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

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.
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Jul 19, 2024

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?

 

Jul 17, 2024

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?

 

Jul 15, 2024

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

Jul 12, 2024

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?

 

Jul 10, 2024

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?

 

Jul 8, 2024

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?

 

Jul 3, 2024

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?

 

Jul 1, 2024

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?

 

Jun 28, 2024

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?

 

Jun 26, 2024

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?

  1. 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? 

  1. 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?

  1. 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?

 

 

 

Jun 24, 2024

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?

 

Jun 21, 2024

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?

  1. 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?

  1. 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?

  1. 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?

 

Jun 19, 2024

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?

 

 

Jun 17, 2024

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?

 

Jun 14, 2024

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?

 

Jun 12, 2024

Alex Wang is the Founder and CEO @ Scale.ai, the company that allows you to make the best models with the best data. To date, Alex has raised $1.6BN for the company with a last reported valuation of $14BN earlier this year. Scale tripled their ARR in 2023 and is expected to hit $1.4BN in ARR by the end of 2024. Their investors include Accel, Index, Thrive, Founders Fund, Meta and Nvidia to name a few.

In Today's Show with Alex Wang We Discuss:

1. Foundation Models: Diminishing Returns:

  • What are the three core pillars that can meaningfully improve foundation models performance?
  • Why is data the single largest bottleneck to the performance of models today?
  • What data do we need to capture that we do not currently, that will have the biggest impact on model performance moving forward?
  • Will we see the largest companies in the world revert back to on-prem with the increasing security challenges of migrating all customer data to foundation models?

2. AI: A Military Asset in Global Conflict: China + Russia

  • Why does Alex believe that AI has the potential to be an even more powerful military asset than nuclear weapons?
  • If this is the case, should we have open systems? Do we not have to have closed systems?
  • Why does Alex believe that the CCP's approach to industrial policy is better than anyone else's?
  • How does Alex evaluate the rise of Chinese EV car manufacturers in the last few years?
  • Does Alex really believe that China is two years behind the US in the AI race?

3. "I Get Fairer Treatment in Congress than in the Press":

  • Why does Alex believe that the best PR is no PR?
  • Why does Alex believe that he got fairer treatment in congress than he does in the media?
  • Why does Alex believe that all founders should look to own their own distribution channels today?

4. Alex Wang: AMA:

  • What are some of Alex's biggest lessons from Patrick Collison on the impact that a hot company brand has on the ability for that company to hire the best?
  • Does Alex think Trump is going to win? What would be the impact if he were to?
  • Why does Alex believe that enterprise software will be changed forever in the next few years?
  • What question is Alex never asked that he thinks he should be asked?

 

Jun 10, 2024

Reid Hoffman has been one of the most impactful people in technology over the last two decades. He is the Co-Founder of Linkedin (acq by Microsoft for $26BN) and Co-Founder of Inflection.ai. As an investor, Reid has backed the likes of Facebook, Airbnb, Zynga and more. Reid is also a Board Member @ Microsoft and was on the board of OpenAI.

In Today's Show with Reid Hoffman We Discuss:

1. Foundation Models: Commoditisation, Business Models, Incumbents:

  • Does Reid believe we are seeing the commoditization of foundation models?
  • Is it too late for new foundation models to be born today? Are they VC backable?
  • How will foundation models eventually make money? What will be the sustainable business model?
  • Does Reid believe that foundation models will be acquired by large cloud providers? Who goes first?

2. Inflection & Microsoft: What Went Down:

  • How did the Microsoft and Inflection deal go down? Did Satya call up one day and make it happen?
  • With the decay rate of models, Microsoft did not do it for the models, so why did they do it?
  • Was Inflection a sustainable business in it's own right?
  • Does this not prove that to win at this game, you have to be an incumbent with incumbent cash?

3. OpenAI: Board, Lessons and Management:

  • What are 1-2 of Reid's biggest lessons from being on the OpenAI board with Sam?
  • Why did Sam ask Reid in front of the whole company if Reid would fire him if he did not perform?
  • Scarlett Johannsen, super alignment team quitting, NDAs tied to equity, this is a lot in a short amount of time, how does Reid analyse this?

