Akshay Kothari is Co-Founder at Notion, one of the fastest-growing companies of the last decade. Akshay has run every function in the company from sales, to marketing to finance and even led their fundraising efforts raising $340M+ from Sequoia, Index and Coatue with the latest round pricing them at $10BN. Before Notion, Akshay was VP Product at Linkedin for 5+ years, leading all of their content efforts. He joined LinkedIn when his previous company, Pulse, was acquired by LinkedIn in 2013.

In Today's Episode with Akshay Kothari We Discuss:

1. Founder Mode, Veto Powers and Focus:

• Does Akshay agree with "founder mode"? What are the biggest downsides to founder mode that not enough people are discussing?
• Why does Akshay believe that the single greatest power of a founder is their "veto power"?
• What is the biggest opportunity that Notion jumped on that they should not have done?
• What is the biggest opportunity that Notion did not jump on that they should have jumped on?

2. Raising $50M @ $2BN Valuation:

• Why did Ivan and Akshay decide to do this raise when they did not even need the money?
• How did the fundraising process for this round go? Why did they choose Coatue and Index?
• Why did Sequoia say no to this round?
• With the benefit of hindsight, what does Akshay wish that they had done differently?

3. Raising $270M @ $10BN Valuation:

• How did Sequoia come back into the frame with this round? Why did they say yes here when they did not before?
• Why does Akshay believe that of all the investor brands, Sequoia is the most powerful? In what way does having Sequoia as an investor change the trajectory of the company?
• Is Akshay concerned about how he will be able to scale into the $10BN valuation?
• How does Akshay address the challenge of bringing new team members in with stock options priced at $10BN? How much of a blocker is that?

4. Boards and Social Media are F*******:

• How is the way in which boards are constructed broken?
• How does Akshay believe that boards should be constructed?
• What roles should founders hire for in their board members?
• Why is Akshay most concerned about the "Tiktokification of everything"?
• Why does Akshay believe that social media has never been more concerning?

Shardul Shah is a Partner at Index Ventures and one of the greatest cyber security investors of the last two decades. Among his many wins, Shardul has led rounds in Datadog, Wiz, Duo Security, Coalition and more. Shardul is also the only Partner investing at Index to have worked in every single Index office from London, to SF, to NYC to Geneva. Prior to Index, Shardul worked with Summit Partners, focusing on healthcare and internet technologies.

In Today's Episode with Shardul Shah We Discuss:

1. Investing Lessons from Wiz and Datadog:

• Why does Shardul believe that TAM (total addressable market) is BS?
• Why does Shardul believe that every great deal will be expensive?
• How does Shardul evaluate when to double down and concentrate capital vs when to let someone else come in and lead a round in an existing company?
• How does Shardul think about when is the right time to sell a position in a company?

2. How the Best VCs Make Decisions:

• How does Shardul and Index create an environment of truth-seeking together, that is optimised for the best decision-making to take place?
• What are the biggest mistakes in how VCs make decisions today?
• Why does Shardul believe that all first meetings should be 30 mins not 60 mins?
• Why does Shardul believe it is so much harder to make investment decisions when partnerships are remote? What is better remote?

3. The Core Pillars of Venture: Sourcing, Selecting, Securing and Servicing:

• Which one does Shardul believe he is best at? What is he worst at?
• Does Shardul believe with the downturn we have moved into a world of selection and not just winning every new deal?
• Does Shardul believe that VCs provide any value? What are the biggest misnomers when it comes to "VC value add"?

4. Lessons from the Best Investors in the World:

• Who is the best board member that Shardul sits on a board with?
• What has Shardul learned from Gili Raanan and Doug Leone on being a good board member?
• What have been some of Shardul's biggest investing lessons from Danny Rimer?
• Why does Shardul hate benchmarks when it comes to investing?

