My first business made six figures when I was 19 years old. And it was not because I was particularly smart. It was because I understood something about learning that I think most entrepreneurs get completely wrong.

The Two Camps Trap

We tend to think of education as basically falling into two camps. There is the traditional side: college, industry continuing education, MBA programs. And there is the alternative side: courses, coaching, masterminds.

What most people do is dip their toes into each, figure out which one feels easiest and most intuitive, and then stick with that single mode of education forever. I know plenty of people who joined a coaching program, spent thousands of dollars, got nothing out of it, and concluded that coaching does not work for them. I have been the opposite. I dropped out of college after about a year and a half, so for the longest time I believed the traditional classroom just was not for me.

Both of those are massive limiting beliefs.

What I Actually Learned and Where

Back in 2021, I got my Spotify Wrapped and it said I was in the top half a percent of podcast listeners. The reason was simple: I was building my first business, working a side job, and driving an hour and a half each direction every day. I easily had 15 hours a day where I was listening to something. Podcasts, audiobooks, everything I could find.

That was incredibly valuable. But backing up even further, I was in a traditional business track at a four-year college pursuing a degree in entrepreneurial management. And as much as it has become trendy to trash the four-year college system, there were at least four classes that were genuinely transformative for my career: Principles of Marketing (without that class, I would not be doing what I do today), Principles of Accounting (the framework upon which every business is built), Macroeconomics, and Statistics. Those last two shaped how I think about data, supply and demand, and making decisions based on evidence.

Sometimes I wonder what I would have picked up in the 200 and 300 level courses my junior and senior year. Those are questions I will never be able to answer.

Then fast forward to 2023. I spent over $30,000 on courses, coaching, and masterminds that year. And to be honest, in 2024, I probably gained about the same amount of knowledge just from reading two specific books.

Buy Back Your Time got me thinking about systems, team building, and getting out of the day-to-day operations. Expert Secrets gave me a framework for communicating complex ideas in bite-sized, digestible ways. That skill is invaluable for anyone in an expert field, whether that is marketing, accounting, legal, or finance.

And then I discovered this eight-week financial accounting course from Harvard Business School. About $1,800, self-paced, and a legitimate business class. I have been considering taking it.

The Two Ladders Framework

Here is how I think about entrepreneurship. Imagine two ladders side by side with one person climbing each and a rope connecting them. Neither person can get way too far ahead of the other.

One ladder represents information gaps: the knowledge and skills you need but do not have yet. The other represents implementation gaps: the distance between what you know and what you have actually put into practice.

Entrepreneurship is a constant battle between learning new skills, implementing them, learning more, and implementing again. You acquire skills and information through education, then you max out those skills through implementation. Rinse and repeat for the rest of your life.

If that framework is true, then 50% of your constraints throughout your entire career are going to be information or skill gaps. Half of what is holding you back at any given moment is knowledge you do not yet have.

So why would you confine yourself to the learning methods that you think work best for you? If you say you only learn from podcasts, or only from continuing education courses, or only from coaching and masterminds, you are siloing yourself off from 80 to 90 percent of the knowledge that is out there.

The Practical Takeaway

It is your duty as a business owner to be able to get the knowledge you need from anywhere. The overpriced influencer mastermind. The $1,800 Harvard course. The two books you picked up at the airport. The college class you took at 18. The podcast you listened to on a three-hour drive.

Stop writing off entire categories of learning because one experience in that category did not work out. The entrepreneurs who break through plateaus are the ones who go find the specific information that closes their specific skill gap, regardless of where that information lives.

If you are stuck right now, the question is not whether you need to learn more. The question is whether you are limiting where you are willing to learn from.

Frequently Asked Questions

Why do smart entrepreneurs hit a plateau?

They get comfortable with one mode of learning and stick with it indefinitely. Some only learn from podcasts, others only from coaching programs or masterminds. But roughly 50% of your constraints throughout your career come from skill and information gaps. You cannot close them all from a single type of source. The entrepreneurs who break through are the ones who pull knowledge from everywhere.

Is college worth it for entrepreneurs?

Parts of it absolutely are. Principles of marketing, accounting, macroeconomics, and statistics all shaped the way I think about running a business today. Traditional education is not all bad. The mistake is dismissing an entire mode of learning because some of it was not useful. Take what works, leave the rest, and never write off a whole category.

How should business owners think about education and implementation?

Think of it as climbing two ladders side by side with a rope connecting them. One ladder is information and skills acquisition. The other is implementation. Neither can get too far ahead of the other. You learn something new, you implement it, you hit the next wall, you learn again. That cycle repeats for the rest of your career.