The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Carvana is one of the most wild stories in the public markets. The company IPO’d with a market cap of $2BN before skyrocketing to $60BN, only for the company to lose 99% of it’s value hitting a bottom of $400M market cap. Today the company is stronger than ever and with a market cap of $41BN. Joining us in the hotseat is Dan Gill, Carvana’s CPO, the man who oversees all technology functions, as well as strategic partnerships for the business. In Today’s Episode with Dan Gill We Discuss: From $60BN to $400M Market Cap: What did Carvana do that Dan wishes they had not done? What did Carvana not do that Dan wishes they had done?  How do you maintain morale in a team when the company has lost 99% of it’s value?  From $400M Back to $40BN Market Cap: What have been the core needle movers in Carvana’s market cap surging? How does the Carvana business model benefit from economies of scale? How does vertical integration of the different products Carvana sells change the margin structure of the business?  The Future of Carvana: Why does Dan believe there is a massive market for Cavana in selling new cars? Why does Dan want to move into the peer to peer market, a market where so many before have failed? Why does Dan think Carvana should sell Chinese cars on the platform if American citizens want to buy them?  What revenue line does Carvana not have today that Dan believes will be the biggest in 10 years time?  Product Advice, North Star Metrics, Idea Selection: What is the product advice that Dan gives more than any other? How does Dan advise startup founders on how to know they have the right north star metric? What is his framework? How does Dan advise founders on how to select the right idea to work on? What is Dan’s prioritisation framework for if an idea will have a larger enough impact and is therefore worthy of being worked on?  

Mike Maples is one of the OG seed investors of the last two decades. As a co-founding Partner at Floodgate, Mike has been on the Forbes Midas List eight times in the last decade. Some of Mike’s investments include Twitter, Twitch.tv, Clover Health, Okta, Outreach, Chegg, Demandforce, and Applied Intuition. In Today’s Episode with Mike Maples We Discuss: 04:02 Does Seed Even Make Sense as an Asset Class?  05:16 Fund Size and Strategy: How to Do a 10x Fund? 08:12 Follow-On Investments: Are they BS? 16:41 Finding Inefficiencies in the Market 26:31 Exit Strategies and Liquidity Events: When to Sell? 35:14 How Floodgate Lost Billions Missing Airbnb and Pinterest 35:43 3 Frameworks for Evaluating Startups 36:23 Case Studies: Zoom and Okta 43:34 How to Truly Analyse Product-Market Fit 45:22 Challenges with Overfunding Startups 50:02 2024 in Review: Company and Fund of the Year 54:25 Predictions for 2025  

Matt Plank is Rippling's Chief Revenue Officer where he oversees all Sales and Account Management functions in the US and Internationally. Matt joined Rippling in the very early days when Parker Conrad (founder) was building V1 in a basement with $0 in revenue. Today the company is a market leader with 100s of $Ms in ARR. Prior to Rippling, Matt was a Sales Director @ Zenefits where he helped the company scale to $70M in ARR.  In Today’s Show with Matt Plank We Discuss:  08:25 Challenges and Strategies in Outbound Sales 10:29 Building Effective Sales and Marketing Partnerships 13:37 Founders and Sales Playbooks: Who Should Create Them? 20:45 Pricing Strategies and Customer Success 24:43 Discounting and Urgency in Sales 33:57 Building Relationships for Successful Deals 34:22 Effective Deal Reviews: Asking the Right Questions 35:30 Pipeline Reviews: Frequency and Participants 35:59 Handling Deal Slippage: Acceptable vs. Non-Acceptable Reasons 39:17 Maintaining Morale in Volatile Times 42:14 Outbound Sales Strategy: Lessons Learned 46:03 Scaling Sales Teams: Hiring and Promoting 47:15 Challenges and Strategies in International Markets 01:00:45 Signs of Scaling Issues in Sales Leadership  

Daniel Dines is the Founder & CEO @ UiPath, one of the most incredible journeys in startups. For 10 years, UiPath was a bootstrapped company that scaled to just $500K in revenue. Then it all changed, product market fit became obvious and the rest is history. The company went on to raise funding from Sequoia, Accel, Kleiner Perkins and more. Today, the company is worth over $10BN, listed on the NASDAQ and does $1BN+ in revenue. In Today’s Episode with Daniel Dines We Discuss: 1. The Future of LLMs: Why does Daniel believe that we are at the upper end of scaling laws and more compute will not lead to increased performance? Does Daniel believe we will see a world of many specialised models or fewer generalist models? OpenAI, Anthropic, Xai. Which would Daniel most want to invest in? Why them? 2. Is RPA F******* in a World of Agents: What is the core difference between RPA and agents? How do the tasks they complete differ? Why must we have a neutral meta layer coordinating RPA processes and agents? Why will siloed applications like Salesforce be unable to expand beyond their initial function?  Why does Daniel believe that agents will not complete tasks but make recommendations? 3. The Future of Work: WTF Happens with Agents: How long will it be before agents are fully utilised in the enterprise? What is the role of the human in a world of agents? What are the single biggest concerns of enterprises considering implementing agents in their companies? Why has GenAI not been successful in enterprise so far? Will this change? 4. Daniel Dines: The Billionaire Behind the Brand: How does Daniel deal with the loneliness of being CEO? What problem did Daniel struggle with for much of his twenties and thirties? How did he overcome it? Why does Daniel fear that he is becoming more and more disconnected?  Why does Daniel believe 1-1s are BS? What is Daniel’s single biggest advice to a new parent today?