Podcast Summary: This Week in Startups – "If you’re not working 9-9-6, are you working hard enough?" (E2198)

Host: Jason Calacanis
Guest: Alex Wilhelm
Date: October 25, 2025

Episode Overview

This episode dives into the intense work culture of startups—especially the controversial "9-9-6" model (9am–9pm, six days a week)—and juxtaposes it with current tech trends, fraudulent behaviors in business and sports (especially poker and sports betting), and major developments in AI infrastructure. With real-world examples, anecdotes, and the latest news, Jason and Alex dissect the blurry ethics of modern competitiveness and innovation.

Key Discussion Points & Insights

1. The Rise of Fraud in Sports & Gaming

• Insider Trading & Gambling Ethics

  • NBA & Sports Betting: Discussion starts with recent allegations involving misuse of injury status in the NBA—e.g., insider tips about LeBron James’ playing status influencing gambling lines ([00:05], revisited at [22:01]).
    • Jason Calacanis: “People take [injury reports] into account when they’re betting on games... So what happened... is, somebody told their friends, ‘I don't think LeBron's going to play tonight.’... They put action on the games, having that information an hour before the lines change. Is that illegal?” ([00:05]-[00:51], [22:01])
    • Alex Wilhelm: “The injury status, Jason, was sold by allegedly his friend and former LA Lakers coach Damon Jones. Jones... sold the information ahead of time.” ([00:51], [22:51])
    • They argue whether such tips cross into illegality or remain in a "gray area" (insider trading parallels).
    • Jason: “If you’re a trainer or security guard... and someone finds out, then bets on fantasy sports with that info, it’s probably not going to get picked up. Brave new world.” ([01:07], [23:06])
  • Regulation is Fixing, Not Breaking:
    • Both agree rising regulation around sports betting is surfacing old fraud, making things more transparent and opportunities for startups to solve new problems.

• High-Stakes Poker Cheating

  • Recent scandal: High-profile poker games with NBA names and mob involvement; use of high-tech cheating methods: X-ray tables, marked decks, rigged shuffling machines ([06:45]).
    • Alex: “There were a series of games... in a fraudulent manner... involved face cards, high profile NBA people. …The five families famous for crime in New York City were involved as enforcement.” ([06:45]-[07:49])
    • Jason: Explains classic (marked decks, dealers stacking cards) and modern ways of cheating; shares personal anecdotes about exclusive/celebrity games and why trust is everything ([12:54]-[13:21]).
  • Legal vs. Illegal Gambling: Clarified difference between legal, rake-free home games, and illegal games (rake-taking). Also, discusses sports betting and prop bets, with technology now alerting companies to abnormal betting patterns (Polyrouter, Sports Trader) ([18:06]-[19:39]).

Notable Quote

• Jason Calacanis [08:12]: “There is a small potatoes aspect to this if you've got a 20 or $30 million NBA contract. But these rigged games have been around forever.”

2. The "9-9-6" Work Ethic: Startup Grit or Outdated Grind?

• Origins & Current Debate
  • The 9-9-6 model popularized in China (9am–9pm, 6 days/week = 72 hours). Once admired for hustle, now under scrutiny following tragic events at Chinese tech companies, backlash from workers, and China’s 2021 move to officially outlaw the practice ([25:04]-[27:56]).
  • Jason: Recounts how American VCs used to spot dedicated founders by showing up at startups on weekends/nights ([26:01]).
  • Alex: Details the backlash in China—employee deaths, “mini revolts,” and cultural shifts ([27:36]).
• Is It Exploitative or Fair?
  • Jason: Argues it’s a personal choice, ethical if the compensation is fair—stock options, high salaries ([28:40]-[30:01]).
  • Alex: “If you own what you’re working on, you’re less of a salaried worker, more of an owner.” ([31:17])
  • Discusses how “hyper-competitive” roles (NBA stars, Navy SEALs, Olympians) work >72 hours a week.
  • Market forces might naturally reset acceptable work norms; AI, tech, and "woke era" companies sometimes pitch shorter workweeks, but generally lose out to hard-driving startups ([34:12]).

Notable Quotes

• Jason Calacanis [26:36]: “When you get in a dog fight on a business level and you've got a ship product, like there's a huge prize here… People can opt in to work 72 hours a week.”
• Jason [32:49]: “You don't need to be precious about it... It's light work when compared to what humanity was doing a thousand years ago.”

