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What’s Changed In 5 Years of Acquisition Entrepreneurship

I’m writing this as of November 2025. It’s been 5 years since I was searching to buy a business, and it’s been nearly 4 years since I closed on my first acquisition. A lot has changed for buyers in terms of education, financing, and competition. This post is a breakdown of what I’ve seen change [ ]

The Half Way Point

I’m just over 2.5 years into buying an accounting firm. The time has flown by and it’s been quite the rollercoaster ride. I ended up buying two more firms within my first 12 months. Revenue went from $1.2M before I bought it to $3.3M in our second year. The team grew from 12 to about [ ]

Pizza, French Fry, and the J-Curve

Buying a small business is EXACTLY like teaching your kids to ski. The J-curve gets ugly before it gets fun. How you imagine it ll go: How it actually goes the first 12-24 months: Finally things start to change 24-36 months in:

How To Self Implement EOS

There s a lot of buzz about EOS, or the Entrepreneurial Operating System. Many small to mid size business owners talk about flailing for years then EOS saving their business, or EOS leading to massive growth, or EOS finally making it feel like the business can run on its own. I m a big fan and have [ ]

How To De-Risk Acquisitions

I bought three accounting firms within 12 months. Every single week I picture a win probability graph that changes like a live NFL game: In order to buy Appletree in late 2021 I quit my job, used 80% of our savings, and signed a personal guarantee on a big SBA loan. And we d just moved [ ]

Favorite Podcasts of 2022

Podcasts, twitter, books, newsletters, blogs. That s where my learning comes from these days in that order. So I dug through my notes and found my 5 favorite podcast episodes from 2022. The ones that made me stop in my tracks, write things down, and listen again. PS here s my favorite podcasts of 2021 [ ]

Avoiding The 7 F Bombs: How To Create Financial Health In Your Small Business

A growing small business eats cash. Nom nom nom all the way to mature stability. And like my kids it probably wants to eat cash unexpectedly and snack at inconvenient times. Up until $3-5M in revenue there’s a few F bombs to avoid along the way. These F bombs are financial setbacks that will either [ ]

Are Holding Companies worth it? Takeaways from HoldCo Conf.

There’s a bunch of fellow nerds on Twitter who romanticize the idea of a Holding Company. And this past week, us nerds gathered in Cleveland for the first annual HoldCo Conference. The conference founders are John Wilson and Kelcey Lehrich. John has bought and built 10-12 home services businesses in northeast Ohio that include plumbing, [ ]

Reflections 90 Days Post Close

This week will be 90 days since I officially closed on Appletree on December 31st 2021. We’ve had challenges but it’s gone much smoother than I expected. A lot of credit goes to the previous owner, Steve, for his work and diligence in the transition. (PS just for context Appletree does quality bookkeeping, payroll [ ]

Why I Bought a Bookkeeping Company

You did what now? Yep! Here s why: Why buy a bookkeeping firm? The last few years I was doing small business advising and kept seeing bad, out dated bookkeeping. So we d refer clients over to a good option and it was transformative. Clients suddenly had up to date financials, they started to understand their numbers, [ ]