One Man LBO

Former investment banker.
10Y at value hedge fund.
Set out to acquire, now building instead.

[One Man LBO @OneManLBO]

Today marks the end of an era for me, as I exit public market investing after a 10+ year run at my hedge fund. My last day as a W-2 draws to a close. This is it.

I'm stepping off "the path", out into the unknown. The professional linearity of the track so many aspire to -- Ivy League degree, investment banking, buy-side stint, single family house in a nice suburb -- is broken. Purposefully.

All to take a bet on myself.

This moment has been in the making for some time. In my own head, I've lived this reality for so long that now that the moment is actually here, it feels eerily quiet. Almost like a non-event. Not so for some neighbors, friends, and family -- reactions range from positive curiosity to sheer shock.

I think life is best lived in seasons or chapters. It was time for a new one. And sometimes, to start a new chapter, it takes a decisive act of violent agency. You quit a great job, you sell a beautiful house, and you move a couple thousand miles. To a lot of people, that doesn't make any sense.

But we want this for our family. We want to be out West, and we want to call our own shots, create our own autonomous luck in this life. That's all that matters. It's a simple matter of long-term priorities, with confusing short-term optics for now, and I'm OK with that.

I've heard the full range of feedback on Search over the last few years. The hype, the success stories, the horror stories, the "don't do it, no good listings, brokers suck, this is the top" warnings.

At the end of the day, I think reality is a spectrum, and the experience needs to be uniquely lived. I need to go out, encounter my own unique truth, take a few (OK, very likely a thousand) punches to the face, and hopefully create the best conditions for luck, to the extent any control can be exerted over this at all. The market is what it is. I need to find my own answer.

The worst outcome isn't failing to locate and close on a decent asset. It's the nagging questions at the end of this life. "What could have been, had I seriously tried, gone all out and applied myself to the best of my ability, made the most of my God-given talents?"

Only one way to find out. Here we go.

[One Man LBO @OneManLBO]

@vrexec Idaho. The answer is always Idaho. But you knew that.

[One Man LBO @OneManLBO]

@MicroRollupSMB @blueprintsmb22 Bro you gotta share your story on here at some point! Would love to know niche / post synergy multiples paid, or maybe not if you don’t want to invite competition into your space (though execution ability will always be the barrier)

[One Man LBO @OneManLBO]

I think the most useful way to think about this is the out-of-pocket cost in the event of a high-cost incident (ER visit, hospitalization). So it's mostly a question about deductibles.

The ACA plans have atrocious deductibles ($7K+?), so they essentially leave you a cash payer from the start. You pay enormous premiums for the privilege of having coverage kick in at very high dollar levels.

The HSA accounts only work if you take a high-deductible plan.

The conclusion we reached was that with little kids, we're going to land in the ER probably once every 1-2 years, and I'd rather have a $500 self-participation per event with CrowdHealth than thousands of dollars of first-dollar liability.

[One Man LBO @OneManLBO]

@wshaw_9 We looked at COBRA, too, it was an immediate no due to rate ($2K monthly premium for entire family)

[One Man LBO @OneManLBO]

Will, very happy with CrowdHealth. On it for 5 months now and great experience. They have covered health events for us without issues. See below for original writeup.

If you end up signing up and want a discount for first 3 months, you can use referral code ONEMANLBO (I get a referral bonus from them for that, full transparency)

[One Man LBO @OneManLBO]

In 2026, our family of four is ditching traditional healthcare insurance and covering most of our medical needs for $600 / month. Here’s how we’re doing it.

For anyone self-employed and / or looking for coverage options more affordable than traditional ACA exchange insurance, here are my notes from just having done a deep dive into this over the last couple of weeks.

Note that A) none of this is medical advice, B) this may NOT fit your family’s personal needs given this is NOT health insurance, and C) you may face additional complications and penalties if you’re located in the handful of states that impose an individual health insurance mandate. We happen to be in a state that has no such mandate.

For next year, we have decided to do a combination of @JoinCrowdHealth and Direct Primary Care (DPC), which should cover basic healthcare needs for our family of four for an all-in cost of less than $600 / month.

What is CrowdHealth?

