Contra.com: Maxing Out Credit Cards and Domain Financing Loans Before Raising a Dollar
When Sahil Lavingia, founder of Gumroad, tweeted "Buy a .com domain name. Go into debt if you have to," Ben Huffman quote-tweeted it with his own story:
"yep, we bought contra.com before we raised any $$, had to max out a few cc's and take a domain financing loan + spend my life savings."
Someone replied: "didn't know domain financing loan was a thing"
Ben's response: "Yeah highly unregulated"
The Pre-Funding Domain Purchase
Most startups wait to buy their perfect domain. They launch on a .io or .co, raise funding, then upgrade to the .com when they can afford it.
Ben Huffman did the opposite.
Before raising a single dollar for Contra, he went all-in on Contra.com:
- Maxed out multiple credit cards
- Took a domain financing loan (an unregulated lending market most people don't know exists)
- Spent his life savings
The domain purchase wasn't funded by investors. It was funded by personal debt and every dollar Ben had.
Domain Financing Loans
When Ben mentioned taking a "domain financing loan," many people were surprised to learn such a thing existed.
Domain financing is a niche lending market where lenders offer payment plans for premium domains. It operates in a gray area—as Ben noted, it's "highly unregulated."
These loans typically:
- Charge higher interest rates than traditional loans
- Require down payments (often 10-30%)
- Use the domain itself as collateral
- Operate outside traditional banking regulations
For founders without access to capital but desperate for the right domain, it's one of the few options available.
The Contra Vision
Contra is a commission-free freelance platform that's been described as a cross between LinkedIn and Shopify for independent workers. The name "Contra" suggests going against the grain—which is exactly what the platform does by charging zero commissions.
For a brand built on being different, the domain mattered. Contra.com was short, memorable, and owned the brand. A compromise domain like GetContra.com or Contra.io would have undermined the positioning.
Ben believed in the vision enough to bet his financial future on it—before anyone else believed in it enough to invest.
"It Aged Me"
When someone congratulated Ben on the purchase, calling it an "epic purchase," his response was simple: "Thanks Dann, it aged me."
The stress of maxing out credit cards, taking an unregulated loan, and spending every dollar you have to buy a domain—before you've raised any money, before you've proven product-market fit, before you know if the business will succeed—is not a decision most founders would make.
But it's the decision Ben made.
The Bet
Contra has since raised significant funding and grown into a platform serving thousands of freelancers. The domain purchase, however risky at the time, positioned the company from day one with the exact-match .com that matched their brand ambition.
Could Contra have succeeded without Contra.com? Possibly. But the domain gave them immediate credibility, brand clarity, and the kind of positioning that signals "we're serious about this" from the first day.
Ben's willingness to go into personal debt for the domain wasn't reckless—it was a bet that the domain was foundational infrastructure, not a nice-to-have.
The Debt-Funded Domain Playbook
Ben's story is extreme, but it illustrates a truth about premium domains: sometimes the perfect domain is available before you can afford it.
When that happens, you have three choices:
- Wait until you raise funding (and risk losing the domain)
- Compromise on a different domain
- Go into debt to secure it now
Ben chose option 3. He maxed out credit cards, took an unregulated domain financing loan, and spent his life savings.
It aged him. But Contra.com became the foundation on which he built a company that eventually attracted the funding to justify the risk.
Not every founder should follow this playbook. But for Ben, betting everything on the domain before betting anything else worked.
Sometimes you have to buy the domain. Even if you have to go into debt to do it.