Starting or running a business often means taking risks that can either make or break your company. But for some thought leaders, those risks did far more than just shake things up—they transformed their businesses in ways they couldn’t have anticipated. Below, 12 experts share the biggest risks they’ve taken and how those bold moves reshaped their companies for the better.
Focused Niche Expertise
One of the toughest decisions a business owner can make is to narrow their market and define a niche, potentially turning away clients in the process. This choice, however, can elevate a brand’s reputation, making it a go-to source for specific expertise rather than a jack-of-all-trades. This was precisely the journey for Andrew Lee Jenkins, owner of Andrew Lee Jenkins, who recalls:
The biggest risk I took with my company was pivoting our entire service offering to focus on a niche market after realizing we were spreading ourselves too thin across various industries. Initially, we tried to cater to multiple sectors, but it diluted our expertise and messaging. The decision to narrow down and specialize felt risky because we were turning away potential clients in other fields, which could have impacted revenue in the short term.
However, this move transformed the business by positioning us as experts in one specific industry, making it easier to attract high-quality clients who valued that specialization. Our marketing efforts became more targeted, and referrals within the niche grew exponentially. It led to more efficient operations, deeper client relationships, and a significant increase in long-term contracts.
Prioritized Bootstrapping
When looking to grow, many entrepreneurs feel the pressure to seek external investment. Yet, not all funding comes with ideal terms, and sometimes, retaining control requires adjusting growth expectations. This was the case for Jayen Ashar, CTO, Scaleup Consulting, who shares how a pivot in funding strategy ultimately set his business up for sustainable success:
One of the biggest risks I took was partnering with a technical co-founder who had very specific conditions. He was exceptional at his role but his requested compensation didn’t fit with raising external investment early on. Instead of chasing funding, which would’ve accelerated growth, I had to shift towards a bootstrapping strategy. This meant slower initial growth but allowed us to build a solid, profitable foundation without external interference. The risk paid off because we retained full control of the company, avoided dilution, and were able to grow at a sustainable pace. It also taught me that accommodating key team members’ needs can reshape your approach but often leads to unexpected success.
Navigated Global Expansion
Expanding internationally is often fraught with challenges, from regulatory requirements to cultural differences. Despite these obstacles, Anna Stella, Marketing Expert & Founder, BBSA, took the plunge by establishing a presence in the United States, learning valuable lessons along the way:
The biggest risk I’ve taken was when I set up my company in the U.S. I took the risk of expanding without a local partner. It was my first international expansion, and I underestimated the importance of having a solid legal and financial foundation in place. What I learned is that each country has its own unique regulations, and adhering to these faithfully from the get-go can help prevent future headaches.
In highly litigious places like the U.S., having solid legal processes is essential to mitigating preventable risks. It was a learning curve, which ultimately strengthened my global expansion strategy. When it comes to risk, I believe there are no wrong answers—just bad outcomes. Time will pass whether you do something or not, so if I’m really sold on something, and the moment is right, I’ll just do it.
Embraced Remote Work Model
Embracing remote work is not just a logistical shift—it’s a profound cultural shift that can transform how a business operates and grows. For Jamie Frew, CEO, Carepatron, this approach was a game-changer for both his team and his mission:
One of the biggest risks I’ve taken was embracing a fully remote model from day one. This decision came with its own set of challenges—managing a team across different time zones, fostering company culture without physical presence, and ensuring communication remained seamless. However, the potential to attract top-tier talent globally, while offering team members greater autonomy and work-life balance, was an opportunity I felt strongly about.
The risk transformed our business by not only allowing us to scale quickly but also building a culture grounded in trust and independence. We learned to lean into technology to streamline operations, built a robust communication framework, and empowered our team to take ownership of their work. This autonomy fostered a high degree of innovation and accountability, which reflected in the way we serve our clients. Our decision to go fully remote also allowed us to better align with our mission—creating healthcare solutions that prioritize flexibility and accessibility, both for practitioners and patients.
By taking this leap, We have been able to evolve into a dynamic and agile company, staying at the forefront of healthcare technology while ensuring our team has the freedom to focus on what truly matters—creating impactful solutions for healthcare practitioners worldwide.
