In this episode, I sat down with Karen Young, founder of OUI the People, a fine fragrance and body care brand born out of her own struggle with razor burn and ingrown hairs. Karen walks us through her path from fashion, where she interned at Dolce and Gabbana, to becoming an executive at Estee Lauder, to eventually building a beauty brand now sold in Sephora.

But Karen's story starts before OUI the People, with a lifestyle and home goods brand called Hammocks and High T that she built and ultimately had to close. We talk about the hard lessons on margins and capital that came out of that experience, the unexpected subway encounter that led to her job at Estee Lauder, and how she used her years inside a major beauty conglomerate to build her own brand from the ground up.

Karen also gets honest about the financial rollercoaster of raising venture capital, scaling a team, and chasing growth without profitability for years, and what finally shifted this year. We close things out with her thoughts on consumer psychology, pricing a premium product, and her advice for women weighing whether to leave a steady paycheck for their side hustle.

• Why closing a business is not failure, but tuition in a school of hard knocks that teaches you margins, capital, and scale.
• How to price a premium product by studying who your customer already trusts enough to spend on, not just what they say they need.
• Why visibility does not equal revenue, and how chasing growth without watching profitability can quietly sink a business.
• How building a trusted circle of fellow founders can matter more than any book when the entrepreneurial journey gets lonely.

• 00:20 - How a lifelong struggle with razor burn and ingrown hairs on melanated skin became the idea behind OUI the People
• 05:49 - Why Karen closed her first business, a lifestyle and home goods brand called Hammocks and High T
• 11:19 - Learning the difference between spotting a market gap and finding real money inside of it
• 16:00 - The subway encounter that led to Karen's job offer at Estee Lauder
• 25:37 - What Karen absorbed from watching a major beauty conglomerate acquire and scale brands from the inside
• 34:15 - The origins of OUI the People, which started as a direct to consumer razor brand called We Shave
• 41:14 - How Karen priced her first razor at seventy five dollars, then raised it to eighty five to ninety, by studying who was already buying La Mer
• 43:49 - Why Karen called manufacturers in the UK, Germany, and Japan before choosing a small German razor maker
• 50:39 - How the brand expanded from razors into body care, then into Sephora in 2019, then a full fragrance launch in 2023
• 57:57 - The honest truth about raising venture capital, scaling a team, and finally hitting profitability this year
• 1:12:19 - Lightning round: her go to founder resource, the mentor she admires, her non negotiable evening ritual, and her advice for side hustlers

• Shop OUI the People: ouithepeople.com

• ouithepeople.com
• OUI the People on Instagram: @ouithepeople https://www.instagram.com/ouithepeople/
• OUI The People TikTok: @ouithepeople https://www.tiktok.com/@ouithepeople

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

In this episode, I sat down with Busayo Olupona, founder and creative director of Busayo, the Brooklyn- and Lagos-based fashion brand known for its bold prints and textiles created with artisans in Nigeria. Busayo shares how she went from corporate finance law to bringing handmade pieces home in suitcases, selling them at scrappy pop-ups, and eventually landing in major retailers including Saks Fifth Avenue, Bloomingdale's, Shopbop, and Moda Operandi.

But this conversation goes much deeper than fashion. Busayo opens up about returning to a 9-to-5 after years of entrepreneurship, the shame and fear she had to unlearn, and the two serious cardiac events that forced her to confront the cost of constant striving. We talk about what it takes to build a business without losing yourself, why preparation matters before opportunity arrives, and how faith, meditation, and surrender changed the way she leads.

• Why learning a new industry while you still have a paycheck can protect both your savings and your confidence
• How to view returning to a job as reinvesting in your business, not failing at entrepreneurship
• Why Busayo had to separate her worth from her corporate title and other people's opinions
• How years of creating collections before buyers said yes prepared her for the Saks opportunity
• What two serious cardiac events taught her about sleep, stress, self-care, and sustainable ambition
• How wholesale relationships can drive recurring revenue, brand discovery, and direct-to-consumer sales
• Why Busayo believes faith, meditation, and surrender are practical tools for entrepreneurship

• 03:04 - Moving from Nigeria to the United States at age 11 and learning to reject parts of herself to fit in
• 16:44 - How annual trips to Nigeria planted the seed for the Busayo brand
• 19:37 - The first pop-up that pushed her to stop hiding her designs
• 24:05 - Leaving Cleary Gottlieb and unlearning the belief that she was not enough
• 29:16 - Attending her first trade show and returning with only two orders
• 31:36 - Meeting mentor Mercedes Gonzalez and learning how wholesale really works
• 32:36 - Going back to a legal job after burning through her savings
• 34:49 - Returning to the same office building and confronting the shame tied to her old title
• 36:19 - The first cardiac emergency that showed her she was pushing too hard
• 39:49 - Experiencing a second cardiac event and making sleep and self-care non-negotiable
• 47:59 - Why she now sees building a business as a spiritual endeavor
• 55:49 - How years of preparation helped her seize the opportunity that led to Saks
• 1:00:08 - Navigating strong years, lean years, and the impact of the Saks bankruptcy
• 1:06:17 - Why wholesale remains an important revenue and discovery channel
• 1:14:48 - Identifying your fear pockets before leaving a steady paycheck

• Shop Busayo
• The Fashion Designer Survival Guide by Mary Gehlhar
• RAISEfashion
• The Untethered Soul by Michael A. Singer
• Mindset by Carol S. Dweck

• Brand Instagram: @busayoworld: https://www.instagram.com/busayoworld/
• Personal Instagram: @busayojournal: https://www.instagram.com/busayojournal/

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

After a devastating flood forced Chrishon Lampley to close her Chicago art gallery and wine bar, she turned that loss into the foundation for Love Cork Screw, a nationally distributed wine brand that has sold more than two million bottles.

