The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch – Details, episodes & analysis

Scott Gorlick was employee #99 at Uber. Over 6 years, Scott built Uber in Atlanta and helped the company scale from 10 cities to $10B in revenue. Scott is also a prolific angel investor having written early checks into Lime and Standard Cognition to name a few.

1. The Driver Acquisition Playbook: Scaling to 1M Drivers

• How did Uber acquire 1M drivers? What was the playbook?
• What worked? What did not work?
• How much of a role did driver-to-driver referral payments have in driver acquisition?
• What did Lyft do on the driver acquisition side that Uber should have done?
• What did the retention look like for drivers on a 30, 60 and 90 day period?

2. The City Expansion Playbook:

• What was the expansion playbook that Uber used for new cities?
• What worked in ramping demand in a new city? What did not work?
• How much of a role did promotions and discounting play? Lessons from them?
• Why did Uber often let Lyft launch in a new market first? What was the benefit of this?
• How did Scott see the maturation rate change with new markets opening? How fast did each subsequent market reach profitability?

3. Travis Kalanick and What Uber Could Have Been:

• How would Uber be different today if Travis was still in charge?
• What are the biggest mistakes that Dara has made with their M&A strategy?
• What are some of Scott's biggest leadership lessons from working with Travis?
• How did Travis create such strong followership and cult around him?
• What were the single biggest management mistakes made by Travis?

Arvind Narayanan is a professor of Computer Science at Princeton and the director of the Center for Information Technology Policy. He is a co-author of the book AI Snake Oil and a big proponent of the AI scaling myths around the importance of just adding more compute. He is also the lead author of a textbook on the computer science of cryptocurrencies which has been used in over 150 courses around the world, and an accompanying Coursera course that has had over 700,000 learners.

1. Compute, Data, Algorithms: What is the Bottleneck:

• Why does Arvind disagree with the commonly held notion that more compute will result in an equal and continuous level of model performance improvement?
• Will we continue to see players move into the compute layer in the need to internalise the margin? What does that mean for Nvidia?
• Why does Arvind not believe that data is the bottleneck? How does Arvind analyse the future of synthetic data? Where is it useful? Where is it not?

2. The Future of Models:

• Does Arvind agree that this is the fastest commoditization of a technology he has seen?
• How does Arvind analyse the future of the model landscape? Will we see a world of few very large models or a world of many unbundled and verticalised models?
• Where does Arvind believe the most value will accrue in the model layer?
• Is it possible for smaller companies or university research institutions to even play in the model space given the intense cash needed to fund model development?

3. Education, Healthcare and Misinformation: When AI Goes Wrong:

• What are the single biggest dangers that AI poses to society today?
• To what extent does Arvind believe misinformation through generative AI is going to be a massive problem in democracies and misinformation?
• How does Arvind analyse AI impacting the future of education? What does he believe everyone gets wrong about AI and education?
• Does Arvind agree that AI will be able to put a doctor in everyone's pocket? Where does he believe this theory is weak and falls down?

Alexis Ohanian is the Founder and General Partner of Seven Seven Six, an early-stage venture capital firm with $970M AUM. Prior to 776, Alexis was the Co-Founder of Initialized, one of the most successful early-stage firms in history with their first fund returning 56x DPI. Before Initialized, Alexis was a Partner at the world-famous Y Combinator and before that was one of the Co-Founders of Reddit.

1. $31M in Revenue: The P&L of a Sports Team:

• What are the core revenue drivers for Angel City Football Team?
• How did Alexis convince Tony @ Doordash to write the largest-ever brand sponsorship check to have the Doordash name on the Angel City shirt?
• How much money does Angel City make from ticket sales per year?
• What does the revenue from merchandise look like for Angel City? How has it changed with time?

2. How to Spend $31M Annually To Run a Team:

• What are the single biggest costs in running a sports team?
• Does Alexis believe that salary caps are good or bad for leagues?
• How much money is spent by clubs on content and software today? How should that change?

3. More Cash in Sports Than Ever:

• Prices for teams are at an all-time high. Are we in a bubble for sports assets?
• What remains under-priced and what is over-priced today?
• What are the pros and cons of private equity entering sports ownership in a meaningful way?
• Who is the worst sports team owner who despite his mismanagement, still made billions?

