Rich Lessons

Sevetri Wilson and Sheena Allen
  • 5.0 (33)
  • Entrepreneurship
  • Updated Weekly

The Rich Lessons Podcast, hosted by Sevetri and Sheena, cuts through the noise with rich insights and real conversations about business, life, and everything in between—offering hard truths, valuable lessons, and stories still being written.

  1. 4d ago

    She Built a $800 Million Agency From Her Closet

    Carrita Cloud is the founder and CEO of Creativity Justified, the agency behind work for the NFL, Microsoft, Delta, Ochsner Health, the Saints and the Pelicans. Inc. named her to the 2025 Female Founders 500. Her team has managed over $800 million in advertising dollars.She started it in a closet. Seven months pregnant, just fired, insurance gone, cold calling and cold emailing people who mostly said no.We got into all of it — the systems she built when it was still just her, how she actually got in the room with the NFL, and what COVID did to her retainers when it was still a small business agency.But the part that stopped us cold was the pricing story. She bid $25,000 on a contract. Another Black woman on the other side called her and said if I submit this, they'll think you're a joke. The lowest competing bid was $125,000.If you've ever wondered whether you're charging enough, this one is for you 🎧━━━━━━━━━━━━━━━WHAT WE GET INTO▸ Getting fired at 7 months pregnant and starting over the next morning▸ The department emails she made up when it was still only her▸ Why you need degrees of separation between you and your clients▸ Building 100+ email templates before hiring anybody▸ "We invite people into our chaos, then get mad when they fail in chaos"▸ Why most people's VA experience goes wrong▸ How she actually got to $800 million in managed ad spend▸ Pitching the NFL on a webinar — and it going all the way to Roger Goodell▸ What COVID did to her retainers, and the pivot that saved the agency▸ The $25K bid vs the $125K bid▸ Why she took pricing off her website▸ Advice for anyone leaving corporate right now▸ "I love my family too much to ever hire them"▸ Niceness vs kindness, and why her team is not a family▸ The two hires she'd make again every single time▸ How to actually get in front of Fortune 500 clients▸ Her rich lesson: the money conversation nobody has with new founders━━━━━━━━━━━━━━━FOLLOW CARRITA CLOUDCreativity Justified━━━━━━━━━━━━━━━RICH LESSONS PODCASTHosted by Sevetri Wilson Taylor and Sheena Allen🎧 LISTEN & SUBSCRIBEApple Podcasts: https://podcasts.apple.com/us/podcast...Spotify: https://open.spotify.com/show/40jGSUv...▶️ WATCH & SUBSCRIBE ON YOUTUBE   / @richlessonspodcast  📲 FOLLOW RICH LESSONSInstagram:   / richlessonspodcast  TikTok:   / richlessonspodcast  ━━━━━━━━━━━━━━━#RichLessons #BlackWomenInBusiness #AgencyLife #Pricing #KnowYourWorth #Entrepreneurship #MarketingAgency #BlackEntrepreneurs #WomenFounders #SmallBusiness #BusinessSystems #NFL #BusinessPodcast #FounderStory #Fortune500

