Xero CEO: The Strategy to Achieve 31% Revenue Growth in 12 MonthsSukhinder Singh Cassidy, CEO of Xero, explains how the cloud accounting platform reached $2.7 billion in revenue, 31% growth, and 5 million customers by cracking the US through the Milio acquisition, building product from the US, and narrowing focus to a "US unicorn" number. She details why the US took 20 years—Intuit's entrenched home-market advantage and the need for local engineers—and why she treats "respected vs. liked" as a false choice, backing layoffs with data and speed. On AI, she argues thin application wrappers can't replicate Xero's tens of thousands of edge cases, regulatory connections, payment rails, and trusted data across 180 countries, making infrastructure the real moat. She also answers whether accountants stay relevant by pointing to Client Advisory Services, and describes the customer spectrum from AI-native builders to those needing basic AI chat support.Aug 16, 2026 · 52:18 · 420 views
Canva Co-Founder: AI Is Useless Without This 1 SkillCameron Adams, co-founder of Canva—now used by 250 million people monthly—argues that taste, not AI, is the new differentiator for creators. Adams describes Canva's founding story, where they delayed launch to polish the user experience, turning early social media managers into fanatical ambassadors. He explains that AI enables exploring ideas at scale, but the key skill is having the judgment to choose the right option and respond quickly to trends. Adams details Canva's AI evolution from text-to-image in 2022 to now solving end-to-end workflows like marketing campaigns. He also shares insights on co-founder dynamics, noting that Mel and Cliff excel at recognizing moments of change and rallying around a vision. The episode covers creators' need for taste, responsiveness, and managing multiple AI tools to stay relevant.Jul 29, 2026 · 57:30 · 35.8K views
a16z Partner: Hollywood Is Secretly Replacing Films With AIJustine Moore, a16z partner and early backer of ElevenLabs, explains why AI microdramas — short, vertical soap operas — are becoming the fastest-growing entertainment format, with China's microdrama market now larger than its domestic box office. She argues model quality has reached 90-95% of filming, making it cheaper and faster, and professional storytellers are now using it to create compelling narratives. Amazon and Netflix have announced programs for fully AI-generated animations. ElevenLabs, which she backed at Series A, has crossed $500M in ARR. She highlights consumer agents like Town that automate tasks such as warm intros and expense forwarding, and sees the biggest opportunity in serving less technically sophisticated users and vertical industries like marketing and architecture.Jul 23, 2026 · 50:27 · 1.2K views
$1M to $100M ARR: What It ACTUALLY Takes to ScaleMaor Shlomo, founder of Base44, and Mark Tluszcz, Wix chairman, reveal how Base44 grew from a solo side project to $1M revenue in three weeks and $150M ARR within a year of Wix's 2025 acquisition, arguing that owning the full tech stack—including a custom AI model—is essential for vibe coding platforms. They explain Base44's origin as a tool for non-technical users to build custom software, the decision to stay bootstrapped until partnering with Wix, and the launch of their own open-source-derived LLM (Base One) to reduce costs and improve product decisions. The episode covers why they rejected reliance on third-party models, how they plan to update the model daily via reinforcement learning, and their vision for adding distribution and marketing AI co-pilots. They also share the chaotic early days, including a false hack scare during a family wedding, and predict that vibe coding will shift from building to ideation and enterprise adoption of internal tools.Jul 21, 2026 · 56:32 · 11.1K views
Reid Hoffman, LinkedIn Founder: 99% of People Are Using AI WrongReid Hoffman, LinkedIn co-founder, argues most people underutilize AI by treating it as a search engine rather than an agentic workforce, predicting a shift where humans become managers of AI agent teams. He explains that Blitzscaling today means using AI to rapidly build and discard prototypes, while distribution remains a critical moat for startups. Hoffman warns that negative AI perception in the US and Europe risks ceding leadership to Asia, which embraces the cognitive Industrial Revolution. He highlights the importance of taste and judgment as skills that AI amplifies rather than replaces, and contrasts Anthropic's enterprise focus with OpenAI's consumer strength. Drawing from his decade on Microsoft's board, he shares Satya Nadella's lessons on rebuilding culture, corporate partnerships, and treating AI agents as employees that work for the company. Hoffman also spotlights applications in drug discovery (Manus AI) and personalized AI to maintain human connections.Jul 19, 2026 · 1:00:42 · 2.3K views
