There’s 98 days until 2027...Do this and you’ll thank yourself on Jan 1st

The episode opens with the hosts emphasizing that there are 99 days left in the year. The opening speaker argues that this period can matter more than a New Year’s resolution: listeners should treat the remaining time like an athlete’s fourth quarter and ask whether they have made their mark on the year. Although 99 days sounds short, he calls it “an eternity” in which someone can accomplish a great deal. The other host objects to measuring time in quarters, arguing that months—or even smaller increments—would create better urgency. He says the time assigned to a project often dictates how long it takes, comparing quarterly planning with Google Calendar’s default 30-minute meetings. If a meeting were set for 22 or five minutes, people would often finish within that shorter container. They connect this to Parkinson’s law: work expands to fill the time available, just as gas expands to fill its container. The practical conclusion is to shrink the container and use the remaining 99 days deliberately. They also joke that people observing Rosh Hashanah get an earlier annual-reflection and resolution cycle, effectively a two-month head start.

Shaan says he is trying to resist his natural identity as an “ADD entrepreneur” or “cortisol entrepreneur” who constantly spikes into stress. His theory is that weaknesses are difficult to convert into strengths; at best, they can be neutralized. The better approach is to build systems in which the weakness has fewer opportunities to appear. He gives the example of a person who is not self-motivated to exercise but pre-pays for a trainer to arrive at home, eliminating the option of simply choosing not to work out. Shaan applies this to his relationship with his CEO and co-founder, Joe. They mostly avoid discussing business throughout the day, reserving one 45-minute session each week for complaints and proposed improvements. Shaan must write his issues down in advance. By the time the meeting arrives, something that initially made him furious often no longer seems important. He says this structure has worked because it does not require him to become a different person; it prevents his impulsiveness from dictating the business. His immediate 99-day goal is to create another in-person event. Their annual Hoop Group basketball event has generated a fun, unusually strong network, but it is limited to people who are both highly accomplished and genuinely interested in basketball. He wants a broader IRL event before year-end, despite not yet having a concept. He argues that a decision or idea can take as long as it takes and that he can make the event happen even though a professional planner would say the timeline is too short.

Sam recalls that his previous company, The Hustle, began with events before becoming a newsletter. He organized the first HustleCon in roughly six weeks, beginning work around May 15 for a July 1 event. He charged about $300 and attracted approximately 350 people. Shaan says the event succeeded partly because its name and positioning—scrappy entrepreneurs and “the real deal”—made polish unnecessary. A luxurious or highly produced event would have been off-brand, so the limitations became part of the appeal. They compare this with Burning Man, whose deliberately rough setup changes what attendees expect: people bring their own supplies, build the town, solve problems themselves, and clean up afterward. Shaan says a friend involved with Summit Series viewed that ethos as brilliant event planning because attendees do not expect to be “babied.” Sam says organizing an event feels like running a marathon or giving birth: excitement turns into fear as the date approaches, the day itself becomes a blur, and a week later the organizer is ready to do it again and improve it. Shaan explains that their events are intentionally run out of pocket rather than for profit. They ask what event would be so valuable, fun, and meaningful that they would willingly spend $150,000 to $250,000 to create it. That financial constraint eliminates ideas designed merely to make $100,000, $300,000, or $1 million and pushes them toward distinctive events they genuinely want to attend.

Shaan tells a story about investor Joel Greenblatt. At a talk, Greenblatt placed a jar containing 1,776 jelly beans at the front of the room and asked roughly 100 people to privately write down their estimates. The average estimate was 1,771—only five away from the actual number. He then asked attendees to announce their guesses aloud. Hearing other people changed the estimates dramatically; the average fell to around 900, roughly 50% off. Greenblatt used the experiment as a model of the stock market. Shaan says that intelligent people can often independently analyze a business and estimate its value reasonably well, but they become worse investors when they listen to news reports, analyst commentary, Jim Cramer, and the stock ticker. A falling price gets interpreted as evidence that the business is bad, while a rising price creates fear of missing out. The lesson is to look at the jar, write down an independent estimate, and avoid letting the crowd determine what the underlying business is worth. Shaan adds that even Greenblatt acknowledges how difficult this is, which is why Warren Buffett recommends low-cost index funds. Shaan says he gives the same recommendation even though neither he nor Buffett personally follows it exclusively. The point is not that independent valuation is impossible, but that social influence makes it unusually hard.

