20VC: Why Every Startup Will Either Fail or Rebrand, How To Do OKRs The Right Way & How To Know The Reversible From the Irreversible Mistakes with Jack Groetzinger, Founder & CEO @ SeatGeek

20VC: Why Every Startup Will Either Fail or Rebrand, How To Do OKRs The Right Way & How To Know The Reversible From the Irreversible Mistakes with Jack Groetzinger, Founder & CEO @ SeatGeek

Jack Groetzinger is the Founder & CEO @ SeatGeek, the world's largest ticket inventory on the web serving more than 500,000 artists and teams in over 380,000 venues. To date, Jack has raised over $160m in VC funding with SeatGeek from the likes of John Locke @ Accel, Founder Collective, TCV and most recently a $57m Series D led by Glynn Capital Management. Prior to SeatGeek, Jack founded Scribnia, a web app that used collaborative filtering to recommend bloggers and blog content, sold to an ad network in 2009. Jack is also a Founder Partner @ Founder Collective and angel investor in Troops, Inc.

In Today's Episode You Will Learn:

1.) How Jack made his way into the world of startups and decided to reinvent the ticketing industry with SeatGeek?

2.) How does Jack think about the combination of technical vs commercial skills for founders today? Where has Jack struggled with this balance? What would his advice be to prospective founders? How does Jack use OKRs to drive efficiency at SeatGeek? How can OKRs be constructed the right way? What is a rate of failure that suggests you are being ambitious enough?

3.) Jack has raised multiple rounds and over $160m in funding, how have the rounds differed from round to round? How does what Jack wants from an investor differ with time? What one ability do truly unique board members have the ability to do? How does Jack think about board conflicts and the right way to communicate with boards?

4.) How does Jack determine when is the right time to raise big? What is the one core metric that says now is the right time? How does Jack think about both the diversification and mortality of customer acquisition channels? How have SeatGeek seen theirs fundamentally change over time?

5.) Jack led the $56m Toptix acquisition, how was the acquisition process for Jack? What were the big learnings for Jack in terms of buying something that is large? With the acquisition, how does Jack think about the balance between capital efficiency and aggressive growth? What would Jack have done differently with regards to their growth trajectory if he had his time again?

Items Mentioned In Today's Show:

Jack's Fave Book: Powerful: Building a Culture of Freedom and Responsibility

As always you can follow Harry, The Twenty Minute VC and Jack on Twitter here!

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Jaksot(1405)

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

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

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 Will 99% of Knowledge Work Will be Gone in 10 Years 27:12 How Will Data-Driven Feedback Loops Replace Technology as the Moat 36:08 Who Wins the Data Labelling Market? Who Loses? 38:23 Is Revenue BS in Data Labelling? Are Players Calling GMV Revenue?  45:20 Why is SaaS Dead in a World of AI? 51:23 Will the Phone be the Primary User Interface to an AI World? 57:07 Quickfire Round

1 Joulu 20251h 8min

20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

John McMahon is widely regarded as one of the greatest enterprise-software sales leaders of all time. He's the only person to have served as Chief Revenue Officer at five public software companies: PTC, GeoTel, Ariba, BladeLogic and BMC Software. He helped scale BladeLogic from a startup into a public company — ultimately leading to its ~$880M sale to BMC — and drove GeoTel into a multi-billion dollar acquisition. Today he sits on the boards of top names such as Snowflake and MongoDB, while also mentoring and influencing a who's-who of modern SaaS sales leaders. AGENDA: 03:33 The Art and Science of Sales: Insights from a Veteran 04:29 Adapting Sales Strategies in the Age of AI and PLG 07:47 The Ultimate Framework to do Deal Qualification 14:13 How to Drive Urgency and Maintain Sales Process 20:06 How to Hire the Best Sales Reps 25:11 Step-by-Step Guide to Training Sales Reps 45:22 The Mindset of the Best Sales Reps 54:55 Single Most Important Skill to Win in Sales

