EdSales Edge Show

You've sunk years into a product you believe in. And a superintendent still won't reply to a single email.

It's tempting to blame the product, the pitch, or the audience.

Look closer at the request itself: a stranger is asking a busy district leader for their time to watch a demo. That's a lot to ask before they have any reason to believe you understand their world.

There's a smaller yes that gets buyers talking. Samuel Rabkin of MediatorSpark found it, and walked away from the Institute for Education Innovation (IEI) in Utah with 12 superintendent conversations.

In this episode of EdSales Edge, Josh Chernikoff opens Stage 3 of the EdSales Revenue Machine: Raise Your Hand. You'll hear what a raised hand really is, the four ingredients that make one more likely, and the mistake founders make the moment a buyer finally shows interest.

WHY THIS MATTERS

Silence from a buyer feels like a verdict on your product. Usually it isn't. It's a verdict on the first ask. Fix how you open and the same product, deck, and pitch start getting answers.

🔑 KEY STRATEGIES & MENTAL MODELS

1️⃣ Know a real raised hand. A like is attention. A download, maybe interest. "We're struggling with this problem" is one.

2️⃣ Use the four ingredients. Target the right buyer, name a problem they care about, build credibility, make a fitting invitation.

3️⃣ Lead with their problem, not your platform. Show buyers you understand their challenges before introducing your solution.

4️⃣ Make the first yes easy. Swap the big demo request for a simple, relevant invitation to start talking.

5️⃣ Run a 15-minute, no-pitch interview. Ask about their challenges, listen without interrupting and dig deeper to understand their needs first.

🎯 WHO THIS EPISODE IS FOR

• Education and EdTech founders selling to K-12 and higher education.
• Founders whose outreach to superintendents, principals, or administrators goes unanswered.
• Founders who default to asking for demos.
• Anyone who wants more meaningful buyer conversations instead of more meetings.

🚀 NEXT STEP

Think of the last email you sent to a district leader that never got a reply.

Read it as if you were the superintendent.

What are you asking them to do, and what have you given them to go on?

Then press play. Josh walks through how to start that conversation differently, and what to do the moment a buyer answers.

Listen with that email in front of you and see what you'd change.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and send this to a founder who keeps asking for demos.

Before they buy, they have to speak up. Give them a reason to.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

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Are free pilots a trap? What actually counts as proof? Does your LinkedIn content convince the people holding the budget that you're worth trusting?

These are real questions education founders have been bringing to Coach Ed, the AI coach inside the EdSales Revenue Machine. Built around a proven coaching method, Coach Ed helps founders work through customer acquisition challenges, sharpen their strategies, and tackle the hard questions that come with winning customers. In the last 30 days alone, Coach Ed answered 2,827 questions, with founders spending more than 165 hours working with him.

On this episode of EdSales Edge, Josh Chernikoff brings those questions to his co-host, John Gamba, Entrepreneur-in-Residence at Penn GSE with 30 years of experience in education. Inspired by SmartLess, the comedy podcast where Jason Bateman, Sean Hayes, and Will Arnett surprise one another with mystery guests, Josh puts John in the hot seat with a guest he never saw coming.

The guest?

Jolene Levin, an education marketplace leader who has spent 17 years building a learning-space company and championing women in education leadership.

From why free pilots can leave good solutions gathering dust to why Jolene's best deals came when she was willing to walk away, this episode explores what it really takes to earn buyer trust, justify your value, and build credibility before a sale is even on the table.

WHY THIS MATTERS

A great product doesn't guarantee a sale. Education buyers weigh risk, cost, implementation, and student outcomes, and decisions can take months. Jolene believes the relationship should begin as much as 18 months before the purchase.

You can't wait until you need the deal to start earning trust.

🔑 KEY STRATEGIES & MENTAL MODELS

1️⃣ Choose proof over promise. Back up your claims with research and real-world results.

2️⃣ Make pilots purposeful. Define success, secure stakeholder buy-in, and agree on what happens if the pilot works.

3️⃣ Sell value, not price. Help buyers understand the evidence, expertise, and service behind your solution.

4️⃣ Know who influences the purchase. The person using your product may not be the person signing the check.

5️⃣ Build credibility early. Use LinkedIn, relationships, and evidence to earn trust long before buyers are ready.

🎯 WHO THIS EPISODE IS FOR

• Education and EdTech founders selling to schools, districts, and higher education institutions
• Founders offering pilots or struggling to justify premium pricing
• Anyone trying to turn buyer interest into qualified sales conversations

🚀 NEXT STEP

Ask yourself: What's one thing I can do this week to become more credible to my Perfect Client 18 months from now?

Start by identifying the alternatives they're considering. Can you explain how you're different and show evidence that backs up your claims?

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge for practical strategies to help education founders generate leads, close deals, and grow their businesses.

Share this episode with a founder who has a great solution but still needs buyers to believe in it.

Earn the trust before the buying moment.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

You've done the work. You've built the solution. You know you can help.

So why are the right clients still hesitating?

Here's the uncomfortable part: being good at what you do doesn't mean your buyers can see it. And when they're deciding who to trust with their students, their budgets or their business, your word alone might not be enough.

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, shares four stories that show what happens when expertise meets the real world of selling.

From results that give buyers something concrete to believe in to a founder learning the hard way that interest doesn't always mean commitment, these experiences reveal what buyers need to see before they're ready to trust you.

Because your next client might not need another reason to hear you talk about how good you are.

They might need a reason to believe you.

