The AI Report Live

• The Quietest $3B Tech Company You’ve Never Heard Of

  This week on The AI Report, Liam Lawson sits down with Gordon Wintrob, co-founder and CTO of Newfront, to talk about bringing AI into one of the slowest-moving industries: insurance.Gordon shares how Newfront is redesigning the broker experience with automation and AI—from parsing 200-page policies in seconds to helping HR teams save weeks of work. They discuss building AI tools that clients actually trust, how to manage risk in regulated industries, and why embedding AI into company culture matters as much as the code.Also in this episode: • Why insurance is one of the last big frontiers for tech • What makes a good AI use case in complex workflows • The story behind Benji, Newfront’s internal AI assistant • How to foster internal adoption from hiring to hackathons • What regulation and SOC 2 mean for AI innovationThis is a real look at what happens when AI goes beyond chatbots and into core business infrastructure.Subscribe to The AI Report:https://theaireport.beehiiv.com/subscribeJoin the community:https://www.skool.com/the-ai-report-community/aboutChapters:(00:00) Reimagining the Insurance Stack(01:06) Why Insurance Feels So Behind(02:41) How Brokers Work and Where AI Fits(05:08) Founding Newfront With Future Tech in Mind(06:59) Automating Contract Review at Scale(08:49) Working With Startups and Industry Giants(10:19) What It’s Like Serving Diverse Client Profiles(12:17) Making Room for Value-Add Conversations(13:28) Key AI Tools: Benji, Gap Analysis, and More(15:29) Why Products Succeed or Fail in Legacy Fields(16:39) Creating a Culture of Technical Curiosity(18:25) From Engineering to Recruiting: AI in the Org(19:30) Equity, Values, and Ownership at Scale(21:50) What Keeps Traditional Brokerages Behind(23:43) AI as a Signal of Operator Leverage(25:22) Who Newfront Builds For(25:56) Staying Compliant While Moving Fast(28:39) Managing Data Risk in a Privacy-Critical Industry(29:01) Vendor Security and SOC 2 in AI Development(30:25) Expanding AI Beyond the Frontend(31:58) CTO Strategy and Time Allocation(32:54) Staying Up-to-Date in a Fast-Shifting Landscape(34:42) Building With Purpose in a Legacy System(36:11) Connect With Gordon

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• The Most Overlooked Business Model on the Internet

  On this episode of The AI Report, Liam Lawson is joined by Frey Chu—a directory builder, SEO educator, and creator focused on building long-term, high-leverage digital assets.Frey shares how he builds directories that actually work, why so many fail to get traction, and how to combine AI workflows, structured data, and strong SEO fundamentals to make evergreen content that ranks and converts.They discuss the real art of choosing a niche, when to enrich data manually vs programmatically, and why directories—when done right—are still one of the best internet business models available.Also in this episode: • What separates real directories from content farms • How to validate a niche with Reddit and Ahrefs • Why LLMs are forcing a rethink of “content quality” • The pros and cons of exact-match domains • Frey’s thoughts on time freedom, creative control, and building slow on purposeIf you’ve ever wanted to build a niche site, test an idea, or launch a project that runs without you, Frey’s approach will give you a grounded, tactical blueprint.Subscribe to The AI Report:https://theaireport.beehiiv.com/subscribeJoin the community:https://www.skool.com/the-ai-report-community/aboutChapters:(00:00) What Makes a Directory Valuable(01:06) Ranking Local Queries With SEO(02:34) The Difference Between Lists and Real Directories(04:32) Why “Directory of Directories” Doesn’t Work(05:36) Finding Balance Between SEO and Passion(07:55) Evergreen Niches That Print Cashflow(10:05) Reviewing His Portfolio: Hits and Experiments(11:15) Why Directories Are Still Relevant(12:19) LLMs and the Future of Structured Data(13:38) Monetize First or Learn First?(15:11) Validating Demand Without Guesswork(16:35) Data Enrichment Strategies That Work(17:54) Choosing the Right Stack for Directory Projects(18:57) Quality Markers That Matter in 2025(20:00) High-Consequence Niches With Real Need(21:43) Feedback Loops and Iterating in Public(23:03) Do Domains Still Influence Trust and Ranking?(24:12) Frey’s Monetization Framework(25:19) Getting Ready for the Next Phase of LLM SEO(27:50) How Frey Keeps Learning and Evolving(29:04) The People and Projects He’s Studying(30:10) The Multi-Skill Nature of Directory Projects(31:54) Long-Term Goals: SaaS, Marketplaces, and Time Freedom(33:44) Why He’s Teaching Now(35:52) Where to Find and Follow Frey

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  36:29
• Product-Market Fit Still Matters—Even in 2025

  This week on The AI Report, Liam Lawson is joined by Peter, a startup coach and product strategist who’s helped dozens of early-stage founders avoid one of the most costly mistakes in tech: building before validating.Peter explains why most startup ideas fail not because the tech doesn’t work, but because there’s no real demand. He shares the “sandwich method” he uses to get honest, useful feedback in discovery calls, and how founders can avoid building in a vacuum.They also explore the role AI is starting to play in validation workflows—and why it can’t replace true customer insight.Also in this episode: • Why product-market fit is not a feeling • How to structure conversations to get real signal • The biggest lies founders tell themselves during early validation • How to use AI tools in discovery without getting misled • Why humility might be the most valuable founder skillIf you’re building anything new—especially in AI or SaaS—this episode is a sharp, tactical reset.Subscribe to The AI Report:https://theaireport.beehiiv.com/subscribeJoin the community:https://www.skool.com/the-ai-report-community/aboutChapters:(00:00) Misunderstanding Product Validation(01:15) Who Peter Works With and Why(03:40) The Sandwich Method for Better Discovery(06:05) What He Learned From YC and Startup #1(08:12) Founders as Pattern Matchers(10:33) Detecting and Avoiding Bias(13:00) Identifying Real Market Demand(15:18) The Feature Fallacy(17:50) AI Tools vs Product Necessity(19:36) Where AI Can (and Can’t) Help(21:44) Advice for Founders on Day Zero(23:50) Why Peter Keeps Coaching(26:04) Where to Find Him

