Boring Business Thesis

The unglamorous business as the better bet

The thesis holds that a dull, cash-generating business in a proven market is often a safer and more lucrative bet than a glamorous technology narrative. Kevin O'Leary states the preference plainly across a portfolio he describes as spanning insecticide, dry cleaning, sandwiches, cremation services, commercial kitchens, and pet care: "I like those better."¹ His reasoning rests on a base rate. By his account eight of ten venture deals burn to zero, and most consumer apps fail not on product but on customer acquisition, which he summarizes as "99% of apps fail because they can't acquire customers no matter how good the app is."¹ A boring business, by contrast, arrives with an existing market, stable acquisition costs, and real free cash flow.

The scaling curve and the freedom number

O'Leary attaches an empirical model of startup difficulty to the thesis. The zero-to-one-million stage is the hardest, where roughly eighty percent of startups fail; one to five million is hard; five to fifty million he calls "pretty easy"; and fifty to five hundred million is, in his words, "not so hard at all," reasoning that "by the time you got to five, you've proven you have executional skills and you can hire people and you can build a strategy."¹ The payoff of a cash-flow business, in his framing, is that saved and reinvested profit builds toward the freedom number, the reserve that makes an operator financially independent, whereas venture equity stays illiquid for years. He also treats free national attention, such as a Shark Tank appearance, as the hidden lever that lets a boring product acquire early customers at near-zero cost and convert them to repeat buyers, against a comparable tech product spending as much as forty percent of revenue on paid acquisition.¹

Boring as unglamorous, not as slow

Eric Glyman uses the same word approvingly but from a different angle. For him a boring business is an unglamorous category rather than a small or bootstrapped one. He argues that "there's an entire class of tools that tend to be great business models, and some of the fastest-growing companies of the last few years have been exactly that."² The shape he describes is software that takes the operational paper cuts of running a company, cards, expense, accounting, payroll, and abstracts them away so an owner does not have to think about them. His examples include Ramp, Rippling, valued at roughly seventeen billion dollars in its last funding round at the time, and HubSpot, which are venture-funded and fast-scaling rather than anti-venture.²

Two differences are worth holding as a tension rather than merging. On the capital model, O'Leary's boring businesses are deliberately anti-venture, favoring cash flow over equity, while Glyman's are among the highest-velocity venture companies in the market. On where the defensibility sits, O'Leary points to unit economics and a repeat-purchase brand, while Glyman points partly to opacity: the business model is illegible from outside, and that illegibility is itself part of the moat. The shared core both operators endorse is that a dull-sounding business solving a real, recurring pain can beat a glamorous story.

Where the thesis is contestable

The thesis is a preference expressed by two operators, not a proven law, and it carries obvious limits. O'Leary's scaling curve is drawn from his own portfolio and treats the five-to-fifty-million stage as easy in a way many founders would dispute. His enthusiasm for boring categories coexists with his own aggressive bets on distribution and brand, which suggests the edge may lie less in the category than in the operator's discipline. Glyman's version quietly redefines the key term, so that "boring" no longer means low-growth at all, which makes the two claims harder to test against each other than the shared vocabulary implies. The thesis is best read as a corrective to narrative-driven investing rather than a formula, and it sits close to O'Leary's related view that most VC-backed success still refuses the liquidity a cash-flow business provides.