Will AI Models Ever Compensate Creators?

How We Access The Best Companies

Subscribe to stay ahead of technology trends. Never miss future editions. Ben Miller [https://www.linkedin.com/in/benjamin-miller-b5b79a4/], CEO and Co-Founder at Fundrise [https://fundrise.com/], joins NEW ECONOMIES to explore the future of investing in an AI-driven world. From democratizing private markets to backing the next generation of technology companies, Ben explains why software is entering a new era of disruption, and how AI could reshape everything from work and housing to healthcare and human longevity. About Fundrise: Fundrise is the largest direct-to-consumer alternative asset manager with more than 385,000 active investors, 2.1 million platform users, and $3.3 billion in assets across real estate, venture, and private credit. In this episode, we explore why Fundrise expanded beyond real estate into venture investing, how Ben thinks about building with conviction instead of institutional consensus, and why some of the best investment decisions come from waiting rather than deploying capital on schedule. We also go deep on how AI is reshaping software, venture, and the broader economy — from why application-layer businesses may become harder to sustain, to why capital is increasingly concentrating around models, compute, and infrastructure. If that’s not enough, we also discuss why venture is far more relationship-driven than most people realize, why investors often overstate their impact relative to founders, and why Ben believes the next great opportunities won’t come from another consumer app — but from applying AI to the physical world through biology, materials, energy, and longevity. Watch or listen now on YouTube [https://www.youtube.com/@NEWECONOMIESPOD], Apple Podcasts [https://podcasts.apple.com/us/podcast/big-ideas-by-new-economies/id1829098542], and Spotify [https://open.spotify.com/show/3oVCdw4btnIL1mWGarCT7i] Download the transcript Timestamps (0:00 [https://www.youtube.com/watch?v=7W-P0lS_hCQ]) Ben Miller (1:42 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=102s]) Democratizing Access To Private Markets (9:50 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=590s]) Venture vs. Real Estate (12:48 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=768s]) Getting Access To Companies (15:07 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=907s]) Venture Is Changing (20:10 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=1210s]) What Happens Next? (22:10 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=1330s]) Companies Going Public (28:16 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=1696s]) Where Are The Next Opportunities? (31:22 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=1882s]) The Impact of Longevity (33:30 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=2010s]) Tough Categories Right Now (35:15 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=2115s]) Thoughts On Vibe Coding Tools (36:12 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=2172s]) Ollie Joining As Chief of Staff (37:35 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=2255s]) How Ben Uses AI (40:53 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=2453s]) The Next Big Act For Fundrise (44:22 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=2662s]) What Categories Would Ben Build In? (46:13 [https://www.youtube.com/watch?v=7W-P0lS_hCQ&t=2773s]) Rapid Fire Our notes from this conversation * Fundrise was built as a reaction to the financial system. The idea didn’t start with real estate — it started with distrust. After living through the 2008 financial crisis firsthand, Ben’s view became simple: people should be able to own real assets directly instead of relying entirely on financial institutions. * Private markets became consumer products. Fundrise saw the opportunity earlier: It took institutional investing models — private equity, real estate funds, venture — and rebuilt them for individuals. The thesis wasn’t to invent a new asset class. It was to open access to one that already existed. * Great investing often means not doing what you said you would. The team raised venture capital to invest in tech — and then