Uncapped #33 | Vlad Tenev from Robinhood with Jack Altman (Alt Capital)

Date: November 20, 2025
Main Theme:
A candid, in-depth discussion with Robinhood co-founder and CEO Vlad Tenev about the evolving landscape of brokerage and fintech, Robinhood's history and future, generational investing habits, the rise of prediction markets, democratization of finance, and how AI is transforming the company and the industry.

Episode Overview

Jack Altman invites Vlad Tenev to unpack the evolution of online brokerage, Robinhood’s rise, shifts in investor psychology across generations, new frontiers like prediction markets, and the technological and cultural changes shaping the next decade of finance. The conversation oscillates between industry history, Robinhood’s trajectory, market trends, and Tenev’s personal reflections as a founder.

Key Discussion Points & Insights

The Evolution of Online Brokerage

[00:27 – 08:13]

• Historical Narrative:

  • Vlad outlines the history starting with Charles Schwab's disruption post-1972 “Mayday” deregulation, which allowed discount brokers to compete with the likes of Merrill Lynch.
  • “There’s a great book about this, A Piece of the Action by Nocera. … It’s basically a story of a big wave of democratization associated with lower costs.” – Vlad Tenev [00:54]
  • E*Trade’s founding: innovation with home computer stock trading in the 1980s, first profitable dot-com era brokerage.
  • Robinhood’s foundational innovations: 1) Mobile-first 2) HFT-inspired low-cost infrastructure 3) Building in the wake of Occupy and the 2008 financial crisis, connecting with a generation disillusioned by “forces beyond their understanding.”

• Gen Y and Occupy:

  • “No love was lost between young people and the big financial companies.” – Vlad Tenev [07:48]
  • Robinhood’s optimistic, system-internal empowerment positioned as “anti-Occupy”: helping more people become investors as a real lever of generational empowerment.

Generational Shifts & Brand Dynamics

[08:13 – 12:24]

• Old Brands for New Generations:

  • Discussion on how legacy brokerages (Schwab, Fidelity, Vanguard) lacked strong youth appeal.
  • “Gen Z and Gen Alpha … old big storied incumbents are kind of cool again.” – Vlad Tenev [09:12]

• Changing Retirement Attitudes:

  • “Gen Z’s are opening retirement accounts at 19 years old.” – Vlad Tenev [10:16]
  • Robinhood continuously adapts to serve multiple generations, aiming to avoid becoming a “broker for a specific generation,” unlike legacy firms.

• Brand Messaging:

  • “Older people want to be that [innovative] … younger people want trust and longevity.” [10:47–11:23]

Trading vs. Investing: Index Funds, Mental Accounting, Tools

[12:24 – 14:18]

• Passive vs. Active:
  • Vlad challenges the old wisdom that young investors only want passive strategies.
  • “It's not that people go from being a trader to being an investor. As their money grows, they just have more and more buckets.” – Vlad Tenev [13:10]
  • Robinhood’s evolution: from single account to multiple, reflecting users’ real-world “mental accounting.”

Robinhood as Financial Super App & Business Structure

[14:34 – 18:47]

• Business Model:

  • Robinhood moving beyond a “trading app” to become users’ financial “home.”
  • Banking, direct deposit, secondary financial accounts, and a growing conglomerate of interconnected services.
  • “We want to be your primary and your secondary financial account.” – Vlad Tenev [15:17]

• Three Arcs of Business:

  • 1. Active Traders: Options, crypto, Robinhood Legend, prediction markets (“number one in active traders”).
  • 2. Wallet Share: Credit card, Gold subscription, banking, retirement, human advisors (“number one in wallet share”).
  • 3. Global/Institutional: U.S. to global, retail to business/institutional (“number one global financial ecosystem”).

The Rise of Prediction Markets

[18:47 – 27:08]

• Explosive Growth:

  • Vlad describes the “big bang” as the US presidential election (2024), catalyzed by new regulatory clarity.
  • “We shipped [prediction markets] with about a week to go before the presidential election. … we still saw, I think, over half a billion contracts traded.” [21:57]
  • Expansion to sports (e.g., Super Bowl), AI forecasting, and other contract varieties.

• Why Prediction Markets Matter:

  • Spectacular growth in contract volume; Robinhood leads competitors via flexibility and quick product launches.
  • “Prediction markets, a way to think about them is they're truth machines. … Now we've created a tool that lets you do that.” – Vlad Tenev [24:46]
  • “The benefit is not just for the folks that are trading. It's almost like the trading and speculating is doing the work so that all of us have this reliable source of information.” [25:00]

• Wisdom of Crowds & Skin in the Game:

  • “The big distinguishing feature … it's a price. … from people with real skin in the game.” – Vlad Tenev [25:28]

• Entertainment vs. Economic Utility:

  • Vlad acknowledges lines blur between speculation and gambling, but emphasizes the economic utility in prediction markets, even for “just” sports.
  • “Without speculation, you can't have a functional financial market.” – Vlad Tenev [26:42]

Risk, Speculation, and New Tools for Expression

[27:08 – 33:13]

• Speculation as Human Nature:

