10 Common Mistakes Former Educator Founders Make

THIS WEEK’S LESSON

10 Common Mistakes Former Educator Founders Make

I don’t remember who taught me this quote, but it’s been seared into my mind.

And for good reason.

When you found a business, you’re going to make a lot of mistakes.

And thus, a choice:

• Will you beat yourself up and play smaller and smaller?

• Or will you reframe mistakes as potential learning opportunities?

No matter where you are in your Former Educator Founder journey, I hope you can learn from all the mistakes I’ve made in the past.

Let’s get to the learning …

Mistake #1: Doing it all on your own

Hats I’ve worn in my business:

• CEO

• Head of Marketing

• Head of Sales

• Content Creator

• Podcast Host

• Show Notes Writer

• Podcast Editor / Video Editor

• Mastermind Coach

• Finance: Billing, Invoicing, P & L

• Operations

• Customer Service

• R & D

• Legal

Hats I now wear:

• CEO

• Head of Marketing

• Head of Sales

• Content Creator

• Podcast Host

• R & D

I can still give more away and will learn to do so in the future.

The first thing I hired for was podcast editing and haven’t looked back since then.

One way to think about it: If I can pay $20 for a pod episode to be edited, what activity could I do during that hour to make 10x-100x or more?

Bottom line: Focus on your unique super power and money making activities. Give away the rest as quickly as you can.

Mistake #2: Developing the Me Disease

The Me Disease is a trap that many Former Educator Founders fall into.

If you’re constantly posting your workouts, what you ate this week, or talking about yourself the majority of the time, you’ve been infected 🧟‍♂️

It’s a tragedy too because so many teach that you need a personal brand. As Lochhead shares below, everyone teaching personal branding is wrong:

Want to learn more about the Me Disease (and if you have it). Check out this LinkedIn carousel here.

Bottom line: Lean into your different and build a reputation on results.

Mistake #3: Talking about your solution (too much)

Over the years I’ve talked a lot about solutions I’ve built. None more than the mastermind we run for K12 school administrators.

It’s tempting to do.

After all, most Former Educator Founders fall in love with a solution they’ve built. And rightfully so! You’ve invested a ton of time into that solution.

• But when you market your solution, I think you want my money.

• When you market the problem, I think you have the solution.

Bottom line: Fall (even more) in love with the problem. Talk about it every chance you get.

Mistake #4: Lack of investment

I was so scared to invest in myself in the early days of my business.

After all, Business 101 states you should make more money than you spend.

When I look back at every business breakthrough I’ve experienced, I can trace it back to a coach, mentor, mastermind, program, team member I invested in to take my business to the next level.

The financial cost of these investments are important to consider. Even more important: do you have the time or teammate to implement what you’ll learn?

Bottom line: You can figure it out and take years to do so. Or you can take the short cut and learn from the experience of others.

Mistake #5: Misunderstanding the 80/20

This one took a while for me.

So I was treating every activity as equally important.

The Pareto Principle states that 20% of your activity creates 80% of the results.

In terms of content: I can focus on my email list and podcast and ignore every other channel and be fine.

In terms of sales: focus on delivering results and having those results travel by work of mouth attracting new clients I can help.

Bottom line: Everything is not important. Identify and do only key activities.

Mistake #6: Creating a complex strategy

How did Steve Jobs bring Apple back from the verge of bankruptcy?

He cut down most of their products to just a few.

What was Elon’s strategy for Tesla?

• Build sports car

• Use that money to build an affordable car

• Use that money to build an even more affordable car

• While doing above, also provide zero emission electric power generation options

Now compare that with your 30+ page strategic document you can’t even remember.

My strategy fits onto one page. My team was fired up when they read it. When I share it with others they clearly know if our solutions are for them or not.

It’s simple and focuses on the problems in education.

I haven’t “officially” wrote it but here’s my secret plan and POV for edupreneur.ing:

POV: Education needs to be reimagined. Those best positioned to reimagine education are ones that understand K12 deeply. But an understanding of education is not an understanding of business.

3-Line Secret Plan:

• Create and grow a value first newsletter for Former Educator Founders

• Build relationships with the readers and learn their unique problems

• Create solutions to those problems

Bottom line: Keep it simple.

Mistake #7: Not niching down

• They say that the riches are in the niches …

• And that you should niche down until it hurts …

You won’t experience the former, until you do the latter.

Most people don’t niche down because it’s hard.

They also mistakenly believe:

If I can talk to 1,000,000 kind of interested people, I’ll make more money than talking to 1,000 super interested people.

This newsletter is a result of niching down.

• Big group: company founders

• Smaller group: ed-tech founders and solopreneur ed consultants

• Even smaller group: Former teachers and admin who started a company (a group I call Former Educator Founders).

Now here is the irony: by focusing on the smallest group, I expand my reach.

Case in point: the first company I’m actively helping with category design with equity as part of the deal is an AI company in the architecture space.

How did that happen? The founder has seen what I’ve built (my results) and enjoys my content. So now we’re working together. He wants to niche down like that too (and design a category for his AI company).

Bottom line: I’ve never met a founder who has said, “Niching down didn’t work for me.”

Mistake #8: Working in isolation

My wife once described me as a monk.

• I love solitude (and my own company)

• I love to meditate

• I love being outside

This can be advantageous when it comes to Deep Work.

It is costly when it comes to Impactful Work.

As a result, I’ve learned to reach out, ask for help, and rely on others to help me accomplish my big dreams.

Founders are the biggest opportunity and biggest bottleneck in their company.

Bottom line: Invest in a team. Reach out for help.

Mistake #9: Not taking time off

I joined Strategic Coach last year.

The most important lesson I learned: you’ll make more money the more time you take off.

That’s counterintuitive and I can tell you that it’s true from my experience.

I’ve been terrible at honoring breaks, days off, and vacations since founding my company back in 2015.

So I decided to track my days off last year (and my bank account). Both revenue and (more importantly) profit are up.

Why?

You get very clear on what’s important and what is not. You get clear on what I taught in Mistake #5: Misunderstanding the 80/20 Principle.

Bottom line: Take time off. You’ll come back with better ideas and with more energy to grow your business.

Mistake #10: Spending more than you make

Business 101: Make more than you spend.

Run as lean a company as possible.

Last year I made some BIG bets on advertising as well as coaching programs. Revenue was up, but I wouldn’t have known it because profit was way down.

This year has been different (and I’ve got a quarter to go):

The equation was simple: make a lot more money and spend a lot less = 728% increase in profit. I cut back on apps and coaching programs mostly. I was in 3 programs (I cut to the most beneficial one). I also cutback on 1099 contractors that weren’t helping the company grow.

Everything I share in this newsletter I’ve done or am doing 😀

Your success as a Former Educator Founder is my success.

Bottom line: Run as lean a company as possible.