CEO Insider

Navigating Risk While Building a Business

There’s a truth that every entrepreneur is going to have to face at some point or another: there’s no such thing as risk-free success. Ever heard the phrase, “If you’re not growing, you’re dying?” Well, it’s true…and it’s also true that all growth comes with risk.

My life as an entrepreneur has been full of risk. There’s risk in starting a new business. There’s risk in leaving a job that gives you a steady paycheck. And, there’s risk in expanding and scaling your business.

If you aren’t comfortable with risk, there’s no way you’re going to be able to build a business, let alone see it succeed. But, if you can learn how to navigate it, then the sky really is the limit.

Your Past Doesn’t Define Your Future

My journey to building a million-dollar business didn’t happen in a day. There were a lot of steps that I had to take to get there—but the biggest step was moving away from the industry I’d always worked in (restaurants) and putting everything I had into breaking into a new business.

Of course my cushy restaurant gig was risk-free. But the first big risk I took as an entrepreneur happened way before I actually opened my business: it was the day I walked away from that gig without a safety net or a plan.

Leaving my serving job was a big pivot point in my life. I wasn’t waiting tables anymore, but I still had rent to pay and bills to keep up with. I had to hustle, and cash flow was a problem (at least at first). It worked out, though, and it taught me a big lesson: you can pivot to whatever future you imagine for yourself. It involves taking a risk, but no life worth having is without risk.

Don’t Let Fear Stop You

There’s no way around it: as an entrepreneur, you’re going to encounter risk when you’re scaling a business, not just when you start one. My business partner, Jason, and I started our real estate business, Meridian Trust LLC, just before the Great Recession.

With hard work and massive determination, we climbed our way out of the recession years and laid the solid foundations of a business that would scale for years to come. Now, we were faced with our next big hurdle: just how fast should we grow?

Of course, we knew that scaling would involve taking risks. But we were okay with that. We’d been through enough of the up-and-down cycle of business to understand the importance of resilience.

We were prepared to do what was needed in the upturn to be able to ride out the next downturn. And—I really can’t emphasize this enough—we understood that all-important concept: there’s no such thing as risk-free success.

Keep Moving Forward

We decided to take a leap of faith and expand to a second office. After all, there are only so many properties in one geographical area, and with a second office, we could double our potential inventory. It was a risk, but it was necessary if we wanted to scale.

We opened office number two in Miami in 2011. It was wildly successful, pretty much immediately. We were elated that such a big risk had paid such a huge dividend so quickly.

It wasn’t without its pain points though. Jason and I barely knew what we were doing with one office, let alone two. Although business came flooding in the Miami doors, we weren’t set up to handle it as well as we would have liked. Because of that, we definitely missed some opportunities.

In a way, the gaps we experienced early on in Miami forced us to up our game. We had to figure out ways to stay just as effective even while running an operation in two different cities. Our systems like marketing and HR worked well for one office, but it turned out replicating them for two wasn’t as easy as we’d anticipated, so there was a ton of shoring-up that needed to happen to our processes there as well.

We had to put the time in to make our business processes incredibly tight. Miami forced us to be better. And once we got there, we kept moving forward. We combined our confidence in our resilience with careful planning and risk.

Stop Seeking Perfection

Since risk is inevitable, how do you navigate it? Well, to start, you completely detach from the idea of perfection.

Case in point: if we’d been obsessed with perfecting new elements of the business before launching them, we’d never have opened the Miami office. We could have played it safe, sticking with just one office, but instead we went for the risk; and it paid off.

Anyone looking to do something new is, by definition, going to do something imperfectly. Make sure you ask yourself what’s the worst thing that could happen if you try the thing you’re thinking of doing and you fail. Think about and write out possible outcomes, and I can almost guarantee you’ll realize that they’re not as bad as you thought.

I’ll never claim that Jason and I didn’t make a ton of mistakes in those years of explosive growth. There’s no way we didn’t. But, I’ll say it again: there’s no such thing as risk-free success.

We focused on good, not perfect, and on moving forward, not staying in place. We trusted in our own proven resilience. We allowed ourselves to take leaps and figure out the how as we went. Perfection isn’t the point—progress is. Take a shot, and fail forward.

Get Comfortable With Risk

Being an entrepreneur won’t work if you don’t have that ability to jump off the ledge. You have to be willing to take those all-important leaps of faith, certain of your ability to build the parachute on the way down.

Get comfortable with risk! Make a change and take massive action towards it, with the confidence that, no matter what happened in your past, you can go a lot further than you think you can.

For more advice on how to navigate risk and find success, you can find A Renegade’s Rules: How a ‘C’ Student Created An ‘A’ Life, and How You Can, Too by Oliver Seidler on Amazon.

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Oliver Seidler
Oliver Seidler is the co-founder and CEO of PropertyForce, an industry-leading real estate investment company focused on culture and employee success. After quickly becoming a top producer in real estate, Oliver started his own company in 2006. He weathered the recession and extended PropertyForce’s reach outside of Florida in 2017, with future expansion plans in the works. Aside from work, Seidler mentors young businesspeople, invests in startups, and works with Boys and Girls Clubs of America. He is a member of EO and YPO.


Oliver Seidler is an opinion columnist for the CEOWORLD magazine. You can follow him on LinkedIn.