← Back to list
Colossus (Invest Like the Best / Business Breakdowns)Podcast30 Mar 2021Source: joincolossus.comHost: Patrick O'Shaughnessy

Kanyi Maqubela - Dawn of the 21st Century - [Invest Like the Best, EP. 219]

In plain words

This interview covers investor Kanyi Maqubela's fresh take on early-stage investing. He says seed-stage risk doesn't decrease gradually but jumps suddenly, like Clubhouse booming during lockdowns. He values founders' unique insights (fresh market descriptions) over experience or passion. He's bullish on supply chains and the creator economy, mentioning Cloud Trucks (helps truck drivers start businesses) and Catch (designs social security for freelancers). He also says VCs' biggest value is being a 'mirror' for founders and giving a second 'yes' when others doubt.

AI SummaryAI-generated · may contain errors · verify against the original

Kanyi Maqubela (Co-founder of Kindred Ventures) discussed in the program the parallels between the current era and the "Roaring Twenties" of the last century, arguing that the 2020s are undergoing similar technological and infrastructure transformations. The core thesis is that the risk curve in see

~11 min full read · 10 sections
Deep Analysis

Kanyi Maqubela - Dawn of the 21st Century - [Invest Like the Best, EP. 219]

At a Glance

Kanyi Maqubela (co-founder of Kindred Ventures) discusses the parallels between the current era and the "Roaring Twenties" of the last century, arguing that the 2020s are undergoing similar technological and infrastructure transformations. The core thesis is that the risk curve in seed-stage investing is misunderstood: early-stage investing is not a linear high-risk path but involves significant divergence, requiring a focus on founders' long-term traits (such as adaptability and domain insight). Key takeaways include that supply chain infrastructure is being reshaped, and crypto and NFTs will impact multiple industries; the author favors a non-consensus approach to founder evaluation and emphasizes how the "Design Your Life" course influenced the founding of his fund. The episode also touches on upward liquidity potential and suggestions for industry change.


Theme 1: The Risk Curve of Seed Investing — Discontinuous Jumps, Not Linear Declines

Kanyi Maqubela argues that seed-stage risk does not decrease gradually with milestones but jumps instantaneously, akin to a quantum state.

Maqubela uses a physics analogy: at extremely early stages (very small scale and speed), Newtonian mechanics break down and quantum mechanics takes over. Risk does not follow a smooth curve like "hiring a technical co-founder → risk decreases by X%," but rather "jumps instantaneously from state A to state B." He cites Clubhouse as an example: Paul Davison and Rohan Seth launched a joint podcast project just as global lockdowns began. An exogenous shock caused risk to plummet instantly — a leap that no milestone-based analysis could have predicted.

Implication: This suggests that seed investors should focus on "whether founders can seize opportunities amid unpredictable jumps," rather than over-quantifying milestones. Maqubela emphasizes: "The degree to which founders influence outcomes may always be underestimated across all insurable vectors."


Theme 2: Founder Assessment – Three Contrarian Dimensions

Maqubela holds three contrarian views on founder assessment: risk aversion is preferable to risk appetite, passion is an outcome rather than an input, and domain insight outweighs domain experience.

1. Risk Aversion Over Risk Appetite: He argues that "risk tolerance in itself is not a good thing." The ideal founder is "someone who hates risk and wants to eliminate it as quickly as possible," rather than a thrill-seeker. He requires founders to ensure "zero personal ruin risk" and to take on at most "moderate personal financial risk."

2. Passion as an Outcome, Not an Input: Maqubela cites Scott Belsky's view that "momentum creates momentum," believing that "passion can be an output of success, not an input." People enjoy success and naturally become enthusiastic after achieving it. Therefore, he does not place excessive weight on narratives like "being obsessed with a field for a decade."

3. Domain Insight Over Domain Experience: He explicitly states, "If I had to choose between someone with domain experience and someone without, I would pick the latter." The hallmark of domain insight is when the other person says something you want to "steal and tweet," or offers a novel description of market structure. For example, describing the taxi market as "programmable central nervous system automatically managing data packet movement"—such insight may be inversely correlated with experience.

Data Support: Maqubela reviews his previous fund's portfolio and finds that over 50% of successful companies had seed-stage opportunities that were "non-consensus" (both internally and externally). After studying lists of unicorns/decacorns, he estimates that 30%–50% of successful companies had non-consensus entry points at their early stages.


Theme 3: The Value of VC – A Mirror and the Second "Yes"

Maqubela argues that VC provides limited real help to early-stage companies, but has two unique values: serving as a mirror for founders, and delivering the second "yes."

He quotes a seasoned VC: "A company's success is 'despite our best efforts' – if we didn't add negative value, they just kept moving forward." Most VC "value-add services" are actually used to win deals, not to help companies. Maqubela and his partner Steve Jang agree that early-stage VC can indeed help companies, but in a very specific way.

  • Mirror: VCs should honestly reflect the founder's strengths and weaknesses. "Co-founders won't tell you the truth, employees certainly won't, and clients don't even know they're lying. Only VCs can be that honest intermediary."
  • Second "Yes": When the market sees no clear progress in a company, an existing investor saying "I still believe" is the most powerful signal. He cites an example: a company pivoted from "long-distance ride-hailing" to "short-distance carpooling" and eventually went public, precisely because of the second vote of confidence from its internal investor.

Mechanism: Maqubela establishes a "Law & Order" model with founders – requiring them to report bad news first. Only then can the VC act as an honest intermediary and make critical decisions at pivotal moments.


Theme 4: Supply Chain & Infrastructure — From Invisible to Visible

Maqubela argues that COVID-19 transformed logistics and supply chains from "background noise" into "cultural currency," creating unique investment opportunities.