WHY THIS MATTERS

Your perfect client has options. They can choose another company, another solution or another founder who makes them feel more confident about their decision.

Being good at what you do is important, but can a potential buyer see why they should choose you? Can they find evidence that your solution works, understand your expertise and trust your team to deliver?

If not, you could be losing deals to people who aren't necessarily better at what they do. They've simply given buyers more reasons to believe in them.

🔑 KEY STRATEGIES & MENTAL MODELS

1. Proof Over Promises: Show buyers measurable results, not just what you claim you can do.

2. Visibility Builds Trust: Your expertise can't win buyers over if they never see it.

3. Share What You Learn: Owning your mistakes and showing what they taught you can demonstrate good judgment.

4. Make Trust Repeatable: Build a sales process that helps your team earn buyer confidence without you in every conversation.

5. Give Buyers Evidence: Ask yourself what you're showing your perfect client that makes you worthy of their trust.

🎯 WHO THIS EPISODE IS FOR

• Education founders
• EdTech entrepreneurs and leaders
• Consultants and service providers selling into schools
• Founders struggling to turn expertise into leads and sales

🚀 NEXT STEP

Ask yourself one question:

What evidence am I giving my perfect client that I deserve their trust?

Maybe you have results like Anthony. Expertise like Kathryn. Lessons learned like Pamela. Or a growing business that needs to build trust beyond you, like Wayne.

Choose one thing that demonstrates your credibility and make it visible to the people you want to reach.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this episode with an education founder who has the expertise but needs to make it more visible to the people who matter.

Your reputation might get you in the room.

You still need a process for what happens once you're there.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

What did your last conference actually produce?

Not the badge scans or the new LinkedIn connections. A pilot. A contract. A partnership. For most education founders, the honest answer is “not much,” and the reason isn’t the conference. It’s what happened before the trip and after it: no target list, no plan for the conversations, and no system for the follow-up. The 50 business cards end up in a drawer, and the next conference is already on the calendar.

In this episode of EdSales Edge,Josh Chernikoff, founder of the EdSales Revenue Machine, andJohn Gamba, Entrepreneur-in-Residence at Penn GSE, flip the script.

Your credibility walks into the conference 45 days before you do.

Build it early. Identify who you need to reach, start the right conversations before you arrive, and decide what needs to happen after you leave. Work backward from the results you want two months later.

The goal isn't simply to have a productive three days. It's to turn those three days into business opportunities that keep moving long after the conference ends.

WHY THIS MATTERS

“Go to the conference and network” isn't a strategy.

If you don't know what you want to accomplish, who you need to meet, or what happens afterward, you can spend three days being busy without moving your business forward.

🔑 KEY STRATEGIES & MENTAL MODELS

1️⃣ Build the follow-up system before you go.
Know what you'll capture, where you'll track it, and how you'll nurture opportunities after the conference.

2️⃣ Prepare before you arrive.
Research attendees, identify your perfect clients, study competitors, and start conversations before the conference.

3️⃣ Let your credibility walk in before you do.
Use LinkedIn, content, introductions, and visibility to help people understand who you are before you meet.

4️⃣ Give every interaction one job.
Coffee can uncover a problem. Dinner can deepen a relationship. Not every interaction needs a sales pitch.

5️⃣ Be interested, not interesting.
Listen, ask questions, and learn. The conference can reveal gaps in your knowledge and opportunities in your market.

🎯 WHO THIS EPISODE IS FOR

• Education founders
• Teacherpreneurs
• Founders attending conferences for lead generation
• Anyone who wants more from conference attendance than a pile of business cards

🚀 NEXT STEP

Pick your next conference and ask:

“What would have to be true 60 days after this conference for me to call it a huge success?”

Then work backward.

Who do you need to meet? What conversations need to happen? What should people know about you before you arrive? What happens when you get home?

Build the plan before you book the trip.

Want help building your campaign? Text “90 DAYS” to 771-333-4233 for the 90-Day Founder Challenge.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this with an education founder who keeps attending conferences without a clear plan.

The conference is only the beginning. The real work happens before you arrive and long after you leave.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

Your credibility walks into the room before you do.

It can determine whether a buyer replies to your email, accepts your connection, takes your meeting, and eventually buys, or simply moves on.

You could have the right solution and know your market inside and out, but if your buyer hasn't seen enough proof to trust that you're the right person to solve the problem, you can lose the deal before you ever get the chance to make your case.

And if your credibility isn't already visible, another credential, certification, or decade of experience may not close that gap.

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, breaks down what actually makes an education founder credible in a buyer's eyes, and how to give buyers the evidence they need to believe in your expertise before you ever sit across from them.

Because your buyer doesn't need another list of qualifications.

They need proof they can see for themselves. .

WHY THIS MATTERS

Your perfect client needs to experience how you think before they experience your product.

That kind of trust doesn't come from one impressive credential. It builds through lived experience, results, trusted relationships, and the visibility that lets your buyer see all of it.

🔑 KEY STRATEGIES & MENTAL MODELS

1️⃣ Expertise ≠ credibility.

You own your expertise. Your buyer decides your credibility.

2️⃣ Start with the perfect client.

Different buyers need different evidence. Know who you're trying to reach before deciding what they need to see.

3️⃣ Build three kinds of credibility.

Lived. Proof. Borrowed. Then use visibility to multiply all three.

4️⃣ Claim vs. evidence.

“We understand district leaders” is a claim. Tell a story that makes them think, “Wow, they really understand district leaders.”