Mike Hudack is the Co-Founder and CEO of Sling, a peer-to-peer payments app whose vision is to simplify the way the world connects financially. Previously, he held roles at Monzo Bank as Chief Product Officer, Deliveroo as Chief Product and Technology Officer, and Facebook where he led ads product and sharing product.

In Today's Episode with Mike Hudack We Discuss:

1. Product: Art vs Science:

• What is the true art of product? What makes the great product leaders and PMs?
• Is simple always better in product? How do you retain product simplicity with time?
• When should data be used over intuition in product building?

2. Lessons from Leading Ads at Facebook:

• What are Mike's single biggest product lessons from building the ads product at Facebook?
• How did a meeting with Mark Zuckerberg discussing a product change, alter how Mike thinks about product today? What makes Zuck so special on product?
• What are the biggest mistakes that Facebook made when it came to the ads product?
• What did they not do that he wishes they had done?

3. Leading Product at Deliveroo: What I Learned:

• What are Mike's biggest takeaways from his time at Deliveroo on how to make consumer products?
• What did Deliveroo do from a product perspective that worked so well? What did he learn?
• What were the single biggest product mistakes that Deliveroo made? What did he learn?
• How fast do you know when a consumer app is working or not working? When do you go against data and follow your intuition?

4. Building the Biggest Bank in Britain with Monzo:

• What are Mike's biggest lessons on product building from his time at Monzo?
• What did Monzo not do that he wishes they had done?
• Why does Mike think the US is crucial for Monzo?
• How did Monzo change how Mike thinks about competition? What do you do when your competitor, Revolut, is outshipping you at such a speed?

David Schneider is a General Partner @ Coatue and one of the great operators of the last 20 years. Prior to Coatue, David was instrumental in ServiceNow’s growth to over $100B+ public market value. David led the growth of the company from $100M to $5BN in revenue. Before joining ServiceNow, David held senior positions at Data Domain, the company he joined at $0 in revenue and scaled to $1BN in revenue and an IPO and acquisition.

In Today's Episode with David Schneider We Discuss:

1. ServiceNow: Secrets to Scaling to $5BN in ARR:

• What are David's biggest lessons from scaling ServiceNow to $5BN ARR?
• What worked? What did not work?
• What are the most common reasons companies plateau?
• How did ServiceNow roll out so many different products so effectively?
• How did David hire and ramp 180 people in 90 days?

2. From OG Operator to Newbie Investor:

• What have been the single most challenging elements of making the transition to VC?
• What advice did David get from the biggest names on entering venture?
• How long did it take David to do his first deal? What advice does he give other operators entering?
• How does doing deals in 2024 compare to when David started doing deals in 2021?

3. VC Value: Do 90% of VCs Really Damage Companies:

• Does David agree that 90% of VCs actually detract value?
• What does David mean when he says that the worst VCs are "seagull VCs"?
• What are David's biggest tips to founders on how to get the most out of their board?
• What is enough ownership for David to really give the time needed to a company?

4. Lessons from the Greats: Doug Leone, Bill McDermott, Frank Slootman:

• Doug Leone: What has David learned from Doug on what it takes to be a great investor and board member?
• Frank Slootman: What has David learned from Bill on how to be the best leader of a mega company?
• Bill McDermott: What has David learned from Frank about decision-making and execution.

Sean Rad is the Founder and former CEO of Tinder. Sean has made more romantic connections between humans than anyone in history with Tinder having matched 50BN different people. Sean is also the Founder of Rad Fund which has made over 100 investments in companies and funds.

In Today's Episode with Sean Rad We Discuss:

1. Lessons Scaling Tinder to the Fastest Consumer Social App:

• Starting: How did the idea for Tinder come to Sean in a restaurant in LA?
• Scaling: What are Sean's biggest lessons for consumer apps scaling to their first 10,000 users?
• User Acquisition: How did a party change the entire user acquisition strategy for dinner?
• What did Tinder not do that Sean wishes they had done?
• What did Tinder do that with the benefit of hindsight, they should not have done?

