How to Spot 10-Year Trends and Build Billion-Dollar Companies — Kevin Ryan of DoubleClick, MongoDB, Business Insider, and Many More (#884)

Kevin Ryan is one of the leading entrepreneurs and investors in New York. Often called the “Godfather of NYC tech,” he is the founder and CEO of AlleyCorp, a New York based venture capital firm that incubates and invests across healthcare, AI and software, consumer tech, deep tech, and more. Kevin is also the co-founder of several notable companies including MongoDB, Business Insider, Zola, Gilt Groupe, and Transcend Therapeutics. Earlier in his career, Kevin was the CEO of DoubleClick, which he helped grow from a 20-person startup to a publicly-traded company with more than 1,500 employees.

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Transcripts

Show Notes

Connect with Kevin Ryan and AlleyCorp

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Timestamps

• [00:00:00] Start.
• [00:01:25] The chronology, prepared by the robots.
• [00:03:40] 20 trends on a whiteboard, 10 years out.
• [00:06:33] Four conferences, a China trip, and how to seat 30 people.
• [00:11:42] The YouTube Kevin didn’t start.
• [00:17:47] Gilt: $500 million in year four, then a falling knife.
• [00:22:06] “We’re going to wait for the next internet.”
• [00:25:58] DoubleClick: 25 countries before one was profitable.
• [00:27:52] The AlleyCorp model: $500K each, a year to build, then raise.
• [00:32:26] Recruiting Henry Blodget in 30 minutes.
• [00:38:28] The two-week business crush.
• [00:41:44] Valar Atomics: $20 million to $6 billion in three years.
• [00:45:25] Why the fund stays small: 2% vs. 20%.
• [00:47:15] Ping pong, red wine, and Ibiza dance floors.
• [00:49:05] Three things only; everything else cut 80%.
• [00:51:52] The book that changed Kevin’s mind at 54.
• [00:54:20] Methylone: MDMA’s gentler, shorter cousin.
• [00:56:54] The second mouse gets the cheese.
• [00:59:57] A public benefit corp that actually pays out.
• [01:05:46] Is early-stage venture dead?
• [01:08:04] Robot massage and the AI agent that switched to Spanish.
• [01:11:35] The healthcare Shopify that failed; MongoDB’s revenue-free years.
• [01:15:06] Kevin’s billboard.
• [01:16:19] Pulling levers: taxes, training, and immigrants.
• [01:20:04] New York is booming.
• [01:21:41] Parting thoughts.

Quotes from Kevin Ryan

“I went to the parent company and I said, ‘This internet thing’s going to be big and we have a head start, so why don’t you give me … a couple million dollars and I’ll build up an internet division. We can do it for other companies.’ The disturbing thing is the guy I was talking to … said, “No, because we’re going to wait for the next internet.” First of all, I know you don’t know what you’re talking about. There is no next internet.”

— Kevin Ryan

“It’s important to start narrow.”

— Kevin Ryan

“It’s better to do one thing really well than a bad job on everything.”

— Kevin Ryan

“I never think about exits. We need to focus on the product. Do we have a product that everyone wants to use? If you solve that, everything else follows.”

— Kevin Ryan

“There’s a saying that “The early [bird] gets the [worm]. But the second mouse gets the cheese.”

— Kevin Ryan

“There are 164 soft drinks. The odds of you coming up with one that stands out is pretty slim. Whereas the changes that are occurring or have occurred in solar or wind or geothermal or nuclear, there are going to be billions and billions and billions of dollars of contracts signed to produce energy. Robotics, same thing.

— Kevin Ryan

Want to hear another episode with someone who builds category-defining companies and bets on where technology is headed? Listen to my conversation with Netscape co-creator and Andreessen Horowitz co-founder Marc Andreessen, in which we discussed his rules for investing, how he decides whether a company should stay the course or pivot, why his firm bets for change when others bet against it, the factors behind a big investment, the future of AI and drones, bitcoin, “strong opinions loosely held,” his debate with Peter Thiel, and much more.

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