This is about following trends instead of guessing. Howard Lindzon says FinTech is getting weird, but people love it—they know they should save but still trade on Robinhood and buy car shares. He likes Rally Road (sells car shares, sells out fast), Robinhood (free trading app, mocked but popular), and Apple, Nike, Lululemon (mixing fashion and tech). His advice: don't fight human nature; follow smart investors.
At a Glance Howard Lindzon, in his appearance on the Invest Like the Best podcast, shared his trend-following investment philosophy, emphasizing a focus on "what is happening" rather than "what might happen." He likens himself to the Larry David of the investment world, with his style influenced by
Howard Lindzon is an early-stage investor and co-founder of StockTwits, who describes himself as "the Larry David of investing." The central theme of this episode: Trend-following investment philosophy—focusing on "what is happening" rather than "what might happen." The most impactful judgment in the entire episode: "FinTech is diverging from human nature, and denying human nature is a foolish mistake" (Howard Lindzon)—people know they should diversify their asset allocation, yet they insist on buying fractions of sports cars and trading frequently on Robinhood. Investing should align with this "irrationality."
Howard Lindzon argues that the essence of trend following is "staying close to the trend creators, not creating the trend yourself."
He explains this with two natural analogies:
Key Mechanism: Twitter and social networks form a "global social peloton"—"If you know who to follow and stay behind these smart people, you are a trend follower. You don't need to create the trend; just get close to the trend creators, and the money will come."
Falsification Condition: When Lindzon can no longer find "great white sharks to follow" (i.e., directions that top VCs he trusts, such as Fred Wilson and Chris Dixon, are focusing on), his strategy will fail.
Lindzon believes Fred Wilson is a top-tier investor because he "gives everything away for free"—his blog, term sheets, and network, holding nothing back.
In 2005–2006, Lindzon was a hedge fund manager with no knowledge of the internet. He Googled "term sheet," found Fred Wilson’s blog, and discovered a complete term sheet template. "I thought, how could these idiots give this away for free?" He copied and pasted it, used the template to invest in Golf Now (the golf version of OpenTable), which was acquired by Comcast two years later.
More critical was the network: Wilson gave Lindzon a list of phone numbers, including Brad Feld, Roger Ehrenberg, and others. "I made 11 calls, and 10 people put in money." Lindzon launched Wallstrip (YouTube’s CNBC) with $600,000 and sold it to CBS seven months later.
Lindzon’s self-assessment: "Fred picked someone with zero experience like me, and we still sold to CBS—that’s legendary. He combines an MIT-level intellect with an artist’s eye, and he’s stayed in his weight class for years without getting overextended."
Reader note: This is a narrative from the position holder’s perspective—Lindzon uses his own success story to argue for the effectiveness of a "follow the right person" strategy, but does not address survivorship bias.
Lindzon argues that "weird" implies uniqueness and a slight sense of discomfort, which in investing often corresponds to mispricing.
"If you walk into a Chelsea gallery or browse art on Broadway—I've always felt, because I was shy as a kid, that I was weird. Fantasizing at age 8 about being on Johnny Carson's show—that's weird enough. But being weird without knowing it was an advantage for a time; now being called weird is a badge of honor."
Investment Application: When Lindzon invested in Rally Road (a fractional trading platform for classic cars), he had no interest in cars. "The team matters more than anything. They explained the entire industry to me in 10 minutes—domain expertise is key. I don't care about market size because I'm small. But they have scars; they understand this industry."
Lindzon believes fractionalization is the core trend in FinTech, with Robinhood and Rally Road being just the beginning.
Data Support: Lindzon notes that when Robinhood was valued at around $6 billion, his own money was still at Schwab—"This shows there's still massive room for disruption."
Lindzon cites Fred Wilson's framework to differentiate FinTech in China and the U.S.:
| Dimension | China (Planet Model) | U.S. (Constellation Model) |
|---|---|---|
| Dominant Players | Alibaba, Tencent, Baidu | No single platform dominates |
| Payment Infrastructure | Skipped Visa/MasterCard | Still pays tolls to the two major "railroads" |
| User Behavior | Centralized on one platform | Uses 30+ financial apps (Venmo, Square Cash, Robinhood, StockTwits, etc.) |
Core Judgment: "You can't convince young people to put all their money under one roof. They use 30 financial apps. Schwab wants to lock in customers, but this is Jurassic Park—the walls will eventually be broken down."
Lindzon believes the golden age of social media is over, and Trump "won" Twitter with 140 characters.
