20VC: Inside Legora: $100M ARR in 18 Months | Jude Law Generated $50M in Sales Pipeline: The Economics Broken Down | Competing Against Harvey, the 800 Pound Gorilla | Why Legora is Undervalued at $5.5BN with Patrick Forquer, CRO @ Legora

20VC: Inside Legora: $100M ARR in 18 Months | Jude Law Generated $50M in Sales Pipeline: The Economics Broken Down | Competing Against Harvey, the 800 Pound Gorilla | Why Legora is Undervalued at $5.5BN with Patrick Forquer, CRO @ Legora

Patrick Forquer is the Chief Revenue Officer at Legora [https://legora.com?utm_source=chatgpt.com], the fastest growing enterprise business to ever hit $100M in ARR and now on track to hit over $250M in ARR by the end of the year. They recently raised a $550 million Series D at a $5.55 billion valuation, led by Accel, note 20VC did participate and is an investor in the company. AGENDA: 0:00 – How Jude Law Generated $50 Million in Qualified Pipeline 4:00 – Why Implementation is Your Secret Weapon to Win in AI 5:50 – Why AI Enterprise Sales Require "Legal Engineers" 7:45 – The 6-Figure Rule: When Should Humans Control Sales 12:55 – Is Legora Vastly Overvalued at $5.5BN? 15:45 – How to do global expansion in a world of AI 18:00 – How to Win Supremely Competitive Markets 24:45 – Why Giving Your Product Away for Free is a Death Sentence 33:55 – Legora's Onboarding and Training Playbook for Sales Teams 38:25 – Spotting Red Flags: How to Know if a Sales Rep Will Fail in 45 Days 46:30 – How to Structure Sales Commissions in a World of AI 49:40 – How to do Revenue Forecasting in a World of AI 1:00:30 – Will companies vibe code solutions and no longer buy a SaaS products?

20VC: What I Learned from 100 of the Best CEOs in the World | What I Learned from Staying with Mr Beast for 3 Weeks | How We Will Spend More on Tokens than Salaries with Cliff Weitzman, Speechify

Cliff Weitzman is the Founder & CEO of Speechify AI. He solved his dyslexia and ADHD in college by building a Voice AI agent that's now used by over 60 million people and has over 1 million five-star ratings. Over 200 software and AI engineers work on Speechify which won the Apple Design award last year. AGENDA: 00:00 — Until You Hit $100K Do Not Spend on any Channel Other than Meta 04:53 — How I hacked the college system by applying to 26 universities 06:33 — The "Great Guy" yearbook prank that accidentally outed me 08:35 — What I learned from hunting down the top 100 CEOs in the world 11:51 — The "Warrior" rule: Why I force my senior leaders to edit their own ads 13:52 — Why companies are like bodybuilders: The Bulking and Cutting cycle 17:34 — I test 1,000 AI-generated ads every single day 20:13 — How I built a custom AI ad platform in just four days 23:19 — The one $3,000,000 ad I filmed in a hot tub with red headphones 32:15 — Why we will soon spend more on AI tokens than employee salaries 34:55 — "I'm disappointed in you": The 1,000-credit daily AI requirement 36:31 — How LLMs helped me find my father's cancer when doctors couldn't 41:13 — Why 40% of billionaires are dyslexic—and why you should be too 45:41 — Why I refuse to hire anyone who has worked at Google 47:05 — I flew into a war zone in Ukraine just to keep one engineer 55:49 — Why performance reviews are a total waste of time 58:32 — QA is the most valuable skill in the world (and you're probably bad at it) 01:03:59 — Why we keep our valuation and funding a total secret 01:07:51 — The "Virus" Strategy: How Logan Paul hijacked the WWE 01:11:32 — What I learned from sleeping at Mr Beast's house for three weeks 01:14:15 — How we made a 36X return on Nvidia using high-leverage options 01:23:44 — I found the hacker who stole $200k—then I hired him 01:32:45 — Why I spent 11 days sleeping in a Walmart parking lot

20VC: Mag7 Earnings: Google & Amazon Win - Meta and Microsoft Falter | Anthropic's $50BN Raise & What it Means for a Potential IPO | Atlassian, Twilio and Five9 Beat: The SaaS Apocalypse Over? | Sierra's $15B Valuation: Peak or Potential