  2. Sep 8

    How to Hire When You Have No Money | Rich Lessons

    Everybody wants to tell you about scaling and Series A. Nobody sits down and says, "Here's what it actually costs to get one person helping you when you have almost nothing." So that's what this one is. Between the two of us, we've done it every way there is — freelancers, contractors, offshore, W-2, fractional, all of it. Some of it worked. Some of it cost us money we didn't have. We're giving you real numbers. Real mistakes. The rules we follow now because we learned them the hard way. Sheena tells the story about the freelancer who had one of HER OWN apps sitting in their portfolio. That one still gets us. We also got into whether your first hire can just be an AI agent in 2026, and we don't fully agree on it. Let us know where you land. If you're building with a small budget right now, this one's for you.  WHAT WE GET INTO▸ Where we actually find freelancers, and which sites we prefer▸ Offshoring vs outsourcing — people use these wrong all the time▸ The 3 AM problem nobody warns you about with offshore work▸ Why we don't fully trust 5-star ratings anymore▸ How to vet a portfolio (including reaching out to their past clients cold)▸ The freelancer who had Sheena's own app in their portfolio▸ Milestones, escrow, and the upfront payment rule that saves people thousands▸ Real numbers: what engineers and designers cost right now, here and offshore▸ Why 2021 was the wildest hiring year either of us has seen▸ When fractional work makes sense — and when it doesn't▸ How much runway you need before you make a real hire▸ What a W-2 employee actually costs (it's not the salary)▸ Can your first hire be an AI agent? We go back and forth on this one▸ Why the moat isn't tech anymore▸ Our richest lessons: fire fast, and the order you hire in matters ━━━━━━━━━━━━━━━ RICH LESSONS PODCASTHosted by Sevetri Wilson Taylor and Sheena Allen LISTEN & SUBSCRIBE Apple Podcasts: https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124 Spotify: https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8kl WATCH & SUBSCRIBE ON YOUTUBE https://www.youtube.com/@richlessonspodcast FOLLOW RICH LESSONS Instagram: https://www.instagram.com/richlessonspodcast TikTok: https://www.tiktok.com/@richlessonspodcast ━━━━━━━━━━━━━━━ #RichLessons #HiringOnABudget #Freelancers #Upwork #Offshoring #StartupAdvice #Entrepreneurship #SmallBusiness #Bootstrapping #FounderMindset #WomenInBusiness #BusinessPodcast #FractionalWork

  3. Sep 3

    Why Strong Women Don't Take Breaks (And Why That's Killing Us)

    Dr. Alicia Reed is a pharmacist. She spent 20 years telling other people how to take care of their health. Then her husband died of a massive heart attack at 43, four days before Christmas — and she became a widow overnight at 40, with a four-year-old.Then the pandemic hit. She was on the frontline as a healthcare provider while her own blood pressure was dangerously out of control.It took her son asking "Mommy, are you going to die too?" for her to actually stop.We talked about all of it. Grief, burnout, food, the health stuff nobody's checking on, and the generational curse that says strong women don't get to rest. She also learned how to swim at 46 — in six days — and that story alone is worth the watch.If you're the person everybody depends on, this one is for you.WHAT WE GET INTO▸ Who NOLA Bougie was, and how she became Dr. Reed▸ Losing her husband four days before Christmas▸ Grieving in public while raising a grieving four-year-old▸ Why rest got turned into something you have to earn▸ How burnout actually shows up — inflammation, autoimmune flares, blood pressure▸ "Who takes care of the person everyone else depends on?"▸ Why she says it's women, not men, skipping the doctor▸ Two stories about what happens when you wait too long to get checked▸ Food as medicine: reading labels, the ginger ale that shocked us, and what to actually look for▸ Eating well when you live in a food desert▸ The health insurance benefits you're paying for and never using▸ The health trend that worries her most right now▸ Learning to swim at 46 after being thrown in as a child▸ Rapid fire: time vs energy, boundaries vs discipline, and which is harder — success or healingFOLLOW DR. ALICIA REED - https://www.instagram.com/DrAlishaReed/Your Self-Care Prescription LLCFly Widow Podcasthttps://open.spotify.com/show/536vGTR2zWrh17VcUtX5JIRICH LESSONS PODCASTHosted by Sevetri Wilson Taylor and Sheena Allen🎧 LISTEN & SUBSCRIBEApple Podcasts: https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124Spotify: https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8kl▶️ WATCH & SUBSCRIBE ON YOUTUBEhttps://www.youtube.com/@RichLessonsPodcast📲 FOLLOW RICH LESSONSInstagram: https://www.instagram.com/richlessonspodcastTikTok: https://www.tiktok.com/@richlessonspodcast━━━━━━━━━━━━━━━#RichLessons #BlackWomensHealth #HeartHealth #SelfCare #Burnout #BlackWomenPodcast #Grief #Widowhood #FoodIsMedicine #WomensHealth #Pharmacist #HighBloodPressure #BlackWomenInBusiness #Wellness #PreventativeHealth

  4. Aug 27

    RIP Dolly Parton, Gary Indiana's Power Crisis & the Surrogate Suing for Custody | Rich Takes

