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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
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.
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