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
How this EdTech Startup sharpened their message & went from struggling to selling!
Summary
Imagine a tool that could revolutionize how students manage their homework—built not by some big tech company, but by a parent and a 12-year-old visionary. Curious?
In this episode, we're diving into a startup story that's as unique as it gets. A co-founder whose biggest challenge wasn’t just building the tech but navigating the labyrinth of the education market...
Join me as I interview Brent Newton, founder of MyOwl, about the challenges he and his daughter faced in getting MyOwl off the ground.
MyOwl is an app that brings student's homework assignments into one centralized dashboard. The average student today has to use more than 143 apps to get their homework done. Talk about a logistical nightmare! So, when Brent and his daughter told other parents about their idea, the parents couldn't wait to get their hands on it. But when he tried to get the app partners on board and schools on board, it felt like he was banging his head against the wall...
Key Takeaways:
Tune in to hear…
- Why having a great product wasn’t enough—and the game-changing move Brent made to get schools on board.
- The crucial shift in his messaging that turned MyOWL from a “maybe” to a “must-have.”
- The surprising power of community—how being part of a group of other education founders gave him the breakthrough he needed.
- AND… hear all about his experience inside the 3E EdSales Elevation Experience.
Chapters
00:00 MyOWL: Revolutionizing Homework Management
05:30 The Impact of the Ed Sales Elevation Experience
10:55 The Power of the Mastermind Group
13:46 Networking and Support for Education Entrepreneurs
21:09 Join the Homework Revolution with MyOWL
Resources/ Links:
- Connect With Brent Newton: Brent Newton | LinkedIn
- Go to MyOwl Website: myOwl | Homework Managed
- Interested in Growing Your Education Business? Book your FREE Strategy Call.
- Learn More about the 3E Edsales Elevation Experience: Join the waitlist for the next cohort here.
