From: myfirstmillionpod
Kevin Ryan, a prominent figure in the tech and media industries, is known for his ability to launch and scale multiple successful companies. Contrary to conventional wisdom about focus, Ryan has a track record of initiating numerous ventures annually, including eight in one year [00:00:09]. His approach centers on identifying significant market problems and building strong teams to address them [00:19:12].
DoubleClick: Pioneering Ad Technology
Kevin Ryan served as the President and CEO of DoubleClick, a pivotal ad technology company [00:39:42] [00:00:42]. He joined the company in 1996 as employee number 20, initially as CFO, then President, and finally CEO [00:41:40] [00:03:30]. Under his leadership, DoubleClick grew rapidly from 10 to 2,000 employees across 25 countries [00:03:37]. This aggressive international expansion occurred even before their first country was profitable [00:10:11]. This strategy allowed them to dominate the ad technology market by providing a global presence that competitors lacked [00:10:28].
Despite the dot-com collapse, which led to a 70% client bankruptcy rate and a reduction to 1,000 employees [00:03:49], DoubleClick maintained significant market share [00:03:54]. The company was acquired by Google for approximately $3 billion in 2007 [00:03:26]. This early market penetration by DoubleClick is cited as a reason why Google still holds a commanding share in ad technology [00:10:44].
AlleyCorp and the Launch of Business Insider
Following the sale of DoubleClick, Kevin Ryan and his partner Dwight launched what they called AlleyCorp, an incubator model focused on developing new companies [00:05:27]. Their strategy involved identifying one to three good ideas annually, finding strong teams, and providing an initial investment of 500,000 from each partner) [00:05:34] [00:06:15].
Business Insider’s Foundational Insights
Business Insider, launched in 2007, emerged from a simple observation: existing business publications like The Wall Street Journal and Business Week did not update their websites throughout the day [00:11:54]. Ryan, a compulsive reader of business and media publications, identified a need for continuous updates, especially with the advent of mobile phones in 2008 [00:12:15].
Key strategies for Business Insider included:
- Continuous Updates: Publishing stories throughout the day, often starting with rumors and updating as more information became available [00:12:28].
- Opinionated Viewpoint: Providing a “smart point of view” on events, even if not perfectly accurate in the long term [00:12:57].
- SEO and A/B Testing: Meticulously optimizing for search results and A/B testing headlines to maximize traffic [00:13:06].
- Lean Start: Beginning with five journalists covering the whole world [00:14:40].
Initially, critics dismissed Business Insider as “low quality” or “junk” [00:14:08]. However, the company surpassed The Wall Street Journal in traffic within approximately five years [00:14:15]. Business Insider, now reaching 300 million unique visitors monthly, achieved this growth without spending any money on advertising [00:13:29].
Henry Blodget, a perceptive journalist with a background at Merrill Lynch who had faced scrutiny on Wall Street [00:15:17], was chosen as CEO. His fresh perspective, free from traditional newsroom constraints, was a strength [00:16:34]. The company was eventually sold for 11 times revenue [00:55:50].
“There were many many people that religiously read Business Insider every single day so it just had a brand that I think was much stronger and more defined” [00:17:36]
MongoDB: Database Innovation
MongoDB, another of Ryan’s ventures, was founded in 2007 with Dwight and Elliot Horowitz [00:22:10]. The initial product, ShopWiki (a shopping search engine), was sold in 2007 [00:22:34]. The insight behind MongoDB was the belief that Oracle was not the correct database solution for the future, particularly with the shift from structured to unstructured data (like videos) [00:25:08]. They envisioned an open-source database structured for this new data landscape, inspired by the success of Linux [00:25:52].
The early years of MongoDB were challenging, with three years of zero revenue [00:22:55]. Funding was difficult, especially during the 2009-2010 financial climate [00:23:07]. However, the internal confidence was buoyed by growing utilization of their free product globally, with 50,000 small companies and hundreds of meetups [00:24:00]. Sequoia eventually invested, allowing the company to raise significant capital [00:23:13].
MongoDB has since grown to a 2 billion and $300 million in annual profits [00:06:57]. Ryan notes that the company made its founders very wealthy [00:23:25].
Ryan’s Business Philosophy
Kevin Ryan’s success stems from a consistent business model and strategy:
Identifying Opportunities
Ryan and his team dedicate significant time to research, with individuals spending two and a half months interviewing up to 50 people to understand pain points and opportunities in an industry [00:19:27]. They aim to find “big obvious problems” that are not overly complicated or nuanced [00:35:32]. This often involves looking for “one-chart businesses” where a single data point clearly indicates a major opportunity, such as the rising cost of labor driving the need for automation [00:36:43].
“If you have a good idea and if you’re hiring a salesperson who costs 150,000 and they’re selling 500,000 worth you need to hire those people all day long because you have an opportunity.” [00:07:41]
Ryan is always thinking about where the world will be in 10 years, focusing on long-term trends rather than immediate opportunities [00:28:09]. His current areas of interest include:
- Healthcare [00:29:33]
- Semiconductors and Material Science [00:29:38]
- Developer Tools and Enterprise Software [00:29:08]
- B2B Marketplaces (e.g., maritime industry procurement) [00:29:55]
- Social Impact [00:29:12]
- Robotics and Automation [00:28:19]
- Psychedelics/Mental Health [00:20:28]
Scaling Through Investment and Teams
Ryan’s model emphasizes growth through strategic investment rather than bootstrapping. He believes that if an idea is strong enough to turn one dollar into two, entrepreneurs should “get as much money as you can and back that truck up into that machine and dump it in there” [00:08:09]. This includes being willing to lose money initially by hiring aggressively and investing in growth [00:07:25].
The AlleyCorp model leverages a robust infrastructure, including 70 in-house engineers and a 10-person executive search firm to recruit top talent [00:27:37]. Ryan’s role is primarily as a Chairman, guiding companies and solving high-level problems, rather than being the day-to-day CEO [00:41:40]. He maintains a supportive relationship with his CEOs, offering strategic advice and introductions [00:47:54].
Morning Brew is mentioned as a successful acquisition by Axel Springer, which also acquired Business Insider [00:56:01].
Personal Approach
Ryan maintains a low-key public profile, avoiding social media to focus on “thinking time and managing time” [00:48:58]. He primarily invests his own money in his ventures, operating what is historically a single LP (Limited Partner) fund [00:53:08]. He also holds a significant amount of cash for liquidity [00:58:07]. His portfolio includes real estate, such as a commercial building in New York City being developed as AlleyCorp headquarters [00:57:15].
Regarding AI, Ryan believes its immediate use will be more “mundane,” optimizing customer support and coding efficiency [00:43:48]. His team is actively encouraged to explore and implement AI, with a full week dedicated to learning about the technology [00:44:07].