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The Diary of a Side Hustler

Hosted by Kayla Brooks · business · EN-US · 10 episodes

Audience: 2

About this Podcast:

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.

Pitch Analysis

Required Pod Score for this show. PitchCentric checks your profile against host openness, topical fit, and audience signals before you generate a pitch.

Contact path

Verified email

Booking probability

18%

Guest openness

Selective

Verified email on file
80/100
Required Score

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Questions about The Diary of a Side Hustler

What is The Diary of a Side Hustler 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.

Who hosts The Diary of a Side Hustler?

The Diary of a Side Hustler is hosted by Kayla Brooks. The show has published 10 episodes to date.

What has The Diary of a Side Hustler covered recently?

Recent episodes include "EP 8: The Diary of Montez Hymon: The Price Paid for Privacy" (2 June 2025, 60 minutes), "EP 7: The Diary of Reggie Pharr: Knowing When to Flip" (27 May 2025, 48 minutes), and "Journal Entry: Life is Messy" (12 May 2025, 13 minutes).

How often does The Diary of a Side Hustler publish?

The Diary of a Side Hustler publishes roughly weekly, with episodes averaging 50 minutes across 10 episodes.

How hard is it to get booked on The Diary of a Side Hustler?

Booking probability for The Diary of a Side Hustler is 18%, and the host is rated Selective on guests. The Diary of a Side Hustler requires a Pod Score of 80 or higher. The Diary of a Side Hustler's contact route on record: verified email.

Who should pitch The Diary of a Side Hustler?

The strongest fits for The Diary of a Side Hustler are Business & Management Consulting and Photography, Polling & Other Services. The Diary of a Side Hustler has a business audience.

About the host

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

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Recent episodes

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...

  • Episode #7

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

    May 27, 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...

  • 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...

  • 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...

  • 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...

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  • Episode #4

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

    Apr 14, 202540 minS1

    <p>What happens when creativity, community, and hustle collide?</p><p>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...

  • Episode #3

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

    Apr 7, 20251h 7mS1

    <p>What does it really take to build a legacy — not just for yourself, but with your family by your side?</p><p>On this episode of The Diary of a Side Hustler, we sit down with Tony Adams — former pro athlete, Super...

  • Episode #2

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

    Mar 31, 20251h 3mS1

    <p>What do you do when your dream career is no longer fulfilling? You reinvent yourself.</p><p>On this episode of The Diary of a Side Hustler, we dive into the inspiring journey of Hannah Pleasant, founder of Vegan Bake...

  • Episode #1

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

    Mar 24, 20251h 35mS1

    <p>What does it take to turn passion into profit while managing a full-time career?</p><p>On this episode of The Diary of a Side Hustler, we dive into the remarkable journey of Kyle Horton, a Charlotte, NC native whose...

  • The Diary of a Side Hustler

    Pilot Episode with Kayla Brooks

    Mar 18, 20254 minS1

    <p>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...

Guest Appearances

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