EdSales Edge Show
EdSales Edge is the strategy podcast for education founders, consultants, operators, and leaders selling into education.
For years, this show was known as Breaking the Grade, a space to challenge the status quo in education and think differently about how change actually happens. That mission hasn’t changed.
But the work has.
Over time, one thing became clear:
Education founders don’t just need inspiration.
They need clarity.
They need real strategies for selling into schools.
They need predictable ways to generate leads.
And they need to understand how trust is built in a system that doesn’t move fast, and doesn’t give many second chances.
EdSales Edge was rebuilt to match that reality.
Hosted by Josh Chernikoff, a two-time education founder who’s 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.
This is not a show about hacks, shortcuts, or quick wins.
Education doesn’t work that way.
On EdSales Edge, you’ll hear:
- Real strategy for selling into education systems
- Conversations with education decision-makers who explain how buying actually happens from the inside
- Stories from founders, CEOs, and operators who’ve built real traction selling into schools—what worked, what didn’t, and what actually moved deals forward
- Teachings from the EdSales Elevation Experience, the system used to help education founders move from unclear and invisible to trusted and in demand
You’ll learn how to:
- Define your Perfect Client
- Pull the right credibility lever
- Move from being hidden… to trusted… to building a real lead engine
Josh is joined by his good friend and mentor, John Gamba—Director of Innovative Programs and Entrepreneur-in-Residence at Penn GSE, and a former education founder who’s led companies through real growth and successful exits. John brings the institutional lens, shaped by years inside districts, universities, and education systems, seeing how decisions get made when the doors are closed and what earns trust over time.
Together, they sit on both sides of the table, the builder side and the system side, so the show stays grounded in reality, not sales theory.
If you sell into education and you’re tired of guessing,
guessing who to talk to,
guessing how decisions get made,
guessing why interest doesn’t convert—
this show is built for you.
EdSales Edge
Clarity. Credibility. Real traction.
If you sell into education, this is where you earn your edge.
EdSales Edge Show
Why Most Startups Get Investment Wrong—and How to Fix It
Summary
When 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 this decision.
He shares lessons from his own journey, the mistakes founders make when chasing investment too soon, and what it really takes to build a business that attracts the right investors (if you even need them). We also get into smart ways to bootstrap, key signs that you’re actually ready for investment, and why a strong lead generation system is a must before you even think about bringing on investors.
If you're debating whether to seek investment or go it alone, this episode will help you figure out the right next step.
Tune In to Hear:
- The warning signs that you’re pitching too early — and what investors really want to see.
- How to tell if your business needs more capital — or just a better sales strategy.
- Why funding isn’t always the answer — and what might be holding you back instead.
- The hidden costs of taking investment: What no one tells you about giving up equity and control — and how to make the right call.
- Why so many education entrepreneurs chase investment too soon — and what to focus on instead to grow sustainably.
- Why more money won’t fix a broken sales pipeline: The crucial step education founders must take before seeking investors.
Chapters
00:00 - Introduction to Funding vs. Bootstrapping
02:59 - Understanding the Pros and Cons of Investment
10:00 - Identifying the Right Time for Investment
15:09 - Bootstrapping Strategies for Growth
21:59 - Preparing for Investment: Key Benchmarks
26:47 - Final Thoughts and Call to Action
Links
Josh Chernikoff
Josh Chernikoff LinkedIn
