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

This episode is brought to you by Capchase, helping software and hardware companies close deals while accessing TCV upfront. Learn more at capchase.com/20vc.

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

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

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

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

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

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

Please read the offering circular and related risks at invest.modemobile.com. This is a paid advertisement for Mode Mobile’s Regulation A+ Offering. Past performance is no guarantee of future results. Investing in private company securities is not suitable for all investors because it is highly speculative and involves a high degree of risk. It should only be considered a long-term investment. You must be prepared to withstand a total loss of your investment. Private company securities are also highly illiquid, and there is no guarantee that a market will develop for such securities. DealMaker Securities LLC, a registered broker-dealer, and member of FINRA | SIPC, located at 105 Maxess Road, Suite 124, Melville, NY 11747, is the Intermediary for this offering and is not an affiliate of or connected with the Issuer. Please check our background on FINRA's BrokerCheck.

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

Victor Lazarte is a General Partner @ Benchmark, one of the mot renowned venture firms in the world. At Benchmark, Victor has led deals into the likes of HeyGen and Mercor. As an angel, he was the first investor and board member of Brex, and as a Founder he scaled Wildlife Studios, bootstrapping into the largest gaming company in LatAm, with about 4 billion downloads. 

In Today’s Episode We Discuss:

04:10 Lessons Scaling Wildlife Studios to 4BN Downloads

04:49 Why Predicting the Future is Wrong When Starting a Company

07:11 Three Different Categories of Company in an AI World: Who Wins & Loses?

09:25 Why You Should Always Ask What a Founder Does in Their Free Time?

17:30 Two Traits That All the Best Founders Have?

23:17 Why If You Start a Company in SF You are 1,000x More Likely to be Successful?

35:30 Why Spreadsheet SaaS Investing is Dead

36:10 Why Replacing Humans is the Most Exciting Opportunity in AI

37:02 Why Knowledge Work Will Be Destroyed and What Happens Then?

37:30 Why China is a Stabilising Force for the US

38:59 China vs. US: The AI Race

42:33 Why All Students Today Should Study Computer Science

44:38 Why Portfolio Construction is BS

47:04 What Makes Peter Fenton One of the Best Ever

51:31 Why Duolingo Will Be One of the Most Valuable Companies in the World

01:00:17 Quick Fire Round: Insights and Predictions

Aatish Nayak is the Head of Product at Harvey where he oversees product vision, strategy, design, analytics, marketing, and support. This is his third hypergrowth AI unicorn having previously held product leadership roles at Scale AI from 40 to 800 people, and Shield AI from 20 to 100 people. 

In Today’s Episode We Discuss:

04:21 Biggest Product Lessons from Scale AI

7:18 Why Product Managers Are Wrong: They are not the CEO of the Product

12:28 Why Market Selection is More Important than Anything Else

16:40 If Distribution is King then Product is President

22:06 Effective Product Strategy and Execution

26:24 How to Write the Best PRDs

31:01 Balancing New Features and Technical Debt

33:17 Analysing Retrospectives and Postmortems

33:55 Introduction to Pre-mortems

38:25 Biggest Product Mistakes and Lessons Learned

41:40 Evaluating AI Models and Lessons Learned

45:03 The Future of AI in Product Management

55:21 What Should Product People Learn to Win in a World of AI

59:37 The AI Talent War in San Francisco

01:01:26 Quickfire Round