How to find your arbitrage (from the guy who’s done it 3x)
How to find your arbitrage (from the guy who’s done it 3x)
YouTube2 hr 5 min
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Note: AI-generated summary based on third-party content. Not financial advice. Read more.
Quick Insights
  • Consider the theme of AI-enabled dynamic-pricing software for businesses with limited capacity, such as restaurants and venues; the opportunity is compelling, but no specific investable company or ticker was identified.
  • Treat PLUG, QQQ, SPY, and UBER as lacking actionable recommendations here: the discussion provided no current trade view, price target, or timeframe for them.
  • Avoid treating Strange House, the vineyard, or Alinea’s historical returns as current investment opportunities; no public investment or expected return was specified.
Detailed Analysis

Plug Power (PLUG)

  • Nick recalled that he and a business partner held a large short position in Plug Power while they were traders in the 1990s or early 2000s.
  • The story was used to illustrate the stress of taking risk, not to make a current assessment of the company.

Takeaways

  • The short position is a historical anecdote, not a current recommendation. The transcript gives no present-day view, price target, or investment timeline for PLUG.

QQQ and SPY ETFs

  • Nick described using trades in the Nasdaq-100 ETF (QQQ) and the S&P 500 ETF (SPY) as part of a historical arbitrage strategy.
  • His firm sought to exploit short-lived pricing differences between ETF trades in New York and related futures trades in Chicago, using faster communication to act before the price gap closed.

Takeaways

  • The discussion describes a specialized, historical trading strategy—not a recommendation to buy or sell QQQ or SPY.
  • Nick emphasized that arbitrage opportunities can shrink as competitors catch on and trading windows close. The strategy he described also required capital, technical setup, and regulatory approval.

Uber (UBER)

  • Nick discussed Uber’s surge pricing as a way to encourage more drivers to work when demand rises.
  • He argued that the underlying idea—adjusting prices to bring supply and demand into balance—was sound, but that the term “surge pricing” made the policy sound like price gouging.
  • He related this to his belief that time- and location-based businesses should adjust prices more dynamically.

Takeaways

  • The conversation highlights dynamic pricing as a business model and operational tool, not a specific valuation or stock recommendation for Uber.
  • Nick’s comments point to a communication risk: even a useful pricing approach can face customer or public backlash if it is framed poorly.

Talk Software and Dynamic Pricing

  • Nick said his software company, Talk, helped restaurants understand who their customers were and manage reservations and pricing. He said the company was eventually sold for hundreds of millions of dollars; the transcript also refers to its sale to Squarespace.
  • He argued that restaurants often price the same seat identically even though demand varies by day and time. In his view, reservations and table availability could be priced more intelligently.
  • He expressed strong conviction that localized, time-based dynamic pricing for businesses with limited time slots could become an enormous business, saying he believed someone could build a company worth hundreds of billions of dollars.
  • He suggested that AI could make these pricing tools easier for businesses to use.

Takeaways

  • The investment theme is software that helps businesses set prices and manage capacity based on time, location, and demand.
  • Nick’s “hundreds of billions” statement is his conviction about the opportunity, not a stated company valuation or forecast. The transcript does not identify a specific company to invest in.

Restaurant Businesses and Alinea Group

  • Nick described building Alinea and its restaurant group as both a creative venture and a business. He said Alinea’s first year generated about $5 million in sales and a 7–8% profit margin; at its peak, it generated more than $20 million in annual sales with margins of roughly 18–20%.
  • He said the group’s investors received quarterly distributions and, when the business was sold, received about 8 times their initial investment from the sale. He characterized the overall return, including distributions, as roughly 27–28 times the initial investment.
  • He credited business systems—including software, reservation management, and food-cost tracking—with helping improve performance. He contrasted the economics of well-run restaurant operations with the common perception that restaurants inevitably earn very low margins.

Takeaways

  • The example suggests that restaurant returns can depend heavily on operational discipline, customer experience, pricing, and cost management.
  • Alinea’s results are a specific historical outcome, not evidence that restaurants generally achieve similar margins or returns. The transcript does not offer a current investment opportunity in the group.

Vineyard and Wine-Bar Projects

  • Nick said he had bought property in Napa and was learning about agriculture, irrigation, and grape growing. He described building a wine bar and planting grapes, while acknowledging that he was not an experienced grower.
  • He said the grapes would not be good until he was 70—he was 58 at the time of the conversation—underscoring the long time horizon he expected for the vineyard.
  • He also noted that grape prices and the wine business move in cycles, and that vineyard owners should not assume prices will always rise.

Takeaways

  • The vineyard discussion illustrates a long-horizon, hands-on investment with potentially slow development and exposure to industry cycles.
  • The transcript provides no expected returns or recommendation to buy vineyard property.

Strange House Immersive Experience

  • Nick described a proposed immersive magic and entertainment venue called Strange House, planned for a 90,000-square-foot space beneath Wall Street.
  • The concept combines close-up magic, theatrical environments, and an emphasis on human connection. Nick said it would be expensive to build and difficult to test at small scale.
  • He said the project needed to support about $20 million in gross revenue to work, using an approximately $120 ticket as part of the underlying business-case discussion.
  • At the time of the conversation, the project was still being developed and faced real-estate negotiations and the challenge of proving an unconventional concept.

Takeaways

  • This is a speculative entertainment-business opportunity, not an available public-market investment identified in the transcript.
  • The key risks mentioned are the high build cost, dependence on a large-scale venue, lack of direct comparables, and uncertainty about whether the concept can be executed and attract enough customers.

Other Company and Trading-Firm Mentions

  • Jane Street was described as an exceptionally capable competitor in an earlier trading strategy. Nick praised its talent and independence but gave no investment view; it is a private firm.
  • Goldman Sachs, Société Générale, and Merrill Lynch were mentioned as financial firms he considered working for or as market participants. The transcript offers no investment thesis on them.
  • HubSpot was mentioned in a promotional context for a free database about successful people. No investment view was expressed.
  • Groupon was mentioned in connection with former CEO Andrew Mason’s departure, and Squarespace in connection with Talk’s sale. The transcript offers no stock analysis of either company.

Takeaways

  • These references are background or business anecdotes, not stock recommendations. No price targets, ratings, or current outlooks were provided for these companies.
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Video Description
*Database on how long it takes to become a millionaire:* https://clickhubspot.com/j87x Episode 876: Shaan Puri ( https://x.com/ShaanVP ) sits down with Nick Kokonas ( https://x.com/nickkokonas ) to talk about finding arbitrages and how to win an many different games. — Show Notes: (0:00) Intro (9:45) How I Became a Trader With $60K (18:15) Surviving Day 1 of Anything (20:35) The Comfort Trap (23:50) Finding Your Arb (32:00) No Boats. No Women. No Drugs. (34:55) Showing Up (43:15) Everything Is an Arbitrage (47:55) Greatness (55:55) Working Backwards (1:03:40) The Magic of Alinea (1:10:35) Controlling Attention (1:19:10) Remixing Old Mechanics — Links: • Alinea – https://www.alinearestaurant.com/ • Tock – https://www.exploretock.com/ — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Shaan uses Mercury across all of his companies. you can too: http://mercury.com/ Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /
About My First Million
My First Million

My First Million

By @myfirstmillionpod

two guys, talking about business. we've done it (sold our companies), and now we talk about new ideas, opportunities, and investments. hosted by Shaan Puri & Sam Parr -- produced by Hubspot. sometimes we bring on guests ranging from billionaires to stay at home moms who've got side hustles that are bringing in $10k a month. we like to have fun, and talk about business stuff.