5️⃣ Make earned credibility visible.

The problem may not be that you need more credibility. It may be that the credibility you've already earned is invisible.

🎯 WHO THIS EPISODE IS FOR

• Education founders
• Teacherpreneurs
• EdTech leaders
• Consultants selling into schools
• Founders struggling to turn expertise into qualified leads

🚀 NEXT STEP

Take 10 minutes.

Google yourself. Open your LinkedIn profile. Open your website.

Pretend you're your perfect client.

Ask: “What do I find here that gives me a reason to trust this person?”

Maybe you've spent 20 years inside schools but never tell those stories.

Maybe you spoke at a respected conference. Don't just post the picture. Teach what you taught.

Make the evidence visible.

If you want help doing it, text "90 DAYS" to 771-333-4233 for the 90-Day Founder Challenge.

Teacher-founders: limited 1:1 planning sessions are open, too.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this with an education founder who keeps adding credentials instead of making their proof visible.

Your expertise is yours.

Your credibility belongs to the buyer.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

Practice your sales message too little and you stumble through it.

Practice it too much and you worry you’ll sound like a robot.

So where’s the line?

It’s not about how many times you’ve said it. It’s about what you do once the conversation starts.

In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, and John Gamba, Entrepreneur-in-Residence at Penn GSE, explore the difference between repetition and memorization—and why knowing your message cold can actually make you more human in a sales conversation.

Athletes don’t invent the fundamentals in the middle of the game. Musicians don’t figure out the chords during the concert.

The reps happen before the performance so you can be present when it matters.

Education sales works the same way.

Know the message. Practice the proof. Then listen.

Because repetition doesn’t make you robotic.

Stopping listening does.

WHY THIS MATTERS

You finally get the meeting.

Then someone asks what you do and your 30-second answer becomes three minutes.

Or you stick so closely to the pitch you prepared that you miss what the buyer is actually telling you.

That’s the problem.

Knowing your message creates freedom. You can pause. Ask questions. Read the room. Listen.

Your message stays consistent.

Your delivery adapts.

🔑 KEY STRATEGIES & MENTAL MODELS

1️⃣ Memorize the core, not the conversation.

Know your headline, value proposition, proof points, and key stories. Leave room for the conversation.

2️⃣ Vary the delivery, not the value.

How you say it can change. The value you communicate shouldn’t.

3️⃣ Pause before you apply.

Deliver what you know. Then stop. Listen. Ask. The pause moves you from your message to their problem.

4️⃣ Practice relaxed concentration.

Know what you came to say without becoming so focused on saying it that you miss what’s happening in the room.

5️⃣ Be interested, not interesting.

Don’t prove how much you know. Ask sharper questions, listen closely, and show the buyer you heard them.

🎯 WHO THIS EPISODE IS FOR

• Education founders
• Teacherpreneurs
• EdTech leaders selling into schools
• Founders preparing for buyer meetings
• Anyone who wants to sound confident without sounding scripted

🚀 NEXT STEP

Before your next sales conversation, explain what you do without your website, deck, or notes.

Can you communicate the value without searching for the words?

If not, you probably don’t need a better pitch.

You need more reps.

Once you know it cold, stop rehearsing and start listening.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and send this episode to an education founder who thinks practicing their message will make them sound rehearsed.

Repetition builds confidence.

Listening keeps it human.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

A superintendent is not a lead generation strategy. Neither is a curriculum director, a principal, or a dean.

Those titles tell you who someone is. They don't tell you why they'd care about your solution right now.

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, compares two superintendents who look identical on paper.

Superintendent A just renewed a three-year contract, so nobody's pushing for a new solution. Superintendent B's board just made chronic absenteeism a top priority, with funding attached and pressure to show results.

Same title, completely different lead.

Josh calls this the snow shovel test: a Phoenix homeowner and a Boston homeowner can technically buy the same shovel, but only one has twelve inches of snow coming tomorrow.

The product didn't change. The situation did.

Your perfect client isn't just a person. They're a person in a moment.

WHY THIS MATTERS

Education sales runs on long cycles, boards, budgets, and competing priorities. Timing isn't a detail in your targeting, it is the targeting.

Title targeting gives you a database. Buying situation targeting gives you a lead list.

MediatorSpark, which helps middle schools build peer mediation programs, is a good example.

Every principal fits the title, but the real lead is the school where discipline referrals are climbing and culture just became a stated priority.

THE BUYING SITUATION TEST

1️⃣ What changed? New leader, funding, priority, requirement, deadline, or failed initiative.

2️⃣ Who owns the problem? Not the biggest title, the person accountable for the outcome.

3️⃣ Is there evidence they care? Strategic plans, funding, hiring, board discussions, RFPs.

4️⃣ Can you find the pattern? Look at what was true right before your best customers bought, then look for it again.

WHO THIS EPISODE IS FOR

Education founders trying to generate better leads.

Teacherpreneurs selling into schools and districts.

EdTech leaders leaning too hard on job titles.

Sales teams struggling with cold outreach.

🚀 NEXT STEP

Take the first 25 names on your prospect list.

Beside each, write "why now?" What changed, who owns the problem, what evidence shows they care.

"They're a superintendent" isn't an answer.

Then look at your five strongest customers and ask it backward: what was true right before they bought? Compare the answers, look for the pattern.

Want help turning that pattern into a plan?

Text "90 DAYS" to 771-333-4233 for the 90-Day Founder Challenge.

