The 50 Bosses Deep Business Conference is coming to Indy this fall.
50 Bosses Deep — which stands for 50 Bossed Dedicated to Elevating Economic Prosperity— takes place Oct. 11-12 at The Alexander Hotel and features resources and workshops for entrepreneurs and creatives, presentations by industry leaders and a pitch contest for business owners.
The Recorder sat down with Shara Bowling, president and founder of 50 Bosses Deep and CEO of Global Tax Service, ahead of the conference to discuss her inspirations, the importance of generational wealth and empowering others business leaders.
This interview was edited for clarity.
Tell me about yourself. Where did you grow up and go to school? How did you become an entrepreneur?
Bowling: I grew up on the Eastside of Indianapolis on 44th and Arlington Ave. I graduated high school from Lawrence North. I went to college at Jackson State and Indiana Wesleyan University. I became an entrepreneur because I needed to solve a problem. My mother was downsized after 27 years of service at her job, and I felt it my obligation to do something to help her. So, I created my first business Share a Hand Cleaning in 2004.
Was this always your dream? What is your dream now?
Bowling: No, this was not always my dream. I never WANTED to be a business owner. In fact, it was never my dream. I wanted to be A&R for a record label and on the flip side be a nurse and work in healthcare administration.
What inspired you to start and run your own business, Global Tax Service?
Bowling: I have an entrepreneurial spirit and have started several businesses over the years. Whenever I see a need or a problem, I’m driven to find a solution — and that’s how my businesses are born.
I founded Global Tax Service in 2016 because I recognized a significant gap in competent and accessible tax and business services, especially within the African American community. Through my work and interactions with numerous small business owners, I observed a common issue: a lack of accessible and relatable information on taxes, bookkeeping, and business management.
I decided to address this by placing a strong emphasis on tax education, knowledge, and expertise—areas that have often been overlooked in the African American tax industry, where the primary focus has been on securing refunds rather than understanding the broader tax landscape. In response, I developed several educational platforms, hosted free workshops, and provided advisory services, all aimed at empowering individuals and business owners with the knowledge they need to succeed. My goal with Global Tax Service is not just to help people file their taxes, but to equip them with the understanding to manage their finances effectively and sustainably.
Our slogan is “what we do for the community can change the world.”
How did you know, in each stage of your career, when it was time to move on to something bigger?
Bowling: The decision to move on is ultimately a blend of careful reflection on your skills, goals and the opportunities around you, along with the courage to embrace change and take calculated risks. Some key factors include mastering the current role I was in, feeling stagnant, my vision became larger, opportunities align themselves and just trusting my intuition.
What was the inspiration behind starting the 50 Bosses Deep conference?
Bowling: 50 Bosses Deep was created to support entrepreneurs, particularly disadvantaged and African American business owners, by helping them overcome hurdles and providing a network of genuine support. Entrepreneurship isn’t always glamorous — many businesses are struggling and need real solutions. This platform connects entrepreneurs nationwide, offering guidance, sharing insights and fostering understanding. What sets 50 Bosses Deep apart is our holistic approach: we focus on the entire entrepreneur, addressing both business needs and personal well-being, including family, mental health and relationships. We also provide practical programs on wealth building, tax management and increasing revenue to help entrepreneurs thrive both personally and professionally.
Why is it so important to you to do this work?
Bowling: Wisdom and knowledge are meant to be passed down, not held captive. The struggles I’ve faced and the success I’ve earned have taught me valuable lessons, and I believe it’s my responsibility to share those with others. Everything I’ve been through — every challenge, every victory — wasn’t just for me. It’s about helping others avoid the pitfalls I encountered and giving them the tools they need to succeed. Knowledge should flow freely because that’s how we lift each other up and create a community where everyone has the chance to thrive.
The 50 Bosses Deep conference covers areas of wealth building, funding and lending, as well as health and fitness. Why did you feel it was important to include all these topics in one conference?
Bowling: Including topics such as wealth building, funding and lending and health and fitness in the 50 Bosses Deep conference is important because they all play a crucial role in holistic success for entrepreneurs and business leaders. Wealth building ensures that attendees can grow and sustain their financial assets, while funding and lending provide the necessary capital to scale their businesses. Health and fitness are equally essential, as maintaining physical and mental well-being is key to performing at a high level, making sound decisions and leading effectively. By addressing all these areas in one conference, participants can gain a comprehensive toolkit to achieve long-term success in both their professional and personal lives.
Who is this conference for? Who will benefit from the speakers, workshops and knowledge being shared there?
Bowling: The 50 Bosses Deep Conference is for ambitious entrepreneurs, business leaders, and professionals seeking to elevate their success. It’s ideal for those looking to scale their businesses, secure funding, build wealth and integrate health and wellness into their leadership. Whether you’re an aspiring entrepreneur, established business owner or professional in transition, this conference provides the tools and strategies needed for holistic growth and long-term success.
What is one piece of advice you would give to your younger self and other aspiring entrepreneurs?
Bowling: Absolutely and unapologetically know your worth and believe in it. As an entrepreneur, it’s essential to have confidence in the value you bring to the table. Don’t undersell yourself or your ideas out of fear or doubt. Stand firm in your skills, knowledge and the unique contributions you can make. When you truly believe in your worth, others will too, and that confidence will help you negotiate better deals, attract the right opportunities and build a business that reflects your true potential.
The 50 Bosses Deep Business Conference takes place Oct. 11-12 at The Alexander Hotel, 333 S. Delaware St. For more information or to purchase tickets, visit 50bossesdeep.com.
Contact Arts & Culture Reporter Chloe McGowan at 317-762-7848. Follow her on X @chloe_mcgowanxx.
