When Have You Taken Calculated Risks in Business?
In the world of business, taking calculated risks can lead to breakthrough success or valuable lessons learned. We've gathered insights from fifteen executive officers, including CEOs and Founders, who share their experiences from investing in new AI tools to piloting projects in emerging markets. Their stories provide a fascinating glimpse into the high-stakes decisions that shape the trajectory of companies and industries.
- Invested in New AI Tools
- Launched Cyber Insurance Product
- Expanded Legal Service Offerings
- Entered New International Market
- Invested in Revolutionary Technology
- Founded Healthcare-Focused Agency
- Developed New Tire Segment
- Transitioned to Law Firm Founder
- Added Mass-Tort Lawsuits to Services
- Incorporated Drones for Site Surveys
- Focused on Shipment Tracking Niche
- Started Own Legal Practice
- Shifted to Consumer-Focused Marketing
- Expanded into Commercial Construction
- Piloted Project in Emerging Market
Invested in New AI Tools
One big decision I made was to invest in new AI tools for analyzing data, even though they were new in our industry. It was a tough choice because it cost a lot initially, and we weren't sure if the technology would work well for us. But I thought AI could help us better understand our clients' data, which would improve our marketing campaigns. The outcome was excellent. In just a year, more clients stayed with us, and we could make our marketing more personalized and effective. This move not only made us different from other companies but also showed that we were looking ahead and trying new things.
Launched Cyber Insurance Product
One of the most memorable calculated risks I took at Leverage was launching our cyber insurance product. We were doing well with our usual services, but I saw a growing need for cyber insurance as cybersecurity threats increased.
I spent a lot of time researching and looking at market trends. Even though the data looked good, it was still a big leap. We needed new technology, had to train our team, and run a campaign to educate our clients about this new product.
We used Mailchimp and HubSpot to target our marketing efforts, focusing on businesses most at risk. At first, the response was slow, and there were definitely moments where I questioned the decision. But we kept tweaking our approach based on feedback.
After about six months, interest started to grow. By the end of the year, cyber insurance became one of our fastest-growing products. This move not only expanded our services but also positioned Leverage as a forward-thinking leader in the industry.
Expanded Legal Service Offerings
As the founder of a legal process outsourcing company, I recall a time when we took a calculated risk by expanding our service offerings to include complex litigation support.
This decision required significant investment in training our team and upgrading our technological capabilities to handle large-scale document management and e-discovery tasks.
Despite initial challenges and uncertainties about client demand, our proactive approach paid off when we secured a multi-year contract with a prominent law firm seeking specialized litigation support services.
This calculated risk not only expanded our portfolio but also solidified our reputation as a versatile and reliable partner in the legal industry. It underscored the value of strategic risk-taking and the rewards of anticipating market needs ahead of competitors.
Entered New International Market
I remember a time when our company was considering expanding into a new international market. The decision required a substantial investment and a commitment of resources, but the potential for growth was significant. We conducted thorough research, analyzed market trends, and weighed the risks against the potential rewards. After careful consideration, we decided to move forward with the expansion.
The result was a game-changer for us. Not only did we successfully enter the new market, but we also saw a significant increase in revenue and brand recognition. The expansion opened up new opportunities for partnerships and boosted our competitive edge. This experience taught me the value of taking calculated risks and how important it is to have a well-thought-out strategy and strong research behind major business decisions.
Invested in Revolutionary Technology
Taking a calculated risk can often feel like walking a tightrope, but sometimes it's necessary for significant growth. I recall a pivotal moment when we decided to invest heavily in a new technology that promised to revolutionize our book-creation process. It was a significant financial commitment with no guaranteed return, and many in the industry were skeptical.
However, we meticulously analyzed the potential benefits, weighed the risks, and trusted our instincts. The investment not only streamlined our operations but also enhanced the quality of our services, leading to a substantial increase in client satisfaction and revenue. It was a gamble, but with careful planning and a clear vision, it paid off, demonstrating that sometimes the most rewarding opportunities come from embracing well-considered risks.
Founded Healthcare-Focused Agency
As the founder of PracticeVIP, a calculated risk I took was leaving my corporate job to start an agency focused solely on healthcare providers. After 15 years in pharmaceutical sales, I identified an opportunity to leverage my experience and help practices grow. It was risky walking away from stability and a steady paycheck, but the potential to make an impact was huge.
We spent a year developing our 'done-for-you' growth system targeting medical practices before we officially launched. When we did, the response exceeded our expectations. Within 6 months, we had to double our team to meet demand.
The keys were doing our homework, gaining a deep understanding of the challenges practices face, and creating solutions that actually work. Risk means sacrificing comfort for opportunity. Start with a vision, test it out, learn, and adapt. With hard work and persistence, risks can transform businesses. Ours did.
Developed New Tire Segment
We have taken calculated risks while:
- Investing in the development and launch of a new tire segment, such as Super-Giant tire manufacturing, resulting in higher revenue and an improved product screen.
- Allocating funds for Research and Development with a risk factor based on projected demand, market analysis, and ROI.
- Raising the prices of tires to improve the premium positioning of our company, with the risk of losing some price-driven customers.
Transitioned to Law Firm Founder
A big risk I took in my career involved transitioning from a position as an insurance adjuster to founding my own law firm. After being fired from my previous job, I was faced with the necessity to start fresh. This situation led me to work with a business coach, who played a crucial role in helping me set goals and envision a future as a business owner. The coaching inspired me to take bold steps and commit to becoming an entrepreneur.
