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?

Cameron Adams is Chief Product Officer and co-founder of Canva where he is responsible for heading up the design and product teams. Since launching in 2013, Canva’s global community has grown to over 185 million monthly users in over 190 countries. In 2021, Canva was valued at $40 billion, following a $200m funding round. This saw it become one of the most valuable private software companies in the world. Prior to joining Canva, Cameron found himself working closely with Lars and Jens Rasmussen (co-founders of Google Maps) to realise the design vision for Google Wave.

In Today's Episode with Cameron Adams:

1. From Accidental Joining to Most Valuable Private Company:

• How did Cameron go from working on Google wave with Lars Rasmussen to co-founding Canva with Mel and Cliff?
• What was the single closest near-death experience in the life of Canva?
• Why did Canva fail as a social network? What did Cameron learn from that?

2. How to Create Users that Truly Love Your Products:

• What have been Canva's biggest lessons on what it takes to do world class onboarding?
• What is Cameron biggest advice to founders on how to create moments of delight in your product?
• Is simplicity always best in product? What, when made more complex, is better for the user?

3. Scaling Canva into the Enterprise:

• What are the biggest product changes that are required to move into enterprise?
• What does Cam know about moving up market that he wishes he had known when he started?
• What are the biggest product and design mistakes founders make when making the transition from PLG to enterprise sales?

4. AI Changes Everything: More Money or Better Products Only

• Who will win the foundation model layer landscape? What will it be in 10 years?
• Will companies actually make more revenue from having AI in products or will it just create better products?
• How does Canva's implementation of AI in their products impact the margins of their products?

Pedro Franceschi is the Co-Founder and CEO @ Brex, the AI-powered spend platform with tens of thousands of customers, including DoorDash, Coinbase, Robinhood and Roblox. Pedro has raised over $1.2BN for the company from the likes of Greenoaks, Ribbit, DST, Bond and YC. The latest reported valuation was $12.3BN. Before Brex, Pedro was the first person to “jailbreak” the iPhone 3G in Brazil and co-founded payments company Pagar.me with Dubugras when he was 15. In three years, Pedro scaled it to over 100 people and US$1.5 billion in transactions processed.

In Today's Episode with Pedro Franceschi We Discuss:

1. The Challenge is in Your Own Head:

• Why does Pedro believe all founders underestimate their own mental health?
• When was Pedro most anxious/depressed in the Brex journey? Why?
• What have been the single biggest needle movers for increasing his own mental health?
• How does Pedro advise other founders struggling with their own mental health?

2. From a 13-Year-Old Hacker in Brazil to Billionaire in LA:

• How did Pedro come to make $200K on the internet when he was just 12?
• Does Pedro agree that the best founders always started entrepreneurial pursuits young?
• How does Pedro reflect on his own relationship to money today? How has it changed?
• Pedro has famously taken large secondaries, how did that impact his mindset?
• How does Pedro advise other founders and VCs when it comes to secondaries?

3. The Importance of the Idea: What Everyone Misunderstands:

• What does Pedro mean when he says everyone does not appreciate enough how important the idea selection process is? How does he advise founders entering this process?
• Why does Pedro believe it is not that easy for founder to just pivot to a new idea?
• How did YC almost miss out on investing in Brex, now a $12BN company, due to the original idea?

4. Brex vs Ramp: Who Wins:

• How does Pedro feel when I say, "Ramp have gotten ahead on marketing and visibility"?
• Why does Pedro believe that "Ramp is a marketing company"? What does he mean when he says "great products will win over time"?
• Why does Pedro fundamentally disagree with Ramp's positioning of the best companies focus on saving and their giving away their software for free?
• How does this market play out over time? Winner take all or gains split across several?

Saam Motamedi is a General Partner at Greylock, where he has led investments in Abnormal Security (incubated at Greylock), Apiiro Security and Opal Security, as well as AI companies like Adept, Braintrst, Cresta, Predibase, Snorkel, and more. Before Greylock, Saam founded Guru Labs, a machine learning-driven fintech startup, and worked in product management at RelateIQ, one of the first applied AI software companies.

