Cleo Hits $400 Million Revenue as Founder Automates Executive Oversight
Stripe
Cleo CEO Barney Hussey-Yeo predicts AI tools will flatten corporate structures by allowing executives to monitor code and operations directly without middle management.
## Background
This video was published on YouTube by Stripe on June 10, 2026. According to the page description, it features Cleo founder and CEO Barney Hussey-Yeo joining Stripe CEO John Collison for a fireside chat at Tour London.
## TL;DR
In this fireside chat, Cleo founder Barney Hussey-Yeo and Stripe CEO John Collison discuss Cleo's growth to $400 million ARR, its transition from basic regular expressions to modern LLM architectures, and its product philosophy of making financial advice engaging through humor and personality. Hussey-Yeo critiques European regulatory and investment landscapes compared to the US, advocating for a risk-tolerant culture of creative destruction. He also shares how AI tools have transformed his role as CEO by providing direct visibility into engineering workflows, flattening corporate management structures, and enabling smaller teams to run thousands of parallel experiments.
## Atmosphere & style
The conversation is dynamic, candid, and intellectually sharp, balancing high-level strategic insights with witty banter between two experienced tech leaders. Hussey-Yeo's direct, slightly irreverent humor—highlighted by jokes about his low-stakes poker bot and playful jabs at Collison being 'out of touch' with average consumers—creates a lively, conversational energy. Throughout the chat, the mood transitions smoothly from playful personal anecdotes to serious, provocative commentary on regulatory friction, AI management workflows, and the future of SaaS.
## Key takeaways
- [00:00](https://www.youtube.com/watch?v=70kWqOOWlAA&t=0s) Cleo standard modern startup performance: hit $400 million ARR while being based in Shoreditch, London.
- [00:00](https://www.youtube.com/watch?v=70kWqOOWlAA&t=0s) Hussey-Yeo funded his university education playing online poker and currently runs a custom AI poker agent that generates ~$200k annually in rakeback from low-stakes heads-up games.
- [01:13](https://www.youtube.com/watch?v=70kWqOOWlAA&t=73s) Public edge in high-stakes closed systems (like poker or quantitative finance) is kept proprietary rather than shared for systemic benefit.
- [02:35](https://www.youtube.com/watch?v=70kWqOOWlAA&t=155s) Cleo was founded in 2016 with the thesis that consumer financial decisions are wildly unoptimized, evolving from early regexes and basic classification models to modern generative LLMs.
- [05:46](https://www.youtube.com/watch?v=70kWqOOWlAA&t=346s) Financial advice needs to be active and personalized for the 99% of people, especially the 60% of Americans with less than $400 in savings who deal with daily financial stress.
- [08:10](https://www.youtube.com/watch?v=70kWqOOWlAA&t=490s) Cleo originally employed 30 female comedians to craft a distinct, humorous tone (e.g., 'Roast Mode') to engage users on financial health without feeling preachy.
- [10:15](https://www.youtube.com/watch?v=70kWqOOWlAA&t=615s) Financial advice tools must be proactive and agentic rather than passive interfaces, as consumers do not routinely query generalist models about their spending.
- [17:04](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1024s) Cleo employs 'product contrarianism' by taking traditionally dry and stressful domains like financial advice and making them fun, simple, and engaging.
- [18:14](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1094s) Value in financial services is increasingly found in the intelligence layer surrounding money management rather than in pure financial products or rails.
- [20:59](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1259s) UK regulatory sandbox timelines (up to 2 years) create a bottleneck relative to 18-month VC funding cycles, making the US a more dynamic environment for tech growth.
- [23:10](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1390s) European tech returns are heavily captured by North American LP capital, creating a structural loss of domestic GDP growth for Britain and Europe.
- [26:10](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1570s) Hussey-Yeo advises consumer AI founders to either embed monetization into the core experience on day one or focus entirely on hyper-growth before introducing revenue streams.
- [31:23](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1883s) Using LLMs to index internal communications, PRs, and docs directly grants executive transparency into code quality and velocity, permanently flattening middle management.
- [34:46](https://www.youtube.com/watch?v=70kWqOOWlAA&t=2086s) Companies will shift to deploying small, highly leverage teams where junior engineers use fleets of AI agents to test thousands of parallel bets annually.
- [37:20](https://www.youtube.com/watch?v=70kWqOOWlAA&t=2240s) The 'SaaS apocalypse' narrative is overblown because frontier models lack the deep domain knowledge, regulatory execution, and product craft required for enduring platforms.
## Detailed walkthrough
### [00:00](https://www.youtube.com/watch?v=70kWqOOWlAA&t=0s) From Online Poker Shark to Automated Rakeback Agents
The conversation kicks off with Stripe CEO John Collison highlighting Cleo’s massive milestone: hitting $400 million in Annual Recurring Revenue (ARR) as of the previous month. Based right in Shoreditch, London, Cleo has emerged as a unicorn and one of the world's top rapidly growing AI startups. However, Collison pivots the conversation back to founder Barney Hussey-Yeo’s background prior to founding the company—specifically his past as a self-described "poker shark" who funded his university education playing online poker.
Hussey-Yeo laughs off the "shark" label, recalling how he played low-to-mid-stakes heads-up poker online for four to six hours a day back before Game Theory Optimal (GTO) play and modern solver tools completely reshaped the scene. In a surprising reveal, Hussey-Yeo admits to having recently built his own AI poker agent that quietly plays low-stakes heads-up games on his behalf to farm rakeback. "I shouldn't say this publicly, but I earn about 200k every year now just through my little agent that plays and barely beats the low stakes," he shares with a grin. Collison jokes that playing against Hussey-Yeo online nowadays just means getting "rinsed" by his automated bot.
- Cleo reached **$400 million ARR** as of the month prior to the event.
- Hussey-Yeo funded his entire university education through online poker, playing 4–6 hours daily in the pre-GTO era.
- His custom automated poker bot generates approximately **$200,000 annually** in pure rakeback by grinding low-stakes games.
[01:13](https://www.youtube.com/watch?v=70kWqOOWlAA&t=73s) Game Theory Optimal and Unseen Edge in Closed Systems
Reflecting on poker's evolution, Collison notes that GTO represents doing the exact mathematically optimal action calculated by probability tables. Hussey-Yeo notes that when he was playing in 2012–2014, solvers had not yet solved the game for the public. Today, online heads-up poker is essentially a solved game, rendering human-driven online play largely dead—though live tournaments remain fun.
Collison draws a parallel to quantitative finance, citing the Black-Scholes model as another breakthrough that was created relatively late in human history. Hussey-Yeo emphasizes that anyone holding a true mathematical or strategic edge in a high-stakes environment—whether in poker or inside quantitative hedge funds—has every economic incentive to keep it proprietary rather than publishing it for GDP benefit. Collison adds an anecdote from professional cycling, where teams historically overinflated tires to 120 PSI until one clever Tour de France team secretly discovered that lower pressures yielded vastly better traction and speed, keeping the insight quiet as long as possible.
- Mathematical poker solvers have effectively "solved" heads-up online play, shifting human competitive play primarily toward live face-to-face tournaments.
- The parallel in cycling saw teams run high tire pressures (up to 120 PSI) for decades before hidden optimal-pressure discoveries provided a secret edge.
[02:35](https://www.youtube.com/watch?v=70kWqOOWlAA&t=155s) The Founding Thesis of Cleo in 2016
Shifting to Cleo's origin, Hussey-Yeo explains that the company was founded in 2016 as an AI assistant for personal finance—an idea that sounded bizarre at the time when natural language processing (NLP) was barely functional. Coming off a master's degree in machine learning right as the field was transitioning from computer vision breakthrough models like AlexNet to NLP, Hussey-Yeo teamed his background as a fintech data scientist with a fundamental core thesis: most everyday financial decisions made by consumers are wildly unoptimized.
Because personal finance is often the single most stressful aspect of a consumer's daily life, the goal was to build a system that could help a billion people make better financial choices—or execute those choices autonomously on their behalf. Collison quips that this was effectively attempting to build "GTO of your financial life." Hussey-Yeo points out that in 2016, two full years before the seminal Transformer paper was published and long before BERT or ChatGPT, the team had to build Cleo using basic intent classification and supervised learning models.
> "The thesis was everyone's decisions are wildly unoptimized and your financial life is the most stressful and important thing in your life. So, how could you make a billion people make better decisions every day or make decisions on their behalf?"
[04:20](https://www.youtube.com/watch?v=70kWqOOWlAA&t=260s) From Regular Expressions to LLMs: Cleo's Tech Evolution
Collison asks how Cleo provided advice in its earliest days before modern Large Language Models existed. Hussey-Yeo humorously confesses, "It started with regexes. We had a lot of regexes to start with." Beyond regular expressions, early Cleo relied on traditional supervised learning for multi-class intent classification and sequence prediction, combined with recommendation systems and reinforcement learning to deliver timely nudges.
The shift from classic supervised machine learning to generative LLMs completely revamped Cleo's product and system architecture. Collison probes on the core conceit of the product, questioning whether average consumers truly need deeply personalized financial advice when classic, static rules of thumb—such as maintaining a solid savings rate, investing in low-fee index funds like the MSCI World Index rather than chasing home-country bias, and avoiding heavily advertised consumer finance products—might be sufficient for most people.
- Early architecture relied heavily on **regular expressions (regexes)**, multi-class intent classification, sequence models, and reinforcement learning.
- The transition to LLM-native architectures fundamental transformed both backend system design and user-facing capabilities.
[05:46](https://www.youtube.com/watch?v=70kWqOOWlAA&t=346s) democratizing Financial Advice for the 99%
Hussey-Yeo directly challenges Collison's view, jokingly telling him he is showing "how out of touch you are, John, with the real consumer and normal humans on the street." For the average person, money isn't an abstract index fund portfolio; it is an omnipresent, highly stressful series of daily choices around rent, mortgages, subscriptions, and daily spending. Wealthy individuals in the top 1% have access to high-end financial advisors, but the remaining 99%—many of whom live paycheck-to-paycheck—are the ones who genuinely need assistance.
In the US, 60% of Americans have less than $400 in savings, facing volatile incomes and predatory high-interest consumer credit. Hussey-Yeo argues that money management shouldn't require staring at a dull list of bank transactions. Instead, an automated agent should work in the background: fetching low-rate credit when needed, optimizing spare capital into tax-free accounts, and eliminating predatory interest payments to unlock massive latent economic growth.
- **60% of Americans** possess less than $400 in liquid savings, underscoring the acute need for active daily financial management.
- The target audience for Cleo is the 99% of consumers who lack access to dedicated human wealth management or financial planners.
[08:10](https://www.youtube.com/watch?v=70kWqOOWlAA&t=490s) Roast Mode, Comedians, and Financial Health Metrics
When asked how Cleo actually influences spending habits without coming across as preachy, Hussey-Yeo reveals a unique product decision: early on, Cleo employed 30 female comedians on staff to write every single line of copy and dynamic response. Traditional financial institutions are notoriously dry and risk-averse, but Cleo discovered that humor and financial advice pair remarkably well. This led to famous features like Cleo's "Roast Mode," which playfully mocks users for overspending on weekend drinks or frivolous purchases.