3. AI Tools and Democratizing Creativity

• Showcase: Presh Kumar’s Startup Marketing Video Workflow
  • Demo Segment ([36:56]–[41:41]):
    • Process: Combining ChatGPT (scripting & storyboards), 11 Labs (voiceover), Sora/Suno (music), CapCut (editing).
    • Presh: “It's a simple workflow...We narrowed down to this letter to my younger self concept...I wanted to script it out and storyboard—this is where I used ChatGPT...for the voiceover I used 11 labs, music from Sora.” ([38:24]-[41:26])
    • Jason: “Eventually you'll be able to do this in one LLM or with agents that...do the entire process for you.” ([41:49])
    • Links to the tradition of master storytellers like Ridley Scott, now made accessible to anyone via AI ([43:23]-[44:55]).
• Democratization Insight:
  • AI tools collapse the gap between beginner and master (“amateur to auteur”).
  • “If you did 100 days in a row with these tools... the gap between you and Ridley Scott closes.” ([44:56])

Notable Quote

• Jason Calacanis [44:56]: “Now the distance [between amateur and auteur] is going to be... instead of 10,000 or 20,000 hours, I think it goes down to 100 or a thousand hours.”

4. Tech Markets: Infrastructure Wars in AI

• Anthropic & Google’s Massive TPU Deal
  • News: Anthropic inks a deal for up to 1M Google TPUs for AI training/inference, sidelining their “preferred partnership” with Amazon ([48:02]).
  • What’s a TPU? ASICs (application-specific chips) for machine learning—faster, more efficient for neural nets.
  • Strategic Implications:
    • Gemini (Google), Anthropic (Claude), Meta (Llama), OpenAI, Grok, Mistral—AI competition described as “strange bedfellows” as some platforms are both competitors and partners ([51:07]-[51:48]).
    • Those with “money printing” cloud businesses (Meta, Google) can outspend smaller AI startups in infrastructure, possibly gaining long-term advantage ([51:48]).
    • Historical analogy to Dropbox, 37signals, and the merits/drawbacks of owning hardware vs. renting cloud capacity ([53:52]-[58:01]).
    • Oracle’s aggressive pricing to cut cloud infrastructure bills highlights the competitive dynamics ([59:07]-[60:29]).

Notable Quote

• Jason Calacanis [51:49]: “Meta and Google can build infrastructure at a pace that the other four have to go raise money for.”

Notable Quotes & Memorable Moments

• Jason Calacanis [00:05]: “If you drama that in, you've got your bet locked in at that other bet. So is that illegal?”
• Alex Wilhelm [09:33]: “Curlicues that are missing, but just small things that would tell you... this is an ace. […] Giving you a huge edge.”
• Jason Calacanis [26:36]: “We got into this life work balance nonsense, unions, people, you know, wanting to see their families, all this craziness.”
• Presh Kumar [38:24]: “A letter to my younger self concept… 100 year old grandpa writes a letter to his younger self… then using ChatGPT, I basically prompted it and got a whole structure out of it.”
• Jason Calacanis [44:56]: “The gap between the auteur and the amateur is closing.”
• Jason Calacanis [51:49]: “Meta and Google can build infrastructure at a pace that the others cannot.”

Timestamps for Important Segments

| Section | MM:SS | Notes | |---------------------------|-------------------------|-----------------------------------------------------| | NBA/Basketball Sports Betting Scandal | 00:05-01:07, 22:01-23:06 | Gray areas of insider trading in sports betting | | Poker Cheating/Scandal | 06:45-16:09 | High-stakes games, cheating methods, mob rumors | | Fantasy Sports/Prop Bets & Detection | 17:20-19:39 | AI companies flagging suspicious betting patterns | | 9-9-6 Work Culture | 25:04-34:12 | China’s 72-hour week, U.S. attitudes, legal/ethical | | Equity/Fair Comp in 9-9-6 | 31:17-32:49 | What’s fair for startup employees | | Press Kumar’s AI Workflow Demo | 36:56-41:49 | End-to-end ad concept creation with AI tools | | Anthropic-Google AI/TPU Deal | 48:02-53:52 | Cloud infrastructure dynamics | | 37signals Drops AWS—DIY Infrastructure | 53:52-58:01 | Cost-benefit of in-house vs. cloud infrastructure |

Tone & Style

Authentic, sometimes irreverent or sarcastic, blending personal experience with industry analysis. Jason is blunt, provocative, and anecdotal; Alex is methodical with a subtle wit and global context.

Final Thoughts

• The startup hustle is as fierce as ever—whether in work ethic ("9-9-6") or the race for cloud infrastructure dominance.
• Regulation is making fraud more visible, and technology (especially AI) is both a target for hustlers and a tool for transparency.
• AI and modern tools are rapidly closing the skills gap in creative industries.
• Partnership strategies and infrastructure choices are pivotal in the AI arms race.

Essential Takeaway:
“Work harder than the competition, but be smart about incentives and infrastructure—because in modern startups, the old rules and new tech collide daily.”