Investment Philosophy and Operational Insights

My comprehensive year in review covering personal achievements, business developments, and investment strategies in 2024. I share a detailed breakdowns of my wealth allocation, business portfolio performance, and social media growth. The review emphasizes a shift toward business simplification, increased focus on AI and technology integration, and the importance of building sustainable, scalable ventures.

Timestamps:
00:00 - Intro
01:38 Biggest wins
05:54 Biggest losses and lessons
11:47 - Q&A from social media
18:00 - Growth across social platforms
25:00 - Wealth breakdown and investments
33:03 - Business updates
48:16 - Productivity gains
50:48 - New insights and learnings

Key Points:
• Personal milestone of having first child and significant net worth achievement
• Business portfolio performance across Late Checkout Agency, Boring Marketing, and other ventures
• Portfolio breakdown: 75% stocks, 16% private equity, 7% real estate, 2% crypto
• Platform growth across YouTube (11K to 146K subscribers), X/Twitter (361K to 420K followers)
• Strategic shift toward simplification and focus on building "skyscrapers, not strip malls"

1) BIG WINS 2024:

• Had a baby 
• Started lifting consistently (+15-20 lbs muscle)
• Grew podcast into major platform
• Hit personal net worth milestone

2) Portfolio breakdown (fascinating):

• 75% stocks
• 16% private equity
• 7% real estate
• 2% crypto

Top holdings:
• 10% Berkshire
• 10% SPY
• 8% Apple
• 7% Amazon

3) Business Updates:

Late Checkout Agency (LCA):
• Found their niche: AI interfaces + community products
• Booked solid with major brands
• Started taking equity deals with billion-dollar companies

 Boring Marketing & Boring Ads:

• Both crushing it
• $100M+ in ad spend managed
• 76 meetings booked in next few weeks
• Unbundling tools for DIY customers
• Created Boring Holdings umbrella company

5) Key productivity unlocks:

• Switched to Yerba Mate for afternoon energy
• Simplified from Notion to Apple Notes
• Using Things app for to-do lists
• Less tools, more focus

6) Platform Growth 2024:

YouTube: 11K → 146K subs
X: 361K → 420K followers
LinkedIn: 82K → 149K
Newsletter: 72K → 120K subs
Podcast: 360K → 575K downloads

7) Best decision framework:

"Friday Afternoon Test"

- Only make big decisions Friday PM when tired
- If it still feels right then, it's probably right
- Prevents caffeine-fueled impulse choices

8/ MAJOR hiring insight:

"Day Zero Integrity Test"
• Give unclear instructions for small task
• See if they ask questions or just guess
• Reveals everything about future behavior

9/ Key lessons:

• Trust but verify (especially with remote teams)
• Simple over Complex
• Double down on what's working
• Build skyscrapers, not strip malls
• Tech investment over immediate profits

10) 2025 Focus:

• Finding long-term business partners
• Building more proprietary tech
• Simplifying business structure
• Going harder on current opportunities
• Scaling what works

Notable Quotes:
"If this scales, do I want to be in that business? If not, what is the business that I want to be in?"
"My main mission is to build skyscrapers, not strip malls."

Want more free ideas? I collect the best ideas from the pod and give them to you for free in a database. Most of them cost $0 to start (my fav)

Get access: https://www.gregisenberg.com/30startupideas

LCA helps Fortune 500s and fast-growing startups build their future - from Warner Music to Fortnite to Dropbox. We turn 'what if' into reality with AI, apps, and next-gen products https://latecheckout.agency/

BoringAds — ads agency that will build you profitable ad campaigns http://boringads.com/

BoringMarketing — SEO agency and tools to get your organic customers http://boringmarketing.com/

Startup Empire - a membership for builders who want to build cash-flowing businesses [https://www.startupempire.co](https://www.startupempire.co/)

FIND ME ON SOCIAL

X/Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
LinkedIn: https://www.linkedin.com/in/gisenberg