The Diary of a Side Hustler

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.

The Diary of a Side Hustler is a business podcast hosted by Kayla Brooks, with 10 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Kayla Brooks hosts The Diary of a Side Hustler, a business show with 10 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

• 

  Episode #8

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

  Jun 2, 20251 hourS1

  <p>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.</p><p>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 ha...

  ListenShow Notes
• 

  Episode #7

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

  May 26, 202548 minS1

  <p>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.</p><p>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 t...

  ListenShow Notes
• 

  The Diary of a Side Hustler

  Journal Entry: Life is Messy

  May 12, 202513 minS1

  <p>Today’s Journal Entry Prompt: What is a messy area in your home, business, workplace or life?</p><p>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.</p><p>Tune in to hear her share unfiltered thoughts on managing the complexities of trying to thrive at home, work, business, and life. </p><p><br></p>

  ListenShow Notes
• 

  Episode #6

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

  May 5, 202550 minS1

  <p>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! </p><p>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 i...

  ListenShow Notes
• 

  Episode #5

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

  Apr 28, 202555 minS1

  <p>What happens when life forces you to take a leap of faith, and that leap transforms into a thriving business?</p><p>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 pa...

  ListenShow Notes

Recent guests on The Diary of a Side Hustler. Study who booked and why before you pitch.

Based on semantic analysis of episode topics and host coverage, this show is a strong guest fit for executives in:

Industry fit is computed by PitchCentric using vector embeddings of the show's episode catalog.