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

Shaun Maguire is a Partner at Sequoia Capital. At Sequoia he led their investment into SpaceX, The Boring Co and X among many others. Before Sequoia he co-founded a cybersecurity company called Expanse which Palo Alto Networks acquired for $1B. Before Expanse, Shaun worked at DARPA and was deployed to Afghanistan.

1. Why Iran is the Greatest Evil in the World:

• What specifically makes Iran the greatest danger to the world today?
• How should the US respond to the threat posed by Iran?
• Does the US have to go to war with Iran knowing that they now have nuclear weapons?
• How did the Biden-Harris administration worsen relations both with Iran and Saudi?
• Is Trump the best chance we have of bringing peace and stability to the Middle East?

2. Russia, Ukraine, Gaza and Israel: What is the Right Next Step:

• Does Shaun believe that the US should remove funding from Ukraine?
• How would Trump change the US' relationship with Putin?
• What does Shaun believe is the right next step for the US in Gaza and Israel?
• What does Shaun mean when he says the public have no idea how much crazy s**** happens?

3. Freedom of Speech and DEI: Remnants of the Past:

• Does Shaun believe we live in a society with freedom of speech? How does it differ between the US and Europe?
• Is Shaun negative on the future of Europe? Does he agree with Larry Summers that "it is a museum"?
• How does Shaun evaluate the state of diversity, equity and inclusion (DEI)?
• Why does Shaun believe that wokeness and cancel culture is one of the greatest dangers to society?
• When does Shaun believe that transgender becomes a problem in children? Where is the line?

4. The Election: Who Wins and What Happens:

• Does Shaun agree that Kamala is pulling ahead and Trump is now chasing her?
• How does Shaun analyse the chances of Trump winning?
• To what extent is it a real threat that there will be civil unrest if Trump does not win?
• Why does Shaun argue that too much blame is placed on Trump for Jan 6th and he did nothing that Hilary Clinton had not done in disputing prior elections?
• How does Shaun evaluate the appointment of JD Vance? Does Shaun agree with the echoes from the crowd for Trump to remove him?

5. Elon Musk, US Selling All BTC & Inside Sequoia:

• What does Shaun believe are the three qualities that make Elon Musk one of the greatest entrepreneurs of all time?
• Why does Shaun believe that it is a massive mistake for the US to sell all BTC holdings?
• Who is the best picker in Sequoia? Who is the best at sourcing?
• Does Shaun get told off internally for his opinions being shared so freely externally?
• What have been Shaun's biggest lessons from working alongside Doug Leone?

20VC: Sequoia's Shaun Maguire on Will We See WW3 Shortly | Why DEI is a Cancer for Society | Why Iran is the World's Greatest Evil | Why Trump is the Only Hope for Peace in the Middle East | Trump vs Harris: Who Wins & What Happens

Dax Dasilva is the Founder & CEO Lightspeed Commerce, one of the most incredible stories in startups. For 7 years they did not raise outside funding and ran a very profitable business. Ultimately they partnered with Accel and Innovia before going public on the Canadian Stock Exchange with just $70M in ARR. Lightspeed also undertook 9 acquisitions over the course of a four year period to consolidate the global market. Today they have a whopping $900M in ARR but are only valued at $2.6BN. Today we ask the question, is Lightspeed one of the public market's most misunderstood companies?

1. VC Funding is Distorting SaaS:

• Why did Dax decide not to raise money for Lightspeed in the early days?
• Does Dax believe Lightspeed would have been successful had they have raised a seed round like many do today in SaaS?
• Why does Dax believe venture funding is distorting a generation of SaaS companies today?
• How does Dax advise founders scaling their business today from $0-$1M in ARR?

2. What Went Wrong: The Founder Returns:

• Why did Dax feel he had to come back to the role of CEO in 2024? What was not working?
• What was the single biggest problem that the public markets had with Lightspeed?
• What were some of the biggest challenges that came with the intense amount of M&A?
• What would Dax most like to do that the public market will not allow?