Mark Manson: AI is a Better Writer Than You But Here’s What it Can’t ReplaceMark Manson, author of *The Subtle Art of Not Giving a F*ck* (20 million copies, 70+ languages), argues AI will render most human self-help obsolete because it's all language, and he's building an AI app called Purpose. He claims nonfiction book sales are down 20–30% due to AI, not podcasts, and that AI will write as well as him but cannot replace his unique blend of traits. Manson shares how he uses AI for research and business coaching, and outlines an AI-proof nonfiction book requires novel concepts, creative teaching, and trust-based verticals like dating and business. He reflects on how his book's message has shifted over a decade, noting people now over-invest in identities. His advice: find the 0.1% edge case where your specific experiences overlap, because that's what AI cannot replicate.Jul 16, 2026 · 44:11 · 6.6K views
The Eventbrite Story | Julia & Kevin HartzJulia and Kevin Hartz, the husband-wife co-founders of Eventbrite, recount building the world's second-largest events marketplace from a windowless phone closet with dog beds for naps, bootstrapping until product market fit emerged from tech meetups and spread organically across categories. They describe Kevin handing the CEO reins to Julia in 2016 after 10 years, the challenging integration of Tickerfly after its acquisition, and the COVID moment when revenue went negative within 14 days, prompting rapid refunds and credits that saved the company. The Hartzes also explain the sale to Bending Spoons for long-term stewardship, Kevin's $450M third fund at A* Star capital, and their joint venture Sauron, a home security business with Atomic.Jul 5, 2026 · 49:55 · 15.4K views
This Company Is Reinventing Venture Capital | Ben Miller CEO at FundriseBen Miller, CEO of Fundrise, recounts how the 2008 crisis inspired him to democratize private markets, first through real estate and later venture capital (launched 2022), where they waited 12 months to deploy, investing in Vanta. He contrasts venture—regretting missed opportunities—with real estate—regretting bad deals—and argues that venture value-add is mostly overstated; team builds success. On AI, he says Anthropic is eating the application layer, making it hard for all but top labs, and predicts Mythos will unlock consumer apps; he notes upcoming IPOs of AI labs and SpaceX will reallocate $10 trillion, starving other sectors. He is bullish on longevity through his investment in Loyal, a dog longevity drug company, and sees human longevity within a decade. His admired AI leader is Dario Amodei for genuine concern about risks, and his personal trait is willingness to suffer.Jun 28, 2026 · 50:44 · 5K views
Why We Sold To Grammarly | Rahul VohraRahul Vohra, founder of Superhuman and now CEO of Superhuman Group after the company's acquisition by Grammarly, argues that email remains the most enduring layer of work identity and that AI will radically transform the inbox experience while distribution and taste-driven focus are the lasting moats in an era of near-zero software costs. He explains that email addresses are owned by companies and serve as the root identity and authentication unit, with professionals spending 3 billion hours daily on email. Voice features like Right With Voice on mobile now drive 30% of usage gains, and the 'Sent via Superhuman' signature still generates 20% of site traffic. The acquisition story reveals that Grammarly independently chose the Superhuman name via a branding agency, leading to the rare rebrand of the acquirer. Superhuman Group operates as a multi-product bundle ($15/$30 per month) spanning email, documents (Coder), writing agents (Grammarly), and proactive AI (Superhuman Go), with priorities on M&A to fill missing categories like chat. Vohra also angel-invests via Todd and Rahul Capital, backing companies like Loyal (which received FDA efficacy approval for a dog lifespan drug) and…Jun 21, 2026 · 1:01:18 · 6.7K views