4. Trump is the Biggest Threat to Democracy: What Lies Ahead?

  • Why does Reid believe that Trump is a threat to democracy and evil?
  • What were Reid's biggest takeaways from a two hour lunch with Joe Biden?
  • How does a Trump administration change the world of AI, technology and startups?

5. The Future of TikTok:

  • Is TikTok a threat to US democracy? Should it be banned?
  • What will be the outcome of the current judicial process? Will they sell to a US entity?
  • How could Trump impact the future of TikTok in the US?

6. Reid Hoffman: AMA:

  • What are Peter Thiel's biggest strengths and weaknesses?
  • I believe Mark Zuckerberg is one of the most unappreciated public market CEOs, what are the core components that Reid believes makes Mark so special?
  • How did Reid miss out on investing in SpaceX's first round? What did he not see that he should have seen?
  • What do we think is crazy today but will be a no brainer and very normal in 10 years?

 

Jun 7, 2024

Ashley Kelly is the VP of Global Sales Development at Rippling, the all-in-one platform for HR, IT, and finance. Before Rippling, Ashley played a crucial role in scaling Brex’s outbound sales from $2M to over $300M in ARR, and has hired over 800 SDRs during her time in some of the best tech companies in Silicon Valley, including Lever and Zenefits. 

In Today’s Episode with Ashley Kelly We Discuss:

  1. From NASCAR to Silicon Valley SDR

  • How did Ashley make her way into the world of sales?

  • Why does Ashley think the best AEs and leaders start off as SDRs?

  • What is Ashley’s advice to new SDRs starting their jobs today?

  1. Age of AI: Is SDR Outbound Dead?

  • Does Ashley agree that outbound is dead today? Is SDR dead?

  • How will AI change SDR? Why is Ashley hesitant to adopt AI?

  • Why does Ashley think founders should always build the first sales playbook?

  • What did Ashley mean by SDR is the 3rd pillar between sales and marketing? 

  • What does Ashley think most companies get wrong about outbound?

  1. SDR Hiring: Who, What, When & How

  • When does Ashley think founders should hire their first SDR?

  • How does Ashley structure the hiring process? What questions does she ask?

  • What profile does Ashley look for when hiring for an SDR?

  • How does Ashley structure the finance package? How is it different for each team?

  • Why did Ashley avoid hiring SDRs with SDR experience? Why has she changed her mind?

  • What was Ashley’s biggest hiring mistake? What were her takeaways?

  1. Onboarding New SDR Hires

  • How does Ashley onboard new SDR hires? What is her onboarding timeline?

  • How does Ashley set targets for new hires? When should they be fully productive? 

  • When does Ashley know if a new hire isn’t working?

  • What are common traits among Ashley’s most successful hires?



Jun 5, 2024

Aravind Srinivas is the Co-Founder & CEO of Perplexity, the conversational "answer engine" that provides precise, user-focused answers to queries. Aravind co-founded the company in 2022 after working as a research scientist at OpenAI, Google, and DeepMind. To date, Perplexity has raised over $100 million from investors including Jeff Bezos, Nat Friedman, Elad Gil, and Susan Wojciki.

In Today’s Episode with Aravind Srinivas We Discuss:

  1. Biggest Lessons from DeepMind & OpenAI

  • What was the best career advice Sam Altman @ OpenAI gave Aravind?

  • What were Aravind’s biggest takeaways at DeepMind?

  • How did DeepMind shape how Aravind built Perplexity?

  • What did Aravind mean by “competition is for losers?” What did he learn about talent assembly at DeepMind?

  1. The Next AI Breakthrough: Reasoning

  • Does Aravind think we are experiencing diminishing returns on compute & model performance?

  • Does Aravind agree reasoning will be the next big breakthrough for models?

  • What are the reasons Aravind thinks models suck at reasoning today?

  • What is the timeline for reasoning improvement according to Aravind?

  • What does Aravind think are the biggest misconceptions about AI today?

  1. Will Foundation Models Commoditise?

  • Does Aravind think foundation models will commoditise? What will the end state of foundation models look like?

  • Why does Aravind think the second tier models will get commoditised?

  • Why does Aravind think the subscription model will not work for AI models with true reasoning? 

  • Why does Aravind think the application layer companies will benefit from foundation models commoditising?

