Side Hustle Pro

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⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift

In this episode, I sat down with Jotaka Eaddy, founder of Full Circle Strategies and Win With Black Women, for a conversation about power, purpose and resilience. We talked about her childhood in Johnsonville, South Carolina, a town of under 1,400 people that taught her the value of community long before she ever set foot in Washington, DC or Silicon Valley.

Jotaka walked me through her path from student activist against the death penalty to senior advisor at the NAACP to becoming the first Black employee at a fintech startup in Silicon Valley. She opened up about the layoff that nearly broke her and the Oprah Winfrey clip that helped her reframe it as redirection rather than failure.
We also talked about how Win With Black Women was born from a single late night email in 2020 that turned into a Zoom call with 44,000 women, and how that same community continues to organize today. Jotaka got vulnerable about losing her mother during the 2024 election season and what that grief has taught her about faith, resilience and asking for help.

Main Takeaways
Your community can be your first investors. The people of Jotaka's hometown pooled money so she could attend a conference that changed the course of her life.
A layoff is not always failure. It can be redirection toward something bigger than you could have planned for yourself.
Movements are built in the quiet, consistent work that happens long before anyone is watching or celebrating.
Black women hold real power at the ballot box and in daily acts of organizing, even while in survival mode.

Highlights Include
02:01 - Growing up in Johnsonville, South Carolina
05:04 - The conference that changed her life
11:46 - Learning to lead by carrying the bag
15:17 - Making the leap into Silicon Valley
19:08 - Getting laid off and finding strength in an Oprah Winfrey clip
29:02 - The spark behind Win With Black Women
35:40 - The night 44,000 women joined the call
44:53 - How to show up when you are in survival mode
48:05 - Opening up about losing her mother

Watch & Listen
Watch this episode on YouTube and listen on all podcast platforms:

Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
YouTube: https://www.youtube.com/sidehustlepro

Announcements
Applications are now open for Shift, my 12-week coaching program designed to help experienced professionals package their expertise into a profitable offer, identify their first clients, and confidently launch their next chapter.
Learn more and apply at: https://sidehustlepro.co/shift

Social Media
Jotaka Eaddy: Instagram: @JotakaEaddy
Win With Black Women: Instagram: @WinWithBlackWomen
Hosted on Acast. See acast.com/privacy for more information.

If this resonated with you, here are additional resources:

⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift

When I launched Side Hustle Pro, I thought success would be measured by downloads, rankings, sponsorships, and audience growth. And while reaching 10 million downloads is a milestone I'm incredibly grateful for, I've learned that the true value of podcasting has very little to do with the number itself.

In this episode, I share the biggest lessons I've learned after more than 500 episodes and 10 million downloads. From building meaningful relationships and creating opportunities I never could have predicted to developing new business offers, growing a loyal community, and gaining clarity on my next chapter, podcasting became much more than a content platform. It became a vehicle for transformation.

Whether you're a podcaster, entrepreneur, creator, or professional looking to build your personal brand, this episode will challenge you to think differently about what you're creating and how it can become the bridge to where you want to go next.

Main Takeaways
Downloads are not the destination. Trust, relationships, and opportunity are the true assets.
A podcast can become a powerful networking tool that opens doors you never expected.
Specificity and niching down accelerate discoverability, growth, and community building.
Podcasting can help you validate ideas, package your expertise, and build your next business offer

Highlights Include
00:00 – The lesson behind 10 million podcast downloads
01:16 – Why podcasting became my most powerful networking tool
03:28 – The new podcasting playbook for creators and entrepreneurs
04:17 – Building trust through the intimacy of audio
05:39 – My thoughts on video podcasting and discoverability
10:34 – Why niche podcasts grow faster than general ones
14:50 – Trust as the most valuable asset you build
16:27 – How Side Hustle Pro led to national media opportunities
18:30 – The unexpected doors podcasting opened for my career
20:04 – Why most podcasts struggle to grow
21:36 – How podcasting became the bridge to my next chapter
23:52 – Why I created the Shift Program

Links Mentioned in This Episode
Shift Program: https://sidehustlepro.co/shift

Watch & Listen
Watch this episode on YouTube and listen on all podcast platforms:
Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
YouTube: https://www.youtube.com/sidehustlepro

Announcements
Applications are now open for Shift, my 12-week coaching program designed to help experienced professionals package their expertise into a profitable offer, identify their first clients, and confidently launch their next chapter.
Learn more and apply at: https://sidehustlepro.co/shift

Social Media
Instagram: @sidehustlepro
Hosted on Acast. See acast.com/privacy for more information.

