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
Take the Swing: Why Education Founders Should Enter Competitions & Apply for Grants
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
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?
In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, and John Gamba, Entrepreneur-in-Residence at Penn GSE, challenge one of the most common excuses education founders and teacherpreneurs make: waiting until they feel ready before putting their business in the arena.
Because competitions aren't just about winning money, trophies, or a spot on a stage.
They're pressure tests.
Whether it's the Milken-Penn GSE Business Plan Competition, South by Southwest EDU, ASU GSV Cup, StartEd/EdTech Week, or Shark Tank-style competitions, the value isn't limited to what happens if you win. Grants like SBIR and IES create another opportunity to put your business through a rigorous evaluation while pursuing non-dilutive funding.
The application forces you to answer questions you may have been avoiding: Who actually buys this? What problem are you solving? Why does your solution win? What's the evidence? How big is the opportunity? What's different about you? And how do you scale?
If you can't answer those questions clearly, the competition didn't expose your weakness.
It exposed your next move.
WHY THIS MATTERS
Education founders and teacherpreneurs get so close to their businesses that they can't always see what's missing.
A competition or grant application creates productive pressure, feedback, and a chance to challenge your assumptions.
Sometimes the most valuable outcome isn't advancing.
It's finally seeing what needs to change.
KEY STRATEGIES & MENTAL MODELS
1️⃣ Fear is a liar. Avoidance is fear's best friend.
"We're not ready" can be an honest assessment—or an excuse to avoid being tested.
2️⃣ The application is a business-development exercise.
Use it to sharpen your buyer, problem, value proposition, market, evidence, and path to scale.
3️⃣ Not winning isn't failure.
Use the feedback to make the next application—and the business—stronger.
4️⃣ Keep swinging.
Some founders apply once. Others keep improving until they advance, reach the finals, or win.
5️⃣ Choose the right arena.
Find opportunities that offer the right mix of funding, feedback, mentorship, exposure, or connections.
WHO THIS EPISODE IS FOR
- Education founders
- Teacherpreneurs
- EdTech leaders
- Education Founders considering competitions, grants, or accelerators
NEXT STEP
Find one competition or funding opportunity that fits your business.
Don't wait until you're certain you'll win. Apply because the process can make you better.
Then text "90 DAYS" to 771-333-4233.
Get the 90-Day Founder Challenge — a practical framework for your next 90 days.
Teacher-founders: limited 1:1 planning sessions are available.
🔁 SUBSCRIBE & SHARE
Follow EdSales Edge and send this to an education founder who's waiting until they feel ready.
Prepare like you plan to win. Take the swing anyway.
Connect with Josh Chernikoff
Founder, Edsales Elevation Experience
Host, Edsales Edge Show
🔗 LinkedIn: https://www.linkedin.com/in/joshuachernikoff/
📘 Facebook: https://www.facebook.com/joshua.chernikoff
📸 Instagram: https://www.instagram.com/joshuadcdc/
📩 Email: Jc@joshchernikoff.com
Join the Edsales Entourage
Get closer to the conversations, strategies, and operators inside the ecosystem:
👉 https://www.skool.com/entourage
