The UpFlip Podcast

208. The Boring 8-figure Business Hiding in Plain Sight

13 snips
Oct 13, 2025
Andrew's journey from a $13/hour job to a thriving service business showcases the power of taking risks. After being deemed 'replaceable' in corporate, he liquidated his 401(k) to invest in a friend's tree-cutting side hustle. With a near-zero marketing budget, Andrew emphasizes clever tactics like using Reddit for free leads and tapping into personal networks for initial sales. He shares how simple yet bold offers can attract customers and highlights the importance of maintaining quality and responsiveness in service.
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ANECDOTE

Quit After Being Told ‘Replaceable’

  • Andrew left a six-figure corporate sales job after a regional manager told him he was "replaceable."
  • He used that moment to reset and later join his friend's tree business full-time.
ANECDOTE

Swapped Corporate Stress For Hands-On Work

  • Andrew started working three days a week for his friend Austin doing physical tree work while enjoying the lower stress.
  • He found the hands-on work restorative and his TMJ jaw issue disappeared after leaving corporate life.
ANECDOTE

Used 401(k) To Buy Into The Business

  • Andrew liquidated his 401(k) to buy a partnership stake in Tree Amigos because he distrusted the long-term value of retirement accounts.
  • He believed active sweat equity today outweighed waiting decades for modest retirement returns.
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