This interview is about Ric Elias, who survived a plane crash and realized that 'living good' is not the same as 'living well.' He believes society tricks us into always wanting more, which steals inner peace. He no longer invests to grow capital; instead, he uses his money for things that matter, like buying a last-place basketball team in Puerto Rico and turning it into a championship contender through a 'team-first' culture. Key holdings: Red Ventures (his company, from $2M to ~15 firms), Bankrate (bought for $1.4B), and the Puerto Rico basketball team (from worst to finals).
Ric Elias is the CEO and co-founder of Red Ventures, which started in 2000 with $2 million and has since grown into a global digital operating platform owning about 15 companies, including Lonely Planet, The Points Guy, and Bankrate. The core thread of this interview is the distinction between "living good" and "living well", and how to translate business success into a deeper sense of purpose. The most impactful takeaway from the entire episode: Elias believes that the 90-second "death notice" he received during the 2009 Hudson River emergency landing made him realize that "wanting more" is a socially engineered trap, and that the true goal should be inner peace and forgiveness. He consequently decided to stop investing for capital appreciation and instead use his capital to "compound" other things that are meaningful to him.
Ric Elias considers the 2009 emergency landing of US Airways Flight 1549 on the Hudson River the greatest gift of his life. Seated in 1D, after the captain said "brace for impact," he had 90 seconds of "absolute certainty that he was going to die." Those 90 seconds gave rise to three core regrets: ① He wasted too much time letting his ego drive his actions; ② He failed to focus on leaving a "purpose"; ③ He regretted not expressing love and forgiveness more fully. Elias emphasizes that this experience led him to make a vow: "Don't let this experience be something that happened to me; let it become a part of me." He has since practiced "instant forgiveness" (forgiving when the other person doesn't apologize) and believes that "forgiveness" is the kindest gift one can receive. Readers should note: Elias uses this experience to argue for a shift in his life philosophy, but this is a highly personal narrative, not a replicable investment framework.
Elias distinguishes between the concepts of "good" and "well," arguing that the former reflects external circumstances (e.g., "business is good") while the latter reflects an internal state (e.g., "I feel well"). He admits that over the past two years, he has experienced some very difficult personal events, making his external environment "bad," yet he felt "well" because he handled those situations in the best way possible, gaining growth and peace from them. He breaks down "well-being" into "well" (inner peace) and "being" (a state of existence) — the latter being a state of "having nothing to do," where one stops "doing" for social approval and instead "exists" for inner connection. Elias believes that most financially successful people are "not well" because "vanity is the greatest sin in life," and society's reward system for achievement makes it difficult for people to find the muscle of "being."
Elias explicitly states that he has stopped investing for capital appreciation and now uses his capital to "compound" other things that are important to him. He says: "I don't invest in funds anymore. I don't invest in anything. I don't want to compound capital... I want to use my capital to do things that are truly important in Puerto Rico." He attributes this shift to a wariness of "wanting more" — he believes society sets a trap: every time you reach a peak, you see a higher mountain, and "wanting more" robs you of inner peace. The core of Elias's investment philosophy is "decomposing risk": he will only invest in businesses with "one variable" (i.e., only one key uncertainty) and avoids businesses that require "three variables" to all align for success. He also emphasizes that he "likes to bet, but hates to gamble" and believes that "a good bettor needs to have had bad bets," otherwise they are just "hitting 85 mph fastballs."
Elias describes Red Ventures as an "operating private equity platform with permanent capital," whose core advantage lies in "culture" serving as the "connective tissue" between its portfolio companies. He explains that because the company has no exit pressure (permanent capital), they can invest in long-term projects that other institutions are unwilling to touch. Culture is specifically embodied in seven "belief statements," with "Making every second count" being his current focus — because operational discipline has loosened since the pandemic, and he worries that the new generation of employees lacks the "hunger" of the past. Elias emphasizes that culture is not built through preaching, but is defined by "what you tolerate" : they once signed a big-name free agent but fired him three days later because "he was an asshole"; they also suspended their best player for behavior inconsistent with the culture. He concludes: "Culture is like a shark; it has to keep moving to survive."
Elias views his experience of buying a last-place basketball team in Puerto Rico as a pure cultural experiment. The team had never made the playoffs and was predicted by 11 out of 12 teams to finish last before the season. Elias set three rules: ① Invest in the players so they could earn more money (equipping a full gym and coaching staff); ② Don't focus on specific goals, but build a "system"; ③ No one is above the team. As a result, the team made it to the finals at the end of the season (a Game 7 was being played at the time of the interview). Elias believes the biggest takeaway was not the win or loss, but that the "team-first" culture gave the players a sense of belonging they had never felt before — the best player, who joined mid-season, said, "This is the best team I've ever been on." He quotes a Spanish saying: "Nadie me quita lo bailao" (No one can take away the dance I've danced), emphasizing that the value of the experience itself transcends the outcome.
| Position | Guest's Stance | Key Data |
|---|---|---|
| Red Ventures | Bullish (as a platform) | ~15 companies; started in 2000 with $2M; repaid investors principal + 10% interest in 2004; first external capital in 2010 (General Atlantic); Silver Lake invested in 2015; Bankrate acquisition price $1.4B |
| Bankrate | Bullish (as a milestone) | Acquisition price $1.4B; EBITDA multiple fell from 10x to 4x within 2 years of acquisition |
| UnitedHealthcare JV | Bullish (long-term partnership) | Joint venture focused on consumer health platform; CEO Andrew Whitty believes future health companies need to be "consumer-driven" |
| Puerto Rican Basketball Team | Bullish (cultural experiment) | Ranked 12/12 pre-season; made it to the finals; Elias has visited Puerto Rico 9 times |
1. "Living good" and "living well" are two different things (Ric Elias): The former reflects external circumstances, the latter is a state of inner peace; one can feel "well" even when external conditions are "bad."
2. "Wanting more" is a socially engineered trap (Ric Elias): Every time you reach a peak, you see a higher mountain; wanting more robs you of inner peace.
3. Capital should be used to "compound meaning," not "compound capital" (Ric Elias): He has stopped investing for appreciation and instead uses his capital to create social value in places like Puerto Rico.
4. Culture is "what you tolerate," not "what you preach" (Ric Elias): They signed a big-name player and fired him three days later because "he was an asshole"; they suspended their best player for behavior inconsistent with the culture.
5. The difference between "betting" and "gambling" lies in risk decomposition (Ric Elias): Only invest in businesses with "one variable"; he won't touch businesses that require three variables to align simultaneously.
6. The 90-second death notice taught him "instant forgiveness" (Ric Elias): The highest form of forgiveness is "forgiving when the other person doesn't apologize," which comes from accepting human weakness.
7. "Being" is more important than "doing" (Ric Elias): Society rewards "doing," but "being" is a state of having nothing to do and is the source of inner connection.
8. The cultural experiment of the "underdog" team proves: Team-first can transcend talent gaps (Ric Elias): A last-place team made it to the finals, and players said, "This is the best team I've ever been on."