Side Hustle Pro

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

In this episode, I sat down with Roxy Couse, the creator behind Millennial Manager, to talk about how she built a thriving personal brand while climbing the corporate ladder. Roxy spent almost 15 years in corporate, working her way up to senior director, before stepping away to run her content and consulting business full time.

We got into the real logistics of that transition, from going part time first, to navigating conflict of interest concerns at work, to eventually bringing on a management team once the opportunities became too much to handle alone. Roxy also opened up about paying off student loan debt with her side hustle income and the exact moment she realized her content could become a real business.

Roxy is now building SlowFi, a platform designed to help other corporate professionals build profitable personal brands with structure, community, and coaching.

Main Takeaways:

Consider going part time before fully leaving your job so you can test whether your side income is consistent before walking away completely.
Protect your main income while building a passion project by staying discreet at work and avoiding brand partnerships that could create a conflict of interest.
Bring on a management team or support staff once inbound opportunities outgrow what you can manage on your own, especially around contracts and negotiations.
Personal brand building does not have to be high effort. Make content creation fit into the pockets of time you already have instead of forcing a rigid content calendar.

Highlights Include
1:01 - Roxy's 15 year corporate career and her shift into content creation
3:50 - What held Roxy back from starting to create content
6:36 - The origin story behind her Millennial Manager persona
8:09 - How Roxy navigated conflict of interest concerns while working full time
14:20 - Why she went part time before leaving corporate completely
19:51 - The moment she realized she needed a management team
25:26 - How her one on one consulting turned into building SlowFi
33:24 - Her timeline for launching SlowFi and the realities of bootstrapping as a Black founder
38:22 - Balancing motherhood with running her business
47:00 - Lightning round: resources, admiration, non-negotiables, and her advice for aspiring side hustlers

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

Social Media
Instagram, TikTok, and X: @Roxycouse
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 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
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 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.