20Product: When to Hire a CPO, The Three Different Types of CPO, How To Know What You Need, How To Structure the Hiring Process, What Are the Must-Ask Questions, What Tests and Case Studies Should Be Used, How Should Their Compensation Package Be Structur

20Product: When to Hire a CPO, The Three Different Types of CPO, How To Know What You Need, How To Structure the Hiring Process, What Are the Must-Ask Questions, What Tests and Case Studies Should Be Used, How Should Their Compensation Package Be Structur

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor’s product vision and user experience, managing a 70-person product and design org.

Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe’s first PM Manager and helped grow the PM function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter.

David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos.

Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for Hewlett-Packard, Netscape Communications, and eBay.

Aparna Chennapragada is the former CPO @ Robinhood, revolutionizing consumer finance with commission-free investing. Prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products.

Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and one of the most popular newsletters on Substack.

For the last 7 years, Kayvon Beykpour has been at Twitter where he led all of the teams across Product, Engineering, Design, Research, and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015.

Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe’s Chief Product Officer. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, and served as CEO until Adobe acquired Behance in 2012.

In Today's Episode on How to Hire a Product Manager, We Discuss:

1.) When to Hire Your First PM:

  • What are the core signs that the founder must delegate and hire their first PM?
  • What are the first things that are breaking when you do not have one but need one?
  • How does the timing of the first PM differ when comparing B2B vs B2C?

2.) What is the Right Profile:

  • What should founders look for in this first PM hire? What traits make the best?
  • What are the biggest red flags in the personalities and styles of potential candidates?
    • Should they have experience in the product domain they are entering?
  • What are the single biggest mistakes founders make when analyzing the resumes of potential PM candidates? What should they look for in their resume?

3.) The Hiring Process: How To Hire a Product Manager

  • How do we structure and run the hiring process for this person?
  • What tests can we do to understand if they have the skill set we need for the role?
  • How do we structure a hiring panel to make this process more effective?
  • What are the biggest mistakes founders make in the hiring process for PMs?

Jaksot(1351)

20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China

20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China

Martin Casado is a General Partner @ a16z where he leads the firms $1.25BN infrastructure fund. At a16z, Martin has led investments in companies like Cursor, dbt Labs, and Fivetran to name a few. Before joining a16z, he co-founded Nicira, acquired by VMware for $1.26B. At VMware, he served as CTO of Networking. Widely regarded as a visionary in enterprise infrastructure, Martin has helped shape the modern cloud computing stack. Agenda: 00:00 – Analysis of Current AI Investment Landscape 04:45 – Will Anthropic Kill the AI App Layer? 09:20 – “The Oligopoly Is Coming—Just Like Cloud” 12:50 – Are AI Models Actually Terrible Venture Investments? 15:40 – Why it is BS to Put Down AI Apps for Having Temporary Revenue 21:30 – “Open Source Is a National Security Weapon—And We're Losing” 26:40 – “Have the Foundation Models of the Future All Been Founded Already” 34:30 – Why it is BS to Denigrate AI Apps for Having Low Margins 38:40 – Does AI Make 1x Engineers 10x or 10x Becomes 100x 44:10 – “We’re All Dead Wrong About AI and Job Loss” 50:30 – “The Only Sin in Venture: Backing the Wrong Winner” 55:10 – What People Think They Know About Wealth But Do Not

28 Heinä 1h 10min

20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

Fernando Fanton is one of the most respected product leaders in Europe, having held Chief Product Officer roles at Monzo and Just Eat. He previously led product and tech at Rappi, one of Latin America's most valuable startups. Today, Fernando is the CPO @ Property Finder; one of the biggest breakout unicorns from MENA.  Agenda: 00:00 – Is “having a vision” actually killing great product teams? 03:15 – Why do most products suck—and what separates the great ones? 07:20 – Should we kill the PM role entirely? Fernando says maybe. 11:45 – Is Monzo’s obsession with trust more powerful than speed? 16:10 – What’s the #1 reason internal tools will never replace SaaS? 21:00 – Will AI wipe out the need for designers and PMs? 26:30 – Is it arrogant for product teams to protect users from “bad” choices? 32:15 – What’s the future of product when OpenAI controls the whole stack? 37:40 – What Monzo product blew up—and why no one saw it coming? 42:55 – Can a bank built on principles really become a $100B company?

27 Heinä 1h 7min

20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?

20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?

