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Colossus (Invest Like the Best / Business Breakdowns)Podcast21 Jan 2020Source: traffic.libsyn.comHost: Patrick O'Shaughnessy

Rebecca Kaden – Thesis Driven Investing - [Invest Like the Best, EP.155]

In plain words

This interview explains USV's third investment thesis: instead of betting on social networks or tech infrastructure, they now use existing internet platforms to lower barriers in education, healthcare, and finance. The author believes tech should target areas where prices have soared for decades, like education and medical care. Key holdings mentioned: Duolingo (gamified language learning on mobile), Stash (invest with $5, 80% of users were first-time investors), and Dia & Co (plus-size fashion with built-in social sharing).

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

Rebecca Kaden (Partner at Union Square Ventures) discusses the evolution of USV's third-generation investment thesis (Thesis 3.0), with the core argument that investments should revolve around "empowering large networks." USV focuses on three key areas: education, capital access, and health and well

~14 min full read · 9 sections
Deep Analysis

This Issue at a Glance

Rebecca Kaden (Partner at Union Square Ventures) elaborates on the evolution of USV's third-generation investment thesis (Thesis 3.0)—shifting from network effects to infrastructure, and then to systematically broadening access across three core domains by leveraging existing platforms and protocols: education, capital access, and health and well-being. Kaden argues that technology should focus on sectors where prices have risen rather than fallen over decades (education, healthcare), disrupting traditional systems with "better quality + lower cost," and that the current internet already possesses sufficient infrastructure to support this transformation.


Theme 1: The Evolution of USV’s Three Investment Theses — From Network Effects to “Broadening Access”

Rebecca Kaden argues that USV’s investment theses have undergone three iterations, each responding to the market structure of the preceding cycle.

Thesis 1.0 (2003–2004): Focused on “large-scale user participation networks and network effects.” At the time, this view was far from consensus, yet USV invested in Twitter, Indeed, Etsy, and others based on it. Kaden notes that these horizontal networks (e.g., Facebook) exhibited extremely strong network effects, leading the internet to become increasingly dominated by a few centralized platforms.

Thesis 2.0: Shifted in two directions — first, vertical networks (e.g., the education platform Duolingo, where network effects exist but the network itself is not the core of the business) and the infrastructure supporting these networks (Twilio, MongoDB, Stripe, Cloudflare); second, the decentralization theme, driven by concerns that centralized platforms monopolize user data and stifle innovation, with the belief that blockchain is the first technology with a genuine opportunity to decentralize the internet.

Thesis 3.0: The core judgment is that — since the platform and protocol layers have already been built — it is now possible to “systematically broaden access using these platforms,” achieving “better quality and lower cost” simultaneously in three areas (education, capital, and health and well-being). Kaden cites a key chart: over the past few decades, prices for televisions, toys, and software have steadily declined, while the costs of education and healthcare have skyrocketed exponentially. “Venture capital and technology have almost exclusively focused on the bottom half of the chart. What if we now direct innovation toward the top half?”


Theme 2: Education — From "Moving Classrooms Online" to "Transforming Learning Itself"

Kaden argues that the structural flaw in the U.S. education system is that it has barely been touched by technology in 50 years, while the gap between education and employment is wider than ever.

Core Problem: The talent produced by education is severely misaligned with today's labor demand, while student debt has grown exponentially. Kaden points out that traditional education changes "from the inside out"—through school districts and school boards—which is extremely difficult. USV's strategy is to penetrate "from the outside in": seeking products that can directly reach large-scale consumer demand.

Key Mechanism: Kaden emphasizes that USV looks not for companies that simply move offline courses online, but for cases where "the internet changes the way learning itself happens."

Company Model Key Data/Mechanism
Duolingo Free mobile language learning Fragmented, gamified, integrated into daily life—difficult to achieve in a classroom setting
Quizlet Crowdsourced learning tool Leverages the knowledge of a large user base
OutSchool K-12 synchronous online learning marketplace Teachers post courses (e.g., "Learn Spanish through Taylor Swift songs"), students enroll across regions; unlocks geographic constraints and personalized learning styles

Unique Insight: Kaden believes Zoom is a key "unlocking technology" for education. Companies like OutSchool are built on Zoom; synchronous video not only makes learning more convenient but also makes learning itself better—a similar logic applies to healthcare (e.g., an addiction recovery company built on Zoom that improves patient adherence).

