How I Invest with David Weisburd · Oct 9, 2026 · 1h 4m · 44m saved
With Steven Rosenblatt, Co-Founder and General Partner at Oceans
Apple's new mobile ad business booked $60 million of advertising in six weeks in 2010, before the product existed outside a sales deck, Steven Rosenblatt said.
Most of mobile advertising then was small banner ads, and agencies balked at a $1 million order. Steve Jobs saw the first $1 million deals and asked for $10 million ones instead.
"Fast forward, we did four $10,000,000 deals. We did $60,000,000 in six weeks." — Steven Rosenblatt
Steven Rosenblatt, Co-Founder and General Partner at Oceans, on How I Invest with David Weisburd, ran sales at Quattro Wireless when Apple bought it in 2009, spent three hours being questioned by Jobs before the deal closed, and later became president of Foursquare. Oceans is a seed-stage venture firm in New York and an investor in the AI chip company Etched.
The full interview is covered here so you can skip it. 64 minutes of audio, 20 minutes of reading.
Here are the 17 lessons that matter.
Key Takeaways
Jobs spent three hours testing whether the Quattro team could teach Apple advertising, not judging the product
Apple sold $60 million of iAd advertising in six weeks on a product that was not yet live
Jobs reviewed the brands' ad creative himself, every week, for six to eight weeks
Most acquisitions fail when the bought company is parked under someone who doesn't know why it was bought, Rosenblatt said
Quattro's co-founder reported directly to Jobs the whole time
Great founders hire people whose personalities offset their own, as Tim Cook and Eddy Cue did for Jobs
Ambitious founders are deep in detail; delusional ones are long on storytelling and short on substance
Oceans broke two of its own rules, no hardware and no Series A, to back Etched
AI does not change what to look for in a founder, but speed, capital and the threat to every software company are new
Rosenblatt expects some AI companies to lose billions and multiple new trillion-dollar companies to emerge
A founder-friendly New York took about 20 years to build, and he expects several trillion-dollar companies to start there in the next ten
1. People Come First
The host asked what great technology companies have in common. Rosenblatt said it starts with people, and it starts with the founder.
The best companies attract the best talent
"And without question, the number one universal thing through all the different periods is people and talent." — Steven Rosenblatt
Capital matters because people have to be paid, he said, but smart people want hard problems. A company doing the same thing as 15 others will not draw them.
"So it's got to be a challenge. It's got to be something that you feel like you're helping and part of building." — Steven Rosenblatt
"It's not just the founder's company. It's everyone's company." — Steven Rosenblatt
He joined a mobile startup as the financial crisis hit
He joined Quattro Wireless in 2008 because of its founders, whom he named as Andy, Eswar and Lars, and their complementary skills. His wife was six months pregnant at the time.
"In two thousand seven, eight, it was far from obvious." — Steven Rosenblatt
He said many people told him he was "nuts" to join a company building for a small screen when phones still had keyboards and Apple was just rolling out its first iPhone.
