CEO Lounge

Derrick Thompson & Joselyn Flores

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ENTREPRENEURSHIP

The CEO Lounge helps current and future entrepreneurs build real, sustainable success through mentorship, mindset, and proven strategies. Hosted by 30-year entrepreneur Derrick Thompson and co-host Joselyn Flores, each episode delivers authentic insights and practical guidance you can use immediately.

11H AGO

“I’m Busy” Isn’t a Flex: How Hustle & Comfort Both Stop Progress

Here’s how you can find the middle ground that actually grows you because hustle culture and comfort culture can both wreck your momentum 👇 In this episode of The CEO Lounge, Derrick Thompson and co-host Joselyn Flores break down why being “busy” isn’t the goal — progress is. They talk about the difference between profitable, purposeful grind and busy work that burns you out, plus how to spot the red flags when hustle turns unhealthy. You’ll hear practical leadership insights on: Why “I’m busy” can be a warning sign (not a flex)How to protect your time and stop saying yes to everythingWhy grinding must be seasonal with a clear end goalSystems + people (not chaos) as the real path to scaleThe mindset shift: outlast most people, don’t outwork everyone🎧 Subscribe for more leadership + entrepreneurship conversations from real experience, not theory. Chapters: 0:00 Busy vs profitable grind 0:30 Hustle vs comfort extremes 3:25 Protect your time (power of “no”) 6:54 Busy work = burnout (no progress) 11:53 When hustle turns unhealthy 14:12 Grind seasons need an end date 22:05 Systems + people (not chaos) 34:04 Outlast mindset + real balance

40 min
JAN 16

Balancing Multiple Ventures Without Burning Out (CEO Calendar System)

Everyone talks about running multiple ventures — but almost no one talks about how to do it sustainably without burning out or neglecting the business that pays the bills. In this episode of The CEO Lounge, Derrick Thompson breaks down the exact calendar system he uses to balance multiple ventures while staying focused, profitable, and sane. Derrick isn’t sharing theory — this is lived experience from a CEO who runs a digital marketing agency, community initiatives, multiple podcasts, and passion projects without chaos. In this episode, we cover: • Why planning your week on Monday means you’re already behind • How Derrick plans his entire week before Monday (weekend planning strategy) • His exact weekly structure: Monday: Client relationship & check-ins Tuesday & Thursday: Batched meetings Wednesday: Work on the business (systems, strategy, execution) Friday: Creative work, vision, and future ventures • Why your “main thing” must stay the main thing — even with exciting side projects • How to avoid shiny-object syndrome while still building long-term ventures • The calendar, systems, and tools that make managing multiple ventures possible This episode is for entrepreneurs who feel pulled in too many directions and want clarity, structure, and sustainability — not hustle culture. Chapters: 0:00 When entrepreneurs lose control of their time 0:29 Welcome to The CEO Lounge Podcast 2:18 What it really means to balance multiple ventures 3:19 Why planning your week on Monday puts you behind 9:40 Monday as Client Relationship Day 15:51 Why batching meetings reduces burnout 21:19 Structuring your week to protect energy and focus 27:24 Systems and tools that keep businesses running 38:30 Why your main business must stay the priority 47:10 How new ventures are built sustainably 58:00 Final takeaways + CEO Weekly Operating System 👉 FREE RESOURCE: Download the CEO Weekly Operating System + Calendar Framework Website - www.theceolounge.net Direct Resource Link - https://www.theceolounge.net/downloads/ceo-framework 🎧 Subscribe for weekly conversations on leadership, business growth, and running your week like a CEO. 🔔 #BalancingMultipleVentures #EntrepreneurLife #CEOSystems #BusinessLeadership #TimeManagement #WorkweekPlanning #TheCEOLounge

59 min
JAN 2

Don’t Quit in the Middle: Entrepreneur Mindset + Weekly Wins That Keep You Going - EP 3

