20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
Reggie Marable is the Head of Global Sales at Sierra, a conversational AI platform for businesses. Sierra enables companies like ADT, Sonos, SiriusXM, and WeightWatchers to build AI agents that transform customer experiences. The company has rapidly become a hypergrowth leader in Silicon Valley, recently securing a funding round that values it at $4.5 billion. Before joining Sierra, Reggie was the Head of Sales in North America at Slack and the Area Vice President of Enterprise Sales at Salesforce. In Today’s Episode We Discuss: 02:50 “What I Learned from Failing Early as a CRO” 06:06 The Most Effective Sales Strategy and the BS Sales Methodology 06:55 How to Build Sales Processes from Scratch 12:28 When and How to do Verticalised Sales Teams 14:15 How to Become World Class as Sales Prospecting and Outbound 17:21 How to Use Proof of Concepts to Win Enterprise Deals 22:04 Enterprise vs. Self-Serve: Both or One and How 30:09 Building a Sales Team from Scratch 37:39 Structuring the Hiring Process 41:14 How Founders F*** Up Hiring in Sales 46:25 Handling Salary and Title Expectations 51:36 How to Run Effective Deal Cycles 57:06:07 How to do Onboarding for New Sales Hires 59:07:48 How to do Post Mortems in Sales Processes 01:04:24 Negotiating Enterprise Deals 01:08:04 Quick Fire Round: Sales Tactics and Strategies
2 Maj 1h 25min
20VC: Why Fund Returners Are Not Enough Anymore | Why Sequoia Had the Best Strategy at the Worst Time | What it Takes to Be Good at Series A and B Today | Benchmark Leads Manus Round: Should US Funds Invest in Chinese AI
In Today’s Episode We Discuss: 03:56 Why The Risk Lever Has Been Turned Higher than Ever in VC 06:04 Why IRR is the Hardest Thing to Control 09:36 Is Lack of Liquidity Short Term Temporary or Long Term Structural 12:17 Why Fund Returners Are Not Good Enough Anymore 16:03 Sequoia: The Best Strategy at the Worst Time 26:30 What it Takes to be Good at Series A and B Today 34:14 Only Three Company Types Survive AI 41:35 ServiceNow: 25% Pop, WTF Happened 45:29 Palantir and SAP Ripping: Do Incumbents Win AI 49:43 Are Benchmark Wrong to Invest in Chinese Made Manus 01:00:52 Geopolitical Risks in Investments 01:11:36 European vs. US Tech Culture
1 Maj 1h 24min
20VC: VCs are Spreadsheet Monkeys and are Commoditised | Why Fees and Carry Misalign GPs and LPs | Why Founders Will Realise Multi-Stage Funds Damage Seed Rounds | Why We Need European Sovereignty More Than Ever with Taavet Hinrikus
Taavet Hinrikus is a Partner at Plural, the early-stage fund that backs the most ambitious founders on a mission to change the world through technology. He co-founded Wise in 2010, where he was CEO and later Chairman, which went public in the first-ever direct listing in Europe in 2021. Prior to that, Taavet was Skype’s Director of Strategy until 2008, having joined as its first employee. He’s been an active investor for more than a decade,with personal investments in the likes of Bolt and Synthesia. In Today’s Show We Discuss: 04:08 VCs are Spreadsheet Monkeys 05:41 Why Banker European VCs Suck More Than The Others 11:20 Why Serial Entrepreneurs Are Better 14:48 Why the 2:20 Fee and Carry Model in VC is Broken 18:01 What are the Biggest Ways VC Investment Decision-Making is Broken 28:26 Why is it BS when VC Firms Need Every Partner to Meet the Founder 31:24 When and Why Will Founders Realise Multi-Stage Firms are Bad Early Investors 34:35 Why Does Europe Need to Build it’s Own Tech Now More Than Ever 37:24 Will Putin Invade More European Countries 39:29 What are the Dangers of Having US Made Tech in Europe 47:12 How Does the Change in Relationship Between the US and Europe Impact How We Build Our Tech Ecosystem? 52:36 Quick Fire Questions and Reflections
28 Apr 58min
20Growth: Inside Kraken’s $1.5BN Growth Playbook: What Works, What Doesn’t and What No Founders Understand About Growth That Will Change Their Company with Mayur Gupta
Mayur Gupta is currently the CMO at Kraken, one of the largest crypto platforms in the world. Prior to that, he lead Marketing, Business Transformation and Growth at Gannett - USA Today Network, led Growth at Spotify and was the CMO at Freshly which eventually got acquired by Nestle. He was the first ever Chief Marketing Technologist at Kimberly Clark. In Today’s Episode We Discuss: 03:25 Biggest Growth Lessons from Spotify 08:21 Role of Marketing in Product-Led Companies 13:35 How to Build a Growth Engine 20:40 Organic vs. Paid Growth Strategies 27:36 The Branding Dilemma: Performance vs. Brand Marketing 28:37 Creating Demand: The Role of Upper Funnel Marketing 29:35 Balancing Investment: Immediate vs Long Term Bets 30:03 Channel Saturation and Experimentation 31:42 Growth Strategies and Performance Metrics 34:54 Growth: Big Swings or Moving % Points 40:04 Successful Growth Experiments and Tactics 44:56 Quick Fire Questions and Final Thoughts