    Dolly Parton is gone, Gary, Indiana has been without power for weeks, and New York City is trying to fight rising grocery prices with city-run supermarkets. Meanwhile, a controversial surrogacy case has turned into a legal and cultural battle over parental rights, abortion, and who gets to make medical decisions for a child. Sheena Allen and Sevetri Wilson Taylor break down the biggest stories in business, culture, politics, and society—from Dolly Parton’s complicated legacy and the power grid crisis to the fight over NYC’s grocery stores and the viral surrogate custody case making headlines. In this episode:• Dolly Parton’s death, philanthropy, and her legendary responses to Whitney Houston and Beyoncé covering her music• Why Gary, Indiana went weeks without power—and why so few people were talking about it• Memphis’ massive power outage and questions about America’s aging power grid• New York City’s plan for city-run grocery stores with lower prices• Why bodega owners are fighting the plan• The bizarre and controversial surrogacy case involving a seriously ill baby• The growing debate over surrogacy, parental rights, and reproductive politics ---- Subscribe to Rich Takes on Apple Podcasts and Spotify, and leave us a review if you enjoyed the episode. Apple Podcasts: https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124 Spotify: https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8kl?si=9666ca84559c4e16 YouTube: https://www.youtube.com/@richlessonspodcast Instagram: https://www.instagram.com/richlessonspodcast/ TikTok: https://www.tiktok.com/@richlessonspodcast

  5. Aug 25

    Work-Life Balance Isn’t Real: The Truth About Money, Hustle & Entrepreneurship

    Is work-life balance a real concept, or is it something people say when they aren’t serious about their goals? In this episode of Rich Lessons, hosts Sheena Allen and Sevetri Wilson Taylor pull back the curtain on the reality of modern entrepreneurship, wealth, and scaling a business. Drawing from three stacks of unfiltered questions—Professional, Personal, and Rapid Fire—they break down the sacrifices, mindset shifts, and hard choices required to succeed at the highest level. Key Topics Included: The Myth of Work-Life Balance: Why high-stakes goals demand a different level of output.Founder Non-Negotiables: Maintaining board control, avoiding hyper-preferred rights, and lessons from building in fintech.Hustle Culture vs. Real Hustle: The line between being a true operator and falling for social media “gurus”.Managing & Hiring: Why treating your team like “family” is a trap, plus the truth about hiring friends.Wealth vs. Freedom: Why money doesn’t always equal peace and how to avoid being rich and miserable. If you’re building a business, advancing your career, or looking for candid advice on wealth and modern lifestyle, tune in now. Enjoying the show? Leave us a 5-star rating and review on Spotify and Apple Podcasts!

  6. Aug 20

    Google Bought 34 Years of Data for $10M?! + Equifax's $100M Credit Score Mess | Rich Takes

    Google reportedly acquired 34 years of enterprise data from Spirit Airlines, including more than 100 million emails, 500 million Microsoft messages, workflows, and code, for just $10 million. Is Big Tech getting a bargain on the data it needs to train AI? This week on Rich Takes, Sheena Allen and Sevetri Wilson Taylor break down the biggest stories across tech, business, finance, and culture—including the growing race for valuable data, AI's impact on privacy and consumer pricing, algorithmic dynamic pricing, and Amazon's reported efforts to acquire rare books for AI training. Plus, Equifax is paying $100 million to settle a class-action lawsuit after millions of consumers' credit information was reportedly misreported because of a coding glitch. The conversation goes deeper into why the credit scoring system may be outdated, and what happens when the financial system gets it wrong. And yes, they also get into the wild Penn State fraternity cocaine-trafficking and hazing case that somehow flew under the radar. In this episode: Google and the race to acquire valuable data for AIThe $10 million enterprise-data dealAI, privacy, and the rise of dynamic pricingWhy your search and purchase history could affect what you payEquifax's $100 million credit score settlementAre credit scores outdated?The Penn State fraternity cocaine-trafficking caseThe stories flying under the radar this week ---- Rich Takes is the weekly mini-episode, hot-take conversation from Rich Lessons, where Sheena and Sevetri unpack the week's biggest headlines across business, tech, finance, entertainment, lifestyle, and culture. Listen to Rich Takes every week and subscribe to Rich Lessons for the full conversations. Apple Podcasts: ⁠https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124⁠ Spotify: ⁠https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8kl?si=9666ca84559c4e16⁠ YouTube: ⁠https://www.youtube.com/@richlessonspodcast⁠

  7. Aug 18

    Safety Advice Every Woman Needs to Hear (From a Firearms Expert) | Bree Lee, NOLA Fire