Teacher-founders: limited 1:1 planning sessions are available.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this with a founder building lists of people who could buy but don't yet have a reason to care.

Don't just find the person.

Find the moment.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

You’re afraid that getting too specific about your perfect client will shrink your market.

But what if it does the opposite?

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine and John Gamba, Entrepreneur-in-Residence at Penn GSE challenge education founders to rethink the way they define their target customer—and why “ideal client” may not be specific enough.

“Schools” is a market. “K-12 schools” is more specific. But what happens when you keep narrowing the target until you know exactly who you want to serve, what problem they have, and why your solution fits?

That’s where “perfect client” comes in.

The goal isn't to find a flawless customer. It’s to find a business fit so clear that you can describe your best-fit customer so clearly that your sales team knows exactly who to pursue—and who not to.

And getting that specific can do more than sharpen your targeting. It creates repetition.

You start seeing the same problems. Hearing the same language. Refining the same message. Building credibility with the same type of buyer.

You stop reinventing your sales process every time.

WHY THIS MATTERS

Many education founders believe that niching down means giving up growth.

A narrow target can actually create a stronger path to growth because specificity makes it easier to understand your customer, repeat what works, deliver measurable value, earn renewals, and build credibility in a market.

You don't need to sell to everyone.

You need to know who you can help best.

KEY STRATEGIES & MENTAL MODELS

1️⃣ Perfect client = a specific target.
Don't stop at a broad market. Get specific about the customer, problem, environment, and outcome so your message speaks directly to the people you want to reach.

2️⃣ Specificity creates repetition—and repetition creates confidence.
Serving similar customers helps you recognize patterns, sharpen your message, and improve your sales process without becoming robotic.

3️⃣ Narrow doesn't mean small.
A focused target can become a center of excellence: deliver great results, earn renewals, generate referrals, and expand into surrounding opportunities.

WHO THIS EPISODE IS FOR

Education founders
Teacherpreneurs
Education sales teams
Founders struggling to define their target market

NEXT STEP

Look at your current “ideal client.”

Now make it more specific.

Can you clearly describe:

• Who they are
• What problem they’re trying to solve
• When that problem becomes urgent
• Why your solution is the right fit

If your answers are still broad, your target probably is too.

Then text “90 DAYS” to 771-333-4233 to get the 90-Day Founder Challenge.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this episode with an education founder who is trying to sell to everyone.

Get specific. Find your target. Repeat what works.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

What if your best customer isn't actually your perfect client?

Josh Chernikoff learned this lesson while building his second business, an afterschool enrichment company.

At first, he pursued schools that didn't have enrichment programs. They wanted a program—but they didn't necessarily need one. The difference changed everything.

When Josh started working with schools that genuinely needed a program, he understood their problems, spoke their language, and could see the world from their perspective.

That became his version of the “clean windows” idea: when you know exactly who you're serving, you can see the problem clearly because you're looking through the same window.

Now he's seeing the same pattern with education founders.

The right clients don't just need what you sell. They believe you can help, they're ready to act, and they're part of a pattern you can serve repeatedly.

That's why Josh asks one uncomfortable question:

“If 100 more customers exactly like this showed up tomorrow, would you be excited—or overwhelmed?”

WHY THIS MATTERS

Education founders often confuse a customer who worked with a customer they should pursue repeatedly.

A customer can need your solution and still not be ready to buy. They can love your product and still require enormous effort to close or serve.

Your perfect client is different.

They're part of a pattern.

They have the problem, enough urgency to act, the authority or access to make a decision, the resources and willingness to move.

When you find that pattern, sales becomes easier to focus, messaging becomes clearer, and growth becomes more repeatable.

THE PERFECT CLIENT TEST

1️⃣ Ask: “Would I want 100 more?”
Look beyond revenue. Would you want 100 more with the same needs and demands?

2️⃣ Separate need from readiness.
Need isn't enough. Look for urgency, authority, resources, and willingness to act.

3️⃣ Find the pattern behind the yes.
Study what your best customers share—and build your acquisition around it.

🎯 WHO THIS EPISODE IS FOR

Education founders figuring out who they should pursue.

Teacherpreneurs worried that getting specific means giving up opportunities.

EdTech leaders constantly reinventing how they serve customers.

Founders unsure whether their best customers represent a repeatable growth opportunity.

🚀 NEXT STEP

Pull up your best customers.

Don't start with revenue.

Start with a question:

“Which one would I actually want 100 more of?”

If you're not sure who you should spend the next 90 days pursuing, text “90 DAYS” to 771-333-4233.

You'll get the 90-Day Founder Challenge—a practical framework for deciding what deserves your attention next.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this episode with an education founder who may be chasing great customers instead of the right customers.

One great customer proves you can make something work.

The right pattern shows you what to build around.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

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.

The Department of Education just released new guidance on responsible technology use.

And buried inside it?

Five questions every education founder should probably be able to answer before walking into their next sales conversation.

That’s why, 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 the belief that having a great education solution is enough to earn the sale.

The guidance asks: What problem does it solve? Who should use it? When? For how long? And what evidence proves it improves learning?

Those aren’t just policy questions.

They’re sales questions.

WHY THIS MATTERS

You see possibility in your solution, but your buyer sees another decision they may have to defend.

So when you say, “This works for everyone,” you hear opportunity while they hear risk.

Your buyer needs enough evidence to create confidence of their own.

KEY STRATEGIES & MENTAL MODELS

1️⃣ Stop hiding behind what you built

Your school buyer cares less about what your solution contains than the painful problem it removes.