4. Alexis Ohanian: AMA:

• How did Alexis and Serena William's children become millionaires through sports team ownership?
• How did Alexis turn a $10,000 check into $17.1M?
• How did a $10,000 check into a shoe company make Alexis $7M?
• Why does Alexis believe that sports becomes even more valuable in a world of AI?

Dave Powers serves as President and CEO of Deckers Brands, a global footwear and apparel company where he focuses on the company's five high-performing brands: UGG®, Teva®, Sanuk®, HOKA One One® and Koolaburra®. Prior to Deckers, he held executive leadership roles at Converse and Timberland, where he led worldwide retail merchandising, marketing, visual and store design as well as the creation of a sustainable line of footwear and apparel.

1. The Unlikely CEO of a Global Footwear Company:

• How did Dave make his way into the world of consumer and fashion from the ground up?
• Why did Dave never think he was the type of person to be a CEO?
• What does Dave know now that he wishes he had known when he started his career?

2. From $1.1M Acquisition to $1.4BN Revenues: The Hoka Story:

• Why did Deckers acquire Hoka for $1.1M? What did they see in this, at the time, futuristic running shoe that no one else saw?
• Was the growth of Hoka linear or were there needle-moving moments that propelled the brand?
• What did they do so right that led to their success?
• What would Dave have done differently in the Hoka journey if he had his time again?

3. From $14.7BN Acquisition to Oprah's Favourite: The UGG Journey:

• How much of a needle mover was it for UGG when Oprah added it to her list of favourite items?
• Why did UGG go through a tough period? What did they do wrong?
• What does it take to resurrect a brand? How can they bring UGG back to life and make it cool?

4. From Abercrombie to LVMH: An Analysis of the Industry:

• How does Dave analyse the rise and fall of Abercrombie and Hollister? Where did it go wrong?
• What does Dave believe LVMH are the best in the world at? What does he learn from them?
• How important is it for consumer companies to have a hero product?
• How can consumer companies scale to mass markets without losing their core audience?

Gustav Söderström is the Co-President, CPO & CTO at Spotify. Gustav has been instrumental in taking Spotify from a 30-person operation in Sweden when he joined to being the global leader of the space.

Scott Belsky is Adobe's Chief Product Officer and Executive Vice President, Creative Cloud. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. 

Tomer Cohen is the Chief Product Officer @ Linkedin where he is responsible for setting and executing the global product strategy at LinkedIn.

1. Why AI Is Now the Product that UI Serves:

• Why does Gustav believe that AI is now the product?
• How has the importance of UI changed with the rise of AI?
• How did TikTok change the product paradigm over the last few years?

2. What Matters More Models or Data:

• What is more important the size of the model or the amount of data a company has?
• Will companies use many models at the same time?
• Why will companies using many models at once create a huge opportunity for startups?
• Will every company have their own model? What will be the decision-making framework of whether to have your own model or leverage another?
• How does the rise of AI change how companies approach data acquisition, collection and cleaning?

3. The Workforce Needs to Change with AI:

• How do product leaders and teams need to change in an AI-first world?
• What do designers need to do to stay up to date in an AI-first world?
• What does it mean to be good at prompting? How can people get good at prompting?
• Why will AI kill companies that charge by the hour?
• Why will seat pricing die in a world of AI? What will be the business model for AI?

4. Incumbents vs Startups: Who Wins:

• Do incumbents win in a world of AI or do startups?
• Why is AI primed for incumbents to win and move fast in a way they could not in prior technology cycles?
• What are the biggest hurdles and challenges incumbents have to face that startups do not?
• What are the biggest barriers that startups have to win in a world of AI that incumbents do not have?

Peter Lacaillade is a Managing Director @ SCS Financial Services where he leads its private investment program where he oversees the firm's activities in private equity, opportunistic credit and private real assets. Peter has been an early backer of Thrive, Founders Fund, a16z, Greenoaks and 20VC. Before SCS, Peter was an Associate at HarbourVest Partners in its Secondary Group where he analyzed venture capital, growth equity and buyout investments.

1. Becoming One of the Great LPs in Venture:

• How did Peter make his way into the world of fund investing as an LP?
• What does Peter know now that he wishes he had known when he started as an LP?
• Why does Peter believe now is the best time to be investing in newer, emerging managers?