Agenda: 00:00 – Did Jason Just Kill Replit?  03:45 – Why Claude Lies To You and Cannot Be Trusted 06:50 – You Cannot Trust Agents. Period. 10:20 – Why Windsurf Was Dead Without Claude 12:30 – Cursor vs. Lovable: What’s the Better Bet? 14:40 – Should You Still Invest in Cursor at $28B? 18:05 – Would You Bet on Anthropic at $100B or OpenAI at $300B? 24:15 – Inside OpenAI’s Secret Weapon: The Calvin French-Owen Memo 27:50 – Perplexity Just Crushed ChatGPT and Claude 32:15 – Will Cursor Build Their Own Models Before Anthropic Cuts Them Off? 33:20 – Figma’s IPO at $16B: Outrageous or Fair Game? 41:55 – 90% of Seed Funds Are Cooked—Is Rob Go Right? 52:15 – How Often Do You Meet a Founder Who Can Return the Fund? 1:08:00 – Which Seed Fund Would You Back Today?

24 Heinä 1h 21min

20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

Edwin Chen is the Founder and CEO of Surge. Founded in 2020, Surge has scaled to $1BN+ in revenue with zero external funding. At the same time, their competitor, Scale.ai raised over $1.3BN to reach $850M ARR. Today, Surge have the world’s largest model providers as customers and have just 120 employees.  Agenda: 00:00 — “Everyone Else Is Just a Body Shop” — Edwin Calls Out the Whole Industry 01:05 — Why 90% of Big Tech Is Wasting Time on Useless Problems 03:45 — “I Don’t Do 1-on-1s” — How Surge Kills Meetings and Still Moves 10x Faster 05:55 — Will a Single Person Build a $1B Company?  08:10 — 100x Engineers Are Real — Here’s How to Spot Them 12:10 — Why Most PhDs Are Useless in AI Training 14:20 — Built to a Billion With Zero VC — Edwin Explains How and Why 17:00 — “No Sales Team, No PR, No BS” — Why Surge Stays in the Shadows 21:15 — The Real Reason AGI Might Take Until 2040 24:45 — Will Synthetic Data Kill Human Labelling?  29:00 — “Academic Benchmarks Are a Scam”  31:05 — Why the Real Bottleneck in AI Isn’t Compute or Models — It’s THIS 33:00 — What Every AI Company Should Be Asking (But Isn’t) 35:15 — “No, I Wouldn’t Sell Surge for $100B”  39:00 — Is the Application Layer Doomed? Edwin Predicts the Future of AI Startups 46:30 — Have the Leading Foundation Models Already Been Founded?  48:10 — AGI Could Be Dangerous — And Most People Are Ignoring Why 20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

21 Heinä 1h 6min

20VC: Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale | Did Google Overlook a Goldmine in the Core Asset and Did Founders Leave a Sinking Ship | How Cursor and Cognition Deal with Ever Increasing Reliance on Anthropic

20VC: Cognition CEO Scott Wu on Acquiring Windsurf: The Process, The Deal, The Rationale | Did Google Overlook a Goldmine in the Core Asset and Did Founders Leave a Sinking Ship | How Cursor and Cognition Deal with Ever Increasing Reliance on Anthropic

Scott Wu is the co-founder and CEO of Cognition, the company behind Devin, the world’s first AI software engineer. On Friday last week they pulled off the acquisition of the year, acquiring Windsurf, following their licensing agreement with Google. Previously a world-class competitive programmer, he was a gold medalist at the International Olympiad in Informatics and a member of the U.S. Math and Physics Olympiad teams. Before Cognition, he was a founding engineer at Scale AI, helping shape the early AI infrastructure stack. AGENDA: 00:00 – Why are founders walking away instead of going down with the ship? 01:05 – How did Cognition pull off the $220M Windsurf deal in just 72 hours? 04:45 – What really happened behind closed doors the weekend Windsurf was acquired? 07:15 – Did Google overlook a goldmine in the Windsurf team and IP? 09:00 – Who are the 100 people that secretly shape the future of AI? 12:30 – Can application startups ever gain leverage over foundation model giants like Anthropic? 14:15 – Is coding about to be replaced by simply describing what you want? 17:30 – 50% of new code is AI-written. Where does that go next? 20:45 – “We’ve gone from 0 to $80M ARR in 6 months. Quietly.” 25:00 – Are IDEs and agents just the training wheels for the real future of software engineering? 28:20 – If you could only back one—OpenAI or Anthropic—who’s the better bet? 30:00 – Why has Cognition kept its insane growth a secret… until now?

18 Heinä 48min

20VC: Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not | Lovable vs Replit: Will These Be $100BN Businesses | Why Elon Could Beat Sam Altman with the New Grok | Why Every S&P 500 Company Will Buy Bitcoin?

20VC: Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not | Lovable vs Replit: Will These Be $100BN Businesses | Why Elon Could Beat Sam Altman with the New Grok | Why Every S&P 500 Company Will Buy Bitcoin?