2. Leadership Lessons from Tinder CEOship:

• Annual Product Redesign: Why does Sean believe that every consumer company should have a complete redesign of the app every year? What are the benefits?
• Detachment: How does Sean advise founders when it comes to detaching their happiness from the performance of the company? What works? What does not work?
• Common Mistakes: What are the most common mistakes that Sean sees early-stage founders make when it comes to leadership?

3. Money, Wealth and Creating a Family Office:

• How does Sean analyse his own relationship to money? How has it changed over time?
• At what stage of wealth does Sean believe you have true financial freedom?
• What is the single best investment Sean has made? What did he learn?
• What is the worst investment he has made? What did he learn?
• What have been the single hardest and most surprising elements of creating a family office?

4. Love, Death, Marriage:

• In what ways does Sean think love has changed with time? How do we deal with the loneliness pandemic?
• What does Sean believe are the most non-obvious but important secrets to a happy marriage?
• How does Sean approach and think about his own spirituality today? Why does he not fear death?

Nick Chirls is the Founder of Asylum Ventures, a new venture firm dedicated to the creative act of building companies; treating founders like artists, not assets. Asylum raised $55 million to invest $1-2 million in early-stage founders practising the art of making startups. Prior to Asylum, Nick co-founded Notation Capital, one of NYC's most successful pre-seed firms.

In Today's Episode with Nick Chirls We Discuss:

1. Why Venture Capital is Broken Today:

• Why is VC a ponzi scheme today?
• Why are most VCs sheep and have lost all creativity?
• Why are most investors today incentivised to get dollars out of the door and not to make great investments?
• Why are services functions within VC firms total BS?
• Why do no VCs provide significant enough value to a company that it is needle-moving?

2. How to Make Money in VC in 2024:

• What are the two ways to make money at seed in 2024?
• Why do founders in unloved markets care more than those in hot markets?
• Why will large institutions lose a ton of money investing in the large firms of today?
• Why does Nick believe VCs should always sell when their founders sell shares?

3. Lessons from 3xing a Fund on One Check:

• Why does Nick think about not purchasing preferred shares and only buying common shares?
• Why does Nick believe that investing in competitive markets is stupid?
• What does Nick believe are the conditions you must accept if you are doing a $5M on $25M seed?

Zico Colter is a Professor and the Director of the Machine Learning Department at Carnegie Mellon University.  His research spans several topics in AI and machine learning, including work in AI safety and robustness, LLM security, the impact of data on models, implicit models, and more.  He also serves on the Board of OpenAI, as a Chief Expert for Bosch, and as Chief Technical Advisor to Gray Swan, a startup in the AI safety space.

In Today's Episode with Zico Colter We Discuss:

1. Model Performance: What are the Bottlenecks:

• Data: To what extent have we leveraged all available data? How can we get more value from the data that we have to improve model performance?
• Compute: Have we reached a stage of diminishing returns where more data does not lead to an increased level of performance?
• Algorithms: What are the biggest problems with current algorithms? How will they change in the next 12 months to improve model performance?

2. Sam Altman, Sequoia and Frontier Models on Data Centres:

• Sam Altman: Does Zico agree with Sam Altman's statement that "compute will be the currency of the future?" Where is he right? Where is he wrong?
• David Cahn @ Sequoia: Does Zico agree with David's statement; "we will never train a frontier model on the same data centre twice?"

3. AI Safety: What People Think They Know But Do Not:

• What are people not concerned about today which is a massive concern with AI?
• What are people concerned about which is not a true concern for the future?
• Does Zico share Arvind Narayanan's concern, "the biggest danger is not that people will believe what they see, it is that they will not believe what they see"?
• Why does Zico believe the analogy of AI to nuclear weapons is wrong and inaccurate?

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.

In Today's Episode with Scott Gorlick We Discuss:

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.

In Today's Episode with Arvind Narayanan We Discuss:

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?