Most entrepreneurs don’t fail from lack of talent — they quit in the middle… right before it starts working. If you’re building a business and you feel stuck, tired, or unseen, this CEO Lounge episode is for you. Derrick and Joselyn break down the middle season of entrepreneurship — the nights no one claps for, the discipline it takes to keep going, and how to protect your entrepreneur mindset with weekly wins that stack into real momentum. In this episode, you’ll learn: ✅ How to stay motivated when results are slow ✅ Why “applause” is a trap (and conviction is the fuel) ✅ The 1:00am grind story that built the foundation ✅ How to set weekly goals, celebrate wins, and avoid burnout ✅ How to know if you’re in a breakdown… or on the edge of a breakthrough 📌 Want more CEO Lounge clips + the full episodes? Subscribe today! — CHAPTERS 00:00 Protect your mindset in the middle 00:55 Welcome + why “the middle” matters 03:55 “Nobody claps for the nights you don’t quit” 06:05 The 1:00am office grind story (what people don’t see) 10:40 Leading without applause (conviction vs attention) 13:15 Why most people quit in the middle 15:35 Weekly wins: how Derrick stayed motivated 17:45 Rewards, discipline, and celebrating progress 20:00 Leading yourself before leading a team 30:05 Applause vs conviction + “breakdown or breakthrough?” 36:25 Someone is always watching (even in the unseen season) 41:35 Fatherhood + “no turning back” mindset 42:40 Redefining success: time, freedom, and peace 44:25 If you feel unseen: what to do next 50:20 Audience Q: What do I focus on first? (and when?) 52:35 Audience Q: Mindset + gratitude in the middle 58:00 When plans take longer than expected (resetting) 1:00:14 Closing encouragement 1:00:38 Bonus: 12:20am “this is what it takes” clip — #EntrepreneurMindset #StartupLife #BusinessOwner #Leadership #CEO

1h 2m
12/29/2025 · BONUS

How Do I Get Clients? Why Networking Didn’t Work for Me | CEO Lounge Ep. 2 (CLIP)

How do I get clients? It’s one of the most common questions entrepreneurs ask — and the answer isn’t always what you think. In this segment from Episode 2 of The CEO Lounge, Derrick Thompson explains why networking events didn’t bring him his biggest clients — and what actually did. Instead of chasing handshakes and business cards, Derrick built long-term growth through: Personal introductionsRelationships built over yearsBeing seen doing the workConsistency, credibility, and trustYou’ll hear how former coworkers, community connections, and people who witnessed his work ethic became the gateway to his largest clients — often years later. This conversation covers: How to get clients without relying on networking eventsWhy visibility matters more than pitchingWhat to do if you don’t have clients yetHow donating work strategically can open doorsWhy relationships outperform cold outreach over timeIf you’ve ever asked yourself, “How do I get clients?”, this segment reframes what actually works. The CEO Lounge is your blueprint for success — real experience, real strategy, and real lessons for entrepreneurs building something that lasts. 📌 This clip is from Episode 2 - You’re NETWORKING WRONG: How Real Business Connections Actually Happen | CEO Lounge Ep. 2 🎧 New episodes drop the 1st and 3rd Fridays 🔔 Subscribe so you don’t miss what’s next ⏱️ Chapters 00:00 How Do I Get Clients? 00:09 Why Networking Didn’t Bring My Biggest Clients 00:25 Where My Top Clients Actually Came From 00:45 The Power of Personal Introductions 01:03 Why Long-Term Relationships Win 01:21 Why Business Cards Don’t Build Trust 01:49 When Networking Events Disappoint 02:12 Being Seen Doing the Work 02:34 What to Do If You Don’t Have Clients Yet 02:58 Why Donating Work Can Open Doors 03:18 Relationships vs. Cold Outreach

4 min
12/24/2025 · BONUS

Stop Chasing New Clients: Let Referrals Do the Work | CEO Lounge Ep. 2 (CLIP)