Replit's President & Head of AI | Michele CatastaReplit's President Michele Catasta explains how the company evolved from a 15-year-old open source side project to powering 85% of Fortune 500 by launching the first vibe coding agent in 2024, before the term existed. He describes the initial rough launch that attracted candid feedback, the scramble to build an enterprise sales team when IT departments knocked, and the belief that the coding problem is nearly solved—shifting focus to integrations. Catasta argues that technical moats are less important than execution moats built from a decade of battle scars and user trust. He predicts 2026 will be the year of 'agent managers,' where every role involves managing multiple AI agents rather than single-threaded work. The Visa partnership exemplifies Replit's strategy of providing reliable building blocks for monetization, allowing vibe coders to add payments with a single prompt.Jun 16, 2026 · 49:58 · 11.8K views
Inside Mercury's Founding Story | Co-Founder & CEO Immad AkhundImmad Akhund, co-founder and CEO of Mercury, explains how the startup bank captured one in three U.S. startups by launching with product-market fit from day one—a million-dollar deposit arrived within four days from a stranger—and why legacy banks never stood a chance due to their focus on loans, expensive branch structures, and IT rather than engineering teams. Mercury raised $200M at a $5.2B valuation without needing the money, driven by 2.5x growth in Q1 2024 from AI-fueled entrepreneurship. Akhund details building trust as a moat, using small teams and Amazon's working-backwards process to launch AI features like Mercury Insights and Mercury Command, which let users run banking tasks inside AI tools. He dropped all one-on-ones after learning from Jensen Huang's 60 direct reports, favors optimistic curiosity, and angel-invests 250K checks in contrarian areas like space and deep tech.Jun 9, 2026 · 50:11 · 1.5K views
Inside Gusto's Founding Story | Co-Founder & CTO Eddie KimEddie Kim, co-founder and CTO of Gusto, reveals how the company grew from a 2012 YC startup called ZenPayroll to $1B in annual revenue and 500,000 customers by cracking the small business market against investor skepticism. He credits the 15-year co-founder relationship with Josh Reeves and Tomer London to shared values and radical directness, arguing that packaging feedback undermines trust. Kim describes building Gusto Co-Founder, an AI agent that automates back-office tasks via chat, with a team of five in eight weeks using Claude Code, embodying how the distinction between engineer and designer disappears. He calls the blank canvas problem AI's main barrier to mainstream adoption and predicts solopreneurs will thrive as AI enables anyone to become a builder.Jun 6, 2026 · 54:31 · 3K views
We Had to Reimagine Nextdoor | CEO & Co-Founder Nirav ToliaNirav Tolia, CEO and co-founder of Nextdoor, explains the company's multi-year turnaround from treading water to 14% revenue growth and 22 million weekly active users, and argues that the future lies in an AI-enabled 'age of human connection' where technology amplifies real-world community rather than replacing it. He recounts the crucible moment when a board meeting in May 2018 led to his return as CEO after a five-year absence, and how investor Bill Gurley's recitation of Rudyard Kipling's 'If' spurred him to persevere. Tolia emphasizes that Nextdoor's requirement of real names and verified addresses, built from the start, gives it a trust advantage in an AI-dominated era. He describes the importance of co-founders like Sarah Leary, with whom he has worked for 27 years, and shares specific data: one in three U.S. households are on Nextdoor, with an aspiration to reach three of three. The episode also covers his brief stint as a Shark Tank shark, the opening of a new Dallas office, and a hybrid work philosophy that prioritizes both in-person energy and remote flexibility.Jun 3, 2026 · 57:02 · 4.2K views
