What Happens when the funding dries up.
Season 1, Episode 1
​
What happens when the Funding Dries Up?
Ever had a stretch where you knew you were good at what you do, but the money just... stopped coming in?
I sat down with a founder recently who went seven months without closing a deal.
Not because he wasn't talented—he's a former teacher and principal, brilliant at what he did. But 85% of his revenue was tied to Title funding, and when schools got nervous about whether that money would come through, everything froze.
The calls kept happening. The interest was there. But nobody was buying.
Here's what struck me about our conversation: he wasn't embarrassed to admit that closing sales didn't come naturally to him. He just knew he had to figure it out or his business was done.
I'm guessing some of you have been there, too. Where you're great at the work itself, but there's this other part of running a business that just doesn't click.
That's why I'm starting "The Shift: Insights from The Founder's Table."
Honest conversations with founders about the moments that almost broke them—and what they did to turn it around.
#TheShift #FoundersTable #EdTech #K12 #Entrepreneurship #FounderStories #SalesStrategy
From $8,000 to Six Figures.
​
Season 1, Episode 2
That's the shift this founder made—and it wasn't about working harder or finding more clients.
When we first started working together, their biggest sale was $8,000. Most deals were in the $2,000 to $4,000 range—good money, but a lot of hustle for not much return.
Now? Their smallest deals are $25,000. Many are pushing six figures.
What changed? They stopped competing on price. They started working with clients who actually valued what they bring to the table.
They're working with fewer clients but making more money. Better clients, better work, better business.
Too many founders I talk to are talented, experienced, doing great work—but they're exhausted because they're taking on too many small deals to keep the lights on.
Sometimes you don't need more clients. You just need the right ones.
Episode 2 of "The Shift: Insights from The Founder's Table"
#TheShift #FoundersTable #EdTech #Entrepreneurship
What finally worked.
​
Season 1, Episode 3
"I worked with two sales consultants before you, Mike. Both were great at what they do. But neither had ever sold to a school."
This founder told me they spent money on ads—Google, Meta, all of it. Got a ton of email contacts. But almost none of them turned into sales.
The problem wasn't the consultants. They just didn't get how different K-12 is. The funding, the timelines, the decision-making process—it's a whole other world.
So we shifted the approach. Stopped trying to catch everyone and started focusing on finding the right people where they already are.
The result? Better conversations. Better leads. And sales that felt natural, not some rigid process.
The founder told me it made everything "comfortable and casual" instead of exhausting.
I think this happens a lot. You hire someone who's good at their job but doesn't understand your industry.
They tell you to spend more on ads. You get a bunch of noise but nothing that sticks.
Sometimes it's not about doing more. It's about doing what actually works.
Episode 3 of "The Shift: Insights from The Founder's Table"
#TheShift #FoundersTable #EdTech #K12Sales #Entrepreneurship
When I Stopped Being The Expert
​
Season 1, Episode 4
This founder spent 20 years in education. Former principal. Really understood K-12. But closing deals? That was tough.
They knew their stuff, but school leaders weren't responding.
The issue wasn't their knowledge. It was their approach.
When you reach out to school leaders like everyone else does, you disappear. You're just another email.
We changed that.
Instead of leading with what they were selling, they led with understanding.
Instead of being the expert, they became a partner.
The message went from "here's what I can do for you" to "I've been where you are. I can help if it makes sense."
That made all the difference. The right people started responding. Conversations felt real.
School leaders don't need another vendor. They need someone who gets what they're going through and genuinely wants to help.
That's what this founder became.
Episode 4 of "The Shift: Insights from The Founder's Table"
#TheShift #FoundersTable #EdTech #K12Sales #Entrepreneurship
From Skeptical to Saying Yes
​
Season 1, Episode 5
This Founder gets 10-15 cold LinkedIn messages a day. They delete almost all of them.
But they responded to mine.
Why?
They told me they were skeptical of anyone reaching out cold. But when they read my message, something felt different. It wasn't pushy. It wasn't selling. It just felt human.
They checked out my profile. Looked through my content. Still skeptical, but curious enough to take a call.
On that first call, I wasn't trying to close them. I was trying to figure out if we were a good fit for each other. That's not how most sales calls go.
Most cold outreach feels transactional. "Here's my 12-step program. Pay this much money. You'll make 10 times more sales in a month." That's a gimmick.
This Founder said my approach felt genuine. And that mattered because education is such a human profession. They wanted to work with someone they could actually learn from and grow with, not someone making impossible promises.
Six months later, their bottom line reflects that decision. They've closed their biggest deals ever by focusing on value instead of price. Not racing to the bottom to be the cheapest option, but showing school leaders how they can actually solve their problems.
When you lead with value and genuinely care about helping someone reach their goal, the money conversation gets easier. It stops being about cost and starts being about the solution.
Episode 5 of "The Shift: Insights from The Founder's Table"
#TheShift #FoundersTable #EdTech #K12Sales #Entrepreneurship
When I Finally Understood My Value
​
Season 1, Episode 6
This founder doubled their prices on the same day of a sales call.