To measure whether this engagement actually helps, Cleo developed an internal Financial Health Score ranging from 0 to 100. While early recommendation models optimized purely for user engagement (clicks and banter), the primary objective function now balances engagement with long-term financial health improvements—specifically driving users to spend less than they earn over a 2-to-3-month horizon.
- Cleo employed **30 female comedians** to write its original conversational tone and responses.
- "Roast Mode" uses humor to engage users around their spending habits rather than dry banking warnings.
- The core algorithm optimizes for an internal **0 to 100 Financial Health Score**, prioritizing the core financial primitive: spending less than one earns.
[10:15](https://www.youtube.com/watch?v=70kWqOOWlAA&t=615s) Deep Vertical Agents vs. Generalist Frontier Models
Looking at the competitive ecosystem, Hussey-Yeo explains that most people make financial choices based on "vibe-based optimization" or back-of-the-napkin guesses rather than structured spreadsheets. Just as specialized tools like Whoop bands are optimizing personal health, deep AI agents will emerge across key life verticals like health, finance, and education.
Collison asks whether users will eventually just upload financial statements into generalist frontier models like OpenAI's ChatGPT or Anthropic's Claude. Hussey-Yeo responds that while a user *can* connect a bank account via Plaid to ChatGPT today, engagement remains low because finance requires an **always-on, proactive, agentic** presence. Consumers rarely wake up wanting to manually query a search bar about their spending. Instead, value comes from a dedicated agent that proactively intervenes at the exact right time. Hussey-Yeo remains highly bullish on deep vertical applications—those integrating directly with specialized hardware, MRIs, blood tests, or bank rails—over generalist frontier models acting as a single interface for everything.
> "To engage people with financial advice, it's got to be proactive, and it's got to be agentic. So people don't wake up and go, 'Ooh, how much did I spend?'... It has to be this agent always on, always pushing information."
[13:17](https://www.youtube.com/watch?v=70kWqOOWlAA&t=797s) The Challenge of Memory and Personalization in Modern AI
Collison observes that current AI personalization mechanisms are still surprisingly primitive. He compares the memory architectures of current LLMs to the main character in the movie *Memento*—relying on static models paired with external flat notes written back and forth to simulate state. As the session segment draws to a close, Collison asks Hussey-Yeo to share his hands-on experience trying to engineer genuinely personalized user experiences on top of current AI model constraints.
- Current LLM personalization often relies on flat-file memory logs (analogous to *Memento*) rather than deep, native model adaptation.
- Building truly personalized vertical financial agents requires going beyond raw prompt engineering to capture rich contextual state over extended timelines.
[13:48](https://www.youtube.com/watch?v=70kWqOOWlAA&t=828s) Personalized Knowledge Bases vs. Raw Text
Addressing the notion that AI technology is inherently resistant to personalization, Barney Hussey-Yeo counters that while text is the primary medium today, the key lies in how structured data is stored and leveraged. Cleo has spent years building a comprehensive knowledge base for every individual user—capturing their financial aspirations, overall financial health, specific goals, and complete conversation history. Barney compares this to Microsoft Copilot’s recursive LLM architecture, noting that Cleo has been executing a similar strategy for years to construct structured user profiles.
He playfully critiques Stripe for not taking full advantage of its own potential intelligent knowledge base, suggesting Stripe should maintain a rich understanding of every connected card, user income level, and spending pattern. Cleo pairs its user database with an advanced recommender system that continuously evaluates what message or action will best optimize a user's financial health. Ultimately, Barney argues that text-based AI remains exceptionally effective as long as it operates over a thoughtfully structured schema and database.
---
- **Key Architectural Concept:** Storing user data in a structured schema allowing a recommender system to select prompts that optimize a specific user objective function.
- **Data Points Tracked:** Income, spending habits, financial aspirations, financial health metrics, and full interaction history.
[15:01](https://www.youtube.com/watch?v=70kWqOOWlAA&t=901s) Engineering Personality and Tone of Voice in AI
John Collison shifts the discussion to the concept of personality in AI, recalling how early LLM developers underestimated its impact. Citing examples like Anthropic’s Claude models and the controversies around OpenAI's GPT-4o—where users developed strong opinions on its sycophantic behavior—John asks how Cleo crafts its distinct personality, whether it adapts to individual users, and if they still rely on an "army of comedians" to write content.
Barney contends that while frontier lab models might afford to remain generic and unopinionated, brand-specific AI must embrace personality because it directly drives business metrics. For Cleo, an engaging, concise, and funny tone directly boosts monthly active users (MAUs) and top-line revenue. Initially, Cleo relied on a linear supervised learning approach with a single static tone of voice. However, with modern LLMs, Cleo dynamically tailors its interactions based on user demographics, income, and geographic location (e.g., distinguishing how it speaks to a user in Boston versus San Francisco).
```
Static, Single Tone (Supervised Learning) ---> Dynamic, Hyper-Personalized Tone (Modern LLMs)
(Adapts to location, income & user preferences)
```
- **Business Impact:** Personality and tone of voice directly increase user engagement, MAUs, and revenue.
- **Historical Evolution:** Shifted from hand-crafted comedian scripts to dynamic LLM persona generation tuned to regional and financial contexts.
[17:04](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1024s) Product Contrarianism: Making Financial Advice Fun
John observes that financial management is traditionally a high-stakes, stressful chore for most people, asking if Cleo's core strategy is simply making the topic more approachable. Barney confirms this, framing it as a strategy of "product contrarianism"—identifying the dominant pain point of incumbent solutions and taking the exact opposite approach in its most extreme form.
He compares this to Stripe taking complex, archaic enterprise payments and making them developer-friendly with a single click, or Monzo replacing opaque banking interfaces with transparent, simple user experiences. Cleo applied this exact inverse logic to financial advice: taking a domain that is historically dry, complicated, and boring, and making it engaging, simple, and humorous.
---
- **Strategy:** "Product contrarianism" or radical differentiation by attacking the incumbent's primary weakness.
- **Analogies Used:** Stripe (simplifying enterprise payment integration) and Monzo (simplifying traditional consumer banking UX).
[18:14](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1094s) The Primitives of Credit and the Role of Intelligence
When asked how the landscape of consumer financial products is shifting—such as the rise of Buy Now, Pay Later (BNPL) platforms—Barney notes that money fundamentally consists of a very limited set of primitives (borrowing, spending, saving). Consequently, underlying product innovation in financial services is slow and strictly bounded by regulators. While he acknowledges BNPL as an improvement over traditional credit cards—which often trap consumers into paying minimum balances on maxed-out limits for a decade—he finds building pure financial products somewhat constrained.
Barney emphasizes that the real value lies in the *intelligence layer* surrounding these products rather than the financial rails themselves. He warns against purely revenue-maximizing platforms like Robinhood, arguing that pushing high-margin financial products without proper guidance leads to poor consumer outcomes like impulsive day trading. In his view, combining financial products with genuine, uncompromised advisory intelligence is essential to long-term business integrity.
> "If you just provide financial advice or provide financial products without the advice... you end up just selling products and trying to get the most margin, and it leads you down this way of like, 'Ooh, let's do day trading.'... I think the intelligence and the decision-making and helping users do it for them is just so critical."
[20:59](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1259s) UK Regulatory Bottlenecks vs. US Institutional Checks
John asks Barney what he would reform if he were in charge of financial regulation in the UK. Barney delivers a sharp critique of the UK regulatory climate, arguing that it discourages the "creative destruction" necessary for economic progress. He notes that while UK regulators mean well with initiatives like regulatory sandboxes, these multi-year processes often outlast a startup's 18-month venture funding cycle, causing promising companies to collapse before reaching product-market fit.
Contrasting the UK with the United States, Barney praises the American system of checks and balances—spread across state and federal levels, courts, and regulators—which prevents centralized decision-making from stifling innovation. This institutional dynamism, despite its political friction, makes the US a far better environment for building high-growth technology companies.
---
- **Funding vs. Regulatory Timeline Gap:** UK regulatory sandbox processes often take up to 2 years, whereas typical venture funding cycles run roughly 18 months.
- **Geographic Focus:** Overwhelming preference for building in the US due to risk-tolerant capital markets and distributed regulatory mechanisms.
[23:10](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1390s) Cultivating Creative Destruction and Reallocating Capital
Expanding beyond fintech regulation to the broader European business landscape, Barney calls for a fundamental cultural shift from preserving legacy status to embracing risk-on "creative destruction." He points out that key institutions, pension funds, and Individual Savings Accounts (ISAs) across Britain and Europe are managed with a risk-averse mindset, causing economic stagnation across the region.
Barney highlights a critical structural flaw in European venture capital: much of the Limited Partner (LP) capital funding top-tier UK and European VCs originates from North American pension funds (such as Canadian and Californian public pensions). Consequently, the wealth generated by European tech innovation flows back to foreign retirees rather than driving domestic economic growth.
> "I'm not returning to the British state any GDP growth. It's all going back to California. And if you don't want a world which is completely bipolar where you can either build tech in China or you can build tech in the US, it's really bad for Europe."
- **Global Comparison:** Praise for Canadian and Australian pension funds (e.g., early bets on SpaceX) that generated massive returns for their citizens by investing heavily in venture capital.
- **Geopolitical Risk:** Warning that Europe risks becoming economically irrelevant in a bipolar tech landscape dominated entirely by the US and China.
[26:10](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1570s) Monetization Models and Monetizing AI Products
John steers the conversation toward the mechanics of running a consumer AI business, asking Barney how Cleo generates revenue and what insights he has on consumer willingness to pay. Barney explains that Cleo operates a freemium model that monetizes through both paid subscriptions and embedded financial products—including credit-building cards, BNPL, wage access, and wealth management tools.
Reflecting on Cleo's trajectory, Barney admits he spent the first four years prioritizing Monthly Active Users (MAUs) over monetization—a strategy that worked during early growth phases but posed challenges when approaching growth-stage investors. Advising founders building consumer AI products today, he recommends picking one of two extreme paths: either build a monetization primitive directly into the core user experience from day one, or ignore monetization entirely in the initial phase to aggressively capture consumer market share before overlaying revenue streams later.
<ElicitationsGroup message="Explore related topics from this discussion:">
<Elicitation label="Analyze Cleo's product contrarianism strategy" query="Explain how Cleo applies product contrarianism to financial services and compare it to companies like Stripe and Monzo."/>
<Elicitation label="Examine US vs. UK regulatory environments for tech" query="Summarize Barney Hussey-Yeo's critique of UK regulators versus US institutional structures in tech innovation."/>
</ElicitationsGroup>
[028:02] Monitization Models and Behavioral Psychology in Subscriptions
John Collison examines the monetization structure of digital products, contrasting traditional usage-based margins with subscription models like Costco's $100 annual fee, where profit is derived almost entirely from membership rather than product markups. He asks Barney Hussey-Yeo whether Cleo views itself as a subscription company, a seller of financial products, or a combination of both. Hussey-Yeo explains that subscription models became the primary mechanism for software because legacy payment rails made microtransactions inefficient and prone to failure. However, he envisions a shift toward friction-free, low-cost rails—such as stablecoins—enabling microtransactions similar to Chinese digital payment ecosystems.
