Doug Breaker

Owner/CEO of CEO MDHearing, Scripted, EarthClassMail & HomeFinder. Pretend Ruby/Rails dev.

[Doug Breaker @dbreaker]

@girdley 💯

[Doug Breaker @dbreaker]

@Shpigford it's the worst

[Doug Breaker @dbreaker]

Yesterday was chainsaw training day! https://t.co/Kxn9LnY7pH

[Doug Breaker @dbreaker]

My college son decided for some adventure this summer and found a job as a wildland firefighter in Montana. Not at all stressful for a dad. :) I'm *attempting* to help him learn how to build an online business - https://t.co/HBWngFqWbp, using Claude Code. Fun stuff.

[Doug Breaker @dbreaker]

@thesamparr This is awesome. Congrats on your success @NotGoKGreen!

[Doug Breaker @dbreaker]

@Shpigford @joshpuckett @Shpigford any of those recs work for updating existing tired rails/tailwind site with a fresh design?

[Doug Breaker @dbreaker]

@PalmerLuckey https://t.co/s3jzG3zX7F

[Jason ✨👾SaaStr.Ai✨ Lemkin @jasonlk]

Just tell me what the product costs

I really dont want to get on the phone

[Jason Fried @jasonfried]

The last 20% isn't most of the work, it's all of the work.

[Matthias Smith, CEO - Pioneer Capital Advisory LLC @SBA_Matthias]

One of the top questions I get from prospective business buyers: what do multiples actually look like, and how have they moved over time?

We're one small data point in a very big M&A ocean at @PIONEERCAPADV — but here's what 68 of our closed deals from 2022 through 2026 YTD look like when you plot purchase price against multiple paid.

A few honest caveats before anyone reads too much into the chart:

• The dataset is incomplete. Banks don't always share the underlying business valuation with us, so a meaningful chunk of deals had to be excluded.
• Much of this was retroactively compiled from closing files, lender correspondence, and our own notes — not pulled clean from a system of record.
• 68 deals is a respectable sample for one shop, but it's still one shop. Treat it as directional, not definitive.

With that said — the trend lines are interesting. 2022 sits cleanly in the 2.5x–3.5x band. 2024 starts to spread upward. 2025 has the widest distribution, including a 7x SaaS outlier and the largest deal of the dataset, a consumer products transaction priced in the low-4x EBITDA range. 2026 YTD is clustering in the 3.5x–4.5x range with several notable points above 4.5x.

Full breakdown in this week's edition of the Pioneer Buy-Side Brief — link in the comments.

[Doug Breaker @dbreaker]

@chandlerreed What's your cold email stack?

[Doug Breaker @dbreaker]

@FreightAlley In. Shoeboxed has a lot of trucker customers.

[Doug Breaker @dbreaker]

@Shpigford

[Doug Breaker @dbreaker]

@noahkagan Thanks for sharing Noah, the transparency is super cool

[Doug Breaker @dbreaker]

Claude Code is drunk today

[Matthias Smith, CEO - Pioneer Capital Advisory LLC @SBA_Matthias]

2026 will be the year of the acquisition entrepreneur - the business buyer that wants a better life for themselves and their family and wants to pursue the American dream 🇺🇸

My team is here to support you. We have helped over 140 business buyers accomplish this journey in the last 4 years

If you’re under LOI and are looking to connect, please feel free to reach out via email at [email protected]

[Doug Breaker @dbreaker]

@Shpigford Ship it Josh. Ship it real good.

[GREG ISENBERG @gregisenberg]

You ever notice that some people say "lifestyle business" like it's some sorta slur??

One that pays well, gives you time back, and doesn't require you to sacrifice your health and relationships for a 0.1% chance at an IPO.

How embarrassing.

A small team, maybe 3 to 5 people, doing maybe $2 to $5 million a year, profitable from day 1, that you can sell one day for $10 million and set yourself and your kids up forever.

Yeah, a business designed around your actual life. And who knows, can give you the flexibility to swing for the fences if you want.

Gross!

[Michael Girdley @girdley]

How to make money on the internet:

1) Build an audience
2) Do business with them

[Doug Breaker @dbreaker]

@Shpigford @RumoredAI bought mine for https://t.co/cYJND2oTki!