The client had no idea. They agreed right away.
Why? Because the client wasn't buying a service. They were buying the result they'd get.
That's the shift. When you focus on the value you bring instead of the transaction, the price conversation changes completely.
Before this, the founder felt nervous before every sales call. They said they felt "slimy" and "too salesish." Like they were trying to push something on people who didn't want it.
Now? Sales calls feel like talking to a friend. Natural. Comfortable. No pressure.
The hardest part wasn't learning a new process. It was changing their mindset. They had to stop thinking "I need to make this sale" and start thinking "I'm offering something that can help them reach their goal."
That took work. Reflection. Feedback. But once it clicked, everything changed.
They stopped selling a service and started offering a solution. And if someone didn't want it? That was fine. No pressure. Just a conversation.
That shift took the pressure off, which made them way more effective at actually closing deals.
I think many founders struggle with this. You know your service is valuable, but you still feel uncomfortable talking about money. You undercharge because you're worried people won't say yes.
But when you truly understand the value you bring, everything gets easier. You stop apologizing for your price. You start showing up confident.
Episode 6 of "The Shift: Insights from The Founder's Table"
#TheShift #FoundersTable #EdTech #K12Sales #Entrepreneurship
I Was Playing the Wrong Game
​
Season 1, Episode 7
This founder used to spend hours every day hunting for leads.
Why? Because their deals were small. Between $2,000 and $8,000. They needed a lot of them just to stay afloat.
Then they shifted to selling on value instead of price. Their deals went to $35,000 and up.
That changed everything. Not just the revenue. The time.
When you're closing bigger deals, you don't need as many of them. That freed up space to actually think. To listen to their current clients. To get feedback. To build new services.
They developed a whole new offering while we've been working together. Already making sales on it.
If they were still chasing every small lead just to keep the business going, that wouldn't have happened. They'd still be stuck in the grind.
Bigger deals gave them the ability to slow down. To listen to what schools are actually struggling with. To design custom solutions that work.
The shift wasn't just about making more money. It was about getting their time back. Time to think. Time to process. Time to grow the business in ways that actually matter.
I see a lot of solopreneurs stuck in this trap. You're working harder than ever, but you're spread too thin. Chasing volume instead of value.
Sometimes the answer isn't working harder. It's working smarter. Fewer clients. Better clients. More impact.
Episode 7 of "The Shift: Insights from The Founder's Table"
#TheShift #FoundersTable #EdTech #K12Sales #Entrepreneurship
Selling to Educators Is Different
​
Season 1, Episode 8
Selling to Educators Is Different.
"I know how you feel. I've been there."
That's what this founder told me when I asked them what they'd say to skeptical EdTech founders who think they can figure it out on their own.
They spent years learning from YouTube, AI platforms, and other consultants.
But here's what they realized: selling to educators is completely different. You can't take the same approach you'd use anywhere else.
They told me I saved them years of failure. Years they would have spent figuring out what I already know from decades in K-12 sales.
They also said something that stayed with me: "All the best athletes, speakers, and performers have coaches. If you want to be the best, you learn from the best."
The return on investment for them has been huge. Not just financially, but in time.
→ They got their time back.
→ Better clients. Better sales.
→ A better understanding of their own value.
They've worked with other sales consultants before. But those consultants didn't understand the education space.
Their advice to other founders? Don't waste time chasing people who don't know how to sell in K-12.
It's a different game. And working with someone who gets it will get you where you want to be much faster.
I don't usually share testimonials like this, but this conversation meant a lot to me. It reminded me why I do this work.
Episode 8 of "The Shift: Insights from The Founder's Table".
#TheShift #FoundersTable #EdTech #K12Sales #Entrepreneurship
Don't Trust Me, Test Me
​
Season 1, Episode 9
Don't Trust Me, Test Me.
"Where would you be a year from now if you didn't solve this problem?"
I ask founders this when they're thinking about working with me.
One founder's answer: "I'd be in really rough shape right now."
They've been through some tough challenges over the past eight to ten months. Without what they learned from our work together, they're not sure they would have made it.
Something else they told me—they keep a sales call outline open on their screen for every single call. Talking points, questions to ask, how to move the conversation forward.
It works.
They almost never get a no. Usually it's yes, give me some time, or reach out again soon because I want to keep talking.
Why?
No pressure.
It's about fit and value. They're guiding the conversation, not telling schools what to buy.
School leaders want someone they can trust. Someone who gets them and actually cares.
Leadership is lonely. When you listen, ask the right questions, and show your value in a way that makes sense, they can decide if it's the right fit.
I don't ask anyone to trust me. I challenge them to test me. Prove me wrong.
That's what I told this founder when they were learning to do things differently.
They tested it. And it kept their business alive during one of their hardest stretches.
Episode 9 of "The Shift: Insights from The Founder's Table".
#TheShift #FoundersTable #EdTech #K12Sales #Entrepreneurship