Prioritized Organic Growth
Sometimes, growth comes not from more but from less. This philosophy was tested by Austin Benton, Marketing Consultant, Gotham Artists, when he took a drastic measure to shift his approach toward organic growth:
The biggest risk I took was shutting down all paid ads for a quarter.
Everyone thought I was crazy, but I wanted to test something—how well our business could survive on purely organic strategies and relationships.
I doubled down on content, community engagement, and partnerships instead.
It was uncomfortable at first, but it forced us to focus on quality leads and real connections instead of chasing clicks.
By the end of the quarter, our revenue didn’t just survive—it grew, because we built trust and loyalty in ways ads just couldn’t.
It completely shifted how we approach long-term growth.
Specialized Product Offering
A specific focus can build a brand’s identity and lead to more loyal customers. Matt Little, Founder & Managing Director, Festoon House, shares how narrowing his company’s offerings to one type of product allowed him to thrive in a crowded market:
Deciding to shift from offering a broad range of home goods to specializing solely in outdoor lighting was a huge gamble. At the time, we sold everything from decor to small furniture, and while sales were okay, we lacked a clear identity. It felt like we were just another online store trying to be everything to everyone, and I knew that wasn’t sustainable long-term.
The move to drop all other categories and focus exclusively on outdoor lighting wasn’t without hesitation. There was the risk of losing customers who had been coming to us for our variety. I saw an opportunity to do one thing really well instead of spreading ourselves thin. The decision meant refining our product range, understanding the ins and outs of outdoor lighting, and building stronger supplier relationships to ensure we were offering the best products in the market.
That risk paid off. Focusing on lighting made us known for a specific, high-quality product that met a clear demand. Instead of being just another e-commerce site, we built a reputation for durable and stylish lighting solutions. Sales grew, but more importantly, they became consistent as we developed a loyal customer base that trusted us for that expertise. Narrowing our focus was what allowed the business to really find its footing and thrive in a competitive space.
Targeted Luxury Real Estate
In the competitive world of real estate, standing out often requires bold moves and strategic risks. Samantha Odo, Real Estate Sales Representative and Montreal Division Manager at Precondo, exemplifies this entrepreneurial spirit with her decision to pivot her company’s focus towards the luxury market.
A defining moment for me came when I chose to pivot our strategy to focus on luxury listings in Montreal. It was a bit of a gamble; we were primarily known for mid-range properties, and venturing into luxury was uncharted territory for our team. I spent countless hours researching the luxury market, networking with high-end developers, and understanding the specific needs of affluent clients. While it was daunting, I felt it was essential to diversify our portfolio and tap into a lucrative segment of the market.
The risk paid off in ways I couldn’t have anticipated. Not only did we attract a new client base, but our brand began to resonate with a level of prestige that opened doors to collaborations we hadn’t previously considered. This shift transformed not just our offerings but also our team’s mindset, encouraging everyone to think bigger and bolder. Looking back, that leap into luxury real estate has been one of the best decisions I’ve made, and it continues to shape our trajectory today.
Developed Custom Algorithm
Innovation can be the key to standing out from the crowd. Dinesh Agarwal, Founder and CEO of RecurPost, took a significant gamble by choosing to develop a proprietary scheduling algorithm rather than relying on existing solutions.
One of the biggest risks I took was deciding to build our own custom scheduling algorithm instead of relying on pre-built solutions. Early on, most social media automation tools used standard scheduling methods, and it would have been easier to adopt those. But I saw a gap in the market for a tool that could help users not just post regularly but also recycle evergreen content effectively.
Developing this algorithm meant investing a large portion of our resources into something untested, and it delayed our launch significantly. There were moments where I questioned whether we were going too far down a technical rabbit hole, risking the opportunity to get to market faster.
However, this decision to innovate paid off in ways I couldn’t have imagined. Our custom algorithm became a core differentiator for us. It gave users a feature that truly added value by saving them time and maximizing the reach of their content. This risk of slowing down our initial release to create something unique has ultimately transformed our business, making us a go-to solution for businesses wanting smarter automation, rather than just more posts.