2️⃣ Have the courage to exclude

Saying who your solution is not for can make the right school buyer trust you faster.

3️⃣ Stop confusing usage with impact

More minutes or activity mean nothing if you cannot connect them to a meaningful result.

4️⃣ Bring proof they can repeat

Your evidence does not need to be enormous, but it must give your buyer something credible to carry into the next meeting.

5️⃣ Make yourself easier to defend

The sale gets stronger when your champion can explain why choosing you is safer than doing nothing.

🎯 WHO THIS EPISODE IS FOR

Education founders who know their solution works but struggle to prove it

Teacherpreneurs turning classroom expertise into buyer confidence

Education business leaders selling into cautious schools and districts

Founders tired of hearing “this looks great” without getting the yes

🚀 NEXT STEP

Pull up the sales deck you used in your last school conversation and underline every promise you made.

Then ask yourself:

“If my buyer had to defend choosing me tomorrow without me in the room, what would they actually have to say?”

If the answer is just a list of features, you are in trouble.

Ready to change the conversation? 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 share this episode with an education founder who keeps getting interest from school leaders but cannot turn it into a confident yes.

You do not win because you believe harder.

You win when the buyer has enough reason to believe with you.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

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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 what exactly are you bringing to the sale?

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, challenges education founders and teacherpreneurs to rethink how they use AI in their sales process.

This isn't anti-AI — Josh uses it every day. The problem is convenience quietly making strategic decisions for you.

When AI handles research, outreach, discovery, prep, proposals, and follow-up, founders get efficient while getting less human.

In education sales, that's a dangerous trade.

Buyers don't purchase your prompts. They buy your experience, judgment, and understanding of their world.

AI organizes information. It can't develop wisdom.

The advantage is shifting from information to interpretation.

Everyone can pull the same district data. Founders and teacherpreneurs who win understand what it means for the people across the table.

WHY THIS MATTERS

Saved time shouldn't become fifty more automated emails. It should become more conversations, school visits, and deeper relationships.

The sale still starts when the buyer talks — where curiosity, empathy, and reading what isn't said take over.

KEY STRATEGIES & MENTAL MODELS

1️⃣ AI does the work. You do the thinking.

Let it draft, research, and organize. Keep the judgment yours.

2️⃣ AI preps the conversation. It doesn't have it.

Once the buyer's talking, your job is to listen — not read a script.

3️⃣ Information is cheap now. Interpretation isn't.

AI tells you what a district says. You figure out what it means.

4️⃣ Use AI to argue with your thinking, not confirm it.

Don't ask it to write the email. Ask what it's missing.

5️⃣ AI should buy you time, not just volume.

Use it to get back in the room — not to send more emails.

🎯 WHO THIS EPISODE IS FOR

• Education founders
• Teacherpreneurs
• Education sales teams
• Anyone wondering where AI belongs in the sales process

NEXT STEP

Look at every place you've used AI over the past seven days.

Then ask yourself one question:

"Did AI replace work, or did it replace thinking?"

If it replaced work, keep going.

If it replaced thinking, take that responsibility back.

Ready to put that into a plan? 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 episode to an education founder or a teacherpreneur who's using AI to sell faster but needs a reminder not to lose the human part of the sale.

Use AI for the work.

Don't use AI to avoid the relationship.

Because education will always be a people business.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

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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 Revenue Machine
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

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Get closer to the conversations, strategies, and operators inside the ecosystem:
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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 happens.

The very person who built the solution disappears behind logos, fonts, taglines, company pages and carefully polished messaging.

Meanwhile, buyers are asking a much simpler question:

"Who are you, and why should I trust you?"

That's where deals are won or lost.

You don't need a better logo. You need more conversations. You need more trust. You need more sales.

Logos matter. Taglines matter. Brand recognition matters. But those things become more important as the business grows. Early on, people are buying the person behind the business.

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, explains why so many education founders overcomplicate personal branding, hide behind company pages, and miss the simple truth: people buy people.

WHY THIS MATTERS

Education founders overthink personal branding all the time. They spend months worrying about logos, messaging, websites, and company pages while ignoring the one thing buyers are actually looking for: a person they can trust.

Early on, people buy people.

Your company can deliver the promise, but the founder is often the reason the conversation starts in the first place.

The goal isn't to become famous. The goal is to become known, trusted, and remembered.

🔑 KEY STRATEGIES & MENTAL MODELS

1️⃣ Use the founder to build trust. Use the company to deliver the promise.

Your business shouldn't depend on you forever, but the market shouldn't have to discover it without you today.

2️⃣ Stop posting like a press release.

Announcements teach people about your company. Stories teach people about you.

3️⃣ Show something real.

People connect with honesty, not perfection.

4️⃣ Visibility isn't a sales system. It's the entrance to one.

Story. Trust. Conversation. Sales process.

Every story needs a next step: a webinar, a newsletter, a clear invitation forward.

5️⃣ Give people something to act on, not just read.

A practical next step makes you useful long before you're ever hired.

🎯 WHO THIS EPISODE IS FOR

• Education founders
• Teacherpreneurs
• EdTech leaders
• Consultants selling into schools
• Anyone building a business that extends beyond the founder

🚀 NEXT STEP

Open your last 10 LinkedIn posts and ignore the likes. Ask yourself this question instead:

"How many show something I know, something I've experienced, something I believe, or something my buyer should do next?"

Then text "90 DAYS" to 771-333-4233.