  • Why does Aravind think foundation models will not verticalize?

  • When does Aravind think is the right time to go enterprise? What is his strategy to differentiate Perplexity from its competitors?

  1. AI Arms Race: Who Will Win?

  • Who does Aravind think will be the winners of foundation models?

  • What do AI companies need to do to win the model arms race?

  • How does Aravind think startups can compete against incumbents' infinite cash flow?

  • What are the reasons Aravind thinks Perplexity’s browsing is better than ChatGPT?

  • What is Aravind’s biggest challenge at Perplexity today?

 

 

Jun 3, 2024

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 First Ever Episode of This Week in SaaS

1. PluralSight Goes to Zero:

  • WTF happened to PluralSight? How did it go from $3.5BN to $0?
  • Will this have a wider impact on the willingness of PE to buy tech companies?
  • Who are the next contenders to go from hero to zero? Zendesk? Anaplan?
  • Will this generation of PE funds be let off by their LPs for a poor vintage?

2. Salesforce's Worst Stock Market Drop Since 2004 + Mongo Takes a 23% Hit:

  • Why did Salesforce lose $50BN of market cap in a single day?
  • Is the same true for MongoDB taking a 23% hit in one day?
  • What does it mean when the new normal is these once hyper-growth companies now growing only 6% per annum?

3. The Settlers into Slow Growth:

  • Why does Jason believe that Dropbox and Box have both settled into a world of slow growth?
  • What happens to Twilio from here in a world post Jeff Lawson?
  • What happens to Retool from this point on?
  • Would Jason be a buyer of Notion at $10BN?

4. Venture Capital is Broken:

  • Why does Jason believe that we need to see a relation of public multiples for the math in venture capital to work again?
  • Why does Jason believe that the way we mark portfolios with TVPI leads to corrupt and bad behaviour?
  • How does Jason think we will solve the problem of liquidity with IPOs being shut, M&A being out of the window and now PE being a doubt as the source of buyers?

May 31, 2024

Matt Lerner is one of the OGs of growth having spent 11 years leading growth teams at PayPal. Post PayPal, Matt led the growth marketing program at 500 Startups. He is also the bestselling author of Growth Levers and How to Find Them. Today, Matt is the Co-Founder and CEO of SYSTM, an accelerator program helping startups find their growth drivers. 

In Today’s Episode with Matt Lerner We Discuss:

  1. From Philosophy Student to PayPal Growth Leader:

  • How did Matt make his way into the world of growth?

  • What were Matt’s biggest lessons from 11 years at PayPal?

  • What did Matt know now that he wished he’d known when he entered the world of growth?

  1. How to Master Growth in a World of AI:

  • What is growth to Matt? What is it not?

  • Why does Matt think growth is more science than art?

  • Does Matt Agee with Adam Gross @ Vimeo that paid acquisition below $100M ARR isn’t PLG?

  • How does Matt think AI will change the world of growth today?

  • What does Matt think are the most common growth mistakes founders make?

  1. Optimizing Growth Channels: Dos & Don’ts

  • Why does Matt believe there are only six types of growth channels?

  • What is the “locksmith moment" & how do startups find channels that work for them?

  • How does Matt pick a Northstar metric? 

  • What are the most common mistakes founders make when picking North Star metrics? When is the right time to change them?

  • How does Matt approach horizontal product messaging? What works? What doesn’t work?

  1. How to Hire & Manage Growth Teams

  • What does Matt look for in the first head of growth hire?

  • What questions does Matt ask when interviewing?

  • What were Matt’s biggest hiring mistakes? What did he learn?

  • Why does Matt think the best growth hires have no marketing experience?

  • What are Matt’s two steps to master onboarding?

  • What are the 3 most common patterns in leaders according to Matt?

 

May 29, 2024

Mike Schroepfer (Schrep) is the Founder & Partner @ Gigascale Capital, a new kind of climate-focused investment firm. Prior to Gigascale, Mike was the CTO @ Meta where he scaled products to billions of users, shipped millions of units of consumer hardware, constructed tens of millions of sq ft of data centres, built teams of up to 35,000, and made breakthroughs in AI. Before Meta, Mike led engineering at Mozilla and founded a company acquired by Sun Microsystems.

