13 Examples of Real Business Risks Leaders Have Taken

13 Examples of Real Business Risks Leaders Have Taken

To gain insight into the risks and rewards of bold business decisions, we asked 13 CEOs, founders, and other top executives to share their biggest risks and the outcomes they experienced. From going all in on a digital marketing strategy to breaking limits in competitive industries, discover the daring moves these leaders made and the results they achieved.

  • Digital Marketing Strategy Fuels Growth
  • Leaving Stability for Financial Industry Success
  • Entering Stigmatized Niche, Finding Success
  • Overcoming Early Cybersecurity Oversight
  • Remote Business Risk Leads to Growth
  • Terminating Toxic Employees, the Company Recovers
  • Selective Partnerships Strengthen Assisted Living
  • E-commerce Expansion to Multi-Platform Success
  • Brave Business Pivot Pays Off
  • Global Expansion Boosts Revenue Streams
  • Specialized Cloud Service Provider Triumphs
  • Narrowed Focus Spurs Innovation
  • Breaking Limits in a Competitive Industry

Digital Marketing Strategy Fuels Growth

I went all in on a digital marketing strategy for my business. This was a risky move, but I believed if we hired the right people and executed the strategy successfully, we would grow the company. The results have been astounding and we are taking market share from our competition. We are getting closer to being the go-to solution for YouTube A/B Thumbnail Testing.

Scott Krager, Founder, TubeSplit.com

Leaving Stability for Financial Industry Success

Entrepreneurship is basically taking one risk after another repeatedly, but they always result in crucial lessons learned or incredible payoffs. 

I think, like many, my biggest risk was leaving a well-paying, stable career with plenty of corporate growth opportunities to pursue my passion—helping people with their finances. 

Beyond the risk of leaving my job, our entire business venture felt like a risk in the financial industry. We were standing up against predatory payday loans and risking angering some of those deep-pocketed companies along the way. 

We always felt it was worth speaking the truth—that predatory lending should never happen, and we needed to educate Americans on why and how to avoid them. Fortunately, expressing those values helped us grow stronger alongside our clients.

Jeffrey Zhou, Co-founder and CEO, Fig Loans

Entering Stigmatized Niche, Finding Success

Just joining our industry was a significant risk to our success. We operate within a niche that carries a lot of social stigmas. We believed in the theory of our business and the possibility of us making profits in an unexplored industry. However, we couldn’t ignore the glaring risk of being rejected by the public for our niche services. 

Despite the odds, we dove headfirst into our business venture. We’d gain a small enough client base to get our name out in the market. The worst that could happen was that no one signed up for our services. It didn’t take long before the former idea became a reality. 

You’ll never know what’s possible if you never take that first leap into the dark.

Alex Milligan, Co-founder and CMO, NuggMD

Overcoming Early Cybersecurity Oversight

When an organization’s IT systems fail, it opens itself up to the possibility of monetary loss, interruption, or damage to its reputation, all of which are known as cyber or security risk. 

Unfortunately, I could not foresee this danger in the early stages of my company and had to deal with the consequences. My top data was compromised and it was available for my competitors to beat me in the business game. But luckily I opted for preventive measures within the due time.

The sophistication and expertise of hackers are growing. Simultaneously, businesses are amassing more and more information about their clients. This mashup poses a serious security risk that needs to be addressed actively by implementing and maintaining appropriate security measures and levels of monitoring. 

My number one piece of guidance for any entrepreneur just getting their feet wet is to establish a structured system of risk management from day one.

Vincent Zhu, CEO, ShineACS Locks

Remote Business Risk Leads to Growth

Vulnerability involves risk, but we live in a world that appreciates risk-takers and looks down on vulnerability. Really, they are the same. If you aren’t vulnerable enough to take a risk, you will remain stagnant. One of the biggest risks I have taken was to establish a totally remote business. 

There are many personal benefits to remote work. However, one often overlooked benefit that has a global impact is the reduction of stress on the environment created when workers aren’t forced to commute every day. 

How did this risk pay off? As the CEO of a remote company, I have established a successful startup that has grown to a business with seven figures in annual revenue with just a $1500 initial investment. 

We have used our funds to launch new software under a second entity and only continue to expand. I work from home and have helped hundreds of small businesses grow their own startups through the services we provide, winning governmental and large enterprise business contracts.

Maurice Harary, CEO, The Bid Lab

Terminating Toxic Employee, Company Recovers

Every startup has that one indispensable, key employee. Below the founders, there is always one lieutenant who wears a ton of hats and is a pivotal figure in the day-to-day operations of the company. It’s the one person you can’t possibly imagine your business functioning without. 

Well, for us, that key employee early on had one of the most toxic attitudes I’ve ever encountered. This person was insanely talented but totally toxic. So at a vital moment in our company’s growth stage, I had to make the very hard decision of letting this person go. 

It was a major risk, as this person had a ton of institutional knowledge and was the only employee that knew how to manage several core functions, but it was a roll of the dice regarding figuring out their role or suffering a slow death by negative culture. 