5 Grand Slam Champion Maria Sharapova: Tennis Icon | Entrepreneur | Investor | New Media CreatorMaria Sharapova, five-time Grand Slam champion, reflects on her tennis career, emphasizing that most preparation happens when nobody's watching and that commitment to quality defined her proudest moments. She discusses the challenge of balancing fierce competition with personal boundaries, the business of sport and building a team, and how a shoulder injury in her early 20s first made her plan for a second act. Sharapova describes reinventing herself after retirement by taking a break and applying athletic lessons to entrepreneurship and her podcast 'Pretty Tough,' which explores the duality of grit and vulnerability. She shares her take on AI, noting its positive uses in sports like IBM's Wimbledon predictions and automated video analysis, but values human connection in media. In rapid-fire questions, she names Monica Seles and Steffi Graf as admired icons, Serena Williams as both the toughest opponent and a close friend who introduced her into the Tennis Hall of Fame, and says what makes her tough is the ability to say no.May 20, 2026 · 52:29 · 48.3K views
How Many $10 Billion Startups Will There Be? | Eric HippeauEric Hippeau, co-founder of Lerer Hippeau, argues that while AI is transforming tech faster than ever, startups must avoid being mere wrappers around foundational models, as they can be instantly disrupted. He explains that physical AI, combining hardware and AI in areas like robotics and defense, offers more defensible opportunities. Hippeau warns that the startup market is disconnected, with inflated seed valuations assuming many will reach $10B, but historically there's no market for hundreds of such companies. He discusses healthcare, where AI-driven diagnostics could make primary care nearly free, but political will is needed to overcome entrenched systems. On media, he shares lessons from building Huffington Post—keeping stories live and separating opinion—and predicts that AI could restore trust by providing verifiable facts. Hippeau also reveals he has rebuilt his firm's workflow around Anthropic's Claude, cites AR glasses as underrated, and notes that solo GPs must build teams to succeed.May 13, 2026 · 57:21 · 1.9K views
Will AI Models Ever Compensate Creators? Tony Stubblebine (Medium CEO)Tony Stubblebine, CEO of Medium, argues the creator economy is ending as AI slop floods public channels, but a writing renaissance is emerging where authentic expertise and private communities hold value. He details Medium's turnaround from losing $2.5M per month and $37M in debt to profitability, achieved by restructuring investor relationships and refocusing on human-written content. Stubblebine warns that AI companies like OpenAI created a 'prisoner's dilemma' by scraping content without compensation, pushing high-quality writing into walled gardens. He introduces Medium's new AI-assisted writing app TK and private blogging groups as responses to the era. The episode explores how creators must diversify revenue streams and reinvent themselves, while per-inference pricing standards like RSL slowly develop.May 6, 2026 · 53:35 · 13.7K views
We Ignored Silicon Valley Advice for 3 Years | Nicolas Sharp (Attio)Nicolas Sharp, co-founder of Attio, explains why the CRM startup spent 1,000 days building in stealth—a deliberate counter to the 'ship fast' philosophy he learned from a previous venture—and how that architectural investment now powers Attio's AI-native platform. He argues that the half-life of product-market fit has collapsed, forcing companies to simultaneously iterate and scale, and that Attio's high-resolution data pipelines are critical for deploying AI agents. Sharp also details how Attio used manual waitlist onboarding to validate demand, how fundraising expectations have risen dramatically (Attio raised $52M at Series B with accelerating growth), and why Europe is having a breakout moment as an AI hub, citing talent from DeepMind and Palantir as catalysts.Apr 30, 2026 · 57:49 · 10.7K views
Why Andreessen Horowitz Is Still Betting Big On CryptoAli Yahya, general partner at Andreessen Horowitz (a16z), explains why AI and crypto are converging faster than predicted, with privacy emerging as a key defensive moat for crypto startups. He defines AGI as the point when an agent can be fully economically independent and outlines five stages of autonomous commerce, from automated payments to agent-to-agent transactions. Yahya is skeptical about AI agents trading for consumers—since everyone using ChatGPT eliminates alpha—but sees potential for professionals with proprietary data. He notes that a16z's 70-person platform team provides legal, research, and go-to-market support, and that the cost of entry has collapsed, letting founders test ideas with smaller teams before raising capital. He also highlights prediction markets, now legal in the US, as a growing category and recommends robotics as the next frontier, calling physical intelligence a 10–15 year arc offering time for newcomers to enter.Apr 22, 2026 · 50:25 · 3.5K views
