I believe that at the end of the solopreneur rainbow lies a handful of generational, category-defining companies waiting to be born. Let me explain.
Solopreneurs
There's been quite a bit of buzz about the rise of the one-person business, aka the solopreneur. Stripe recently published an article called "The Age of the Solopreneur,"[1] citing a few interesting trends:
- Solopreneurship is growing faster than employer-business formation
- Those solopreneurs are reaching meaningful scale – more than twice as many solopreneurs earned over $1 million in 2025 as in 2023, while nearly three times as many crossed $5 million and $10 million.
This is very exciting to me, as my own roots and earliest exposure to building useful tech came from a solopreneur journey. In college, I started and ran a men's barbershop business called Chuck's Cuts, doing all the things needed, beyond just the haircutting itself, to turn it into a steady stream of college-spending money.
I truly believe humans have a fundamental drive to bring ideas into the real world, and it's very inspiring to see the solopreneur wave as a sign that technology is allowing people to pursue that, even as a team of just one.
But there's another interesting thing about the solopreneur wave: the products they use are a leading indicator for the next generational products and companies.
The Solopreneur as a Benchmark for Value
Solopreneur-indispensability on a product is the clearest test that a product truly moves the needle for a business.
If a product enables one person to operate a competitive business, particularly in a market where teams of 10, 50, or 100 people compete, we may be onto something generational.
A solopreneur, by definition, cannot fill gaps in a product with employees, internal process, or operations. The product has to work. And when it works, its value is so obvious that the sole owner, unencumbered by stakeholder debates or internal ROI discussions, can conclude: "My business could not run without this."
This isn't to say every company is meant to be a one-person company. Certain businesses require specialized expertise, human judgment, physical labor, or simply enough work that adding more people makes sense. Nor should every product sell to solopreneurs first — there are massive problems elsewhere to solve as well.
But this framework gives us a nice bar for defining the value of enterprise software: would a solopreneur find this mission critical?
Leading Indicator for Generational Products
Beyond using solopreneur value as a benchmark, what's more exciting is that it can be used as a leading indicator of the next generational companies.
Conventionally, building for solopreneurs (SMB-style GTM, PLG) and building for enterprise (top-down sales) are treated as different products with different requirements and different ceilings. I don't think that split holds for the rare, truly generational company.
The solution that lifts the solopreneur is the one best positioned to win the enterprise.
Coding Agents
There is a lot we can learn from coding agent products, which are still light-years ahead of almost every other software category in disruption and value creation.
Coding agents reached a perfect inflection point, where it became possible to create a one-person software company. Different products pursued different interfaces, GTM motions, positioning, distribution strategies, and use cases, and those decisions produced different growth curves and competitive dynamics.
But fundamentally, the combination of interface and intelligence moved the needle required to go from idea to feature, then from idea to product, and made the one-person builder possible.
As soon as the first solopreneur built a product end to end by themselves, the writing was on the wall: the category had fully arrived, and the best within it were poised to be generational.
What to Look For
I'm looking for PMF where:
- A team of one can compete in a market where existing companies employ teams of 10, 50, or 100.
- The business owner literally could not operate the business without the product or service.
The initial wedge may look small, and traction is unlikely to explode overnight. Early traction almost necessarily requires an existing market and incremental value, and by definition the solopreneur market is bottlenecked by the rate of new solopreneur business creation.
But if done right, these products reach a bar of indisputable value, and product utility (the right combo of interface and intelligence) that sets up the perfect two-direction squeeze of the market:
- From the bottom up, the product scales alongside a new generation of AI-native businesses as they grow from one person into larger companies.
- From the top down, the same capability enters existing enterprises, driving greater productivity, broader individual ownership, and lower coordination and headcount requirements.
Is This You?
The big questions will be what are the angles and shapes of the solution!
- Who is the team that can convince the next generation of solopreneurs to bet on their product? A team that owns the solopreneurs' success as their own, closely entrenched and able to win their trust.
- Which categories of solopreneurs will companies start with? Some of these are farther along, more mature and well-served, such as e-commerce and software businesses. Some potentially interesting ones to edge into are brick-and-mortar stores, the experience economy, and local community and events.
- What use cases have software needs that are clear and feasible to solve from the start? Back office, customer management / engagement / outreach, and physical AI.
These are all open questions, but I'm excited to meet and partner with founders who see the world similarly and are working through these questions themselves.
- Stripe Economics, "The Age of the Solopreneur" ↑