Most people hear “entrepreneurship development” and picture a classroom. A program. A certificate on the wall.
A tidy set of stages in a textbook, maybe. My version looked nothing like that.
I started an Amazon business out of my college dorm in 2009 because I was annoyed at the school bookstore. Six months in, my own college sent me a cease-and-desist. Rather than quit, I took it as a push and went all in on Amazon.
We found a niche in toys and baby products, and over the next 5 years my partner Connor and I sold over $25 million. Then we built FreeUp, a freelance marketplace, from $5,000 into a business doing $12 million a year, and sold it in 2019. Nobody handed me a curriculum for any of that.
So when I talk about developing as an entrepreneur, I am not describing theory. I am describing the actual skills, habits, and systems that move you from “I have an idea” to “I have a business that runs and sells.” Here’s how I think about it.
TL;DR: How do you actually develop as an entrepreneur?
Entrepreneurship development is the real-world process of building the skills and systems that turn an idea into a business that can run without you. A certificate does not get you there; reps plus documented systems do. I built mine by starting small, hiring to the right level, keeping clean books, and writing processes until the business no longer needed me, and that same path is the one I would put you on today.
What entrepreneurship development actually means
The textbook version goes like this: entrepreneurship development is the process of improving your skills and knowledge through training and support so you can spot opportunities, take smart risks, and build a viable business. Fine as a definition. Useless on a Tuesday when you are trying to figure out what to actually do.
Here is the version I live by. Developing as an entrepreneur means closing the gap between what you can imagine and what you can execute. Every founder starts with more ideas than ability, and development is you catching your ability up to your ambition, one skill and one system at a time.
You do not close that gap in a seminar. You close it in the arena, with real money, real customers, and real mistakes.
Training and books help, and a good mentor can shorten the curve; free SCORE mentoring is worth using. Treat all of it as the map rather than the miles, and study the principles of entrepreneurship that hold up once you are actually operating.
The real entrepreneurship development process
Most articles hand you five neat stages: idea, opportunity, plan, launch, growth. Clean on paper. Messier in real life.
Here is what each stage actually looked like for me, next to the textbook.
| Textbook stage | What it looked like for me |
|---|---|
| Idea generation | I was mad at the bookstore prices. Problems you personally feel beat brainstormed ones every time. |
| Opportunity evaluation | I tested with real inventory and real listings. The market answered faster than any spreadsheet. |
| Planning | Light. I planned enough to start, then let customers correct me. |
| Launch | I started FreeUp with $5,000 and the crummiest software you can imagine. Live beats perfect. |
| Growth | Growth is where systems and people decide everything. Most founders stall right here. |
Notice the pattern. The early stages are quick and cheap, but the whole game gets won or lost at growth, because growth is where you either build systems or become the bottleneck. For the full shape of that curve, I mapped the stages of business growth and where founders tend to stall.
One habit paid off more than any other, and I credit it with our exit: clean books from Day 1. When buyers ran six months of due diligence on FreeUp, our numbers held up, and had they not, the deal likely dies. Development runs deeper than a growing top line; it means building a business someone would actually want to own.
The skills that actually develop you
Three skills moved the needle more than anything else. None of them are exciting. All of them compound.
Hiring to the right level. Early on I tried to do everything myself, then hired at random and hoped. That approach fails. The framework that fixed it came down to matching the person to the task:
“There’s three levels of people that you can hire: followers, doers, and experts. Followers, think five to 10 bucks an hour, non-US, they’re there to follow your systems, your processes. If you don’t have a system, if you don’t know how to do something, you can’t hire the follower.”
Match the task to the level, and never hand a follower a job you have not systemized yet.
Building systems, then stepping back. A standard operating procedure, an SOP, is a written step-by-step for a task. Underrated does not begin to cover it, because the SOP is the thing you actually own.
People come and go, but the system stays. I ran FreeUp with around 30 virtual assistants, VAs, in the Philippines and no US employees:
“The business of FreeUp, the actual operations, ran 99% without me. I had awesome team leaders, awesome virtual assistants, really good systems, really good processes that we improved over time.”
For the deeper version of this, here is my approach to business process solutions.
Managing cash like it is oxygen. Most founders die from running out of money, rarely from a bad idea. I set up FreeUp with a positive cash flow cycle: we collected from the client first, took our percentage, and paid the freelancer on a delay, so money stayed in the account. That one structural choice let us scale without a dollar of outside funding, because every jump in volume added to the bank balance.
None of those three are “work harder.” All three are “build the thing that makes hard work optional.” That is the real skill tree.
How I’d develop as an entrepreneur if I started today
For anyone early who wants to develop instead of only reading about it, here is the order I would run.
That loop is the same one I used to build multiple companies, and it is not flashy. But it develops you far faster than another certificate, because every rep teaches you something a textbook cannot.
Why most “development” advice fails you
Two reasons stand out.
First, the fear-mongering. You have heard that 90% of businesses fail, a myth usually borrowed from venture-backed startup odds.
The broad reality is calmer: about half of new US businesses are still operating at year five, per the Bureau of Labor Statistics. Your odds look more like a coin flip you can tilt heavily in your favor with systems and clean books.
Second, the hustle trap. For years I believed the answer was more hours, and I was wrong. As I have put it before:
“Hustle only gets you so far in business… you eventually need to learn to hire and rely on others. When I learned to do that and stop relying on hustle, everything changed.”
Development is not adding more grind; development means subtracting yourself from the work through systems and people. Get those two things right and you sit ahead of most founders who have read ten times more about entrepreneurship than you have.
Frequently Asked Questions
Bottom line
Entrepreneurship development is not a classroom or a certificate. Real development is the unglamorous work of building skills and systems until your business can stand on its own. I got there by starting small, doing the job, writing it down, hiring to the right level, and guarding my cash.
That path took me from a dorm-room Amazon account to a $12M-a-year business and an exit, and I am still running it today across the 6 companies I hold through Hirsch Gillivan on the way to 10. For the whole story from the start, here is my serial entrepreneurship journey.
Pick one task this week. Do it, document it, hand it off. Development you can feel starts right there.