Collison highlights how self-improvement products leverage consumer psychology, specifically the sunk cost fallacy (e.g., purchasing a gym membership to incentivize usage). Hussey-Yeo agrees, pointing out that human irrationality heavily influences subscription behavior. For example, adding a third subscription tier naturally shifts user selection toward the middle option due to standard behavioral tendencies. Collison jokingly summarizes this strategy as "weaponizing people's irrationality for good," which Hussey-Yeo playfully reframes as "harnessing" it.
- Costco derives virtually all its profit from membership fees rather than retail markups.
- Subscription models originally dominated due to high failure rates and costs associated with traditional microtransaction payment rails.
- Cleo introduced a third subscription tier to leverage standard pricing-anchoring behavior, driving users toward the middle tier.
[030:25] Managing Financial "Tilt" and Human Psychology
Collison draws an analogy to poker, where players go "on tilt" and make reckless, emotional decisions after experiencing losses, asking if Cleo sees similar behavior in personal finance. Hussey-Yeo confirms that financial management is deeply personal and emotional. Events such as job losses or relationship breakups frequently trigger irrational spending or financial panic, which Cleo tracks through user research to build supportive product interventions.
- Financial distress often follows major life events like job losses or breakups, triggering irrational financial behavior.
- Cleo designs targeted app mechanics and features to detect when users go "on tilt" and guide them back to sound financial habits.
[031:23] AI-Native Workflows and Flattening Executive Visibility
Hussey-Yeo details a dramatic shift in his role as CEO since early 2024. Previously, managing a 500-person company meant relying on division leaders, pre-reads, and manual status updates to gather operational context. Using Andrej Karpathy's workflow approach, Hussey-Yeo now uses Large Language Models (LLMs) to automatically synthesize daily Slack messages, Notion documents, and engineering pull requests across the company. The models summarize PRs, evaluate code quality, and maintain a centralized, real-time knowledge base.
This direct technical visibility bypasses traditional middle management filters and biases. While engineering managers are uneasy about the CEO directly tracking velocity and code quality through LLMs, Hussey-Yeo predicts this transparency will permanently flatten corporate structures by reducing the need for layers of middle management.
"I know who's shipping. I know who is the highest velocity, highest code quality... before I had this kind of weird view filtered through all these leaders that had all their different biases and all these different incentive structures." — Barney Hussey-Yeo
- Hussey-Yeo overhauled his management routine around January/February by replacing manual executive reporting with automated LLM synthesis.
- LLMs continuously index company Slack channels, Notion documents, and GitHub pull requests to auto-generate a comprehensive organizational "captain's log."
- Executive visibility through AI reduces reliance on middle management layers, leading to flatter organizational structures.
[034:46] Management Span of Control and the Agentic Team Model
Collison questions how these tools will impact manager-to-employee ratios and organizational design over a two-year horizon. Hussey-Yeo notes that while mentorship for junior employees remains necessary, the traditional hierarchy of multi-layered management is largely obsolete. Rather than maintaining deeply nested teams, companies will deploy smaller teams that manage a vastly higher volume of parallel bets and business units.
Addressing team composition, Hussey-Yeo rejects the idea of a 1-to-1 apprenticeship model. Instead, he hires fresh graduates from top machine learning programs (such as Cambridge and UCLA) who are fully "AI-pilled" and adept at operating AI tools. In this model, junior employees act as taste-makers directing fleets of recursive AI agents, allowing a company to dramatically scale its execution output.
"I like the idea that I can take 2,000 bets next year instead of like the 10 that I took last year." — Barney Hussey-Yeo
- High-performing junior engineers utilize fleets of parallel AI agents to handle execution, shifting the human role primarily to quality control and taste-making.
- LLM-assisted workflows allow companies to scale from taking a dozen major annual strategic bets to executing thousands of parallel initiatives.
[037:20] Countering the "SaaS Apocalypse" and Closing Remarks
Asked for his most contrarian AI take, Hussey-Yeo dismisses the prevailing narrative that frontier AI labs or simple wrappers will destroy traditional SaaS businesses (the "SaaS apocalypse"). Building enduring B2B or B2C platforms—such as Stripe or Cleo—requires immense domain-specific knowledge, regulatory execution, and product craft that raw foundation models cannot replicate. He critiques venture capital investors for over-extrapolating model capabilities and flocking to frontier labs out of a lack of technical understanding.
Hussey-Yeo predicts that market rationality will return over time, affirming that software remains the core driver of economic growth and GDP. Collison wraps up the fireside chat, noting that software evolution will be marked by continued creative destruction across diverse market players rather than total consolidation, before bringing the Stripe Tour London main stage program to a close.
- Hussey-Yeo characterizes the market fear of model-wrapper dominance as wildly overblown due to the underlying operational complexity of real-world software businesses.
- Software innovation and creative destruction remain the fundamental drivers of long-term global economic and GDP growth.
- The session marks the formal conclusion of the main programming for Stripe Tour London, leading into the Expo Hall networking reception.
## Notable quotes
> [00:00](https://www.youtube.com/watch?v=70kWqOOWlAA&t=0s) I shouldn't say this publicly, but I earn about 200k every year now just through my little agent that plays and barely beats the low stakes — Barney Hussey-Yeo
> [02:35](https://www.youtube.com/watch?v=70kWqOOWlAA&t=155s) The thesis was everyone's decisions are wildly unoptimized and your financial life is the most stressful and important thing in your life. So, how could you make a billion people make better decisions every day or make decisions on their behalf? — Barney Hussey-Yeo
> [04:20](https://www.youtube.com/watch?v=70kWqOOWlAA&t=260s) It started with regexes. We had a lot of regexes to start with. — Barney Hussey-Yeo
> [05:46](https://www.youtube.com/watch?v=70kWqOOWlAA&t=346s) how out of touch you are, John, with the real consumer and normal humans on the street. — Barney Hussey-Yeo
> [10:15](https://www.youtube.com/watch?v=70kWqOOWlAA&t=615s) To engage people with financial advice, it's got to be proactive, and it's got to be agentic. So people don't wake up and go, 'Ooh, how much did I spend?'... It has to be this agent always on, always pushing information. — Barney Hussey-Yeo
> [18:14](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1094s) If you just provide financial advice or provide financial products without the advice... you end up just selling products and trying to get the most margin, and it leads you down this way of like, 'Ooh, let's do day trading.'... I think the intelligence and the decision-making and helping users do it for them is just so critical. — Barney Hussey-Yeo
> [23:10](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1390s) I'm not returning to the British state any GDP growth. It's all going back to California. And if you don't want a world which is completely bipolar where you can either build tech in China or you can build tech in the US, it's really bad for Europe. — Barney Hussey-Yeo
> [31:23](https://www.youtube.com/watch?v=70kWqOOWlAA&t=1883s) I know who's shipping. I know who is the highest velocity, highest code quality... before I had this kind of weird view filtered through all these leaders that had all their different biases and all these different incentive structures. — Barney Hussey-Yeo
> [34:46](https://www.youtube.com/watch?v=70kWqOOWlAA&t=2086s) I like the idea that I can take 2,000 bets next year instead of like the 10 that I took last year. — Barney Hussey-Yeo
## Mentioned
Barney Hussey-Yeo, John Collison, Cleo, Stripe, Tour London, AlexNet, BERT, ChatGPT, MSCI World Index, Whoop, OpenAI, Anthropic, Claude, Plaid, Microsoft Copilot, GPT-4o, Monzo, Robinhood, SpaceX, Costco, Andrej Karpathy, Notion, GitHub, Slack, Cambridge, UCLA
In conversation with Stripe CEO John Collison, Cleo founder Barney Hussey-Yeo argues that consumer finance is best transformed through proactive, personality-driven AI agents rather than static rules or generic foundation models. Hussey-Yeo contends that sustainable technology value lies in deep vertical domain execution, structured user context, and organizational workflows transformed by machine learning.
Targeting Everyday Consumer Financial Stress (5:46)
Hussey-Yeo contrasts typical consumer realities with standard wealth management advice. Pointing out that 60% of Americans have less than $400 in liquid savings and face volatile incomes alongside high-interest debt, he argues that high-level guidance like investing in global index funds fails the 99% of consumers living paycheck to paycheck. Founded in 2016, Cleo reached $400 million in ARR by building an automated assistant designed to manage daily cash flow and eliminate unoptimized spending choices.
Personality and Architecture in Vertical Agents (8:10)
Cleo's early architecture evolved from regular expressions, multi-class intent classification, and reinforcement learning into generative large language models. To drive engagement around stressful financial topics, the company adopted an irreverent tone—initially hiring 30 female comedians to craft features like "Roast Mode"—before transitioning to dynamic LLM persona generation tailored to user demographics and location. Hussey-Yeo emphasizes that Cleo balances conversational banter against an internal Financial Health Score (0 to 100), aiming to guide users toward spending less than they earn over two- to three-month horizons.
Structured Intelligence Versus Frontier Model Wrappers (10:15)
Hussey-Yeo rejects the idea that generalist frontier models like ChatGPT or Claude will displace specialized software platforms. Because everyday consumers rarely open search interfaces to inspect bank accounts, effective financial management demands an always-on, proactive agent. Cleo maintains structured individual profiles tracking income, aspirations, health metrics, and interaction histories. Hussey-Yeo maintains that underlying financial primitives (spending, borrowing, saving) innovate slowly and carry heavy regulatory burdens; the durable enterprise value sits in the intelligence and advisory layer directing those rails rather than pure product margin maximization.
Institutional Inertia and Venture Capital Distribution (20:59)
Critiquing the European and UK business environments, Hussey-Yeo argues that risk-averse regulation and multi-year sandbox timelines frequently outlast typical 18-month startup venture cycles, hampering "creative destruction." In contrast, he views the US system of checks and balances across courts, states, and federal regulators as better suited for technology growth. Furthermore, he points out that top European venture capital relies heavily on North American pension fund limited partners, meaning investment returns from European tech innovations often flow back to foreign retirees rather than regenerating domestic capital.
AI-Native Operations and Flatter Corporate Hierarchies
Internally, Hussey-Yeo restructured executive operations by using LLMs to index Slack messages, Notion documents, and GitHub pull requests. By summarizing code quality and developer velocity directly, this workflow bypasses traditional middle-management reporting filters. Rather than running nested management hierarchies, Hussey-Yeo advocates deploying smaller teams of junior machine-learning graduates who act as quality controllers directing fleets of autonomous coding agents, enabling organizations to execute thousands of simultaneous operational bets.
Hussey-Yeo dismisses forecasts of an AI-driven "SaaS apocalypse," asserting that foundation models cannot easily replace the regulatory expertise, domain craft, and proprietary data structures of established software platforms. However, questions remain regarding how traditional middle management and apprenticeship structures will adapt as agentic automation reshapes corporate governance.
