeadGen #EdSales #BreakingTheGrade #DemoStrategy #PipelineGrowth #JohnGamba #JoshChernikoff #ClarityConverts

    19 min
  6. From Betrayal and Courtroom Battles to Closed Deals: Robespierre Reyes on Rebuilding Credibility, Team Alignment, and Education Deals That Close

    OCT 26

    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 founders. Josh met Rob at the IFE Conference in Monterrey, Mexico. After sharing a panel, they dug into the side of entrepreneurship few talk about: betrayal, exhaustion, and rebuilding in a way that generates real sales opportunities. Today, Rob is the Managing Director at the Berkeley Executive Institute and the Strategic Advisor for the IFE Launch-Accelerator, helping education founders and startups turn credibility into contracts that close. Here’s the truth for education founders: Misaligned teams, broken trust, and bad partnerships don’t just cost money, they kill lead flow and stall your sales pipeline. In this episode of Breaking the Grade, Josh and Rob unpack exactly how to rebuild your credibility, team, and systems so your leads, partnerships, and deals start converting again. What You’ll Learn in This Episode 1️⃣  Why the Wrong Co-Founders Kill Lead Flow Rob shares how ignoring red flags in team selection tanked deals before they even hit the market, and what to do instead. 2️⃣ The Court Battle That Rewired His Mindset A brutal court fight taught him that integrity and transparency are the fastest ways to rebuild trust, attract leads, and generate opportunities. 3️⃣ The Hidden Cost of Burnout Overwork didn’t just affect Rob, it stalled traction. Learn how pacing and priorities can keep leads flowing consistently. 4️⃣ Failure is a Lead-Generation Strategy Being open about mistakes doesn’t scare investors or partners, it draws the right opportunities and opens doors for deals. 5️⃣ Generosity + Candor = Repeatable Lead Flow Leading with honesty and giving first rebuilt Rob’s network, partnerships, and next big ventures, all while boosting conversion rates and pipeline growth. If you’ve ever lost traction, seen your pipeline dry up, or felt partnerships blocking your growth, this episode shows how to turn broken deals, misaligned teams, and credibility gaps into a repeatable lead-generating engine. 📩 DM me “Rebuild” and I’ll show you how education founders inside the EdSales Elevation Experience turn setbacks into clarity, credibility, and closed contracts. 📤  Know an education founder stuck in stalled deals? Share this episode, it could save their next partnership or pipeline. ✍️ Love the show? Subscribe on Apple Podcasts and Spotify so more education founders can turn breakdowns into breakthroughs, and failure into fuel. #EdSales #EducationFounders #BreakingTheGrade #ClarityConverts #FounderMindset #StartupRecovery #RobespierreReyes #JoshChernikoff #EdTech #FounderLessons

    19 min
  7. From Confusion to Clarity: JD Mosley-Matchett on the Message Shift That Turns Unclear Offers into Scalable, Trust-Building Growth for Education Founders