So I rolled the dice and terminated this employee. It made for a very rough month or two getting the ship righted, but in the end, it was definitely the right call.

John Ross, Chief Executive Officer, Test Prep Insight

Selective Partnerships Strengthen Assisted Living

The results of the market research done on the assisted living industry were a shock to me. Many of the centers ‌were operating with less-than-ideal conditions for housing older adults.

When I launched Assisted Living, I took the risk of omitting these centers from our partner list. I wanted to offer senior living conditions I could stand behind. It was a big decision for our company because it meant we’d have to limit our reach. This reduced our chances of becoming profitable quickly.

We stuck to our integrity, regardless. Instead, we invested in performing extensive searches for centers that prioritized the health and well-being of older adults. The initial expenses were well worth it. 

Today, we’ve partnered with over 19,000 vetted assisted living facilities across North America. I have no regrets about taking that risk years ago.

Stephan Baldwin, Founder, Assisted Living Center

E-Commerce Expansion to Multi-Platform Success

As an e-commerce business that started out selling primarily on Amazon, one of the biggest risks that we’ve taken was deciding to invest in a full-fledged web store. As a team of 12 working from a warehouse and focusing on Amazon sales, deciding to invest in a web store was certainly a risk and no simple task to pull off. 

Building a website and growing a new audience wasn’t easy, but we worked hard at it and we built a solid web store that helped us branch out our business from Amazon. In the end, the time and money investment was well worth it, and we now have an e-commerce business that sells on multiple platforms, and Lightning Card Collection became a real brand rather than just another seller.

Eric Mills, Owner, Lightning Card Collection

Brave Business Pivot Pays Off

In 2020, after a couple of years of trying to make a high-traffic, low-cost model work, I burned down my business of 8 years. It was so painful as it meant disruption for so many of my amazing longtime clients who were in my membership community. 

This risk—which I call a Brave YES—was both terrifying and liberating. I had a hunch that my next business would be related and easier to manage. 

I was right—and wrong. 

The new business I had in mind didn’t work out and I pivoted again within about six months to business strategy and courage coaching. That has worked, and it’s been amazing ever since, and now I help other female entrepreneurs take courageous risks in their businesses. In other words, I help them make Brave YES pivots.

Shawn Fink, Founder, Shawn Fink Strategies

Global Expansion Boosts Revenue Streams

Expanding into the American market and going global was a major risk for our business, but one that ultimately paid off. We invested significant financial resources, labor, and time in navigating different cultures, regulations, and practices in order to succeed. 

Despite these challenges, we secured big clients both in America and globally, which helped us diversify our customer base while increasing revenue streams. 

This decision allowed us to expand beyond what we thought possible at first glance, while also providing invaluable lessons about taking risks when necessary if there is a potential reward involved down the line.

Alister Wood, Owner, VisitUs

Specialized Cloud Service Provider Triumphs

My biggest risk was to go against the traditional way of doing business and become a specialized service provider in the competitive cloud services market. It was a leap of faith to think that more and more companies would trust us with their critical business applications and cloud infrastructure.

The result? We’re now one of the top-ranked service providers in the AWS Managed Services market, providing world-class services to customers across industries. We continue to build our reputation as a reliable and trusted service provider, and we have customer testimonials to prove it.

Taking a risk has allowed us to differentiate ourselves in the market and create an offering that is tailored to the specific needs of our customers. We are proud of what we have achieved and continue striving for excellence as we look into the future.

Karl Robinson, CEO, Logicata

Narrowed Focus Spurs Innovation

We are constantly taking risks and running experiments. 

In fact, I think that is critical for a healthy business in this complex world we find ourselves in these days. A risk we recently took was to narrow our focus to our Facilitation Certification and adjacent training, which means we had to leave our consulting revenue behind. 

Removing these services from the website and denying prospects was nerve-wracking and required determination, but so far, it is proving to be an excellent decision. We are moving forward with more private certifications, and our focus on students and alumni has opened our eyes to innovative new programming and brand-new partnerships.

Douglas Ferguson, President, Voltage Control

Breaking Limits in a Competitive Industry

Taking risks sounds synonymous with breaking free from just being average. Since the packaging industry market is holding conglomerate dominance, scaling a unit with extreme competition was a real risk-taker move! 

Knowing chances to flourish are readily less, still taking that one chance to compete was the first move to enter the industry. However, we succeeded in thinking creatively and launching different products to meet the packaging market demands and made solid and reliable clients.

Definitely, it asked for a lot of effort and cash-burning moves, but it was worth it. Simply focusing on your product/offering and burning the midnight oil to prove your product and establish within is what I leveraged. 

It also empowered us as a business to break through those self-imposed limits and eliminate the fear of seeing major players as a threat but as an enjoyable challenge. It also drove our entire workforce to learn new skills and take the business to greater heights.

Kathy Bennett, CEO and Founder, Bennett Packaging

Disrupt Magazine Article Link: https://disruptmagazine.com/13-examples-of-real-business-risks-leaders-have-taken/