WIP 1886: The 5 Fears I Had to Overcome Before Making Millions in Wholesaling

Dec 15, 2025

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Fear is part of the game, but it does not get to decide your future.

In this episode, Todd Toback shares five real fears he faced on his path from sending handwritten letters and using fax machines to building a multi-million-dollar wholesaling business. He talks about feeling unprepared, leaving a six-figure job, spending real money on marketing, hiring a team, and stepping into completely new asset classes. Each fear became a turning point that pushed him toward greater growth.

If fear has been holding you back, this episode is your reminder that confidence comes after you take action, not before it.

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Show notes:

(0:50) Beginning of today’s episode
(1:09) Todd sets up the 5 fears he had to overcome in real estate
(1:42) Fear #1: Not having the right tools (handwritten letters, no CRM, no systems)
(3:52) Taking imperfect action and closing his first deal without contracts or funding lined up
(4:25) How one phone call led to a $40,000 payday
(5:09) Fear #2: Quitting a high-paying job and stepping into the unknown
(6:23) How surviving a market crash made Todd a stronger investor
(7:33) Fear #3: Spending real money on marketing
(8:32) Turning $7,500 in mailers into a $38,000 deal
(9:55) Fear #4: Hiring people and building a team
(11:20) Why not hiring is actually more dangerous than competition
(12:34) Fear #5: Investing in new asset classes outside of single-family homes
(13:50) Defining “no-brainer” deals to reduce risk and fear
(15:07) Dan Sullivan’s 4 Cs: Commitment, Courage, Competence, Confidence
(18:01) Why confidence only comes after you jump

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Resources:

Dan Sullivan – The 4 Cs Framework
Book referenced: Multiple Streams of Income by Robert Allen
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