Imran Khan is the OG of IPOs having taken some of the biggest companies public including Alibaba, Snap, Box, Weibo and more. Today, Imran is the founder and Chief Investment Officer of Proem Asset Management. Prior to co-founding Proem, Imran served as Snap Inc.’s Chief Strategy Officer. Under his leadership, Snap’s annual revenue run rate increased to $1.6 billion from zero in less than four years. Previously, Imran was a Managing Director and Head of Global Internet Investment Banking at Credit Suisse where he advised on more than $45 billion-worth of Internet M&A and financing transactions.

In Today's Episode with Imran Khan We Discuss:

1. The IPO Market: When Does it Open:

• How does Imran assess the state of the IPO market today?
• Can companies really go out with $100-$200M in revenue?
• Will we see revenue multiples reflate? Can venture continue as an asset class if they do not?
• When does Imran expect the IPO market to really open?

2. Is M&A F******:

• How does Imran assess the state of the M&A market today?
• How do founders need to change how they think about M&A? Why are they to blame for the lack of M&A activity we have today?
• To what extent can we blame Lina Khan for the lack of M&A?
• Why would a company go do an M&A process today when it is unlikely to be approved by the SEC?
• Why does Imran believe in the case of Wiz, it was a mistake for the company not to do the M&A?

3. AI's $600BN Question: Capex Spend:

• How does Imran analyse the insane capex spend we are seeing from Meta, Google and Amazon?
• How does Zuck not having his cash cow as the cloud business change how he can act?
• How does this compare to Google's capex spend 20 years ago? What can we learn from that?

4. Going Public: The Process, The Players and Jack Ma & Jamie Dimon:

• What is the literal process to take a company public?
• Who sets the price? What do large institutions want in companies going public?
• What are some of Imran's biggest lessons from taking Snap and Alibaba public?
• What are some of Imran's biggest lessons from Jack Ma, Jamie Dimon and Evan Spiegel?

Chad Peets is one of the greatest sales leaders and recruiters of the last 25 years. From 2018 to 2023, Chad was a Managing Director at Sutter Hill Ventures. Chad has worked with the world's best CEOs and CROs to build world-class go-to-market organizations. Chad is currently a member of the Board of Directors for Lacework and Luminary Cloud and on the boards of Clumio and Sigma Computing. He previously served as a board member for Astronomer, Transposit, and others. He was an early-stage investor at Snowflake, Sigma, Observe, Lacework, and Clumio.

In Today's Discussion with Chad Peet's We Discuss:

1. You Need a CRO Pre-Product:

• Why does Chad believe that SaaS companies need a CRO pre-product?
• Should the founder not be the right person to create the sales playbook?
• What should the founder look for in their first CRO hire?
• Does any great CRO really want to go back to an early startup and do it again?

2. What Everyone Gets Wrong in Building Sales Teams:

• Why are most sales reps not performing?
• How long does it take for sales teams to ramp? How does this change with PLG and enterprise?
• What are the benchmarks of good vs great for average sales reps?
• How do founders and VCs most often hurt their sales teams and performance?

3. How to Build a Hiring Machine:

• What are the single biggest mistakes people make when hiring sales reps and teams?
• Are sales people money motivated? How to create comp plans that incentivise and align?
• Why does Chad believe that any sales rep that does not want to be in the office, is not putting their career and development first?
• Why is it harder than ever to recruit great sales leaders today?

4. Lessons from Scaling Sales at Snowflake:

• What are the single biggest lessons of what worked from scaling Snowflake's sales team?
• What did not work? What would he do differently with the team again?
• What did Snowflake teach Chad about success and culture and how they interplay together?

Aman Narang is the Co-Founder and CEO of Toast, one of the best-in-class vertical SaaS companies of our time with a market cap today of $13.5BN. Five astonishing stats that show the quality of the Toast business today:

• $1.2bn in ARR with 48.4% from payments.

