Welcome to Upper Market

The most durable businesses sell what people can't choose not to need.

Play the game long enough and you’ll realise that most of the “new, fun, sexy” businesses that come on the market or sell for high multiples are due to get rolled.

Not too long ago REA AI App was released. An AI Powered App that can reverse engineer any software product through reading code and giving you the end state software solution businesses already use - or quite frankly need.

The moat around Software Businesses has just been destroyed.

And I personally love the fact that I own businesses that provide solutions in the physical world.

What's ahead in this Newsletter:

  • Raising Capital - What to Communicate

  • This Week's Deal

  • Last Week's Deal

Raising Capital: What to Communicate

Last week I broke the news to you that you’re going to have to put your mug online.

Well if it’s not your mug, at least your name.

Not having any presence online in the year 2026 will unfortunately create too much mystery about you. So much so, that it’s just suspicious.

So if you need something what do you need?

We’ve started with the domain - something as close to as possible as your name.

Why don’t we start with - what you actually want to achieve?

I’ve created a full course on How to Buy a Business. It’s a free course and even my book Speedrunning Capitalism covers an important piece to the puzzle.

It’s what you want to build. Your thesis, your game plan - and what you’re trying to achieve.

As much as I wish there was a secret to it - there isn’t.

If you want to raise money, to buy businesses - you better have some kind of idea as to what you want to buy. How you want to create wealth. How you plan on protecting the downside.

That’s the sauce.

The more your idea develops on your search path, you can revisit your website and update it.

After you’ve put your face, some works and something similar to a coherent explanation of who you are on the internet - you’ve broken your online profile virginity in a way you might not have imagined you would break it.

And that gives you permission to keep doing it and improving it.

All you’re doing, is letting the world know you exist, articulating the game you want to play, and sharing your thoughts as they develop.

Next week, I’ll walk you through the process I would walk through to keep updating this online.

This Week's Deal: Vehicle Compliance Testing Station

Over $350,000 of owner earnings, revenue above a million for three straight years at 75% gross margins, 900-plus fleet vehicles coming back on a schedule, and a government authorisation a competitor simply cannot buy. Asking $1,200,000 including $300,000 of equipment. A boring, essential, regulated little machine, where the real asset is a licence that's hard to earn and even harder to replicate.

This is a long-established South Auckland vehicle testing station with an integrated mechanical workshop, authorised by NZTA to issue Warrant of Fitness and Certificate of Fitness inspections. Every light vehicle on the road is legally required to be tested, so the demand is non-negotiable, and the business splits its revenue roughly evenly between that compliance testing and the mechanical repairs that naturally follow. The homework is how secure and transferable the NZTA authorisation is, and who actually does the work.

It has operated for more than fifteen years from modern, purpose-built premises on a high-traffic main road, holds NZTA authorisation for WOF and COF A inspections on light vehicles, and reports normalised SDE over $350,000 on revenue above $1 million in each of the last three years at gross margins around 75%. Revenue is split roughly 50/50 between compliance testing and mechanical repairs, it services around 30 vehicles a day, and it carries a strong recurring commercial base of taxi, rental and fleet operators covering 900-plus vehicles alongside daily walk-in and rideshare trade. The $1,200,000 price includes over $300,000 of equipment and tools, the site has four hoists and two inspection pits with room for three more, and there's no management software in place, which the seller frames as an efficiency opportunity.

What I'd Want to Understand:

First is the NZTA authorisation, because it is the moat. The listing's strongest line is that the authorisation can't be bought, only earned, which is exactly what makes this business defensible: a new competitor can't simply open up across the road. So I'd want to understand precisely how that authorisation works and transfers, is it attached to the business, the premises, or a specific certifying person? What are the ongoing compliance and audit obligations to keep it, and what's the risk it could be suspended or lapse? A regulatory moat is wonderful, but only if it comes with the business and stays intact after I own it.

Second is who does the work, since the earnings are owner-operator. SDE is a working-owner number, so I'd map exactly what the owner does: are they a qualified inspector, a mechanic, the manager, or all three? How many staff are there, are the inspectors and technicians staying, and what would it cost to replace the owner's role? The business also holds Accredited Employer status for migrant staff, which is useful but also a dependency, so I'd confirm the team is stable and that the certifying capability doesn't walk out with the seller.

Third is the quality of the two revenue halves. The roughly 50/50 split between testing and repairs is really two businesses with different characters: compliance testing is the sticky, non-discretionary, every-vehicle-must-do-it annuity, while mechanical repairs are more competitive and discretionary. So I'd want the margin and trend of each, and I'd lean hardest on the testing side and the 900-plus-vehicle fleet base, understanding how concentrated that fleet revenue is across a few big taxi, rental or rideshare accounts, and how reliably those vehicles come back.

Fourth is the equipment, the lease and the upside. With $300,000 of equipment in the price, I'd age the hoists, brake machinery, alignment and diagnostic gear and understand the replacement capex ahead, and I'd confirm the new lease terms on the high-traffic site, since location is part of the walk-in trade. The "no management software" point cuts both ways, it's a genuine efficiency opportunity, but it also means the current numbers were produced without it, so I'd treat software-driven gains as upside to earn, not value to pay for today.

Growth Angle: The clearest levers are capacity and efficiency: there's room for three more hoists on a site already pulling 30 vehicles a day, so a buyer can add throughput without moving, and introducing management software to a business that runs without any should lift utilisation and margin from the same footprint. Beyond that, deepening the fleet, rental and rideshare relationships grows the recurring testing base, and for an existing workshop owner, bolting on a hard-to-get WOF/COF authorisation is a genuine strategic prize. Essential demand plus spare capacity is a clean growth story.