    OCT 19

    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 J.D. Mosley-Matchett, PhD 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 supporters couldn’t answer the question: “What exactly does she do?” After joining accelerators and business programs, she kept hearing the same feedback:      “You’re clearly brilliant, but we don’t get it.” Everything changed when she joined the EdSales Elevation Experience. For the first time, JD wasn’t trying to figure it out alone. Surrounded by other education founders and guided by the Signature Solution framework, she slowed down, wrestled through the hard questions, and built total clarity around her offer. It wasn’t easy, there were moments of doubt and tough feedback, but she stuck with it. And that discipline turned confusion into confidence. Her message finally clicked. Her communication connected. And for the first time, clients instantly understood the transformation she was offering. Because clarity isn’t a marketing skill, it’s a sales weapon.  5 Big Takeaways for Education Founders, EdTech Leaders & Higher Ed Innovators 1️⃣ Smart but Unclear Doesn’t Sell JD’s story proves even the best product fails if buyers can’t instantly understand its value. 2️⃣ The Signature Solution Framework How she turned years of scattered expertise into one clear, visual process that resonates with decision-makers. 3️⃣ Friction Creates Breakthroughs The hardest exercise, defining her 9-step client journey, became the clarity unlock that repositioned her entire offer. 4️⃣ Ask Before You Sell The “Raise Your Hand” strategy taught JD how to lead with curiosity, not a pitch, and turn conversations into contracts. 5️⃣ Community Is the Multiplier Inside the right cohort, collaboration replaces confusion. JD’s growth accelerated because she wasn’t doing it alone. If you’re an education founder, EdTech leader, or higher ed innovator who’s tired of hearing “I’m not sure I get it,” this episode is your turning point. JD’s journey proves that scaling isn’t about talent, it’s about clarity, consistency, and the right framework. 📩 DM me “Clarity” and I’ll show you the exact Signature Solution framework JD used inside The EdSales Elevation Experience to turn her message into momentum. 📤 Know an education leader stuck in confusion? Send them this episode, it might be the clarity shift that changes everything. ✍️ Loved the show? Subscribe on Apple Podcasts and Spotify so more education founders, EdTech leaders, and higher ed changemakers can turn clarity into contracts and messaging into momentum. #EdTech #EducationSales #FounderSales #HigherEd #MessagingStrategy #BreakingTheGrade #ClarityConverts #EdSalesElevation #JDmosleymatchett #JoshChernikoff

    19 min
  8. The Mindset Reset: Mitch Weisburgh On How Education Founders Can Master Mindset, Beat Burnout, and Close Strong Deals

    OCT 12

    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 into self-sabotage. That’s why this episode of Breaking the Grade is a must-listen for every education founder who's tired of feeling stuck, drained, or second-guessing themselves when results slow down. Josh sits down with Mitch Weisburgh, mindset coach, author of the Mindshifting series, and former advisor to top education publishers and EdTech companies, to unpack how mental mastery outperforms any sales tactic when pressure peaks. Mitch draws from elite performers like Mike Tyson and Roger Federer to reveal why the best closers don’t chase perfection, they train their minds to stay calm, focused, and ready when everything’s on the line. This isn’t fluff. It’s the field-tested psychology of education founders who close under pressure while everyone else freezes. 5 Power Moves for Education Founders when the pressure's on: 1️⃣ When Strategy Crumbles Under Pressure Even great plans collapse under stress. Mindset, not tactics, keeps your pitch alive when objections hit. 2️⃣ Stories That Close (or Kill) Deals Shift from “What if I lose?” to “I’m built for this.” Reframing turns panic into precision and control. 3️⃣ Perfectionism Is the Silent Killer Flawless demos freeze founders, and Federer’s “win even when losing 49% of points” mindset builds resilience and results. 4️⃣ Energy > Effort More grinding won’t fix fatigue. Quiet stress, turn pressure into fuel, and stay in flow. 5️⃣ Objections = Openings “No” is feedback. Discover the 5 conflict styles that flip resistance into trust and momentum. If your mindset is the missing link between stalled outreach and closed contracts, this episode gives you the tools to quiet the noise, reclaim your edge, and finish stronger than you started. 📩 Want help reframing your fears into a winning mindset? DM me “Mindset” and I’ll share a simple exercise to visualize success before your next call. 📤 Know a founder battling fatigue or stuck leads? Send them this episode; it could be the shift that saves their quarter. ✍️ Love the show? Subscribe on Apple Podcasts and Spotify so more education founders can turn mindset mastery into deals that stick. #EdSales #EducationSales #FounderLedGrowth #K12 #BreakingTheGrade #ClarityConverts #LeadGeneration #MindsetShift #EdTech #FounderSales #Q4Wins #SalesMindset #SchoolSales #EdTechStartup #SalesStrategy

    37 min
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Ratings & Reviews

5
out of 5
4 Ratings

About

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.

Information

  • Creator
    Josh Chernikoff
  • Years Active
    2022 - 2025
  • Episodes
    87
  • Rating
    Clean
  • Copyright
    © 2025 Breaking the Grade
  • Show Website
    Breaking the Grade

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