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  45:18
• The CEO Who Called Us Out—And Might Be Right About AI Content

  This week on The AI Report, Liam Lawson talks with Nick Jain, former IdeaScale CEO and founder of Content Hurricane, about how he used AI to completely replace traditional marketing and scale his funnel 50x.Nick shares how a $25 AI agent outperformed his in-house team, created content that outranked McKinsey on Google, and helped him build one of the most efficient B2B funnels in SaaS. He breaks down how he did it, why most marketers are missing the shift, and what the future looks like when AI runs most of your company’s creative output.Also in this episode: • Building a 90% AI-powered inbound funnel • Why content teams will be replaced, not reskilled • The new role of product managers in an AI-led org • How Content Hurricane scales enterprise-quality assets with no human input • The future of education, work, and intellectual leverageThis is not a “how to write prompts” episode. It’s a front-row view into what happens when a founder goes all in on AI and doesn’t look back.Subscribe to The AI Report:https://theaireport.beehiiv.com/subscribeJoin the community:https://www.skool.com/the-ai-report-community/aboutChapters:(00:00) Why Content Marketing Is On Its Way Out(01:14) A $25 Agent vs a Whole Marketing Team(02:26) Nick’s Moment of Clarity in Amsterdam(03:28) Scaling Content With ChatGPT in 30 Minutes(05:21) Running Mandatory AI Training at IdeaScale(06:45) Who Actually Adopted the Tech(08:17) From Harvard MBA to Startup CEO(09:00) Inside a 90% Automated Marketing Funnel(10:00) What Good Content Actually Means for SEO(12:31) Why Algorithms Are Not the Point(14:13) Tracking True ROI Across All Content(16:13) The Channels That Still Work(17:08) Nick’s Favorite Prompt Strategy(18:34) The End of the Content Marketing Role(20:21) CEO Ethics in the AI Age(22:04) Why Sales and Product Still Matter(24:03) The Future of Product Management(25:31) Why Generalists Have the Edge Now(27:05) What Happens to Traditional Education(28:10) The Chips Are Coming: Post-Human Thinking(30:13) How Content Hurricane Operates(32:01) Awareness to Action With AI(33:36) The Simplicity Advantage in UX(35:09) Prompting for Depth, Not Generic Output(36:03) Product With Purpose(36:22) Massive Growth Metrics From the Funnel(38:12) Why Nick Keeps Building(39:05) How to Connect With Him

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  39:17
• How to Monetize Your 9–5 Experience Without Quitting Your Job

  This week on The AI Report, Liam Lawson is joined by Lindsay Rosenthal, founder of Synnc and one of the leading voices in the B2B creator economy. Lindsay shares how she went from building a presence on LinkedIn to launching a software platform that connects brands and professionals for high-leverage collaborations.She breaks down what’s changing in B2B marketing, why creators are becoming critical distribution channels, and how she built and shipped a product without a technical background, leveraging AI tools to move faster and execute smarter.Also in this episode: • The rise of B2B creators and micro-influencers • How Synnc uses AI to match brands and creators • Why a personal brand is now part of your resume • The challenge of balancing content, consulting, and product building • What it really takes to launch a product with limited resourcesIf you’re trying to grow on LinkedIn, launch a tool, or find smarter ways to work with AI, this conversation is full of sharp insights from someone doing all three at once.Subscribe to The AI Report:https://theaireport.beehiiv.com/subscribeJoin the community:https://www.skool.com/the-ai-report-community/aboutChapters:(00:00) Why Community is Career Insurance(01:04) AI Meets LinkedIn: What’s Happening Now(02:10) B2B Creators Are the New Growth Engine(03:20) Personal Brand as a Strategic Asset(04:36) Imperfect Content Beats AI-Polished Posts(06:13) The Real Voice of B2B: Messy and Human(07:47) What Synnc Actually Does(09:00) How Brands and Creators Use the Platform(11:09) AI Workflow Automation Behind the Scenes(13:14) Why Creator Rates Are Climbing in B2B(14:21) Big Value From Small Audiences(16:20) Winning With Focused Distribution, Not Virality(17:05) Collabs, Testimonials, and Fractional Roles(18:17) Building and Shipping Without a Tech Background(19:31) The Realities of Building in Public(21:05) Why Speed and Timing Matter Most(22:12) Lindsay’s Origin Story and Customer Zero(24:03) From Student Podcast to Software Startup(25:57) Spotting Trends and Building Early(28:02) Why Non-Technical Founders Are Winning Now(29:08) Using AI for Product Design and Dev Work(31:07) AI-Powered Matching and Briefing(32:48) Reducing Friction With Smarter Systems(34:03) How Lindsay Balances Multiple Lanes(35:15) Tools, Systems, and Mental Clarity(36:07) The Value of Doing More to Think Better(37:07) Synnc’s Next Moves(39:04) What She’s Working on Behind the Curtain(41:12) How to Connect With Lindsay and Try Synnc

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  41:21

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