barely invested for a year. Instead of deploying because markets expected it, they waited. Flexibility became an advantage over institutional pressure. * Access in venture is more random than people admit. From the outside, venture looks like a system. Inside, it often looks like relationships, timing, and proximity. Many of the best investments happen through unexpected connections rather than structured processes. * Founders create outcomes. Investors mostly provide fuel. The venture industry talks heavily about value-add. Ben’s view: teams build companies. Capital matters. Advice occasionally matters. But execution compounds more than introductions. * AI is making software easier — and company building harder. As models become more capable, application layers become vulnerable. Product roadmaps compress. Builders increasingly compete not just with startups, but with the platforms underneath them. * Capital is concentrating faster than people expect. AI isn’t only changing software — it’s redirecting capital. Trillions are flowing into models, compute, and infrastructure, creating second-order effects across housing, credit, real estate, and the broader economy. * The next breakthrough isn’t digital — it’s physical. The most exciting opportunities may not be chat interfaces or copilots. They may come from applying AI to biology, materials, medicine, energy, and the physical world itself. * The future belongs to people willing to suffer for the hard decisions. Ben’s framework for leadership is simple: the best decisions are often the ones that are personally painful. Building means choosing uncertainty, absorbing pressure, and taking responsibility before outcomes are obvious. * Learning remains the ultimate competitive advantage. The next company, sector, or wave rarely looks obvious in advance. Curiosity, experimentation, and being willing to look outside your category matter more than defending a fixed identity. Links Subscribe to NEW ECONOMIES on YouTube [https://www.youtube.com/@NEWECONOMIESPOD] Follow Ollie on X (https://x.com/ollieforsyth [https://x.com/ollieforsyth]) Follow Ben on X (https://x.com/BenMillerise [https://x.com/BenMillerise]) Related previous episodes If you enjoyed this episode, help sustain our work by clicking ❤️ and 🔄 at the top of this post. Get full access to NEW ECONOMIES at www.neweconomies.co/subscribe [https://www.neweconomies.co/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

Why We Sold To Grammarly | Rahul Vohra

Subscribe to stay ahead of technology trends. Never miss future editions. Why email never died — and why Superhuman is betting on voice, AI, and the future of work Rahul Vohra [https://www.linkedin.com/in/rahulvohra/], founder of Superhuman [https://superhuman.com/] and now CEO of Superhuman Mail [https://superhuman.com/products/mail] inside the newly formed Superhuman group, joins NEW ECONOMIES on why email remains the most important layer of modern work, how AI is transforming productivity beyond the inbox, and why distribution and focus matter more than technical moats in the age of infinite software. In our latest podcast episode with Rahul, we unpack Superhuman’s eleven-year journey — from the contrarian decision to reinvent email when everyone said it was dead, to building one of Silicon Valley’s most iconic productivity brands and eventually becoming the foundation for a much bigger ambition: the AI-native productivity suite. We also explore why voice could become the default interface for knowledge work, how AI assistants are becoming a new growth channel for software companies, and why Rahul believes the next generation of winners won’t be defined by who writes the best code — but by who owns distribution, executes relentlessly, and knows what not to build. If that’s not enough, we go deep on the acquisition story that led Grammarly to rename the entire company around Superhuman, why email continues to outperform every prediction of its demise, and what building the productivity bundle of the future actually looks like. Watch or listen now on YouTube [https://www.youtube.com/@NEWECONOMIESPOD], Apple Podcasts [https://podcasts.apple.com/us/podcast/big-ideas-by-new-economies/id1829098542], and Spotify [https://open.spotify.com/show/3oVCdw4btnIL1mWGarCT7i] Download the transcript Timestamps (0:00 [https://www.youtube.com/watch?v=W8dy67rGzo8]) Rahul Vohra(1:44 [https://www.youtube.com/watch?v=W8dy67rGzo8&t=104s]) Why Go After Disrupting Email(4:22 [https://www.youtube.com/watch?v=W8dy67rGzo8&t=262s]) Will Email Still Stay Relevant?