28 Marras 20251h 8min

20VC: Anthropic Raises $30BN from Microsoft and NVIDIA | NVIDIA Core Business Threatened by TPU | Sam Altman's "War Mode" Analysed | Sierra Hits $100M ARR: Justifies $10BN Price? | Lovable Hits $200M ARR & Rumoured $6BN Round

20VC: Anthropic Raises $30BN from Microsoft and NVIDIA | NVIDIA Core Business Threatened by TPU | Sam Altman's "War Mode" Analysed | Sierra Hits $100M ARR: Justifies $10BN Price? | Lovable Hits $200M ARR & Rumoured $6BN Round

AGENDA: 04:06 Anthropic's $30BN Investment from Microsoft and NVIDIA 07:01 Google vs. OpenAI: Sam Altman's "War Mode" Memo 15:27 NVIDIA's Customer Concentration: Bull or Bear 22:12 Is "War Mode" BS: Does Hyper-Aggressive Ever Work? 36:12 Sierra Hits $100M ARR: Justify $10BN Price? 46:14 Implementation is the Biggest Barrier to Enterprise AI Growth 01:04:04 Is LLM Search Optimisation (GEO) Selling Snake Oil? What AI is a Fraud vs Real? 01:14:27 Figma Market Cap: Is the IPO Market F****** for 2026

27 Marras 20251h 30min

20VC: Base44's Maor Shlomo on How Vibe Coding Will Kill SaaS and Salesforce | Why it is BS that Vibe Coding Platforms Do Not Have Defensibility and Bad Margins | Why He Worries About Google, Not Replit and Lovable | Why Long Anthropic, Not OpenAI?

20VC: Base44's Maor Shlomo on How Vibe Coding Will Kill SaaS and Salesforce | Why it is BS that Vibe Coding Platforms Do Not Have Defensibility and Bad Margins | Why He Worries About Google, Not Replit and Lovable | Why Long Anthropic, Not OpenAI?

Maor Shlomo is the Founder and CEO of Base44, the AI building platform that Maor built from idea to $80M acquisition by Wix, in just 8 months. Today the company serves millions of users and will hit $50M ARR by the end of the year. Before Base44, Maor was the Co-Founder and CTO of Explorium. AGENDA: 00:05 – 00:10: How Vibe Coding is Going to Kill Salesforce and SaaS 00:13 – 00:15: Do Vibe Coding platforms have any defensibility? 00:22 – 00:24: I am not worried about Replit and Lovable, I am worried about Google… 00:28 – 00:29: Margins do not matter, the price of the models will go to zero 00:31 – 00:32: Speed to copy has never been lower; has the technical moat been eroded? 00:47 – 00:48: How does Base44 beat Cursor? 00:56 – 00:57: Do not pay attention to competition: focus on your business 00:57 – 00:58: How Base44 is helped, not hurt by not being in Silicon Valley? 00:58 – 00:59: What percent of code will be written by AI in 12 months? 01:01 – 01:02: OpenAI or Anthropic: Why Maor is Long Anthropic? 01:03 – 01:04: If I could have any board member in the world it would be Jack Dorsey

24 Marras 20251h 11min

20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster

20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster

Max Altman is Co‑Founder & Managing Partner at Saga Ventures, a US$125 M early‑stage fund.  Before Saga Max was an investor with Apollo Projects, Hydrazine Capital and Altman Capital (where he helped deploy over US$500 M) into breakout names such as Rippling and Reddit. AGENDA: 03:55 – Venture Capital Is FULL of Tourists With Single-Digit IQs 06:20 – Inside the Madness of Parker Conrad: Genius, Chaos, and WTF Emails 10:35 – The Rippling Deal That Changed Everything 12:40 – Living in Sam Altman's Shadow: The Confession 17:30 – $200M Fund Mistakes: Max's Brutal Lessons From Hydrazine 22:05 – The $2B Reddit Return… and the $2B Left on the Table 25:00 – Why Climate Tech Is a Total VC Mirage 28:40 – The New Seed War: Can Anyone Survive Sequoia & Andreessen? 46:55 – Max's Boldest Predictions

