What I'm seeing from founders selling into schools.

• September 6, 2026

  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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• August 30, 2026

  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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• August 23, 2026

  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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• August 16, 2026

  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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• August 9, 2026

  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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• August 2, 2026

  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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• July 26, 2026

  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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• July 19, 2026

  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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• July 12, 2026

  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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• July 5, 2026

  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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• June 27, 2026

  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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• June 21, 2026

  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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• June 14, 2026

  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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• June 7, 2026

  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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There are around 85 published posts in total. The full archive gets migrated onto this site, properly indexed and searchable, as part of the build. Right now it lives on a separate sub-site with no navigation back here.