Agenda: 00:00 Windsurf was dead—then this deal changed everything 05:00 The Windsurf x Google x Cognition saga explained 09:00 The OpenAI deal collapsed—what really happened 15:00 FTC rules forced a brutal deal structure—who lost? 17:00 The investors’ returns: who actually made money? 21:30 Will Google’s corp dev team get fired over this? 23:00 Cognition’s genius $220M acquisition of Windsurf: Most brilliant Deal of the Year 26:00 The biggest recruiting flex in Silicon Valley this year 35:00 “Roll your own SaaS” is complete nonsense 38:00 Lovable vs Cursor vs Replit: who wins the coding war? 41:00 Why Lovable could be the ChatGPT of builders 44:00 Will these vibe-coded apps become durable businesses? 48:00 The shocking churn rates hidden inside AI SaaS 55:00 Are these $2B valuations actually... cheap? 56:30 Grok just destroyed GPT-4 in benchmarks—WTF?! 01:01:00 Why Grok might overtake OpenAI in the next 12 months 01:11:00 Meta just invested $3.5B in Ray-Bans—WTF? 01:12:30 Should every S&P 500 company buy Bitcoin now? 01:15:00 Will Meta kill open source? What happens to Llama 5?

17 Heinä 1h 21min

20VC: Vlad Tenev on Robinhood’s $85BN Resurgence | Tokenizing SpaceX & OpenAI | Building Nine Revenue Lines Over $100M | Why Crypto Will Be Robinhood's Biggest Revenue Line | Why Stablecoins Will Replace Banking Rails

20VC: Vlad Tenev on Robinhood’s $85BN Resurgence | Tokenizing SpaceX & OpenAI | Building Nine Revenue Lines Over $100M | Why Crypto Will Be Robinhood's Biggest Revenue Line | Why Stablecoins Will Replace Banking Rails

Vlad Tenev is the Founder and CEO of Robinhood, the greatest story on Wall St of the last decade. In the previous 18 months, Robinhood has increased its net revenue by 58% to nearly $3B; a $500M loss in 2023 turned into a $1.1B profit in 2024. Robinhood’s stock is up roughly 4x, lifting their market cap to north of $80B. Today, Robinhood has nine lines of business that do over $100M in revenue.  Agenda:  00:00 – “Tokenization Is The Biggest Innovation in Finance” 03:28 – How Robinhood 4x’d Its Market Cap in 8 Months 06:40 – AI Writes 50% of All Net New Code at Robinhood 10:02 – Why Robinhood Built a Secret ChatGPT for Support 12:11 – The One Customer Type That Transformed the Business 15:29 – “CoreWeave Is Retail’s Way Into AI” — The Meme Stock Defense 18:05 – Inside Robinhood’s Tokenized Private Shares Product 21:23 – “Capital as a Service” — Vlad’s Wild Vision for Startup Fundraising 24:10 – The $100M Revenue Line Vlad Wishes He Could Kill 26:45 – Robinhood Is Building... Cash Delivery Trucks?! 29:55 – “We Were Shipping Nothing”: Vlad on the 2020–2022 Culture Crisis 33:20 – What Line of Business Will Be the Biggest For Vlad in 5 Years Time 35:11 – The One Competitor Vlad Actually Respects 36:55 – From Men’s Health to Japanese Toilets: Vlad’s Weirdest Quickfire Yet 38:40 – “I Was in the Dumps”: What 2022 Taught Vlad About Resilience 40:00 – Where Robinhood Is Headed: The Next Decade of Financial Infrastructure

14 Heinä 57min

20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025

20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025

Kieran Flanagan is the CMO at HubSpot, where he’s led the transformation of their growth strategy from SEO-led to multi-channel and AI-powered. Formerly SVP of Marketing, he helped scale HubSpot’s user base to millions and revenue past $2B. Before HubSpot, he drove breakout growth at Marketo and Salesforce. Kieran is one of the most respected voices in SaaS marketing and a pioneer in growth-driven content strategy. Agenda: 00:03 – The Death of Growth Teams? Kieran's Wild Prediction 06:44 – AI Innovation Pods: The New Org Structure for Startups 10:18 – Email Personalization That Tripled Conversions 13:21 – From Software Budget to Labor Budget: The Shift is Happening 16:35 – The Big Lie: Why Autonomous Agents Still Suck 19:24 – The Secret Sauce Behind HubSpot’s Email AI Stack 21:44 – Segment-Based Marketing Is Dead. Enter Micro Audiences. 24:15 – Content Collapse: Why Google Organic Is Getting Torched 30:52 – The Future of AI SEO: 1 Product, 100 Pages, Infinite Prompts 33:16 – Memory = Moat: Why ChatGPT Is Becoming Unbeatable 35:46 – Prompt Engineering is the New Coding: Here's How to Win 41:03 – The Death of the Middle Manager Marketer 46:17 – OpenAI vs. Anthropic: Kieran’s $400M Bet 48:00 – Europe Is Falling Behind: The Harsh Truth on Regulation 52:39 – CMO Playbook 2025: Micro-Audiences, Creator-Led, AI at Scale

11 Heinä 1h 15min

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