(9:20 [https://www.youtube.com/watch?v=W8dy67rGzo8&t=560s]) The Impact of Voice(14:20 [https://www.youtube.com/watch?v=W8dy67rGzo8&t=860s]) PLG: Sent by Superhuman(18:57 [https://www.youtube.com/watch?v=W8dy67rGzo8&t=1137s]) Why Moats Are Becoming Increasingly Hard to Build(24:30 [https://www.youtube.com/watch?v=W8dy67rGzo8&t=1470s]) How Does Superhuman Group Stay Focused?(28:55 [https://www.youtube.com/watch?v=W8dy67rGzo8&t=1735s]) Inside Superhuman(33:20 [https://www.youtube.com/watch?v=W8dy67rGzo8&t=2000s]) Missing Products from the Bundle(36:52 [https://www.youtube.com/watch?v=W8dy67rGzo8&t=2212s]) The Acquisition(45:45 [https://www.youtube.com/watch?v=W8dy67rGzo8&t=2745s]) Ollie Joining as Chief of Staff(47:45 [https://www.youtube.com/watch?v=W8dy67rGzo8&t=2865s]) Angel Investing Our notes from this conversation * Email is still the most important protocol at work. Every few years someone declares email dead — and every few years they’re wrong. Email remains identity, authentication, and the default layer for company communication. The interface will change. The infrastructure probably won’t. * Voice is becoming the new keyboard. The breakthrough isn’t transcription — it’s intent. Instead of writing emails, scheduling meetings, and prompting AI manually, people will increasingly speak outcomes and let software execute. Work becomes orchestration. * The biggest moats aren’t technical anymore. Software is becoming cheaper and easier to build. Features get copied faster than ever. Distribution, trust, brand, and knowing exactly what not to build are becoming the new defensibility. * Distribution compounds. Products alone don’t. The winners won’t necessarily be the teams with the smartest models — they’ll be the teams that own attention, create habits, and get embedded where users already work. Distribution has become product. * AI changes interfaces before it changes infrastructure. Voice, agents, and AI-native workflows will reshape how we interact with email, docs, and software — but the systems underneath often survive much longer than people expect. * Focus becomes more valuable as building gets easier. When the cost of creation trends toward zero, restraint becomes leverage. The companies that win won’t build the most — they’ll build the few things that matter. * The next growth channel is AI itself. Users are no longer only discovering products through search, social, or sales. Increasingly, AI assistants recommend, connect, and even activate software on behalf of users. Tools such as The Prompting Company [https://promptingcompany.com/] help companies get cited in AI models for example. * The future isn’t humans or AI — it’s humans with AI. The products that endure won’t remove people from work. They’ll amplify judgment, creativity, and decision-making while automation handles the repetitive layers underneath. Links Subscribe to NEW ECONOMIES on YouTube here [https://www.youtube.com/@NEWECONOMIESPOD]. Follow Ollie on X (https://x.com/ollieforsyth [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa1NEYnBoMjJCTzl2SkgwWXpJX1Z6cXU4SVVfQXxBQ3Jtc0trVW9adnpoY0hYMmxGb1YzRG9DMlFKWE1FTlljRDRWMG1lZ0hLd1J1cG5MRXRTNVA0bHVvZUFZTHF3OGJpUTBvb0RLNl8xamZsVjYxYl8ta19PQ0JsRi1CaFpxTjBadGFmWlhzdlFLSjhXNUI1NmhMSQ&q=https%3A%2F%2Fx.com%2Follieforsyth&v=W8dy67rGzo8]) Follow Rahul on X (https://x.com/rahulvohra [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqazJ4bXFaT3F5YXJDOE9idFlfbElaZjB5ajBnZ3xBQ3Jtc0tudUVxRjJPUzVLWWxrMEJXMEJNTjE5M3Jhb2wtRUNRc3lCYXdKOUhfY1hpZHlJc0VpY3VsdjJlRTdwZmlia1lHcUNQb1VINGJ4ZGs5Y3FWLWpiYXczN3ZkUFdnZkdEdHlMMEFZU0Jzd1NYTVpkYjBrTQ&q=https%3A%2F%2Fx.com%2Frahulvohra&v=W8dy67rGzo8]) Sign up to Superhuman (https://superhuman.com [https://superhuman.com/]) Related previous episodes If you enjoyed this episode, help sustain our work by clicking ❤️ and 🔄 at the top of this post. Get full access to NEW ECONOMIES at www.neweconomies.co/subscribe [https://www.neweconomies.co/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