3. What Makes a Great Leader: How it Changes:

• What required skills in leadership change with the changing scale of the company?
• What skill does Dax have that he is slightly ashamed of but has most contributed to his success?
• What did Dax not know when he founded Lightspeed that he wishes he had known?
• What question is Dax never asked that he should be asked more?

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?

David Cahn is a Partner @ Sequoia Capital, one of the great venture firms of the last 5 decades. Before joining the Sequoia partnership, David led Coatue's venture business as a General Partner and COO where he led investments in Hugging Face, Runway and Supabase. David also joined the boards of Weights & Biases and Replit.

1. AI's $600BN Question:

• What is the $600BN question in AI today?
• Is it possible to believe "AI will change the world" and "Capex levels are too high" at the same time?
• Why do the cloud players have to act now? When does the Capex reduce for them?
• How does Meta not having a core cash cow in cloud change the way they can respond?
• Why is all the risk today being borne by the large incumbents? Why is that good for startups?
• How will we see Satya and Zuckerberg change their narrative towards their Capex spend to the public markets?

2. The Data Centre is the Most Important Asset:

• Why does David believe that data centre is the most important asset?
• What does he mean when he says "servers, steel and power" are the pillars of AI?
• What happens when the development of models outpaces the construction of data centres?
• Why does David believe no one will ever train a frontier model on the same data centre twice?

3. The Biggest Opportunities in AI:

• Why does David believe the biggest opportunity right now is in the build-out of data centres?
• What does the supply chain look like for the build-out of data centres? Who are the winners?
• Why does David believe the biggest opportunity in finance is in creating new debt instruments that will allow the largest incumbents in the world to move this data centre spend off balance sheet?
• Why does David believe that AI will drive more energy innovation than any policy has done?

4. The Secrets of Sequoia: Inside the Walls of the Greatest Firm in Venture:

• What does David and Sequoia believe is the one definition of success in venture?
• Who is the best at find companies in Sequoia? Who is the best at picking?
• Why does David believe conviction, not picking is the hardest part in venture?
• How do Sequoia want to shape and mould every investor in the firm?

20VC: Sequoia's David Cahn on AI's $600BN Question | Why the Data Centre is the Most Important Asset | Servers, Steel and Power: The Core Pillars Powering the Future of AI

Ben Fiechtner is Chief Revenue Officer at Clari, where he drives global go-to market & revenue operations. Ben previously served as SVP at UiPath, growing their key accounts and regulated industry verticals from $150m to $450m. Before UiPath, Ben was at Salesforce where he held multiple senior roles, achieving significant year-over-year growth and always on the bleeding edge of Vertical teams.

1. How to Close Deals Faster:

• What are the top 3 ways sales reps can increase urgency in a deal cycle?
• Should reps be discounting? If so, what level can be appropriate?
• What is the right way to ask prospects for their internal buy process? How do you know if you are dealing with a champion?
• What are the single biggest reasons that deals are delayed in closing?

2. SMB to Enterprise: How and When:

• When is the right time to move into the enterprise?
• What are the single biggest mistakes startups make when making the transition?
• How does Ben advise startups to do it but with minimal spend and investment?

3. Verticalisation: Why, When and How:

• Why is it important for founders to consider a verticalised sales strategy? What are the benefits?
• When is the right time to consider a verticalised approach?
• What is the right way to resource each sales team for a verticalised approach?
• What are the biggest mistakes companies make when verticalising sales teams?

4. How to Hire the Best Reps:

• What are the top signals that a candidate will make for an amazing sales rep?
• What question does Ben ask in every interview? What do the best answers have?
• What are the biggest mistakes founders make when hiring sales reps?
• How fast do you know when a hire is a good hire or not?

Ethan Mollick is the Co-Director of the Generative AI Lab at Wharton, which builds prototypes and conducts research to discover how AI can help humans thrive while mitigating risks. Ethan is also an Associate Professor at the Wharton School of the University of Pennsylvania, where he studies and teaches innovation and entrepreneurship, and also examines the effects of artificial intelligence on work and education. His papers have been published in top journals and his book on AI, Co-Intelligence, is a New York Times bestseller.

