The Stay Ahead Solopreneur
— My Story
Stephen J. Bailey
Young Hustle
I’m the quintessential solopreneur. My journey began at nine years old when I placed candy machines in three local stores and tracked every penny in a journal. Since then, I’ve been a one-person operation by design, hands-on in everything I do. At 19, I saved up enough money to buy my first investment property.
Corporate America
Before becoming a full-time solopreneur, I managed teams across five states. With an Associate’s Degree in Business and a Bachelor’s in Information Technology, I helped my teams digitize operations, build profitable workflows, and foster high-performing results. My employer had their most profitable year under my management since their creation 14 years earlier.
When I realized how much money I was making them versus my pay, I resigned and cashed out my 401(k). Within 18 months, I tripled my previous salary as a full-time solopreneur. By year two, I was managing 30 monthly clients.
Full-time Solopreneur
Since 2006, I have generated a seven-figure income by combining digital marketing (web development, SEO, social media, TV, and radio) with real estate (flipping, investing, and rentals). I have helped companies elevate search visibility, spark real social conversations, and craft brand identities through content and visual media.
I built 150+ websites, created 60,000+ unique social posts, attracted 465,000+ social followers organically, generated an annual social reach of 10M+, and closed $4M+ in real estate transactions. My work has contributed to over $1 billion in revenue for organizations via campaigns, sales, fundraisers, and funding initiatives.
I have received more than two dozen awards, been featured in local and national publications, snuck in a five-year TV career, and had the opportunity to speak publicly for 50+ organizations.
I intentionally stayed “small” because every client deserves personal attention. I have never outsourced my work.
My Transformation
During the pandemic, I burned out hard. When businesses moved online, my 70-hour work weeks grew to over 80, and my life became unmanageable. My work ethic stayed the same, but the world changed. New methods in communication, profitable remote work, and AI emerged. I paid attention and adjusted my approach.
The result was a seven-figure business replacing my six-figure business while working only 25 hours per week. I want others to experience the financial freedom that I now know is possible, with less stress, more happiness, and a life on your terms.
Staying ahead isn’t just a mindset — it gave me financial freedom.
The Stay Ahead Solopreneur’s Notes
Awards & Kudos
2025 Greater Fort Wayne Champions of Change Award Finalist, May 2025
by Greater Fort Wayne
Finalist in “Corporate” category after demonstrating an unwavering passion and commitment to community, a role model making a difference in the lives of others, having made significant contributions that have inspired women to succeed, and made Allen County a better place to live, work, and play
2024 Visitors Guide’s Family & Friends Feature, January 2024
by Visit Fort Wayne
2024 Indiana Tourism Award Winner for Best Visitors Guide that offers travel tips for the Fort Wayne area including Stephen’s top five recommendations of must-try places
2023 He GLOws Feature, December 2023
by Glo Magazine
Glo is a free woman’s magazine with over 20,000 readers for the Fort Wayne area with a mission to provide women fresh, local perspectives that featured Stephen’s work with the Women’s Fund of Greater Fort Wayne
2023 Cover of Annual Book of Lists Magazine, January 2023
by Greater Fort Wayne Business Weekly
The Book of Lists contains all of the Weekly Top Lists published throughout 2022 by Greater Fort Wayne Business Weekly
2022 Celebrating History Feature: Stephen J. Bailey, September 2022
by Fort Wayne Magazine
Fort Wayne Magazine is a source for arts, culture, entertainment, restaurants, and lifestyles with monthly readership of over 65,000 that featured Stephen’s most treasured item
2021 Downtown Achievement Award, September 2021
by International Downtown Association
The Award of Excellence acknowledges an excellent response to an urban place management challenge, demonstrating application of industry knowledge and exceeds the jury criteria
2021 Cover of Indianapolis Monthly Magazine, August 2021
by Emmis Communications
Indianapolis Monthly is Indiana’s general interest magazine reaching 170,000 monthly readers providing readers with compelling narrative stories and smart, lively service pieces about the city’s culture, lifestyle, and more
2021 All-American City Award, June 2021
by National Civic League
Fort Wayne was designated an All-America City after a televised campaign hosted by Stephen J. Bailey that highlighted Riverfront Fort Wayne, Fort Wayne UNITED, and Fort Wayne Community Schools’ Family and Community Engagement Center
2020 Arts United Award Nominee: Outstanding Advocate, January 2020
by Arts United of Greater Fort Wayne
Recognizes an individual, organization, business, or foundation that has made a significant contribution to the promotion or development of one or more arts and cultural organizations in Northeast Indiana
2019 How Your Dinner Table Can Transform Your Community, August 2019
by Input Fort Wayne
The creation of Conversations at Hickory, a dinner series hosted by Stephen J. Bailey to bring strangers together to forge connection and empower human connection around a single topic.