In this episode, Chrishon shares how she broke into the wine industry with no upfront capital, got her products into major retailers, and navigated the realities of building a consumer brand without millions in marketing dollars.

She also reveals how a wine created in honor of her late father became the official white wine of the Obama Presidential Center, and what it took to rebuild after nearly losing the business again.

• A devastating setback, like losing a business to a flood, can become the foundation for something bigger if you keep moving forward.
• Building relationships and repeatedly asking for the sale, even after rejection, can open doors that money alone cannot.
• Chasing notoriety across too many markets at once can cost more than it earns; focusing on one market at a time builds real traction.
• Consistent, face to camera content can rebuild a business faster than relying on a marketing budget alone.

• [00:32] The flood that closed Three P's Art Lounge and led to Love Corkscrew
• [01:26] Becoming one of the first African American women with an on and off premise liquor license in downtown Chicago
• [05:58] Starting the Love Corkscrew blog as a way to heal after losing the gallery
• [11:14] Explaining what a negociant is and pioneering the term in the wine industry
• [17:30] Building Love Corkscrew from nothing through commission and consignment deals
• [24:41] The advice from Barefoot Wine's founders that changed her strategy
• [32:07] Losing her father and creating the Lampley wine line in his honor
• [35:00] Landing the deal to become the official white wine of the Obama Presidential Center
• [39:30] Running the Clink and Sip Festival and the Sipping Empower Foundation
• [44:29] Committing to daily social media consistency to rebuild the business in 2026

• lovecorkscrew.com
• thelampley.com

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

• Instagram: @lovecorkscrew

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'm sharing the seven beliefs I had to unlearn before I could finally leave my corporate job and build Side Hustle Pro full time. I spent decades in corporate America, working at places like HBO, MTV, Google, and NPR, and even though I knew I wanted to leave, I wasn't mentally ready until I confronted the internal beliefs that kept me tied to that life.

• 00:00 - My corporate background and why I'm scratching the record on old habits
• 03:01 - The seven things I had to unlearn to build Side Hustle Pro full time
• 06:48 - Unlearning the need to have my entire future figured out before leaving
• 11:25 - Why other people's opinions could not be my decision making system
• 17:31 - Unlearning that a job or promotion was my only path to more money
• 21:59 - Pay inequity in corporate and why the ceiling is lower than it seems
• 22:49 - Unlearning that I was limited to doing only what I had already done
• 27:33 - Confusing busyness with meaningful progress, and the one hour a day model
• 33:36 - The biggest unlearn: staying employed was not actually the safest option
• 42:21 - Reflection questions to figure out which belief you're still carrying

Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t

Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323

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 episode, I sat down with Dawn Fitch, founder of Pooka Pure and Simple, to talk about the winding road that took her from designing album covers in the music industry to building a natural beauty brand rooted in her own health journey. Dawn opens up about the years it took to get an MS diagnosis, and how healing herself led her to start formulating clean, simple products long before she ever thought of herself as a business owner.

We get into the real, unglamorous parts of entrepreneurship: street teaming outside churches before social media existed, a cease-and-desist letter that almost derailed her Whole Foods deal, and the hard lessons of scaling into big box retail. Dawn also shares how she walked away from a failing retail lease with nowhere to go, only to land in the space that's been home to her production for over a decade.

Finally, Dawn walks me through the newest chapter of her story: a 250,000 dollar grant from Audible's DEI program that brought Pooka into a beautiful new Newark location, and how an activity she almost treated as an afterthought, the Bloom Bar, became the biggest draw of the whole business.

• Protect your business structure early. Trademark your name, keep separate books, and build SOPs before you're forced to by a cease-and-desist letter or a big retail opportunity.
• Don't chase big box retail until your core revenue stream is stable enough to absorb the rules, returns, and thin margins that come with it.
• When a business decision doesn't feel right, it is okay to walk away even without a backup plan. Trust and timing can lead you somewhere better.
• Build a real activation or experience around your product. Community and connection, not just the product itself, is what keeps customers coming back.

• (00:41) Dawn's start as a graphic designer in the music industry, designing album covers
• (01:36) The moment paralysis first hit while she was walking to work
• (03:04) The five-year journey to her eventual MS diagnosis
• (05:15) How the name Pooka came from her mother calling her kids her pooka leaders
• (07:19) Why email marketing became the backbone of the business from day one
• (11:01) The cease-and-desist letter over the brand name right before entering Whole Foods
• (13:49) How putting her pride to the side led to her first 10 Whole Foods stores
• (18:29) Her advice on knowing when a business is truly ready for big box retail
• (26:51) Why Pooka exited all 62 of its Whole Foods stores last year
• (29:04) How the Best Life Tribe Facebook group and a sea moss request from a member helped save the business during the pandemic
• (32:07) Landing the 250,000 dollar Audible DEI grant for the new Newark space
• (35:14) How the Bloom Bar, almost an afterthought, became the biggest draw of the business

Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t

Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323

Website: pookapureandsimple.com

Instagram: @Pookalita

TikTok: @Pookalita1

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 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.

• 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

Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t

Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323

• Instagram, TikTok, and X: @Roxycouse

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