Students Will No Longer Be Taught By Teachers | Joleen LiangJoleen Liang, co-founder of Squirrel AI, explains how its LAM engine—powered by over 20 billion learning behavior data points—replaces traditional teachers by handling 100% of knowledge transfer, turning instructors into data analysts and psychologists. She details how the Chinese Double Reduction policy in 2021 slashed revenue from $300 million to zero overnight, forcing a pivot to a hardware-integrated smart tablet and leading 80% of franchisees to convert $160 million in debt into company stock. The company now expands into the US with self-study centers and plans to introduce physical AI robot teachers within five years, while arguing that generic LLMs cannot deliver truly personalized education. Liang also shares how the co-founders maintained belief through the crisis, prioritizing health and exercise, and advises founders not to underestimate their abilities.Apr 15, 2026 · 46:16 · 41.2K views
Yahoo Is Striking Back | CEO Shares The LatestYahoo CEO Jim Lanzone and SVP Eric Feng explain how Yahoo is striking back with AI-powered products like Scout and MyScout, leveraging its 700 million users and proprietary data to differentiate from generic chatbots. After being taken private by Apollo in 2021, Yahoo sold off non-core assets and restructured into GM-led units, cutting headcount by 50% while remaining profitable. The company owns its AI tech, using 30 years of search history and unique knowledge graphs to deliver accurate, citation-rich answers that send traffic to publishers, unlike other AI engines. They argue this approach is possible because Yahoo dominates categories like finance (#1) and sports (#2), each with 100M+ monthly users, and that AI is causing a seismic shift in search behavior (Google's lowest market share in a decade). The duo emphasizes that domain expertise now matters more than pure technical skills, and they are planning agentic features that move from information to action, such as booking trips or setting fantasy lineups, to increase user touchpoints from once a day to multiple times an hour.Apr 7, 2026 · 53:50 · 60.1K views
Why Hand-Typing Code Will End Your Career in 2026Dan Shipper, co-founder and CEO of Every, argues that AI agents like OpenClaw and vibe coding—prompting apps in English—are fundamentally reshaping how companies operate, from internal workflows to product development. Every, a 20-person company running four AI-native products (Quora, Spiral, Sparkle, Monologue), treats failed software experiments as content that builds distribution, and uses a 'two-slice team' approach where each product is managed by one person. Shipper details how he reclaimed the 'founder' title for legitimacy, the four-year 'flatline' period before the AI wave hit, and why over-hiring early is 'crazy—most of the time it doesn't end well.' He advises founders to automate every internal process with AI and build for both humans and agents.Mar 2, 2026 · 49:31 · 9.5K views
The Brutal $1.2B Unicorn RealityKirill Bigai, founder of Preply, argues that the company's $1.2 billion unicorn valuation is a discipline story, not a success story, built on lean operations and unit economics. He recounts launching with a concierge MVP—a single landing page and manual tutor matching on Skype—while living with five co-founders in one house without salaries. To scale, Preply focused on SEO and SEM to acquire both learners and tutors, achieving ROI-positive results. During the war in Ukraine, the company took responsibility for evacuating 150 employees from Kyiv, fostering unity and resilience. Bigai envisions a 'human-first, AI-enabled' future where AI acts as a co-pilot for tutors, automating homework and improving learner-tutor matching.Feb 22, 2026 · 47:43 · 9.6K views
THIS COST US $1.7 BILLIONColin Angle, iRobot founder, recounts the 33-year journey from MIT's 'artificial insect' lab to the $1.7 billion Amazon acquisition that the FTC blocked, calling it a political move that damaged the innovation economy. He explains how Roomba combined mine-hunting algorithms, industrial cleaning tech, and toy manufacturing, and how a Dave Chappelle Pepsi commercial saved the company from 250,000 unsold units. The FTC's anti-M&A attitude froze iRobot for 18 months, preventing it from adapting to market changes, which ultimately led to bankruptcy. Now he's launching Familiar Machines and Magic to apply AI-powered robotics to elder care and wellness, aiming to build the robots we were promised beyond floor cleaning.Feb 8, 2026 · 1:02:31 · 223 views