2019 +1 Entrepreneur Interview: With a PH Digital, May 2019
by Steve Franks
+1 Entrepreneur Interviews celebrate Fort Wayne area entrepreneurs who deserve an upvote featuring Stephen J. Bailey of With a PH Digital
2019 Stephen J. Bailey Lives & Breathes Conent for his Marketing Clients, April 2019
by Greater Fort Wayne Business Weekly – Personal Business Feature
Northeast Indiana’s most trusted source for business news, including health care, real estate, technology, government, utilities, legal, sports businesses, the arts community, non-profit organizations and more in the 16 counties of Northeast Indiana and Northwest Ohio
2018 15 People to Know/Watch in Fort Wayne, September 2018
by Fort Wayne Magazine
Inclusion on list of 15 creative and inspiring people in northeast Indiana to know/watch
2018 Reader’s Choice Local TV Personality Nominee, July 2018
by Fort Wayne Newspapers
Nominee in the Readers’ Choice contest to support the favorite local businesses, organizations, people, and attractions
2017 Business Excellence Award for Best Business Blog, November 2017
by Greater Fort Wayne Business Weekly
2017 Greater Fort Wayne Business Weekly Business Excellent Award for Best Business Blog for Northeast Indiana Regional Partnership
2017 Business Excellence Award for Best Use of Twitter, November 2017
by Greater Fort Wayne Business Weekly
2017 Greater Fort Wayne Business Weekly Business Excellent Award for Best Use of Twitter for Northeast Indiana Regional Partnership
2017 Business Excellence Award for Best Website, November 2017
by Greater Fort Wayne Business Weekly
2017 Greater Fort Wayne Business Weekly Business Excellent Award for Best Website for Three Rivers Distilling Company
2016 Business Excellence Award for Best Use of Instagram, November 2016
by Greater Fort Wayne Business Weekly
2016 Greater Fort Wayne Business Weekly Business Excellent Award for Best Use of Instagram for Downtown Fort Wayne
2016 Community Builder Award, July 2016
by Evergreen Leadership Community Builder
Winner of the 2016 Community Builders Award by Evergreen Leadership. 15 leaders from across Indiana received this award based on their commitment to their communities, exemplary workplace leadership, and desire to collaborate with like-minded peers
2015 Indiana’s Most Influential Dude in Social Media, December 2015
by Indiana Social Media Summit
Open voting was completed via Indiana Social Media Summit for nominations – both the nominations and winner were selected by statewide open online voting via the 7th Annual Indiana Social Media Summit
2015 Digital Marketing Award for Best Website Landing Page, June 2015
by Greater Fort Wayne Business Weekly
2015 Greater Fort Wayne Business Weekly Digital Marketing Award for Best Website Landing Page designed by an Agency for Downtown Fort Wayne
2015 Digital Marketing Award for Best Use of Facebook, June 2015
by Greater Fort Wayne Business Weekly
2015 Greater Fort Wayne Business Weekly Digital Marketing Award for Best Use of Facebook by an Agency for Downtown Fort Wayne
2015 Digital Marketing Award for Best Use of Instagram, June 2015
by Greater Fort Wayne Business Weekly
2015 Greater Fort Wayne Business Weekly Digital Marketing Award for Best Use of Instagram designed by an Agency for Downtown Fort Wayne
2015 Digital Marketing Award for Best Use of Photographs, June 2015
by Greater Fort Wayne Business Weekly
2015 Greater Fort Wayne Business Weekly Digital Marketing Award for Best Use of Photographs designed by an Agency for Waiter on the Way
2015 Digital Marketing Award for Best Single Author Blog, June 2015
by Greater Fort Wayne Business Weekly
2015 Greater Fort Wayne Business Weekly Digital Marketing Award for Best Single Author Blog designed by an Agency for Waiter on the Way
2015 Forty Under 40 Award, March 2015
by Greater Fort Wayne Business Weekly
Recipient of the 40 Under 40 Award in Northeast Indiana – Class of 2015
2014 Outstanding Commitment to Downtown Fort Wayne, January 2015
by Downtown Improvement District of Fort Wayne
Award received for the marketing work and promotion connected to businesses within the Downtown Improvement District of Fort Wayne
2014 Indiana’s Best in Show on Twitter, December 2014
by Indiana Social Media Summit for the Downtown Improvement District
Open voting was completed via Indiana Social Media Summit for nominations – both the nominations and winner were selected by statewide open online voting via the 6th Annual Indiana Social Media Summit