Replit's President & Head of AI | Michele Catasta

Subscribe to stay ahead of technology trends. Never miss future editions. Why I built the coding tool everyone dismissed — then watched it take over the Fortune 500 Michele Catasta [https://www.linkedin.com/in/pirroh/?skipRedirect=true], President and Head of AI at Replit, joins NEW ECONOMIES on why vibe coding is no longer just for hobbyists, how Replit went from a side project to having 85% of the Fortune 500 as users, and why 2026 is the year everyone becomes an agent manager. In our latest podcast episode with Michele, we discuss Replit's origin story — a fifteen-year journey that started as an open source side project in 2011 and spent years building infrastructure in obscurity before the AI unlock that changed everything — and how launching the very first vibe coding agent on the market, before the term even existed, put Replit at the centre of a category it invented. We also unpack why the SaaS apocalypse is real but overblown, why technical moats don't matter as much as execution moats, and how a crucible encounter with Replit's founder Amjad over a primitive AI demo set the course for what the product would eventually become.If that’s not enough, we also explore why Replit scrambled an enterprise sales team almost overnight after Fortune 500 IT departments started knocking, the Visa partnership that lets anyone monetize a product they built in a single prompt, and why Michele believes the coding problem is almost solved — and what that means for where Replit goes next. Watch or listen now on YouTube [https://www.youtube.com/@NEWECONOMIESPOD], Apple Podcasts [https://podcasts.apple.com/us/podcast/big-ideas-by-new-economies/id1829098542], and Spotify [https://open.spotify.com/show/3oVCdw4btnIL1mWGarCT7i] Download the transcript Timestamps (0:00 [https://www.youtube.com/watch?v=VbQBlD22NNQ]) Michele Catasta(1:25 [https://www.youtube.com/watch?v=VbQBlD22NNQ&t=85s]) The State of AI(3:25 [https://www.youtube.com/watch?v=VbQBlD22NNQ&t=205s]) The Impact of AI Companies Going Public(6:17 [https://www.youtube.com/watch?v=VbQBlD22NNQ&t=377s]) What Michele Is Most Excited About(8:50 [https://www.youtube.com/watch?v=VbQBlD22NNQ&t=530s]) Replit's Founding Story(18:40 [https://www.youtube.com/watch?v=VbQBlD22NNQ&t=1120s]) Where Is Vibe Coding Going Next?(21:00 [https://www.youtube.com/watch?v=VbQBlD22NNQ&t=1260s]) The Role for PMs Today(26:07 [https://www.youtube.com/watch?v=VbQBlD22NNQ&t=1567s]) What Are Agent Managers?(33:42 [https://www.youtube.com/watch?v=VbQBlD22NNQ&t=2022s]) Are Technical Moats Relevant?(36:31 [https://www.youtube.com/watch?v=VbQBlD22NNQ&t=2191s]) Visa Partnership(40:05 [https://www.youtube.com/watch?v=VbQBlD22NNQ&t=2405s]) Ollie Joining as Chief of Staff(43:48 [https://www.youtube.com/watch?v=VbQBlD22NNQ&t=2628s]) How to Stay Disciplined(46:27 [https://www.youtube.com/watch?v=VbQBlD22NNQ&t=2787s]) Rapid Fire Round Our notes from this conversation 1. Launch before the category has a name. Replit shipped a vibe coding agent months before the term even existed. They didn’t wait for validation — they built, launched, and let users define the market. Lesson to founders is to just launch fast. 2. Sometimes being early means writing the playbook, which is totally okay! Product–market fit as we know can takes ages to figure out. For a decade, Replit looked technically strong but commercially stuck. Those years built the infrastructure and conviction that made the AI moment possible. Remember, successes very rarely happens overnight. 3. Enterprise wasn’t actually a strategy for the team - their users pulled them there. When employees started building internal tools, IT followed. Strong PLG can create demand before sales does. 4. Technical moats fade. Execution moats compound. Features can be copied. Judgment can’t. A decade of learning what breaks, scales, and actually matters becomes the real advantage. 5. Coding is becoming the easy part. The harder problem is everything around it — integrations, payments, governance, and infrastructure. The product becomes the platform. 6. 2026 is the year of ‘’the agent manager.’