The journey to business ownership isn’t always a straight path. It's filled with unexpected twists, lessons and opportunities. Jennifer Trowbridge, co-founder of RedTree Investment Group, offers a prime example of how business growth strategies evolve from personal experiences, career shifts and willingness to take risks. Keep reading to learn how a mishap in college scheduling, unexpected calls to colleagues and joining the Entrepreneur’s Organization changed her trajectory.
From Unexpected Beginnings to Financial Expertise
Jennifer’s plan wasn’t to work in finance or the business world, let alone become an entrepreneur. She started her college career as a pre-pharmacy student at Xavier University. An unexpected scheduling error that would have required her to spend another year in school pushed her to switch to a business major. This pivotal moment set her on a new path that led her to finance and, eventually, entrepreneurship.
She dove headfirst into the world of finance upon graduating college. Starting her career at Fifth Third Bank, she quickly absorbed vital industry knowledge. She also learned her first important lesson: the power of negotiation. A colleague with the same qualifications secured higher pay simply because he knew to ask. This experience taught her how important it is to know your worth and be strategic in all business decisions.
Jennifer’s experience at the bank illustrates a key business growth strategy: to develop industry expertise before launching a business, whether it's through education, corporate experience or mentorship.
Learning Through Corporate Experience
During her time with Fifth Third Bank, Jennifer filled multiple roles, gaining insights into finance, management and business operations. However, she realized that corporate culture wasn’t for her. The long hours and rigid environment combined with the cutthroat atmosphere of finance made her question if the finance industry was where she truly belonged.
Based on her background, she advises young professionals to take time to learn what they like to do but also what they don’t want to do. Those preferences are key pieces of information to leverage in future roles.
The next business growth strategy: Use early career experiences to identify your strengths, weaknesses and long-term goals, which can guide your subsequent business decisions.
Taking the Leap Into Entrepreneurship
After a decade in corporate finance, Jennifer was ready for a change and contemplating her next steps when a serendipitous phone call accelerated her transition: A recruiter called to offer her a job.
Before making her decision, Jennifer reached out to a former colleague she trusted. That conversation took her on a completely different path that eventually led to the two of them starting RedTree Investment Group. Reaching out to her former coworker changed her entire life.
The third key business growth strategy is to always leverage your network. You may gain unexpected opportunities that wouldn’t have been available otherwise.
The Challenges of Building a Business
Jennifer and her colleague worked together for a while before buying out the business. Starting the business wasn’t easy, Jennifer says, and the first five years were the hardest. They required long hours, financial discipline and resilience. She quickly learned that entrepreneurship meant more than just having expertise in finance. It requires strong leadership, cash management and the ability to scale efficiently.
One of the biggest challenges she faced included managing cash flow effectively to sustain operations, building the right team and learning how to delegate to prevent burnout.
She realized that just because she could do something herself, didn’t mean she had to. By trusting her team and focusing on high-impact decisions, she was able to successfully scale her business.
The fourth business growth strategy? Invest in cash management and the right hires, and delegate to ensure your growth is sustainable.
Finding Support and Scaling the Business
One of the biggest turning points in Jennifer’s journey was joining the Cincinnati chapter of the Entrepreneurs’ Organization (EO). Through EO, she was able to connect with like-minded business owners and gain mentors and peers who continue to provide invaluable guidance.
“It’s almost indescribable just the bond that you have with people. There’s the kind of the adage that it’s lonely at the top. Those adages exist for a reason. It is lonely at the top. Family and your friends love you, support you, but they don’t truly get it unless they own a business,” Jennifer explains. Entrepreneurship can be isolating, but having that community and guidance from EO Cincinnati has been a key factor in her success.
Another valuable business growth strategy is to surround yourself with mentors and a strong entrepreneurial network. By doing so, you can gain invaluable advice and support from a trusted group of peers when challenges arise.
Achieving Flexibility and Long-Term Success
After years and years of hard work, Jennifer is now enjoying what she has always wanted – flexibility and control over her days and career. Her schedule is structured in a way that works for her, her business and her family. But this didn’t happen overnight, it took years of strategic planning and finding a team she trusted to reach this point. She credits learning the power of delegation and leadership that were essential for her business success and flexibility.
By building a self-sustaining business, businesses are able to grow without their leaders sacrificing work-life balance.
Key Takeaways for Aspiring Entrepreneurs
Jennifer’s journey from pre-pharmacy student to corporate finance to entrepreneurship proves that success isn’t about having the perfect plan. It comes from being adaptable, making strategic decisions and surrounding yourself with the right people.
If you’re looking to grow a business, here are Jennifer’s top tips:
Be open to career pivots. Sometimes, the best opportunities come from unexpected changes.
Gain experience first to learn an industry and its challenges before starting your own business.
Leverage your network because connections can open doors to new opportunities.
Master cash flow management to build scalability and sustainability.
Invest in mentorship and networking from organizations like EO that provide invaluable guidance.
Jennifer’s story is proof that business growth strategies aren’t just about numbers — they’re about adaptability, resilience and the willingness to take risks.
Are you an entrepreneur looking to connect with like-minded business owners? Join EO Cincinnati and gain access to a supportive network that helps businesses thrive.