How to Spot 10-Year Trends and Build Billion-Dollar Companies — Kevin Ryan
In a Nutshell
Kevin Ryan built AlleyCorp by systematically identifying 10-year trends, then acting as co-founder to launch companies like Gilt Groupe, Business Insider, and MongoDB. His process involves listing persistent trends (gig economy, value-based care, nuclear power, psychedelics), validating them over years rather than months, and focusing on product-market fit before raising capital. The model emphasizes controlled scale—$335M across three funds with 50%+ IRR—while maintaining a small team and prioritizing founder involvement over asset growth.
These notes were generated by AI and may contain inaccuracies.
Kevin Ryan graduated from Yale in 1985 with a degree in economics. He began his career at Prudential Investment Corporation, working in New York and London. In 1990, he earned an MBA from INSEAD in France. After working at Euro Disney and United Media, he returned to the United States.
In 1995, Ryan helped launch an empty website. He kept it because it was empty. He later noted that this experience led him to DoubleClick, where he noticed that many people in media were not working with the internet, but he saw something valuable. DoubleClick was eventually sold for $1.1 billion.
Ryan resigned from DoubleClick in 2007 and founded AlleyCorp. The venture studio has launched companies including Gilt Groupe, Business Insider, 10gen (later renamed MongoDB), a wedding registry company, and Nomad Health (founded in 2015), which connects doctors to temporary healthcare jobs. In 2015, Axel Springer acquired Business Insider for approximately $442 million. Hudson's Bay acquired Gilt Groupe for $250 million. MongoDB went public on Nasdaq in 2017.
Ryan co-founded Transcend Therapeutics in 2018 to develop new drugs for mental illness. In 2023, he completed a 101-kilometer ski crossing to the South Pole. Otsuka acquired Transcend for $700 million upfront with an additional $525 million contingent on future sales. In July 2026, AlleyCorp announced a $335 million second fund focused on supporting early-stage companies.
Ryan described an exercise of listing 20 trends expected to persist for 10 years, then analyzing their implications. Examples include social trends, healthy eating habits, restaurant automation, and the gig economy. He emphasizes that building a significant company requires betting on long-term trends rather than short-term fads.
Ryan explained that major companies cannot be built in two or three years. A 10-year timeframe is necessary. Betting on trends that are already peaking or fading means arriving too late. He cited internet advertising as a correct 20-year bet and psychedelics as a significant trend for mental health that is now five years into its development. Nuclear power, creator economy, and value-based care represent other multi-year bets.
Value-based care refers to a government-created system that incentivizes hospitals and doctors to reduce costs. Providers can become economic partners by finding ways to lower expenses while maintaining care quality. Ryan noted that AlleyCorp has multiple companies operating in this space.
Ryan has not yet identified a product concept in longevity despite attending Doc, a conference in Napa Valley focused on longevity and science. He maintains an interest in learning but has not translated this into a business opportunity.
Ryan organizes four events. Deep Tech in New York brings together 450 people to discuss emerging deep tech trends. Digital Health takes place in New York. Doc focuses on longevity. Odyssey convenes 100 talented individuals to exchange ideas in a less commercial, more intellectual setting.
Ryan leads a group of 20 people to China for Odyssey Two to observe what China does well and what it does poorly. He also organizes hiking trips with 30 participants in Switzerland and skiing trips, including one with 16 people off-piste in Val d'Isère. These trips are designed to facilitate meaningful conversations and learning.
Hiking trips last three to four days with approximately 30 people. Activities run from 8 a.m. to noon, followed by afternoon sessions on topics such as climate change, nuclear power, or consciousness. Evenings include meals and further discussion. The goal is for participants to become familiar with 20 new people from diverse fields.
Ryan described early experiences with Peter Thiel's secret society, where small tables of four or five people used fixed seating and moderators to encourage diverse interactions. He prefers structured mixing during the first two nights of events, allowing participants to connect with people they might not otherwise meet. The final night is more open.
Ryan organizes an annual four-day bike trip on mountain paths with eight participants. Each person prepares a 20-minute discussion on a chosen topic. Past topics have included crypto (before it was widely known) and how to handle money with children. Discussions are intentionally broad.
Ryan met Shopify CEO Toby in 2008-2009 when the company had approximately 10 employees. He became Shopify's first advisor outside the founding team. Ryan believed e-commerce would grow over 10 years and that mobile broadband would expand significantly. He noted that Shopify's early focus on mobile positioned it well.