25 Apr 52min
20VC: OpenAI's $3BN Acquisition of Windsurf: The Breakdown | Are Endowment Funds F******* & How LP Deployment to Venture Will Change in 2025 | Why Revenue Multiples are BS, The Rise of AI Rollups and Multi-Stage Funds Destroying Seed Investing
In Today’s Show We Discuss: 04:49 Breaking Down the $3BN Windsurf Acquisition 06:18 Why Sam Altman is Playing a Master Game 12:40 Why Multi-Stage Funds are Destroying Seed Managers 21:52 Are Endowment Funds F****** 27:38 What Would Rory Do If He Was CFO of an Ivy League Endowment Fund 43:38 The Denominator Effect and It’s Impact on Venture Allocations 49:36 Why Revenue Multiple is BS & What You Need to Know 51:34 The Rise of AI Rollup Plays & Are They Good Businesses 55:29 Competitive Markets: How to Make Money in Them? 01:02:58 Why If You Can Guarantee 5x, You Should Always Do the Deal 01:11:56 Is SF The Only Place to Be Building Today
24 Apr 1h 25min
20VC: Do Rich Founders Make Better Founders | The Best Performing Fund Would Only Back YC Founders on Their Second Time | Why SPACs Will Come Back | Why Short Sellers Should Be Banned | Is Trump Better for Business than Biden with Jason Wilk @ Dave
Jason Wilk is the Founder and CEO of Dave, the greatest turnaround in the public markets of the last 12 months. Dave went public with a market cap of $4BN, just months later the company had a market cap of $50M. Today, they are back with a market cap of $1.1BN. In 2024, CNBC named Dave the best-performing financial stock in the country, achieving 900% growth. In Today’s Episode We Discuss: 04:09 Do Rich Founders Make Better Founders 07:45 The Best Performing Fund Would Only Invest in YC Founders on Their Second Time 11:25 “We Went Public Too Late, It Was a Big Mistake” 17:53 Why Did Jason Choose to SPAC? 24:21 Why Does Jason Believe SPACs are Unfairly Demonised and Will Comeback? 29:47 How Does AI Change the Margin Structure of the Next Generation of Companies 33:14 Is Trump Better for Business than a Biden Administration? 38:35 Are We Heading into a Recession? Predictions for Next 12 Months? 46:26 Why Have No Neobanks Reached the Heights of Revolut in the US? 48:08 Why is the Opportunity in Low Income Banking Not High Income in the US? 50:07 Why Short Sellers Should Be Stopped and How Immoral They Are
21 Apr 58min
20VC: Foundation Models: Who Wins & Who Loses | How Economies and Labour Markets Need to Change in a World of AI | China vs the US in an AI Race: What You Need to Know | Rich Socher, Founder @ You.com
Rich Socher is the Founder and CEO of You.com. Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of the AI startup MetaMind, which Salesforce acquired in 2016. He is widely recognised as having brought neural networks into the field of natural language processing, inventing the most widely used word vectors, contextual vectors and prompt engineering. He has over 150,000 citations and served as an adjunct professor in the computer science department at Stanford. In Today’s Episode We Discuss: 04:10 Winners & Losers: OpenAI, Gemini, Claude 08:59 How Partnerships Could Decide the Winners in AI 12:42 China vs US: Who Wins the War for AI 25:50 How Society and Economics Needs to Change in a World of AI 34:04 What Jobs Will Be Replaced, What Will Not 36:04 How Europe Needs to Change It’s Approach to AI 41:06 How AI Will Change Health and Longevity 43:10 AI in Consumer and Enterprise Markets 49:30 Quantum Computing and AI Misconceptions 56:57 Longevity, Personal Reflections, and Future Outlook
18 Apr 1h 3min
20VC: Why Seed is for Suckers | a16z's $20BN Fund & Founders Fund's $4.6BN: What Makes Them So Good | Why Josh Kushner Is the Master of Venture Capital Strategy | Why Extended Private Markets Screw US Citizens with Jason Lemkin and Rory O'Driscoll
Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more. Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others. In Today’s Episode We Discuss: 04:23 What is Wrong with Billionaires on Twitter: Are They Depressed? 08:49 Why Does product Market Fit Mean Less Than Ever 11:50 Why is Venture Capital More Risky Than Ever and No One is Discussing It 16:17 Will Private Equity Save a Generation of SaaS Companies and VCs 23:53 a16z’s $20BN Fund: Seriously? 31:29 Why Josh Kushner and Thrive Capital are Masters of the World 38:21 Why is Seed Investing for Suckers 45:49 Why Are $50 Million Seed Funds Useless 46:21 Founders Fund Raises $4.6BN: Analysis 52:00 How WIll LPs Change Their Approach to Venture in the Next Five Years 59:53 When Will IPOs Comeback? 01:09:15 Why Does it Not Make Sense for the Best Companies to IPO 01:09:51 Lost Ethics and Morals in Founder Secondaries and Term Sheets 01:22:58 Quickfire: OpenAI, Cursor, Deel vs Rippling
17 Apr 1h 29min