Shaan connects the investing story to a personal problem: he is easily influenced and becomes excited by other people’s stories, such as Sam Newhouse’s. After hearing Joe Hudson on an earlier episode, he read The Untethered Soul and focused on its idea that the voice in one’s head should be treated like a roommate. If the roommate says, “You totally screwed that up” or “You suck,” the listener can acknowledge the thought without treating it as the self. Asking “Why am I thinking this?” and “Who am I?” creates distance and may produce insight. Rick expands this into his “five voices in the head” theory, comparing the voices to the characters in Inside Out. One is the critic, like David Goggins: no achievement is enough, and every completed task should have been bigger. The critic serves a purpose by preventing complacency, but too much of it makes life miserable. Another is the mother, a protective and caring voice that wants to slice one’s grapes and keep one safe. That voice is useful in moderation but can cause a person to avoid all meaningful risk. Rick says there are three other voices, and when all five become quiet, what remains is the self. They argue that meditation, sleep, and therapy help because they quiet the noise long enough for someone to discover what they actually want. Shaan’s practical challenge is to ask whether an exciting idea truly belongs to him or whether he is merely copying an influential person.

Shaan describes Edward de Bono’s Six Thinking Hats as a way to prevent discussions from getting trapped in one person’s default perspective. The hats represent different modes, including focusing on facts, being optimistic, and acting as a devil’s advocate. In a meeting, someone can be asked to stop saying why an idea cannot work and instead analyze it as an optimist, or to stop generating wild ideas and temporarily think like a manager concerned with profitability and payroll. Shaan says explicitly naming the mode produces a much better conversation. Rick relates this to Jerry Seinfeld’s idea that creators need two minds. The first is childlike and playful: it grabs a crayon, scribbles, and produces material without worrying whether it is good. Writer’s block often comes from trying to judge the work before creating it, because fear of failure leads to producing nothing. The second mind is the ruthless editor, which arrives later to cut excess words, rearrange material, and apply taste and judgment. Bringing the editor into the brainstorming phase suffocates the brainstorm. Rick and Diego literally made two hats labeled “Rick mode” and “prick mode.” Rick mode means trusting the playful process; prick mode means editing aggressively. They compare this with Warren Buffett’s “too hard pile,” where investments that are neither obvious winners nor obvious losers can be set aside rather than forcing a decision. They also cite Zach Dell’s red and blue notebooks: one for working in the business and one for working on it. Sam shows that he has three notebooks—one for daily reflection, one for ideas, and one for concrete tasks and problem-solving.

Sam describes a daily “fire journal” in which he spends about three minutes recording what he did, something he is grateful for, and an idea or reminder. One entry might capture why he enjoyed reading Aristotle or how bringing help made a trip to San Francisco easier. A second notebook holds ideas from books and other passing thoughts; the third is for the day’s tasks, checklists, and brainstorming solutions. The hosts agree that creators often “write drunk, edit sober,” meaning they generate freely and evaluate later. Rick uses the metaphor of inheriting an old mansion with a beautiful bathtub. When the water is first turned on, brown, muddy water comes out. That is what early creative output feels like: the first freestyle or first page may be embarrassing. Most people turn the water off, but creators who leave it running eventually clear the pipes and produce better work. They use Eminem as an example. Although his “Hi, My Name Is” lyric reportedly emerged within seconds after Dr. Dre played a beat, the hosts say that moment was backed by years of daily practice. Reports about Eminem describe him writing constantly and treating the studio like a workday, arriving around 9 a.m. and leaving around 4 p.m. They also mention Tupac, who said prison made writing difficult because it lacked inspiration and the rapid studio workflow that helped him create. Rick applies the same principle to the podcast: taking three months off would not create a backlog of excellence; returning would be worse. Regular reps keep the creative system warmed up.

