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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. He’s grateful he took the leap of faith but the first couple of years were rough and lessons were learned, like how to hire the right people, figuring out how to make use of his greatest strengths, and creating different streams of revenue. Jeff also discusses working through decision fatigue and delegating tasks–while trying not to delegate as much in his personal life.
Support Jeff’s Work-> https://podglomerate.com/
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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 first writing job at MTV, the subsequent imposter syndrome that she had to work against and how she manages it to this day, and how she believes leading with your authentic point of view is the best way to make an impact and find your audience. Sophie also wrote a book, “The One You Want to Marry (and other identities I’ve had),” which pushed her to examine her mental health challenges, including the OCD that she now explores in her one-woman show.
Support My Business -> www.dcpofficial.com
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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 cross-country move, they share how they built a hyper-local following in a place that was completely new to them, and the catchphrase they established that garnered a higher level of interaction and commitment from their community, which continues to grow. They also talk about self-promotion and their differing feelings on how to approach it, and how a stealthy combination of flexibility and boundaries is what helps them get it all done.
Support Carla Marie and Anthony’s Work-> https://www.carlamarieandanthonyshow.com/
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Support My Business -> www.podstreamstudios.com
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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 the things to consider when creating and sustaining inventory. Chris also walks us through two of his most unexpected challenges: selling an American-made product, and translating high-profile visibility in movies like Fast and the Furious into actual sales.
Support Chris’ Work-> https://kitanica.com/
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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 media company producing podcasts and other digital content (she’s also an award-winning podcast host!). Bridget shares her realizations around the concept of job security and how she draws boundaries in order to focus on the things that matter most to her, in business and her personal life. She also speaks to being honest with yourself and others about your strengths and weaknesses in order to elevate your business.
Support Bridget’s Work -> https://www.unbossedcreative.com/
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Support My Business -> www.podstreamstudios.com
Stay updated with our weekly newsletter and join our live monthly Entrepreneur Struggle events by following me on LinkedIn - https://www.linkedin.com/in/chris-colbert-dcp/
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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 what it’s like to delineate responsibilities and recognize each other’s strengths while tackling new challenges, like budgeting and setting fair wages for themselves and their contractors. They also tell us about how they’ve reframed their concept of side hustle and full-time work, how they approach marketing and building their brand, and what it takes to work through disagreements and find a comfortable resolution for everyone.
Support Jen & Chase’s Work-> https://www.blakowndproductions.com/
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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 entrepreneurs with the unique challenges of growing a business. She went from discouraged to thriving through a slow and steady process of shifting her mindset; she realized that her limiting beliefs about herself and her business were the invisible barriers standing in her way of growth. She tells us what resources helped her break free from persistent negativity and perfectionism, and the key mantra she relied on in some of her worst moments of spiraling into doubt. And now that she’s done a lot of healing, she shares how she helps her clients connect their own healing to business growth and success.
Support Chris’s Work-> https://decisionsbydesign.com/
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Support My Business -> www.podstreamstudios.com
Stay updated with our weekly newsletter and join our live monthly Entrepreneur Struggle events by following me on LinkedIn - https://www.linkedin.com/in/chris-colbert-dcp/
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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. She shares the story of how she found confidence in herself and her ability to strike out on her own, how she finds and structures her team, and how she combats imposter syndrome and ultimately delivers for her clients.
Support Catie’s Work-> https://creativebeautycollective.com/
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Stay updated with our weekly newsletter and join our live monthly Entrepreneur Struggle events by following me on LinkedIn - https://www.linkedin.com/in/chris-colbert-dcp/
Support the show: https://www.dcpofficial.com/entrepreneurstruggle
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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 interdisciplinary cultural arts and educational institute. Through her years-long journey in and out of hospitals and doctor’s offices, she decided healing and wellness would be the focus of her life’s work, where she now weaves together arts, activism, and advocacy by conducting training courses on conflict management, resolution, and cultural competency at organizations throughout the country. Ami speaks to how she handles the potential situation where a client is just trying to check their “diversity and inclusion” box without doing the real work, and how she works through resistance within a group. Ami is also an incredible storyteller and shares a few of her favorites, including the time she accidentally called the Dalai Lama “daddy” and when she had to do a news segment alongside the grand wizard of the KKK.
Support Amikaeyla’s Work-> https://amikaeyla.com/
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Stay updated with our weekly newsletter and join our live monthly Entrepreneur Struggle events by following me on LinkedIn - https://www.linkedin.com/in/chris-colbert-dcp/
Support the show: https://www.dcpofficial.com/entrepreneurstruggle
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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 series of harsh burns from faulty product distributors and a scam that lost him $20,000 dollars and some customers. Gathering up the lessons learned throughout his colorful entrepreneurial journey, he set out to build a safer platform to increase access to suppliers in Mexico and other countries, relieving the pressure to source products from China. Raine shares how he’s committed to creating an international standard for suppliers and buyers in a place where they can come together to responsibly source whatever they need to run their own businesses. In the process, he’s not only assisting manufacturers in countries like Mexico, but he’s demystifying the process for those who thought shipping to the U.S. was too complicated and expensive.