In Today's Conversation We Discuss:

1. Seed Today is Frothier than 2021:

• How does Saam evaluate the seed market today?
• With seed pricing being so high, how does he reflect on his own price sensitivity? When does he say too much and does not do it?
• Despite seed pricing being higher than ever before, why does Saam believe it is rational?
• How has the competition at seed changed in the last few years?

2. Series B and Growth are not a Viable Asset Class Today:

• Why does Saam believe that you cannot make money at Series B today?
• Why has pricing gone through the roof? Who is the new competition?
• When does it make sense to "play the game on the field" vs say this is BS and do something else?
• What would need to happen in the public markets for Series B to be a viable asset class again?

3. Markets vs Founders: The Billion Dollar Mistake and Lessons:

• How does Saam prioritise between founder vs market?
• What have been Saam's biggest lessons when it comes to market sizing and timing?
• What is Saam's biggest miss? How did it change his approach and company evaluation?
• Which other VC would Saam most like to swap portfolios with? Why them?

4. Saam Motamedi: AMA:

• What does Saam know now that he wishes he had known when he got into VC?
• Saam has had a meteoric rise in Greylock, what advice does Saam have for those younger investors look to really scale within a firm?
• Sourcing, selecting and servicing: Where is he best? Where is he worst?
• Why does Saam believe that most VCs do not add value?

20VC: Why We Are in a Bubble & Now is Frothier Than 2021 | Why $1M ARR is a BS Milestone for Series A | Why Seed Pricing is Rational & Large Seed Rounds Have Less Risk | Why Many AI Apps Have BS Revenue & Are Not Sustainable with Saam Motamedi @ Greylock

Mark Roberge is a Co-Founder and Managing Director at Stage 2 Capital and a Senior Lecturer at the Harvard Business School. Prior to these roles, Mark was the founding CRO at HubSpot, where he scaled ARR from $0 to $100 million and expanded his team from 1 to 450 employees. Mark was ranked #19 in Forbes' Top 30 Social Sellers in the World. He was also awarded the 2010 Salesperson of the Year at the MIT Sales Conference.

In Today's Episode with Mark Roberge We Discuss:

1. Biggest Lessons Scaling Hubspot to $100M in ARR:

• What are Mark's biggest lessons in what worked in their sales strategy in scaling to $100M in ARR?
• What elements of Hubspot's sales strategy did not work? What would he have done differently with the benefit of hindsight?
• What does Mark know now that he wishes he had known when he started at Hubspot?

2. How the Best Startups Scale into Enterprise:

• What are the single biggest mistakes startups make when scaling into enterprise?
• When is the right time? What do founders get most wrong on timing of scale into enterprise?
• What do you need to have in place both from a team and product perspective to make the transition?

3. Second Product and Second Channel:

• When is the right time to launch the second product?
• Why does Mark believe that you should be turning down customers in the early days? Why is not every customer right for your company?
• How does Mark think about channel diversification? Does Mark agree you only need one channel to scale to $50M in ARR and two to scale to $100M in ARR?

4. 99% of SaaS Founders Do Partnerships Wrong:

• What are the single biggest mistakes founders make when doing channel partnerships?
• What can and should they do to set channel partnerships up for success?
• What do the channel partners need to have to be equipped to sell the partner solution?
• What level of buy-in and from who on the channel partner side is needed for the partnership to be successful?
• What did Mark learn from Hubspot's partnership with Salesforce scaling to 10% of Hubspot's revenue?

Ara Mahdessian is the Co-Founder and CEO @ ServiceTitan, one of the great vertical SaaS business of the last decade. Today the company powers over 11,800 trade customers and has raised over $1.4BN from some of the best including Bessemer, Battery, Index, ICONIQ and more. Their latest valuation pegged the business at a reported $7.3BN.