The Drawbacks: The earnings are owner-operator SDE, so a hands-off buyer must pay for the roles the owner fills, and the business depends on an authorisation and on certifying staff that must both transfer and stay. Half the revenue is more competitive repair work, there's real equipment capex behind the $300,000 of gear, and migrant-staffing arrangements carry their own policy risk. It's a durable, essential business, but its value rests on a licence and a team you have to confirm you're actually getting.

Final Thought: A fifteen-year, NZTA-authorised testing station throwing off $350,000-plus on non-negotiable, recession-proof demand, with a 900-vehicle fleet base and spare capacity to grow, is exactly the kind of boring, essential business that quietly outperforms the exciting ones. Whether it's worth $1.2m comes down to the licence and the people: confirm the authorisation transfers cleanly and stays intact, secure the certifying staff, and price the repair half and the equipment honestly. Get those right and you've bought a regulated annuity with a queue at the door. Miss them, and you've paid for a licence that might not come with the keys.

If you want more details on any of these businesses or would like an introduction to the sellers, just reply to this email.

Last Week's Deal: Finance-Automation SaaS

$273,000 of EBITDA, gross margins above 90%, no employees, no premises, and a product that automates something every business has to do. Asking $860,000. A pure little software business of the kind that's almost all leverage, where the whole question is how sticky those subscribers really are, and who keeps the code alive.

This is a software-as-a-service business that automates a core finance function businesses rely on, earning recurring subscription revenue from loyal business customers who, the seller says, stay once they're on board. It runs with no staff and no premises, from anywhere, at software margins a physical business can't touch. The homework is the two things that make or break any SaaS purchase: the real churn behind "they stay," and who maintains and develops the product once the current owners leave.

The product automates a core finance function and is sold on recurring subscriptions to business subscribers, generating $273,000 of EBITDA on gross margins above 90%, with no employees and no premises so it can be run from anywhere. The owners describe the product, integrations and customer base as already in place and say customers stay once on board, and they're looking to hand over, with a full handover included, to a buyer with the resources to scale it. At $860,000 that's roughly 3.1 times EBITDA, which is modest for genuinely recurring, high-margin software, if the recurring part holds up.

What I'd Want to Understand:

First is the churn, because for SaaS it's everything. "Once customers are on board, they stay" is the entire thesis, so I'd want it proven in numbers rather than words: monthly and annual churn over several years, by customer and by dollar, how long the average subscriber lasts, and what the subscriber base looked like three years ago versus today. Software automating a core finance function should be deeply sticky, because ripping it out is painful, so I'd expect low churn and I'd want to see it, because low churn is what makes 90% margins compound and high churn is what quietly turns them into a treadmill.

Second is who keeps the software alive, given there are no employees. "No employees" is the attraction and the risk in one phrase: if nobody is on the team, the product is almost certainly maintained by an owner who is also the developer. So I'd need to know exactly who built it, who maintains and secures it now, how documented and transferable the codebase is, and what it would cost to hire the technical capability the business currently gets for free from its founder. For a non-technical buyer this is the whole deal; for a technical buyer it's the opportunity, but either way I'd confirm the product won't stall the day the current owner stops answering the phone.

Third is what it's built on, and what it plugs into. A finance-automation tool almost always integrates with other systems, accounting packages, banks, payment platforms, so I'd map those dependencies: if the product relies on a third party's API or sits on top of one accounting platform, then that platform's decisions, pricing or competing feature can affect the whole business. I'd also want the technology stack's health, whether it's modern and maintainable or ageing and fragile, because with software you're buying the engine, not just the subscriber list.

Fourth is why it hasn't scaled, and the customer concentration. The owners want a buyer "with the resources to scale it," which is honest, and also a flag: I'd want to know what's actually held growth back, a product that needs work, no sales effort, a niche smaller than it looks, or a founder who simply never pushed. And I'd check how concentrated the revenue is across subscribers, because a high-margin recurring business leaning on a few large accounts is far riskier than the same revenue spread across many small, sticky ones.

Growth Angle: The appeal is that the expensive, slow work is done, the product exists, the integrations work, and customers are paying and staying, so the opportunity is pure leverage: add subscribers to a product that costs almost nothing to serve the next one, and nearly all of that new revenue drops to the bottom line at 90%-plus margins. A buyer with a real sales and marketing engine, exactly the "resources to scale" the owners mention, could grow this far faster than two hands-off owners have, and the no-staff, run-from-anywhere model means scaling doesn't drag a mountain of cost behind it.

The Drawbacks: The entire value rests on recurring revenue that must be proven genuinely sticky, and on a product that, with no employees, almost certainly depends on the founder's technical knowledge, a real risk for a non-technical buyer. It's a single product in a single niche, potentially exposed to the platforms it integrates with and to a larger competitor, and the "needs someone to scale it" framing means the growth is promise, not proof. It's a lovely shape, but a lot of it has to be verified in the churn data and the codebase.

Final Thought: A recurring, 90%-plus-margin SaaS automating something every business needs, with no staff and no premises, at roughly 3x EBITDA, is close to the purest form of leverage you can buy, an income that scales without the weight. Whether it's worth $860,000 comes down to two confirmations: that the churn is genuinely low and the revenue truly recurs, and that the product can be maintained and grown without the founder's head. Prove the stickiness and secure the technical capability, and this is a superb, scalable asset at a fair price. Fail to, and you've bought a codebase you can't maintain and a subscriber list that was freer to leave than you thought.

If you want more details on any of these businesses or would like an introduction to the sellers, just reply to this email.