[0:00] Barney Hussey-Yeo: I shouldn't say this publicly, but I earn about 200k every year now just through my little agent that plays and barely beats the low stakes
[2:35] Barney Hussey-Yeo: The thesis was everyone's decisions are wildly unoptimized and your financial life is the most stressful and important thing in your life. So, how could you make a billion people make better decisions every day or make decisions on their behalf?
[4:20] Barney Hussey-Yeo: It started with regexes. We had a lot of regexes to start with.
[5:46] Barney Hussey-Yeo: how out of touch you are, John, with the real consumer and normal humans on the street.
[10:15] Barney Hussey-Yeo: To engage people with financial advice, it's got to be proactive, and it's got to be agentic. So people don't wake up and go, 'Ooh, how much did I spend?'... It has to be this agent always on, always pushing information.
[18:14] Barney Hussey-Yeo: If you just provide financial advice or provide financial products without the advice... you end up just selling products and trying to get the most margin, and it leads you down this way of like, 'Ooh, let's do day trading.'... I think the intelligence and the decision-making and helping users do it for them is just so critical.
[23:10] Barney Hussey-Yeo: I'm not returning to the British state any GDP growth. It's all going back to California. And if you don't want a world which is completely bipolar where you can either build tech in China or you can build tech in the US, it's really bad for Europe.
[31:23] Barney Hussey-Yeo: I know who's shipping. I know who is the highest velocity, highest code quality... before I had this kind of weird view filtered through all these leaders that had all their different biases and all these different incentive structures.
[34:46] Barney Hussey-Yeo: I like the idea that I can take 2,000 bets next year instead of like the 10 that I took last year.
Original transcript
[0:00] Thanks for being here.
[0:00] >> Thanks for having me.
[0:01] >> So,
[0:02] Cleo, you guys are presumably familiar
[0:05] with a phenom in the
[0:07] consumer financial advice space, 400
[0:10] million in ARR.
[0:12] >> As of last month.
[0:13] >> Yes.
[0:14] Unicorn
[0:16] and really rapidly growing, one of the
[0:18] top AI startups and based right here in
[0:20] Shoreditch. Um, but before you started
[0:23] Cleo, I want to go back to your prior
[0:25] career.
[0:26] >> Yeah.
[0:26] >> You were a poker shark. Is that right?
[0:29] >> Uh,
[0:30] shark or fish? I'm I'm I played at
[0:32] university. I funded my university
[0:34] career through playing online poker. Um
[0:36] >> I only know what I've seen in Rounders
[0:39] and Molly's Game [laughter] and all this
[0:40] kind of stuff. So, how does actually
[0:43] making like professionally
[0:45] playing poker work?
[0:46] >> This was back before you had GTO and the
[0:49] solvers. So, it's it's all online and
[0:51] you know, play on like at multiple sites
[0:53] and you'd play four to six hours a day
[0:55] heads-up. And actually really
[0:56] interestingly, I've just built an AI
[0:58] agent that now plays for me and earns
[1:00] rake back. So, I make about I shouldn't
[1:02] say this publicly, but I earn about 200k
[1:04] every year now just through my little
[1:06] agent that plays and barely beats the
[1:08] low stakes. But yeah, I used to play,
[1:10] you know, low mid stakes heads-up and it
[1:12] was quite profitable.
[1:13] >> And how So, GTO is
[1:16] game theory optimal, which is doing the
[1:18] exact right thing that the probability
[1:21] tables would tell you that you should
[1:22] do, right?
[1:23] >> And you didn't have that in 2012, '13,
[1:26] '14 when I was playing.
[1:27] >> Really?
[1:29] >> you had the solvers and we actually
[1:31] learned how you could build beat the
[1:32] game. You did still ride the, you know,
[1:35] the edge. You can probably beat the GTO
[1:37] solvers, but it's basically a solved
[1:39] game, which means online play is kind of
[1:42] is dead now, but you should play
[1:43] tournaments. You go play a live
[1:44] tournament, they're always fun.
[1:46] >> Well, cuz I'd be playing against your
[1:47] bots probably.
[1:48] >> Yeah, don't play online against me.
[1:49] >> Okay. Okay. You're going to get rinsed.
[1:51] That's very interesting. You know, it
[1:52] was um
[1:53] a lot of these things are discovered
[1:54] later than one would think. Like
[1:56] Black-Scholes is, you know, a relatively
[1:58] recent invention for, you know, valuing
[2:00] financial options. And I didn't realize
[2:01] that GTO is such a recent invention in
[2:04] poker.
[2:04] >> Well, you don't want to tell people if
[2:05] you've got an edge, right? So, there's
[2:07] probably all these things in hedge funds
[2:08] where you could have a massive economic
[2:11] benefit to GDP, which you'd probably
[2:12] keep a secret.
[2:13] >> Exactly. Yeah, this happened in cycling
[2:15] as well, in pro cycling, where people
[2:17] used to inflate their tires up really
[2:19] high, uh you know, 120 PSI or something
[2:21] like that. And then one Tour de France
[2:23] team figured out that actually everyone
[2:25] was over inflating their tires and you
[2:26] don't need to over inflate your tires.
[2:28] And they kept the secret from everyone
[2:30] for a long time. Anyway, there's still
[2:32] plenty of room for new inventions is
[2:33] what we're taking away here. But we are
[2:35] not here to talk about pro cycling or
[2:37] pro poker. We're here to talk about
[2:38] Cleo. So, maybe just to orient people
[2:40] who aren't familiar or aren't users of
[2:41] the product, what does it do? Um how'd
[2:44] you guys get here?
[2:45] >> Yeah, well, we started in 2016. So, it's
[2:47] an AI assistant for your money, which
[2:49] was weird in 2016 and now is like the
[2:52] thing to be building.
[2:53] >> AI was not as hot in 2016.
[2:55] >> Yeah, building an AI system was
[2:56] completely weird. Like, natural language
[2:57] processing was barely working. But it
[2:59] was the really big research output at
[3:01] the time. So, I did my masters in
[3:02] machine learning and we'd just gone from
[3:04] the vision era of like we'd beaten
[3:06] AlexNet and then NLP became the thing
[3:09] all my professors were interested in.
[3:10] >> Yep.
[3:10] >> So, I'd worked at a fintech as a data
[3:12] scientist and I had this, you know,
[3:15] fascination with machine learning and
[3:16] knew it was going in that direction. So,
[3:18] the the thesis was everyone's decisions
[3:20] are wildly unoptimized and your
[3:22] financial life is the most stressful and
[3:24] important thing in your life. So, how
[3:26] could you make a billion people make
[3:27] better decisions every day or make
[3:29] decisions on their behalf? And how could
[3:30] you change the economy of the world,
[3:32] everyone's life through doing that? GTO
[3:34] >> of your financial life, if you will.
[3:36] >> GTO, yeah, I don't think it would sell,
[3:39] but
[3:40] maybe maybe to you, John.
[3:41] >> Yeah,
[3:42] >> [laughter]
[3:42] >> um for the just free idea for the
[3:44] magazine article, you know, for the
[3:45] opening paragraph on
[3:47] on Cleo. Um okay, but that that's
[3:50] interesting, right? Cuz you're founded
[3:51] in 2016. That's before It's obviously
[3:54] before Chat GPT, but that's like before
[3:56] LLMs.
[3:57] >> 2 years before the Transformer.
[3:58] >> Yeah, but even back then if you the
[4:00] metal hour we were just talking about
[4:02] like they were really focused on it and
[4:04] they were pushing out a bunch of good
[4:06] you know it was just intent
[4:06] classification back in the day.
[4:08] >> Then you had 2 years later it was the
[4:09] Transformer and then you had BERT.
[4:11] >> Yeah.
[4:11] >> Everyone then in computer science knew
[4:13] this was going to be a thing and then
[4:15] everyone else just woke up when 3.5
[4:17] dropped, but you could see it, right?
[4:19] >> But so what I I mean I presume today
[4:21] you're heavily LLM based. Just how did
[4:23] this work? Like how were you providing
[4:26] the financial advice? Like you the user
[4:28] inputs some data and then what?
[4:30] >> It started with regexes. Uh we had
[4:32] actually [laughter] we had a lot of
[4:33] regexes to start with. But then it was
[4:34] just traditional supervised learning,
[4:36] right? So you had intent classification
[4:37] and then seek classification. It's a bit
[4:39] nerdy, but intent is you know what you
[4:42] say in a sentence. So it was a big big
[4:45] multi-class supervised learning and then
[4:47] you had when we still do had the
[4:49] recommend the systems and reinforcement
[4:51] learning to push you information at the
[4:52] right time. So you've gone from a
[4:54] supervised learning world to a you know
[4:56] an LLM based world and that completely
[4:59] changed our architecture and our product
[5:00] actually.
[5:01] >> Yep.
[5:02] >> Um
[5:03] how
[5:06] the conceit of Cleo is that you should
[5:08] have personalized financial advice.
[5:11] How personalized does financial advice
[5:13] actually need to be? Cuz you know
[5:14] there's a view that you could say you
[5:15] should have the right savings rate and
[5:18] then you should invest in an low
[5:21] fee index fund
[5:23] um
[5:24] and uh you know you shouldn't buy kind
[5:26] of financial products. It's like you
[5:27] know you shouldn't use um foods that are
[5:29] advertised on TV like the good foods
[5:30] don't you know don't have an ad budget
[5:32] and similarly you know you shouldn't buy
[5:34] financial products that are aggressively
[5:35] sold. You should
[5:36] uh you should buy a low fee index fund
[5:38] and then you shouldn't have a home
[5:39] country bias. You know you shouldn't buy
[5:41] the FTSE 100. You should buy the MSCI
[5:42] World Index. Like is that not enough
[5:45] financial advice for everyone?
[5:46] >> Uh
[5:46] showing how out of touch you are, John.
[5:48] >> With the with the the real consumer and
[5:50] the the normal humans on the street. And
[5:51] like, your life is your money. You spend
[5:53] like it's the most stressful thing for
[5:55] the majority of people in their life.
[5:57] You spend so much boring admin time
[5:59] thinking about how you make financial
[6:00] decisions. From, you know, where are you
[6:02] going to live? Where's that mortgage?
[6:03] Where's that rent going to be? How big
[6:04] should that be? Every single thing you
[6:06] do every day is a financial decision in
[6:07] reality. You make all these transactions
[6:09] every single day. Or someone's Stripe.
[6:11] Uh, but imagine if you had a world where
[6:13] everyone was making rational, sensible,
[6:16] you know, more optimized decisions. If
[6:18] you think about how much money goes
[6:19] towards consumer credit or paying on
[6:20] interest when it doesn't need to. You
[6:22] could really change the not just um
[6:26] Yeah,
[6:27] uh, not just like the top 1% of people
[6:29] that get a financial advice. It's the
[6:30] 99% that actually need the financial
[6:32] advice. The people that are living, you
[6:34] know, 1-month, 2-month, 3-month savings.
