The Diary of a Side Hustler

Kayla Brooks
  • 5.0 (1)
  • Entrepreneurship
  • Updated Weekly

Whether pursuing a passion project or passive income, over 40% of Americans have a side hustle. The Diary of a Side Hustler shares the personal stories of small business entrepreneurs who turned their passions into an opportunity for profit. Their stories share personal reflections on both the grind and the glory of balancing life, multiple jobs and everything in between.

Episodes

  1. EP 8: The Diary of Montez Hymon: The Price Paid for Privacy

    06/02/2025

    EP 8: The Diary of Montez Hymon: The Price Paid for Privacy

    In this flavorful episode of The Diary of a Side Hustler, we step into the high-heat world of private catering with Executive Chef, Montez Hymon (affectionately known as Chef Tez). From early kitchen inspiration to serving exclusive dinners for VIP clients, Chef Tez takes us through the journey of initially selling plates to plating perfection in the homes of high profile clientele. Montez's journey to success has been fueled by hustle and determination—promoting his business through networking, handing out business cards, and advocating for himself while juggling other jobs. With six years of experience, Chef Tez has built a highly profitable private catering company that offers unforgettable dining experiences in homes and even on private jets. Whether you’re a foodie, aspiring entrepreneur, or side hustler hungry for inspiration, this episode is a feast for the ears. (due to technical difficulties, there is not a full video available for this episode) --- What You’ll Learn in This Episode: How Chef Tez got into the world of private catering from initially selling plates in college  Tips on how to go about building a high-profile client base  Sacrifices made in order to be a private chef and the time commitments required Practical ways to start building a business through learning from others and saving money  --- Connect with Chef Tez Instagram: @Chef__tezz Website: www.cheftezcatering.com Booking & Inquiries: cheftezcatering@outlook.com --- Don’t forget to subscribe, rate, and review The Diary of a Side Hustler wherever you listen to podcasts. Follow us on Instagram @diaryofasidehustler for behind-the-scenes content and updates! --- Got a side hustle story worth sharing? DM us on Instagram!

    1 hr
  2. EP 7: The Diary of Reggie Pharr: Knowing When to Flip

    05/27/2025

    EP 7: The Diary of Reggie Pharr: Knowing When to Flip

    In this episode, we sit down with Reggie Pharr, owner of BSKix, who’s been in the sneaker flip game for over 17 years—long before StockX and GOAT made it mainstream. But that’s only half the story. By day, he’s a firefighter, risking his life to protect others. By night (and sometimes at 4 a.m. drops), he’s hunting heat and flipping pairs that pay. We talk about the flips that flopped, the ones that changed everything, and how the hustle of reselling sneakers parallels the pivot of switching careers. Whether you’re deep in the resale trenches or figuring out your career path, like Reggie as he learned how to code, this episode has something for you.  👟 What You’ll Hear In This Episode: His first flip: a pair of sneakers he took from his sister’s room What’s changed in the sneaker resale world since he started The sneaker drop that made more money than he imagined Thoughts on when to walk away from a job—or a shoe Advice for anyone trying to flip their way to freedom or transition careers 🔥 Whether you’re flipping kicks or flipping life chapters, this episode is for you. — 📲 Follow the Guest:@bskix (Instagram) 🎧 Like what you heard?Leave a rating, follow, and share this episode with someone who’s thinking about making a big flip. #SneakerReseller #SideHustleStories #FirefighterLife #CareerPivot #What’sYourNextFlip #TheDiaryofaSideHustler #Entrepreneurship

    48 min

  3. 05/12/2025 ·  Bonus

    Journal Entry: Life is Messy

    Today’s Journal Entry Prompt: What is a messy area in your home, business, workplace or life? We’re switching up the style this week and our host, Kayla, is responding to a journal entry prompt and talking about how life gets messy - literally and figuratively. Tune in to hear her share unfiltered thoughts on managing the complexities of trying to thrive at home, work, business, and life.

