One Rental At A Time From Zero to Multiple Rentals: Mike's Story
Feb 23, 2026
A wide-ranging investor origin story covering decades of deals, blunders, and big wins. He explains entitlements and the patient, procedural world of plats and approvals. Tough mitigation challenges on riverfront land and costly premature closings get candid attention. The conversation also touches on shifting jurisdictions and why some towns welcome developers.
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Turning Raw Land Into Valuable Entitled Parcels
- Mike built value by converting raw land through entitlements, turning unusable parcels into sellable lots.
- He describes entitlements as county or city permission plus conditions, not just permits, requiring persistence as plats often face repeated setbacks.
Persist Through Entitlement Setbacks
- Persist through planning setbacks because plats often fail repeatedly before success.
- Mike warns that effective entitlement work requires waking up, iterating, and trying solutions the next day rather than giving up.
Budget For The Idiot Tax When Learning Development
- Expect to be educated by mistakes and budget for expensive 'tuition' when you close deals prematurely.
- Mike admits he still owns properties he should never have closed on and calls the cost of learning the 'idiot tax'.