21 Marras 20251h 19min

20VC: Cursor Raises $2.3BN: Who Wins the Coding War | Peter Thiel and Softbank Sell NVIDIA: Analysed | Why Venture Capital Will Hit $1TRN and the Opening of Retail | Why Stripe and the Best Companies Will Never Go Public

20VC: Cursor Raises $2.3BN: Who Wins the Coding War | Peter Thiel and Softbank Sell NVIDIA: Analysed | Why Venture Capital Will Hit $1TRN and the Opening of Retail | Why Stripe and the Best Companies Will Never Go Public

AGENDA: 04:47 Cursor Raises $2.3BN at $29BN Valuation 11:36 What Gemini 3 Means for Lovable, Cursor and Replit 30:54 Peter Thiel and Softbank Sell NVIDIA: The Bubble Bursting? 48:54 Oracle Credit Default Swaps: The Risk is Increasing 01:07:22 Stripe Does Tender at All-Time High: Why the Best Companies Will Never IPO 01:19:18 Why Retail WIll Cause a Surge of Capital into VC Funds

20 Marras 20251h 22min

20VC: Andrew NG on The Biggest Bottlenecks in AI | How LLMs Can Be Used as a Geopolitical Weapon | Do Margins Matter in a World of AI? | Is Defensibility Dead in a World of AI? | Will AI Deliver Masa Son's Predictions of 5% GDP Growth?

20VC: Andrew NG on The Biggest Bottlenecks in AI | How LLMs Can Be Used as a Geopolitical Weapon | Do Margins Matter in a World of AI? | Is Defensibility Dead in a World of AI? | Will AI Deliver Masa Son's Predictions of 5% GDP Growth?

Dr. Andrew Ng is a globally recognized leader in AI. He is Founder of DeepLearning.AI, Executive Chairman of LandingAI, General Partner at AI Fund, Chairman and Co-Founder of Coursera. As a pioneer in machine learning Andrew has authored or co-authored over 200 research papers in machine learning, robotics and related fields. In 2023, he was named to the Time100 AI list of the most influential AI persons in the world. Agenda: 03:19 What are the Biggest Bottlenecks in AI Today?  08:51 How LLMs Can Be Used as a Geopolitical Weapon 15:48 Should AI Talent Really Be Paid Billions? 29:07 Why is the Application Layer the Most Exciting Layer? 36:22 Do Margins Matter in a World of AI? 38:02 Is Defensibility Dead in a World of AI? 45:29 Will AI Deliver Masa Son's Predictions of 5% GDP Growth? 49:39 Are We in an AI Bubble? 57:31 Will Human Labour Budgets Shift to AI Spend?

17 Marras 20251h 2min

20Product: How AI Changes Product Design | Does the Design Phase Become Irrelevant in a World of Vibe Coding | The Five Pillars of Truly Great Product Design with Carl Rivera, Chief Design Officer at Shopify

20Product: How AI Changes Product Design | Does the Design Phase Become Irrelevant in a World of Vibe Coding | The Five Pillars of Truly Great Product Design with Carl Rivera, Chief Design Officer at Shopify

Carl Rivera is the Chief Design Officer at Shopify, where he previously led both Merchant Services and the Shop App as VP of Product. Before joining Shopify through its acquisition of Tictail, Carl was the co-founder and CEO of Tictail, the "Tumblr for e-commerce," where he built one of the most beloved design-forward commerce platforms of its era. AGENDA: 05:05 Biggest Lessons from Selling My Company to Shopify 09:55 Where Does Shopify Suck at Product: Lessons from that? 17:37 What makes Truly Great product Design: The Five Pillars 31:02 The Future of Design in an AI-Driven World 36:00 Do We Skip the Design Phase in AI: Figma's Evolving Role in Design 40:09 Remote Work vs. In-Person Collaboration: Where Remote Loses? 42:43 What Happens to the Vibe Coding Market 47:06 Product Management and Team Dynamics 59:48 Does AI Favour Incumbents or Startups

14 Marras 20251h 11min

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