20Product: Calendly CPO Annie Pearl on Why All PLG Companies Eventually Need to Embrace Enterprise, Why it is Easier to Scale into Enterprise than Visa Versa and the Calendly PLG Playbook; What Works and What Does Not?
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Release Date: 08/31/2022
20VC: Four Traits of the Most Successful Founders | How to Hunt and Close Talent Like a Pro and Where All Founders Go Wrong | Lessons Raising $397M From the Best Investors in the World with Eléonore Crespo @ Pigment
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Eléonore Crespo is the Co-Founder and CEO @ Pigment, one of Europe’s fastest-growing companies. With Pigment, Eleonore has raised over $397M from the best in the world including ICONIQ, Greenoaks and IVP to name a few. Prior to Pigment, Eléonore was on the other side of the table as an investor with Index Ventures. In Today's Episode We Discuss: [04:10] “I had 3 surgeries. That’s when I knew I had to become a founder.” [06:50] Why Index Ventures isn’t on her cap table [08:40] Eleonore’s CIA-style co-founder hunt (she literally made a target list) [11:50] Co-CEOs: “We talk...
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20VC: Benchmark vs a16z: Why Stage Specific Firms Win | Windsurf Sells For $3BN | Decagon Raises at 100x ARR | Do Mega Funds Win the Future of VC | What Does Harvard's Losing Their For-Profit Status Mean for VC
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Today’s Topics: 04:44 Analysis of $3 Billion Windsurf Acquisition 12:39 Will Mega Funds Win the Future of Venture Capital 18:39 Does Every Fund Have to do Pre-Seed to Win Series A and B Today 27:53 Why AI Will Create Massive Unemployment 31:06 The $100,000 Bet on the Future of Work 35:52 Why Venture Has Become a Bundled Good 37:52 Why Stage Specific Firms Will Win: a16z vs Benchmark 40:16 What Does Harvard Losing It’s For Profit Status Mean for Venture 42:57 Why AI is Maiming and Not Killing Growth Companies on the Path to IPO 45:41 Decagon Raises 100x ARR: The Breakdown 52:50 Why...
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20VC Exclusive: Why Mega Platforms Will Win in VC | Why You Cannot Do VC If You Do Not Do Pre-Seed | Why Market Sizing is BS | Where Will Foundation Models Build/Buy Apps vs Where Will They Not with Bucky Moore
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Bucky Moore is a Partner @ Lightspeed Venture Partners, announced exclusively in the show today on 20VC. Prior to Lightspeed, Bucky spent an incredibly successful 7 years at Kleiner Perkins working with Mamoon Hamid to build one of the most successful early stage firms of the last decade. Bucky has made investments in the likes of Prisma, Netlify, Browserbase and more. In Today’s Episode We Discuss: 03:07 Big News: Joining Lightspeed Venture Partners 04:09 Why Mega Platforms Will Win the Next 10 Years of VC 09:33 Are Foundation Model Companies Good Venture Investments 16:04 What...
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20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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...
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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
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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...
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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
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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...
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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
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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:...
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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
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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...
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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
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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...
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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
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Rich Socher is the Founder and CEO of . 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,...
info_outlineAnnie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. The company now has over 10M users around the world and over 50,000 companies loving the product. As for Annie, before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70 person product and design org. Prior to Glassdoor, Annie led enterprise product teams at Box both before and after their 2015 IPO. If this was not enough, Annie is also on the Board of WorkRamp and Well Health.
In Today's Episode with Annie Pearl We Discuss:
1.) Entry into Product From Consulting:
- How did Annie make her way into the world of product and come to lead product teams at Box and GlassDoor?
- What are 1-2 of her biggest takeaways from her time at Box and GlassDoor? How did they impact her product mindset?
- What does Annie know now that she wishes she had known when she started in product?
2.) PLG vs Enterprise: What, When, How:
- Is it possible to do PLG and top-down enterprise strategy together from Day 1?
- Why does every PLG company eventually have to adopt an enterprise strategy?
- What are the single biggest challenges companies face when moving to enterprise?
- How do founders know when is the right time to make this transition?
- How do founders need to restructure their org to make the transition to enterprise?
3.) Building the Product Bench: Hiring:
- When is the right time to hire your first product leader? What are the core signals?
- What are the core character traits needed for a first product leader?
- How do we specifically structure the interview to test for them?
- Who do we bring into the interview process from other parts of the org?
- Do we do case studies with candidates? If so, how long do they have with the data? What is the difference between good vs great with case studies?
4.) Product Strategy, Reviews and Alignment:
- How does Annie assess how often product strategy should be reviewed? When should it change?
- How does Annie approach post-mortems? What is the right way to structure them?
- How does Annie create alignment between sales and product? Why is this so important?
- What is the single biggest product mistake Annie has made? What did she learn?