AGENDA: 00:00 – Mag Seven Earnings: The "Super Bowl" of Tech Results 04:45 – Google's Cloud Explosion & The AI Search "Disruption" That Never Came 15:53 – Microsoft's $190B Bet: Is AI the Only Thing Keeping Growth Flat? 21:59 – Meta's $150B Future Bet vs. Wall Street's Need for Spreadsheets 28:50 – Palantir's Home Run: Why Big Companies Spend Big Money on AI 38:43 – Apple's Quiet Consistency & The Stealth Inflation of Memory Chips 41:11 – The SaaS Apocalypse Over? Atlassian and Twilio Lead the Re-acceleration 50:50 – Anthropic's $50B Raise & The Math Behind Token vs. Salary Spend 01:05:59 – Sierra's $15B Valuation: Replacing the $400B Customer Service Labor Market 01:13:39 – Musk vs. Altman Trial: Statute of Limitations, Standing, & Private Diaries 01:17:42 – The End of Managers? Brian Armstrong & The Rise of the "Individual Contributor"

20VC: Shopify's Tobi Lütke on How AI is a Scapegoat for Mass Layoffs & What Will Labour Markets Be in the Future | Why We Need More Scrutiny on Charitable Giving, Governments are Bad at What They Do and Trump Derangement Syndrome in Canada

Tobi Lütke is the co-founder and CEO of Shopify, the global e-commerce titan with a $160 billion market cap. Under his leadership, the company generates over $7 billion in annual revenue and has seen its valuation grow nearly 100x since its 2015 IPO. Today, Shopify has over 8,000 employees and AI now generates over 50% of the Shopify's code. AGENDA: 00:10:36 - The $160 billion CEO who did not want to be CEO. 00:11:51 - Why don't companies become public? Because it is much worse to be an untrusted public company. 00:16:53 - Why we are about to enter a golden age of entrepreneurship. 00:17:54 - Why AI is being used as a scapegoat for mass layoffs. 00:17:41 - How will labor markets change in a world of AI? 00:24:43 - Why we should praise Elon Musk so much more than we do. 00:27:59 - Why we need to place more, not less, scrutiny on charitable giving. 00:31:56 - Why we have too many charity dollars and why they are inefficient. 00:34:57 - Why governments are so bad at what they do. 00:37:27 - The Trump derangement syndrome in Canada. 00:39:51 - Why will governments regulating technology push us into the hands of the Chinese? 00:41:59 - Europe has to get rid of the bullshit green parties and go back to Prussian economics. 00:48:29 - Why is looking at the ticker such bullshit? 00:50:48 - Why young coders are not as advantaged in AI as I thought they would be. 00:53:56 - The best engineers in Shopify are not writing code anymore and the AI does it for them. 00:56:40 - The cheat code for any career from the billionaire founder of Shopify.

20VC: Inside Clay's Sales Playbook Scaling to $100M ARR | How to Set Sales Comp Plans | How to Read Sales Talent Linkedin Profiles | What Profiles to Hire & Fire | How to Increase Performance and Speed in Sales Teams with Becca Lindquist

Becca Lindquist is Head of Sales at Clay, one of the fastest-growing AI companies to reach $100M+ ARR. She previously helped scale dbt Labs into a category-defining data platform, building and leading high-performing sales teams. Before that, she was an early sales leader at Heap, where she played a key role in scaling the GTM motion. AGENDA: 00:00 Why most sales reps plateau—and when you should leave your company 02:45 Should you jump from SaaS to a hot AI startup right now? 05:30 How long is too long at one company—and what great tenure actually looks like 08:00 How to read a LinkedIn profile like a world-class sales leader 13:30 The biggest hiring mistake sales leaders make (and how to catch it fast) 16:00 Titles vs salary: what actually predicts a great hire 20:00 What early-stage founders must look for in their first sales hires 24:00 How to evaluate AI startups: PMF, retention, and real signals that matter 27:00 Sales comp decoded: quota, OTE, and how to design winning incentives 33:00 How to build a high-performance sales culture (and avoid a toxic one) 41:00 What makes a true champion—and why most reps get this wrong 45:00 Weekly forecasting: how elite sales teams run pipeline reviews 50:00 Are SDRs dead? How AI is really changing outbound sales 52:00 Why every rep owns pipeline—and how top teams generate it 54:30 The future of sales productivity: AI tools, workflows, and what actually works