If you’re constantly chasing new clients, this might be the real reason business feels harder than it should. In this segment from Episode 2 of The CEO Lounge, Derrick Thompson explains why the best referral source you’ll ever have is the client you already have — and why desperation quietly kills deals before they even start. Clients can sense confidence. They can also sense need. And when you’re “thirsty” for work, it becomes a turnoff — even if your service is excellent. In this conversation, Derrick breaks down: Why referrals outperform traditional marketingHow happy clients become your strongest sales teamThe hidden danger of chasing every new opportunityWhy desperation repels the very clients you wantHow confidence and consistency create inbound demandIf you can master getting your customers to talk about you, you won’t have to market nearly as hard — they’ll do the work for you. The CEO Lounge is your blueprint for success — real conversations, real experience, and real strategy to help you grow the right way. 📌 This clip is from Episode 2 → You’re NETWORKING WRONG: How Real Business Connections Actually Happen | CEO Lounge Ep. 2 🎧 New episodes drop the 1st and 3rd Fridays 🔔 Subscribe so you don’t miss what’s next ⏱️ Chapters 00:00 Why Your Best Referral Is Your Current Client 00:18 How Referrals Create Effortless Growth 00:36 Why Happy Clients Sell Better Than Ads 00:59 “If Clients Talk About You, You Don’t Have to Market” 01:10 The Biggest Mistake in Business Relationships 01:16 Why Desperation Turns Clients Away 01:37 Confidence vs. Need in Sales Conversations 02:04 Why Chasing Clients Signals a Bigger Problem 02:26 The Mindset Shift That Changes Everything

3 min
12/20/2025

You’re Networking Wrong: How Real Business Connections Actually Happen | CEO Lounge Ep. 2

Most people don’t struggle with networking because they lack effort — they struggle because they’re doing it wrong. In Episode 2 of The CEO Lounge, Derrick Thompson and co-host Joselyn Flores break down why traditional networking advice fails entrepreneurs — and what actually builds real business relationships. If you’ve ever: Left a networking event exhausted with nothing to show for itCollected business cards that went nowhereWondered why some people always get the call backThis episode is your blueprint. Instead of chasing contacts, this conversation dives into: Why real networking rarely happens in crowded roomsHow timing, value, and intention matter more than small talkA real story of how one fundraiser conversation turned into a high-level business connectionWhen to follow up — and when not toHow to add value first without sounding salesy or desperateThis isn’t theory. It’s real-world strategy from entrepreneurs who’ve built businesses through relationships, trust, and long-term thinking. The CEO Lounge is your blueprint for success — designed to help aspiring founders, startups, and seasoned entrepreneurs make smarter moves without wasting years learning the hard way. 🎧 New episodes drop the 1st and 3rd Fridays 📅 Episode 2 is live now 📌 Subscribe so you don’t miss what’s next 🔑 KEY TOPICS COVERED Business networking strategiesEntrepreneur networking tipsHow to follow up with executivesRelationship-based marketingBuilding trust in businessStartup mistakes in networkingHow to add value before asking If this episode helped you rethink networking, drop a comment below or share it with someone who needs to hear this.

38 min
12/06/2025

Should You Leave Your 9–5? | Mentorship, Risk, Mindset & The Real Path to Becoming a CEO - EP 1

Welcome to the very first episode of The CEO Lounge — Your Blueprint for Success. In this powerful introduction episode, 30-year entrepreneur Derrick Thompson and co-host Joselyn Flores break down the foundational lessons every new and aspiring entrepreneur needs. From mentorship to managing risk to knowing when (or if) you should leave your 9–5 job, this episode sets the tone for what The CEO Lounge is all about: real talk, real strategy, and real guidance. If you're thinking about starting a business, stuck between comfort and calling, or trying to understand what it truly takes to become a CEO — this episode gives you clarity. WHAT YOU’LL LEARN IN THIS EPISODE: • How to choose the right mentor • Derrick’s #1 piece of advice for new entrepreneurs • How to know when it’s time to leave your 9–5 job • What real “risk management” looks like • The mindset and traits real CEOs share • Sweat equity vs outside funding • How to build relationships that move your life forward • How to deal with setbacks and failure • Why sacrifice is essential • How to price your work properly • Why Plan B can actually sabotage your dreams • And how to test if your idea is a hobby or a real business New episodes drop 1st & 3rd Friday of every month at 7 PM EST.

53 min

7 Episodes

The CEO Lounge helps current and future entrepreneurs build real, sustainable success through mentorship, mindset, and proven strategies. Hosted by 30-year entrepreneur Derrick Thompson and co-host Joselyn Flores, each episode delivers authentic insights and practical guidance you can use immediately.

Creator

Derrick Thompson & Joselyn Flores
Years Active

2025 - 2026
Episodes

7
Rating

Clean
Copyright

© 2026 CEO Lounge
Show Website

CEO Lounge