Joined March 2007
50 Photos and videos
Doug Breaker retweeted
It's ridiculous that health insurance is tied to employment. It's even more ridiculous that if you don't have the money, you have to wait much longer for an appointment, and you can't access the best facilities or best doctors. And it's even more ridiculous that people who are in the midst of the worst moment of their life have to get on the phone and fight with an employee at an insurance company in order to proceed with their treatment. It's also ridiculous that my friend, a kids gastro specialist, spent two hours carefully removing a wedding ring from a child's stomach - and made like $29. The whole thing is so broken, and frankly it is a national embrassement.
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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 - woodlandfirefighter.com, using Claude Code. Fun stuff.

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Yesterday was chainsaw training day! instagram.com/p/DY5_elLvENK/
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Doug Breaker retweeted
Just tell me what the product costs I really dont want to get on the phone
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Doug Breaker retweeted
The last 20% isn't most of the work, it's all of the work.
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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.
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Claude Code is drunk today
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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 deals@pioneercap.com
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Doug Breaker retweeted
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!
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Doug Breaker retweeted
How to make money on the internet: 1) Build an audience 2) Do business with them
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Doug Breaker retweeted
you've heard of fractional CFOs, but now you can have a fractional co-founder who's an expert in AI. hire me to embed w/ your team, find where AI creates real leverage, and ship it. not in months, in weeks. 22 years. 80 products. millions in sales. initialcommit.co
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Doug Breaker retweeted
To stay in business, you don’t need to beat your competitors, you need to beat your costs.
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claude code is like a straight A recent computer science grad who just slammed 6 red bulls, a twelver of brews, and lost their short term memory.
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Personal/biz update - I quit the CEO-for-hire game and bought a company to run - Shoeboxed.com. Full story here - linkedin.com/posts/dougbreak… and here - shoeboxed.com/blog/sba-loan-…, including SBA breakdown of how I put 5% down. Many thanks to @SBA_Matthias for the SBA help.

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Doug Breaker retweeted
The real flex isn't making $1M a year. It's making $1M a year without: - Checking email before noon - Missing family dinners - Working weekends That's the real flex.
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Doug Breaker retweeted
CONGRATULATIONS to Tory Beitler from FC United — your 🏆 U13 MVP! 🏆
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Doug Breaker retweeted
The ‘12 #FCUGA side are @GAcademyLeague National Champions! They defeated CUP in Norco, CA 1-0 in the final! #WinTheDay #ChicagoFCU ⭐️⭐️⭐️⭐️
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Doug Breaker retweeted
Startup idea: America, but no daylight savings time.
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Doug Breaker retweeted
this youtuber with 9m subs saw his wife struggle to find a quality wheelchair — $5k price tags, long waits, made in china so he built his own factory in the USA now, he sells these $1,000 custom wheelchairs, shipped in weeks we need more creator-led businesses like this.
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Doug Breaker retweeted
some of you have never had to integrate with authorize.⁠net and it shows.
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