If this resonated with you, here are additional resources:

⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift

In this solo episode, I am getting real with you about the one skill that changed everything for me and that I believe every woman needs to develop right now: learning how to make money directly for yourself. I am sharing why the leap from employee to entrepreneur is so hard, how our entire lives have programmed us to earn money for someone else, and what it truly takes to start creating money on your own terms.

I take you back to my days at NPR, where I was climbing the ladder, playing the game, and quietly building Side Hustle Pro on the side. I share how a hater coworker who reported me to my boss became the catalyst for my exit plan, how I landed my first $4,000 podcast sponsorship from a cold customer service email, and how learning just two revenue streams gave me the confidence to leave my job for good.

This episode is also a reminder that you do not have to have everything figured out before you start. Your first $20 or $25 outside of your paycheck changes something in you that no amount of planning can replicate. If you are sitting at a crossroads wondering what your next move is, this episode is your sign to start choosing yourself.

Main Takeaways
The difficulty of leaving a job is not fear or lack of risk tolerance; it is decades of programming to earn money for someone else, and that programming can be unlearned.
Earning money depends on someone else choosing you, while creating money is about identifying a problem, building a solution, and offering it to the world.
You do not need two revenue streams mastered before you act; your first dollar outside a paycheck unlocks a shift in confidence and mindset that no amount of planning can give you.
Showing up imperfectly is part of the process; authenticity attracts the right people and gives your audience permission to let their guard down too.

Highlights Include
00:01 - Why I chose to record this episode on the go with ease over perfection
02:27 - How jobs program us to earn money for someone else and why that makes the leap so hard
03:06 - The story of bringing my now-husband Muoyo to my NPR holiday party and what it revealed about being stuck in the corporate mindset
07:31 - Why smart, experienced, degreed women still feel stuck and what they are actually missing
09:49 - The difference between earning money (someone choosing you) and creating money (creating value)
12:15 - Why showing up imperfectly is how you attract your people, especially as Black women in professional spaces
14:37 - Why relying on someone else to choose you is bad for your mental health, and what to do instead
18:47 - My personal backstory: launching Side Hustle Pro while at NPR and investing $1,197 in a sponsorship intensive
21:06 - How a cold email to a customer service inbox landed me my first $4,000 podcast sponsorship contract
25:52 - The coworker who reported me to HR and how that moment became the push I needed to start my exit plan
00:00 (Part 2) - Why your first $25 changes everything internally and how making money directly for yourself is the skill to build right now

Links Mentioned in This Episode
Shift Coaching Program: sidehustlepro.co/shift

Watch & Listen
Listen to Side Hustle Pro on Apple Podcasts: podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
Listen on Spotify: open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t

Announcements
SHIFT, my transformational coaching program for ambitious women who want to turn their side hustle into their exit plan from their 9-to-5, is now open for applications. Apply now at sidehustlepro.co/shift before spots fill.

Social Media
Side Hustle Pro Instagram: @SideHustlePro

Hosted on Acast. See acast.com/privacy for more information.

If this resonated with you, here are additional resources:

⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift

In this solo episode, I'm pulling back the curtain on my entrepreneurial journey and sharing the six most important lessons I've learned since leaving my corporate job in 2017. Most people assume that quitting was my biggest risk, but the truth is, the scariest steps happened long before I ever turned in my notice.

I take you all the way back to 2015, when I graduated from business school without a job after not receiving the full-time offer from my Google internship. From studying abroad in Barcelona to avoid reality, to moving back to DC and starting a blog with no plan, this episode is about what really happens in the messy middle before success shows up. I share how rejection led me to NPR, how my experience there became the foundation for Side Hustle Pro, and how I earned my first $4,000 sponsorship contract from a cold email to a customer service inbox.

This episode is for anyone who is waiting for a sign, a plan, or the perfect moment. Spoiler: that moment is not coming. What is coming is everything you need to build, but only if you start. I break down exactly how I got here and what I want you to take away from this milestone journey.