It’s not health insurance, but a community of members that crowdfunds higher-cost health events (ER visit, surgeries, etc.), which you submit with a self-participation amount of $500. So as an example, if you have to go to the ER and end up with $2,500 worth of bills, you submit this amount to “the crowd”, and if it gets funded, you pay $500, and the community pays $2,000.

Funding is not guaranteed and since this is not health insurance, you have no regulatory recourse, but the historical track record looked good enough to me to get comfortable with this risk (something like 99%+ of claims submitted for funding did get funded).

My main concern here were extreme high-cost events like cancer. I tried to actively locate stories of funding denial, but ended up coming across mostly positive anecdotes. The company features several case studies of funded health events (including cancer) on their Twitter page, and overall anecdotal feedback from Twitter friends was also positive, including one that got ER events funded.

CrowdHealth reduces cost of care through two primary means:
1) focusing on non-obese, non-smoking members, with very limited coverage for pre-existing and chronic conditions (so their risk pool is quite healthy on average, much healthier than for ACA plans), and
2) aggressively negotiating down medical bills with hospitals and other medical providers, which treat you as a self-pay / cash pay patient and therefore are not bound by insurance negotiated rates.

What is Direct Primary Care?

Think about this as basic-medical-care-as-a-service. You pay a primary care physician practice a fixed monthly subscription fee per month, and in exchange you can come in for virtually unlimited appointments and basic services (some of these practices include lab test coverage, others charge you very low wholesale pricing they have negotiated with third-party labs).

Often these primary care doctors will also provide pediatrics, basic dermatology, and women’s health services. The basic idea is that your family physician should be able to cover 95%+ of your routine (non-acute) healthcare needs in-house, without having to refer you to an army of specialists, and to prevent higher-cost urgent care and ER visit episodes unless absolutely necessary.

In our area, we can enroll our family at a DPC provider for $200 / month. That is a really good deal, considering that I estimate that a single doctor visit billed through traditional insurance would likely run us $100-$200 (going straight to deductible), even after discounts.

How can DPC care be so cheap? It's mainly because most of these DPC providers don't work with insurance plans at all. They get paid direct cash subscription fees by their members. So they have radically lower and simpler overhead (less billing, coding, and collection admin), and the doctors can spend more time with patients and focus on medical care provision rather than dealing with insurance headaches.

Putting CrowdHealth + DPC together

CrowdHealth charges a family of four a $240 / month basic administrative fee ($60 per member), and then the monthly contribution towards other members’ medical expenses is a maximum of $420, but has run closer to $255 / month actual for most of 2025 (you only pay for actual expenses that the risk pool incurs every month).

However, if you and your spouse agree to submit a couple of lab tests showing that you are in good health (test costs also partially reimbursable by CH), you can get a discount of 10%-20% on this monthly contribution. So in theory, if you secure a 20% discount on the $255 / month medical contribution, you end up closer to ~$200. Add in the $240 admin fee and your monthly all-in CrowdHealth bill could be as low ~$450 / month.

But it gets better.

CrowdHealth allows you to submit up to $300 per member per year for “wellness expenses”, which could be an annual physical, dental, or, importantly, DPC membership fees.

So if a family of four is in theory eligible for up to $1,200 / year ($100 / month) reimbursement, then if you submit your DPC membership costs for funding, the effective cost drops from $200 to as low as $100 / month. For the entire family.

So now you have
1) $450 / month for CrowdHealth (for catastrophic / high cost events), plus
2) $100 net cost / month for virtually unlimited basic DPC services from your primary care physician practice.

$550 / month all-in for a family of four. That’s pretty good. Any stuff not covered by the DPC (labs, specialist visits, higher acuity outpatient procedures etc.) would obviously come on top of this.

Again, this is just one man’s opinion and decision. This is not health insurance. This requires a leap of faith and some risk tolerance. Do your own diligence, choose your own path. Do what’s right for YOUR family (which I can't tell you).

I’m just posting this in case it’s helpful to some folks, knowing about one option that I was completely unaware of up until a couple of weeks ago.