2. How to Pick the Best Venture Managers:

• What are the commonalities in the best VCs Peter has invested in?
• How important is track record for Peter when evaluating managers?
• What mistakes has Peter made when it comes to manager selection? What did he learn?
• How do the best managers build relationships with their LPs?

3. Building a Portfolio That Can 5x:

• In a venture fund portfolio, what is the distribution between those that outperform, perform as planned and then underperform?
• How does Peter invest in both large franchises and emerging managers with a barbell approach? How much in established franchises and how much in emerging managers?
• Are managers actively marking down their portfolios in the last 18 months? Who has been the best at this and who has been the worst? How much should portfolios be marked down?
• How does Peter evaluate the compression of deployment timelines we saw in the last 18 months?

4. A Breakdown of the LP Landscape:

• Family Offices: What are the biggest dangers of having family offices as LPs? Why do multi-family offices tend to be better?
• Endowments: Are they really as stable as people think they are? What separates a good vs great endowment? Who stands out?
• Fund of Funds: Why does Peter think fund of funds deserve more credit? How should managers think about working with FoFs most effectively?
• What is the right level of concentration managers should have between these different LP profiles?
• What are the biggest mistakes emerging managers make when approaching LPs?

Davis Smith is the Founder and Chairman of Cotopaxi, an outdoor brand with a humanitarian mission. The company has assisted over 4 million people living in poverty. The company has been profitable for the last 4 years and is expected to do $160M in revenue in 2023, up from $55M just two years before. In April 2023, Davis resigned after 10 years as CEO to lead a mission for his church in Brazil for three years. Davis is an EY Entrepreneur of the Year and was recognized as Utah's Businessperson of the Year in 2022. He is an adventurer who has floated the Amazon on a self-made raft, kayaked from Cuba to Florida, and explored North Korea.

1. From Selling $6M Worth of Pool Tables to the Amazon of Brazil to Founding Cotopaxi:

• How did Davis scale a pool table business to $6M in revenue?
• What were Davis' biggest takeaways from building the Amazon of Brazil, raising millions in VC funding and the business failing?
• How did depression and 36 hours on a sofa lead to the a-ha moment for Cotopaxi?

2. The Billion Dollar Company, Rejected by 100 Investors:

• How was the early fundraising journey for Davis with Cotopaxi? Why did so many investors say no?
• What was the best VC meeting he has ever had? Why do women understand Cotopaxi better?
• What does Davis believe are the biggest misalignments between VCs and Founders?
• Why does Davis believe we need a new type of financial product to fund long term projects?
• What are the biggest elements of fundraising that Davis believes founders do not understand?

3. Scaling Cotopaxi to $150M in Revenue:

• What are Davis' biggest lessons on what works and what does not from scaling Cotopaxi to $150M in revenue?
• Why did Davis not lay anyone off but decide everyone should take a pay cut instead? How did that go down?
• Why does letting people leave work earlier lead to better talent wanting to join your company?
• Why does Davis believe that you absolutely can build a huge business with balance in your life?

4. Life, Parenting, Marriage:

• Why does Davis believe that so many entrepreneurs chase the wrong thing? What do they chase? What should they be chasing instead?
• How does Davis analyze his relationship to money today? Does it make you happy?
• What does great parenting mean to Davis? How has that changed over time?
• How does marriage change when comparing pre-kids and post-kids?
• Was Davis nervous about becoming a father for the first time at the age of 24?

Steve Goldberg is the Chief Revenue Officer at Salesloft, the sales engagement platform that was acquired by Vista in 2022 for $2.3BN. Prior to Salesloft, Steve was Group Vice President of Enterprise at Yext and before that was a Senior VP @ InsideSales.com.

1. Becoming a Sales Leader:

• When did Steve first fall in love with sales?
• Why does Steve believe sales is more psychology than anything else? What can sales reps do to master the psychology of their prospects?
• What does Steve know now about sales that he wishes he had known in the beginning?

2. How to Close Prospects Faster Than Ever:

• How does Steve build relationships with prospects very fast? What questions does he ask?
• How does Steve know if he is really speaking to a buyer? What are the signals?
• How does Steve advise sales reps on getting multiple relationships within an account to prevent the potential of losing your champion?
• How does Steve feel about discounting? When is the right time to do it?

