Yahya Mokhtarzada found a $40 charge on his credit card for in flight wifi. He had not been on a plane that month. When he looked back through the statement, he had been paying it for 14 months. He checked whether his bank or Mint would surface other charges like it and found that neither did.

He mentioned it to his brother Idris, who happened to be working with a new banking API called Plaid for a different idea. They pulled their own transactions into a spreadsheet, wrote a small algorithm to find anything that repeated, and sent it to friends and family. About half the people who tried it found a subscription they had forgotten about. That was the signal.

The first version shipped under a different name. The founders' own launch post, dated 20 November 2015, introduces BillNinja.com and tells the origin story in the first person: "an unknown charge of $39.99 on my credit card" that had been running for 14 months, "A total of $559.86". Within weeks the product had been renamed Truebill and the three brothers, Yahya, Idris and Haroon, were in Y Combinator. Yahya's own post from 22 January 2016 describes being "about 3 weeks into the Winter 2016 batch" and calls the program a flat sprint to demo day.

The public launch came on 17 February 2016 with a Show HN post that picked up over a hundred points. The thread was almost entirely people asking one question: if you can read my bank data and the product is free, how do you make money? One commenter said Truebill had just found him $6,000 he had been overbilled, then asked the money question too. Yahya answered him directly: "right now we actually don't make money."

That stayed true for a long time. In a written interview six months later, in August 2016, he was still describing the app as a free service and the plan as recommendations, "a few early monetization partnerships" of the people who like Netflix also like Spotify kind. The company raised from Y Combinator, Social Capital and others, hired engineers in San Francisco and the Washington area, and kept giving away the part users valued most.

The turn came when the money ran low. In his own account: "For the first two years, we did not have a premium model. All the revenue was through affiliations and partnerships. We were struggling and adding premium was a last-ditch effort." Charging a subscription for an app whose selling point was cancelling subscriptions looks absurd on paper, which is roughly why it went untested for so long. They shipped it because there was not much else left to try. They launched on a Friday, and by Sunday the conversion rate was "3.5 times what I expected".

That is the anchor for the milestone on this page. The founders' first public post dates the start to 20 November 2015, and Yahya's own framing is two years free before premium, which puts the first paying members around late 2017, roughly 730 days in. The opening price was a few dollars a month, deliberately small, to find out whether anyone would open their wallet at all.

The second experiment mattered as much as the first. Truebill replaced the fixed price with a request to pay what you think is fair, and members picked their own monthly amount inside a band that later ran from $3 to $12. It sounds like a way to lose money and it did the opposite. It lined the company up with the mission it was selling, and it removed the pressure to pack the product with upsells to hit a number.

After that the growth compounded. Truebill raised $15 million in October 2019 and a Series C in November 2020, both of which Yahya posted about himself. In September 2021 the company blog announced "One MILLION premium members" and quoted him saying the demand showed how much work was still ahead. On 20 December 2021 Rocket Companies agreed to buy the company for "1.275 billion in cash", with the press release describing Truebill as on track to generate $100 million in annual recurring revenue and 2021 revenue more than double 2020.

Haroon's note to members the same day set out the arc: "Six years ago, my siblings and I started Truebill from my brother's basement", and the company had "grown our team from 3 to 159". Yahya posted his own version, proud of the people he had spent "the last 6 years" alongside.

Two things are worth holding in mind before reading this as a template. The brothers had already built and sold Webs.com, so they were not starting cold, and they went on to raise $85 million by Yahya's own count. And the product was free to consumers for two full years, which only works when someone else funds the gap. What does carry over is the shape of the decision. They spent two years assuming their users would never pay for a service whose whole point was stopping payments, they were wrong, and the only reason they found out is that they finally shipped the test when they had almost run out of room to be careful.