Get the 90-Day Founder Challenge — a practical framework for your next 90 days.

Teacher-founders: a few 1:1 planning sessions are still open.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and send this episode to an education founder who's hiding behind the company page instead of standing in front of it.

The company may deliver the solution.

But the founder opens the door.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

"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 conversation. Usually after showing hard proof that the thing works.

And that's exactly what makes it sting.

Most education founders think they lost to another company.

They didn't.

In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, and John Gamba, Entrepreneur-in-Residence at Penn GSE, dig into one of the hardest truths in school sales:

You're not competing with a rival product. You're competing with familiarity, routine, a packed calendar, a tight budget, and the plain fact that change feels risky even when it's the right call.

School leaders aren't only asking if your solution is better. They're asking if the disruption of switching is worth it.

That's a completely different question — and most pitches never answer it.

WHY THIS MATTERS

Education founders sell what's possible.

Buyers quietly calculate what it will cost them to get there.

While education founders are painting the upside, school leaders are running the numbers on training, rollout, pushback, and who takes the blame if it flops.

That's why "good enough" keeps beating "better."

Not because leaders don't want something better.

Because standing still still feels like the safer bet.

The founders who get this stop pushing harder.

They start asking sharper questions.

KEY STRATEGIES & MENTAL MODELS

1️⃣ You're not losing to a competitor.

You're losing to how comfortable the current system already feels.

2️⃣ Features get nods. Outcomes get signatures.

School leaders remember what changed, not what the dashboard looks like.

3️⃣ Ask, don't argue.

A sharp question opens more doors than the strongest pitch ever will.

4️⃣ Put a price on standing still.

If staying the same looks free, changing will always look expensive by comparison.

5️⃣ Find whose job gets easier.

Your loudest champion is the person whose daily work your solution actually fixes.

🎯 WHO THIS EPISODE IS FOR

• Education founders
• Teacherpreneurs
• EdTech leaders
• Consultants selling into schools
• Anyone trying to move a system that doesn't want to move

🚀 NEXT STEP

Pull up the last deal that went quiet.

Skip the usual question — "how do I push this forward" — and ask a harder one instead:

"What am I actually asking this buyer to give up?"

Text "90 DAYS" to 771-333-4233.

Get the 90-Day Founder Challenge — a practical framework for your next 90 days.

Teacher-founders: a few 1:1 planning sessions are still open.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and send this to an education founder who's tired of hearing "we'll stick with what we have."

Because the real obstacle was never the competition.

It was always familiarity.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

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 founders, the answer seems obvious: hire a salesperson, find a reseller, or bring in someone with the right connections to get your solution to schools.

But there's a problem with handing off sales too soon.

You may be trying to delegate something you haven't learned yet.

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine explores why founder-led sales isn't about becoming a salesperson forever. It's about learning your market well enough to understand who buys, why they buy, what problems they urgently need solved, and what makes them say yes.

Josh shares how Michael Dell learned to pay attention to who was buying newspaper subscriptions—and discovered patterns that helped him target the right people.

That's the real purpose of founder-led sales: market research, discovery, and pattern recognition. Every conversation reveals what resonates, which objections keep appearing, and what moves buyers forward.

A salesperson can't discover your market for you. You have to learn those things first.

Because if you don't, you aren't really delegating sales.

You're delegating confusion.

WHY THIS MATTERS

Teacherpreneurs and education founders don't need to become lifelong salespeople. But they do need enough firsthand experience to understand their buyers before handing the process to someone else.

When you know your ideal client, their problem, objections, and buying triggers, you can build a repeatable process and eventually scale it.

The goal isn't to sell forever. It's to learn enough to teach someone else.

KEY STRATEGIES

1️⃣ Founder-Led Sales Is Market Research
Early sales conversations reveal what your market actually cares about.

2️⃣ Learn the Buyer Before Building the Sales Machine
Know your perfect client, their problem, and why your solution matters.

3️⃣ Don't Mistake a Sales Problem for a Positioning Problem
Weak sales may point to targeting, messaging, positioning, or offer problems.

4️⃣ Get Enough Reps to Know What Works
You need enough experience to recognize patterns and build a process.

5️⃣ Earn the Right to Delegate
Before handing off sales, make sure you're giving someone a system—not asking them to figure out your market.

WHO THIS EPISODE IS FOR

Teacherpreneurs and education founders preparing to scale
Founders considering their first sales hire
Education companies exploring sales partnerships

NEXT STEP

Ask yourself:

Am I delegating a proven sales system—or asking someone else to figure out my market?

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 available.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this episode with a teacherpreneur or education founder who's ready to scale—but needs to learn the market first.

You don't have to sell forever. Before you hand off the sale, understand the buyer.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

AI has made it faster than ever to find prospects, research school districts, write personalized emails, create LinkedIn messages, and build follow-up sequences.

Education founders can now do in minutes what used to take hours. Yet many are still hearing the same thing: silence.

The problem isn't AI. It's expecting AI to do the one job it was never meant to do—build relationships.

In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, and John Gamba, Entrepreneur-in-Residence at Penn GSE, explore how education companies and teacherpreneurs can use AI to generate more leads without sounding like AI.

Using Lionel Messi's preparation for the World Cup as a powerful analogy, they explain why AI should be your equipment—not the player.

Learn how to use AI to earn more replies by strengthening research, sharpening your messaging, and keeping trust and human judgment at the center of every sales conversation.