‘ Work shifts from creating everything yourself to directing, reviewing, and orchestrating multiple agents. The operating model changes before the job titles do. Links Subscribe to NEW ECONOMIES: ‪@NEWECONOMIESPOD‬ [https://www.youtube.com/@NEWECONOMIESPOD]Follow Ollie on X (https://x.com/ollieforsyth [https://x.com/ollieforsyth]) Follow Michele on X (https://x.com/pirroh [https://x.com/pirroh]) Sign up to Replit: (https://replit.com [https://replit.com]) Related previous episodes If you enjoyed this episode, help sustain our work by clicking ❤️ and 🔄 at the top of this post. Get full access to NEW ECONOMIES at www.neweconomies.co/subscribe [https://www.neweconomies.co/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

Inside Mercury's Founding Story | Co-Founder & CEO Immad Akhund

Subscribe to stay ahead of technology trends. Never miss future editions. Why I built banking for America's startups — then rebuilt it around AI Immad Akhund [https://www.linkedin.com/in/iakhund/], Co-Founder & CEO at Mercury [https://mercury.com/], joins NEW ECONOMIES on banking one in three U.S. startups, raising $200M without needing a dollar of it, and why the legacy banking system was never going to win. In this episode, we discuss Mercury’s origin story — launched in 2019 when the entire industry told founders that nobody would trust a startup with their money — and how a million-dollar deposit arrived within four days of launch from someone Immad had never spoken to. We dig into why incumbent banks were always going to lose this fight, why AI makes their position ten times worse, and how Mercury is now rebuilding its entire product around the idea that your bank should live inside whatever AI tool you already use.We also explore why Immad dropped all one-on-ones after watching Jensen Huang run NVIDIA with 60 direct reports, the Amazon “working backwards” process that mapped out Mercury’s entire AI roadmap from a single doc, and why the fintech companies that planted seeds in 2017 are only now bearing fruit. Watch or listen now on YouTube [https://www.youtube.com/@NEWECONOMIESPOD], Apple Podcasts [https://podcasts.apple.com/us/podcast/big-ideas-by-new-economies/id1829098542], and Spotify [https://open.spotify.com/show/3oVCdw4btnIL1mWGarCT7i] Download the full transcript: Timestamps (0:00 [https://www.youtube.com/watch?v=t3BA7u4qg5k]) Immad Akhund(2:35 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=155s]) Why Raise $200M?(3:55 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=235s]) Why FinTech Is Having a Moment(6:02 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=362s]) How Has AI Impacted Mercury?(10:25 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=625s]) What Is Defensibility Today?(13:29 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=809s]) Mercury Finding Product-Market Fit(15:22 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=922s]) Legacy Banks Never Caught Up(19:22 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=1162s]) Inside Mercury's Product Team(23:56 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=1436s]) The Nuclear Power of Talent(26:05 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=1565s]) Is AI Moving Too Fast?(29:00 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=1740s]) Keeping Up-to-Date with AI(31:20 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=1880s]) Ollie Joining Immad as Chief of Staff(33:45 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=2025s]) Our Latest Product Features(35:45 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=2145s]) Immad's Interest in Angel Investing(38:20 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=2300s]) Today's Underappreciated Opportunities(40:36 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=2436s]) AI Wrappers: Will They Last?(42:34 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=2554s]) Why Is Consumer So Hard?