  • “People want more granular ways to express their opinion about things.” – Vlad Tenev [29:35]
  • Emergence of granular instruments: options, zero-day contracts, prediction contracts on specific events (earnings, AI trends, etc.).
  • Technology enables what’s always been human appetite by reducing friction.
  • “Spec, there was always been speculation. You look back, Isaac Newton...” – Vlad Tenev [32:53]

• Frictions Falling:

  • “When you hitch it onto the technology wagon. … things get taken to zero pretty quickly.” [35:03]

Structural Barriers for Young People & Democratizing Access

[33:13 – 37:12]

• Systemic Challenges:

  • “Homeownership's becoming ... a lot more difficult ... student loan burden. ... cost of education has just continued to inflect.” – Vlad Tenev [34:02 – 34:24]
  • Shift of financial opportunity away from young people; growing value in private markets as companies go public later.
  • “I think that it's one of the biggest iniquities in capital markets.” – Vlad Tenev [35:54]

• Tokenization Vision:

  • Outlines tokenization as a middle-ground solution: custody traditional assets, mint/burn tradable tokens that represent them.
  • “The end user just wants economic exposure to things in a way that works.” [38:31]

AI’s Impact on Robinhood and the Industry

[39:32 – 46:53]

• Real AI Application:

  • Focus on customer support and engineering: measuring AI ticket deflection, code contribution, and overall productivity.
  • “Customer support… It’s worked super well. … It's the best in the industry actually.” – Vlad Tenev [41:07]

• Satisfaction & Human Preferences:

  • Some customers resist AI, but that’s declining. "That number ... is going down over time too, which is very good." [41:29]

• Marketing, Product, and Creative:

  • Growing AI-generated throughput in marketing creative and feature development.

• AI as Assistant & Autonomous Agent:

  • “We call it vibe trading… we announced that through our Robinhood Cortex for Legend product at our active trader event a few weeks ago.” – Vlad Tenev [43:51]
  • Vision of AI as an unobtrusive financial agent/facilitator (e.g. instant account migration, customized notifications, contextual digests).

Founder Mindset & Company Culture

[46:59 – 50:07]

• Staying Driven Long-Term:

  • Vlad reflects on founder’s unique leeway to realign company with their authentic values—discovered especially through hard times (COVID, public criticism).
  • “If you're lucky enough to still be running your company as the founder, then it. The buck stops with you for better and for worse.” – Vlad Tenev [49:17]
  • Importance of self-correction: “The company values have to be your values. The way you run the company has to be the way you run your life to some degree.” [48:47]

• Coping with Cycles:

  • “I know there’s probably going to be some time in the future where [we are] shitheads again.” – Vlad Tenev [49:37]

Notable Quotes

• On generational change in investing:
  “Gen Z’s are opening retirement accounts at 19 years old.” – Vlad Tenev [10:16]

• On Robinhood’s mission:
  “We want our customers to do well. … The best behavior for us is if someone's account balance with us just monotonically and continuously grows over time.” – Vlad Tenev [14:44]

• On prediction markets:
  “Prediction markets, a way to think about them is they're truth machines.” – Vlad Tenev [24:46]

• On speculation:
  “Without speculation, you can't have a functional financial market.” – Vlad Tenev [26:42]

• On tokenization:
  “The end user just wants economic exposure to things in a way that works.” – Vlad Tenev [38:31]

• On company building as a founder:
  “The company values have to be your values. The way you run the company has to be the way you run your life to some degree.” – Vlad Tenev [48:47]

Memorable Moments (with Timestamps)

• Robinhood as “anti-Occupy" movement: [07:48]
• The resurgence of “old” as cool: [09:27]
• Prediction markets’ big bang during 2024 election: [21:26]
• Prediction markets as media & truth: [24:46–25:08]
• Instant, AI-powered financial digests: [44:11]
• AI customer support “deflection rate” story: [41:07–41:57]
• Reflections on founder life cycles: [49:37]

Important Segment Timestamps

• [00:27] Online brokerage history & Robinhood’s founding story
• [08:13] Legacy vs. “cool” and generational brand perceptions
• [12:24] Index funds, active trading, and user behavior
• [14:34] Robinhood as super app, business structure
• [18:47] Prediction markets—growth, mechanics, and value
• [27:08] Speculation, risk, new tradable instruments
• [33:13] Systemic challenges for young investors
• [35:54] Private markets, tokenization
• [39:32] AI in Robinhood—customer support, engineering, products
• [46:59] Founder perspectives, values, and hard times

Tone

Conversational, candid, and forward-looking with a blend of analytical deep-dives and reflective asides. Vlad Tenev is direct, occasionally self-deprecating, consistently focused on “what’s next,” and meticulous in discussing both technology and company values. Jack Altman maintains a curious, personal tone aimed at drawing out both big picture trends and practical, founder-level lessons.

Summary: Who Should Listen

This episode is essential for anyone interested in the future of finance and fintech, from investors and technologists to founders wrestling with generational brand-building and the hard truths of company culture. Vlad Tenev’s perspective on democratizing access, building enduring brand relevance, and leveraging technology (especially AI) is rich with actionable insight and historical perspective.