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's Big Fat Quiz of the Year: Founder, Fund and Breakout Company of 2025 | Predictions for 2026: The Company to Buy, The Biggest Short | Why Salesforce Could Win 2026 and The Tailwinds NVIDIA Will Face
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
AGENDA: 03:48 Founder of the Year 2025 06:58 Product of the Year 10:05 Fund of the Year 20:52 Breakout Companies of 2025: Who Made the Biggest Impact? 26:57 Biggest Surprises of 2025 32:57 Predictions for 2026: Top Performing Tech Stocks of the Year 35:25 B2B Stocks to Watch 38:31 Why Salesforce Could Be the Buy of 2026 47:11 Google, Meta, Apple, NVIDIA, Microsoft: Buy One, Short One 55:38 IPO Speculations: Who Will Go Public in 2026 01:00:57 The Impact of AI on Employment
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20Product: On Running's CPO on How to Create Emotion Through Product | Why 99% of Products Fail and How to Create Cults Around Products | The Biggest Product Mistakes On Have Made & Lessons Learned with Gérald Marolf
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Gérald Marolf is the Chief Product Officer at On Running. Gérald oversees the full range of On’s shoes, apparel and accessories to make sure each delivers performance, comfort and style. Before On, Gérald spent over a decade building consumer brands with collaborators such as Microsoft and Ferrari. AGENDA: 00:00 – Why Most “Great Products” Fail to Create Emotion 03:00 – How Perfume Taught Me Everything About Desire & Product 06:10 – The Brutal Reality of Building Physical vs Digital Products 16:00 – Why “Simple Design” Is Overrated and Dangerous 23:00 – Why Vuori is...
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20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
AGENDA: 03:32 Lightspeed's $9 Billion Fundraise 05:20 The Impact of Mega Funds on Seed VCs 10:09 The Supercycle of Growth and Late-Stage Investments 13:06 Disney Invests $1BN into OpenAI and What It Means 23:19 Oracle Hit Hard: Is Now the Time to Buy 28:34 Broadcom's Market Cap Drop and Anthropic’s AI Chip Orders 35:04 Cursor Competes with Figma: The Convergence of Design and Coding Tools 46:20 The Biggest Danger for Incumbents: Being Maimed by AI 55:28 Boom Supersonic Raising $300M to… Power Data Centres… WTF 01:00:24 Will SpaceX IPO at $1.5TRN and The Elon Option Value
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20VC: a16z’s David George on How $BN Funds Can 5×, Do Margins & Revenue Matter in AI & the Most Controversial Bet at a16z
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
David George is a General Partner at Andreessen Horowitz, where he leads the firm’s Growth investing team. His team has backed many of the defining companies of this era, including Databricks, Figma, Stripe, SpaceX, Anduril, and OpenAI, and is now investing behind a new generation of AI startups like Cursor, Harvey, and Abridge. AGENDA: 03:05 – Why Everyone is Wrong: Mega Funds Does Not Reduce Returns 10:40 – Is Public Market Capital Actually Cheaper Than Private Capital? 18:55 – The Biggest Advantage of Staying Private for Longer 23:30 – The #1 Investing Rule for a16z: Always Invest...
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20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Raaz Herberg is the Chief Marketing Officer and VP Product Strategy at Wiz, the fastest-growing cloud security company in history. As one of the first 10 employees, Raaz has helped scale the business from nothing to a multi-billion-dollar ARR business. Before Wiz, Raaz was a Senior PM working on Azure at Microsoft. AGENDA: 03:51 What No One Knows About The Early Wiz Days 09:08 Most Effective Marketing Wiz Ever Did? Lessons from it? 24:11 How Wiz Mastered Enterprise Sales and Product Development 39:12 The Value of Proof of Concept an Why Everyone Gets Them Wrong 44:23 Why The Best Leaders...