In Today's Episode with Ara Mahdessian We Discuss:

1. We Did Not Want To Raise VC Money:

• Why did Ara not want to raise VC funding in the early days?
• What convinced Ara to change his mind? Why did he choose Byron and Bessemer?
• Does Ara believe that ServiceTitan would have been the success that it is, if it had raised in today's market, a $5M on $25M seed round? What would they have done differently?

2. How to Master Going Upmarket:

• What are Ara's biggest lessons on what it takes to go upmarket?
• How does the product need to change? How does the org of the company change?
• When is the right time to go upmarket?
• What did ServiceTitan get wrong in their move into enterprise? What did Ara learn from this?

3. How to Build a Brand in SaaS and Have Premium Pricing:

• What are some of Ara's biggest lessons in how to build the best brand in vertical SaaS?
• What works in brand building in SaaS? What does not? What would he do differently?
• What have been Ara's biggest lessons on pricing? ServiceTitan is 3x their competitors, how does Ara think about what is required to have such premium pricing?

4. How to Master the Second Product & Be the Best at Customer Success:

• When is the right time to do a second product? Why is it too late to wait for PMF with your first product to do the second product?
• What product did ServiceTitan wait too long to release? What did they learn?
• What product did they release too early? What did they learn?
• What are the two core reasons why customer success is the most important element in a business?

5. The Core Pillars of Great Leadership:

• Why do product builder founders have such an increased chance of success in startups?
• Why do you have to have expertise in the domain you are hiring for to hire the best?
• What does truly great leadership mean to Ara today? How has his style of leadership changed?
• What has Ara learned from soccer that he has applied to being a CEO?

Pat Grady is one of the most successful growth investors of the last decade. As the Head of Sequoia's growth investing practice, Pat has invested in companies with a combined market cap exceeding $250BN. Among Pat's immense portfolio is Hubspot, Snowflake, ServiceNow, Okta, Amplitude, Zoom and Qualtrics. Pat is also one of the best acquirers of talent in venture hiring Andrew Reed, Matt Huang, Julien Bek.

In Today's Episode with Pat Grady We Discuss:

1. The Sequoia Investment Process:

• What is the Sequoia investment process today? How has it changed over time?
• What could be improved about the process? Where is it weak?
• What is the biggest strength of the process?
• How do Sequoia remove politics from the investment decision-making process?
• Are the best deals "contrarian"? What does Pat mean when he says you do not "get extra points for being contrarian and right"?

2. What Sequoia Look for When Investing:

• What is Pat's framework for assessing founders? How does it differ when investing early vs late?
• Team, traction, TAM, how does Pat rank the three when investing?
• What have been Pat's biggest lessons on market sizing? Does Pat take market timing risk?
• How much weight does Pat place on "traction" when investing? How sustainable is PMF?

3. The Three Core Pillars of Venture:

• Sourcing: What does Pat rank Sequoia for sourcing? Who is the best at sourcing in the firm?
• Selecting: How does Pat rank Sequoia at picking? How has it changed over time? What could Sequoia do to improve their picking ability?
• Servicing: What does Pat give Sequoia for their "value add"? To what extent does Pat truly believe that venture investors do add value?

4. Pat Grady: AMA:

• Pat has hired some of the best in the next generation of venture investors; what are his biggest lessons in what he looks for when hiring investing talent?
• What is his single biggest takeaway from working with Alfred Lin, Roelof Botha and Doug Leone?
• What are his biggest takeaways from working with Hubspot, Snowflake and ServiceNow?

Avi Eyal is Co-Founder and Managing Partner of Entrée Capital, an early-stage VC fund with a portfolio including the likes of Monday.com, Stripe, Coupang, PillPack, and Snap. From their $15M investment into Monday, Entrée distributed a whopping $1.5BN, one of their $45M funds is a whopping 37x DPI. Avi is one of the greatest venture investors you might not have heard about.