Support Raine’s Work-> https://www.zipfox.com/
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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 Perspective, a business consulting company. Alisha explains how through a lot of trial and error, and attempts at replicating successful processes across different industries, their growth was happening in the “unsexy” stuff and identifying that helped them communicate what they have to offer and why they’re different from their competitors. Alisha also shares her three-step method to beating her persistent imposter syndrome and how it’s helped elevate her to the Inc. 5000 list and a seat on the Forbes Business Council.
Support Alisha’s Work-> www.penningtonperspective.com
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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 this time, do it together. They discuss the difficulties of running a school during a pandemic, how they came together to work with parents and earned their trust and loyalty, and how they navigate making unpopular judgment calls when they know it’s best for the business. Najee and Sesealy also share what it’s like to run a business as a husband and wife duo with three kids at home, and how they are demonstrating for their kids the freedom and possibilities that entrepreneurship can provide, with the hope that they’ll one day grow the family business that they now refer to as the House of Owens.
Support Their Work-> https://www.decaturmontessori.com/
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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, his very own recruiting and talent acquisition firm. It was a challenging start with waves of uncertainty and sacrifice, and Tim went three years without collecting a paycheck, but his strategic planning and steadfastly loyal core team allowed them to endure the roughest times, and just last year they brought in more than $20 million dollars in revenue. Tim explains how he broke out of a scarcity mindset in order to better manage the financial side of business, why he offered equity to the employees who joined before it was a “sexy company,” and how pushing through the pandemic taught him to remain even-keeled, no matter the upswing or downturn.
Support Tim’s Work-> https://lucasjamestalent.com/
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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. April has since founded Revolutionize Hollywood and RevHo House, two different sources for creative talent and space. She talks about finding patience through developing long-term strategy as she built her dream vision for RevHo House, why she never works without a team, and why that team no longer consists of her family members or close friends. She also shares a piece of advice from Nick Cannon’s dad that changed her perspective on creative output, and how she manages her imposter syndrome and commits to the idea that she is enough. And somehow, April also found the time to write a book, “Blahom,” a fantasy fiction novel.
Support April’s Work-> https://blackhollywoodmarilyn.com/
Support April’s Work-> https://revhohouse.com/
Support April’s Work-> https://www.revolutionizehollywood.com/
Buy April’s Book-> https://www.blahom.com/
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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 businesses. Since she found her sweet spot, she’s learned some crucial lessons from fielding rejection and how it can inform future pitches to publications, as well as her approach to her clients. She also details the key differences between PR and marketing, what large PR firms get wrong, how her business avoids those pitfalls, and how Light Years Ahead took the challenges from the COVID-19 pandemic and turned them into the greatest profits they’d ever seen. Bonus: she tells the story about how one ad placement for a hotdog turned into a quarter million dollars in profits.
Support Megan’s Work-> https://www.lightyearsahead.com/
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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 versus quantity as the cornerstone of his creative process, and how he gets clients to open up to the camera and show their true selves. Ray also gives much credit of his success to his faith, as it bolsters his confidence and gratitude.
Support Ray’s Work-> https://www.headshotspecialist.com/
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Stay updated with our weekly newsletter and join our live monthly Entrepreneur Struggle events by following me on LinkedIn - https://www.linkedin.com/in/chris-colbert-dcp/
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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, navigating the ins and outs of a bi-coastal industry with high demands and expectations. He details how he manages boundaries with clients and industry professionals, how he carved out his space as a trusted source for talent in Atlanta and the industry at large, and what it’s like to be the boss of his own big brother.
Support Jacob’s business -> http://www.privilegetalentagency.com/
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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 following your dreams–even the ones that aren’t profitable–and how the milestones in Keyia’s businesses have allowed her to realize that she is becoming Black history. She shares the advice she received that changed her whole approach to success, how meditation elevated her life, and the peaks and pitfalls of working with family and loved ones.
Support Keyia's business -> https://www.eatfishnet.com/
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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 music industry and freelancing as a content creator and editor, which confirmed that, in order to succeed, you’ve got to fail along the way. Now he runs Stay Bien Films with an arsenal of (sometimes hard) lessons learned, like knowing when to turn away a potential client, the benefits of proper delegation, overcoming creative resistance, and perhaps, most importantly, how to give yourself grace.
Support Esteban’s Work-> https://www.staybienfilms.com/
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“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 life and business and now teaches others how to lead and launch businesses with joy. She explains what it really means to infuse joy into even the most stressful business practices, like funding the payroll, and how to survive late-stage capitalism while maintaining joy and humanity. To learn about the latter, make sure to sign up for the waitlist for Quinn’s upcoming course, Joy and Money Mindset, linked below.
Support Quinn’s Work-> http://www.joybasedbusiness.com/
Sign up for Quinn’s Course -> http://www.joybasedbusiness.com/waitlist
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