
CEO @Systemsixbooks. Relentlessly fixing finance departments for SMBs. Acquired via ETA in 2021. BHAG=$50M rev by 2030. Ex PE/MBA. Golf when I can. Girl dad!
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Joined September 2020
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Reading Rockefeller's biography
Interesting line last night:
"When it came to mergers, he didn't fight for the last dollar and tried to conclude matters cordially"
One of the most intense business people of all time understood still having a good relationship with folks on the other side of the table is mission critical
Because, once the deal is done, the real works starts. And you need the help of the other person on the other side of the table
This isn't a zero sum game in SMB M&A
Nothing like seeing peers and friends throw wins on the board (pumped for them) to fire me up to push harder
That's one of the things I LOVE about being in SMB space
If you FEEL like you aren't far enough along, moving fast enough
Chances are you can just fire more energy into the biz
And you can move the needle
QUICKLY
Corporate / large cap PE etc...so hard for something like effort (which is so controllable) to truly drive outcomes
I love how in smaller businesses....input does more closely equal output
Always have loved to grind. Always will
It's cheesy, so of course they put it on Gameday
Freeman (amazing coach) @NDFootball talking about how everything you want is on the other side of hard
But it rings so true. That's a life statement.
And in the era of everyone thinking you can just buy a passive biz, people need to hear that more in SMB
5.5 years in, it's still hard. It's a different hard, you grow, your goals become different, but nothing is easy
Especially when you are playing w personally guaranteed DEBT that likely is way beyond your ability to cure it if things go bad (i.e. you will go bankrupt)
Remember this
If you're afraid of hard
If you're not willing to work intensely (albeit for yourself on your schedule)
RUN don't walk away from SMB acquisitions
I work just as hard if not harder than I did in bulge bracket PE
I may or may not make back most of the $ I could have earned (not over a career, large PE always wins there)
But I have control and autonomy
But it damn sure is not passive
We are lucky to be on a great ride at @systemsixbooks
But I increasingly feel its critical for real owners to share real stories...not slop about $500T AI rollup
We are trending towards epic 2026. 🤞pending latest acq will finish $11M rev, healthy ebitda
Yet i feel more stress than I have in years.
The job changes as you scale. You are able to do less. More about the people you hire and the direction you set
Ship gets harder to turn
More people, more customers, more opp for issues
Wouldn't have it any other way
Super proud of who we are, what we've done, and where we're going ($50M rev by 2030)
But point is, yall, this ain't buy, roll up, and go meditate for 12 hours in your ai ice bath!
Recently relegated my iPad to my basement office
Grab it when I need it, but it’s been weeks
Drastically reduced screen time
How are others combating these days ?
Feels like a never ending fight
Grew up in dc. Evacuated on 9/11 and several times after (anthrax, etc)
This day always matters
I always spend time today going down YouTube rabbit holes
Videos of just insane heroism
Everyday people
That’s what I remember most
How we responded
And I know today, if the same thing happened, were the same America
We would respond the same
They changed our country
Created division
But ultimately, I don’t think you can break the true American spirit
Grit and a willingness to help your neighbor
9/11 showed that
And I know deep down we are still that
Remember that
Those who died want us to live that way
Together
OK this biz adoption of military lingo has to stop
I saw a title today on LI - "Forward Deployed Investor"
What's next - your we-work suite is a Forward Operating Base/FOB?
Wartime CEO b/c OpenAI rolled out a new model?
What we do is not war
Let's have some respect
Especially top of mind this week 🇺🇸
Industry selection, how much debt you use, your background, etc, all matter
Impacts how you get out of the starting block
But then, success in SMB...it's simple. But insanely hard.
Just people
Can you hire right, incentivize, keep
All the above impact ability to do it
But it all comes down to ppl at end of day
Don't forget it!
Recently got asked this advice
I think if you’re a true true entrepreneur, you don’t need one. You’ll hustle your way to the network and inspiration you might get at MBA
This was not me
But for a lot of folks, myself included, MBA (I’d say top 10-20?) it is so helpful
Opens your eyes to other paths
Shows you they are possible
Helps you get started
Do you learn a ton in the classroom. No
But that’s the same everywhere. Football players learn the most on the field
MBA won’t guarantee success
But it can help you start on paths otherwise you would never ind
Ok there’s gotta be a rollup play here
Also…this is amazing/ hilarious
I too one day hope to self list an island I don’t use
I am selling my island in Lake Tanganyika, Tanzania. Gorgeous place, but we don’t use it enough. $7.9 million or best offer. Anyone interested should contact me directly at [email protected]
I'm 35
Knew he was young, but didn't hit me truly that Marcus Freeman became HC at @NDFootball at 35 until I was reading this
Crazy to think about being in that position right now
Talk about levels. Insanely impressive
Nothing wrong with some good humble pie to start your Friday
#choosehard
nytimes.com/athletic/7522210…
Well this got some unexpected run!