In Today's Episode with Avi Eyal We Discuss:

1. The Biggest BS "Rules" in Venture Capital:

• Why does Avi believe that it is BS for every deal to need to be a homerun and return the fund?
• Why does Avi believe that signalling is real and it is BS to suggest otherwise?
• Why does Avi believe that it is BS that ownership is crucial to make mega venture returns?
• Why does Avi believe that you do not have to win every deal to be one of the best in venture?
• Why should venture investors not manage the positions of their companies when they go public? Why is it BS to think they have asymmetric information when the company goes public?

2. What Makes the Best Founders:

• Does Avi prefer first or second time entrepreneurs? Why?
• Would Avi rather back a founder that is an expert in a market or one that is new to a market and has the naivety to not know what is hard?
• Are the best CEOs the best fundraisers?
• How does Avi rank the following when investing; team, market, traction and technology?
• When Avi has misread a founder, what was it that he missed?

3. The Biggest Hits and Biggest Misses:

• Monday: How did Entrée build such a large position in Monday over time? How did a Series A lead dropping out leading to a $1.5BN gain for Entree?
• Stripe: Entrée has now 50% of his Stripe position. Why? What is the three step process for Avi in selling positions? How does he know when to and what is the right amount?
• PillPack: Entrée made $15M from PillPack's exit. What did that teach Avi about ownership?
• Cazoo: How was Entrée the only one to make money from Cazoo? How did Entrée's sell strategy help him make millions when everyone else did not sell?

Matt Clifford is the Co-Founder of Entrepreneur First (EF), the leading global talent investor and incubator. EF has incubated startups worth over $10bn, including Cleo, Tractable and Aztec Protocol. Matt is also Chair of ARIA, the UK’s Advanced Research and Invention Agency, and advises the UK government on AI and in 2023 served as the Prime Minister’s Representative for the AI Safety Summit at Bletchley Park.

In Today's Episode with Matt Clifford We Discuss:

1. The Most Important Questions in AI:

• Are we seeing diminishing returns where more compute does not lead to a significant increase in performance?
• What is required to reach a new S curve? What do we need to see in GPT 5?
• Why does Matt believe that search is one of the biggest opportunities in AI today?

2. The Biggest Opportunities in AI Today:

• How does Matt see the future for society with a world of autonomous agents?
• What is the single biggest opportunity around agents that no one has solved?
• Is society ready for agentic behaviours to replace the core of human labour?
• How does warfare change in a world of AI?
• Does AI favour states and good actors or criminals and bad actors more favourably when it comes to offence and defence?

3. China and the Race to Win the AI War:

• Does Matt believe that China are two years behind the US in terms of AI capability?
• What are Matt's biggest lessons from spending time with the CPP in China working on AI policy?
• In what way is the CCP more sophisticated in their thinking on AI than people think?
• What is the bull and the bear case for China in the race for AI?
• What is the core impact of US export controls on chips for China's ability to build in AI?
• Does a Trump vs a Biden election change the playing field with China?

4. What Makes Truly Great Founders:

• Does Matt agree that the best founders always start an entrepreneurial activity when they are young?
• What is more important the biggest strength of one of the founders or the combined skills of the founding team?
• What did EF believe about founders and founder chemistry that they no longer believe?
• Does Matt believe that everyone can be a founder? What are the two core traits required?

Samir Vasavada is the Co-Founder & CEO of Vise, a technology-powered asset manager. Samir and his co-founder, Runik founded Vise from the Midwest at 16 years old. They bootstrapped the company before dropping out of high school and raising $128M in just 6 months from some of the best including Sequoia Capital and Founders Fund. The company achieved unicorn status when the pair turned 20 years old, making them the youngest founders of a $BN company at the time.