[One Man LBO @OneManLBO]

@Sam_Rosati @JackieHirsch_ Exactly

[One Man LBO @OneManLBO]

When @Sam_Rosati officially changes guidance and recommends proprietary deal sourcing from day 1 (in conjunction with brokered deals), you listen up

Also, great anecdata from @JackieHirsch_ on deal interest in this market

150 NDAs within 24 hours? INSANITY

(Hearing similar numbers from intermediary contacts here in... IDAHO, not even close to a tier 1 coastal market)

If you think brokers have time for relationship building in the heat of a live deal, you are sorely mistaken. They're just trying to survive and triage.

So proactive relationship building is once again key across both brokered and proprietary sourcing. Highly speculative, highly long-term oriented.

So freaking challenging to make friends and plant seeds. How do you even know how to allocate your limited time anymore?

Which brings me back to one of my core tenets: you need a thesis in this market, whether it's geography or industry focused (I had both last year), so you can even start to understand where you should be making friends and build relationships.

This small business buying game is shifting further and further away from the actual transaction. You need to be so early now. It's almost VC-like in terms of speculating which broker or owner may have a good deal down the road and getting ahead of it, WAY further up in the funnel.

Sourcing timelines are extending, and I know several good and talented people who are in year 3 of searching now.

WELCOME TO ULTRA HARD MODE

[One Man LBO @OneManLBO]

@SMBDistribution YES!

[One Man LBO @OneManLBO]

@Prithvi_Jadwani @Sam_Rosati @JackieHirsch_ AI slop slop slop

[One Man LBO @OneManLBO]

@wraithbrokerage @Sam_Rosati @JackieHirsch_ Dammmnnnnn

[One Man LBO @OneManLBO]

@SMBfugazzi @Sam_Rosati @JackieHirsch_ You should post some war stories about how prop search has changed over time! Tons of good stuff I’m sure

[One Man LBO @OneManLBO]

@sourcesandmuses @rob_smb @Sam_Rosati @JackieHirsch_ This would make for such a great Wedding Crashers movie about two guys converting in order to buy a small business

[One Man LBO @OneManLBO]

@RobKufel @blueprintsmb22 He doesn’t like either thought, and I understand

[One Man LBO @OneManLBO]

@sourcesandmuses @Sam_Rosati @JackieHirsch_ 100%. Everything is moving towards old fashioned door knocking, which doesn’t scale but can’t be faked

[One Man LBO @OneManLBO]

@JackieHirsch_ @Sam_Rosati Yeah, I can see why 😂
Not so under the radar anymore

[One Man LBO @OneManLBO]

@signulll You must not have heard of the long only world

[One Man LBO @OneManLBO]

@sourcesandmuses Inzo Technologies advertises on AM pod (led by searcher I believe) but no idea how good they are

[One Man LBO @OneManLBO]

@reallyoptimized Yup. Just did this with family (IAD -> FRA -> HAM). It’s easy as long as the US passports are signed, or German customs fill fine you up to 5,000 Euros or some crazy amount.

[One Man LBO @OneManLBO]

@damcurious @FrontierBDesign Very welcoming and warm. Has been nothing but a good experience

[One Man LBO @OneManLBO]

I’m 38. I’ve moved a lot. Lived on 3 continents growing up (US, Europe, South America). It’s been enormously valuable.

I’ve been part chameleon, part lone wolf.

I’ve often struggled with the concept of “home”.

Growing up, part of me envied the kids who were firmly rooted and had strong, multi-generational networks in their home towns. Part of me took pride in being a detached outsider. A protective veneer of superiority.

I’ve had to recreate networks from scratch every time I moved. I’ve built confidence and adaptability. You end up with this dispersed global network of a few select friends you keep in touch with from every distinct chapter in your life.

When I met my wife, I realized she was the same way (pilot family, Continental Airlines). You keep moving, but your core family and values are tight. She “gets it”.

We are now finally moving into a stage of our lives where we think that Boise is our final home. You never know, but my gut tells me this is it. And that’s special. We’ve seen a lot and empirically solved the equation.

But I wouldn’t have gotten to the destination without the journey. That’s the irony.

My kids will be the same. They will leave home, live overseas, live in NYC for a few years. Then find the place that’s right for them.

And the cycle repeats.