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

Jamin Ball is a Partner @ Altimeter Capital where he sits on the board of Airbyte, Clickhouse, dbt Labs, Prisma, Tabular. Jamin has also led investments in Deel, MotherDuck, Personio and Starburst. Prior to Altimeter, Jamin spent 5 years at Redpoint where he led investments in Workato, Monte Carlo, Cityblock Health, Root Insurance.

Ed Sim is one of the best seed round investors in venture as the Founder and Managing Partner @ Boldstart, Ed focuses specifically on developer, infra and SaaS at pre-seed and seed round. Over the last decade, Ed has backed some of the best including Snyk, BigID, Kustomer, Front and Superhuman.

1. How to Invest Successfully in 2024:

• What are the three biggest mistakes growth investors can make in 2024?
• Why should founders not start a platform company?
• What were Jamin and Ed's biggest mistakes from the ZIRP era?
• How does Jamin justify paying an $8BN price for Hopin? What were his lessons?

2. The M&A Markets in 2024:

• Did Figma kill the M&A markets for 2024? What should we expect in M&A?
• Why will private companies buying private companies be a massive segment in 2024?
• What are Ed and Jamin's biggest tips to founders considering selling their company in 2024?

3. When Will IPOs Come Back:

• What will be the catalyst to the opening of the IPO markets?
• Will Stripe and Databricks go public in 2024? What others should we expect?
• What are the three requirements for a company to go public in 2024?

4. Firesales: Investors Need Cashback:

• Why does Ed believe now is the time in the cycle where late-stage investors want cash back to distribute back to their LPs or to recycle?
• What should we expect to see in terms of acqui-hires and firesales?
• What are the different incentives when comparing founders vs early stage VCs vs late stage VCs when it comes to acquisitions?

Nick Tomaino is the Founder and General Partner @ 1confirmation, one of the leading seed firms fueling the decentralization of the web and society. The fund started with $26M and the firm now has over $1B in assets under management. Nick is famed for being one of the first investors in OpenSea.

Kyle Samani is the Co-Founder and Managing Partner @ Multicoin Capital, one of the leading crypto native funds of the last decade with positions in Solana, FTX, Fractal, and Helium to name a few.

1. Moving Away from a Shitcoin Casino:

• What will it take for crypto to move away from being shitcoin casino?
• Why does Nick believe that "crypto has been a free for all and greed got the better of people"?
• Why does Nick believe that crypto shilling will reduce the amount of violence in the world?

2. FTX: The Biggest Ponzi Scheme in Plain sight:

• How does Kyle reflect on SBF and FTX today? Should he have known it was a fraud?
• How did Nick see so far ahead of time that SBF was not genuine?
• What are the most striking lessons when comparing Coinbase's Superbowl advert to FTX's?

3. Where Politics and Crypto Collide:

• SBF was one of the largest donors to Biden, what does this say about the rise of "crony capitalism"?
• What candidates running in the election will be best for crypto?
• Why will Trump win the election and be the first President to rule from a prison cell?
• Why is the strategy pursued by Gensler and the SEC so flawed?

4. The Great NFT Comeback, The Crypto IPO Season:

• What will be the next crypto company to IPO? When?
• When will NFTs come back? What will cause this?
• Will Opensea ever be worth $13BN again? What is their future?

Joining Harry in the hot seat today is Jason Lemkin, Founder @ SaaStr and one of the OG SaaS investors of the last decade. The discussion today is broken into two segments:

• Breakout company
• Best early-stage fund
• Best late-stage fund
• Most surprising event
• Founder of the Year

• Does the IPO window open?
• Do Stripe, Databricks, and more go public?
• What happens to early-stage venture markets?
• Does the growth stage come roaring back?
• What happens to the M&A market?
• How does Trump change the startup ecosystem?
• Will a generation of young VCs be washed out the system?
• Will a ton of venture firms shut down?

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?