What Are Some Risks that Paid Off for Entrepreneurs?

What Are Some Risks that Paid Off for Entrepreneurs?

Entrepreneurship is synonymous with risk-taking, and to illuminate this path, we've gathered firsthand experiences from founders and CEOs. From investing in high-stakes advertising to community outreach for law firm growth, discover the diverse risks that nine entrepreneurs embraced which ultimately led to their success.

• Investing in High-Stakes Advertising
• Scaling With Freelancer Support
• Early Adoption of New Tech
• Learning From Initial Business Failure
• Pioneering Remote Work Culture
• Entering an Unfamiliar Industry
• Expanding Capacity Before Client Acquisition
• Quitting Job for Entrepreneurial Pursuit
• Community Outreach for Law Firm Growth

Investing in High-Stakes Advertising

After a few successful course launches as a relatively new coach, I decided to aim for a $1 million launch. To do that, I knew I had to invest about $80,000 in paid ads, which felt scary—especially because I knew I wouldn't be able to recover financially if I invested that much and didn't get the sales I needed. That's why I decided to divide up my budget to drive sign-ups to my different webinars and spread out the risk. The result: $800,000 in sales from my third launch, and over $1 million within 11 months of my first sale. My takeaway? Calculated risks do pay off, but make sure you know your numbers beforehand to know what results you can expect.

Scaling With Freelancer Support

I accepted more clients than I could feasibly handle. When I first started my writing business, client acquisition was my top priority. But once I had a steady client base, I continued to accept new clients and say yes to every project that came my way. In 2020, when COVID-19 started, I was suddenly inundated with requests from clients I'd been regularly working with and several whom I hadn't heard from in months.

But I didn't turn a single client away. Instead, I onboarded a few freelancer friends to help with the overflow. This allowed me to scale my revenue and maintain good client relationships. My business flourished at a time when many were closing their doors. I was able to help others in a time of need while building my reputation.

Lesson learned: You'll find your most creative solutions when you have no other choice.

Early Adoption of New Tech

As the CEO of Startup House, one of the risks I took that paid off was investing in a new technology that was still in its early stages. Despite the uncertainty, we decided to develop a project using this technology, and it turned out to be a huge success, attracting new clients and boosting our reputation in the industry. From this experience, I learned that taking calculated risks can lead to great rewards, and that staying ahead of the curve is essential in the fast-paced world of software development.

Learning From Initial Business Failure

Starting my first business was the biggest gamble I've ever taken as an entrepreneur. Even though it didn't really take off, that experience laid the foundation for everything that came after. It was like a crash course in entrepreneurship, teaching me everything from managing money to the ups and downs of building a team. My first business failure wasn't a step back but rather a step up for what was to come. It made me tougher and taught me lessons that sped up the success of my future ventures.

Pioneering Remote Work Culture

Navigating the unpredictable waters of entrepreneurship has meant making bold decisions and taking calculated risks. Here is one example of a risk we took that not only paid off but also taught us invaluable lessons about innovation, culture, and the power of intuition in business.

Embracing Remote Work Early On: Long before it became a necessity, we decided to transition Toggl to a fully remote operation. This was at a time when remote work was often equated with a lack of productivity and commitment. The decision was met with skepticism, but it allowed us to tap into a global talent pool, significantly reduce overhead costs, and improve employee satisfaction and productivity. The risk paid off, especially when the world shifted towards remote work, putting us years ahead in experience and infrastructure. I learned that challenging conventional wisdom, when done thoughtfully, can provide a competitive advantage and set new industry standards.

Entering an Unfamiliar Industry

One of the biggest risks I took as an entrepreneur was starting a business in a new industry. I had no experience in the industry, and I knew that it would be a steep learning curve. However, I decided to take the risk because I believed in the potential of the industry and the product. The risk paid off, and the business has been successful. The biggest lesson I learned from this experience is the importance of being flexible and adaptable. When starting a business in a new industry, you have to be willing to learn quickly and adjust your strategy as you go. You also have to be willing to take risks and try new things. If you're not willing to take risks and make mistakes, you'll never be able to grow and succeed as an entrepreneur.

Expanding Capacity Before Client Acquisition

As an entrepreneur, one significant risk I took was investing a substantial portion of our capital into expanding our production capacity before securing a large client. It was a nerve-wracking decision, but it paid off when we landed a major contract shortly after. This move taught me the importance of strategic risk-taking and having faith in our capabilities. It also highlighted the necessity of being proactive and creating opportunities rather than waiting for them to come to us. Overall, it reinforced the idea that calculated risks are often necessary for significant growth and success in business.

Quitting Job for Entrepreneurial Pursuit

My biggest risk that paid off tremendously was the decision to jump into entrepreneurship. When my husband and I started our media company, we didn't have two pennies to rub together. We barely made ends meet with my retail job back then. However, I took a risk that, at that time, seemed insane—I quit my retail job, even though it was literally our only income and the company didn't have any leads or proper clients yet. I jumped into entrepreneurship with both feet without having any security blanket whatsoever.

Today, we have a profitable media company with a steady client base, and we're moving towards financial freedom—that's something that was unfathomable back when I was working 12-hour shifts selling clothes in a shopping mall. Though it was hard at first, it's a risk that has paid off a hundredfold: if I hadn't jumped back then, I might have been stuck in my job for years, wandering aimlessly. Now, I have purpose, meaning, and complete freedom since I'm my own boss. This whole journey has taught me to have more trust in my own abilities and have faith in the future, since everything will work out in the end, as long as you keep moving forward.

Community Outreach for Law Firm Growth

As a managing partner in a personal injury law firm based in Northern Alabama, one significant risk I took as an entrepreneur was investing heavily in local community outreach programs. Despite initial uncertainty about the return on investment, we actively sponsored events and provided free legal workshops. This endeavor paid off tremendously as it enhanced our firm's visibility and credibility within the community. We learned that prioritizing local engagement fosters stronger client relationships and cultivates trust, ultimately leading to increased referrals and case inquiries. This experience reinforced our commitment to being approachable and reliable hometown lawyers, dedicated to serving our community's legal needs.