Building the Ladder Behind Us

There aren't many Afghans in the startup and VC world. Even fewer that were founders and sold their company for over $1 billion. I had dinner with them last week.

Their parents fled Afghanistan after the Soviet invasion. They raised four sons who built a company out of a dorm room. That first company was Webs.com. They sold it to Vistaprint for $117.5 million. Most founders would take that exit and disappear. They came back and built Truebill, raised from Accel, Bessemer, and Y Combinator, and Rocket Companies acquired it for $1.275 billion. The second exit was more than 10x the first.

Here are the lessons from their journey that they have shared with me.

The personal finance space was a graveyard. Every investor said the category was dead. They built anyway and now own 65% market share. Haroon said it plainly: the difference between winners and losers is never the idea. It's always the execution.

They treated everything as CAC to LTV. Not just marketing. Hiring, product features, geographic expansion. If you put in a dollar and get more than a dollar back, that's a cash machine. The discipline was holding efficiency while scaling spend, not spending less. They built their second company on the mistakes of their first. Everything they did wrong at Webs.com, they never repeated. Everything that moved the needle, they doubled down on. Zero to a billion dollar exit in six years. That would not have been possible without the hard lessons from company one.

They launched with what Haroon calls a minimum lovable product. Not minimum viable. Lovable. The first version just showed you your subscriptions. That was enough to validate the problem was acute and get people telling their friends.

Haroon was against charging a subscription for an app that cancels subscriptions. His team ran the test without his permission. The metrics were so strong he tripled down the next day. Your intuition might be right 80% of the time, but when the data comes in on the other 20%, shift immediately.

On selling: don't consider it real until the CEO is personally involved. Always have more than one offer. Never throw out the first price, because whatever number you say becomes your ceiling.

The part that stuck with me most was about working with his brothers. Your co-founders won't leave when things get hard. They're not going to Google when the company hits a rough patch. And when you exit, the money stays in the family. You haven't left anyone behind.

There are so many kids around the world who look like us and would trade their lives for ours in a heartbeat. We have tremendous privilege. We achieved our versions of the American dream. And that comes with a responsibility. Not to prove ourselves. To build the ladder behind us.

Originally posted on LinkedIn.