We Live to Build

Is AI about to replace your stock broker? Christine Healey, a pre-IPO investment expert, explains why Claude AI missed a critical detail in a deal that could have cost her client millions—and why human brokers are still essential in the private market. In this interview, Christine and Sean discuss the "wild west" of pre-IPO investing, how to avoid scams when buying shares of companies like SpaceX and Stripe, and the secret tax strategies (like the Peter Thiel Roth IRA hack) that can save you millions. They also debate whether employees selling shares before an IPO is a red flag or just smart financial planning. Check out the company: https://healeypreipo.com👀 CONNECT WITH SEANSubscribe: https://www.youtube.com/@seanweisbrotLinkedIn: https://linkedin.com/in/seanweisbrotInquiries: welivetobuild@gmail.com🕒 CHAPTERS00:00 - Why AI Can't Replace Investment Brokers (Yet) 01:30 - The Human Touch in Private Equity Deals 02:20 - Direct Shares vs. SPVs: Which is Better? 04:40 - Pre-IPO Scams: How to Not Get Ripped Off 08:15 - Why Employees Sell Shares Before an IPO 10:45 - How to Invest in SpaceX & OpenAI 13:20 - What Does "Pre-IPO" Actually Mean? 16:00 - Early Stage vs. Late Stage Venture Risk 18:00 - Taking Fees as Equity (The "Carry" Strategy) 19:25 - The Taboo of Secondary Sales 21:00 - The "WeWork" Lesson: Why Cash Flow Matters 24:00 - The Peter Thiel Tax Hack (Roth IRA Investing) 26:50 - The #1 Lesson: Details Make the Deal📈 WORK WITH ME▶ Startup Fundraising: https://welivetobuild.com/fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/collaborate▶ My AI/Automation Agency: https://optimai.ai🎧 LISTEN TO THE AUDIO VERSIONSpotify: https://open.spotify.com/show/68lykxIMOyofZNiWSF4vFxiTunes: https://podcasts.apple.com/us/podcast/we-live-to-build/id1531994765

Is AI about to replace lawyers, or is it a "disaster" waiting to happen? Omeed Tabiei, a startup lawyer, breaks down the viral story of Fred Wilson replacing a $50k legal bill with AI and why it has the legal industry panicking. However, he also shares cautionary tales of founders who used AI templates (like Rocket Lawyer) and ended up with messy, expensive legal battles. In this interview, Omeed and Sean discuss the critical legal mistakes that destroy startups: from choosing an LLC instead of a Delaware C-Corp, to 50/50 co-founder equity splits without vesting. He also reveals a unique strategy one client used to raise $600k in 30 days directly from their customers on social media. Check out the company: https://optimistlegal.com👀 CONNECT WITH SEANSubscribe: https://www.youtube.com/@seanweisbrotLinkedIn: https://linkedin.com/in/seanweisbrotInquiries: welivetobuild@gmail.com🕒 CHAPTERS00:00 - Fred Wilson vs. The $50k Legal Bill (AI Replacement?) 02:18 - Why AI Legal Advice is Often Wrong (And Dangerous) 05:07 - When Do You Actually Need a Lawyer? (Pre-Seed vs. Series A) 09:30 - The Founder Who Ruined His Exit with a Rocket Lawyer Template 11:35 - The Y Combinator Founders Who Stole Code & Got "Flamed" 13:20 - The #1 Co-Founder Mistake: 50/50 Splits & No Vesting 16:25 - Why VCs Will NEVER Invest in an LLC (Delaware C-Corp Only) 20:50 - How One Founder Raised $600k in 30 Days on Social Media 25:40 - Debt vs. Equity: When to Stop Selling Your Company 27:10 - The #1 Career Lesson: Be a Voracious Learner📈 WORK WITH ME▶ Startup Fundraising: https://welivetobuild.com/fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/collaborate▶ My AI/Automation Agency: https://optimai.ai