    Sevetri and Sheena sit down with firearms expert Bree Lee, founder of NOLA Fire and one of the few women leading firearms training in New Orleans, for an eye-opening conversation about women’s safety, self-defense, and personal protection. As two entrepreneurs who travel solo for work constantly, this was a conversation they HAD to have. Bree breaks down what women should actually know to stay safe, from situational awareness and concealed carry to solo travel and rideshare safety, and shares why she’ll never take a rideshare again. In this episode, we cover: ▸ Why Bree got into firearms training as a Black woman ▸ Concealed carry laws in Louisiana—and why firearms education matters ▸ Situational awareness and why it may be your most important self-defense tool ▸ Why Uber and Lyft can present safety risks ▸ Parking garage safety rules every woman should know ▸ How social media has quietly changed personal safety ▸ Solo travel safety tips for women on the go ▸ What every mother should teach her daughters about personal safety and self-defense ABOUT BREE LEE & NOLA FIRE Bree Lee is the founder of NOLA Fire, a New Orleans-based firearms training company providing firearms education, safety training, and certification. FOLLOW BREE LEE Instagram: https://www.instagram.com/nolafirearms NOLA Fire: Firearms training & certification classes ━━━━━━━━━━━━━━━ RICH LESSONS PODCAST Hosted by Sevetri Wilson Taylor and Sheena Allen 🎧 LISTEN & SUBSCRIBE Apple Podcasts: https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124 Spotify: https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8kl ▶️ WATCH & SUBSCRIBE ON YOUTUBE https://www.youtube.com/@richlessonspodcast 📲 FOLLOW RICH LESSONS Instagram: https://www.instagram.com/richlessonspodcast TikTok: https://www.tiktok.com/@richlessonspodcast

  8. Aug 13

    Anthropic's AI Watermark, iPhone 18 Drops & the Lakers' $12.5B Sale | Rich Takes

    AI is changing how we create, consume, and even trust information, and this week on Rich Takes, we’re talking about what that means for business, technology, entertainment, and culture. Anthropic is rolling out watermarks for AI-generated text. Is this the beginning of a new era of AI transparency, or will people simply find new ways around it? We also get into the iPhone 18, Apple’s rumored shift in its release strategy, and whether consumers still see enough innovation to justify upgrading every year. Then, we jump into entertainment: Spotify is taking a stand against AI-generated music, labeling AI-created artists and keeping them out of recommendations. Is protecting human creativity the right move, or is AI simply the next evolution of how music gets made? We also talk about what we’re actually watching, why Apple TV+ has some of the best shows nobody seems to be talking about, and the rise of short-form entertainment. And just when we thought we were wrapping up, breaking news hits: the Los Angeles Lakers are reportedly being sold for a record $12.5 billion. Plus, it’s Black Business Month, so we’re talking about Black entrepreneurship, supporting Black-owned businesses, and why the conversation needs to go beyond simply starting businesses to building companies that scale. In this episode:• Anthropic’s AI watermarking and the future of AI transparency• iPhone 18 and Apple’s changing upgrade strategy• Spotify’s response to AI-generated music• What’s actually worth watching right now• Apple TV+’s surprisingly strong lineup• The rise of AI in entertainment• The $12.5B Lakers sale• Black Business Month and the future of Black entrepreneurship Rich Takes is the weekly hot-take conversation from Rich Lessons, covering the biggest stories in business, tech, finance, entertainment, and culture. Subscribe, follow, and join the conversation. Stay rich. Apple Podcasts: https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124 Spotify: https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8kl?si=9666ca84559c4e16 YouTube: https://www.youtube.com/@richlessonspodcast Instagram: https://www.instagram.com/richlessonspodcast/ TikTok: https://www.tiktok.com/@richlessonspodcast

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About

The Rich Lessons Podcast, hosted by Sevetri and Sheena, cuts through the noise with rich insights and real conversations about business, life, and everything in between—offering hard truths, valuable lessons, and stories still being written.

Information

  • Creator
    Sevetri Wilson and Sheena Allen
  • Years Active
    2024 - 2026
  • Episodes
    84
  • Rating
    Clean
  • Copyright
    © Sevetri Wilson and Sheena Allen
  • Show Website
    Rich Lessons