3. How To Do The Best Deal Reviews:

• What makes good vs great deal reviews? Who is invited? Who is not?
• Who sets the agenda? Who is responsible for what?
• How do deal reviews change throughout the quarter and throughout the year?
• Is a deal slipping into the next quarter an acceptable excuse for a sales rep to give?

4. How to Ensure Renewals in a World When They are Not Guaranteed:

• Have all budgets centralized back to the control of the CFO?
• Are people right to say that no CFOs are buying new technology today?
• What is the best way to show to customers the value you provide?
• Why does Steve believe revenue operations is the most valuable role within an org?

Sam Corcos is the Co-Founder & CEO @ Levels, the company helping you see how food affects your health with data from biosensors like continuous glucose monitors (CGMs). To date, Sam has raised over $89M for Levels from the likes of a16z (Jeff Jordan sits on his board), Founder Collective, Breyer Capital and Shrug Capital to name a few. Prior to Levels, Sam founded two prior companies, CarDash; a Y Combinator company that makes automotive repair and maintenance convenient. Before Cardash, Sam founded, Sightline Maps, an intuitive platform for 3D printing and visualizing topographical maps, marketed primarily towards the U.S. military.

1. The Founding Moment:

• What was the a-ha moment for Sam with the founding Levels?
• What were the big mistakes Sam made with prior companies that he did not take with him to Levels?
• What does Sam know now that he wishes he had known when he started Levels?

2. How to Fundraise Like a Pro:

• Why does Sam believe that founders should take as many meetings with VCs as possible?
• What are the biggest mistakes founders make when meeting investors?
• Should founders meet with associates in the fundraising process?
• What does Sam mean when he says, "you have to create theater" when pitching?

3. How to Extract the Most Value from Your Investors:

• What have been Sam's biggest lessons on how to put your investors to work?
• What is the right and most strategic way to ask investors for specific help?
• How can founders create a competitive environment where VCs are competing to help?
• Which investors have been the most helpful?
• Why are post-IPO operators the best angels to have as investors?
• How has the a16z platform team been such a needle mover?

4. How to Find Your Partner and Master Parenting:

• What does Sam mean when he says he had a "one pager" in what he wanted in a partner?
• What was in the one-pager? How did dates respond?
• What are the biggest mistakes people make when dating?
• What is Sam most nervous about on becoming a parent?
• How does Sam think having a child will impact his marriage?

Sanjit Biswas is the Founder and CEO @ Samsara, allowing businesses that depend on physical operations to harness Internet of Things (IoT) data. Over the last 8 years, Sanjit has scaled Samsara to $1BN in ARR and a public company with tens of thousands of customers. Before Samsara, Sanjit was the CEO and co-founder of Meraki, one of the most successful networking companies of the past decade. Sanjit grew Meraki from his Ph.D. research into a complete enterprise networking portfolio. Meraki's sales doubled every year from inception and in 2012, Cisco acquired Meraki for $1.2 billion. Huge thanks to Doug Leone for some fantastic question suggestions pre this episode.

1. From Founding to $1BN in ARR in 8 Years:

• What was the founding a-ha moment for Sanjit with Samsara?
• Sanjit sold his prior company Meraki for $1.2BN, what worked with Meraki that Sanjit took with him to Samsara? What did not work that he left behind?
• What does Sanjit know now that he wishes he had known when he started Samsara?

2. The Man Who Found Product Market Fit Time and Time Again:

• What is the one single moment that Sanjit believes you know you have product market fit?
• What are the biggest mistakes founders make when chasing product market fit?
• How does being a bootstrapped company change how a company approaches chasing PMF?

3. Mastering a Multi-Product Company:

• How do you know when it is the right time to launch a second product?
• Does the second product have to make the first product better?
• What are the biggest mistakes companies make when going multi-product?

4. The Art of Great CEOship:

• Does Sanjit believe that the best CEOs are the best capital allocators?
• What has been the single best and single worst capital allocation decision in Samsara's journey?
• What are the biggest mistakes Sanjit has made in leadership? How did he learn and grow from them?