In Today's Episode with Samir Vasavada We Discuss:

1. The Biggest Hiring Mistakes That Broke Us:

• Why is hiring people who come with a playbook one of the most damaging things you can do?
• Why is it impossible to build a remote company that performs the same as in person?
• Why is it the worst thing to hire people who have a reputation they are obsessed with maintaining?
• Why do you never want to hire people who join because of who your investors are?
• Why does Samir regret not firing people faster? How much time is enough time to know?
• Why is hiring in a hot market one of the most dangerous things you can do?

2. Fundraising: 3 Rounds and $126M in 6 Months:

• Does Samir regret raising so much money so soon in the company life?
• What did Samir do that he regrets doing, having had so much money so early?
• How did the need for free food at an event lead to a term sheet and $50M from Sequoia?
• Did Samir feel that he could talk to investors when things were going really badly?
• Why does Samir believe that liquidation preference matters more than valuation?

3. The Depression, The Pressure and Wisdom From Jensen Huang:

• What did Jensen Huang teach Samir when it comes to wealth and leadership?
• How did Samir deal with the pressure of raising $126M in 6 months and being the youngest unicorn founder, ever at the time?
• Was Samir hurt when people he thought were his friends, no longer stuck with him when the company was no longer "hot"?
• What was Samir's darkest time? How did he overcome and get out of it?
• Does Samir blame his parents for the pressure they put on him from such a young age?

Andrew Bialecki is the Co-Founder and CEO of Klaviyo, the platform that powers smarter digital relationships for businesses and their data. To date, Klaviyo has raised over $778M from the likes of Accel, Summit Partners, Sands Capital, and Shopify, and raised an additional $700M after its IPO in September 2023. 

In Today’s Episode with Andrew Bialecki We Discuss:

1. Founding a $6.23BN Machine in Klaviyo: The Aha Moment

• What was the aha moment for Klaviyo?

• How important does Andrew think it is for founders to stick with their initial vision vs when is the right time to pivot?

• Does a great product sell itself? If you build it, will they come?

2. Bootstrapping Klaviyo: Would it Have Worked with More VC Cash Earlier?

• Why did Andrew decide to bootstrap & not take VC money with Klaviyo?

• Does Andrew think Klaviyo would have been successful if they raised a seed round? What would they have done differently?

• Why does Andrew believe companies should take their time to find product-market fit? What are the most common mistakes founders make?

• What is Andrew’s advice to founders on fundraising?

• When did Andrew decide to raise a seed round when he did? 

3. How to IPO in an IPO Winter: Advice & Lessons

• Why did Andrew decide to take Klaviyo public in a bad public market?

• How was the IPO roadshow process? What were Andrew’s lessons from it?

• How has Andrew’s role as CEO changed after taking Klaviyo public?

• Does Andrew think Klaviyo is undervalued today?

• What is Andrew’s advice to founders on secondaries?

4. Behind the Shopify Partnership

• How did Klaviyo’s partnership with Shopify happen? What were Andrew’s lessons working with Tobi Lütke & Harley Finklestein?

• How does Andrew define a win-win partnership? 

• What does Andrew mean by “Partnerships are like a tug of war?”

• What does Andrew think are the most common reasons partnerships go sideways?

David Luan is the CEO and Co-Founder at Adept, a company building AI agents for knowledge workers. To date, David has raised over $400M for the company from Greylock, Andrej Karpathy, Scott Belsky, Nvidia, ServiceNow and WorkDay. Previously, he was VP of Engineering at OpenAI, overseeing research on language, supercomputing, RL, safety, and policy and where his teams shipped GPT, CLIP, and DALL-E. He led Google's giant model efforts as a co-lead of Google Brain.

In Today's Episode with David Luan We Discuss:

1. The Biggest Lessons from OpenAI and Google Brain:

• What did OpenAI realise that no one else did that allowed them to steal the show with ChatGPT?
• Why did it take 6 years post the introduction of transformers for ChatGPT to be released?
• What are 1-2 of David's biggest lessons from his time leading teams at OpenAI and Google Brain?

