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EdSales Edge Show

A podcast by Josh Chernikoff

The strategy podcast for education founders, consultants, operators, and leaders selling into education. Hosted by Josh Chernikoff, a two-time education founder who has built and exited companies in this space, the show breaks down how selling into education actually works, across B2C, B2B, B2B2C and B2E, always through the lens of how education institutions really make decisions.

128 episodes since 2022. A new one every Sunday.

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Most recent episodes

Showing the latest 14 of 128.

  1. September 6, 2026 · 25 min

    The Perfect Client Test: Why Your Best Customer Could Be Holding You Back

    What if your best customer isn’t actually your perfect client? Josh Chernikoff learned this lesson while building his second business, an afterschool enrichment...

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  2. August 30, 2026 · 35 min

    Defending the Yes: Can Your Education Business Survive Buyer Scrutiny?

    You can love your solution and still make it incredibly hard to buy. Because your school buyer is wondering what happens to them if they say yes and you are wrong...

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  3. August 23, 2026 · 27 min

    AI Closes Nothing: Why Your Sales Numbers Still Depend on You

    AI can research the district. It can write the email. It can prepare the meeting, summarize the conversation, draft the proposal, and even write the follow-up. So...

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  4. August 16, 2026 · 30 min

    Take the Swing: Why Education Founders Should Enter Competitions & Apply for Grants

    You found the competition. You looked at the application. Then you told yourself: we’re not ready. And maybe you’re right. But what if that’s exactly why you should apply?

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  5. August 9, 2026 · 30 min

    People Buy People: Why Your Company Page Can't Close the Deal

    An education company almost always starts with one person: a founder, a teacher, or a practitioner who saw a problem and decided to solve it. Then something strange...

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  6. August 2, 2026 · 39 min

    Good Enough Wins: Why Better Solutions Still Get Rejected

    “We’re going to stick with what we have.” Every education founder has heard those words. Usually right after their strongest pitch. Usually after a great...

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  7. July 26, 2026 · 21 min

    The Sales Mistake Education Founders Make Before They're Ready to Scale

    You built the product. You know the problem. You know your solution works. So why should you have to be the one selling it? For many teacherpreneurs and education...

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  8. July 19, 2026 · 29 min

    The AI Mistake That's Costing You Sales Conversations

    AI has made it faster than ever to find prospects, research school districts, write personalized emails, create LinkedIn messages, and build follow-up sequences...

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  9. July 12, 2026 · 23 min

    The Credibility Trap: What Buyers Need Before They Buy Your Product

    Many teacherpreneurs and education founders work hard to build credibility. They earn certifications, highlight partnerships, showcase awards, and perfect their...

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  10. July 5, 2026 · 26 min

    The Missing Ingredient Behind Every Growing Education Business

    Every teacherpreneur and education founder starts with the same belief. If I create something that genuinely helps students, schools will want it. It sounds...

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  11. June 27, 2026 · 27 min

    The Teacherpreneur's Dilemma: Why Great Solutions Still Struggle to Grow

    Teacherpreneurs often believe growth will follow once they create something that works. It won’t. A strong solution is the starting line, not the finish line...

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  12. June 21, 2026 · 33 min

    The Summer Advantage: What Teacherpreneurs Should Build Before Fall

    The school year may be ending, but the work of building a business doesn’t stop. For teacherpreneurs, summer creates something rare: space. Space to think, plan...

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  13. June 14, 2026 · 26 min

    Stop Pitching: What Actually Gets a Superintendent’s Attention

    The fastest way to lose trust is to try to earn it too quickly. That’s a difficult reality for education companies. Dr. Jared Bloom sees it every day...

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  14. June 7, 2026 · 32 min

    Stop Building Alone: Why Community Changes Everything

    A lot of education founders wear independence like a badge of honor. Figure it out yourself. Push through. Keep going. Until one day you’re carrying every decision...

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The full archive of 128 episodes is on Apple Podcasts.

Listening is the free version.

If you want the system behind the show applied to your business, start with a 15-minute call.

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