[6:36] If they can have a better life and make
[6:37] better decisions, and you can do it for
[6:39] them. You shouldn't have to think about
[6:40] finance, right? It should just happen on
[6:42] your behalf. You need credit, you should
[6:44] just ask. It should go get it for you.
[6:46] If you have wealth, then it should just
[6:47] go get the best return. It should be
[6:49] tax-free.
[6:50] There should be a world where you don't
[6:51] manage your money by looking at a
[6:53] balance and a list of transactions. And
[6:55] that's coming very soon, right?
[6:58] >> Where are you generally trying to steer
[7:00] people? Like I can imagine there's kind
[7:02] of avoiding bad financial products, like
[7:04] the classic one of, you know, borrowing
[7:06] on a credit card.
[7:07] Uh, there's
[7:09] uh, the uh, maybe price comparison where
[7:11] if you're getting a mortgage, you can
[7:12] get somewhat better rates here versus
[7:14] there. There's tax efficiencies. But
[7:16] just like
[7:17] >> It's actually your life. If you think
[7:18] about most of the consumers in the US,
[7:20] it's 60% of Americans have less than
[7:21] $400 of savings. It's how they spend
[7:23] their money every single day. How much
[7:25] do they earn? What's their income
[7:26] volatility? How much are they spending
[7:28] on rent, mortgages, subscriptions? Like,
[7:31] what are they actually doing with their
[7:32] financial life? And you can really help
[7:35] someone just by laying it out to them,
[7:37] making better decisions for them. And
[7:38] then on the products, they are just
[7:40] wildly unoptimized, especially at the
[7:42] lower end. They're paying incredibly
[7:43] high interest rates. They are not
[7:44] getting any returns on their savings.
[7:46] Most people don't have investments when
[7:48] they just They sit it in like a cash ISA
[7:50] in the UK. It's just like crazy the
[7:53] amount of GDP growth and the amount of
[7:55] financial wealth you could be creating
[7:56] people that's like left on the table.
[7:58] So, I just think there's trillions and
[8:00] trillions of good that you can do for
[8:02] society and humans, but also just the
[8:03] economy as well. If you had this thing
[8:05] moving effectively through the system,
[8:07] you can dramatically increase GDP
[8:09] growth.
[8:10] >> How do you advise people on spending? I
[8:12] mean, like there's the meme online of
[8:13] the millennials with their avocado
[8:14] toast. Is it like you're trying to
[8:17] reduce the amount of avocado toast
[8:18] consumed? Or like how do you actually
[8:20] steer people usefully in an actionable
[8:22] way on spending?
[8:23] >> Do you know what Do you know what's
[8:23] funny back in the day? Cuz it wasn't as
[8:25] intelligent. We had to really rely on
[8:26] humor. So, we had 30 female comedians on
[8:29] staff. Cleo was a you know, it's a
[8:30] female agent. So, we had these female
[8:32] comedians and they wrote every single
[8:35] line of copy both what we pushed and
[8:37] what we responded with. And we found
[8:39] that humor and money actually go
[8:41] together weirdly well, which no
[8:42] financial institution
[8:44] spoke once to your lawyers and your your
[8:46] executives. Bankers are generally not
[8:48] known for that. Not known for their
[8:49] humor, yeah. So, that was a real unlock
[8:51] for us in terms of engagement and like
[8:53] there's there's a roast mode in Cleo
[8:54] that makes fun of you for your spending.
[8:57] I don't know what it would make fun of
[8:59] you. Maybe the cheeky pints, John.
[9:01] But
[9:02] you know, roast you for for what you've
[9:03] done over the weekend at the bar,
[9:04] whatever it is. And people really like
[9:07] that as a way to engage them in simple
[9:09] actionable financial advice. And
[9:11] increasingly it's just taking action on
[9:12] their behalf. It's it's moving accounts.
[9:14] It's moving money. It's getting them the
[9:15] best product, whatever that is at that
[9:18] time for that user.
[9:20] >> Um
[9:21] do you have a way of measuring how Cleo
[9:24] is steering people's financial health?
[9:27] >> Yeah. Yeah, we have measure I'm actually
[9:29] really surprised that you Well, you
[9:30] probably do internally, but there's We
[9:33] have constructed a view of financial
[9:34] health for every individual at Cleo.
[9:37] It's a score 0 to 100 on all these
[9:39] variables all these features. So we know
[9:41] whether you're leveling up your
[9:42] financial health or you're you're
[9:43] degrading it based on actions that you
[9:45] do. So actually the objective function
[9:47] of the recommend system it used to just
[9:49] be engagement. So it was like can we
[9:51] make you like click this button and it
[9:52] was fun. But now it is financial health
[9:54] and engagement. So we're optimizing for
[9:57] did this bit of advice did this action
[9:59] lead to in 2 months 3 months time their
[10:02] financial health getting better? And
[10:03] them spending less than they earn which
[10:04] is like the core primitive uh
[10:06] >> Them spending less?
[10:07] >> Spending less than they earn.
[10:08] >> Oh yeah.
[10:09] >> It's like the core primitive of every
[10:10] human in that kind of uh low to middle
[10:13] income, right?
[10:13] >> Yes. Yes. Who do you compete with? Like
[10:16] is this substituting for existing
[10:18] products? Is this just kind of a new
[10:20] thing this
[10:21] >> Yeah, well think about how people make
[10:23] financial decisions today like
[10:25] it's a it's a vibe based optimization
[10:27] game for most people. It's um maybe it's
[10:29] a packet and a napkin but the vast
[10:32] majority of consumers don't budget. They
[10:34] don't think about their money in a very
[10:35] rational way or they do it in a very
[10:38] you know late way. There's only a really
[10:39] specific number of nerds probably
[10:41] everyone in this room actually um that
[10:43] will have an Excel and opt to Sorry I
[10:45] shouldn't make fun of all the audience
[10:47] uh but have this you know set of uh
[10:50] advice that they'll construct
[10:51] themselves. So we're really in the
[10:54] advice game for people that don't have
[10:55] advice and I think there's going to be
[10:57] loads of avenues like this. Imagine
[10:59] health, right? We all make terrible
[11:01] decisions for our health all the time.
[11:02] We've all got a whoop now and we're all
[11:03] getting into it. But there's going to be
[11:05] all these big verticals in your life
[11:06] whether it's education or health or
[11:08] finance where your decisions are wildly
[11:10] unoptimized today and they are going to
[11:11] be
[11:13] they're just going to be so much more
[11:14] thought through. Imagine how you deploy
[11:16] capital and people at Stripe. There's
[11:17] probably an army of nerds that are
[11:19] thinking about how you deploy that
[11:21] versus your strategy and where your
[11:22] goals are going. Imagine if you do that
[11:24] for every human for every decision they
[11:26] ever have to make.
[11:27] >> So you think you'll go broad and beyond
[11:29] financial advice into
[11:31] >> There's a there's a lot to do in
[11:32] financial advice. I would big time. Um
[11:34] so we're we're going to nail that first.
[11:36] And I think, you know, you're going to
[11:37] have these four or five agents that go
[11:39] really deeply vertical in these big
[11:41] specific areas of your life. And I don't
[11:43] think they're going to be the frontier
[11:44] model companies, actually. I think
[11:45] they're going to be companies that focus
[11:47] all on health. They go all the way to
[11:48] the MRI and the blood test. And they
[11:49] have a whole stack of advice. So I'm
[11:51] bullish on that, and I'm less bullish on
[11:53] like
[11:54] OpenAI being the interface for everyone
[11:56] for everything. Um
[11:58] >> But do you see that competition dynamic
[12:01] with users where anyone who's building
[12:03] AI tools, there's always the um
[12:06] anyone who's building kind of specific
[12:07] vertical AI tools, there's always the
[12:09] dynamic where people might just, you
[12:10] know, take a bunch of financial
[12:12] statements or connect their bank account
[12:14] to Claude and start asking it questions.
[12:17] Do you practically see that behavior
[12:19] where an alternative to using Cleo is
[12:22] wiring up the relevant data to an LLM?
[12:26] >> Well, you you can connect your plan
[12:27] account now to ChatGPT and ask
[12:29] questions, right? But I would bet a huge
[12:32] amount of money they get very little
[12:34] engagement, and it becomes a kind of
[12:36] side project that goes nowhere in
[12:37] reality for for that business. Because
[12:40] to engage people with financial advice,
[12:41] it's got to be proactive, and it's got
[12:43] to be agentic. So people don't wake up
[12:45] and go, "Ooh, how much did I spend on
[12:47] Yes. What is it just a boring thing to
[12:49] think about? So it has to be this agent
[12:51] always on, always pushing information.
[12:53] You think about all the frontier model
[12:54] companies, it's a very reactive thing.
[12:56] It's replacing Google search for most
[12:57] people today. You have something in your
[12:59] head that you want to research, you want
[13:00] to go into. But there's so much space in
[13:03] the product cycle for it to become a
[13:05] proactive, intelligent, always-on,
[13:08] agentic thing. And that's going to
[13:10] require a lot of effort and a lot of
[13:11] training data and a lot of understanding
[13:13] of what you need to say to a user at
[13:14] what time and that's going to work.
[13:17] >> It feels to me that we're early in
[13:19] personalization. When you're saying
[13:21] it'll be very personalized, it's just I
[13:23] mean, if you look at how kind of open
[13:25] claw works underneath the hood, It's
[13:27] this static model and then a a bunch of
[13:30] flat files that it's kind of writing
[13:31] notes to itself. It's like the the movie
[13:34] Memento um where he's like writing on
[13:35] his hand um uh and that's the only
[13:38] memory he has. That's basically the AI
[13:40] models today. And I'm curious just for
[13:42] your experience trying to build
[13:44] personalized products where
[13:46] the current
[13:48] AI technology is just kind of
[13:50] fundamentally a bit resistant to
[13:52] personalization.
[13:53] >> I've never thought that
[13:55] there's definitely a meta point here of
[13:56] like we just have text, right? And like
[13:58] how does the human store memory and like
[13:59] when are we going to get to a different
[14:00] form factor for that? But in reality uh
[14:04] and what we've been doing, you can build
[14:06] a knowledge base of every single human
[14:07] like their financial aspirations, their
[14:09] financial health, their financial goals,
[14:11] every conversation they've ever had. So
[14:12] you remember Copilot did that thing a
[14:14] few months ago where it's like, "Oh, I
[14:15] do this thing recursively with LLMs."
[14:17] We've been doing that for years. Like
[14:19] that is such a powerful way to build a
[14:21] structured knowledge. I was also giving
[14:22] you a bit of for Stripe not being
[14:24] intelligent enough. And like they should
[14:26] be like knowledge base at Stripe. They
[14:28] should be every single card connected to
[14:30] every single user, who this user is, how
[14:32] much income they have, where they spend.
[14:34] So we've built that over time ever for
[14:36] every user. And then we have a
[14:38] recommender system that is thinking from
[14:40] that knowledge base. There's all of
[14:42] these opportunities for us to say things
[14:44] to users. What is the thing that's going
[14:46] to move the objective function the most?