2. Foundation Models: The Hard Truths:

• Why does David strongly disagree that the performance of foundation models is at a stage of diminishing returns?
• Why does David believe there will only be 5-7 foundation model providers? What will separate those who win vs those who do not?
• Does David believe we are seeing the commoditization of foundation models?
• How and when will we solve core problems of both reasoning and memory for foundation models?

3. Bunding vs Unbundling: Why Chips Are Coming for Models:

• Why does David believe that Jensen and Nvidia have to move into the model layer to sustain their competitive advantage?
• Why does David believe that the largest model providers have to make their own chips to make their business model sustainable?
• What does David believe is the future of the chip and infrastructure layer?

4. The Application Layer: Why Everyone Will Have an Agent:

• What is the difference between traditional RPA vs agents?
• Why is agents a 1,000x larger business than RPA?
• In a world where everyone has an agent, what does the future of work look like?
• Why does David disagree with the notion of "selling the work" and not the tool?
• What is the business model for the next generation of application layer AI companies?

Val Scholz is the former Head of Growth @ Revolut, where he led the company to their first 10M users. Post Revolut, Val played a crucial role in scaling several high-growth companies including VEED, Simple & Busuu (exited for $400M). Today, Val is the Head of Growth at Kittl, an intuitive design platform empowering graphic designers.

In Today’s Episode with Val Scholz We Discuss:

1. Lessons from Scaling Revolut to 10M Users

• What were Val’s biggest takeaways during his time at Revolut?

• What does Val consider the secret sauce behind Revolut’s success?

• What did Val think Revolut understood about customers that no other bank did?

2. The Secrets to Revolut’s Growth Playbook

• What was Val’s best growth decision? What was his worst?

• Why does Val think most companies don’t do referrals well?

• What made Revolut’s signup strategy so successful?

• What are Val’s two ways to master content marketing?

• Does Val think it’s good to diversify growth channels? When should founders diversify?

• What are Val’s strategies to make Youtube influencers successful?

3. Product Marketing 101:

• Why does Val think traditional marketing methods are outdated?

• If traditional marketing methods are outdated, what should startups do instead?

• What does Val think is the most dangerous myth around product-led growth?

• What does Val believe are the most common mistakes founders make on optimizing products?
  

4. Growth Hires: Who, What, When & How

• When does Val think is the best time to hire a head of growth?

• What is the profile Val looks for in a growth hire? What traits does he look for?

• What are the most common reasons founders fail at hiring?

• What does Val think are the biggest red flags to look out for in a CV?

• How does Val define good culture? Did Revolut have a good culture?

Michael Eisenberg is a Co-Founder and General Partner @ Aleph, one of Israel's leading venture firms with a portfolio including the likes of Wix, Lemonade, Empathy, Honeybook and more. Before leading Aleph, Michael was a General Partner @ Benchmark.

In Today's Show with Michael Eisenberg We Discuss:

1. The State of AI Investing:

• Why does Michael believe that "foundation models are the fastest depreciating asset in history"?
• Are we in an AI bubble today? As an investor, what is the right way to approach this market?
• Who will be the biggest losers in this AI investing phase?
• Where will the biggest value accrual be? What lessons does Michael have from the dot com for this?

2. Where Is the Liquidity Coming From?

• Why does Michael believe that it is BS that private equity will come in and buy a load of software companies and be the primary exit destination?
• Why does Michael believe that IPO windows are always open? Should founders go out now? What is good enough revenue numbers to go out into the public markets?
• Why does Michael believe that Lina Kahn is a threat to capitalism? How does Michael predict the next 12-24 months for the M&A market?

3. AI as a Weapon: Who Wins: China or the US:

• Does Michael agree with the notion that China is 2 years behind the US in AI development?
• Does Michael agree that AI could be a more dangerous weapon in wars than nuclear weapons?
• Why does Michael suggest that for all founders in Europe, they should leave?
• US, China, Israel, Europe, how do they rank for innovating around data regulation for AI?

