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
65 episodes
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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Do the Opposite of Everything You’ve Been Doing: How Seinfeld’s George Costanza Unlocks Lead Gen Clarity for EdTech Founders
Let’s start with a sitcom—and a truth bomb.In Seinfeld Season 5, Episode 22 ("The Opposite"), George Costanza hits rock bottom. No job. No love life. No confidence.So he flips the script. “If every instinct I have is w...
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17:42
Breaking Borders: How Smart EdTech Founders Build Scalable Companies Without Losing Local Trust
If you’re trying to grow your education business beyond where you started—this episode is for you.Because whether you’re moving from one country to another, or just one state to the next…The real challenge isn’t translation.It...
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33:06
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The Speaking Strategy: How Education Founders Fast-Track Credibility, Confidence, and Sales Momentum
LinkedIn builds your credibility — Speaking amplifies it.In this episode of Breaking the Grade, I’m sharing how I went from avoiding stages entirely to speaking at in the last 13 months at Penn GSE, the University of C...
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20:34
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From Ghosted to Booked: How Ashton Tate Filled His Calendar with Qualified School Leads
You’re not afraid of hard work.You’ve put in the hours.You’ve sent the emails.You’ve done the demos.And still—no one’s biting.That was Ashton Tate.Founder of...
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26:03
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You Don’t Just Sell to Schools—You Earn Their Trust: How Edtech Founder Paul Moch Built an Education Business That Got Acquired
You think your sales process is tough?Try launching a brand new EdTech company during a global pandemic—while building trust with schools that aren’t exactly raising their hands.In this episode of Breaking the Grade, I sat down wi...
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20:53
Busy Isn’t Booked: The Silent Sales Mistake Most Founders Miss
You’re busy. But you’re not booked.You’re showing up on LinkedIn.You’re attending conferences.You’re tweaking your SEO.You’re following the playbook everyone told you to run.And still—your pipeline’s empty.<...
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20:29
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Cracking the Code: How to Sell Education Products in High-Stakes Markets
Recorded live at IFE in Monterrey, Mexico, this episode features Beatriz Guillen, Executive Director at The Resource Foundation—a leader focused on strengthening education outcomes across Latin America.While her work center...
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22:03
From Chaos to Clarity: How One Founder Rebuilt His EdTech Biz from the Ground Up to Revenue Way Up
Too many education founders build something incredible—only to realize they can’t sell it.They try to figure it out themselves… piecing together advice from free webinars, Twitter threads, and late-night YouTube binges. But without a pro...
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30:37
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Why Most Education Companies Burn Out Before They Scale—And the Fix That Actually Works
You’ve got the vision. The team. The momentum.So why does it feel like you’re sprinting on a treadmill with no finish line in sight?Here’s the truth: Most education companies don’t burn out because of a bad idea.They burn out bec...
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25:17
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LinkedIn Connection to Contract: Josh's Proven Six-Step EdSales Method (No Paid Ads/Funnels/Cold Calls)
You’ve added decision-makers on LinkedIn.You’ve liked a few posts, maybe even commented.You’re showing up… but nothing’s turning into a call, let alone a contract.Sound familiar?That’s what I call the LinkedIn ill...
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21:10
Struggling to Sell to Schools or Universities? (An Expert in HigherEd Tells You How to do it Right)
Selling into education institutions—whether K–12 or higher ed—isn’t just about having a great product.It’s about understanding how those institutions work: how decisions are made, what roadblocks slow things down, and how to position you...
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20:32
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The Conference Playbook: How Education Companies Get Conferences Wrong (And How to Fix It)
Does this sound familiar?You just spent thousands of dollars flying to ANOTHER education conference, setting up a booth, shaking hands with decision-makers. You collected a stack of business cards, had great conversations, and walked aw...
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29:53
IFE Conference 2025 (Mexico): Breaking Barriers -- AI and Strategic Partnerships Shaping Education
The education sector is buzzing with AI, but are schools and EdTech businesses truly leveraging it for sustainable growth? In this live episode, we cut through the hype to explore how AI, combined with strategic partnerships, can drive real imp...
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26:18
Why Most Startups Get Investment Wrong—and How to Fix It
SummaryWhen you're growing your education business, one big question always comes up—should you seek investment or bootstrap your way to success? In this episode, Josh Chernikoff breaks down the real challenges behind...
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21:07
Before You Hire a Sales Team...The Steps Founders Can’t Skip
SummaryIn this episode of Breaking the Grade, Josh Chernikoff tackles the big question: when’s the right time to bring on a sales team for your education-focused business? He shares why rushing to hire too soon can be a m...
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18:33
Secrets behind unlocking 7-figures in sales...How this seasoned entrepreneur transformed his sales process.
SummaryIn this episode of Breaking the Grade, I chat with Ernie, a seasoned leader who's been navigating the ever-changing education landscape since 2001. He shares valuable insights on how he completely transformed his ...
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26:23
From One-Off Sales to Repeatable Revenue...How Future Makers Transformed Their Business
SummaryNine years of building a business—and then, overnight, everything changes. Suddenly, you’re scrambling to keep things afloat, unsure of your next move. That’s exactly what happened to Matt Barinholtz, founder o...
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34:49
Mastering Sales Planning in the Education Space
Summary:In this episode of Breaking the Grade, Josh Chernikoff and Toni McMurray tackle the challenges of sales planning for education companies as the new year approaches. If you’re feeling overwhelmed by the tight sales...
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31:29
Mastering the Education Sales Cycle & Secrets to Staying Top of Mind and Closing Deals
Summary:Sales in the education space can feel like an endless maze—long cycles, multiple decision-makers, and constant resistance. In this episode, Josh Chernikoff pulls back the curtain on the challenges EdTech founders face whe...
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18:07
Why Waiting to Sell in the Education Sector Can Cost You...& when’s the right time to start selling
Summary:Wondering when you should really start selling in the education market? In this episode, Josh Chernikoff dives into the right timing and approach for effective sales in the education space. Spoiler: it’s not just a...
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17:30
A Better Approach to Sales Calls for Education Companies… How to sell without being salesy.
Summary:Are your sales calls feeling like one-way pitches instead of real conversations? In this episode, Josh Chernikoff uncovers a simple yet powerful shift that could change how you approach every sales call moving forward. Spo...
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19:31
The Better Demo Method To Sell More Education Services & Products
Summary:Selling to schools and districts is more than just having a good product—it’s about really understanding the specific challenges and needs of the education market. In this episode, Special Guest: John Gamba (Entrepreneur i...
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31:45
How This EdTech Company Transformed Their Sales Process And Went From Stagnation to Leads In Just 8 Weeks
Join me as I sit down with Chris and Corey from Rocket PD to talk about how they revamped their entire sales process to feel more natural and focused on building relationships with their ideal customers. Chris and Cory have years of SaaS experi...
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31:07