"Like playing a pinball machine as a kid—there's always one person who figures out the machine and gets the high score. Once he gets that high score, the machine is done—time to move on to another one. Trump is that person. He won Twitter. Unless Twitter shrinks or acquires another company, the end of its price trend is its terminal outcome."
Investment Implications: Lindzon likes media but is unwilling to invest LP capital in it—"Content is not scalable. You create a piece of content, it comes to life, but it dies very quickly."
Lindzon introduces the concept of "Fashionology," arguing that Apple, Nike, and Lululemon are merging fashion with technology.
"I buy Apple products at Lululemon stores and Lululemon products at the Apple Store. Oakley was the first to do this—with Bluetooth sunglasses—but sold too early. Now Lulu and Nike are the new-generation Oakley, and there will be hundreds more in the future."
Analogy: Lindzon cites The Tipping Point, arguing that Soho remains the starting point for trends. "I scan the list of new highs every day. If a company resonates with me, I dig deeper. That's the starting point in the public market."
| Position | Guest Stance | Key Data |
|---|---|---|
| Rally Road | Bullish (seed round investment) | Vehicle "IPO" sold out in 3 minutes; a $14,000 Ford Mustang also sold out quickly |
| Robinhood | Bullish (seed round investment) | Valuation ~$6B (2018); "commission-free trading, software-driven broker-dealer" |
| StockTwits | Bullish (founder/operating) | 10 years of independent operation; "A Larry David-style company—we did everything to mess it up, but it keeps getting stronger" |
| Golf Now | Exited (acquired by Comcast) | The OpenTable of golf; Lindzon invested using Fred Wilson's term sheet template |
| Wallstrip | Exited (sold to CBS after 7 months) | Seed round $600K (from Fred Wilson's phone list); CNBC on YouTube |
| The Grip | Exited (QVC Hall of Fame product) | Lindzon's first angel investment; started with a $25K loan from his mother |
| Neutral to bearish | "Trump won Twitter; the end of the price trend is the endgame" | |
| Apple | Bullish | "One of the three giants of fashion tech" |
| Nike | Bullish | "One of the three giants of fashion tech" |
| Lululemon | Bullish | "One of the three giants of fashion tech"; Lindzon has been watching it for 8 years |
| Oakley | Neutral (sold to Luxottica) | "The first company to merge fashion and tech, sold too early" |
| Vanguard | Critical | "Has the technology but doesn't offer consumers fragmented choices, which makes them evil" |
| Schwab | Critical | "I hate Schwab—I can't even see my account within 30 seconds of logging in" |
1. "FinTech is deviating from human nature, and denying human nature is a foolish mistake" (Howard Lindzon) — People know they should diversify, yet they insist on buying fractions of sports cars and trading frequently on Robinhood. Investment should accommodate this "irrationality," not try to correct it.
2. "Once Trump won Twitter, that machine was broken" (Howard Lindzon) — An analogy to a pinball machine: someone will eventually figure out the machine and get the highest score, after which the machine is obsolete. Trump "won" Twitter with 140 characters; unless Twitter undergoes a complete transformation, the end of the price trend is the final outcome.
3. "Fractionalization gives me hope of punishing the bad guys" (Howard Lindzon) — S&P 500 index funds are forced to buy "bad companies" like Wells Fargo, but fractionalization allows investors to precisely avoid them. Lindzon believes Vanguard has the technology but does not offer fractionalization options, "which makes them evil."
4. "Fred Wilson only got interested when Bitcoin was at $1,000 — that's my entry point" (Howard Lindzon) — The core of trend following: wait for top VCs to confirm the direction before entering, acting as the pilot fish under the shark, not charging ahead.
5. "If a founder calls me asking about the news, I'd say: What does that have to do with your next 10 customers?" (Howard Lindzon) — In early-stage investing, founders should focus on product and customers, not macro narratives. Lindzon does not care about market size; "great companies will find their own market."
6. "Now it's time to beat the banker and embrace the designer" (Howard Lindzon) — In the early days, it was "beat the banker and embrace the developer." Now, UI/UX is almost as important as engineering. Founders must have an engineering partner, "otherwise you're the sucker."
7. "Fashionology is the next big trend" (Howard Lindzon) — Apple, Nike, and Lululemon are three companies merging fashion and technology. Oakley was the first to do this but sold too early; there will be hundreds of similar companies in the future.
8. "My investment premise is: if Fred Wilson and Chris Dixon aren't talking about it, then it's a penny stock" (Howard Lindzon) — As a small investor, do not touch areas that top VCs have not yet focused on. This is the operational rule of the "shark and pilot fish" strategy.