4. Venture 101: Reserves, Selling Positions and Fund Dying:

• Why does Michael only want to do reserves into his middle-performing companies?
• What framework does Michael use to determine whether he should sell a position?
• Which funds will be the first to die in this next wave of venture?
• Why does Michael not do sourcing anymore? Where is he weakest in venture?
• Why does Michael believe that no board meeting needs to be over 45 mins?

Danny Rimer is a Partner @ Index Ventures and one of the most prominent VCs of the last two decades. Danny has led Index to be one of the top global firms on both sides of the Atlantic. Among Danny's incredible portfolio, he has led or been involved with Figma, Discord, Dream Games, Etsy, Glossier and Patreon.

In Today's Discussion with Danny Rimer We Cover:

1. The Biggest Lessons from Missing Snap, Airbnb, Spotify and Facebook:

• How did Danny miss investing in Brian Chesky and Airbnb when Brian says "Index is the best investor that Airbnb never had"?
• What was Danny's biggest takeaway from turning down Daniel Ek and Spotify multiple times?
• Why did Danny turn down the chance to invest in Facebook at $10BN? What did he learn from this?
• Why did Index not lead Snapchat's Series B? How did that decision change Danny's mindset towards the concentration of positions in a fund?

2. The Biggest BS Rules in Venture: Market Sizing, Valuations and Signalling

• Why does Danny believe that "valuation is a mental trap"?
• Why does Danny believe that TAM is "noise" and should not be used to assess an investment?
• Why does Danny believe that stage, sector and geo-specific funds are BS?
• Why does Danny believe there are no IPO windows? Are IPO markets always open to the best?
• Why does Danny believe that signalling is BS and does not exist today?

3. Lessons from the Biggest Wins and Losses:

• What are Danny's biggest lessons from Index's $BN win in King (Candy Crush)?
• How did the Discord deal come to be? What are Danny's biggest takeaways from it?
• What are Danny's biggest reflections from losing 10s of millions on Nasty Gal?
• What is Danny's biggest advice to a new investor today?

4. Lessons from Two Decades Building Index into a Premier Firm:

• What specifically has Index done to enable them to do what no one else has done and win on both sides of the Atlantic?
• How did the Benchmark partnership shape much of how Danny has constructed Index today?
• Who does Danny view as Index's biggest competition? How has it changed with time?
• Why is Danny more bullish than ever on the UK despite Brexit?

Janie Lee is the Head of Product and the owner of the Self-Serve business at Loom. Janie previously worked at Rippling, leading the Identity Management and Hardware teams. Prior to that, she worked at Opendoor launching markets and developing pricing algorithms. During this time, Opendoor scaled from 2 to 20+ markets, $5B+ revenue, and 1500+ employees.

In Today's Episode with Janie Lee We Discuss:

1. Inside the Product Building Machine of Rippling and Opendoor:

• What are Janie's single biggest product lessons from Rippling? How do they build so much product so fast? Can you have breadth and high quality?
• What are Janie's biggest lessons from Opendoor on talent and pricing?
• What does Janie know now that she wishes she had known when she started her product career?

2. What Makes a Truly Great PM:

• What core skills do the best PMs have? What is the difference between good vs great?
• Writing: What are Janie's biggest pieces of advice to PMs who want to write better?
• Communicate: How do the best PMs and product leaders communicate with their teams?
• Question Asking: How do the best PMs ask questions of their team and other orgs?

3. How to Find and Pick the Best PMs:

• How does Janie structure the interview process when hiring new PMs?
• What questions should one ask in every interview with a PM?
• Does Janie do a case study? What is she looking to achieve from it? How do the best do?
• What are Janie's biggest mistakes in hiring PMs? How did she change from it?

4. Onboarding PMs and Crushing Product Reviews:

• What do the first 30 days look like for new PMs?
• What are the biggest signs that a new PM is not going to work out?
• How does the product review process work at Loom?
• How does Janie prioritise when there is so much volume and data?
• How has AI changed the way Loom builds products today?