1. Models: Is More Compute the Answer:

• How has Ethan changed his mind on whether we have a lot of room to run in adding more compute to increase model performance?
• What will happen with models in the next 12 months that no one expects?
• Why will open models immediately be used by bad actors, what should happen as a result?
• Data, algorithms, compute, what is the biggest bottleneck and how will this change with time?

2. OpenAI: The Missed Opportunity, Product Roadmap and AGI:

• Why does Ethan believe that OpenAI is completely out of touch with creating products that consumers want to use?
• Which product did OpenAI shelve that will prove to be a massive mistake?
• How does Ethan analyse OpenAI's pursuit of AGI?
• Why did Ethan think Brad, COO @ OpenAI's heuristic of "startups should be threatened if they are not excited by a 100x improvement in model" is total BS?

3. VCs, Startups and AI Labs: What the World Does Not Understand:

• What do Big AI labs not understand about big companies?
• What are the biggest mistakes companies are making when implementing AI?
• Why are startups not being ambitious enough with AI today?
• What are the single biggest ways consumers can and should be using AI today?

Delian Asparouhov is a Partner at Founders Fund and Co-Founder and President of Varda Space Industries, which is building the world's first space factories. At Founders Fund Delian has led deals in the likes of Ramp ($7BN) and Sword Health ($3BN) among others. Before joining Founders Fund, he was a Principal at Khosla Ventures, Head of Growth at Teespring, and Founder of a healthcare company called Nightingale.

1. Venture Capital: Winners, Losers and Everyone Else:

• Who are the Top 3 venture firms in the world today according to Delian?
• Why does Delian believe that Benchmark are not the firm they were?
• Who will be the winners in venture in the next 10 years?
• Who will be the losers in venture in the next 10 years?

2. Inside Founders Fund: What No One Sees:

• What are the most important and impactful elements of Founders Fund that no one knows about?
• What does Delian believe that the Founders Fund partnership will strongly disagree with him on?
• Why does Founders Fund believe the path of most resistance is the best way to make decisions?
• What single topic has Delian publicly disagreed with Peter Thiel on most? How did it go?

3. What Every Young VC Needs to Know:

• What are Delian's single biggest tips to young VCs looking to scale the VC ladder today?
• What are the five core pillars of venture according to Delian? What should young VCs focus on?
• Why does Delian disagree with Founders Fund partners that "the best founders do not need the help of their VCs?"
• Does Delian agree with Vinod Khosla that "90% of VCs do detract value?"
• What are the biggest ways that Delian believes VCs can and do detract value?

4. Europe Will Be Third World, Parenting and Marriage:

• Why does Delian believe that Western Europe will become like the third world?
• What are Delian's single biggest tips on finding a life partner?
• What have been the biggest changes to Delian since becoming a father?
• What question does no one ask Delian that someone should ask him?

Nilan Peiris is Chief Product Officer at Wise, where he leads on growth across channels including product and platform. Prior to Wise, Nilan was VP Growth at HouseTrip, in charge of scaling the company's growth in the European market. He's also worked as Chief Marketing Technology Officer at Holiday Extras, where he was responsible for all areas of technology, marketing and customer acquisition. Nilan also advises a number of early-stage startups on growth and getting to traction.

1. Lessons Scaling Transferwise to the First 1M Users:

• What growth tactics worked in scaling Wise to 1M users?
• What growth tactics did not work? What did they learn?
• What did Wise not do that Nilan wishes they had done?
• What single product change completely changed the trajectory of their growth?

2. How to Use Content to Crush Competition:

• What are the two different types of content that all companies must now make?
• What are the single biggest mistakes companies make with content today?
• What do you do when your competition can spend 7-8x more on marketing?
• Is SEO and SEM dead today or does it still play the same prominent role?