My legal journey began with a role as an insurance adjuster at Travelers Insurance, where I was part of the Special Liability Group. In this role, I handled complex cases involving asbestos, lead paint, trucking accidents, and more. The experience I gained here was invaluable and provided a solid foundation for my subsequent legal career. After completing law school and being admitted to the bar in Maryland and the U.S. District Court of Maryland, I took on a position as a prosecutor at the Baltimore City State's Attorney's Office. There, I handled a wide range of cases, including criminal, DUI, juvenile, and traffic cases, in both circuit and district courts.
Taking the leap to establish my own firm was a calculated risk driven by the necessity of finding a new path after my job loss. It was a bold move that required a significant investment of time, effort, and resources. The decision to start my firm was not without challenges, but it ultimately paid off. The experience and skills I acquired in my previous roles equipped me to build a successful practice, and the risk I took led to the creation of a firm that has thrived in providing legal services and inspiring others to pursue their goals with determination and dedication.
Added Mass-Tort Lawsuits to Services
Templer & Hirsch took a calculated risk when they added mass-tort lawsuits to their list of services. A lot of market research showed that people in this area need lawyers more and more, so this choice was made.
At first, it required a significant investment in specialized training and tools. We thought, though, that our firm's experience with personal injury cases would help us with mass torts as well.
Even though there were challenges, our well-thought-out bet paid off. These actions not only made us a lot of money but also established us as a strong player in mass-tort lawsuits.
By taking this risk, we were able to expand our business and make our firm much larger and more profitable.
Incorporated Drones for Site Surveys
We decided to invest in drones for site surveys and inspections. It was a big cost and would take time to see results. After researching, I saw that drones could speed up our work and make it more accurate. We trained our team and added drones to our processes.
The outcome was great. Surveys were done faster, and we spotted issues early. This saved time and money and impressed our clients. The risk paid off and made us more competitive.
Focused on Shipment Tracking Niche
When TrackingMore was in its infancy, there was pressure to copy what other similar brands were doing and become a generalist post-purchase experience platform for e-commerce businesses. My co-founder and I took a calculated risk at the time by focusing TrackingMore on shipment tracking only. We aimed to allocate all available resources to build the best shipment tracking platform and offer cutting-edge package tracking services.
Although we risked being a niche brand that could be exposed to volatility in our chosen market, we were willing to take the risk. We redefined our target customer and focused on online store owners, software developers, logistics, and supply chain brands.
By pivoting our brand, we developed a better shipment tracking platform and became the go-to technology partner for brands. Moreover, we gained a competitive edge in our niche, allowing us to innovate and be frontrunners in providing air-freight tracking services as well.
Started Own Legal Practice
Taking a calculated risk, I left a prestigious law firm to start my own practice. I knew that while the secure path was to remain, true growth meant stepping out on faith. I started small, handling basic legal needs for small businesses and individuals. As clients saw my dedication, the work grew more complex. A commercial real estate developer asked me to review lease agreements for a new shopping center. Though outside my expertise, I dug in, researched, and found ways to strengthen the leases to benefit both parties. The client was thrilled, and it led to handling all their Georgia legal work. Believing in my abilities and values, though initially risky, allowed me to build the foundation for a thriving practice.
Shifted to Consumer-Focused Marketing
When we made the transition from a B2B to a B2C-focused company, we had to quickly adapt our marketing efforts. Of course, targeting a business and targeting the consumer directly is a very different approach. It's then that I took the decision to allocate over 30% of our marketing budget to partnering with social media influencers and developing our own content. It was something we had never done before and had little experience in. However, what we knew for a fact was that our buyers were consuming content; they were new DIY enthusiasts inspired by platforms such as YouTube, TikTok, or Instagram, and we were right. Sales grew at an accelerated rate, and we achieved the highest ROI on any marketing-associated spend up to that date.
Expanded into Commercial Construction
As the co-owner of Bonsai Builders, a calculated risk I took was expanding into commercial construction. We had established ourselves as a reputable residential contractor, but the commercial market presented an opportunity for growth. After thoroughly vetting several commercial projects, we chose one that aligned well with our values and expertise. It was a risk that paid off—the project was a success and opened doors to new clients and opportunities. By starting with a project well-suited to our strengths, we were able to learn and adapt, building the foundation for a new line of business.
Another calculated risk was investing in high-quality materials and craftsmanship, even when competitors were cutting corners. This commitment to excellence built our brand and reputation, allowing us to charge premium rates. It was risky, but believing in our vision and values meant having faith that clients would appreciate the difference. Over time, as our portfolio of stunning, well-built projects grew, so did our client base.
The keys were moving strategically, starting small and learning, and having conviction in our purpose. Taking risks doesn't mean reckless abandon—it means pushing yourself outside your comfort zone in a thoughtful, values-driven way. With hard work and persistence, risks can turn into rewards.
Piloted Project in Emerging Market
When I was leading our company's expansion into an emerging market, I faced significant resistance due to the market's volatility and unpredictability. Despite the skepticism, I believed in the long-term potential based on deep market analysis and decided to proceed. We launched a pilot project with a limited investment to test the waters, fully aware of the financial risks involved.
The result was a resounding success. Within 12 months, we not only recouped our initial investment but also established a strong brand presence that paved the way for further expansion. This move significantly contributed to our global growth and diversification strategy, proving that well-researched and strategically timed risks could yield substantial rewards. This experience underscored the importance of conviction backed by thorough analysis in decision-making.