[14:47] That's going to move that financial
[14:48] health, deliver that information, take
[14:50] that action on the back end. So I think
[14:53] I think text works as long as it's
[14:54] stored in a thoughtful uh
[14:57] clear schema and database.
[14:58] >> Mhm.
[14:59] Um
[15:01] one thing we were talking about
[15:02] backstage is
[15:03] just the concept of personality in AI is
[15:06] interesting. Like I think at the
[15:08] beginning of the field when people were
[15:10] first introducing LLMs, people might not
[15:12] have um
[15:14] predicted that personality would be such
[15:15] a big thing. But you know, we're talking
[15:16] about the new um Anthropic model Claude
[15:18] and just like what its personality is
[15:20] like or famously, you know, GPT-4 0 had
[15:23] this very controversial personality
[15:25] where, you know, some people um found it
[15:28] too sycophantic. For some people, I
[15:30] guess they really liked how sycophantic
[15:31] it was and they were annoyed when uh
[15:33] they tried to take it away from them.
[15:35] And I I get the impression that for you
[15:37] guys, the personality of uh Cleo and how
[15:41] it interacts with you is a big part of
[15:44] the differentiation. And so, what goes
[15:46] into getting the personality right? And
[15:48] for example, like do you need to tune it
[15:50] for different users? Do you try to suss
[15:51] out what personality people want? Is it
[15:53] just what it is? How do you build that?
[15:55] Have you moved beyond the army of
[15:56] comedians or is that still how you
[15:58] engineer the personality?
[16:00] >> Um I think this is one of the biggest
[16:02] things at Frontier Labs. Maybe they
[16:03] don't need to. Maybe they should be
[16:05] boring and it should be a generic, you
[16:07] know, not even personalized thing and
[16:09] they should just be there to be of
[16:09] service and intelligence. But I think
[16:11] for any brand or any company doing this,
[16:13] it moves the metrics. The personality
[16:16] and the personalization to the user
[16:18] dramatically
[16:19] changes engagement. It dramatically
[16:21] changes what a user does. So, being
[16:23] funny, being concise, writing well, all
[16:26] these things move our MAUs, it moves our
[16:28] revenue. So, we've known from like, I
[16:30] don't know, the first kind of like 3-6
[16:32] months of building this business that
[16:34] the brand and the personality and the
[16:35] tone of voice mattered a lot. So, it's
[16:38] um it's been a it was kind of linear
[16:40] supervised learning, one tone of voice.
[16:43] And then since LLMs, it is now a much
[16:45] more personalized
[16:46] uh tone of voice based on your income,
[16:48] your financial health, where you live.
[16:50] You in Boston, you in San Francisco, uh
[16:53] don't know how it talks. I want to make
[16:54] fun of John, but I shouldn't make fun of
[16:55] John in front of 1,500 people. But it
[16:58] it will talk to you um however it thinks
[17:01] uh you want to be spoken to and you can
[17:02] craft that as well.
[17:04] >> But but is your general learning that,
[17:06] you know, finance for a lot of people is
[17:07] a high-stakes topic, it's maybe they're
[17:09] nervous about it, it's a bit of a
[17:10] schlep, and so you're trying to make it
[17:12] more approachable is kind of the fun of
[17:13] fundamental personality stuff?
[17:15] >> I think these kind of great companies
[17:16] take the the inverse of take Stripe.
[17:18] Like it's it's completely archaic and
[17:20] complicated and I've got to go through
[17:22] enterprise sales to do anything in
[17:23] payments.
[17:24] Let's do the opposite. Let's make it
[17:25] really simple, dev friendly. It's going
[17:27] to be a one-click thing. It's the exact
[17:29] same You remember Monzo? Like it was
[17:30] really bad UX to do anything with a bank
[17:33] and they just made it simpler, more
[17:35] transparent, less opaque. And we've
[17:37] gone, "Okay, it's really complicated
[17:39] financial advice. We're going to make it
[17:40] really simple. It's really boring. We're
[17:42] going to make it really fun." And we've
[17:45] just taken the inverse position, which
[17:47] is such an obvious thing to say, but I
[17:48] think like
[17:50] how many founders do you see actually
[17:51] take that?
[17:53] So, I think it's worked for us.
[17:54] >> It's product contrarianism or product
[17:56] differentiation.
[17:57] >> Yeah, it's like the in the you always
[17:59] want it in the most extreme form
[18:01] generally. Like what is the biggest pain
[18:02] point of your incumbent? And like what
[18:04] am I going to do? I'm just going to
[18:06] go incredibly hard at that biggest pain
[18:08] point and make it the most delightful
[18:09] experience. So, it's a yeah, it's a hack
[18:12] for building a first product, right?
[18:13] >> Yes.
[18:14] Um
[18:16] how is the landscape of financial
[18:18] products that you advise people on
[18:20] changing? Like borrowing is some
[18:23] presumably changing somewhat
[18:25] at an industry level due to the
[18:26] emergence of BNPLs and things like this.
[18:28] I don't know is kind of the mortgage
[18:30] industry changing and how people are
[18:31] getting those here. Just yeah, I'm
[18:33] curious how you
[18:35] >> There's only so many primitives with
[18:36] money as you definitely know, right?
[18:38] Like you can borrow, you can spend. Like
[18:40] there's there's just only a finite set
[18:41] of things you can do. So, all of the
[18:43] innovation is
[18:46] It's it's it's useful, but it's slow and
[18:48] it's guided by regulators. I think, you
[18:51] know, buy now pay later is a great
[18:52] example of credit cards were this really
[18:54] bad thing for all these years. So, we're
[18:56] doing something better and something
[18:57] different, but it's not that interesting
[18:59] in my opinion generally. Hopefully, like
[19:02] the biggest thing will be stable coins
[19:03] and like how do we transact and how do
[19:05] we move away from those rails, but
[19:08] I don't find building the We build a lot
[19:10] of financial products. I shouldn't say
[19:11] this cuz all my team's work on them, but
[19:13] I find them
[19:15] constrained and slightly boring cuz they
[19:17] the limited number of primitives, but I
[19:19] think the intelligence and the advice
[19:21] If I was building Stripe, I would be
[19:23] like the intelligence, what I can give
[19:25] consumers from that would be the most
[19:26] important thing, but I guess that's also
[19:28] my wonk.
[19:30] >> Well, it's not just a limited number of
[19:31] primitives, right? It's also all these
[19:32] products are heavily regulated, and so
[19:33] they end up in kind of certain stra-
[19:35] streams. But, for example,
[19:37] do you see different like should people
[19:39] be consuming a lot of BNPL or a little?
[19:41] Like, what's um
[19:43] >> Well, they shouldn't be maximizing that.
[19:45] What happens generally for consumers is
[19:47] they'll take a credit card out and they
[19:48] will max the limit, and then they will
[19:50] stay at a max limit paying the minimums
[19:52] for 10 years. It's probably the most
[19:53] inefficient form of credit the vast
[19:55] majority of society has. So, BNPL is a
[19:57] better way to pay over actual time
[20:00] period and make it more like a term
[20:01] product.
[20:02] >> For a fixed amount of borrowing though,
[20:03] if you just use it to borrow more,
[20:04] presumably that's bad.
[20:05] >> This has been my whole raison d'être,
[20:07] you know, for a for a long period of
[20:08] time. Like, credit is such
[20:11] an important part of the economy in
[20:12] people's lives, but it's used so poorly
[20:15] by so many people. And this is why I
[20:16] think the intelligence is the
[20:18] is the answer, right? Help make people
[20:20] make better decisions about how much
[20:22] credit they consume, how much they
[20:23] spend. If you just provide financial
[20:25] advice or provide financial products
[20:27] without the advice,
[20:29] I don't want to bash Robinhood,
[20:31] but you you end up just selling products
[20:33] and trying to get the most margin, and
[20:35] it leads you down this way of like,
[20:37] "Ooh, let's do day trading. Ooh, let's
[20:39] do None of these things are bad, right?
[20:41] And they can be used in the right way. I
[20:42] do think you need some sort of
[20:43] >> You can't be purely revenue maximizing
[20:45] is your view.
[20:46] >> 100%. I think it just leads to bad
[20:48] outcomes for consumers and bad outcomes
[20:50] for the business as a whole. So, I think
[20:51] that
[20:52] I think the intelligence and the
[20:54] decision-making and helping users do it
[20:56] for them is just so critical for
[20:58] everything.
[20:59] >> If you're in charge of regulating
[21:00] financial products in the UK, what would
[21:02] you change?
[21:03] >> Ah, where do I start with the UK and its
[21:06] regulators?
[21:08] Like innovation is good. Like
[21:10] creative destruction is good. It's how
[21:12] you move every industry in the world
[21:14] along. It's what we've seen for the last
[21:15] 100 years. Creative destruction is what
[21:17] drives better outcomes for consumers.
[21:19] It's what drives better outcomes for
[21:20] businesses. So you need to enable
[21:22] creative destruction. You need to have a
[21:24] level of risk-taking to allow
[21:27] upstarts to take on incumbents. And all
[21:29] too often in the UK, it's like
[21:31] "Please come to our sandbox and let's
[21:34] work together for 2 years when a venture
[21:37] funding cycle is actually 18 months."
[21:39] And it actually them trying to be
[21:41] helpful normally constrains a company.
[21:43] I've seen so many of these little angel
[21:44] investments I've done that have tried to
[21:46] engage with the FCA, but it's just taken
[21:48] so long to to get there that they've run
[21:51] out of money and not been able to
[21:52] approve product market fit. So if you're
[21:54] a founder doing it, I actually do think
[21:56] you need to take some risk early on. I'm
[21:58] sure Stripe took some risk with his
[21:59] early clients and how he built the
[22:00] business. Don't want to get in trouble,
[22:02] John. But
[22:04] taking some risk in this sector at the
[22:06] start is a is a way to build
[22:10] something that the incumbents aren't
[22:11] going to do as well.
[22:12] >> And you think there's kind of not enough
[22:13] risk-seeking behavior in the UK or it's
[22:15] not enabled in the right way?
[22:16] >> Well, it's Yeah, go back to the
[22:18] Federalist paper the Federalist papers,
[22:20] right? You had checks and balances. You
[22:21] have state and federal.
[22:24] It's probably like the
[22:25] Read those Federalist. They're like it's
[22:27] a great insight into how you should run
[22:29] a company and it's run a country. And we
[22:31] need more of that in the UK. I see the
[22:33] Prime Minister has so much power. Number
[22:35] 10 has so much power. The regulators are
[22:37] complete have complete control of yes or
[22:40] no across 60, 70 million consumers.
[22:44] Doesn't happen in the US. We have the We
[22:45] have the courts. We have the regulators.
[22:47] We have state There's all these checks
[22:49] and balances which make America and
[22:50] capitalism work, which is why I love
[22:53] building in America and why all my users
[22:54] are in America because it's actually a
[22:56] better place to do business and it leads
[22:58] to more rational outcomes. You get
[23:00] obviously dramatic polarization and
[23:02] fights and all these things, but the
[23:03] checks and balances of the US
[23:05] institutions
[23:07] is why America is winning versus Europe.