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20VC OGs: SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price | Airwallex Raises $330M and The Battle with Keith Rabois | Netflix Acquires Warner Brothers | IPO Market Predictions for 2026: Anthropic, Stripe, Databricks and SpaceX
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
AGENDA: 03:46 SpaceX's $800 Billion Valuation: A Deep Dive 09:18 IPO Market Predictions for 2026 18:18 Netflix's Bold Move: Acquiring Warner Brothers 27:43 Tiger's New Fund Strategy 33:02 Databricks' Head of AI $500 Million Seed Round 36:38 Harvey Raises $160M at an $8BN Valuation 48:22 Will LLMs Kill the App Layer 01:02:02 Google's AI Capabilities 01:06:58 Chinese Open Source Models in US Startups 01:08:57 Airwallex Raises $330M at an $8BN Valuation 01:23:50 Prediction Markets and Insider Trading
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20VC: Kalshi’s $1BN Raise, the Polymarket Feud, and the Battle to Replace Traditional Media
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Tarek Mansour is the Co-Founder and CEO @ Kalshi, the leader in the world of prediction markets. Just last week, they announced their $1BN raise at an $11BN valuation. In total, they have raised $1.59BN from some of the best, including Sequoia, a16z, General Catalyst, IVP, Meritech, and more. They also last week announced exclusive partnerships with CNN and CNBC, marking their move into mainstream media and news. AGENDA: 03:28 Why Did Kalshi Need to Raise $1BN 10:35 Why is Kalshi vs Polymarket Such a Fierce Rivalry? 20:44 The Future of Prediction Markets 25:09 Why Does Kalshi Partner...
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20VC: Inside Bending Spoons Acquisition Machine: Evernote, Eventbrite, Vimeo | How Evernote Evaluates Acquisitions and New Product Ideas | How Evernote Mastered Product Launches, User Retention and Monetisation with Federico Simionato
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Bending Spoons is the acquisition machine of the tech world. They have acquired the likes of Evernote, Vimeo, Eventbrite, Streamyard and more. However, they never open their gates to the secrets behind Evernote’s product machine. Today that changes with Federico Simionato joining 20Product. Fede has been a Product Lead at Bending Spoons for 8 years where he has led product teams at Evernote, WeTransfer and more. AGENDA: 03:02 From Dentist Games to $11BN Bending Spoons 04:54 Advice for Aspiring Product Managers 05:38 Building a Coveted Brand at Bending Spoons 07:43 Evaluating and...
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20VC: Thrive & OpenAI Partnership | Eventbrite Acquired for $500M | Databricks Raising $5BN at $134BN Valuation: Cheap or Not? | Why SaaS is Like Japan and The TAM Trap in Software
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
AGENDA: 04:20 Thrive and OpenAI Partnership 07:14 Databricks Raising $5BN at $134BN Valuation: Cheap or Not? 17:39 Eventbrite Acquired by Bending Spoons for $500M 21:39 Pagerduty’s $1BN Market Cap, Just 2x Revenue 26:59 The TAM Trap: Why SaaS Is Like Japan 37:42 Lessons from Companies Hitting $100M ARR 44:57 The Future of Labour Markets is F****** 52:10 The Importance of Compounding in Investments 56:45 The Relevance Game in Venture Capital 01:05:01 Supabase at $5BN or Lovable at $6BN: Which One?
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20VC: Scale, Surge, Turing, Mercor: Who Wins & Who Loses in Data Labelling | Is Revenue in Data Labelling Real or GMV? | Why 99% of Knowledge Work Will Go and What Happens Then? | Why SaaS is Dead in a World of AI with Jonathan Siddharth @ Turing
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Jonathan Siddharth is Founder and CEO of Turing, one of the fastest-growing AI companies advancing frontier models. Jonathan has led the company to an astonishing $300M ARR with just $225M raised and a profitable company. A Stanford-trained AI scientist, Jonathan previously helped pioneer natural language search at Powerset, which was acquired by Microsoft. AGENDA: 03:35 Data, Compute, Algorithms: What is Most Abundant? What is Lacking Most? 09:18 What Does No One Know About AI’s Data Requirements That Everyone Should? 17:05 The Biggest Challenges Enterprises Have with AI Adoption 20:38 Why...
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?