Ryan described asking companies to project where their industry will be in 10 years. He emphasized that successful forecasting combines spontaneous feeling, innate instinct, and educated guesswork rather than relying solely on specific data sources.
Ryan discussed second-order consequences of trends. For example, falling bandwidth prices in 2003 made content delivery costs drop from $10 per thousand to lower levels while advertising revenue remained around $1 per thousand. This mismatch prevented certain business models from working at the time, though YouTube later succeeded when the economics aligned in 2005.
Ryan learned about Vente Privée in France, a flash-sale business generating $1 billion by selling discounted high-quality brand products at specific evening moments. He observed long lines at sample sales in New York and realized people outside major cities lacked access. Gilt Groupe reached $175 million in revenue in its second year and $500 million in its fourth year.
As department stores improved their websites and competitors like Farfetch entered the market, Gilt's unique position eroded. The flash-sale model became commoditized. Ryan noted that Gilt lacked a sustainable moat despite its early growth. The company was eventually sold to Hudson's Bay for $250 million after earlier valuation discussions of $400 million to $1 billion.
Ryan described Gilt as a "falling knife" that required an exit decision. He has not invested further in e-commerce, viewing it as too mature. He contrasted this with areas like cancer treatment, nuclear power, and psychedelics, where significant value remains to be created.
Ryan's early roles at Prudential, INSEAD, Euro Disney, and United Media taught him financial fundamentals and operational management. At United Media, he served as CFO and COO, managing 50 people and handling operations and finance. He felt comfortable with numbers and business fundamentals but preferred not to work in large corporate environments.
While at United Media, Ryan read a business article about the internet and immediately recognized its potential for communication, messaging, and commerce. In 1995, he launched a Dilbert website that succeeded because it served tech enthusiasts without browsers. He sold hard-coded advertising to IBM for two weeks and began merchandising T-shirts and ties.
Ryan proposed creating an internet division within United Media and requested several million dollars to build it. The executive he approached was a traditional media person who responded that the company would "wait for the next internet," which Ryan interpreted as a lack of understanding. The executive was approximately Ryan's current age of 61.
In 1996, Kevin Ryan observed the early internet ecosystem and noticed that people were increasingly coming online rather than going offline. Users were beginning to purchase accessories and use maps online. He recognized that e-commerce was going to increase substantially and that activities like buying things from anywhere and viewing content from anywhere would become normal worldwide.
Ryan decided to start an internet company and was actively recruited by Silicon Valley companies due to his one-year internet experience, which made him one of the most experienced individuals in New York at that time. He met two people who had started DoubleClick six months prior - they were very smart and technical. Despite their invitation to join, Ryan initially wanted to stay in New York, believing he could build a successful company there.
Ryan joined DoubleClick as the 10th or 12th employee. He worked as CFO for a few months, then became President, and eventually CEO. As a founder-like figure without technical expertise, he positioned himself as a team player focused on company success.
Ryan's key contribution was his ability to make fast decisions and adapt quickly. Within the first three years, DoubleClick expanded to 25 countries while competitors were only in six countries. When approached by Procter & Gamble, who wanted to work with companies having global presence, Ryan's rapid expansion enabled partnerships with major corporations including Microsoft. This led to near-total market domination.
Ryan noted they made some mistakes but ultimately built the world's best company. DoubleClick would later become an independent company valued at $100 billion.
Rather than creating a traditional incubator like Y Combinator where founders bring their own ideas for selection and equity exchange, Alcorp operated differently. Ryan and his partner invested approximately $500-1000 in each company and worked as co-founders. Each company spent about six months to one year proving concept before seeking venture capital funding.
Alcorp built the product, often launched it, and then went out to raise money. They focused on companies completely, completing three companies initially, then another three batches for a total of six companies. Three were hugely successful: Gilt, Business Insider, and MongoDB.
Alcorp was formed between 2005-2008, with the last three companies starting in the same year. Ryan worked with Dwight Merriman, described as one of the best technicians who handled the technology for both DoubleClick and MongoDB. Ryan focused on business direction including finding CEOs, building businesses, and raising money.
Ryan identified several critical skills: the ability to identify trends and opportunities, recruit talented staff, and form capital through fundraising. He emphasized that when working with large companies like Procter & Gamble, they require worldwide presence, necessitating critical capital raising to reach necessary velocity.
