This is another post in my series on what I’ve learned from 40 years as an entrepreneur. My first venture? A lemonade stand at the end of my parents’ driveway in Brunswick, Maine. You’d be surprised how much that experience still teaches me today—especially about the fundamentals like small business accounting.
Yes, some business models—like Amazon or Meta—can ignore those metrics for years. But for most entrepreneurs, ignoring them is a fast track to failure.
And speaking of failure: that’s exactly what you should expect when you start a business. A lot of it.
One piece of advice I adopted from author John C. Maxwell:
“Fail early, fail often, but always fail forward.”
What Does It Mean to Fail Forward?
To me, failing forward means getting comfortable with failure. Most of us grow up thinking failure is something to avoid. But those who truly succeed stop believing that. Instead, they adopt the mindset:
Fail fast. Fail often. Fail forward.
I love teaching through metaphors and stories. They’re not only more fun—they speed up your learning curve. So here’s a metaphor I’ve lived:
Learning to Ski—and to Fall
I taught myself to ski. No lessons. Just old gear, a cheap community hill, and the classic 1970s economy (read: high inflation, four kids, and a doctor dad trying to make it all work). Lessons weren’t an option. So we figured it out.
How do you teach a kid to ski? You don’t say “never fall” or “you always fall.” You expect them to fall. You tell them it’s part of the process. You even convince them falling is fun: snow down your pants, skis flying, full yard sale.
In ski culture, falling is normal—even celebrated. We’ve got all kinds of terms for it: yard sale, tomahawk, putting down the landing gear. And when someone sends it big and crashes?
We don’t shame them. We respect the attempt. We celebrate the send.
Do they want to fail? No. But they’re not afraid to.
Same thing in entrepreneurship. Failure isn’t just common—it’s part of the path. Sometimes it’s even catastrophic. But if you want to succeed, you can’t let that stop you.
Story Time: Our First Ecommerce Venture
Back in 1999, my wife (@wild_woman_MT) and I started an online gift company. We ran it for two decades, focused on U.S.-made artisan goods.
We started with a $5,500 check from a high-risk lender—interest north of 29%. Not something I recommend. But it’s what we had.
After visiting a local craft fair in Falmouth, Maine, we convinced a few makers to let us resell their goods. Here’s where we failed:
- They weren’t really wholesalers.
- We couldn’t sell their work at the necessary markup (keystone pricing).
- Deliveries were late, invoices messy.
- They were artists, not suppliers. And we tried to turn them into something they weren’t.
Lessons Learned
- Understand your margins.
- Choose the right partners
So we pivoted. We started attending trade shows like the Buyer’s Market of American Craft and later, New York Now. That’s where our strategy evolved.
Our “Fail Forward” Buying Strategy
Let’s say we had a $10,000 budget. Our process looked like this:
- Walk the entire show. (Usually took a full day at the Javits Center.)
- Review over dinner and wine. We’d list potential bestsellers.
- Rank the products. Most likely to succeed → least likely.
- Allocate budget. Heaviest toward top-ranked picks.
We’d buy only two of each product (unless there was a required minimum):
- One to test.
- One as backup if it sold well.
Why? Because we assumed a high failure rate going in. We applied the Pareto Principle (80/20 rule). We knew that 80% of our profits would likely come from 20% of our products.
And that’s exactly what happened.
The Gold We Found
Out of dozens of product tests, most didn’t hit. But every now and then, we’d strike gold—a necklace, a paperweight—that we could reorder again and again. One of our top suppliers was Dogeared, a U.S. jewelry company with a killer eye for trends. We learned to bet bigger on winners and cut losses fast.
The Takeaway
Entrepreneurship, like skiing, means falling—a lot. But the ones who make it, celebrate the fall as part of the process.
- Test often.
- Expect most things to fail.
- Spot the winners.
- Double down when you find them.
That’s how we ran our business. That’s how we sold thousands of units from a $5,500 loan. And that’s how we stayed in business for 20 years.
Fail fast. Fail often. But always fail forward.
