In October of 2019, after more than 20 years working for someone else, I took the plunge into Nashville’s entrepreneurial world. I resigned from a top corporate communications job, leaving behind the structure and comfort of corporate life to build something of my own. Then, just months later, the world shut down due to COVID, and I found myself navigating startup pressures in the middle of a global pandemic.
Five years later, I’m proud to say we’ve not only survived but thrived. We’ve earned the trust of amazing clients to solve their most complex challenges, built a passionate team that believes in our mission, and filled a wall with awards recognizing our work.
We don’t have it all figured out, and we certainly don’t have the perfect model, but we’ve learned some serious lessons along the way. For anyone in Nashville’s entrepreneurial community who is thinking about making the leap—or those who already have and are seeking fresh perspective—here are five lessons I’ve learned as we celebrate five years of hustle in this great city.
1. Your Network is Your Net Worth
Relationships built over decades have opened doors to new business, partnerships, and invaluable advice. But like many cities, in Nashville, connections are key. The city’s supportive and collaborative business environment has played a big role in our success. Ongoing networking is essential, whether it’s through local events, casual conversations, or programs hosted by organizations like the Nashville Entrepreneur Center (EC).
Nashville’s close-knit business community fosters a “help each other” mentality. That’s why I always ask, “Who do you know that I should know?” The more you give back to your network, the more you’ll gain in return.
2. Jump Feet First and Embrace Vulnerability
Starting a business anywhere, let alone during a pandemic, requires resilience. Imposter syndrome is real, but in Nashville’s business community, you’re not alone. People here understand the challenges of entrepreneurship and are eager to help each other succeed.
You’ll often wonder if you’re ready or if you’re making the right decisions. But it’s about jumping in, trusting your instincts, and learning by doing. In the early days, it felt more daunting, but with every bold move, confidence grew. And I’ve learned that Nashville is a city where taking risks is rewarded with new opportunities.
3. There’s No One Playbook—Create Your Own
In the corporate world, there’s a playbook for everything. But when you’re running your own business, it’s about creating your own path. What worked in corporate won’t necessarily work in your entrepreneurial journey, and that’s okay. The great thing about entrepreneurship is that other business owners are often willing to share their best tools, templates, and contacts.
At Tiny Mighty, we’ve taken lessons from other business owners, mentors, and even clients, and built a unique approach that works for us. Use those resources to build something that reflects your unique vision and values. Take what works for you, but don’t hesitate to shape your own rules. You’ll find that creating your playbook can be the most empowering part of the journey.
4. Invest in the Right People and Continuous Learning
Building a business is an ongoing learning process, and success depends not just on resources, but on the people you bring on board. In Nashville, we’re fortunate to have resources like the Nashville EC and professional groups like Entrepreneurs’ Organization (EO) that provide invaluable support to entrepreneurs. But just as important is hiring the right team—people who believe in your mission and complement your strengths. Continuous learning, whether it’s through local events, industry thought leaders, or fellow entrepreneurs, is also essential for business survival. Investing in both your growth and your team’s will always pay off.
5. Myths Are Made to Be Busted: Challenge Conventional Wisdom
Starting a business is hard, and the statistics—most businesses don’t make it past their first year, and even fewer break a million in sales—can feel daunting. But those numbers don’t have to define your path. Nashville has shown me that success is possible, even against the odds. The entrepreneurial spirit in Middle Tennessee thrives on challenging conventional wisdom and rewriting the narrative. There’s no set formula for success, but with hard work, perseverance, and the right support, anything is possible. By pushing boundaries, staying focused on your vision, and believing in your approach, you can defy the odds and build something truly meaningful.
The Bottom Line
Transitioning from corporate life to entrepreneurial hustle requires risk, adaptability, and ongoing learning. In Nashville, this journey is made even more rewarding by the city’s supportive business community and resources. It’s about creating your own rules, trusting your instincts, and building something meaningful that reflects your unique vision. For those ready to bet on themselves, Nashville is the perfect place to do it—here, the possibilities truly are endless.
The Author
Paul Oakley is an invaluable advisor for organizations seeking to engage key stakeholders who matter most. For nearly 25 years, he managed PR, public affairs, sustainability, corporate and marketing communications programs for a range of domestic, international and global brands. Oakley honed his skills working with nonprofits, start-ups, mid-cap companies and Fortune 50 leaders. Oakley earned his reputation delivering award-winning results and building high-performance agency and in-house communications teams worldwide. He lived and worked in the United States, Europe and South America, and worked extensively in Asia.