We Bought a Business for $1.1M and Nearly Broke

What really happens after you acquire a business? Greg shares the untold truth about buying a short-term rental property management company in the Colorado mountains—how it nearly broke him, what saved him, and the operational chaos he didn’t see coming.

In this honest and detailed conversation, Greg breaks down:

Why he walked away from VC-backed startups

What made him ditch investor funding and go self-funded

How he picked the wrong-sized business

The one employee that made or broke the business

His biggest regret after closing

How regulation became his competitive moat

Why trust accounting almost took them out

And why managing at 12,000 ft altitude is no joke

00:00 Buying at the Peak?
00:33 Greg's Backstory: From Startups to Search
01:15 Discovering ETA (Entrepreneurship Through Acquisition)
02:00 Going Self-Funded vs. Traditional Search
03:00 Pandemic Kicks Off the Search
03:40 Why They Ditched Their Investors
04:15 Realizing Investors Only Wanted “Home Runs”
05:00 Avoiding VC Governance
06:00 The Cardinal Mistake: Buying Too Small
06:31 From $500k to $380k in Real EBITDA
07:00 The Random Industries They Looked At
08:17 How They Evaluated Deals with Strict Criteria
09:00 Why They Walked Away from a Furniture Biz
09:30 Finding the Vacation Rental Biz by Accident
10:08 The Owner Had a Heart Attack Mid-Deal
10:47 Brokers That Made the Deal Happen
11:33 Why the Seller Is the Most Important Factor
12:51 Why the Seller Chose Them Over Higher Offers
14:11 Recession-Proof Real Estate in Breckenridge
15:00 Revenue & EBITDA Breakdown
15:46 Navigating Seller Expectations & Strategic Buyers
17:08 Handling the Key Employee Who Wanted to Buy the Biz
20:37 Building Trust with Staff Post-Acquisition
22:27 Retention Bonuses & Remote Team Dynamics
23:42 Local Regulations as an Operational Moat
27:22 Managing Short-Term Rental Licensing for Clients
28:53 Deal Structure & Financing (SBA + Seller Note)
30:07 Interest Rates Skyrocketed – Here’s What They Did
31:02 The $120K Self-Insurance Hack That Saved Them
33:05 Margins, Properties, and Operational Complexity
35:25 Unforeseen Challenges of Mountain Operations
38:13 Cell Signal, Altitude Sickness & Burnt-Out Bulbs
41:15 Learning to Say “No” to Unprofitable Homes
42:43 Labor Intensity, Septic Tanks & Power Outages
44:08 Revenue Per Door and Margin Pressures
46:00 Scaling from 30 to 60 Units (Without Ads)
47:20 Why Growth Doesn’t Mean Scalability
49:13 Lawsuits, Liability & Managing Insurance Risks
51:18 Why Homeowner Insurance Terms Matter
52:03 Managing Remote While Living in Chicago
53:29 Angela: The “No Equity” Owner Who Runs the Show
54:13 Remote Management Frustrations
55:02 24/7 Guest Coverage and On-Call Chaos
56:08 Realistic Compensation for a Local Ops Manager
57:10 Why They Didn’t Scale Right
58:15 What the Next Acquisition Will Look Like
59:30 Cold vs. Warm Markets: Where Should They Go Next?
01:02:13 Seasonality, High ADRs & Dual Season Advantage
01:03:39 Why They Rejected 2-Bedroom Units
01:04:13 Final Thoughts



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