Teach & Earn by Justin Jackson

Teach & Earn

Bootstrap your company by teaching online

Where'd you get the money to fund your company?

When you're bootstrapping your company, you need to find creative ways to pay your bills.

Bootstrapped companies like Basecamp, Groove, and ConvertKit funded their product development by offering online courses and workshops.


  • Basecamp's design workshops would earn $10,000 every time they hosted them.
  • Groove launched a 6-week course and earned $120,679 for their startup.
  • Nathan Barry used $50,000 from his course earnings to fund his SaaS, ConvertKit.

How to get started

Teach & Earn is a series for bootstrappers like you. I'll help you stair-step your way to earning income from video tutorials and workshops.

You'll learn:
  • How to choose an audience 
  • How to pick a topic
  • How to start small, by doing a local workshop
  • How to transition to running an online workshop
  • And finally, how to build and launch an online course

What's included?

Video Icon 16 videos File Icon 4 files Text Icon 1 text file


Welcome to Teach & Earn!
6 mins
Workbook: define your goal
How do you choose your topic?
12 mins
Workbook: find your audience
Create your MVP
6 mins
Run a local workshop
Start with a local workshop
6 mins
Using Meetup and Eventbrite
9 mins
Promote your workshop
6 mins
Plan your workshop
8 mins
Workshop checklist
11 mins
Local Workshop Checklist.pdf
55.7 KB
Run an online workshop
Running an online workshop
5 mins
What equipment will you need?
6 mins
Hosting an online workshop (Part 1)
11 mins
Hosting an online workshop (Part 2)
9 mins
Final thoughts
2 mins
Bonus: HTML template
174 KB
Create an online course
Introduction to course creation
3 mins
Creating your course on WordPress
19 mins
Creating your course on Podia
12 mins

Why bootstrappers should teach; for fun and profit

Creating a course, writing a book, or doing a workshop helps you connect with customers (while you're building your app) and earn revenue now.

It takes time to develop these assets, but when you do, there are many benefits.

1. Teaching forces you to start small

"Starting small puts 100% of your energy on actually solving real problems for real people." – Derek Sivers
How do you want to make your customers' lives better?

Basecamp is software that helps small businesses improve the way they work.

But before they built software, they did workshops that had the same aim: "help small businesses improve the way they work."

They've been helping customers make progress on this same topic for years! (Even before they built software).

Most of the problems we hope to solve with software can first be addressed manually.

2. Make sales now (instead of later)

Believe it or not, getting five people to pay you to attend a one-day workshop is more accessible than selling software to anonymous people on the internet.

I've been selling SaaS since 2008 (at Mailout, Sprintly, and now Transistor).

Yes, selling apps is more scalable, but nothing beats the effectiveness of:

  • Crafting a sales pitch
  • Making a list of potential prospects
  • Calling (or emailing) each person manually
  • Following-up until you get a "yes" or a "no"
Arguably, it's the lessons that you learn "hustling on the street" that help you to scale your marketing efforts later on. (Which pitch resonates most with people?)

"Making money takes practice, just like playing the piano takes practice." - Jason Fried
Learning how to sell doesn't just happen. It takes practice. And selling a course, or a workshop is a great place to start.

3. Build your audience now (instead of later)

Many of you told me:

"I'm interested in building an audience for my launch."
Growing an audience takes time! But, you can start to earn people's trust now by teaching them.

In 2012, I bought a book called "Designing Web Applications" by an author named Nathan Barry.

The next year, he launched his web app, ConvertKit. I signed up for that too, and now I'm his longest running customer.

As you focus on one audience, and you keep solving their problems, you'll build momentum. Your audience will grow, and when it's time to launch a "serious" product, you'll be ready.

4. Earn revenue and fund your company

Alex, the founder of Groove, tells a story about how his software company nearly went bankrupt:

"In those early days, Groove was struggling to stay alive. We simply weren’t making enough to pay our bills, let alone invest in improving the business."
To survive, Groove had to do things differently.

One thing they tried, in 2017, was running a six-week course. To Alex's surprise, all of their spots sold out. In total, the session raised $120,679 for the company.

Likewise, Nathan Barry initially funded ConvertKit by investing $50,000 of the money he'd earned from his design books.

It's true:
not everyone is going to hit those big numbers.

But, in your early days of bootstrapping, every bit of revenue helps. An extra $500 or $1,000 can make the difference between burning out, and living to fight another day!

Who's behind this?

Hi! I'm Justin Jackson. I run MegaMaker, and I'm building Transistor.fm