• Toast Capital has reached $1bn in annualised loans originated.

• 875k restaurants in the US (Toast has 112k: 13% market share)

• 75% of locations are coming from inbound channels

• The first investor in the company invested $500K at a $3M price

In Today's Episode with Aman Narang We Discuss:

1. The Biggest Mistakes Founders Make:

• Why does Aman believe that founders should spend more time fundraising and with investors early?
• Why does Aman believe founders should hire managers before they think they need them?
• Why does Aman believe that founders do not give up control early enough?

2. Lessons Scaling to a $14BN Market Cap:

• What did Aman and Toast do so successfully that allowed them to scale to $14BN market cap in 12 years? What worked?
• What are the single biggest mistakes Toast made that hindered their growth most?
• What are the first things to break in hyperscaling companies?
• What opportunity did Aman and Toast not take that with the benefit of hindsight, he wishes they had taken?

3. Crucible Moment Decisions: Expansion:

• How did Aman and Toast know when was the right time to release a second product?
• What has enabled Toast Capital to scale to $1BN in loans so efficiently?
• How did Aman and Toast scale so successfully into both enterprise and SMB? What are the biggest lessons from doing so? What did not work?
• How do Aman and Toast approach geographic expansion? How do they choose which countries to expand into?

Aidan Gomez is the Co-founder & CEO at Cohere, the leading AI platform for enterprise, having raised over $1BN from some of the best with their last round pricing the company at a whopping $5.5BN. Prior to Cohere, Aidan co-authored the paper “Attention is All You Need,” which introduced the groundbreaking Transformer architecture. He also collaborated with a number of AI luminaries, including Geoffrey Hinton and Jeff Dean, during his time at Google Brain, where the team focused their efforts on large-scale machine learning.

In Today's Episode with Aidan Gomez We Discuss:

1. Compute vs Data: What is the Bottleneck:

• Does Aidan believe that more compute will result in an equal increase in performance?
•  
• How much longer do we have before it becomes a case of diminishing returns?
•  
• What does Aidan mean when he says "he has changed his mind massively on the role of data"? What did he believe? How has it changed?

2. The Value of the Model:

• Given the demand for chips, the consumer need for applications, how does Aidan think about the inherent value of models today? Will any value accrue at the model layer?
• How does Aidan analyze the price dumping that OpenAI are doing? Is it a race to the bottom on price?
• Why does Aidan believe that "there is no value in last year's model"?
• Given all of this, is it possible to be an independent model provider without being owned by an incumbent who has a cloud business that acts as a cash cow for the model business?

3. Enterprise AI: It is Changing So Fast:

• What are the biggest concerns for the world's largest enterprises on adopting AI?
• Are we still in the experimental budget phase for enterprises? What is causing them to move from experimental budget to core budget today?
• Are we going to see a mass transition back from Cloud to On Prem with the largest enterprises not willing to let independent companies train with their data in the cloud?
• What does AI not do today that will be a gamechanger for the enterprise in 3-5 years?

4. The Wider World: Remote Work, Downfall of Europe and Relationships:

• Given humans spending more and more time talking to models, how does Aidan reflect on the idea of his children spending more time with models than people? Does he want that world?
• Why does Aidan believe that Europe is challenged immensely? How does the UK differ to Europe?
• Why does Aidan believe that remote work is just not nearly as productive as in person?

Laela Sturdy is Managing Partner of CapitalG, Alphabet’s $7 billion independent growth fund, where she has invested in Stripe, Duolingo (DUOL), Gusto, UiPath (PATH), Webflow and Whatnot. Laela joined CapitalG shortly after its inception in 2013 and was promoted to Managing Partner in 2023, making her one of few women to be promoted into the sole leadership role within an established multibillion-dollar venture firm. Before joining CapitalG, Laela served as Managing Director of emerging businesses at Google and held leadership roles on the YouTube and Google Search teams.