    13 min
  4. EP 6: The Diary of Camille Hughes: Framing Life, Love and Passions

    05/05/2025

    EP 6: The Diary of Camille Hughes: Framing Life, Love and Passions

    On this episode of The Diary of a Side Hustler, we sit down with Camille Hughes, the founder of The Frame, a dynamic photography and creative studio with locations in Charlotte and Winston, NC!  Originally from Charlotte, Camille's journey took her from studying International Relations at North Carolina State University to finding her true calling behind the lens. Inspired by personal experiences with anxiety, love, and travel, she bought a $300 camera at a pawn shop, and the rest was history. As a self-taught photographer with 10 years of experience, Camille is a storyteller at heart, always seeking beauty in the ordinary. Now, she spends most of her time operating The Frame's two studios and co-managing Pink Broccoli, a cannabis lifestyle brand promoting health and wellness. Tune in to hear Camille's inspiring journey and her passion for creativity and community. 🌿✨ In This Episode, You’ll Learn: What it’s like to transition from operating as a full-time creative to running a brick-and-mortar business  Advocating for yourself and your vision when others’ dont see the vision Finding your passion amidst break-ups and mental health difficulties  Dating as an entrepreneur and making time for each other  Navigating the cannabis industry and beaking into the market as a Black woman  Listen now and get inspired to find your own creativity, in frame. If you enjoyed this episode, please subscribe, rate, and review! Share this episode with someone who needs inspiration to take their own side hustle to the next level. Connect with Camille Hughes: Instagram The Frame Pink Broccoli Connect with us! ⁠Instagram

    50 min
  5. EP 5: The Diary of Breanna Powell: Master’s of Social Work and Social Communities

    04/28/2025

    EP 5: The Diary of Breanna Powell: Master’s of Social Work and Social Communities

    What happens when life forces you to take a leap of faith, and that leap transforms into a thriving business? In this episode of The Diary of a Side Hustler, we meet Breanna Powell, a multi-passionate entrepreneur and content creator based in Durham, North Carolina. As the founder of The Social Hive, a Black woman-led social media management agency, Breanna’s journey began when she made the bold decision to leave her stable job as a program manager after being presented with an unreasonable ultimatum. With no plan and a heavy dose of anxiety, Breanna turned her passion for creativity and community into a full-fledged business that now serves numerous clients and supports other women of color through her all-women team. But Breanna’s creative reach doesn’t stop there. She’s also the visionary behind the Busy Creative Mixer, a celebrated networking event designed to redefine traditional networking by fostering genuine connections among creatives, community curators, and corporate leaders. And if that wasn't enough, Breanna is also the force behind The Busy Step, a high-energy aerobics class blending dance moves, dope music, and a welcoming community. Breanna's entrepreneurial journey is proof that sometimes, the biggest blessings come from the most unexpected challenges. From having her first client fall into her lap to building a supportive network of clients and fellow entrepreneurs, her story is an inspiring reminder that faith, resilience, and community can take you further than you ever imagined. In This Episode, You’ll Learn: How Breanna’s social work background shaped her approach to social media management and community-building. The story behind her abrupt career pivot and how she launched The Social Hive with just one client. Why she believes entrepreneurship is a calling and how faith plays a central role in her journey. The unique way Breanna curated the Busy Creative Mixer to cater to both introverts and extroverts. How she overcame her dislike for bookkeeping by outsourcing the task to focus on what she does best. The birth of her empowering movement “We Got Clothes at Home” and how it's helping people find creative inspiration in their own closets. Her candid reflections on the ups and downs of entrepreneurship and why quitting is never an option. Listen now to discover how Breanna Powell turned life’s curveballs into a thriving creative empire — and how you can, too! If you enjoyed this episode, please subscribe, rate, and review! Share this episode with someone who needs inspiration to take their own side hustle to the next level. Connect with Breanna Powell: LinkedIn Instagram: @bythesocialhive @thebusybre Connect with us! ⁠Instagram