WHY THIS MATTERS

AI has lowered the barrier to creating outreach.

It hasn't lowered the barrier to earning trust.

Buyers are getting better at recognizing outreach that feels automated instead of authentic.

The founders who stand out won't be the ones using the most AI. They'll be the ones using AI to strengthen genuine human relationships.

KEY STRATEGIES & MENTAL MODELS

1️⃣ Let AI Be the Equipment, Not the Player

Use AI to research, organize, analyze, and prepare. Human judgment is still responsible for reading the situation, asking better questions, and building trust.

2️⃣ Solve the Foundation Before the Automation

The best prompt can't fix an unclear offer or an undefined ideal customer. Strong positioning comes before stronger AI workflows.

3️⃣ Personalization Starts With Curiosity

Instead of making assumptions about buyers, use research to ask thoughtful questions that open meaningful conversations.

4️⃣ Automate the Work, Not the Relationship

AI can accelerate follow-ups and proposals, but founders should remain the final voice.

5️⃣ Better Conversations Beat More Outreach

The goal isn't simply to send more emails. It's to create messages that deserve a response because they're relevant, thoughtful, and human.

🎯 WHO THIS EPISODE IS FOR

• Education founders using AI to support sales and marketing
• Teacherpreneurs building stronger outreach strategies
• EdTech sales teams looking to improve response rates
• Founders balancing automation with authentic relationship-building
• Anyone selling into K-12 education

🚀 NEXT STEP

Ask yourself:

Is AI helping you build more relationships... or simply send more messages?

Join Josh's upcoming masterclass and learn how to turn more conversations into paying clients.

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 available.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this episode with a founder who's using AI to save time—but wants to make sure it never replaces trust.

The future of education sales belongs to founders who combine smarter technology with stronger relationships.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

Many teacherpreneurs and education founders work hard to build credibility.

They earn certifications, highlight partnerships, showcase awards, and perfect their product.

Yet sales conversations still stall. Buyers understand what they built, but never connect with why they built it.

Without that connection, trust takes longer to build, sales conversations lose momentum, and revenue becomes harder to generate.

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, sits down with Peter Mills, founder of Recess Reset, to explore one of the biggest mindset shifts founders face: moving from hiding behind credentials to leading with authentic connection.

Peter shares why he initially avoided telling his unconventional story—from professional dancer to living in India before founding an education company—and how embracing that story transformed his messaging, strengthened conversations with school leaders, and built deeper trust with buyers.

This isn't about personal branding. It's about building trust that leads to better sales conversations and revenue growth.

WHY THIS MATTERS

Whether you're launching, searching for traction, or scaling, trust drives revenue.

Education buyers don't buy products based on features alone. They buy when they trust the founder and believe in the problem being solved.

Your story helps create that trust.

🔑 KEY STRATEGIES & MENTAL MODELS

1️⃣ Stories Create Trust
Credentials may open the door, but authentic stories help buyers remember—and trust—you.

2️⃣ Make Buyers Care Before You Try to Impress Them
The strongest messaging helps school leaders see why the problem matters before highlighting achievements.

3️⃣ Connect Your Story to Your Customer's Reality
The best founder stories aren't biographies. They directly explain the problem your solution was built to solve.

4️⃣ Build Familiarity, Not Just Differentiation
Connecting your solution to tools educators already know makes new ideas easier to understand and adopt.

5️⃣ Lead Every Conversation with Purpose
A simple story, a relatable example, and a clear plan create stronger sales conversations than a product pitch alone.

🎯 WHO THIS EPISODE IS FOR

• Teacherpreneurs preparing to launch an education business
• Education founders struggling to gain traction
• Founders refining their messaging and positioning
• Education companies building trust with school leaders

🚀 NEXT STEP

Ask yourself:

Are buyers remembering my credentials—or remembering why I care?

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 available.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this episode with a founder who's been hiding behind their résumé instead of sharing the story that makes their business matter.

The strongest education businesses grow when buyers trust the founder before they trust the product.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

Every teacherpreneur and education founder starts with the same belief.

If I create something that genuinely helps students, schools will want it.

It sounds reasonable.

But education businesses don't grow on value alone.

They grow when buyers trust the founder, partners strengthen credibility, and the right people help create momentum around the solution.

That's the real conversation in this episode.

Originally recorded live at IFE in Monterrey, Mexico in April 2025, Josh Chernikoff, founder of the EdSales Revenue Machine, sits down with Beatriz Guillen, Executive Director of The Resource Foundation. While the conversation explores philanthropy and education across Latin America, the lessons reach far beyond one region.

Together, they explore a question every education founder eventually faces:

What helps great education businesses become businesses that actually grow?

The answer isn't another feature.

It isn't better marketing.

It's learning to think beyond the solution itself.

From partnerships and buyer confidence to credibility and long-term ecosystem building, this conversation challenges founders to stop asking, "How do I sell this?" and start asking, "What needs to exist before buyers are ready to say yes?”

Why This Matters

Whether you're preparing to launch or already selling into schools, education buyers rarely make decisions on value alone.

They look for evidence.

They look for credibility.

They look for trusted partners.

Founders who understand that build momentum faster, create stronger relationships, and give great solutions a better chance to succeed.

🔑 Key Strategies & Mental Models

1️⃣ Build an Ecosystem, Not Just a Business
The strongest education companies don't grow alone. They intentionally build relationships that create momentum.

2️⃣ Credibility Comes Before Adoption
Evidence reduces risk. Buyers need confidence before they make commitments.