(44:17 [https://www.youtube.com/watch?v=t3BA7u4qg5k&t=2657s]) Immad's Quick-Fire Round Our notes from this conversation 1. Raise when you don’t need to — and the terms will show it Mercury has been profitable for four years. That single fact changed everything about the Series D. When you’re not desperate, you get to choose your investors, your timing, and your narrative. Immad has watched enough founders raise under duress to know the difference — and deliberately built Mercury to a position where fundraising is a strategic move, not a survival one. The best negotiating leverage is not needing the deal. 2. Legacy banks lost because their incentives were always wrong Deposit banking is a cost center for incumbent banks. Their real product is loans. That single structural fact explains almost everything: why they underinvest in product, why they charge fees instead of building features, why their “engineering” teams are actually IT teams stitching together third-party vendors. They weren’t slow to adapt — they were optimized for something else entirely. Mercury was always competing on a different game board. 3. Trust isn’t a brand asset. It’s an infrastructure layer Within four days of launch, someone Immad had never spoken to wired a million dollars into a Mercury account. That moment signaled something real — but it took seven more years to get customers holding $400M in their accounts. Trust compounds slowly and is almost impossible to manufacture quickly. It’s also, eventually, one of the most durable moats in financial services. The product is the interface. The trust is the product. 4. AI made the incumbent problem ten times worse If legacy banks couldn’t keep up with Mercury’s pace over the last decade, they have no chance now. The window for meaningful product decisions has shrunk from years to months. Launching an MCP integration, shipping an AI-native feature, rebuilding a workflow around an agent — these are things Mercury can do in weeks. A bank operating on a core banking vendor’s release cycle cannot. The faster the world moves, the more permanently the gap widens. 5. The paradigm shifts every six months — that’s the feature, not the bug A year ago, nobody was seriously talking about agents living on your machine and connecting to every service you use. Now it’s Mercury’s central product thesis. Immad isn’t trying to predict which paradigm comes next — he’s building an organisation that can absorb the shift when it arrives. Curiosity and optimism aren’t soft skills. They’re survival mechanisms for operating in an environment where the rules rewrite themselves annually. Links Subscribe to NEW ECONOMIES on YouTube [https://www.youtube.com/@NEWECONOMIESPOD]. Follow Ollie on X (https://x.com/ollieforsyth [https://x.com/ollieforsyth]) Follow Immad on X (https://x.com/immad [https://x.com/immad]) Join Mercury (https://mercury.com [https://mercury.com]) Try Mercury Insights (https://mercury.com/insights [https://mercury.com/insights]) Our NEW MEDIA Community (new-media.co [http://new-media.co]) Related previous episodes If you enjoyed this episode, help sustain our work by clicking ❤️ and 🔄 at the top of this post. Get full access to NEW ECONOMIES at www.neweconomies.co/subscribe [https://www.neweconomies.co/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

Inside Gusto's Founding Story | Co-Founder & CTO Eddie Kim

Subscribe to stay ahead of technology trends. Never miss future editions. Why I built America's most-loved payroll company then reinvented it with AI Eddie Kim [https://www.linkedin.com/in/edawerd/], Co-Founder and CTO at Gusto [https://gusto.com/], joins NEW ECONOMIES on cracking the small business market, keeping all three co-founders for 15 years, and why he just built the most important product of his career in eight weeks. Watch or listen now on YouTube [https://www.youtube.com/@NEWECONOMIESPOD], Apple Podcasts [https://podcasts.apple.com/us/podcast/big-ideas-by-new-economies/id1829098542], and Spotify [https://open.spotify.com/show/3oVCdw4btnIL1mWGarCT7i] Download the full transcript: Eddie Kim [https://www.linkedin.com/in/edawerd/] is the co-founder at Gusto [https://gusto.com/], the small business platform that just crossed a billion dollars in annual revenue serving over 500,000 companies across payroll, benefits, HR, and compliance. A two-time YC founder who met his co-founders at Stanford and at a half marathon starting line, Eddie has spent 15 years proving that the most unglamorous problems in business are