    55 min
  6. EP 4: The Diary of Ja'Mya Giles: Passion Always Comes First

    04/14/2025

    EP 4: The Diary of Ja'Mya Giles: Passion Always Comes First

    What happens when creativity, community, and hustle collide? In this episode of The Diary of a Side Hustler, we meet Ja’Mya Giles — a cybersecurity analyst by day, entrepreneur by night, and community builder always. Originally from River Rouge, Michigan, Ja'Mya's story is proof that your passion projects can become purpose-driven businesses and that side hustling can be about way more than just making money. From almost joining the Marines to landing a cybersecurity career after attending a STEM camp, Ja'Mya’s path has been anything but traditional. But one thing has stayed the same — her commitment to giving back. Today, she’s the founder of Village to Village Leadership Foundation, a nonprofit focused on youth mentorship and scholarship, and the owner of Mya Made Customs, a growing custom apparel and gifting business. Both are built from a heart for community and a love for creativity. In This Episode, You'll Learn: How Ja'Mya discovered cybersecurity (spoiler: ROTC & summer camp played a role) How word-of-mouth grew her side hustle into 60+ orders a month (with no website!) The story behind her nonprofit Village to Village and its impact on first-gen students How she manages working full-time while running two passion projects What being a side hustler really looks like beyond social media glam The importance of mentorship, community, and believing in what’s possible for you This episode is for anyone trying to balance a 9-5, a side hustle, and a mission bigger than themselves. Listen now and get inspired to lead with heart, build with purpose, and bet on yourself — even when the path isn’t perfect. If you enjoyed this episode, please subscribe, rate, and review! Share this episode with someone who needs inspiration to take their own side hustle to the next level. Connect with Ja’Mya Giles: Village to Village Leadership Foundation Ja’Mya Made It LinkedIn Connect with us! ⁠Instagram

    40 min
  7. EP 3: The Diary of Tony Adams: “Faith, Family, Football - in that order”

    04/07/2025

    EP 3: The Diary of Tony Adams: “Faith, Family, Football - in that order”

    What does it really take to build a legacy — not just for yourself, but with your family by your side? On this episode of The Diary of a Side Hustler, we sit down with Tony Adams — former pro athlete, Super Bowl champion, and now, second-generation entrepreneur carving his path alongside the very people who shaped him. After a standout football career at NC State and a Super Bowl win with the New England Patriots, Tony’s NFL dreams were suddenly cut short by the pandemic. But instead of giving up, he returned to his roots — and his family — to start again. Inspired by his father’s entrepreneurial legacy, Tony became a key player in the family business, Adams Athletics, a trailblazing wrestling equipment company. Together, they’re proving that the stigma around working with family — “that it never works” — couldn’t be further from the truth. In addition to helping scale the family brand, Tony launched Athletic Money U and The OL Network, two platforms helping athletes turn passion into profit. His story is one of faith, humility, and leaning into the power of generational collaboration. In This Episode, You’ll Learn: What it’s really like working with family — the challenges, rewards, and lessons.How Tony transitioned from a professional athlete to a purpose-driven entrepreneur.The legacy behind Adams Athletics and how Tony is helping expand it.Why are community, mentorship, and family at the core of his business mindset?The importance of faith when your Plan A suddenly falls apart.How to turn setbacks into setups — especially when doing it together. Listen now and get inspired to build something lasting — with the people who matter most. If you enjoyed this episode, please subscribe, rate, and review! Share this episode with someone who needs inspiration to take their own side hustle to the next level. Connect with Tony Adams: InstagramThe OL NetworkAdams AthleticsAthletic Money U Connect with us! ⁠Instagram

    1h 7m
  8. EP 2: The Diary of Hannah Pleasant: Footwear and Frosting, and Make it Vegan