Is the new open-source AI agent "OpenClaw" a revolutionary tool for startups, or a dangerous liability that could destroy your computer and spend thousands of your dollars? Sze Wong returns to the podcast to debate Sean on the massive risks and rewards of giving autonomous AI agents full control over your machine. In this heated discussion, Sze explains why the future of startups isn't building SaaS products, but rather selling "AI Agent Teams" as a service—like a digital staffing firm. Meanwhile, Sean shares terrifying stories of AI models trying to blackmail engineers and why he refuses to give agents access to his personal data. They also cover why Sze prefers Anthropic's Claude over OpenAI , the psychology of naming your AI "Felix" , and how Sze used AI to build a Calendly clone over a single weekend. Check out the company: https://zenithstudio.io👀 CONNECT WITH SEANSubscribe: https://www.youtube.com/@seanweisbrotLinkedIn: https://linkedin.com/in/seanweisbrotInquiries: welivetobuild@gmail.com🕒 CHAPTERS00:00 - The Controversial Thesis: Why OpenClaw Will Win00:25 - The Dangers of Autonomous AI Agents03:25 - How to Safely Test AI Agents (Use a VPS)04:40 - The AI That Tried to Blackmail an Engineer08:40 - Claude Code vs. OpenAI: Which is Better?15:00 - The Psychology of Naming Your AI (Meet "Felix")20:15 - Why SaaS is Dead (The "AI Staffing Firm" Future)24:00 - Building a Calendly Clone in One Weekend with AI28:30 - The Reality of "Vibe Coding" to Production📈 WORK WITH ME▶ Startup Fundraising: https://welivetobuild.com/fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship▶ My AI/Automation Agency: https://optimai.ai🎧 LISTEN TO THE AUDIO VERSIONSpotify: https://open.spotify.com/show/68lykxIMOyofZNiWSF4vFxiTunes: https://podcasts.apple.com/us/podcast/we-live-to-build/id1531994765

Are you unknowingly breaking the law by paying a commission to someone helping you raise capital? Wendy Culbertson, a securities lawyer, warns that many startup founders are violating SEC rules by paying "finders" who are not registered broker-dealers. In this interview, she explains the severe consequences of these illegal payouts, including civil and criminal liability. Wendy breaks down the complex world of SEC regulations, explaining the critical differences between Regulation D (506b vs 506c), Regulation A (Mini-IPO), and Crowdfunding (Reg CF). She also reveals the "safe harbor" strategies for hiring internal investor relations staff without triggering regulatory action and why founders should think twice before handling filings themselves. Check out the company: https://👀 CONNECT WITH SEANSubscribe: https://www.youtube.com/@seanweisbrotLinkedIn: https://linkedin.com/in/seanweisbrotInquiries: welivetobuild@gmail.com🕒 CHAPTERS00:00 - Why Many Founders Are Breaking Securities Law 01:50 - The Danger of Paying "Finder's Fees" 04:12 - What is a Broker-Dealer? (SEC Definition) 07:05 - Safe Harbor: Hiring Employees to Raise Capital 09:20 - Can You Pay Fundraisers with Equity? 10:20 - Reg D vs. Reg A vs. Crowdfunding Explained 15:00 - Why Reg D and Reg CF Are Named That Way 18:50 - When Do You Need to File with the SEC? 20:00 - "Blue Sky Laws": State-Level Compliance Nightmares 23:30 - Should Founders File Their Own SEC Forms? 24:35 - The Risks of Unregistered Broker-Dealers (Criminal Action)📈 WORK WITH ME▶ Startup Fundraising: https://welivetobuild.com/ai-startup-fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/collaborate▶ My AI/Automation Agency: https://optimai.ai

