Today’s guest is someone I’ve admired for a while now not just for what he’s building, but for how he’s building it. Tim Olson is the managing partner of Aspire Finance, and in this episode, we walk through his journey from a commission-only equipment finance rep to launching a nationwide lending firm, acquiring companies, and raising capital for real estate syndications all while staying grounded, humble, and hungry.
We talk about fast money, medium money, slow money, how to align your business with your values, and why consistency and curiosity are two of the greatest traits any entrepreneur can develop.
This one’s for the connectors, the visionaries, and the people who want to own their life instead of just making a living.
Key Talking Points of the Episode
00:00 Introduction
02:51 Who is Tim Olson? 04:27 Tim’s start in banking, sales, and relationship-building
09:25 When the entrepreneurial bug started to bite
11:01 The power of curiosity and genuine connection
15:19 Learning to speak less, listen more, and win trust
18:32 Fast, medium, and slow money
21:38 Building Aspire Finance with Kelly Garrett & team
28:10 The value of partnerships and staying in your lane
31:22 Acquiring legacy businesses from retiring owners
33:22 Focusing on culture when acquiring businesses
36:15 Structuring acquisitions: SBA loans, seller financing, rollovers
39:36 Raising capital for multifamily real estate
43:14 Vetting real estate operators and avoiding bad deals
47:20 Fitness, cold plunges, and daily mental reps
55:21 How to enforce accountability in your life
01:02:33 Get in touch with Tim!
Quotables
“Fast money puts food on the table. Medium money builds wealth. Slow money creates legacy.”
“You’re not a better entrepreneur because you grind harder. You’re better because you get clearer.”
“I don’t want to just raise money—I want to build trust that lasts decades.”
Links
Tim Olson
https://www.facebook.com/timothylee87
https://www.instagram.com/tim.olson.1/
608B Capital
