David Osterweil | Crain's Orlando

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

David Osterweil


Tampa Bay-based Fitlife Foods is a performance, lifestyle and weight loss brand known for its made-from-scratch meals. Fitlife is the second-largest exclusively prepared-meals retailer in the country and the largest in the Southeast, with 15 locations throughout Tampa Bay, Orlando and South Florida. The company recently was selected as one of the 22 Co-Learning Partners of the Lean Enterprise Institute, a not-for-profit research, publishing and training organization that specializes in lean thinking and practices that help businesses create more value while consuming the fewest possible resources.

The Mistake:

I wish I’d hired a chief financial officer sooner. When you start a business, you’re doing so many things and you think you can wear every hat.

I was a solo entrepreneur, so I started this business completely by myself. I brought in the right chef partner about six months after that. I was in it for a year and then I raised some friends-and-family money. But when it came to the managing of the day-to-day business and making sure we’re doing things the best way that we ought to be doing it – that’s one of the things I would have redone. I did not hire a full-fledged CFO until I think the beginning of my third year.

I had an outsourced accounting firm I used in year two. But I think I would have brought in that person that I would have day-to-day interaction with.

When we brought in our first group of investors, when I had to go through the first capital-raising process, it was very much of a distraction. Incredibly important. You have to do it.

But in the meantime, you lose a lot of focus on your core business for a brief period of time. I think any entrepreneur who’s raised capital and gone through that [can relate]. There are only 25 hours in the work day, right? You really are at the mercy of time. And raising capital really does take a full-time effort. And I did not want to go through that process again, where I was fully distracted.

So after I closed the [investor] round, I really said to myself, "I need to bring somebody in." And I did that in collaboration with them. It was very collaborative.

You want to treat every dollar like it’s your last dollar.

The Lesson:

Especially for solo entrepreneurs, you really need to find complimentary skill sets that can make your business the best it can possibly be. Say you have someone who’s great on the tech who needs someone on the marketing side. Or they’re great on the finance side, but they need someone on the skill side.

I’ve always brought in investors who are about more than just bringing money to the table. They’ve really brought expertise in various areas. You don’t want to be the smartest person in the room. And one of my investors said to me, you know, it shouldn’t be that hard. Especially when you look at that side of the house. I have an MBA in finance, so I understand how to raise capital and those things.

But at the same time, you also need someone who has a laser eye on accounting and financing in a completely different way, who is just focused on it. Because everything you’re trying to do, you want to be really smart. You want to treat every dollar like it’s your last dollar. What’s the return on this individual dollar? And you know, you [can] think that way, but as an entrepreneur, you’re thinking about ten other things too.

Follow FitLife Foods at @FitLifeFoods.

Photo courtesy of David Osterweil

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