MongoDB took notably longer to develop. Business Insider began with Sam Parr and Sean Perry, starting with just a few people handling New York technology coverage. When their manpower decreased, they gradually appointed more people as the website gained sufficient response. This approach helped spread domination despite initial hesitation many founders feel about expanding teams.
Gilt began with weekly sales of women's clothing, expanding to two, three, then five sales per week. Within about a year, they added men's clothing, children's clothing, travel, and household items.
Business Insider started with only three people working exclusively with the New York technology sector. They created a Wall Street category, then added another section. As they continued recruiting, journalists could add categories, eventually reaching 600 journalists covering defense, retail, and other sectors.
When Ryan and Dwight made their initial $10 million investment in 50/50 ratio, they took over 30% of company shares. From day one, share quantities began decreasing. They planned this dilution through subsequent fundraising rounds.
Between 2005-2008, Alcorp recruited talented individuals by selling their New York-based company, which was the most valuable startup at the time. This gave them credibility and the ability to help portfolio companies raise money. Henry Blodget joined Business Insider after 30 minutes of discussion, recognizing it as a great idea.
Business Insider was among the first to move away from traditional practices. While Wall Street Journal and Business Week updated their sites daily and waited for paper news, Business Insider posted multiple times during story development, collected more information, and tested headlines. They would test four titles, giving each five minutes, then use whichever received the best response.
Business Insider never did marketing but wrote content so effectively that they reached 100 million unique visitors. This organic growth strategy proved successful despite skepticism from others who said it wasn't a viable strategy.
Alcorp maintained a small team of 23-24 full-time employees. When Ryan and Dwight were working with just one or two additional people, they would brainstorm ideas in conference rooms, sometimes going months without new concepts.
Ryan described falling in love with ideas intellectually. An idea would come to mind and occupy his thoughts for a week, then two weeks. If he couldn't stop thinking about it, he knew it was worth pursuing. He emphasized the importance of understanding whether people would read business news online and whether established organizations could be outperformed.
For Business Insider, Ryan prioritized product quality over traditional departments. He believed a great product was essential, noting that Business Insider reached 100 million visitors due to product excellence. He acknowledged advertising-dependent businesses face challenges in selling ads even with large audiences.
Ryan avoided pre-pitching ideas to investors like Union Square Ventures before proving functionality. He would approach 20-25 firms during fundraising, finding that roughly half the time his preferred investors weren't interested, but others would fall in love with the idea.
Ryan never thinks about exits, focusing instead on whether products solve real problems that everyone wants to use. He believes solving the product question enables everything else - raising money, hiring people, and executing all other aspects.
Ryan invested in Valor (Atomic-E), a small modular nuclear reactor company, three years ago when nuclear wasn't popular compared to fusion. The company had a $20 million valuation at investment time and recently raised $6 billion from Sequoia. Ryan noted the Trump administration advanced both psychedelic and nuclear energy sectors despite his general criticism of the administration.
Alcorp's strategy involves selling one-third of positions in 4-5 year old fund companies during good decision points. This provides returns to LPs and team members while allowing hedging and market reinvestment, even while remaining optimistic about portfolio companies.
Alcorp's LP base is small, with Ryan as the largest LP, followed by family offices, some institutions, and small endowments. The first fund achieved approximately 60% IRR, with no fund falling below 50% IRR across three funds totaling $335 million.
Ryan prefers focusing on company creation rather than scaling into a large fund operation. While typical VC funds emphasize 2% management fees, Alcorp focuses on the 20% carry. He wants to maintain their current approach of adding verticals and geographical areas while preserving what they do well.
Ryan mentions Zola, noting 150,000 couples will use their wedding registry this year from an idea conceived 12 years ago. He also discusses nuclear energy's role in New York state for fuel consumption control and data center support, as well as psychedelic compounds for PTSD treatment potentially benefiting 1 million people within 10 years.
Ryan's ping pong journey began in his basement and progressed through neighborhood, high school tournament, regional tournament, and state tournament levels where he lost badly. In New York, he found White Rock Walker's ping pong club and met Moses, Nigeria's 14th-ranked Olympic player from 1992. At Yale, he joined the varsity ping pong team and continues playing regularly.
Kevin Ryan emphasizes that CEOs should take 4 to 5 weekends off per year, advocating for intense 47-week work periods followed by substantial time away. He explains that his behavior as a CEO is influenced by this policy, and he advises maintaining perfect isolation during these breaks without checking work communications.