Main Takeaways
Rejection is redirection: Not getting the Google offer was the push that led Nicaila to build Side Hustle Pro.
You don't need the whole plan: Taking one next step, even without knowing where it leads, is how clarity is built.
Clarity comes from action: The idea for Side Hustle Pro did not come before the action; the action revealed the idea.
Bet on proof, not hope: Nicaila didn't quit her job out of fearlessness, she quit because she had consistent data showing her business could grow.

Highlights Include
[00:02] I share the real biggest risk I took, and it wasn't quitting my job
[00:24] The Google internship story: expecting the full-time offer and not getting it
[02:45] Graduating from business school with no job, no plan, and moving back to DC
[04:40] Lesson 1: Rejection is redirection, and what that looked like in real life
[07:16] Lesson 2: You don't need the whole plan, just the next step
[00:02 segment 2] Lesson 3: Clarity comes from action, not waiting for an aha moment
[03:11] How Side Hustle Pro's concept was born out of a boring blog pivot
[07:26] Lesson 5: Bet on proof, how I earned my first $4,000 sponsorship
[11:37] The real reason I quit: not fearlessness, but evidence
[12:19] Lesson 6: The life you want is built before you leave, not after

Links Mentioned in This Episode
APPLY TO SHIFT: https://sidehustlepro.co/shift

Watch & Listen
Listen to Side Hustle Pro on Spotify: open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
Listen on Apple Podcasts: podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323

Social Media
Instagram: @SideHustlePro

Hosted on Acast. See acast.com/privacy for more information.

In this episode, I sat down with Camille Joy, founder of the Moments of Joy Podcast and author of Moments of Joy: 90 Days of Encouragement, published by Penguin Random House. Camille is a trafficking survivor who escaped an abusive situation at 21, became a high school dropout turned executive chef, and fought her way into a six-figure salary by going directly to the CEO. When her youngest son Mason was diagnosed with autism, everything shifted again, and a raw, tear-filled video she recorded in her car after a difficult doctor visit went viral with over six million views in 2022.

Today Camille runs two businesses: Moments of Joy, her for-profit media brand built on brand deals, speaking, and her book, and Awesomely Different, her nonprofit that provides swimming lesson grants for children with autism. She also shares how she and her filmmaker husband manage it all without a village, and what it really took to land Holly Robinson Peete as a podcast guest after five attempts over several years.

Main Takeaways
Your test is your testimony: Camille's openness about trafficking, autism, and grief is what built her audience and her business.
Tackle the shame first: Before you can turn your story into impact, you have to get comfortable sharing what you have been through.
Serve before you ask: Camille landed Holly Robinson Peete as a guest by consistently showing up in her community, buying her book, attending her events, and reaching out five times before getting a yes.
Caregiving and entrepreneurship can coexist: Camille and her husband run two businesses while raising Mason by communicating constantly, sharing schedules, and giving each other permission to pursue their goals.

Highlights Include
00:46 - Camille shares what life looked like before the Moments of Joy Podcast existed
01:45 - Mason's birth story and three heart surgeries in 18 months
02:42 - Receiving Mason's autism diagnosis and how it changed everything
04:40 - Camille reveals she is a trafficking survivor and how she escaped at 21
06:06 - How a stranger saying her name out loud was the sign she needed to go to culinary school
09:14 - Fighting for the executive chef title at ConAir Corporation by CC'ing the CEO
11:13 - Going to the CEO directly to demand her six-figure salary and getting it on the spot
23:22 - The viral reel that changed everything: 6 to 7 million views after a tearful moment in the car
27:06 - Launching Awesomely Different, her nonprofit that teaches children with autism to swim
31:52 - Signing with Penguin Random House and the reality of first-round edits
38:45 - How Camille and her husband manage two businesses and Mason's care without a traditional village
46:01 - Why tackling shame is the first step to turning your test into a testimony
52:03 - The strategy behind landing Holly Robinson Peete and why she reached out five times
56:17 - Lightning round: resources, role models, daily non-negotiables, and parting advice

Links Mentioned in This Episode
Podcorn (early podcast sponsorship platform): https://podcorn.com
Moments of Joy Podcast: https://www.mojpodcast.com/

Watch & Listen
Side Hustle Pro Podcast on Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
Side Hustle Pro Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323

Social Media
Instagram: @momentsofjoypodcast
TikTok: @momentsofjoypodcast
Hosted on Acast. See acast.com/privacy for more information.