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?