[23:10] >> So,
[23:11] maybe moving beyond financial, um,
[23:14] regulation and just kind of more broadly
[23:16] to the business climate,
[23:17] you you think just more embrace of
[23:19] creative destruction, basically. Would
[23:21] that be the precy?
[23:22] >> If I Yeah, if I was going to really
[23:24] synthesize it, it's like we've got to go
[23:26] from a culture of
[23:28] trying to conserve our legacy and our
[23:31] past and the greatness of Britain and
[23:33] Ireland and we to a place where we go,
[23:37] "Hey, actually, we're all stagnating.
[23:38] We're all declining. We actually don't
[23:40] have much to protect at the moment. We
[23:42] actually need to take some risk. We need
[23:44] to go from a very conservative risk-off
[23:46] mindset to a we're going to build and
[23:49] we're going to build great stuff and
[23:50] we're going to take some risk and we're
[23:51] going to deploy capital, uh, all these
[23:53] pension funds, all these ISAs, all
[23:55] all these institutions that could be
[23:57] doing productive things in society, you
[23:59] need to uh, move from a a mode of, yeah,
[24:02] conservatism to to risk-on creative
[24:04] destruction.
[24:05] >> Does that
[24:06] uh, filter down into how you think about
[24:08] how people should invest both at the
[24:10] individual level and at the
[24:13] institutional level? Like, if you could
[24:15] tune how people are investing, what
[24:17] encouragement would you give?
[24:19] >> The I think the individual is, you know,
[24:21] a largely solved problem even if people
[24:22] aren't doing it. Um, the the solved
[24:24] problem is, you know, the world index
[24:26] fund, right? And that's invest in the
[24:27] S&P 500. Maybe it should get better.
[24:31] Getting a little bit tech heavy, um,
[24:32] when Stripe goes public, uh, at some
[24:34] stage, but
[24:36] that that's a almost solved problem if
[24:37] you had people making rational decisions
[24:39] there and like Cleo could dramatically
[24:40] help that. I think the the set there the
[24:43] new fund that they've set up, uh, with
[24:46] Gerstner and the the baby accounts or
[24:48] whatever, the Trump account, it's always
[24:49] the Trump accounts, isn't it?
[24:51] Um, that is a that's a good thing. Get
[24:53] people investing from your age. But on
[24:54] an institutional level, there's a
[24:56] dramatic difference between the US and
[24:58] the UK and you know, all of Europe. You
[25:00] look at our pension capital, which is
[25:01] should be the big pool of capital going
[25:03] into creative destruction,
[25:05] tiny, tiny, tiny, tiny fraction in the
[25:07] UK goes towards venture capital. I've
[25:09] got British VCs and the tier one
[25:12] European VCs,
[25:14] it's like, you know, it's the California
[25:16] pension funds are actually the LPs into
[25:17] those VCs. So, I'm not returning to the
[25:20] British state any GDP growth. It's all
[25:23] going back to California. And if you
[25:25] don't want a world which is completely
[25:27] bipolar where you can either build tech
[25:28] in China or you can build tech in the
[25:30] US,
[25:31] it's really bad for Europe if we don't
[25:33] have this creative destruction and
[25:34] ability to deploy institutional capital
[25:36] in a different way.
[25:37] >> It's an interesting point that
[25:39] yeah, there's a lot of US, I mean, it's
[25:41] not universal, but a lot of US, Canadian
[25:45] >> Yep.
[25:46] >> pension systems are a little bit in
[25:48] Australia, yeah, are invested in venture
[25:50] in a big way and much less so in the UK
[25:52] and Europe broadly.
[25:53] >> And it's worked. If you look at Canadian
[25:55] pension funds, if you look at
[25:56] Australian, I would love to be an
[25:58] Australian pensioner. Like it's
[25:59] >> Yeah, there was a news article about
[26:01] famously one of these pension funds that
[26:03] bought a lot of SpaceX a few years back
[26:05] and as you can imagine, they're feeling
[26:07] quite good this week.
[26:09] >> Um
[26:10] you
[26:11] uh you run a very scaled consumer
[26:15] uh
[26:16] uh AI products. I'm curious to talk
[26:18] about that. Well, actually first off,
[26:19] how do you make money?
[26:20] >> Uh we make money through subscriptions
[26:22] and and financial products. So, we've
[26:23] got we've got cards, we've got lending
[26:25] products, buy now pay later and wage
[26:26] access. We've got wealth products, we've
[26:28] got stocks and shares. Um so, the
[26:30] financial products make money, the
[26:31] subscription makes money, value
[26:32] accruing, and it's a freemium model.
[26:35] >> What advice do you have for people who
[26:37] are building AI products that they sell
[26:38] to consumers? Like what have you learned
[26:40] about willingness to pay, what works
[26:42] well, just acquisition, like the the
[26:45] this new space that's only existed over
[26:48] the past few years?
[26:49] >> I don't know if I did it the right way.
[26:50] Like I spent the first first four years
[26:52] in business, maybe this is Zarp, just
[26:54] doing MAUs. Like it was built a great
[26:56] product, just getting MAUs.
[26:57] >> Not focused on revenue, just focused
[26:58] >> No revenue. And everyone was like
[27:00] financial health, no revenue, this is
[27:02] great. Um that worked up until I got to
[27:04] the growth funds. They were like uh
[27:06] where's your revenue?
[27:07] Um so I don't know if I'd advise that,
[27:09] but I kind of would, you know. Like I
[27:10] would probably go back and do the same
[27:12] thing of just try and build a product
[27:14] that people are using and like. And then
[27:17] integrate the the monetization um
[27:19] afterwards. The inverse of this though
[27:21] is just make sure there's one core
[27:23] primitive like Stripe where you are
[27:25] taking, you know, a margin on something
[27:26] or there's one thing tokens, whatever it
[27:28] is, and build that from day one.
[27:31] I wouldn't
[27:33] I wouldn't do anything in the middle
[27:34] which is like
[27:36] be like half-hearted on the monetization
[27:38] strategy. Like it's either baked into
[27:40] the product 100% from day one or you
[27:42] just completely forget it and get
[27:44] consumers.
[27:45] Um on the consumer side, I think it
[27:46] works actually probably to just get
[27:48] consumers first then monetize, but I
[27:50] don't know, what do you think?
[27:52] >> Um Well, I I'm curious
[27:55] like on the consumer side of things, it
[27:57] seems like many businesses decide that
[28:00] they're going to be one or the other
[28:02] where they're going to sell on a usage
[28:04] basis like uh um uh you know, normal
[28:07] grocery store just like charge a markup
[28:09] on what you um what you buy or um in the
[28:12] US, you know, Costco has this uh famous
[28:14] model where they basically make no money
[28:16] on the actual things you buy there and
[28:18] then they just sell a um
[28:20] a $100
[28:21] uh a year subscription or it's probably
[28:23] gone up. Um a subscription membership
[28:25] subscription and uh that is where they
[28:27] make all the money that Costco makes and
[28:30] they've decided that they're not going
[28:30] to bother making money on anything you
[28:31] buy in the store, they're just kind of a
[28:33] subscription business. And do you guys
[28:35] just view it as both or you are you in
[28:37] the business of selling subscriptions or
[28:38] are you in the business of selling
[28:39] financial products?
[28:41] Or is this both?
[28:42] >> We are in both, but I think, you know,
[28:43] the interesting thing there is
[28:44] subscription has been the dominant form
[28:46] factor to monetize because of payment
[28:48] rails as well, right? Because it's
[28:50] actually hard to do micro transactions
[28:52] or lots of transactions and transactions
[28:53] fell. So, having a recurring monthly
[28:55] thing and making this a kind of
[28:57] phenomenon for for the masses
[29:00] works really well um
[29:02] for software businesses. But, I can
[29:04] definitely see a world in the future
[29:05] where
[29:07] like
[29:08] you know, you have stable coins, there's
[29:09] no friction, the payment rails actually
[29:11] work, there's no cost.
[29:12] >> Yes.
[29:13] >> Then, you move way more to the Chinese
[29:14] model, right?
[29:15] >> For for self-improvement products, I
[29:17] feel like there's also sometimes a
[29:20] kind of
[29:21] using the sunk cost dynamic in consumer
[29:23] psychology, where you know, people say,
[29:25] "I'm going to buy a gym membership and I
[29:27] am going to get in shape." And now that
[29:28] I've spent this money on the gym
[29:29] membership, I have to use it cuz I'll
[29:30] feel bad if I, you know, spent the money
[29:32] and didn't. Is there any of that dynamic
[29:34] with Cleo where people are investing in
[29:35] their own financial health?
[29:37] >> I think every there's like all this kind
[29:39] of behavioral theory in all of
[29:40] subscriptions. Like, we just added a
[29:42] third tier because
[29:45] that you know, that just worked. And we
[29:47] got this middle tier and just because we
[29:50] have three, people will pick the middle
[29:52] like
[29:53] it just there's all this kind of weird
[29:55] behavioral stuff with payments and
[29:57] subscriptions that you have to optimize
[29:58] and learn about. Um so, yeah, humans are
[30:01] kind of irrational actors and I think
[30:02] you kind of got to learn where they're
[30:04] irrational um
[30:06] to help them
[30:07] but also to build a business.
[30:08] >> Yeah, you guys are kind of like dueling
[30:10] or something, right? You're like
[30:11] weaponizing people's irrationality for
[30:13] for good rather than for evil.
[30:15] >> [laughter]
[30:16] >> Let's not write that in the press, but
[30:19] >> Thanks, John. Yeah.
[30:20] Harnessing.
[30:21] >> Yeah, there you go.
[30:22] >> Yeah, there we go. Better. We're we're
[30:23] just workshopping it. Um it kind of
[30:25] speaking of people's irrationality, you
[30:27] know, people in poker talk about this
[30:28] idea of going on tilt, where, you know,
[30:30] people um you know, may mostly have a
[30:34] very solid betting strategy and then
[30:36] they just they break at a certain point
[30:39] and they start making irrational
[30:41] decisions, uh you know, maybe after a
[30:43] losing streak or something. Does that
[30:45] also happen in
[30:47] behavior you see in the app, and then
[30:48] you're trying to kind of get people back
[30:50] on the straight and narrow?
[30:51] >> It's It's It's It's human psychology.
[30:53] It's the biggest thing, right? Like um
[30:56] money is such a personal, such an
[30:58] emotive, such a, you know, psychological
[31:00] thing. People will lose a job. People
[31:02] will have a breakup. Like we have all
[31:04] these user research interviews where you
[31:06] see someone, you know, go completely on
[31:08] tilt, and, you know,
[31:10] do things that are, you know, slightly
[31:11] irrational. That's a Yeah, we're
[31:12] definitely trying to help um in those
[31:14] circumstances.