Why do most climate startups fail to scale? Tom Chi, a founding member of Google X and inventor with 77 patents, argues that relying on "Green Premiums" or even price parity is a death sentence. In this interview, he reveals the "CapEx Inertia" trap that prevents factories from adopting new tech and why your solution needs to be 3x cheaper than the incumbent to survive. Tom shares the heartbreaking story of watching a coral reef die in just two months—a tragedy that pushed him from inventing to investing. He breaks down his unique physics-based diligence process (analyzing Matter, Energy, Time, and Space) and explains why he focuses on the four industries responsible for 90% of water pollution. Finally, he shares his life philosophy on why you should focus on "verbs" (your metabolism of learning) rather than "nouns" (status and titles).Check out the company: https://www.atoneventures.com👀 CONNECT WITH SEANSubscribe: https://www.youtube.com/@seanweisbrotLinkedIn: https://linkedin.com/in/seanweisbrotInquiries: welivetobuild@gmail.com🕒 CHAPTERS00:00 - From Google X Inventor to Climate Investor 02:55 - The Coral Reef Tragedy: Extinction by 2055? 08:38 - Why Hardware is Easier to Pick than SaaS 11:53 - The 4 Industries Causing 90% of Damage 13:28 - The "Triad" Investment Thesis 14:40 - Why "Green Premiums" & Price Parity Fail 15:40 - The "CapEx Inertia" Problem 18:00 - How to Due Diligence with Physics (Matter, Energy, Time, Space) 22:50 - Why Software Metrics Don't Work for Deep Tech 25:35 - Investment Readiness Levels (Avoiding Science Risk) 27:50 - The Cold Fusion & Superconductor Hype Cycles 30:10 - The #1 Life Lesson: Nouns vs. Verbs📈 WORK WITH ME▶ Startup Fundraising: https://welivetobuild.com/ai-startup-fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/collaborate▶ My AI/Automation Agency: https://optimai.aines: https://podcasts.apple.com/us/podcast/we-live-to-build/id1531994765

Why is aiming for 10x growth actually easier than aiming for 2x? Philipp Wehn, founder of an AI company for heavy industries, explains how raising $15 million shifted his mindset from survival to dominance. In this interview, he reveals why you need to stop doing 80% of your tasks to achieve exponential results. Philipp breaks down his unique business model—combining a high-touch service agency with a scalable AI software platform—and why he charges enterprise clients based on value created ($1M+) rather than seat licenses. He also shares his "athlete mindset" for leadership, why he forces his team to take time off to recharge, and the critical difference between "playing not to lose" and "playing to win." Check out the company: https://nexxa.ai👀 CONNECT WITH SEANSubscribe: https://www.youtube.com/@seanweisbrotLinkedIn: https://linkedin.com/in/seanweisbrotInquiries: welivetobuild@gmail.com🕒 CHAPTERS00:00 - Why 10x Growth is Easier Than 2x 01:29 - How to Audit Your Calendar for "Noise"02:40 - Charging for Value ($1M+) vs. Software Licenses 06:00 - The Hermes Strategy: Why Premium Pricing Wins 07:13 - The "Athlete Mindset": Discipline & Recovery 10:04 - Building Culture Remotely (VR Nights & Off-Seasons) 12:15 - Running Your Startup in "Seasons" (The NFL Model) 14:26 - The Netflix "Keeper Test" for Employees 16:15 - Why We Raised $15M (Speed vs. Bootstrapping) 18:30 - The "LLM Wrapper" Debate: Why Engineering Matters 21:40 - Business Model Innovation as a Moat 27:53 - The #1 Lesson: Stop Playing Not to Lose📈 WORK WITH ME▶ Startup Fundraising: https://welivetobuild.com/ai-startup-fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/collaborate▶ My AI/Automation Agency: https://optimai.ai

Why do talented new hires often destroy value instead of creating it? Matt Putra, founder of EightX and a fractional CFO for 8-figure brands, argues that "profitability is a human problem," not a math problem. In this interview, he explains how misaligned teams create operational drag and how he helps companies save millions (like a recent $1.5M inventory win) by fixing communication rather than just tweaking spreadsheets. Matt and Sean also dive deep into the future of AI in business, debating whether we are heading toward a "Utopia" with Universal Basic Income or a total economic collapse. They discuss Sean's experience "Vibe Coding" a SaaS product using AI, the risks of buying a business versus starting one, and why an "irrational belief in oneself" is the most important trait for success. Check out the company: https://eightx.co👀 CONNECT WITH SEANSubscribe: https://www.youtube.com/@seanweisbrotLinkedIn: https://linkedin.com/in/seanweisbrotInquiries: welivetobuild@gmail.com🕒 CHAPTERS00:00 - What is EightX? (CFOs for E-commerce & CPG) 01:50 - Using AI to Predict Sales & Analyze Sentiment 03:50 - Why Profitability is a Human Problem (Not Math) 10:20 - How "Well-Meaning" Experts Create Operational Drag 12:15 - Saving $1.5M by Optimizing Supply Chain 13:40 - Sean's "Vibe Coding" Story: Building SaaS with AI 17:20 - AI Utopia vs. Dystopia: Will the Economy Collapse? 21:50 - Buying a Business vs. Starting from Scratch 24:00 - The Risks of Acquisitions & Operations 27:00 - The #1 Lesson: Irrational Belief in Yourself📈 WORK WITH ME▶ Startup Fundraising: https://welivetobuild.com/ai-startup-fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/collaborate▶ My AI/Automation Agency: https://optimai.ai

