Three Headed Monster Portfolio

Nick Huber reflects on how his confidence and assumptions about business success were humbled over the past five years. He believed that a strong personal brand could carry any agency business to success, but market changes and algorithm shifts proved him wrong. His experience running 11 companies revealed harsh realities about entrepreneurship.

Key Realizations:

• Early Overconfidence Was Valuable But Misguided:

  • Five years ago, he felt like he "knew everything"
  • That irrational confidence led to putting himself out there and early success
  • Wouldn't trade that confidence because it drove action
  • But it masked the true difficulty of building sustainable businesses

• The Personal Brand Myth:

  • Believed a strong enough personal brand could make any agency business "go to the moon"
  • Thought you could do "a couple things right couple things wrong whatever" and still succeed
  • Reality: The algorithm changed, business got harder, people watched spending more carefully
  • His ability to drive leads through Twitter vanished when Elon changed the platform

• Market Conditions Matter More Than Believed:

  • 2024-2025 are fundamentally different from 2022-2023 for every entrepreneur he knows
  • Many people are making less money now than three years ago
  • "Everyone's a genius in a bull market" - the easy times masked poor fundamentals

• Portfolio Reality - Power Law Dynamics:

  • Started 11 companies between 2016 and recent years
  • Shut down 4 companies completely
  • 2 are "treading water"
  • Only a "three headed monster" of top companies actually drive cash flow
  • The bottom 6 companies generated maybe $500K/month in revenue at peak
  • Current group cash flow is actually higher, but only because of the top 3

• What He Got Wrong:

  • Building executive teams is not easy
  • Customers don't "just come"
  • Business fundamentals matter more than audience size
  • You can't rely on social media algorithms for sustainable lead generation

• The Harsh Truth:

  • "Business is hard. Business is really hard."
  • Most ventures in a portfolio will fail or underperform
  • Success requires more than confidence and a following