Steve Jobs, great founders and the discipline of doing a few things incredibly
Key points
Key takeaways from Source interview with Steven Rosenblatt, co-founder and general partner of Oceans Ventures, on How I Invest with David (October 2026):
Ambition versus delusion. Ambitious founders are deep in detail — they take you along their journey, articulate clearly where the company is and where it is going, and may be wrong but are never muddled; delusional founders are long on storytelling and smoke, short on substance, and that gap usually separates success from failure.
Talent is the universal ingredient. Across more than 20 years of building and investing, Rosenblatt says the number one thing great tech companies share is the ability to attract world-class people — smart people want to build extraordinary, game-changing things, so the founder's mission itself is the talent magnet.
Why, not what. He looks for why a founder is building — an insight deep in their veins, evidenced by the work they did before starting — rather than motivation by a gold rush or status; the strongest pitches carry concrete detail and a long personal track record.
The Ashton Kutcher test. Rosenblatt endorses the angel investor's rule: if you would quit whatever you are doing to go work for the founder, that is the standard that justifies investing — though he cautions it is one dimension among several.
Pivots and adaptability. Great companies are often pivots, and a founder's ability to process new information and change direction matters as much as their original vision — the greatest weakness is getting stuck in what you are building.
Watching Steve Jobs work. Through Apple's ~$300M acquisition of Quattro Wireless in 2009, Rosenblatt watched Jobs combine obsessive attention to detail — down to pixels and colours for iAd — with an overarching grand vision, a rare cocktail he now looks for in founders.
Three hours in Steve's conference room. Jobs tested cultural fit and trustworthiness rather than the product, firing three hours of questions punctuated by long, silent pauses to assess whether Quattro could teach Apple the advertising business; Apple at the time ran one P&L with one ultimate decision maker.
Why acquisitions die. Most deals fail from organisational rejection; Quattro succeeded because Andy Miller reported directly to Jobs, the team kept full access and resources, and iAd — now Apple Ads — grew into a multi-billion-dollar services business.
Complementary personalities. Jobs surrounded himself with operators who balanced his intensity — Tim Cook's operational rigour, Eddy Cue's dealmaking — because too much of one extreme drives people into the ground, a lesson about self-awareness Rosenblatt sees in the best founders.
Few things done incredibly. The defining Apple cultural lesson is doing a few things incredibly well rather than many things mediocre — hard to emulate, but the standard he holds companies to.
Read more: How I Invest with David (YouTube)
