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Colossus (Invest Like the Best / Business Breakdowns)Podcast21 Sep 2021Source: joincolossus.comHost: Patrick O'Shaughnessy

David Fialkow - Paint Outside the Lines - [Invest Like the Best, EP. 243]

In plain words

This piece is about investor David Fialkow's approach to picking founders: he cares more about whether they truly love their product than the business model. He believes great founders love their product so much they ignore criticism, and that passion is key. Examples include Boston Beer Company (founder turned beer ingredients into a hit seltzer, hitting $1B in 3 years), Ro Health (got a former Uber exec on its board through Fialkow's network), and the Oscar-winning documentary 'Icarus' (director pivoted after failure and succeeded).

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David Fialkow, co-founder of General Catalyst, shared his unique investment philosophy on the Invest Like the Best podcast. His core view: great founders must possess a passion for their product and creativity, rather than focusing solely on business models; the ability to effectively convene a netw

~12 min full read · 9 sections
Deep Analysis

David Fialkow - Paint Outside the Lines - [Invest Like the Best, EP. 243]

At a Glance

David Fialkow, co-founder of General Catalyst, wears multiple hats as an investor, philanthropist, and Oscar-winning producer (2018 documentary Icarus). The central theme of this episode: investing should "paint outside the lines" — a founder's passion and creativity matter far more than the business model. Fialkow's core thesis: great founders must "love the product above all else." This love makes them deaf to criticism, blind to obstacles, and naturally capable of pivoting through failure — making it the rarest and most irreplaceable trait in investing.


Theme 1: The "Four Elements" of Founder Screening — Passion as the First Filter

David Fialkow argues that when evaluating early-stage founders, business models and financial metrics are far less important than four key traits.

Fialkow proposes a "mental checklist":

1. Passion for the Product: The founder is willing to "walk through walls" to get investors to use the product, believing the world needs their product "more than it needs oxygen."

2. Sales Ability: The ability to tell a compelling story — clearly conveying the importance of the product and its mission.

3. Humility: A willingness to listen to others (though not necessarily follow their advice), leaving room for a pivot — "venture capital returns primarily come from pivots."

4. True North: A sense of mission and moral intuition — "Adversity does not teach character. It reveals it."

Counterexample: Fialkow points out that when a founder says, "I want to start a startup, and I see your industry looks promising," it indicates they do not love the product itself but are merely focused on the business opportunity — such people "will never reach the promised land."

Key Case: Sam Adams founder Jim Koch. When the beer business declined and was threatened by tequila, Koch did not abandon beer. Instead, he used beer malt to invent Truly hard seltzer — "going from zero to $1 billion in three years, while the beer business took 40 years to reach $1 billion." Fialkow sees this as the ultimate expression of "passion for the product": Koch never said "beer failed," but rather "it is innovating."


Theme 2: The Core Competitiveness of Investment Institutions — "Maker Mentality" and "Convening Power"

Fialkow believes that the essence of VC is not "investing" but "making" — using empathy, a sense of security, and a cross-disciplinary network to help founders.

Three layers of meaning in the "Maker Mentality":

  • Empathy and a sense of security: Fialkow spends a significant amount of time talking with founders about their personal lives (family, spouses, partnerships) rather than the business itself — "Be safe. Be somebody that people want to talk to."
  • Protecting founders from harm by other investors: For example, supporting founders in monetizing part of their equity through the secondary market — "Someone gives you money, do you lose motivation? No. So why would you think founders would?"
  • Self-awareness: Fialkow admits he "knows nothing" about cloud computing and once rambled about Barracuda to Data founder Austin McCord — but he knew to bring in Paul Sagan (former CEO of Akamai) and Steve Herrod (former CTO of VMware) to provide technical assistance.

"Convening Power" is Fialkow's core methodology:

  • Regularly bringing together founders, athletes, filmmakers, academics, and LPs to create "right-brain cross-pollination"
  • Case in point: Ro Health founder Zach met former Uber legal head Tony West at Fialkow's gathering, and West subsequently joined Ro's board — "This wasn't a coincidence; I arranged it intentionally"
  • Effect: Founders no longer feel "they are strange," gain a cross-industry safety net, and avoid the "echo chamber effect"

Key turning point in institution building: Fialkow acknowledges that GC has always been strong at "making good investments" but needed help in "building the institution" — hence bringing in Ken Chenault (former CEO of American Express) to help scale. "We didn't need his help raising funds — top-tier VCs raise funds easily — we needed his help maintaining the quality of service to founders."


Theme 3: Icarus — A Perfect Replication of VC Methodology in Filmmaking

Fialkow uses the production process of Icarus to demonstrate the universality of "founder support" beyond the tech sector.

Story Arc:

  • Director Bryan Fogel initially wanted to make an entertainment film about "whether he could cycle better after doping" — the film failed (his performance actually worsened after doping)
  • Fogel was "curled up on the floor like a founder" in Geneva — Fialkow and Jim Schwartz said: "We're VCs, this happens all the time. How do we pivot?"
  • They asked Fogel: "If you could do one extraordinary thing, what would it be?" Fogel replied: "Go to Moscow to find Grigory Rodchenkov and figure out how Russia helped athletes cheat at the Olympics."
  • Fialkow's judgment: "This pivot sounds good. The last film is behind us. We'll give you a Series A." They added funding.

