Entrepreneur Struggle

Jeff Umbro had a successful podcast, but he couldn’t get a job at a podcast company–so he decided to create his own. Jeff is the founder of The Podgolmerate, a company that produces, distributes, and monetizes podcasts. He went from not getting hired to now running his business with nine full-time employees, representing anywhere from 70 to 80 shows at a time, and having been profitable since 2018...

Sophie Santos was just a kid when she saw Lindsay Lohan in “The Parent Trap” and thought, I can do that. Now she’s an accomplished comedian, writer, and actor, whose one-woman show, “Sophie Santos…is Codependent,” is now playing in Edinburgh, which finds her confronting her personified OCD after a break-up. She talks about getting her feet wet as a student at the Upright Citizen’s Brigade and her...

Carla Marie and Anthony started out in terrestrial radio and spent years together on the syndicated NYC-based Elvis Duran and the Morning Show, during which they started their first podcast together back in 2014. Now they’re hosts of The Morning Show Podcast, which recently joined Gemini XIII’s Personality Network, and The Carla Marie and Anthony Show, which airs live on Twitch. After making the c...

Chris Cronin used to cobble together his own bikes with parts from the town dump, and now his company’s products appear in blockbuster movies and on stars like The Rock. Chris is the co-founder of the family-operated clothing and apparel business Kitanica, and he shares the challenges of learning to scale their production, how they evolved the types of products they have made over the years, and t...

Bridget Todd was feeling disengaged from the content she was producing, but was inspired by her students at Howard University who were empowered by the hope and possibility of changing the world through sharing across our social media networks. Bridget reconsidered how she could create a career that intertwined with her activism, and that resulted in her opening Unbossed Creative, a mission-driven...

Chase Parker was in pursuit of another creative mind working on a short film project, so he turned to his friend (and DCP Executive Producer) Jen Brown to see if she was up for it. They didn’t know it at the time, but their collaboration was the beginning of BlakOWND Productions, which they have since co-founded, where they set out to tell Black stories with innovation and creativity. They discuss...

Chris Atley was just a freshman in high school when she had a poor experience with a discouraging teacher–and she internalized it with a message that she was not good enough. Chris has since flipped that narrative on its head, and is a successful coach, speaker, author, podcast host of “One Simple Truth,” and founder of Decisions by Design Coaching, where the goal is to specifically help female en...

Catie Wiggy couldn’t figure her skin out–so she turned to the professionals and it changed her life. Now she’s the professional improving people’s lives in the clean beauty industry, where clients turn to her for creative marketing and brand consulting. Catie is the founder of two companies: Posh Artistry and Creative Beauty Collective, a boutique firm focused on supporting clean beauty brands. Sh...

Amikaeyla Gaston was out having one final celebration before heading to medical school–but tragedy struck when she was the victim of a hate crime and it changed the course of her life. Now, after years of healing inside and out, she’s living the life of a socialpreneur, as the Founder and Executive Director for The International Cultural Arts and Healing Sciences Institute (ICAHSI), a contemporary...

Raine Madhi wrote a note to himself when he was first starting out: build the platform you wish you had when you started. From where he sits now, he can see he did exactly that. Raine is the founder of ZipFox–along with a laundry list of other businesses he’s created since childhood, like selling donuts at school and pushing products in AOL chat rooms–a company he was inspired to create after a se...

Alisha M. Pennington graduated with her master’s degree in 2011 and into an economy that was still struggling from the recession that hit hard in 2008. The gig economy hadn’t been fully realized yet, but with the ever-present need to create income, she started working her way into that space, and over time that developed into her two businesses: ATvantage Athletic Training, and Pennington Perspect...

It started with a need to find a good school for their daughter, and it became their most successful entrepreneurial endeavor. Sesealy and Najee Owens are the owners of Decatur Montessori School, a business they acquired in the midst of COVID-19. Sesealy and Najee’s respective business ventures had failed to take off, so they decided to rethink their approach and acquire an existing business, and...

When Tim Schumm graduated from college, he was stumbling over what he should do next, when he was offered an opportunity to join a recruiting firm. He spent the next ten years there wearing every hat available, learning and steadily climbing the ladder while remaining quietly passionate about his desire to strike out on his own–until he did exactly that when he founded Lucas James Talent Partners,...

