Side Hustle Pro

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In this episode, I sat down with Jamila Wright, co-founder of Brooklyn Tea, to trace the full story of how she and her husband Ali turned tea dates into a business. Jamila walked me through leaving a career in education, emptying her retirement savings, and fighting a two year trademark battle before they ever opened their first location.

We got into the real financial decisions behind building out that first shop, including an SBA loan that arrived late, putting up her own home as collateral, and the lesson she learned about the difference between being an investor and being an owner operator. Jamila also shared how a relationship with a fellow Brooklyn business owner led to their current Lewis Avenue location.

From there we picked up with how Brooklyn Tea’s verticals came together, the financial setbacks along the way including a six figure loan and a partnership that fell apart, and the moment she and Ali finally started paying themselves.

Main Takeaways
Big opportunities often come from saying yes rather than a master plan, so be ready to rise to the moment when it arrives.
Waiting on outside funding like an SBA loan can force you to dip into personal savings, so plan for delays before signing a lease or starting construction.
Choosing between taking on debt or equity investors should depend on your long term goal, whether that is building a legacy brand or eventually selling it.
Paying yourself is a milestone that often comes after years of sacrifice, so figuring out that number is part of building a sustainable business.

Highlights Include
(00:32) How Jamila and Ali went from dating over tea to business partners
(08:12) The financial decisions behind opening the first Brooklyn Tea location
(16:16) Why Jamila had to put up her Atlanta home as collateral for their SBA loan
(19:38) Debt versus equity, and deciding what kind of business you want to build
(24:13) The real lesson foot traffic taught them about their first location
(29:45) How a relationship with Monique Greenwood led to their current Lewis Avenue location
(37:33) Saying yes to wholesale and e-commerce almost by accident
(47:39) Landing a licensing and franchising deal with an airport
(52:12) The Saks Fifth Avenue partnership that fell apart
(1:07:45) Paying themselves for the first time after two and a half years

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

Social Media
Website: brooklyntea.com
Brooklyn Tea Instagram: @brooklyntea
Jamila's Instagram: @jamilawright21
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⭐ APPLY TO SHIFT: https://sidehustlepro.co/shift

In this episode, I sat down with longtime friends and business partners Cynthia Bailey and Dana Hill-Robinson to talk about how a friendship that started in a New York hair salon in the 1990s turned into a skincare brand thirty years later. Cynthia shares her path from an eighteen year old model moving to New York to a reality television mainstay, while Dana walks us through her years at Vogue and Harper's Bazaar and building the beauty subscription box Cocotique.

We dig into how they finally partnered on Glowissima, why they chose to launch with only two hero products, and how they source ingredients like manuka honey and kiwi seed oil from New Zealand. Cynthia also opens up about the businesses she has closed in the past and what those experiences taught her about knowing when to walk away.

Cynthia and Dana get candid about profitability timelines, the current shift in consumer spending, and why a huge social following does not automatically translate into sales. They close out with practical advice for women who want to start a business but are worried about money and failure.

Main Takeaways
Launch lean: start with one or two hero products instead of a full line so you can prove the concept before scaling.
Know when to fold: it is a business skill, not a failure, to walk away from a venture once it stops making financial sense.
Vet every partnership: joint ventures work best when both sides have a track record and clearly defined roles from the start.
Followers are not buyers: a large social following does not guarantee sales, so keep testing your messaging and your audience.

Highlights Include
(00:19) How Cynthia and Dana met at a New York hair salon in the 1990s
(02:37) Cynthia's move from Alabama to New York at eighteen to model
(04:08) The Essence cover that became Cynthia's big break
(05:24) The move from modeling into reality television
(10:26) Lessons from closing the Bailey Wine Cellar and the Bailey Room
(14:44) Dana on pivoting Cocotique into a health and wellness hub
(17:56) The formulation story and meaning behind the name Glowissima
(19:14) Turning a thirty-year friendship into a business partnership
(27:01) Sourcing manuka honey and kiwi seed oil from New Zealand
(38:57) Digging deeper on marketing when the economy shifts

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
Cynthia Bailey: Instagram @CynthiaBailey
Dana Hill-Robinson: Instagram @DanaHillRobinson
Glowissima: Instagram, Facebook, and TikTok @Glowissima
Cocotique: Facebook @CocoTique, TikTok @CocoTiqueBeautyBox
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 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.