Sam tells the story of Sam Newhouse, the founder of Advance Publishing. Born around 1895 into a Jewish family, Newhouse left school at roughly 13 or 14 when his father became too ill to work. After taking a mail-order bookkeeping course, he got a job at 15. The business owner later trusted him with a small local newspaper that generated the modern equivalent of about $800,000 in annual revenue. Newhouse turned it around within six or seven months, received a share of profits and ownership, and eventually borrowed money from relatives to buy the Staten Island Advance. Newhouse’s model was straightforward: newspapers existed primarily to sell advertising, and content should be as good as possible within the company’s constraints while remaining profitable. He controlled costs, bought another newspaper roughly every three years, and grew revenue by approximately 15% to 20% annually for decades. He worked from a briefcase rather than an office, made many deals with handshakes, had no partners or executive team, and personally visited publishers around the country. His children later expanded into higher-prestige properties, buying The New Yorker and Condé Nast publications such as Vanity Fair, Vogue, and GQ. Anna Wintour became part of that editorial strategy, with editors given broad freedom as long as the publications remained profitable. Advance later bought Reddit for $10 million before its public offering and still owns a substantial stake, now worth an estimated $2 billion to $3 billion. The company also owns or has owned properties including Ironman, a mountain-bike event, Turnitin.com, part of Warner Bros. Discovery, and part of Charter Communications. Shaan’s lesson is to know what business you are in, resist pretending to be something more glamorous, and let separate businesses operate independently rather than forcing everything through a centralized back office.

The hosts apply the Newhouse lesson to brand strategy. Sam recalls Jaguar’s rebrand, which attempted to move the company back toward its roots after years as a middling car brand. Historically, Jaguar represented a stylish, masculine, James Bond-like driver and a certain relationship with gasoline and performance. But the rebrand used an androgynous spokesperson and imagery that appeared connected to LGBTQ themes, which the hosts say did not match why Jaguar’s traditional customers bought the brand. Customers responded, in effect, “What is this?” because the campaign no longer reflected the product’s established identity. They then discuss Nike’s stock decline from a peak around $170 to approximately $36, an estimated 80% fall, leaving the company with a market capitalization of about $53 billion against roughly $46 billion in annual revenue. They acknowledge there are multiple business explanations, but focus on a popular brand critique: Nike once represented greatness and excellence. Its advertising often centered on athletes pushing through limits, with the shoe appearing almost incidentally. More recently, the hosts argue, Nike began emphasizing broader body representation and featured people who were not presented as exceptional athletes. They believe that weakened the premium meaning of an athletic brand associated with excellence. The expected response is a return-to-roots campaign: trimming product lines, changing the ad agency, and paying athletes to restore the old identity. The broader recommendation is to understand the customer’s reason for showing up. For My First Million, the hosts say that reason is not simply business advice; listeners enjoy entertaining stories, business “fantasy football,” and inspiration they can carry back into their own unrelated companies. They should therefore stay focused on stories about people doing impressive things rather than chase political or broader topics merely for attention.

Sam introduces a recurring segment called “I Created a Monster / How to Turn Shit Into Gold.” He describes his sister-in-law, Sydney Glander, who is 30, pregnant, due in October, and recently diagnosed with breast cancer. Rather than hide the situation, she began making TikToks that start with the blunt premise, “I’m 30 years old, I’m pregnant, and I have cancer,” followed by updates such as workouts and the day she shaved her head. Some videos receive tens of thousands of views. Sam says she has turned one of the worst combinations of circumstances into a creative project and is also receiving free products from brands such as Kettle & Fire. Rick suggests that she eventually describe herself as an “expecting mom and future cancer survivor,” arguing that public identity labels can make it harder to move beyond an experience one hopes will end. The conversation then shifts to a story about Sam’s wife, who becomes intensely concerned about the state of the house when visitors are coming. After she posted toys for a kindergarten teacher to collect, the teacher arrived with her husband and children. Their son had a habit of hiding in unfamiliar houses for hours, so the husband searched every room, closet, drawer, and space upstairs. Sam’s wife followed him, making excuses about each untidy area, while the search continued until the child was found inside a closet. Sam says she was so traumatized that they barely spoke for 15 minutes afterward. They close with Sam recalling The Hustle’s “zombie email,” sent to subscribers who had never opened an email and framed as a safe opportunity to reveal embarrassing secrets. The hosts treat the episode itself as a similarly candid, humorous reset before promoting Marketing School.