A16Z Partner: Why "Just Capital" Is Not Enough Anymore (The Firm of 2030) | David HaberDavid Haber, a16z general partner, argues most venture investors run funds but few build firms, and explains how a16z operates as a firm with compounding competitive advantage. The firm reinvests fees into a 600-person platform giving founders distribution, credibility, and leverage. Haber shares his founder story: Bond Street raised $900M in debt, sold to Goldman Sachs, teaching him inside a 40,000-person organization. On AI, he says software becomes labor, expanding TAM beyond IT spend—portfolio company Salient's voice agents achieve 50% better collection rates. He also highlights a16z's decentralized model with no single CIO, where specialist partners run divisions, making the firm more resilient than traditional funds.Jan 25, 2026 · 56:58 · 725 views
He Built A $1.8B AI Company With No Experience | Max JunestrandMax Junestrand, CEO of legal AI company Legora, explains how AI is rewiring the legal profession, arguing that not building in AI is the biggest career risk. Legora, which went through YC W25 and has raised $260M, doubles ARR every quarter by embedding with law firms to solve real problems. Junestrand details how AI adds a fourth step to the lawyer career ladder—junior associate, senior associate, partner, AI—pushing junior lawyers to focus on intelligence and client skills earlier. He describes Legora's shift from chat to large-scale document review and Word-native drafting, and predicts a move from billable hours to outcome-based pricing as AI automates more work. Junestrand also shares his fundraising approach: build a great business and investors come to you, with Legora's Series B closing in a week and Series C in a week and a half.Dec 14, 2025 · 52:02 · 3.5K views
The Unicorn Nobody Saw Coming | Ahmet Bahadir OzdemirAhmet Bahadir Ozdemir, the accidental founder of Airalo, built the world's largest eSIM marketplace by pivoting from a ship-supply business after Apple's eSIM announcement in 2018. He started SIM4CREW for 1.7M seafarers, then killed it to launch Airalo, relying on luck and timing. First customers came from unscalable hacks—wearing Airalo shirts, fake elevator calls, and Twitter bots—until a $5,000 influencer investment cracked growth. COVID hit after raising a $5.4M Series A, but overspending forced an early raise that left enough cash to survive zero revenue, panic attacks, and a war on waste. Airalo's culture centers on empathy and individual stories, rejecting 'greater good' logic—every gigabyte used globally is the long-term goal, via a connectivity layer powering devices directly or through partners.Dec 7, 2025 · 56:43 · 758 views
The Hidden Skill Behind Every Successful Founder | Lindsay KaplanLindsay Kaplan, co-founder of Chief, explains how she and her co-founder Caroline built the women's executive network from cold emails that landed the first 200 members to a unicorn with tens of thousands on the waitlist. She details pivoting from in-person to digital in days during COVID, launching physical spaces, and the art of co-founder dynamics—emphasizing disagreement and complementary skills. Kaplan describes stepping down as operator after seven years, moving to VC at Next Wave NYC, and why she backs founders at the intersection of AI and real-world community, arguing that AI is a tool that cannot replicate in-person connection.Nov 30, 2025 · 37:06 · 303 views
The Harsh Truth About Building a Startup in the AI Era | Anish AcharyaAnish Acharya, General Partner at a16z, argues the AI era has reopened consumer tech's biggest window since mobile, with consumers paying $200–$250 monthly for products like Gemini Ultra and ChatGPT. He warns founders against traps like thinking they're too late, noting AI code and legal will become entire industries with dozens of winners. Voice AI is an enterprise insertion point where agents already outperform humans at negotiation, while the next social platform will revolve around software creation rather than content. He dismisses the AI wrapper risk because multi-model products and fine-tuned data give startups defensibility, and advises founders to raise 24-month rounds focused on product, not marketing. Acharya also predicts 2026 will bring new distribution channels via OpenAI's Apps SDK, Apple's mini apps, and group chat discovery.Nov 23, 2025 · 51:12 · 3K views