In Today's Episode with Laela Sturdy We Discuss:

1. Lessons from 10 Years Investing:

• What does Laela know now that she wishes she had known when she entered VC?
• What is the biggest miss for Laela? How did it change her mindset and approach?
• What are Laela's biggest takeaways from Stripe and UiPath? How did they change what she looks for in companies today?
• What is Laela's biggest advice to all new entrants to venture today?

2. How to Build a $100BN Company: Market Timing, Sizing and Staging:

• What does Laela mean when she says she will never take a risk on a company being able to complete a "second act"?
• How does Laela approach market sizing? How does Laela think about the notion that the best companies will always expand their markets?
• Is Laela willing to take market timing risk? What have been her biggest lessons on timing?
• Does Laela prefer founders who are new to a market and have optimistic naivety? Or prefer an expert in a market who knows every element of it?

3. The Deal: Pricing, Sizing and Upside:

• How does Laela think about price today? When is she willing to pay up vs not?
• What price did Laela pay that at the time seemed super high but turned out to be super cheap?
• What price did Laela pay that seemed super cheap but turned out to be super high?
• What upside is Laela underwriting towards? What does she need to see in base and best case?

4. VC Value Add: Is it all BS:

• Does Laela believe that the best founders really need help from their VC?
• Who is the best board member Laela works with? Why are they so good?
• What are the core areas where the VC and the founder are misaligned?
• What would Laela most like to change about the relationship that founders and VCs have?

Kaz Nejatian is Shopify’s VP of Product & Chief Operating Officer. Before Shopify, Kaz founded Kash, a payment technology company which was acquired in 2017 by one of the largest fintech companies in the U.S. Kaz then served as Product Lead for Payments and Billing at Facebook, reducing the barriers for businesses in cash-dependent markets to purchase digital ads without a credit card.

In Today's Episode with Kaz Nejatian We Discuss:

1. Learnings From the Greats:

• Mark Zuckerberg: What are Kaz's biggest lessons from working with Zuck? Why does Kaz believe Zuck is massively under-appreciated?
• Keith Rabois: What are Kaz's biggest lessons from working with Keith? How did it change how he operates on a day to day basis?
• Tobi Lütke: What have been Kaz's biggest lessons from working with Tobi? What has he changed most significantly since working with Tobi?

2. Shopify: Why We Build Our Own Tools:

• Why does Kaz believe it is crucial for Shopify to build their own tools?
• When did he doubt this strategy most? What caused him to question it?
• Why does Kaz believe the Stripe <> Shopify partnership is the most important in business?
• What is the role of a PM at Shopify?
• Why do Shopify focus on how not what product is built?

3. Eight Truths The Startup World Gets Wrong:

1. Why does Kaz believe "The Lean Startup" has done more damage than any other startup book?
2. Why does Kaz believe that 90% of companies do not know what they want when they hire?
3. Why does Kaz believe the way that companies pay their staff is totally wrong?
4. Why does Kaz believe that most companies pick fights they do not need to pick?
5. Why does Kaz believe that for 90% of companies remote work is a terrible idea?
6. Why does Kaz believe that everyone in sales and marketing should be able to code?
7. Why does Kaz believe that married people with kids are more, not less productive?
8. Why does Kaz believe that we totally misunderstand divorce rates?

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.

In Today's Episode with Shaun Maguire We Discuss:

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?

In Today's Episode with Dax Dasilva We Discuss:

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.

In Today's Discussion with Alexis Ohanian We Touch On:

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.

In Today's Episode with David Cahn We Discuss:

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. 

In Today's Episode with Ben Fiechtner We Discuss:

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. 

In Today's Episode with Ethan Mollick We Discuss:

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.

In Today's Episode with Delian Asparouhov We Discuss:

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.

In Today's Episode With Nilan Peiris We Discuss:

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.

In Our Second Episode of This Week in SaaS:

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.

In Today's Episode with Kevin Hartz We Discuss:

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?