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

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#BalancingMultipleVentures
#EntrepreneurLife
#CEOSystems
#BusinessLeadership
#TimeManagement
#WorkweekPlanning
#TheCEOLounge

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!

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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

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#EntrepreneurMindset #StartupLife #BusinessOwner #Leadership #CEO

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 introductions
• Relationships built over years
• Being seen doing the work
• Consistency, credibility, and trust

You’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 events
• Why visibility matters more than pitching
• What to do if you don’t have clients yet
• How donating work strategically can open doors
• Why relationships outperform cold outreach over time

If 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

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⏱️ 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