The AI Version of You Will Outperform You — Emad MostaqueEmad Mostaque, founder of Stability AI and now Intelligent Internet, argues that within 1,000 days, AI will create digital twins that replace most cognitive jobs, but the bigger risk is cognitive colonialism—a handful of corporations controlling the AI layer closest to people. He explains why he left Stability after it reached 300 million downloads to build open, sovereign AI for healthcare, education, and government, citing a medical model that outperforms human doctors on benchmarks and runs on a laptop. Mostaque warns that graduate jobs are already disappearing, and by 2028 coding jobs as we know them will vanish, replaced by English-language AI. He advocates for universal basic AI alongside universal basic income, and announces Sage, an open-source policy engine for governments, and a ChatGPT alternative that routes through any model at cost. The episode details his vision for distributed civic AI funded via Foundation Coin, where compute goes toward helping people rather than maximizing profit.Nov 16, 2025 · 51:27 · 30.1K views
OUT NOW: Solana's Founding Story | Anatoly YakovenkoAnatoly Yakovenko, co-founder and CEO of Solana, tells the story of how his eureka moment—a calculation showing Solana could achieve 1,000 to 10,000 times more throughput than Ethereum or Bitcoin—led to a manic four days and eventually to a blockchain that processes in a single month as many transactions as Ethereum does in its lifetime. He details the brutal fundraising process, requiring 1,000 meetings to secure the first major check, and the near-catastrophic moment during Solana's biggest conference (1,600 developers, sold out) when FTX collapsed on the flight back, threatening the entire ecosystem. The episode explores Anatoly's vision for decentralized finance beyond speculation and the challenges of building a truly open on-chain financial system.Nov 10, 2025 · 1:06 · 1.6K viewsSukhinder Singh Cassidy, CEO of Xero, explains how the cloud accounting platform reached $2.7 billion in revenue, 31% growth, and 5 million customers by cracking the US through the Milio acquisition, building product from the US, and narrowing focus to a "US unicorn" number. She details why the US took 20 years—Intuit's entrenched home-market advantage and the need for local engineers—and why she treats "respected vs. liked" as a false choice, backing layoffs with data and speed. On AI, she argues thin application wrappers can't replicate Xero's tens of thousands of edge cases, regulatory connections, payment rails, and trusted data across 180 countries, making infrastructure the real moat. She also answers whether accountants stay relevant by pointing to Client Advisory Services, and describes the customer spectrum from AI-native builders to those needing basic AI chat support.
Sukhinder Singh Cassidy, CEO of Xero, joins NEW ECONOMIES to explain why cracking the US took twenty years and an acquisition despite Xero being the more open, cheaper alternative to Intuit, why she treats “respected vs. liked” as a false choice a new CEO has to reject on day one, and why the biggest threat to a twenty-year-old platform isn’t a faster competitor but the capital and infrastructure it takes to replicate what that platform already owns. Timestamps: (0:00) Meet Sukhinder Singh Cassidy (2:17) The Current State of Xero (5:35) Why America Was So Hard to Crack (10:05) Why It's Important to Focus (12:55) Joining Xero as CEO (16:40) Being Respected vs. Liked (22:57) How to Prepare for a Layoff (27:30) Being a Publicly Listed Company CEO (30:07) The State of SMBs (33:30) Thinking How to Partner with AI Models (36:24) How Much Code Is Written by AI? (38:39) How Does Xero Stay Relevant? (42:51) Is Trust the Next Biggest Moat? (43:39) The Biggest Opportunity for Xero (46:00) Will Accountants Still Be Relevant? (48:08) Companies Who Aren't Hiring AI Talent (49:05) Ollie Joins as Sukhinder’s Chief of Staff (50:39) Personal Time Out Links: Follow Ollie on LinkedIn: https://www.linkedin.com/in/ollieforsyth/ Follow Sukhinder on LinkedIn: https://www.linkedin.com/in/sukhinders/ Visit Xero: https://www.xero.com/ Episode Partners - Harmonic, the go-to startup database: https://harmonic.ai/ Episode Partners: Hostinger, a go-to tool for builders: https://hostinger.com/neweconomies. Enter code NEWECONOMIES for 10% off.
