Anthony
Mironov

A paycheck is a luxury most of the workforce no longer gets

For the W-2 employee, payday is a quiet miracle. Money lands. Taxes are already gone. Health insurance renews itself. None of it requires a single decision. Anthony Mironov spent his career around that machinery, then stepped outside it, became a 1099 contractor in late 2016, and discovered the machine simply stops at the edge of traditional employment.

What replaces it is admin. Invoicing. Chasing the contract. Tracking which client paid and which forgot. Setting aside the tax that nobody withholds for you. Buying the insurance, hiring the CPA, reconciling the year. Mironov has described contractors stitching together five to seven separate apps just to approximate what one paycheck does on autopilot. He calls it reverse-engineering a paycheck, and he means it literally.

Wingspan, the company he co-founded with Greg Franczyk in 2019, exists to delete that work. It is payroll and benefits infrastructure built from scratch for people who get paid on a 1099 - the freelancers, the gig workers, the independent professionals who, by Wingspan's count, now make up one in three American workers, up from roughly one in ten in 2005.

The shape of the bet

The market Mironov is chasing is not a niche. An estimated 74 million people in the United States get paid as contractors, and the dollars moving through that channel run to roughly 4% of GDP. His argument is that payroll itself is migrating - the old W-2 market, he says, is "disintegrating and shifting to 1099s" - and that almost nobody has built the rails for where it is going.

Build it like Shopify, not like ADP

The reason existing payroll giants cannot simply bolt on a contractor feature is structural. ADP, Rippling and the rest are built around a one-to-one relationship: one employer, one employee, priced per head. A contractor breaks that model. They are a business, not a hire. They juggle many clients at once. They manage their own benefits. The plumbing has to handle many-to-many, which is why Mironov reaches for a different analogy.

A payroll platform for contractors, he argues, needs to look more like Shopify - a network sitting between many sellers and many buyers - than like a traditional payroll system designed around a single boss. Roughly a third of the contractors on Wingspan get paid by more than one company on the platform, and each of those overlaps makes the network a little stickier and the next onboarding a little faster.

From Fortress to freelancer to founder

Mironov did not arrive at contractor payroll by accident, but he did arrive by detour. He studied economics at Cornell, graduating in 2010, then spent a decade in and around private equity and investment - names like Fortress Investment Group, Clarion Capital Partners, Thayer Street Partners and Balance Advisors. Much of that work sat close to payroll and benefits for small businesses, which is to say close to the exact machine he would later notice was missing for everyone outside it.

The turn came in 2016, when he went independent and felt the gap personally. After talking to thousands of contractors who described the same frustrations, he and Franczyk started Wingspan in 2019. An early direct-to-consumer version taught them the contractor side cold; they then flipped to selling B2B, to the companies with hundreds of contractors who felt the pain most acutely.

• 2010
  Graduates Cornell University, BA in Economics.
• 2010s
  A decade in private equity and investment - Fortress, Clarion Capital, Thayer Street, Balance Advisors.
• 2016
  Goes freelance and runs head-first into invoicing, contracts, insurance and tax chaos.
• 2019
  Co-founds Wingspan in New York with Greg Franczyk.
• 2022
  Raises a $14M Series A led by Andreessen Horowitz.
• 2023
  Crosses $1B in payments processed; team grows from ~20 to 40+.
• 2025
  Raises a $24M Series B led by Touring Capital; launches Wingspan Embed; passes $3B processed.

Three years, compounding

The July 2025 Series B was a marker as much as a milestone. Alongside the $24 million from Touring Capital - with Andreessen Horowitz, Long Journey Ventures, Distributed Ventures, Company Ventures and 186 Ventures along for the round - Wingspan launched Embed, a white-label version of its product that any HR or payroll platform can drop in to pay contractors directly. It is the picks-and-shovels move: instead of fighting for every customer, sell the infrastructure to the platforms that already have them.

It is a tidy summary of how he thinks. Less interested in the contractor population a company has today, more interested in the inflection point ahead - the moment when two or three contractors quietly become fifty, and the spreadsheet finally gives out.

The contractor's universe

Ask Mironov why this is hard and he keeps returning to the same idea: contractors are not a variation on employees, they are a different species of worker entirely. "Contractors operate in a different universe," he says - one with multiple client relationships, self-managed benefits and no employer quietly handling the back office. Treat them like employees with a different tax form and you will build the wrong product.

That conviction is why he is comfortable saying no. No to the employer-of-record business. No to becoming a generic payroll company. The whole pitch rests on knowing one customer better than anyone else does, and the discipline shows up in the language: "We're the contractor specialists." It is both a positioning statement and a fence.

Where the AI actually earns its keep

For all the talk of frontier models, the AI inside Wingspan is aimed at the least glamorous corners of the back office - which is precisely Mironov's point. Onboarding that used to take days now runs in minutes. Insurance certificates arrive in a dozen inconsistent formats; the system reads and verifies them. More than half of support cases - around 54% by the company's account - get resolved instantly, and payment reconciliation and compliance monitoring hum along underneath. The value is not a clever demo. It is hours that contractors and finance teams never have to spend again.

Mironov also frames AI as a tailwind on the demand side, not just the cost side. The rise of specialized, on-demand work - including the wave of contract roles spun up around AI labs themselves - pushes more people onto 1099s, and more dollars through exactly the channel Wingspan was built to carry. The technology that threatens some incumbents, in his telling, widens his market.

Proof in the unglamorous wins

The case studies Mironov points to are not flashy logos so much as recovered time. Teladoc Health, he has noted, saves roughly 28 hours a month on payment processing by running contractors through Wingspan. PEOs like Insperity were watching customers churn when contractors got paid outside their platforms through Bill.com or QuickBooks - so Wingspan Embed lets those platforms offer native contractor management without building it themselves. It is a quietly clever wedge: solve the leak for the platform, and you become indispensable to it.

That is the throughline of the whole company. Mironov is not selling a vision of the future of work in the abstract. He is selling the absence of a specific, grinding annoyance - the missing invoice, the unverified certificate, the contractor who is paid late because someone, somewhere, was reconciling a spreadsheet. He felt that annoyance himself in 2016, and he has spent the years since turning it into infrastructure that, when it works, you never have to think about at all. The best paycheck, after all, is the one you forget is happening.