Key Support:

  • Provided "air cover" and "encouragement and nutrition"
  • When Russia threatened to kill Rodchenkov, Fialkow told Fogel: "Hold on, we'll help you get through this"
  • Jim Schwartz found top-tier lawyers to handle U.S. legal system issues

Luck Factor:

  • The film's Sundance premiere coincided with Trump's inauguration day — the political climate generated enormous attention for the film
  • Sundance director Carrie Putnam made an exception to allow the film to be uploaded at 3 a.m. (the usual deadline was 9 p.m. the night before) — Fialkow called her "a great VC, protecting her founder"

Fialkow's Summary: "40% of returns come from the macro market environment. You can build the best company, but in a bad market, valuations will be low. How lucky were we — the film's premiere day happened to be Trump's inauguration day."


Theme 4: Current Areas of Focus — Diverse Teams and Public Influence

Fialkow believes that VC firms now have both the responsibility and the ability to influence public policy, an unprecedented development.

Two specific actions:

1. OneTen Initiative: In collaboration with Ken Chenault (former CEO of American Express) and Ken Frazier (former CEO of Merck), the goal is to create 1 million "family-sustaining wage" jobs for Black families within 10 years — "not everyone has to go to college to support a family."

2. Voting Rights: Leveraging a network of CEO relationships to advance voting rights protections.

Fialkow's logic: "Our generation of tech leaders has the 'throw weight' to truly influence people — because people need our business and trust us. Instead of hitting them with a stick, use a carrot. They need us, and we can help them."

Specific networking examples:

  • Gina Raimondo (former Governor of Rhode Island, now Secretary of Commerce) — "She is responsible for implementing a large number of infrastructure projects. Who is better suited than a former VC-turned-governor?"
  • Marty Walsh (Secretary of Labor, former Mayor of Boston) — "A tough guy, but he can bring people together to get things done."
  • Mark Warner (Chairman of the Senate Intelligence Committee) — Collaborating with VC and tech companies in the cybersecurity space.

Theme 5: The Foundation of a Great Story – Not Skill, but "Unshakable Conviction"

Fialkow believes that great storytellers are not necessarily charismatic, but they are "so convinced that they think you're an idiot for not joining in."

Three levels:

1. They are not "selling" – they believe so deeply that they "can't imagine why you wouldn't invest or use it"

2. They are not persuading you to join – "they think you're an idiot for not joining"

3. This unshakable conviction makes them "blinded by obstacles" – and that's a good thing

Fialkow's self-positioning: "I myself am very mediocre. But I have the ability to convene, to gather extraordinary people around me. That's why I can accomplish so many things."


Mentioned Positions

Position Guest Sentiment Key Data
Boston Beer Company (Sam Adams) Positive case (Fialkow serves on the board) Truly hard seltzer: from zero to $1 billion in 3 years; beer business took 40 years to reach $1 billion
Data (Austin McCord) Invested, highly endorsed Founder is 28 years old, started from a basement; Fialkow admits he does not understand the technology and brought in Paul Sagan and Steve Herrod for support
Ro Health (Zach) Invested, highly endorsed Supported by multiple General Catalyst partners; introduced Tony West to join the board through Fialkow's gatherings
Icarus (Bryan Fogel) Invested (film project) Won the Academy Award for Best Documentary; Fogel successfully pivoted after his first attempt failed

Judgments Worth Remembering

1. "Adversity does not teach character. It reveals it." (David Fialkow) — Adversity does not shape character; it reveals it. This is Fialkow's core criterion for evaluating a founder's "true north": when bad things happen, they rely on instinct to do the right thing, not on written rules.

2. "40% of every return is what the market's doing at the top." (David Fialkow) — 40% of returns come from the broader market environment. The best companies are undervalued in a bad market. This is Fialkow's candid acknowledgment of the role luck played in Icarus's success.

3. "The word 'investor' doesn't work in the venture business. We're builders. We're makers." (David Fialkow) — The essence of VC is not investing, but making. Fialkow draws an analogy from his filmmaking background: providing empathy, a sense of security, and cross-domain networks, rather than cold capital.

4. "If you paint between the lines, you'll never be an outlier." (David Fialkow) — Those who "paint within the lines" pursue "gold stars" (Ivy League → Goldman Sachs → perfect resume), but fear risk and fear blemishes. True outliers must become comfortable with failure and embarrassment.

5. Founder "Four-Factor" Screening Framework (David Fialkow): Love for the product > Sales/storytelling ability > Humility (leaving room for pivots) > True north (moral intuition). The first factor, "love for the product," is Fialkow's most distinctive criterion — a founder should "love the product more than oxygen," rather than focusing on the business opportunity.

6. "No one is spared." (David Fialkow) — No one is spared from bad things in life (marriage, children, friendships, business). The key is the ability to say "help me" and to have empathetic people around. This is the core of GC's culture: maintaining empathy for the founder's journey.

7. The essence of a good story is not technique, but "unshakable conviction" (David Fialkow) — Great founders are not "selling" a product; they think "you're an idiot for not joining." This unshakable conviction blinds them to obstacles, which paradoxically becomes an advantage.

8. "Convening Power" as an Investment Methodology (David Fialkow) — Fialkow's core strength is not judging business models, but "gathering extraordinary people" and creating cross-domain connections. Ro Health bringing Tony West onto the board, and Data's founder gaining a technical mentor — all achieved through carefully orchestrated gatherings.