Expanded Service Area
In the realm of business expansion, the decision to go global is often seen as a natural progression for successful companies. However, for Amaury Ponce Business Owner, Ponce Tree Services, this step was taken with a twist that amplified both its potential rewards and risks.
The biggest risk I took was expanding our service area beyond just local jobs to cover the entire DFW region. At the time, we did not have the infrastructure or staff to handle the increased demand, but I believed in the potential for growth. This decision transformed our business by significantly increasing our client base and revenue, allowing us to hire more skilled employees and invest in better equipment. It was a leap of faith, but it ultimately made us more competitive and established us as a trusted name across the region. The risk paid off in long-term growth and stability.
Expanded Globally
In the realm of business expansion, the decision to go global is often seen as a natural progression for successful companies. However, for Ronald Osborne, Founder of Ronald Osborne Business Coach, this step was taken with a twist that amplified both its potential rewards and risks.
The biggest risk I took with my company was expanding internationally while still scaling domestically. It was a bold move because I had to split focus between different markets, cultural dynamics, and regulations, all while managing a team across time zones. It was not without its challenges, but the decision to take the risk opened up new revenue streams and diversified the business, protecting it from local market fluctuations.
This risk also forced me to build a more resilient operational structure and improve communication systems, which ended up making the entire company more efficient. Ultimately, it transformed the business from a regional player into a global one, significantly increasing our reach and growth potential.
Transitioned to B2B
In the dynamic world of marketing, adaptability can be a game-changer. David Holman, CMO of Textun, took a significant risk by pivoting his company’s focus from B2C to B2B marketing.
The biggest risk we took as a company was switching our company from primarily B2C to B2B marketing. We had less experience with B2B marketing, and although the basic principles were the same, I knew it would require a lot of adjustments for our team.
However, we made sure to inform ourselves before the switch, which we made in part because of the more-lucrative opportunities in B2B marketing. By leveraging our B2C skills in this new arena and preparing properly for the switch, we wound up making our company even more successful.
Embraced E-Commerce
In the evolving landscape of home décor retail, Reilly James, Marketing Manager & eCommerce Optimization Expert at William Morris Wallpaper, spearheaded a bold transition from traditional retail to a digital-first approach.
The biggest risk we took was shifting our entire focus to eCommerce and moving away from traditional retail partnerships. When I joined, a large portion of our sales still came from physical stores, and there was a lot of comfort in that—being able to see and feel the wallpapers in person. But it was clear that customer behavior was changing, and people were increasingly browsing, discovering, and buying home décor products online. We decided to take the leap and transition into a digital-first business.
This wasn’t just about setting up a website and calling it a day. It meant rethinking everything, from how we present our products to how we engage with customers. Wallpapers are very tactile and visual, so replicating that experience online was a challenge. We invested heavily in high-quality photography, created interactive tools like a room visualizer, and built a robust customer service team that could answer questions via live chat, helping bridge the gap between the online experience and the in-person one.
At first, there was definitely a fear of alienating some of our existing customers, especially those who weren’t used to shopping online for such a product. But the risk paid off. Not only did we see a significant increase in sales, but it also opened up new markets. Suddenly, we were able to reach customers far beyond the geographic limitations of physical retail. We could connect with wallpaper enthusiasts in other countries who might never have found us otherwise.
Taking Smart Risks for Lasting Growth
In the world of business, every bold decision carries inherent risk, but as these founders demonstrate, those risks often lead to the greatest growth and opportunities for lasting impact. The decisions to specialize, prioritize organic growth, and adopt flexible work models all required these leaders to confront uncertainty head-on. By daring to refine their focus, trust their teams, or prioritize long-term customer loyalty over short-term gains, they paved paths toward resilience and success.
So, what can we take from these stories? First, risk doesn’t mean recklessness; it means looking for calculated ways to stand out. Second, commitment to your values—whether that’s specialization, team autonomy, or ethical scaling—can elevate your brand beyond a product or service and make it a trusted name in its field. And finally, remember that risk and growth are intertwined. When you make choices that align with your mission and invest in the long game, you’re not just building a business—you’re building a foundation for impact, sustainability, and, ultimately, lasting success.