Falsification Condition: If the trust in traditional education brands (Harvard, Stanford) cannot be challenged by emerging brands (e.g., Google), this theme may be limited. However, Kaden believes that companies like Google have already begun to drop degree requirements, and trust is shifting.


Theme 3: Capital Access — Productizing Financial Services for the Middle Ground

Kaden argues that the structural problem with the banking system lies in its business model, which favors the two ends of the fee spectrum — those who cannot afford basic services (charged fees) and ultra-high-net-worth individuals (charged based on AUM) — leaving the majority of Americans excluded.

Core Case: Stash

  • Entry Point: Start investing with as little as $5, using themes like "invest in what you believe in" (e.g., sustainability, technology, food) rather than complex stock tickers.
  • Key Data: 80%–85% of Stash customers had never invested before.
  • Expansion Path: Expand from investing to banking, savings, auto-save, 401(k), and custodial accounts — building trust gradually before offering full financial services.
  • Behavioral Insight: Customers who hold shares in a brand (e.g., Starbucks, Walmart) significantly increase their spending at that brand — "because they feel like owners."

Kaden emphasizes that financial services are fundamentally consumer behavior, not purely rational models. "Consumers are irrational and emotional. The sooner you understand what they do and why, the faster you can build products that make it easier for them to use."


Theme 4: The Distribution Challenge — From "Optimizing One Platform" to "Rapidly Testing Multiple Channels"

Kaden argues that distribution is a harder problem to solve than product, and that digital marketing is undergoing a fundamental shift.

The End of the Facebook Era: Over the past decade, Facebook aggregated billions of users, allowing businesses to acquire customers at a cost below platform optimization targets — a "magical era." But today, as platform efficiency improves, customer acquisition costs rise, and engagement among core user bases is fragmenting.

The New Definition of Marketing Capability: It is no longer "the ability to optimize a single platform," but rather "the ability to rapidly iterate and test multiple channels" — including emerging platforms (such as Fortnite, Roblox, Twitch), as well as the integration of offline, in-product, and brand marketing.

Early Signals Kaden Looks For: Whether the product itself contains a "distribution hook" — i.e., a natural sharing rhythm. Take Dia & Co (an e-commerce platform for plus-size women) as an example: when women receive a clothing box, they naturally post about it on social media, asking friends to help decide which items to keep — this is a built-in distribution mechanism within the product.


Theme 5: Health & Well-being — Consumerization of Healthcare and Community Belonging

Kaden divides "Health & Well-being" into two sub-themes:

5.1 Consumerization of Healthcare

Kaden argues that consumers are increasingly taking control of their own health spending, and the line between "wellness" and "healthcare" is blurring. Consumers do not distinguish between "Is this wellness or healthcare?" — they simply ask, "How can I feel better?"

Company Model Key Value
NURX Telehealth services via an app More private, faster, cheaper, no need to book a doctor's appointment
Modern Fertility At-home fertility testing Consumers can purchase directly, costing a fraction of what it would through a doctor

B2B Opportunity: Kaden notes that digital health companies are still built on "old rails," lacking speed, convenience, and value. She is bullish on SaaS products that provide infrastructure for these emerging companies, drawing a parallel to Plaid and Stripe in fintech. Ribbon Health (not in the portfolio) is an example: it offers a dynamic physician referral network for telehealth companies, solving the problem of outdated static databases.

5.2 Community and Belonging

Kaden believes loneliness is an epidemic, and while technology has created unprecedented connectivity, it has yet to crack "belonging."

Key Distinction: Network effects are "mechanisms of scale" — each new user makes the network better; but true engagement is "belonging" — how it becomes meaningful to you, how it changes the way you interact with others.

Case Study: Dia & Co — a functional product (selling clothes) where community becomes the core value. User behavior patterns: from liking others' posts → posting their own unboxing photos → sharing work and life → eventually, users who have never met in person plan vacations together. Kaden points out that this transforms the brand from "transactional" to a "trusted brand" that can withstand the test of time.

Kaden believes that in the future, more consumer companies will follow the path of "product → community" rather than the traditional "community → product." She hopes to see someone build a "nested technology platform" that supports different layers and key functions of community building — activities currently scattered across Facebook Groups, WhatsApp, Telegram, Slack, and other platforms.


Theme 6: Mentorship and USV Culture — Follow Your Interest, Not Market Noise

Kaden shared three lessons learned from Bill Campbell (a legendary Silicon Valley mentor): honesty, thoughtfulness, and follow-through. When she was 24, Campbell suggested she consider venture capital instead of joining Google or Facebook. He not only made introductions but also followed up with calls before and after her interviews — a depth of follow-through that Kaden still emulates today.