[31:16] But it's um
[31:17] yeah, that that humans are humans in a
[31:19] way as well. But there's all these
[31:20] interesting mechanisms and features that
[31:21] we build around that.
[31:23] >> You started Cleo
[31:25] before the current wave of AI, but
[31:28] you're still a kind of small and
[31:29] fast-growing company. How AI-native is
[31:31] Cleo in how it actually works?
[31:35] Uh what's ways of working do you guys
[31:37] have that we should be borrowing from
[31:39] you guys, or people in the audience
[31:40] should be borrowing?
[31:41] >> Well, my my day-to-day is drama Like
[31:43] since probably January, February, I've
[31:46] I spend my time completely differently.
[31:48] >> Oh, please do tell. Give us the before
[31:50] after.
[31:50] >> Yeah, well, the the before was 500
[31:52] people when you'd have all these
[31:53] division leaders, and you'd talk to
[31:54] division leaders, and you'd go farm for
[31:56] information, give them your opinions,
[31:57] you have your pre-reads. And the way of
[31:59] getting information in a company was to
[32:01] talk to all of these leaders, and then
[32:02] give them your feedback, and do that.
[32:04] You don't need to do that in
[32:05] organization. I think one of the
[32:06] interesting things that you probably
[32:07] won't want to talk about is like how you
[32:09] can understand what's happening in your
[32:10] organization day-to-day. You know their
[32:13] Slack messages. You know their Notion
[32:14] docs. You know every single PR, you know
[32:17] what it is built. So, I understand, you
[32:20] know, if software is the output of all
[32:21] these companies, I know what we're
[32:23] shipping in a really visceral, clear
[32:26] way, which I didn't know before LLMs.
[32:28] >> And just very practically, how are you
[32:29] synthesizing all this information across
[32:31] the company? Like are you using a
[32:32] third-party tool? Do you guys build
[32:33] internal tools? Like how are you
[32:35] scouring the Slack channels and kind of
[32:37] ingesting on all the docs?
[32:38] >> That That
[32:40] That workflow that Karpathy described is
[32:42] what I use for so much stuff. I just
[32:43] have LLMs that go over you say every PR
[32:47] and it summarizes what that PR does and
[32:49] it grades it and it tells me what's
[32:50] going on that PR and it just builds a
[32:52] knowledge base by going over all these
[32:54] things. Goes over all of the Slack
[32:56] messages in all the channels, builds up
[32:57] a knowledge base of what is happening.
[32:58] So you take lots of disparate
[33:00] information across your entire org.
[33:01] >> Yes.
[33:02] >> You build it up into a higher level.
[33:03] >> And it's essentially a sort of
[33:05] >> captain's log. Like it's going around
[33:07] the organization with its clipboards
[33:09] taking notes.
[33:09] >> On like this dramatic scale that you
[33:11] could never have done.
[33:13] >> And then you're curating the log.
[33:14] >> Well you get humans also to input into
[33:17] that log. Their pre-reads, their their
[33:19] dashboards that they're making,
[33:20] everything they do all goes into logs
[33:22] and becomes more synthesized and
[33:23] aggregated over time. Are you doing
[33:25] that?
[33:26] >> Um I I mean I'm not doing specifically
[33:28] that, but I I think one of the
[33:30] interesting things that all
[33:31] organizations are focused on right now
[33:33] is
[33:34] like um
[33:36] consumer AI tools are phenomenally
[33:38] useful and they're trained on the kind
[33:40] of corpus of information that's out
[33:42] there and they have web search tools and
[33:44] everything and companies are trying to
[33:46] >> Yeah.
[33:47] >> internally open up the data but not too
[33:50] open you know what I mean with all their
[33:51] permissions and security tools and
[33:53] everything and so I feel like that is
[33:54] the thing that all organizations are
[33:56] reckoning with with right now. But it's
[33:59] really as you say I mean does it drive
[34:00] your internal leaders up the wall the
[34:01] fact that you are now going straight to
[34:03] the source for information?
[34:05] >> My engineering managers hate me. Like
[34:07] honestly like I can't I know I know
[34:09] who's shipping. I know like who is the
[34:12] highest velocity, highest code quality.
[34:14] I know which teams because it's a
[34:15] collection of engineers are actually
[34:17] doing great work where before I had this
[34:19] kind of it was this weird view filtered
[34:22] through all these leaders that had all
[34:23] their different biases and all these
[34:25] different incentive structures. You can
[34:27] actually get really rational, clear
[34:29] thought from these LLMs and build it up
[34:31] with contacts. So, yeah, it's like I
[34:34] think the middle layer has
[34:36] probably Cleo definitely hates me, but I
[34:39] think orgs are just going to be way
[34:40] flatter because of this and it's just
[34:42] become
[34:43] yeah, it's going to become a much more
[34:44] efficient organizational flow and
[34:45] information flow.
[34:46] >> Do you think the average number of
[34:47] people that a manager at Cleo manages
[34:50] will be different in 2 years time versus
[34:54] currently?
[34:54] >> Yeah. I've never been a massive believer
[34:56] of like
[34:57] you have to do a one-to-one with every
[34:59] single one of your direct every day. And
[35:00] I think
[35:01] >> Yeah, but when you say becoming flatter,
[35:02] like do you think that will show up in
[35:03] the numbers?
[35:06] >> I I really hope you're going to have
[35:08] less middle managers
[35:10] um as and I think orgs are going to
[35:11] definitely become flatter.
[35:13] The only like the only reason I'm
[35:15] caviating myself is like you do need to
[35:17] give junior people advice and time and
[35:19] grow and develop these people. So, I
[35:21] think there's always going to be that
[35:22] need for nurturing and maybe
[35:25] it's done in a different way, but I
[35:27] think those layers and layers of
[35:30] people and people and people uh it's
[35:31] probably half the Stripe uh team uh full
[35:34] inside Cascade in the room, but I think
[35:36] that has to to change um and maybe we
[35:39] just get to do more stuff, right?
[35:40] Instead of like more hierarchical, fewer
[35:42] business units, maybe you just have
[35:44] way way way more bets, way way more
[35:46] business units and it becomes much more
[35:49] organic and much flatter.
[35:50] >> I think you possibly yeah have that
[35:52] because you can have more impact from a
[35:54] small number of people. Uh I think the
[35:55] thing a lot um people have been
[35:57] wondering as well that I think is very
[35:58] interesting is when you talk about your
[35:59] team and your people, do you end up with
[36:01] more of a an apprenticeship model
[36:04] because it's different if you have like
[36:05] one senior person with eight junior
[36:07] people, then it's maybe kind of the
[36:09] classic uh org chart view. Whereas if
[36:11] you have one senior person with one
[36:12] junior person, then you can do much more
[36:14] of a traditional kind of knowledge
[36:16] transmission uh apprenticeship model.
[36:18] So, I think
[36:19] >> I think the I think the inverse is like
[36:20] one person with like 36 like uh I'm so I
[36:23] hire all these grads from like UCLA and
[36:25] Cambridge that done their machine
[36:26] learning masters. They are so they are
[36:29] like fully AI pill. They've been doing
[36:31] it from like their A-levels, right? Like
[36:33] it's it's crazy how good they are with
[36:36] these tools. So, I think you're going to
[36:37] want more junior people that have had
[36:39] the learning and experience in LLMs from
[36:41] these institutions and are really pill.
[36:43] And then they are just dramatically,
[36:46] they're managing a fleet of agents to do
[36:48] things. So, like
[36:49] in software, you want more and more
[36:51] software, right? But you want it
[36:52] directed to the right things. So, you
[36:54] need great taste makers that can run
[36:57] lots and lots of these parallel agents
[36:59] and recursion, just more and more and
[37:00] more tokens. So, you want as many
[37:03] people, I think, as possible
[37:05] at a lower level with good taste to run
[37:07] as many agents as possible. I I like the
[37:10] idea that I can take 2,000 bets next
[37:12] year instead of like the 10 that I took
[37:14] last year.
[37:15] >> Yes.
[37:16] >> That's the world I would love to live
[37:17] in.
[37:18] >> Very cool.
[37:18] >> We'll see.
[37:19] >> [laughter]
[37:20] >> Last question. What's your most
[37:23] contrarian AI take at the moment?
[37:26] >> Um
[37:28] I'm very AI pill, so it's hard to be
[37:30] like absolutely contrarian at the
[37:32] moment.
[37:33] Uh
[37:34] I I I think the SAS pop apocalypse, like
[37:37] Frontier Labs dominating everything
[37:39] every tweet is like they've just
[37:41] destroyed X industry with their little
[37:43] wrapper. There's so much work that goes
[37:45] into building a great business like
[37:47] Stripe or like anyone else. Like there's
[37:48] so much that you need to know.
[37:50] How much have you learned about payments
[37:51] that no one in the world needs
[37:53] >> No one should have to learn.
[37:55] >> It is awful. Too much.
[37:56] >> Way too much, but there's so much of
[37:58] that and so much craft that goes into
[38:00] building a great consumer,
[38:02] business-to-business, or
[38:03] business-to-consumer products that
[38:05] you're going to have you're still going
[38:06] to have great software companies that
[38:07] are like completely vertical and really,
[38:09] really deep. And this kind of idea that
[38:11] someone wrote a prompt and they've just
[38:13] got a Frontier model that's going to
[38:14] kill everything is wildly overblown and
[38:17] investors are just
[38:18] the silliest, most irrational people
[38:20] I've ever met in my life and I can't
[38:21] believe they have all
[38:22] >> So we are kind of over extrapolating
[38:24] from the
[38:25] >> They have no idea what's going on. They
[38:26] don't have any technical knowledge at
[38:28] all and they are they are in a world of
[38:30] they don't understand. So they're in a
[38:32] world of we're going to sit on the fence
[38:33] and just put money into the frontier
[38:34] labs.
[38:36] And stripe apparently.
[38:38] >> [laughter]
[38:38] >> And that's all they're going to do. Um
[38:40] But yeah, I think like that rationality
[38:42] will play out in a couple of years and
[38:43] you'll see valuations, multiples The
[38:46] economy is driven by software. It has
[38:47] been for the last 30 years. We want more
[38:49] software companies. That is where GDP
[38:51] growth is going to come from. We want
[38:53] more creative destruction. That's what
[38:54] AI is going to lead to. Like the
[38:56] abundance is not contrarian take, but
[38:58] I'm pro abundance.
[38:59] >> Yeah.
[39:00] That's a good note to end on. You heard
[39:02] it here. Lots more creative destruction
[39:04] to come and the story is not yet written
[39:07] and it's not just, you know, a small
[39:08] number of firms that'll be shipping
[39:10] everything useful.
[39:12] With that, um that brings our
[39:13] programming for Tour London at 2:00 to a
[39:16] close. So thank you all for coming this
[39:18] year. And we are going to roll into a
[39:20] reception which we're having out in the
[39:22] Expo Hall. And we can't wait to see you
[39:24] guys next year.
[39:26] Thanks, Barney.
[39:27] >> Thanks, Luke.
[39:28] It's fun.
[39:28] >> Thanks. Good luck.