At a Glance
In this special episode of Invest Like the Best, host Patrick O’Shaughnessy is interviewed by David Senra, centering on the theme of "building a life by principles." Patrick shares his life-organizing principles, emphasizing that "the reward for great work is more work," and explores how to discover undiscovered talent. He argues that media and investing are fundamentally the same—both are a search for true understanding. Key takeaways include: relationships drive the world, people are more interested in others than anything else; hire based on output, not resumes; and the cycle of "learn, build, share, repeat." Patrick also reveals his motivation for founding Colossus magazine in 2025, and, citing observations from Bruce Springsteen and Sam Hinkie, stresses the importance of finding one's superpower and becoming a more authentic version of oneself.
Thematic Sections
1. Organizing Principle: Discover Undiscovered Potential and Help the World See It
Patrick O’Shaughnessy believes his life's organizing principle is to discover vast, undiscovered potential and to see it as an obligation to help it grow.
- Core Mechanism: Patrick connects this principle to computer scientist Brett Victor's talk "Inventing on Principle." Brett Victor's principle is that "digital creators should get immediate feedback," while Patrick's is: "When I see undiscovered talent, I have an obligation to get to know them, learn from them, and start introducing them to other people." This principle guides all his decisions, whether in investing, building a team, or making friends.
- Data & Argument: Patrick cites a line from the Upanishads as the cornerstone of his worldview: "Those who feed the hungry protect me. Those who do not are devoured by me." This led him to the epiphany that "the whole point of life is to help other people." His favorite question is "What is the kindest thing anyone has ever done for you?", and two-thirds of the answers are "Someone bet on me when I wasn't worth it." This reinforces his belief in seeing potential before others do.
- Deduction & Validation: Patrick believes a good principle can be applied universally. He proves this by supporting David Senra's podcast—an act with no apparent direct return. This action stems from principle, not goals. He believes that by following this principle, opportunities will come from "left field," rather than through setting specific targets.
2. Growth Without Goals: Embrace the Unexpected, Don't Set Destinations
Patrick O’Shaughnessy explicitly states he does not set goals, instead embracing "Growth Without Goals," because everything meaningful to him has come from the unexpected.
- Historical Context: At age 28, on the verge of becoming a father, Patrick began thinking, "What kind of example do I want to set for my son?" This prompted him to write the essay "Growth Without Goals." He observed that setting goals puts on "blinders," allowing one to see only the known path, while everything meaningful to him—from meeting David Senra to starting new companies—came from "left field."
- Mechanism Breakdown: He champions the cycle of "Learn, Build, Share, Repeat." In his 20s, he read voraciously, then shared his insights via an email list, which spawned a podcast, which led to business opportunities and investments, and eventually circled back to writing in-depth profiles (Colossus). All of this stemmed from his love of reading—a high-frequency hobby—not from any preset goal.
- Unique Judgment: Patrick believes that for highly talented people, setting goals often means they can achieve them, but this kills surprise. He prefers the concept of "progressive overload"—constantly challenging himself without knowing where it will lead. He cites Sam Hinkie's description of him as "red on the color wheel" to illustrate that once he is interested in something, he becomes intensely focused, but his interests can also shift easily.
3. Media and Investing: Two Sides of the Same Coin
Patrick O’Shaughnessy argues that media and investing are essentially the same thing: both are about finding and supporting people with unique stories and potential.
- Mechanism Breakdown: Patrick distills the principle of a "great story" into three points: originality, hardship, and transformation. In investing, he looks for founders with unique life paths (originality), who have endured hardship, and who can create significant change for their clients (transformation). In media, he tells these people's stories through his podcast and magazine (Colossus), which is essentially "investing" in their narrative.
- Data & Argument: Patrick's decision to start a magazine (Colossus) in 2025 was widely considered a "stupid idea." However, he believes that if something sounds like a good idea, it means competition is already fierce. He pursues things that "sound stupid but aren't." He cites Walt Disney, who, when told amusement parks were "vulgar," replied: "That's the point. Mine won't be."
- Deduction & Validation: Patrick believes people's interest in others surpasses everything else. An in-depth profile is the "ultimate spotlight and form of attention." He found the best author, Jeremy Stern (now Colossus editor-in-chief), by reading numerous profiles. He predicts Colossus's scale could eventually surpass the podcast itself, as it is no longer limited by his personal time and energy.
4. Relationships Drive the World: Deep Connections Are the Ultimate Wealth
Patrick O’Shaughnessy emphasizes that relationships are the core force driving the world, and having a few people he would "do anything for" is his most valuable asset.
- Mechanism Breakdown: Patrick believes people's work is essentially "learning, then packaging what you've learned for others to consume." And all of this is built on relationships. He gives the example of recording a show for free at the Aman Hotel in New York, which was entirely due to a personal connection with a friend.
