6 Hard-Earned Lessons Entrepreneurs Wish They Knew Before Starting Up

Starting a business is equal parts exhilarating and daunting. The leap comes with uncertainty, risk and a steep learning curve that no guidebook fully prepares you for. Six founders recently featured in ICSC’s Small Business Center share the lessons they learned the hard way — from misjudging the market to underestimating timelines — that they wish they’d known at the start.

Test the Market Before You Launch

Kendra Scott, founder Kendra Scott LLC, who shared her journey as a keynote speaker at ICSC LAS VEGAS 2025

“I started my first business at 19. I actually took a temporary leave from college to open a small hat store in Austin, Texas. I started it really for my stepfather, who was diagnosed with brain cancer. I wanted to create headwear that was both comfortable and stylish for people experiencing hair loss.

The destiny is that my business did not work out. Turns out, most people just don’t wear hats. I ran that shop seven days a week, open to close, for five years — barely making enough to get by, selling maybe a hat or two a day. I couldn’t afford help. [I] ended up selling maybe a hat or two a day on a good day.

After five years, I had to close the business. It was devastating. I had started it for my stepfather and by that point I had lost him to brain cancer. I didn’t have a college degree. I had poured everything into that business — my time, my money and my heart.

But I remembered my stepfather’s words: ‘Honey, I want you to use the gifts you were given to do something good in this world.’ He always told me that every hard thing in life has a purpose. You just have to stay open to what comes next.

What came ahead was that I had also sold [some handmade] jewelry in the hat store. After I closed it, customers would call, not for hats, but for the jewelry.”

That side hustle became the start Scotts eponymous jewelry brand, which launched in 2002 and is now a billion-dollar company.

Always Build In More Time Than You Think You’ll Need

Jennifer MacRobbie, co-owner of Gotta Have Art, a Maryland art studio that was delayed three months in opening

“We got our keys for the space in March, and now [in June] we’re still building out. We originally thought [construction] would be a small project, something we could finish quickly, but it’s slowly unraveling into something much bigger than we expected.

For example, we originally had just one bathroom, and now we’re required to add another. That wasn’t part of our initial plan. The space is only 1,600 square feet, but once you get into the codes and requirements, there’s a huge learning curve.

It’s definitely taken longer than we anticipated, and that’s been nerve-wracking. For me, that’s the biggest stress point: the unknowns in the timeline.”

Start Small and Grow Smart

Elijah Campbell, Nautical Bowls franchisee in Marco Island, Florida, and Miami Dolphins football player

We own the rights to three [Florida] locations: one in Weston, one in Cape Coral and Marco Island. Marco was always going to be our first because it’s such a great location. Plus, my in-laws have lived there for a while, and my sister-in-law is there, too. Since I’ve been with the Dolphins, we’ve spent almost all our off seasons in Marco, so it’s like a second home. Eventually, we’re looking at moving to the Naples area permanently. Proximity-wise, Marco made the most sense.

At the beginning, we were super ambitious, and I bought three lots. In hindsight, I wouldn’t have done that. I would have focused on one location at a time. Now, I’m sitting on two lots that I’m not going to be able to use for at least another year. I’m tying up capital that I could have put in the Marco location. A better option would have been to wait and buy the next lot when we were ready to expand.”

Momentum Doesn’t Guarantee Future Sales

Jackie Wachter, co-founder of Fount leather bags and goods

“I was selling high-end vintage at The Cleveland Flea and before that the Brooklyn Flea when I lived in New York City. We started going to all these [maker and art markets and] shows with our bags, but the job was very part-time. I was a school teacher. Phillip was working at our church and then also at Restoration Hardware. Then in 2014, we got featured in Country Living magazine. As soon as the article was published, we got requests for hundreds and hundreds and hundreds of orders.

We both quit our jobs and jumped in headfirst. We hired people and ordered all this machinery to make us more efficient. That was the October issue, and we worked night and day fulfilling orders all the way up through Christmas. It was so exciting!

We worked nonstop to fulfill the flood of orders through the holidays. And then Christmas turned into January. Want to guess how many orders we got that month? The answer is three. We got three. We were terrified because at that point, we had nine people on the payroll, including Phillip and I. We panicked, and we were like: “What are we going to do?

So we traveled doing shows all over the Midwest, Atlanta, D.C., Pittsburgh, Cincinnati, Columbus and Chicago. We were doing 52 shows a year. It was a big grind. We hit the road and hustled to keep the momentum going.”

MORE FROM WATCHER: How Leather Bag Maker Fount Reached Its Audience

The Right Location Can Make or Break Your Business

April Peterson, co-owner of Fredericksburg, Virginia outdoor-recreation retail store River Rock Outfitter

“[Location] was one of our really big challenges. I don’t think that we understood at the time how important that decision was, and it almost killed our little business.

For our first five years, we were in a different building. That space was one street behind what’s considered the main street in our district. It’s next to a public parking lot and right near the river. On paper, everything seemed right, but it turns out one street behind main street makes a big difference. We severely underestimated how that small shift would affect foot traffic. For five years, the amount of money we had to spend to acquire every single customer was a real challenge for our business.

After that lease was up, we looked for another space that was in a more high-traffic area. We moved into our new space in September of 2019, right before COVID. We didn’t know it at the time, but that move saved us during COVID because we had visibility and natural foot traffic to our store.”

Have at Least a Year of Operating Capital Ready

Kyle Inserra, restaurant real estate consultant

“Make sure you have significant operating capital in the bank before opening. The old rule of thumb was that you needed four to six months of capital in the bank to open, but now I advise clients to have a full year’s worth of capital in hand before opening.

If you’re not able to capitalize on multiple streams of income, you don’t want to get to a place where you’ll be shortened on produce because you couldn’t pay your produce bill. And in places like New York, if you don’t pay your liquor bill to one vendor, every other vendor will only deliver to you on cash. This can become a toxic cycle. The best way to get ahead of cash flow issues is to just have the cash and realize that’s part of your investment.”