The Challenges and Lessons of Finding a Business to Buy — Cristian Cruz
What's Your Deal? | Buying Businesses, Business Acquisitions, Investing & Exit Strategies
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Show Notes
In this episode of What's Your Deal?, Matt sits down with Cristian Cruz, a former Miami firefighter who walked away from a secure career and pension to pursue entrepreneurship and business ownership. Cristian shares his bold decision to leave behind stability for opportunity, his first steps into startups, and why he's now focused on buying an established business instead of building from scratch.
This candid conversation dives into risk, motivation, family legacy, and how Cristian is approaching his first acquisition with patience, direction, and clarity. If you've ever wondered what it takes to leave the safety of a W2 job and step into the uncertain but rewarding world of business ownership, you'll find inspiration and practical lessons here.
Timestamps0:16 – Introducing guest Cristian Cruz and his background
1:49 – Becoming a Miami firefighter at 21 and "winning the lottery" career
4:02 – Starting his first business in credit repair
5:26 – Jumping from a secure W2 to entrepreneurship
6:32 – Understanding risk: firefighting vs. business ownership
8:10 – Hitting the career ceiling and choosing entrepreneurship instead
10:00 – Why Cristian shifted from startups to buying an existing business
12:14 – The overwhelm of too much information when starting the search
13:43 – Discovering the cleaning industry as a realistic acquisition target
14:50 – Matt explains the Buyer's Acquisition Formula
16:46 – Learning to compress timelines by asking questions and seeking mentors
18:32 – Realizing acquisitions take longer than expected
20:00 – Avoiding deadline pressure and rushed decisions
21:47 – How Cristian is sustaining himself financially during the search
23:29 – Different circumstances: supporting a family vs. pursuing solo
24:50 – Why Cristian prefers direct outreach over online business listings
28:56 – Stacking capital and preparing for a larger acquisition
30:10 – Matt shares his roots in the janitorial industry and how it led to brokerage
31:20 – The role of family and parents' sacrifices in Cristian's motivation
36:40 – Biggest lesson learned: not every "guru" is worth listening to
38:34 – Compressing time by learning from others' mistakes
Resources & Links
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