- Data & Argument: He shares a "ten roles" game, where participants list ten roles they play (e.g., father, podcaster, friend), then discard them one by one until only one remains. His father-in-law's final role was "grandfather," and specifically "the Michael Jordan of grandfathers." Patrick argues that this kind of dedication, which narrows ambition to its purest form, is as successful as that of Elon Musk or Jeff Bezos.
- Deduction & Validation: Patrick believes health, work, and relationships are the three pillars of life. However, he found that when he finally found work he loved and focused on core relationships, his long-standing health issues miraculously improved. He quotes Rhys Duka's maxim, "Simplify your life with rhythm and harmony," emphasizing "fewer but deeper relationships, fewer but better things."
5. Leadership and Self-Awareness: From "Heroism" to "Over-Communication"
Patrick O’Shaughnessy reflects on his growth as a leader, moving from relying on individual heroism to learning to lead a team through over-communication and repetition.
- Historical Context: Patrick admits he used to be "red on the color wheel"—intensely focused on something, but when his interest shifted, it felt like "whiplash" for those around him. Sam Hinkie once woke him up with an example: Patrick went from never thinking about starting a fund to quickly establishing one and raising capital within a month, which made him realize how fast he could change.
- Mechanism Breakdown: He cites Ravi Gupta's definition of leadership: "A great leader is someone others want to follow." One key trait that makes people want to follow is "over-communicate." He mentions Elon Musk's "four-part algorithm," which Musk repeated so often that his executives could recite the next part along with him. Patrick's own mantra is "The reward for great work is more work," and he uses constant repetition of this phrase to screen and motivate team members.
- Deduction & Validation: Patrick believes a common trap is that talented people can accomplish a lot on their own ("heroism"), but to earn the right to do more "great work," one must become an excellent leader. He quotes Jim Sinegal (Costco founder): "If you don't spend 90% of your time teaching, you're not doing your job as a company leader."
Positions Mentioned
This section does not involve specific investable companies, so it is omitted.
Judgments Worth Remembering
1. "The reward for great work is more work" (Patrick O’Shaughnessy): This is Patrick's core mantra, used to screen and motivate team members. He believes truly talented people understand that the ultimate reward for work is not money, power, or fame, but the privilege of continuing to do the work they love.
2. "Red on the color wheel" (Sam Hinkie on Patrick): This metaphor accurately describes Patrick's personality: when focused on something, he becomes intensely productive ("the Eye of Sauron"), but once his interest shifts, he changes direction quickly, causing "whiplash" for those around him. This is both his superpower and his weakness.
3. "Growth Without Goals" (Patrick O’Shaughnessy): Patrick believes setting goals limits one's field of vision; everything meaningful to him has come from the unexpected. He champions the concept of "progressive overload"—constantly challenging himself without knowing where it will lead. His life is the natural result of the "Learn, Build, Share, Repeat" cycle.
4. "People's interest in others surpasses everything else" (Patrick O’Shaughnessy): This is the core belief behind Patrick's founding of Colossus magazine. He believes in-depth profiles are the "ultimate spotlight" because people are naturally curious about the stories and personalities of others (especially successful ones). He cites Larry Ellison as an example, showing how Ellison elevated Oracle's brand by framing it as a personal duel with Bill Gates.
5. "Hire based on output, not resumes" (Patrick O’Shaughnessy): When searching for the Colossus editor-in-chief, Patrick didn't post a job listing; instead, he read numerous profiles and found the best writer, Jeremy Stern. He tells the story of Charlie Munger, who found a CEO by "finding a great CEO and saying, 'Come do this for us,'" rather than "hiring for potential."
6. "Inventing on Principle" (Brett Victor / Patrick O’Shaughnessy): Patrick applies Brett Victor's concept to his own life. Brett Victor's principle is "digital creators should get immediate feedback," while Patrick's is "When I see undiscovered talent, I have an obligation to help it grow." A powerful principle can guide all decisions and become a lifelong mission.
7. "The privilege of a lifetime is being who you are" (Joseph Campbell / Patrick O’Shaughnessy): Patrick believes the most sustainable form of creation is "pouring yourself into what you are creating," and that this creation serves others. He has never seen anyone who has experienced this joy of creation turn back, as it seems to be the ultimate experience all humans seek.
8. "Clean fuel vs. dirty fuel" (Patrick O’Shaughnessy): Patrick distinguishes between two energy sources that drive people. Dirty fuel (e.g., hatred, pain, the desire to prove oneself) is effective but consumes the person. He champions clean fuel (e.g., love, the desire to serve others), believing it is the source of sustainable success and inner peace. He argues this by contrasting Bruce Springsteen (who eventually switched to clean fuel) with Lyndon B. Johnson (who never did).