    03/31/2025

    EP 2: The Diary of Hannah Pleasant: Footwear and Frosting, and Make it Vegan

    What do you do when your dream career is no longer fulfilling? You reinvent yourself. On this episode of The Diary of a Side Hustler, we dive into the inspiring journey of Hannah Pleasant, founder of Vegan Bake Shop. From aspiring fashion designer to successful vegan baker, Hannah’s resilience and determination have guided her through multiple pivots and setbacks. Hannah’s story is one of creativity, adaptation, and hustle. After earning her degree from the Savannah College of Art and Design and working as a footwear designer, the pandemic hit and left her jobless. But instead of giving up, she found a new path inspired by her love for baking and her need for allergen-friendly desserts. What started as Bougie Vegan Bakery soon rebranded into Vegan Bake Shop, a business specializing in vegan and allergen-friendly treats with eco-friendly packaging. Despite numerous challenges — from relocating to Charlotte to balancing her baking business with a part-time job — Hannah continues to pursue her passion for entrepreneurship with unwavering dedication. Her story proves that setbacks can be powerful setups for something greater. In This Episode, You’ll Learn: How Hannah transitioned from fashion design to vegan baking.The personal experiences that inspired her to start Vegan Bake Shop.How rebranding played a key role in her business growth.The challenges of balancing entrepreneurship with a day job.Hannah’s approach to developing allergen-friendly recipes.The importance of creativity, resilience, and persistence in building a business. Listen now and be inspired to transform your own setbacks into setups for success! If you enjoyed this episode, please subscribe, rate, and review! Share this episode with someone who needs inspiration to take their own side hustle to the next level. Connect with Hannah Pleasant: Instagram Connect with us! ⁠Instagram

    1h 3m
  9. EP 1: The Diary of Kyle Horton: Ten Dollars and a Dream

    03/24/2025

    EP 1: The Diary of Kyle Horton: Ten Dollars and a Dream

    What does it take to turn passion into profit while managing a full-time career? On this episode of The Diary of a Side Hustler, we dive into the remarkable journey of Kyle Horton, a Charlotte, NC native whose dedication and resilience have driven him to achieve greatness both on and off the field. Kyle’s story is one of perseverance, growth, and pure hustle. From his impressive days as a 2X All Big-South Wide Receiver at Gardner-Webb University to navigating the challenges of entrepreneurship, Kyle’s journey is a testament to his unwavering commitment to success. After earning his degree in Business, Kyle launched Chosen 1 Training, a fitness and training enterprise he started while balancing his corporate role as a Risk Management Officer. Armed with lessons from mentors, hands-on experience, and his go-to resource — YouTube University — Kyle pushed through obstacles with determination and creativity. His journey shows how believing in yourself and staying adaptable can transform a side hustle into something extraordinary. In This Episode, You’ll Learn: How Kyle's athletic background shaped his mindset for business. The personal drive and determination behind launching Chosen 1 Training. How mentorship and online learning played key roles in his journey. The importance of adapting and learning through experience. Kyle’s strategy for managing a day job while pursuing his entrepreneurial dreams. Tune in and get inspired to turn your passion into profit, no matter how challenging the journey may be. If you enjoyed this episode, please subscribe, rate, and review! Share this episode with someone who needs inspiration to take their own side hustle to the next level. Connect with Kyle Horton: InstagramWebsite Connect with us! ⁠Instagram

    1h 35m

  10. Season 1 Trailer

    Pilot Episode with Kayla Brooks

    Welcome to the very first episode of "The Diary of a Side Hustler"! I'm your host, Kayla, a passionate storyteller here to bring you real, relatable stories of extraordinary individuals juggling side hustles and full-time careers. In this pilot episode, I'll introduce myself and share the exciting concept behind the show. Get ready to dive into inspiring journeys, learn from the challenges and successes of our amazing guests, and discover valuable insights to fuel your own side hustle dreams. Join me on this adventure and listen to "The Diary of a Side Hustler" on all streaming platforms and YouTube. Let's get into these diary pages! Connect with us! Instagram

    4 min

Trailer

About

Whether pursuing a passion project or passive income, over 40% of Americans have a side hustle. The Diary of a Side Hustler shares the personal stories of small business entrepreneurs who turned their passions into an opportunity for profit. Their stories share personal reflections on both the grind and the glory of balancing life, multiple jobs and everything in between.

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