The core lesson learned at USV: "Investing based on your own interests and passions is reason enough in itself." When the market overheated (e.g., Series A rounds rising from $5–7 million to $20 million), partner Albert told her: "Don't look at companies for a few weeks. Just think about your ideas and what you believe in." Kaden believes that this "prepared mindset and commitment to a thesis" is what makes USV unique and serves as a way to resist market noise.


Mentioned Positions

Position Guest Stance Key Data
Duolingo Bullish (Portfolio) Mobile-based free language learning, fragmented and gamified model
Quizlet Bullish (Portfolio) Crowdsourced learning tool
OutSchool Bullish (Portfolio, Kaden directly involved) K-12 synchronous online learning market, built on Zoom
Stash Bullish (Portfolio) 80%-85% of clients had never invested before; minimum investment of $5
Dia & Co Bullish (Portfolio, led Series C) Built-in sharing mechanism within the product; users transition from transactions to community
NURX Bullish (Portfolio) Telemedicine, more private, faster, and cheaper
Modern Fertility Bullish (Portfolio) At-home fertility testing, cost far lower than traditional routes
Ribbon Health Neutral (Not an investment, but bullish on the model) Dynamic physician referral network, solving the problem of outdated static databases
Zoom Bullish (Not an investment, personal fan) Viewed as a "new track" in areas such as education and healthcare
Twilio Bullish (USV portfolio, Thesis 2.0) Infrastructure layer
MongoDB Bullish (USV portfolio, Thesis 2.0) Infrastructure layer
Stripe Bullish (USV portfolio, Thesis 2.0) Infrastructure layer
Cloudflare Bullish (USV portfolio, Thesis 2.0) Infrastructure layer
Twitter Bullish (USV portfolio, Thesis 1.0) Horizontal network
Indeed Bullish (USV portfolio, Thesis 1.0) Horizontal network
Etsy Bullish (USV portfolio, Thesis 1.0) Horizontal network

Judgments Worth Remembering

1. “Technology should focus on areas where prices are rising, not falling—education and healthcare—and disrupt them with better quality and lower costs.” (Rebecca Kaden) — Support: Over the past few decades, prices for televisions, toys, and software have declined, while costs for education and healthcare have surged exponentially; the core of USV Thesis 3.0 is to systematically broaden access to these sectors.

2. “Education is not about moving offline classes online, but about letting the internet transform learning itself.” (Rebecca Kaden) — Support: Duolingo’s learning approach is entirely different from the classroom; Zoom enables synchronous online learning that is not only more convenient but also makes learning itself better.

3. “Financial services are fundamentally about consumer behavior, not rational models. Consumers are irrational and emotional.” (Rebecca Kaden) — Support: Stash replaces complex stock tickers with “invest in what you believe in,” and 85% of its clients had never invested before; customers who own shares in a brand significantly increase their spending at that brand.

4. “Distribution is harder to solve than the product. The best products have built-in ‘distribution hooks’—a natural rhythm for sharing.” (Rebecca Kaden) — Support: Dia & Co users naturally post on social media when they receive clothing boxes, asking friends to help decide what to keep; the Facebook-era approach of “optimizing for a single platform” is being replaced by “rapidly testing multiple channels.”

5. “Network effects are a mechanism for scale, but true engagement is about belonging. Technology creates connection but has yet to crack belonging.” (Rebecca Kaden) — Support: Dia & Co users move from transactions to community, eventually planning vacations together despite never having met; loneliness is an epidemic, and community matters more than connection.

6. “Products can lead to community, rather than the traditional community-led product.” (Rebecca Kaden) — Support: Dia & Co is a functional product (selling clothes), but community becomes its core value; more consumer companies in the future will follow the “product → community” path.

7. “The best digital marketers will be the ‘fastest testers’—quickly investing in new channel opportunities rather than optimizing for a single platform.” (Rebecca Kaden) — Support: Facebook’s customer acquisition costs are rising, and core user engagement is fragmenting; emerging platforms like Fortnite, Roblox, and Twitch are becoming new distribution channels.

8. “At USV, following your own interests and passions to invest is reason enough in itself.” (Rebecca Kaden) — Support: When the market overheats, partners advise “don’t look at companies for a few weeks, just think about your ideas”; a prepared mindset and commitment to a theme are ways to resist market noise.