When starting his company, Ryan worked intensely with the goal of going public within 24 months. He describes taking on ten concurrent projects and acknowledges that this level of intensity affected his family life. He worked late nights while trying to maintain his own pace, but admits he paid the price by reducing time spent with friends and attending cultural events.
Ryan made a conscious decision to prioritize three things: hard work, spending time with family, and maintaining physical fitness, while reducing everything else by approximately 80%. He specifically mentions that when his children went to college 8 years ago, he gained new work opportunities and more time, allowing him to engage in more interesting work. He takes pride in having spent at least 4 to 5 weekends per year making memories with his family.
At age 54, Ryan maintains a flexible work schedule where he works every day but sometimes only needs 2 to 3 hours for tasks. He describes taking extended time in France where he would engage in sports like biking, tennis, and swimming in the morning, then allocate time from 9 AM to 12 PM for meetings according to New York time. He mentions planning a 4-day trip to Ibiza for a wedding the following week.
Ryan describes reading Michael Pollan's book "How to Change Your Mind" in 2017, which was on the New York Times Top 10 Books list in 2019. At age 54 (8 years prior to the interview), he had never considered psychedelics and had no prior knowledge about them. The book literally changed his thinking, leading him to understand that these substances could be very useful for people, with academic research showing they could help with PTSD and anxiety.
While serving on Yale's board, Ryan learned about Yale's Center for Psychedelic Research. He spoke with John Crystal about depression and other applications, and also interviewed Ben Kelmendir, with whom he spent a week in the desert. Ryan became one of the biggest donors to Yale's psychedelic research center, though at the time he had no intention of investing in the space.
In 2021, Ryan decided the next stage would be a profitable commercial venture rather than continued nonprofit work. He recognized that FDA approval for compounds would cost $200-250 million, which nonprofit fundraising couldn't adequately support. Working with his former Alicorp team member Blake Mandel, they began exploring the creation of a company around methylone.
Ryan's first methylone experience occurred around 2015-2018, describing it as an underground experience that was difficult to obtain but resulted in an incredibly beautiful, calm experience. He notes it has a relatively short duration compared to MDMA, which he found appealing. From a business and societal impact perspective, he saw methylone as something people didn't know about but which had fundamental results that could be influential.
Ryan explains that methylone has some advantages compared to MDMA that most people don't understand. While MDMA is excellent for entertainment purposes and has good trial results, methylone can be taken once a week, whereas MDMA cannot due to being more toxic and reducing serotonin more significantly. He references Sasha Shulgin's observation that using MDMA more than four times per year decreases functionality, and some people may become resistant or insensitive to it.
Methylone's duration of functionality is more compatible with healthcare settings. The company secured patents for PTSD, depression, and anxiety, preventing others from using these three indications for the next 20 years. They started the FDA approval process and achieved incredible fundraising results despite operating during a difficult time for psychedelics fundraising.
Ryan notes that traditional psychedelic therapy models requiring 4-6 hours of continuous therapist presence aren't scalable or cost-effective. He observed that adding extra nurses and manpower would make costs unaffordable. The FDA advisory committee indicated they didn't know how to evaluate or assess psychotherapy quality, which presented additional challenges.
Ryan acknowledges learning from early mistakes in the ecosystem and changing their approach. He notes that FDA attitudes changed immediately under the Trump administration, which signaled they wanted this to happen. He mentions that in 2015, very few people had tried psychedelics, and those who had were quiet about it, particularly outside the Bay Area.
Ryan reveals he did a podcast about ibogaine in 2015 with Martin Polanco and Dr. Dan Engel in Mexico, making him an early participant in the space. He notes the political safety of focusing on PTSD applications for elderly soldiers, as no politician would oppose this regardless of political affiliation.
Methalone was established as a public benefit corporation, meaning elementary shareholders promise to give 10% of their profits to a foundation. Ryan and Blake will distribute this money, planning to give $20 million over the next 9 months to various sectors related to psychedelics. They hired a part-time staff member to handle this work.
Due to political considerations around PTSD in elderly soldiers, the company recognized that the industry's main focus has been on sex persecution. Their trials have 60% women participants because women are more infected with PTSD than men. They are trying to find reasons to support neglected populations and allocate some of the foundation money accordingly.
Ryan emphasizes the importance of accountability mechanisms in public benefit organizations. He recounts asking a manager of such an organization what would happen if they later decided to change their declared goals, and the manager was silent. Ryan stresses that this represents a very big issue in how the work in progress is being handled, noting that allocating $20 million isn't simply an open casting call that would result in millions of bizarre proposals.
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