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My First Million$100M hedge fund manager: Do not make the mistake of dying rich
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CHAPTERS
- 0:00 – 0:51
Setting the stage: making money vs. living a rich life
Bill Perkins opens with a humorous take on not wanting to be “the guy” after writing a book, and the hosts frame the show’s shift from getting rich to living richly. Shaan sets up the conversation as both Bill’s money-making story and how he thinks about using money well.
- •Bill says he doesn’t want fame or to build a personal brand; he wants to live his life
- •Shaan explains the show’s evolution from money-making to living a “rich life”
- •The conversation tees up Bill’s book themes as a lens for discussing money, time, and fulfillment
- 0:51 – 2:06
How Bill Perkins built his initial capital in energy trading
Bill explains how he started from the bottom on the New York Mercantile Exchange floor and moved into natural gas derivatives. He describes hating brokering, moving to Houston during deregulation, and becoming a trader where he began making significant money.
- •Bill begins as a clerk on the NYMEX floor and targets the new natural gas futures market
- •He becomes an over-the-counter broker, earns decent money, but dislikes the job
- •Deregulation drives recruiting to Houston; Bill moves and starts trading on a derivatives desk
- •He contrasts being a broker (agent) vs. being the trader (principal)
- 2:06 – 3:41
“Price go up or down”: trading as insurance and the short natural gas edge
Bill simplifies derivatives trading as betting on price direction and volatility, then reframes it as selling insurance based on perceived fair value. He gives a concrete example of selling winter hedges and describes how being short natural gas over time produced most of his gains.
- •Bill explains trading as taking positions on price and volatility (including spreads)
- •He says traders are more like insurance agents than constant speculators
- •Example: selling winter hedges to buyers worried prices will rise, leaving him exposed to price increases
- •Bill says winter risk premium often “bled out,” and prices generally fell, benefiting his short bias
- 3:41 – 9:11
Concentration risk and the mistake of being too cautious when young
Asked about wealth-building as an employee and big profit swings, Bill describes the compensation model at independent hedge funds and admits he didn’t take enough personal risk early. He argues that when you’re young and can get another job, concentrating risk can make more sense than protecting yourself from worst-case outcomes.
- •Sam notes trading can make employees rich; Bill describes “eat what you kill” compensation
- •Bill says he could have made more by investing more of his own money in the fund
- •He shares a past belief: it’s okay to have no money and a job, or money and no job, but not neither
- •Bill later views that belief as wrong for his younger self and says maximizing risk when young is often optimal
- 9:11 – 10:16
Big drawdowns, huge up years, and “stay in the game”
After the sponsor break, Bill quantifies the volatility he lived through and explains why survival matters more than any single year’s result. He compares trading to insurance underwriting: bad years are inevitable, but if you avoid getting wiped out, the edge can play out over time.
- •Bill describes performance swings of roughly down 50% to up 250%
- •He puts the stakes in the hundreds of millions and describes cyclical seasonal build-ups and drawdowns
- •He emphasizes “the name of the game is to stay in the game” to realize long-term edge
- •He uses an insurance analogy: catastrophic years happen, but premiums and returns can be strong afterward
- 10:16 – 12:36
A decade of intensity: obsession, learning edge, and what he’d do differently
Bill confirms the “maniac” phase of trading—being constantly on due to positions and complexity. He says obsession builds informational advantage, and he reflects that if he could do it over, he’d choose equities for the larger capital base and structural tailwinds.
- •Bill says traders become obsessed with the puzzle to build knowledge and informational edge
- •He describes trading as never truly being “off” when positions are on
- •Asked what he’d do differently, he says he would’ve gone into equities because the market is bigger
- •He notes large equity funds can earn substantial fee revenue relative to operating costs
- 12:36 – 15:02
No “party at 85”: the net-worth peak is a date, not a number
Bill explains why his current age changes how he thinks about compounding and future wealth. He argues that the body is a decaying asset, so the ability to convert money into meaningful experiences declines—making the timing of wealth (and experiences) more important than the absolute number.
- •Bill says at 57 he’s not trying to optimize for a distant future like age 85
- •He describes an early goal (millionaire before 30) and admits he didn’t have a thoughtful “cap number”
- •He says the important concept becomes a “net worth peak” as a date rather than a number
- •He frames aging as a declining conversion rate from money to fulfillment as the deathbed approaches
- 15:02 – 20:00
The fear of a wasted life: money as hours of life and death as a wake-up call
Bill describes how his thinking evolved through books, conversations, and repeated reflection rather than a single epiphany. Shaan reads a resonant excerpt about “pumping the well” instead of drinking, and Bill says his core fear isn’t losing money—it’s wasting his life.
- •Bill cites reading “Your Money or Your Life” and adopting the view of money as exchanged life-hours
- •He describes mapping experiences to life stages (e.g., when certain pleasures or goals fit)
- •Shaan reads an excerpt about death waking people up and people spending life pumping instead of drinking
- •Bill says he fears wasting his life more than losing money, status, or what he’s built
- 20:00 – 25:37
Crush your ego: why people don’t take the risks they say they want
Bill argues ego—not financial risk—often blocks people from pursuing the life they want, because they can’t tolerate a status drop or looking foolish. He and the hosts explore how self-awareness helps but still requires action, and Bill explains how he tries to practice humility and directness without losing kindness.