3️⃣ Partnerships Beat Isolation
Strategic partners often create opportunities that marketing alone never will.

4️⃣ Solve for the Buyer, Not Just the User
Great products help students. Great businesses also make buying decisions easier.

🎯 Who This Episode Is For

• Teacherpreneurs building their first education business
• Founders selling into schools or districts
• Education companies seeking strategic partnerships
• Operators navigating long education sales cycles

🚀 Next Step

Ask yourself: Who needs to believe in my business before my next customer says yes?

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 available.

🔁 Subscribe & Share

If this episode changed how you think about growing an education business, subscribe and share it with another founder.

The strongest education businesses are built through relationships, not just great products.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

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. The hard part is figuring out who needs it, how to talk about it, and how to create demand around it.

In this episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine (previously EdSales Elevation Experience) sits down with Grace Pokela, founder of The Lesson Laboratory. Grace built a digital curriculum and instructional model that helped students become active investigators rather than passive learners. The results were real. But like many teacherpreneurs and education founders, she discovered that expertise alone doesn't create a business.

The conversation explores the shift from educator to entrepreneur. From identifying the right buyer to building confidence, developing a signature solution, and learning founder-led sales, Grace shares what it takes to build a foundation before chasing scale.

This isn't a conversation about curriculum. It's a conversation about what happens when an educator decides to build a business.

WHY THIS MATTERS

Many teacherpreneurs spend years mastering instruction and very little time learning positioning, sales, and customer discovery.

The result is often frustration. Strong solutions struggle because the founder assumes results will create demand.

They don't.

Growth gets easier when buyers understand exactly who you help, what problem you solve, and why it matters.

🔑 KEY STRATEGIES & MENTAL MODELS

1️⃣ A Breakthrough Is Not a Business

A solution can be effective and still struggle in the market. Growth begins when founders learn how to position and sell that solution.

2️⃣ Clarity Creates Traction

The clearer you are about the problem you solve and who you solve it for, the easier it becomes to generate opportunities.

3️⃣ Find the Buyer Closest to the Pain

The person with the budget is not always the person who feels the problem most deeply. Understanding that difference changes your sales strategy.

4️⃣ Confidence Is Built Through Action

Founder confidence doesn't come from motivation. It comes from customer conversations, market feedback, and repeated execution.

5️⃣ Build the Foundation Before You Scale

Positioning, messaging, credibility, and pipeline development are not growth accelerators. They are growth prerequisites.

🎯 WHO THIS EPISODE IS FOR

Teacherpreneurs turning expertise into a business

Education founders seeking product-market fit

Educators building their first revenue engine

Teams struggling to define their ideal customer

Founders looking to improve positioning

🚀 NEXT STEP

Ask yourself:

Have I built a business, or have I only built a solution?

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 available.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this with a teacherpreneur who's trying to scale before building a foundation.

Growth gets expensive when clarity is missing.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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

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, and improve the business while the pace of the school year slows down.

But the lesson extends beyond teacherpreneurs. Every education business owner faces the same challenge: using quieter seasons to strengthen the business instead of simply reacting to it.

In this live episode of EdSales Edge, Josh Chernikoff, founder of the EdSales Revenue Machine, and John Gamba, Entrepreneur-in-Residence at Penn GSE, discuss why summer is one of the most important seasons for teacherpreneurs. Not because schools are buying more, but because founders finally have space to think, plan, refine, and prepare for what's next.

The conversation explores common mistakes: forcing offers that no longer match buyer behavior, disappearing completely, or staying trapped in delivery work without improving the business itself.

Josh and John share a practical framework for using summer intentionally. From clarifying offers and understanding buyer priorities to creating a focused 90-day plan, this conversation is about building a stronger fall before it arrives.

WHY THIS MATTERS

Growth problems don’t start when sales slow down.
They start when founders stop checking what’s actually working.

Most education businesses enter a new school year carrying the same problems: unclear messaging, weak positioning, inconsistent outreach, and broken sales flow.

Summer is the window to fix it—before those issues get expensive.

The founders who grow aren’t always the busiest.

They’re the ones who use quiet seasons to sharpen their message, deepen relationships, and prepare for the next buying cycle.

KEY STRATEGIES & MENTAL MODELS

1️⃣ Sell Where Demand Is Real

Focus on buyers already showing interest instead of forcing conversations that aren't moving.

2️⃣ Clarify the Transformation

Be able to explain who you help, how you help, and what outcome you create. If buyers can't repeat it back, your message isn't clear enough.

3️⃣ Build a 90-Day Plan

Skip the giant annual strategy document. Focus on the next ninety days. Clear priorities create momentum.

4️⃣ Work on the Business

Use summer to refine your offer, strengthen outreach, revisit goals, and prepare for the next selling season.

5️⃣ Understand What Buyers Care About

Strong founders focus on the problems buyers are actively trying to solve. Summer is a great time to do that research.

WHO THIS EPISODE IS FOR

• Teacherpreneurs building education businesses
• Educators turning classroom expertise into a business
• Founders struggling with sales consistency
• Operators building repeatable growth systems

🚀 NEXT STEP

Ask yourself:

If the fall started tomorrow, would your business be ready?

The next season is built before it arrives.

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 available.

🔁 SUBSCRIBE & SHARE

Follow EdSales Edge and share this with a founder who plans to "figure it out" in September.

The next school year gets built long before the first day of school.

Connect with Josh Chernikoff

Founder, Edsales Revenue Machine
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