"Sara's List" Update: 12 Startups Where Stock Grants Will Make You A Millionaire

Episode Summary

Executive Summary: The episode highlights two unusual wealth-building stories: Amit Agarwal, a one-man Google Workspace plugin business in India reportedly generating $10M-$30M annually, and Carl Allen, who sold a trash-bag company then pursued treasure hunting and island ownership. It then revisits the hosts’ “Sarah’s List,” showing that bets on strong private tech companies and equity compensation can produce massive gains, while emphasizing how exponential growth often looks “too late” until it isn’t.

Main Topics: Amit Agarwal’s one-person plugin empire (Priority: 5/5): The hosts discuss a rare case of a solo founder in India building a highly lucrative business by making simple, useful Google Docs/Drive/Gmail plugins and selling both subscriptions and enterprise custom work. Known well vs. well known (Priority: 4/5): The conversation reflects on content creation as a way to be recognized for one’s thinking, so people tag and share relevant ideas and opportunities directly with you. Carl Allen’s post-exit life of treasure hunting (Priority: 5/5): After selling a trash-bag manufacturing business, Carl Allen buys a Bahamas island and dedicates himself to yachting, exploration, philanthropy, and searching for underwater treasure. Childlike ambition and taking more joy/risk (Priority: 4/5): The hosts argue that many adults become too cautious and practical, and that a healthier life philosophy is to preserve curiosity, play, and the willingness to do “sick” things that would impress your younger self. Sarah’s List revisited (Priority: 5/5): They review a prior list of 12 companies they believed could generate million-dollar equity outcomes for employees, and compare prior valuations with current ones to judge how the picks performed. Exponential startup growth and perceived lateness (Priority: 5/5): The hosts stress that high-growth companies can scale far beyond what seems reasonable, and that even seemingly mature startups can still multiply many times over.

Key Arguments: Useful, niche software can become extraordinarily valuable even when it solves small workflow problems. Building content can create durable reputation value by making people think of and send opportunities to you. A life optimized only for responsibility can become too conservative; many people need more play, adventure, and risk. Private-market startup valuations can look absurd at first, but exponential growth can justify outcomes that seem impossible early on. Employee equity at the right company can be a practical path to millionaire status without founding a company or becoming executive. The apparent “lateness” of an investment often reflects linear thinking; truly strong businesses can continue compounding for years. Choosing companies with real product-market fit and strong growth is more important than trying to predict the absolute ceiling exactly.

Data Points: Amit Agarwal annual income: $10M-$25M safe estimate; possibly $15M-$30M - Estimated revenue from Google Docs/Drive/Gmail plugins and custom enterprise work Mail merge plugin downloads: 7.5 million - Amit Agarwal’s Gmail mail-merge plugin Mail merge plugin paid conversion assumption: 5% - Used by the hosts to estimate revenue from free users converting to paid tiers Mail merge plugin AR estimate: $1.5 million ARR - Derived estimate from 7.5 million downloads and 5% conversion Document Studio pricing: $79/year - One of Agarwal’s Google Sheets/document automation products Document Studio downloads: 6 million - Usage scale cited for Agarwal’s product Notification app pricing: $49/year - Another plugin in Agarwal’s portfolio Notification app downloads: 10 million - Usage scale cited for Agarwal’s product YouTube app downloads: 8 million - Another plugin in Agarwal’s portfolio Carl Allen sold Heritage Bag for: $300M-$400M - Sale of his trash-bag manufacturing business to a private-equity buyer Heritage Bag employees: 800 - Scale of the trash-bag company Allen eventually owned Sarah’s List companies: 12 - The set of startup bets they originally discussed Figma valuation at original discussion: $2B - Known valuation when it appeared on Sarah’s List Figma acquisition price: $20B - Adobe acquisition announced later, cited as a 10x outcome Flexport valuation change: $3B to $8B - Performance since the original discussion Anduril valuation change: $4.6B to $6.6B - Performance since the original discussion Replit valuation change: $200M to $800M+ - Host says it likely trades above $800M on private secondary markets Airtable valuation change: $2B to $11B - Performance since the original discussion Rippling valuation change: $6B to $11B - Performance since the original discussion OpenStore valuation change: $250M to $750M - Performance since the original discussion Fair valuation change: $7B to $12.5B - Performance since the original discussion NextHealth valuation change: $400M to $1B - Performance since the original discussion OneTrust valuation change: $2.7B to $5.3B - Performance since the original discussion Figma revenue 2018: $4.1M - Publicly cited growth trajectory after the company began charging customers Figma revenue 2019: $23M - Publicly cited growth trajectory Figma revenue 2020: $77M - Publicly cited growth trajectory Figma revenue 2021: $100M - Publicly cited growth trajectory Figma 2022 goal: $450M - Hosts said the company was on pace to hit it India tax return filing rate (2020): 6% - Mentioned in discussion about taxes and wealth in India

Pivotal Quotes: "My goal is to be known well, which means people know you really well." — Sean: On why creating content can be valuable even without fame "Million dollars isn’t cool. You know what’s cool? A billion dollars." — Sean: Transitioning into the Carl Allen story and the scale of his wealth "The risk is not that they're playing life too risky. It's that they're playing life way too safe." — Sean: Argument for more childlike curiosity, fun, and adventure

Implications: Listeners are encouraged to notice overlooked wealth paths: niche software, startup equity, and unconventional post-exit pursuits. The episode suggests that compounding, not linear thinking, explains many “impossible” outcomes and that life decisions should balance prudence with ambition and fun.