3. Wise's Framework on How to Win at Performance Marketing:

• What have been Nilan's single biggest lessons on how to win in performance marketing?
• What are the biggest mistakes companies make today in performance marketing?
• When is the right time to diversify and add new channels?
• What level of channel concentration would concern Nilan to see?

4. The Secret to Adding More Products:

• When is the right time to add a second product?
• How does Nilan define great product marketing today?
• How can one do amazing and targeted product marketing with several products aimed at different customers?
• What are the single biggest mistakes that companies make with brand marketing?

Jason Lemkin is one of the OG SaaS investors with all of his first five investments turning into unicorns with Pipedrive, Algolia, Talkdesk, Salesloft and RevenueCat all in his portfolio. SaaStr is the largest global community in SaaS and he has taught a generation the fundamentals of SaaS on saastr.com.

1. Wiz Rejects Google's $23BN Acquisition Offer:

• How does Jason analyse the price of the offer? $23BN for a $500M ARR business growing 120% YoY?
• What is the reasoning for Google in pursuing the acquisition?
• If Wiz had of proceeded in the process, what are the chances it would have made it through regulators?
• Why did Wiz walk away from the offer? If Jason were on the board, what would he have done?
• Is there a correlation between the downfall of Crowdstrike and Wiz turning down the offer?
• What does this mean for the M&A market moving forward?
• Will there be a secondary round now in place for Wiz at $23BN?

2. Crowdstrike: WTF Happens from Here:

• Did Crowdstrike manage the crisis in the right way? What would Jason have done differently?
• What is the bull case for Crowdstrike moving forward from this point?
• What are the bear case for the company? Could this snowball and be the end?
• What will this do to company requirements on having single point of failure solutions?
• Where will the market cap of Crowdstrike be at the end of 2024?

3. LegalTech: Show Me the Money: $1BN in a Single Day:

• Clio announced a $900M round at a $3BN valuation. How does Jason analyse this?
• What does Jason make of Harvey's $100M raise at a $1.5BN valuation?
• Why does Jason think 2025 will be the year for AI parity? Why will we see the majority of SaaS features be commoditised in 2025?
• What is the single biggest regret that Jason has in his investing career?

Kevin Hartz is a Co-Founder and General Partner at A*, an early-stage venture capital firm. Prior to founding A*, Kevin co-founded Eventbrite, a publicly traded company, and served as the CEO for the first 11 years of the company. Before Eventbrite, Kevin co-founded Xoom, a money remittance company that was acquired by PayPal in 2015 for over $1BN. Kevin is also a prolific angel investor having backed companies such as PayPal, Airbnb, Pinterest, Ramp, Trulia, and Anduril at the seed stage, and was an early investor in Uber, Palantir, SpaceX, Square, Gusto and many others.

1. What Makes the Best Founders:

• What questions does Kevin always ask founders in the investment process?
• Does Kevin prefer serial or first time founders? Why?
• Does Kevin prefer founders who are new to a problem or who are insiders and experts?
• When Kevin has gotten a founder bet wrong, what did he not see that he should have seen?

2. The Exploding Term Sheet That Cost $10BN:

• How did an exploding term sheet for the seed round of Airbnb cost Kevin $10BN?
• What did Kevin see in the seed round of Airbnb that so few other investors saw?
• Does Kevin agree that the best businesses often start off as ridiculous or toys?

3. From World's Greatest Angel to VC with $600M AUM:

• Why does Kevin think a barbell strategy of Seed and Series C is best today?
• Does Kevin agree that the Series B and growth stage is dead today?
• Why does Kevin strongly disagree that seed is the hardest stage of the market?
• Why does Kevin think that venture is less collaborative than ever?
• How does Kevin approach when to sell vs when to hold a position?
• What are his biggest lessons from seeding and holding Opensea?

4. Learning From the World's Best Investors:

• What have been Kevin's lessons from his relationship with Peter Thiel?
• What have been Kevin's biggest takeaways from investing alongside Roelof Botha in many deals?
• What have been Kevin's biggest lessons from watching and observing the great Pierre Lamond?