Rich Lessons

Should your wealthy best friend pay for you to fly first class?This week on Rich Takes, Sheena Allen and Sevetri Wilson Taylor jump into the viral debate surrounding Savannah James and April McDaniel traveling in different classes on an international flight. If you have the money, should your best friend be sitting in first class with you, or is no one entitled to someone else’s wealth?That opens up a bigger conversation about friendship, money, the difference between being rich and being wealthy, and what generosity looks like when the financial gap between friends is huge.Then, Sheena and Sevetri talk about the growing number of food recalls and the question many consumers are asking: what is actually safe to eat?Plus, they take on the viral “worth the money” debate. From first-class flights and comfortable shoes to DoorDash, house managers, childcare, personal chefs, trainers, travel, and executive assistants, what purchases genuinely make life better—and which luxuries are actually worth paying for?Rich Takes is the weekly hot-takes series from Rich Lessons, where Sheena and Sevetri break down the trending conversations in money, business, culture, lifestyle, and everything people are debating online.New Rich Takes every Thursday on Spotify and Apple Podcasts.---Apple Podcasts: https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124Spotify: https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8kl?si=9666ca84559c4e16YouTube: https://www.youtube.com/@richlessonspodcastInstagram: https://www.instagram.com/richlessonspodcast/TikTok: https://www.tiktok.com/@richlessonspodcast

If you're building something right now, this is the episode we wish we had when we started.Between the two of us we've bootstrapped, raised millions, run venture-backed companies, and started all over again. And every single one of those seasons came with a lesson we had to learn the hard way.So we sat down and went through them. The real ones.Whether you can actually protect your peace while you're launching (one of us thinks soft life is a lie). How to take a no without taking it personally, and why you should never screenshot an investor's rejection and post it. The email that turned a no into a yes in two hours. Why money just helps you make mistakes faster if you don't know how to use it. Why people buy outcomes, not features. And the call Sevetri will never reschedule.Whether you're running a startup, a restaurant, a service business, or you're still figuring out the idea, this one applies to you.Tell us which lesson hit the hardest 👇🏾━━━━━━━━━━━━━━━WHAT WE GET INTO▸ Protecting your greatest asset: you▸ Is soft life actually possible when you're launching?▸ Why Sevetri doesn't do 3 AM calls anymore (and Sheena still does)▸ Taking a no personally vs professionally▸ The founder "anti-list" — yes, we remember every no▸ The email that turned an investor's no into a yes in two hours▸ Please don't screenshot your investor rejection on LinkedIn▸ "$500K is a lot of money… until you raise it"▸ The art of the follow-up (even when you don't need anything)▸ Cash is oxygen — and why capital helps you make mistakes faster▸ People buy outcomes, not features▸ Delegation, firing fast, and why the CEO role changes every year▸ Mentors vs sponsors — and the no-show that ended it before it started▸ Hiring for your weakness until it becomes your superpower━━━━━━━━━━━━━━━MENTIONED IN THIS EPISODEOur episode with Deb Grant: https://youtu.be/myAw1Xy6kJE━━━━━━━━━━━━━━━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 YOUTUBEhttps://www.youtube.com/@richlessonsp...📲 FOLLOW RICH LESSONSInstagram: https://www.instagram.com/richlessons...TikTok: https://www.tiktok.com/@richlessonspo...━━━━━━━━━━━━━━━#RichLessons #EntrepreneurLessons #StartupAdvice #FounderLessons #Entrepreneurship #Fundraising #SmallBusiness #WomenFounders #Networking #Mentorship #BusinessPodcast #FounderMindset #CEOLife

Are we in a recession, or are the warning signs already showing up in everyday life?In this episode of Rich Takes, Sheena Allen and Sevetri Wilson Taylor break down the economic headlines raising some serious questions about where things are headed.First up: Atlanta’s surge in evictions. With eviction filings climbing and Black renters disproportionately affected, Sheena and Sevetri discuss whether rising evictions, credit card debt, job losses, housing costs, and financial pressure are signs of deeper cracks in the U.S. economy, especially for the middle class and Black households.Then, the conversation turns to Washington: Should elected officials be allowed to actively trade investments while in office? The hosts react to recent headlines surrounding Donald Trump’s securities trading activity and the broader, long-running debate over members of Congress trading while having access to information and decisions that can move markets.And what about that “$5,000 check”? Sheena and Sevetri discuss the proposal, why consumers shouldn’t count on money that hasn’t materialized, and what economic promises can look like when households are already feeling squeezed.From Atlanta’s eviction crisis and recession warning signs to debt, the disappearing middle class, political stock trading, and the proposed $5,000 checks, this week’s Rich Takes asks a bigger question: What is the economy actually telling us right now?——Rich Takes is the hot-takes mini-series from Rich Lessons, where Sheena Allen and Sevetri Wilson Taylor unpack the headlines everyone is talking about across money, business, entrepreneurship, technology, culture, entertainment, lifestyle, and politics.——Follow Rich Lessons on Spotify and Apple Podcasts, and follow us on Instagram, TikTok, Facebook, and YouTube for more conversations and clips.Apple Podcasts: https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124Spotify: https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8kl?si=9666ca84559c4e16YouTube: https://www.youtube.com/@richlessonspodcastInstagram: https://www.instagram.com/richlessonspodcast/TikTok: https://www.tiktok.com/@richlessonspodcast

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

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 AllenLISTEN & SUBSCRIBEApple Podcasts: https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124Spotify: https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8klWATCH & SUBSCRIBE ON YOUTUBEhttps://www.youtube.com/@richlessonspodcastFOLLOW RICH LESSONSInstagram: https://www.instagram.com/richlessonspodcastTikTok: https://www.tiktok.com/@richlessonspodcast━━━━━━━━━━━━━━━#RichLessons #HiringOnABudget #Freelancers #Upwork #Offshoring #StartupAdvice #Entrepreneurship #SmallBusiness #Bootstrapping #FounderMindset #WomenInBusiness #BusinessPodcast #FractionalWork