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!

CA
Joined September 2020
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
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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
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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
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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!
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real example. last night first time in a long time i can remember waking up thinking about work middle of night. not easy fall back asleep. grind on!
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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
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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
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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 🇺🇸
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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!
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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
You're out of your mind if you're still doing an MBA in 2026. • Six figures in tuition • Two years out of the workforce • Taught by professors who've barely run a business I don’t understand how there are still people who think this is a good idea.
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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]
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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…
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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
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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..
Entrepreneurship = firefighting. Every day you wake up, there’s a new problem to solve. A new fire to put out. You have to fall in love with the process of solving these problems. If you don’t like doing this work, you shouldn’t start a company.
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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
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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
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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-…
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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!
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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
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