April Russell’s story begins on the streets of Los Angeles, where she worked as a performer and created the character Black Hollywood Marilyn. April’s corporate background had her looking at her creative pursuits from a business perspective, and after trademarking her character, she became what she calls an “artrepreneur”--a person who connects their artistic passions with a business mindset. Apri...

When Megan Brown Bennett set out for a career in public relations, she jumped right into a position working with A-list celebrities–and quickly realized, that type of PR wasn’t right for her. She switched gears and worked her way to where she sits now, as CEO and President of Light Years Ahead, a full-service boutique public relations agency that specializes in products, brands, and small business...

Ray Singh runs three businesses but his core passion lies within his day-to-day operations of Headshot Specialist. It started humbly, as Ray navigated a call from his intuition that told him it was his purpose, and through small incremental movements and progress, he built his dream photography business. Ray shares how he worked through the anxieties of being an amateur photographer, using quality...

Jacob Lawson’s story begins with a bit of serendipity, when a stranger appears and changes the course of his life with a simple offer. That moment kicked off the journey that led him to his current role as the owner and lead agent of Privilege Talent Agency, working with actors across Southeast America. After years as an agency employee, Jacob was able to buy out the owner and now he runs the show...

Keyia Yalcin is the founder of the Yalcin Group, the Baltimore restaurant Fishnet, and she's a real estate agent, but the longest title she’s held is my sister. This throwback episode is a chance to get acquainted with the strong entrepreneurial spirit in my family, as Keyia and I look back on her more than 10 years in the restaurant industry and beyond. We get into the discomfort and rewards of f...

The business of creativity requires a delicate balance, but Esteban Obregon has found his stride. Esteban is the founder of Stay Bien films, a hybrid production house and marketing agency that succeeds in offering their clients a fusion of killer video content and savvy business strategy. Before setting up his own shop, he gained invaluable experience working as a performer and manager in the musi...

“COVID just wiped out my business basically, and the awesome stuff happened after that.” Quinn O’Briant’s perspective is unique, but she’s earned it. Quinn is the founder of Joy-Based Business, which came after the pandemic crushed her consulting business. But she’d be the first to admit that if COVID hadn’t brought her company to its knees, burn-out was close behind. Quinn restructured her own li...

What do you do in your darkest moments, navigating situations you never thought you’d find yourself in? As an entrepreneur, Anna DeShawn doesn’t have time to run from her challenges, so she digs deep into faith and intuition–and a little help from a licensed therapist. Anna is a multi-faceted founder of E3 Radio and The Qube, as well as host of the award-winning Queer News podcast. While it’s amaz...

Getting fired undoubtedly sucks–but what’s it like for the person who has to do the firing? Entrepreneur Struggle is back, powered by the LinkedIn Podcast Academy, and I’m joined by DCP Entertainment’s Chief Operating Officer Adell Coleman to talk about the discomfort and challenges of firing and laying off employees. Sometimes it’s the wrong fit, sometimes the roles change, sometimes they’re just...

It has been incredible having these conversations and learning about the various challenges entrepreneurs face, while getting some tips to help us along our own business journey. Today's episode marks the end of Entrepreneur Struggle for now, but please go back and listen to some our past episodes and email us at info@dcpentertainment.com if you'd like us to bring back the show.   Special thank yo...

Alex Hyde-White is an actor whose starred in movies like “Pretty Woman”, “Catch Me if You Can”, and the controversial Netflix series, “Monster: The Jeffrey Dahmer Story”. But he is also the author of the memoir, “In The Volume”, and he’s the founder of the audiobook studio, Punch Audio. In this conversation we talk about the journey he took going from acting to running an audiobook studio, his tip...

Martina San Diego is a singer-songwriter, teacher, and the founder of the Martino San Diego Music Studio. I’m excited for you to hear our conversation about working through those inconvenient creative mental blocks, finding the emotional balance in our work, and Martina’s tips on how to be authentic and successful in your artistry.   Support Martina’s Work-> www.martinasandiego.com  Support Martin...