Can you land enterprise clients like Marriott and Panasonic without a massive sales team? Dima Syrotkin, founder of Panda Training, reveals his strategy for hacking enterprise sales: partnering with consulting firms who already have the trust (and the golf buddies) to close the deal for you. In this interview, Dima and Sean discuss why firing middle managers is a mistake, the reality of "AI shrinking companies," and why getting SOC2 and ISO certifications was the best $20k he ever spent. Dima also shares his personal struggle with defensiveness as a CEO and how hiring an angel investor full-time forced him to confront his own ego. Check out the company: https://pandatron.ai👀 CONNECT WITH SEANSubscribe: https://www.youtube.com/@seanweisbrotLinkedIn: https://linkedin.com/in/seanweisbrotInquiries: welivetobuild@gmail.com🕒 CHAPTERS00:00 - Why Companies are Stagnating (Coordination Problems) 01:46 - Why "Firing All Managers" (Holacracy) Doesn't Work 04:13 - Will AI Shrink or Grow Companies? 06:11 - How to Hack Enterprise Sales with Channel Partners 09:30 - The Risk of Relying on Partners (Conflict of Interest) 11:28 - Why You Need a Direct Sales Channel to Survive 14:26 - The Power of Face-to-Face Sales in Enterprise 16:04 - Landing the First Big Client (0 to $1M ARR) 17:40 - The Nightmare of Enterprise Security (300-Page Questionnaires) 21:00 - How to Get ISO/SOC2 Certified for $20k 24:40 - Hiring Top Talent After an Exit 27:47 - The #1 Lesson: Stop Being Defensive📈 WORK WITH ME▶ Startup Fundraising: https://welivetobuild.com/ai-startup-fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/collaborate▶ My AI/Automation Agency: https://optimai.ai

Is AI coming for your job, or just the boring parts you hate? Tim Cakir, an AI consultant who scaled his agency to nearly $1M ARR in the first year, reveals why he believes "boring work" is the enemy of productivity and how AI agents can eliminate it. In this interview, Tim shares the controversial story of how he helped a company replace 50 employees with an automation tool, why he believes leaders are manufacturing AI fear, and how he built a fully automated sales CRM using Claude and Make.com. He also debates Sean on the future of "Vibe Coding" and why the future of work might just be a black terminal screen. Check out the company: https://aioperator.com👀 CONNECT WITH SEANSubscribe: https://www.youtube.com/@seanweisbrotLinkedIn: https://linkedin.com/in/seanweisbrotInquiries: welivetobuild@gmail.com🕒 CHAPTERS00:00 - Why Leaders Are Creating AI Fear 03:32 - The "10-Year Clock" Until Work Becomes Optional 06:20 - Will AI Kill Junior Jobs? (The Skill Gap Crisis) 09:30 - How to Document Your Processes for AI 12:12 - "Vibe Coding" vs. Building Real Systems 16:40 - Automating the "Boring Work" (Sales CRM Example) 20:53 - Sean's Struggle to Automate His Podcast 24:30 - Why I Love Working in the Terminal (No UI) 28:50 - The Future of AI Agents & Automation 33:40 - Firing 50 People: The Hard Truth About Efficiency📈 WORK WITH ME▶ Startup Fundraising: https://welivetobuild.com/ai-startup-fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/collaborate▶ My AI/Automation Agency: https://optimai.ai