often the most valuable ones to solve. In this episode, we explore what it actually takes to build a category-defining company in a space nobody wanted to touch — and why Eddie believes he just built the most important product of his career — Gusto Cofounder: The AI Teammate Built for Small Business [https://gusto.com/product/cofounder]. We also explore the blank canvas problem holding AI back from mainstream adoption, why the distinction between engineer and designer is disappearing, and how a team of five people went from zero code to full launch in eight weeks. Timestamps (0:00 [https://www.youtube.com/watch?v=k6nnoojGpxI]) Eddie Kim, Co-Founder at Gusto (5:40 [https://www.youtube.com/watch?v=k6nnoojGpxI&t=340s]) Lessons from Y Combinator (9:30 [https://www.youtube.com/watch?v=k6nnoojGpxI&t=570s]) 15+ years on co-founder relationships (15:00 [https://www.youtube.com/watch?v=k6nnoojGpxI&t=900s]) How to give feedback to your co-founders (17:45 [https://www.youtube.com/watch?v=k6nnoojGpxI&t=1065s]) The early days at Gusto(21:10 [https://www.youtube.com/watch?v=k6nnoojGpxI&t=1270s]) Gusto’s new product: Gusto Cofounder (33:05 [https://www.youtube.com/watch?v=k6nnoojGpxI&t=1985s]) How to launch new features (38:15 [https://www.youtube.com/watch?v=k6nnoojGpxI&t=2295s]) The rise of solo entrepreneurs (41:25 [https://www.youtube.com/watch?v=k6nnoojGpxI&t=2485s]) How to avoid distractions (45:20 [https://www.youtube.com/watch?v=k6nnoojGpxI&t=2720s]) How Gusto would launch today from scratch(47:00 [https://www.youtube.com/watch?v=k6nnoojGpxI&t=2820s]) Lightning fire round Our notes from this conversation 1. Boring problems are the best problems — if you can stomach the grind In 2011, the hottest companies were chasing eyeballs. Mobile, social, local. Nobody wanted to work on payroll. Hiring was nearly impossible, and one of the category’s own pioneers told the Gusto founders to their faces: don’t do it. That discouragement was actually the signal. The problems everyone avoids are exactly the ones worth solving — because if you can crack them, the competitive field is almost empty. 2. The co-founder relationship is built over years, not conversations All three Gusto co-founders are still at the company 15 years later — a genuinely rare thing. What makes it work isn’t a communication framework or a weekly check-in cadence. It’s shared values, accumulated trust, and the quiet confidence that comes from having survived a hundred disagreements and come out the other side. Real directness — saying what you actually think — only becomes possible once you’ve built that foundation. You can’t shortcut it. 3. The blank canvas problem is AI’s biggest obstacle The reason most small business owners can’t harness AI isn’t capability — it’s context. Install Claude Code or open a frontier model and you’re staring at infinite possibility with no clear starting point. That’s paralyzing. The insight behind Gusto Co-Founder is that AI becomes transformative the moment it’s anchored to a specific domain, with real data and real problems already loaded in. Generic intelligence is a tool. Contextual intelligence is a co-founder. 4. Trust is infrastructure — and it takes 15 years to build Gusto couldn’t have launched its AI co-founder product on day one. The depth in payroll, benefits, compliance, and tax took over a decade to accumulate. That history — 500,000+ customers, millions of data points on what makes small businesses succeed or fail — is what makes the product genuinely useful rather than just technically impressive. The lesson: trust and data are compounding assets. The longer you stay focused on one problem, the harder your moat becomes to replicate. 5. The future of building is builders — not roles The team that built Gusto Co-Founder was five people: four engineers and a designer. No roadmaps, no sprint planning, no documentation. The designer wrote code. The engineers made design decisions. They ran a permanent Zoom call instead of meetings. In eight weeks, they went from zero to launch. That’s not a fluke — it’s a preview. AI is erasing the gaps between specialties. The builder mindset is the only identity that matters now. 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