Bunch of new followers. Quick intro
Husband and girl dad 1st
Fortunate to own and lead @systemsixbooks. Acquired it 5 years ago, 4x rev since, mainly organic, plus some more M&A
Made so many mistakes, love trying to apply them moving forward
Today, we serve over 400 $1-$100M rev biz with high touch finance (bookkeeping, payroll, bill pay, controller, cfo) and tax services
65 team members across 25 states and 3 countries
Many of our new clients just bought their business. Self funded searchers, independent sponsors, traditional searchers, long term holding companies, PE firms etc
Our mission is to empower and elevate remote professionals. We know if we deliver a kick a#^ work environment, we'll deliver kick a*& work
Moving forward, we'll continue growing organically and via M&A
All in service of our mission - to empower and elevate remote professionals. To be the best place to work in remote professional services.
Our BHAG is to be a $50M rev biz by 2030. We'll get there by continuing to win at what we do, but also expand via acquisition into HR consulting, wealth management, and other professional services
Feel incredibly lucky to have been taught about power of attitude by mentors and heroes. Try to channel that everyday
Golf on the side when I have time
Reading Rockefeller's biography
Interesting line last night:
"When it came to mergers, he didn't fight for the last dollar and tried to conclude matters cordially"
One of the most intense business people of all time understood still having a good relationship with folks on the other side of the table is mission critical
Because, once the deal is done, the real works starts. And you need the help of the other person on the other side of the table
This isn't a zero sum game in SMB M&A
Yes, but also, you must decide what fires to LET BURN
This has been an adjustment for me, too. Want to fix everything, improve everything. Growth mindset everywhere
But you can only do so much. Certainly only do so much well
So, know which fires are eating at the foundation..
This one is pretty interesting personally
We have several clients rolling up aspects of youth sports
They will make a ton of $. We are making good $ on it too. And they're generally doing good work. Adding tech, improving experience. Charging for it
But I get this is making something that used to be so much more universal so much harder
Will be interesting to see how it impacts American competitiveness on a global level overtime. Take baseball. As that becomes way more travel oriented, $$, will USA become less competitive at WBC as more kids are left out even if they have the talent
And then you think personally. Am I really going to NOT spend the $ on our daughter if she wants to do something? Travel volleyball (she has 2 very tall parents...)
I might academically not do it, but no way I'm telling her "hey we can't play that league because I'm not a huge fan of the proliferation of rollups into youth sports"
Very curious to see how this all plays out. It's really not that different than institutional ownership of HVAC, SFR, etc, but I think because it is kids, getting a lot more run
‘Travel sports,’ a term that has come to encompass all sorts of private teams, leagues, and clubs, used to be for the truly exceptional young athlete. Now, they’re for anyone willing to pay — an expensive, exhausting commitment that has become popular not necessarily because millions of parents want them for their children but because it can feel like there’s no other choice. Rec programs are underfunded and struggle to compete with for-profit leagues for prime field, rink, and court times. And the level of play is diluted, often very early, as travel teams are incentivized to enroll children at young ages.
Around 5 million children in the U.S. now compete on travel teams. Parents find themselves trapped. They know the benefits of sports and want that for their children, yet giving it to them often means buying into a sports ecosystem that’s inherently flawed. As the pay-to-play model increasingly takes hold, so does the idea that kids should start competing at younger and younger ages, risking their sense of self along with their shoulders and ACLs.
“I never want my kids to look back and say I didn’t do everything I could to help them live their dreams,” a mother of three soccer players said. She’s hired professional photographers to take action shots for her 12- and 13-year-olds’ Instagram accounts — the platform has become a recruiting tool — and they’ve both asked her to pay for personal trainers.
“I think the word isn’t ‘specialize’; you are ‘professionalizing’ your kid early. You are exposing them to everything professionals have to deal with — I’m talking injury, time, schedule, everything,” said John Van Benschoten, a former MLB player and travel-baseball coach.
It makes one ask: All this for what? And for whom? Read Caitlin Moscatello’s cover story on how travel leagues have made youth sports more expensive, hypercompetitive, and all-consuming — and the investors who are making a killing: nymag.visitlink.me/1-gbZQ
One of the best things I’ve done in awhile for me is moving to taking no basically meetings on Monday
Helps the weekend so much bc I know I have so much space on Monday to GSD
I still work some every weekend but takes mental pressure off big time
Highest HC cost increase for companies in 20 years
"Passive income" they said 🤡
We are staring down a 18% INCREASE right now after ~5% last couple years
Let's just say that was NOT in the budget
Biz buyers...add this to underwriting...
We'll be fine
Others will not
wsj.com/health/healthcare/u-…
Took an L yesterday
One of those ones where you fill that pit in your stomach
Not fun, and in SMB, any L ultimately is on you. This one especially was on me!
Good kick in the pants to be better today and moving forward
That's the upside of SMB. Agency to change. Immediately
Onwards!
Pumped - another year, another accolade for @systemsixbooks
We're up ~2x in 3 years and heading towards $10M rev by the end of 2026
Not without plenty of mistakes, failures. And plenty of 7a debt
But we have MOMENTUM.
My main takeaways
1. Buy in a growing industry
2. Buy a good business
3. Treat your people well
You won't grow it alone. You need excellent people alongside the journey who feel fulfilled and supported
None of this is possible without the team we have at System Six. So thank you to them
Here's to doubling again, and continuing to do it the right way - with team at the forefront of everything we do