He invested in Cloud Trucks (providing "business-as-a-service" for independent truck drivers). He described a scene: as the first vaccines left the factory, a truck pulled out of a weigh station — a 67-year-old female owner-operator became a "hero carrying the future." This made him realize the importance of "moving atoms and bits" in safeguarding the future.

Trends:

  • Railway digitalization (autonomous trains optimizing safety)
  • Long-haul trucking automation may materialize faster than consumer vehicles
  • Space ridesharing (complementing SpaceX's reusable rockets)

Key data point: Maqubela notes that the "moving atoms" sector currently has consumer touchpoints, with only 5–6 job positions separating it from ordinary workers. This shift from invisible to visible has generated cultural currency and investment opportunities.


Theme 5: Crypto & NFTs — From Digital Scarcity to Creator Empowerment

Maqubela believes the core value of NFTs lies in reintroducing scarcity to digital content and granting original creators perpetual revenue streams.

He recalls the "cold" period of crypto investing from 2014 to 2016, when they invested in a failed DRM project (attempting to create a chain of ownership for digital objects). This later evolved into the NFT concept, but at the time it was "too early."

Current View:

  • As programmable protocols on smart contracts, NFTs can provide original creators with "perpetual and unlimited royalty streams," regardless of where the digital content spreads.
  • This applies to digital artists, photographers, musicians, and even MP3 files themselves.
  • He sees a trend in which "all categories of art that went from extreme scarcity to extreme abundance from 1999 to the present now have an opportunity to regain scarcity."

Extrapolation: Maqubela argues that this is not just a crypto phenomenon but part of a broader trend of "creator empowerment." He cites conversations with the founders of Spotify, Shopify, and Facebook — all of whom focus on "creators becoming the core narrative." His investment in Catch is based on the thesis that "the future of work will be entirely different from the 1950s manufacturing assembly line, and the social security system must be rewritten."


Theme 6: The Potential for Upward Mobility – A Turning Point for Stimulus and Entrepreneurship

Maqubela believes that the current period may be the first direct stimulus to the impoverished class in 30-40 years, creating a historic opportunity for upward mobility.

He notes:

  • The Nasdaq market cap is highly concentrated (dominated by a few companies), but excluding them reveals a vastly different market performance.
  • Stock ownership is heavily concentrated in pension funds, which are in decline; retail investors have yet to compensate by participating in hedge funds through LPs.
  • Small businesses have been underfunded and undersupported over the past 30 years. Data from the Kauffman Foundation shows that the U.S. entrepreneurship rate is at a 25-year low.
  • Health insurance costs ("cost disease") have long suppressed entrepreneurship.

Optimistic factors:

  • Pandemic stimulus flowed directly to low-income groups
  • The digital wave has spawned a surge of new startups
  • The creator economy provides new infrastructure for self-employed individuals

Maqubela's conclusion: "I believe these trends must and are beginning to reverse. While the pandemic has brought extreme tragedy, it has also opened the door to opportunity."


Mentioned Positions

Position Guest Stance Key Data
Cloud Trucks Bullish (Invested) Provides "business as a service" for independent truck drivers; first batch of vaccine transportation scenarios
Clubhouse Neutral (Discussed as a case) Founders are Paul Davison and Rohan Seth; risk surged instantly during global lockdowns
Coinbase Neutral (Mentioned as background) Steve Jang previously invested; its alumni are a source of founders for Kindred Ventures
Catch Bullish (Invested) Based on the thesis that "the future of work will reshape the social security system"
Roblox Neutral (As a creator economy case) Users earn Robux through Roblox's infrastructure
TikTok Neutral (As a creator platform case) Users create dance videos and generate revenue streams

Judgments Worth Remembering

1. “The risk at the seed stage is not a curve, but a quantum leap” (Maqubela): Risk does not decline smoothly with milestones but jumps instantly from state A to state B. Clubhouse during the lockdown is a classic example—no milestone analysis beforehand could have predicted it.

2. “I would rather choose someone without domain experience than someone with it” (Maqubela): Domain insight (a fresh description of market structure) may be inversely correlated with experience. He looks for insights that “make you want to steal them and tweet them.”

3. “Passion is an output of success, not an input” (Maqubela): People love success, and once successful, they naturally become passionate. Therefore, he does not value narratives like “obsessed with this field for 10 years.”

4. “VCs can do two things that other businesspeople cannot: be a mirror, and give a second ‘yes’” (Maqubela): A mirror honestly reflects a founder’s strengths and weaknesses; a second “yes” means that when the market is pessimistic, an insider investor says, “I still believe”—this is the most powerful signal.

5. “Risk tolerance itself is not a good thing” (Maqubela): The ideal founder is “someone who hates risk and wants to eliminate it as quickly as possible,” not someone who loves taking risks. He requires “zero personal ruin risk.”

6. Core of the “Design Your Life” course: optimize for ‘wow and giggles’ first, then optimize for utility (Maqubela): In the hypothesis stage, don’t ask “is it feasible,” but rather “what is most exciting.” This led him to decide to “found the 1001st seed fund when there were already 1000 new ones”—seemingly absurd, yet the right choice because it was “delightful.”

7. “LPs overvalue GP references, leading to homogenized investor thinking” (Maqubela): The industry has an astonishing margin for error (12 out of 25 companies going to zero can still yield a 3x return), but convergent investor thinking results in “feast and famine coexisting.” He suggests LPs invest more in geographic risks like Brazil, Nigeria, and Tanzania.

8. “When you find a rocket ship, don’t ask which seat to sit in—just get on” (Maqubela): This is the core lesson he learned from Obama’s campaign—when you have the chance to participate in something much bigger than yourself, especially when young, just do it.