The Truth About Capital and Buying a Landscaping Business - Colton Imming
What's Your Deal? | Business Buying, Business Acquisitions, Investing & Exit StrategiesShow Notes
In this episode of What's Your Deal?, Matt Uhler sits down with Colton Imming, to unpack what it really looks like to leave a W2 career behind, bet on yourself, and step into business ownership.
Colton shares his path to a private equity environment that rewarded performance — and how a long-term plan with his wife, Katie, helped them prioritize freedom, family, and control over their time. That journey eventually led to Colton partnering with two others to build a holding company focused on acquiring and stewarding small businesses.
From there, the conversation goes into the real-world lessons you only learn after closing: why proximity matters, what happens when you lose a major client, why "easy upside" improvements like adding a CRM can be a much heavier lift than expected, and the critical importance of being well-capitalized so you're making decisions for the long-term — not just trying to survive payroll.
Matt and Colton also discuss a topic buyers rarely hear addressed openly: the reality of working with the listing broker when there's no separate buyer representation, and how trust, communication, and education can make or break the process.
To close, Colton gives a high-level preview of his perspective on Bitcoin — not as a trend, but as a deeper conversation about money, value, and long-term thinking — and shares who gave him a "hand up" on his path.
Timestamps:
00:16 – Colton's background (E&Y → PE → family-first move)
03:25 – Leaving the W2 ladder: mindset + planning for freedom
08:16 – Quitting PE: notice, golden handcuffs, betting on himself
11:06 – Starting an accounting firm + investing alongside it
12:29 – Forming the 3-partner holding company (CEO/COO/CFO lanes)
16:57 – What they looked for in an acquisition (local + recurring revenue)
18:48 – Lessons after closing: trucks/fleet, culture upgrades, professionalism
25:40 – Tech + systems: CRM implementation is heavier than expected
29:56 – Losing a major client + why working capital matters
33:00 – Listing broker dynamic: buyer-side trust + efficiency
41:35 – Colton's advice to buyers: capitalization > everything
43:42 – Bitcoin philosophy: money, value, and long-term thinking
49:28 – "Hand up" gratitude segment + closing
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