- •Bill says many people avoid entrepreneurship or big moves due to ego and fear of judgment
- •He claims people can often handle the financial downside, but not the social/status downside
- •He describes a constant internal practice: apologizing when needed, not clinging to being right, and not over-weighting others’ opinions
- •He emphasizes kindness while giving “straight dope,” and explains how that can be perceived as abrasive
- 25:37 – 31:34
Reprogramming your responses: cultural programming and maximum accountability
Bill describes realizing many preferences and behaviors are learned programming, not innate truths, and explains how he evaluates responses based on whether they serve his goals. Shaan connects this to an “internal locus of control,” and they discuss rewriting personal narratives with total ownership to escape victim mindset.
- •Bill says many desires come from “cultural osmosis” and marketing rather than genuine values
- •He describes analyzing stimulus-and-response patterns and replacing reactions that don’t serve his goals
- •Shaan notes a pattern among successful people: controlling one’s own reactions and accountability
- •They discuss an exercise of rewriting painful life stories with 100% ownership to reduce victim mindset
- 31:34 – 36:54
Seasons of balance: family life, pendulum swings, and time buckets vs. bucket lists
The conversation turns to designing life across changing family and life stages rather than trying to “balance” everything daily. Bill explains the idea of time buckets—recognizing multiple “deaths” of past selves—and argues that sequencing experiences correctly matters because many don’t transfer well to later decades.
- •Sam describes shifting preferences after having kids; Bill discusses balancing fulfillment with family responsibilities
- •Bill says balance is a pendulum across seasons (grinding, vacationing, partying, spiritual work), not a daily even split
- •He explains time buckets: different life periods have optimal experiences and constraints
- •He critiques “bucket lists” that defer everything until the end and says life requires correct ordering like Tetris
- 36:54 – 42:21
Planning the year and confronting health drift (and outsourcing accountability)
They discuss how Bill and the hosts plan time intentionally, from ongoing life-arc conversations to dedicated planning days. Bill identifies health adherence as his biggest current dissatisfaction and explains how he evaluates fitness against desired late-life activities, then describes hiring support to increase accountability.
- •Bill describes planning around specific life windows (e.g., living abroad while a child is under five)
- •Shaan shares he now spends three days a year planning the year to shape the other 99%
- •Bill says his biggest dissatisfaction is health adherence and admits he tells himself “victim stories” that are excuses
- •He uses VO2 and desired late-life activities as a framework, and describes hiring trainers (and possibly traveling with one) for accountability
- 42:21 – 52:46
Why the book is called Die With Zero: regrets, reader impact, and not sacrificing youth
Bill explains how the title emerged from brainstorming and why it captures the idea of using resources fully—and dying with zero regrets. He shares patterns from readers (especially changing inheritance plans) and revisits a formative regret from his 20s about not taking a long trip, illustrating how delaying experiences can permanently diminish them.
- •Bill says “Die With Zero” also implies “die with zero regrets” by leaving everything on the field
- •He notes publisher concerns about selling a book with “Die” on the cover but chose provocation
- •He highlights reader changes: earlier gifting/inheritance, shifting retirement timing, reallocating time, and prioritizing health
- •Bill recounts skipping a long trip in his 20s and later realizing the experience didn’t translate well to his 30s (too “bougie,” friends not joining)
- 52:46 – 1:00:44
Still working, but for fun and fit: what money is for and what he buys
Bill clarifies he hasn’t stopped working—he still enjoys puzzles and runs multiple ventures—but insists he would quit if extra dollars stopped adding fulfillment. He describes current businesses and explains how he weighs expensive interests like yachting and private travel against the tradeoff of giving up present time for future benefits.
- •Bill says he still works because the puzzle is enjoyable and there is still marginal utility in earning
- •He names his ventures: a hedge fund plus two startups (Sky5 and SimMax) and continued trading
- •He describes spending motivations: time savings and enjoyment (e.g., private travel) and expensive hobbies (e.g., yachting)
- •He discusses the “cell phone ankle monitor” effect—work flexibility as both blessing and curse
- 1:00:44 – 1:20:35
Spending $15M on art: the ‘Sugar Shack’ auction, collecting as preservation, and fame boundaries
Bill tells the story of pursuing and winning a high-stakes auction for a culturally significant painting, including being surprised by the final price and a tense back-and-forth with another bidder. He explains how collectors signal what’s worth preserving, why he views the market as mispricing certain work, and how he now loans the painting to museums. The episode closes with Bill’s take on why he avoids higher fame, plus a possible future book collaboration he finds tempting.
- •Bill explains why the painting mattered to him culturally and personally, and how he learned it was coming to auction
- •He recounts the auction dynamics: expecting a much lower range, bidding war escalation, and an exchange with the competing bidder
- •Bill frames collecting as signaling preservation value for future generations and describes the market “arbitrage” he saw
- •He says the painting is on museum loan and that he avoids being too famous because fame shrinks life and forces a persona; he mentions a potential book idea with Tim Urban but says he’s under a “no new projects” rule at home
