Fourth in a series designed to show creatives opportunities with clients that are good for people and the planet
Guilded. Freelancers Union. A+ for intent. But you’re too slow.
72 million of us need your help now.
“I can’t get a car loan,” she said.
“Lost my job, lost my healthcare,” said another.
“I’m freelance but nothing’s free about it. A desperate chasing of one gig after another. I’ve got two degrees, my parents had none, and I still can’t save for retirement.”
I’m hearing this stuff every day from clients who are contract and freelance. 1099ers all. They have no support.
Most of the ingredients already exist to support us 72 million 1099ers. A shockingly large number. Something like 40% of our workforce — a number that’s only going to grow, especially with AI.
Six organizations. Each providing part of the solution. Together, they could go a long way toward providing a support system for us 1099ers. Best of all, all six would grow and prosper in the process. I’m not talking about a handout.
They’re just not connected.
Guilded Freelancer Cooperative — a worker-owned cooperative. Still small, still early, built specifically to manage freelance contracts, payroll, and tax compliance. They already partner with Freelancers Union.
Freelancers Union — 500,000 independent workers strong. Group-rate health, dental, vision, disability, and life insurance built for the self-employed. A 401(k) plan built for people without an employer to sponsor one. Tax help and contract templates. Real political advocacy.
Credit unions — 144.7 million members, roughly 22,000 branches, chartered by law to serve members instead of shareholders. An 18% legal rate cap, against 25-29% at the megabanks. They’re bigger than Chase and Bank of America combined.
YMCAs — 20 million people served, 2,600 branches. Childcare, fitness, community space, decades of trust already built into buildings.
Public libraries — 155 million people served, 17,000 locations. The single largest, most evenly distributed physical footprint on this list, and the only one completely free to walk into, no membership required.
Kaiser Permanente — 12.9 million people served across 8 states. A real nonprofit, actually built for healthcare, not shareholder return.
There is a problem none of them can solve alone: 1099 workers aren’t a “group” in the way insurance and lending were built to recognize.
Group health coverage needs an employer of record. Group lending terms need a stable income history. Scattered freelancers look like risk to systems built around a W-2. That’s why Kaiser can’t offer group rates to freelancers, and why most credit unions underwrite as if a stable paycheck is all that counts.
That’s the gap Guilded and Freelancers Union can close. Guilded’s model — the same one Smart.coop has run in the EU since 1998, now serving over 100,000 freelancers across nine countries — turns freelancers into something that functions, legally and administratively, like a group. Freelancers Union already negotiates group-rate insurance for hundreds of thousands of members on exactly that logic.
So the system isn’t six separate orgs. It’s two layers: Guilded and Freelancers Union aggregating 1099 workers into a recognized group, and credit unions, Kaiser, YMCAs, and libraries — already built to serve groups — doing what they already know how to do the moment one exists. A credit union extends real lending terms, cash-flow underwriting instead of a W-2 review. Kaiser offers real group coverage instead of the volatile individual marketplace. The Y and the library become daily infrastructure — coworking next to childcare, free wifi and meeting rooms — serving a known population instead of guessing.
None of these six needs to invent something from nothing. Two real, proven mechanisms already exist to make the connection work.
The first is the hiring hall. In the 1950s, in my old Beacon Hill neighborhood in Seattle, men who worked casual labor belonged to a union and hung out at the hall when they didn’t have work. Calls came in, jobs got announced to the room, workers volunteered, a few got picked. No algorithm ranked anyone. No app took a cut.
Building trades and longshore unions still run versions of this. Guilded or Freelancers Union could run a modern one — library branches or Y locations as the physical hall, an actual dispatch system a member organization runs, not a platform’s.
The second is the trust fund. What if any company that hired a 1099 worker paid a small percentage of the fee to a central holder — Guilded, say — and that became a real, pooled retirement and benefit fund?
That’s not a new idea. It’s a Taft-Hartley trust, running since 1947. About 1,400 of these multi-employer funds already cover 10 to 11 million workers in construction, trucking, and entertainment, industries where nobody stays with one employer long enough for a normal pension. Employers contribute per hour or per job. The fund is jointly trusteed and follows the worker across every employer that contributes. A freelancer today loses their retirement the moment a gig ends. A Taft-Hartley-style trust, with Guilded or Freelancers Union as trustee, wouldn’t.
Not a simple switch to flip. It legally requires a collective bargaining agreement, an organizing fight, not a technical one. And neither mechanism reaches everything: no unemployment insurance for a dry month, no legal protections only government can grant. But getting the work fairly, and keeping something for later, are both solvable with tools proven for eighty years, just never pointed at us.
That’s the whole system. Not a merger. Not a new mega-institution. Six organizations, already doing good work separately, plus two proven mechanisms nobody’s bothered to point at the 1099 economy yet.
Feel this, Guilded and FU…
I checked into the library as usual. Fall is happening. Leaves falling, a bit of a chill. The librarian was new, in her twenties but happy to check me in with an encouraging nod. Said she’d just graduated Western and was looking.
Just as I was about to settle, a text hit my phone. Guy in Mexico City wanted an hour with me. And a notice flashed letting me know he’d paid. My healthcare and retirement had been topped up.
An imaginary moment. Not an impossible one.
A+ for intent isn’t enough anymore.
72 million of us are still waiting.
~
The Work Beneath the Work is available now at tedleonhardt.com/the-work-beneath-the-work