In Today's Show with Mike Schroepfer We Discuss:

1. Lessons from Mark Zuckerberg and Meta:

  • What are Schrep's biggest lessons from Zuck on truly effective leaders?
  • Why does Schrep believe the best leaders are like music conductors?
  • What does Schrep mean when he says, "building a company is a game of inches"?
  • Why does Schrep believe "inertia is one of the most underappreciated forces in company building?"

2. The Future of Energy:

  • Why does Schrep believe that the "availability of cheap, clean energy is the biggest rate limiter to human progress?"
  • Does Schrep agree with Sam Altman that energy will be the currency of the next decade? Or does he believe Mustafa Suleyman is right and it will soon be free and abundant?
  • How does Schrep predict the next five years for both fusion and nuclear?
  • Why does Schrep believe the next few years will be "messy but with huge opportunity"?

3. Investing in Climate: It has to be Profitable:

  • Why does Schrep believe that markets and not governments or philanthropy will solve the climate challenges we face?
  • What leads Schrep to suggest that the climate change transition is a $10TRN opportunity for investors?
  • What is the single hardest element of investing in climate change solutions today?
  • Why do climate change solutions need to reshape how they market to consumers?
  • How much capital does it take to build a defensible moat in climate?

4. Schrep: The Man Behind Whatsapp and Instagram: AMA:

  • How does Schrep reflect on his own relationship to money? How has it changed?
  • How does Schrep think about what it takes to be a great father?
  • How did Schrep manage the physical stress and pressure of managing engineering for products that serve billions of people in WhatsApp and Instagram?

 

 

May 27, 2024

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 Today's Episode with Jason Lemkin We Discuss:

1. Growth Rates and Churn Rates: Average/Good/Great:

  • What is a growth rate that would excite Jason in a SaaS company? What is average?
  • What levels of churn would worry Jason to see? What would excite him to see?
  • What does Jason never tolerate when it comes to either growth rate or retention?

2. What Founder Combination Always Wins:

  • Why does Jason believe you cannot lose money on a CEO salesperson and a technical CTO founding partnership?
  • Why does Jason always meet the CTO for a second meeting in the diligence process? What questions does he ask? What do the best CTOs do or say?
  • Why does Jason always want to sell his shares when the founders want to sell?
  • Why does Jason believe that a company is never the same when the founders leave?

3. WTF is Happening in the World of VC:

  • Why does Jason believe that pricing is worse than it has ever been in venture?
  • Why does Jason believe that traditional seed VC is systemically broken?
  • Why are companies getting stuffed with more cash than ever before?
  • What does Jason know now about dilution that he wishes he had known when he started?
  • Why does Jason believe that you should always recycle everything?

4. WTF is Happening in PE and Later Stage Markets:

  • What happens to all the overpriced acquisitions like Zendesk and Salesloft where private equity way overpaid for them, they have no growth and no product innovation?
  • What happens to the generation of public companies like Box, Dropbox and Twilio, all with low growth and little product innovation in the single-digit market caps?
  • Why does Jason believe that Klaviyo is the most undervalued public company today?
  • What does Jason believe will happen to Anaplan with Pigment eating their lunch?

May 24, 2024

Sam Altman is the CEO @ OpenAI, the company on a mission is to ensure that artificial general intelligence benefits all of humanity. OpenAI is one of the fastest-scaling companies in history with a valuation of $90BN and $2BN+ in revenue.

Brad Lightcap is the COO @ OpenAI and the man responsible for the incredible scaling of sales, GTM, partnerships and business to today being over $2BN in revenue.

Arthur Mensch is the Co-Founder and CEO of Mistral AI. Since its inception in May 2023, Mistral has raised over $520M in funding from investors like Andreeseen Horowitz, General Catalyst, Lightspeed Venture Partners, and Microsoft with a current valuation of $2 billion. 

Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support. Today Des leads all of Intercom’s R&D efforts, and parts of Intercom’s marketing.

Tom Hulme is a Managing Partner of GV (Google Ventures), and leads the European team. Today, GV has over $10BN in AUM and Tom has led investments in Lemonade.com (IPO), Snyk, Secret Escapes, Blockchain.com, GoCardless, and Currency Cloud (exited to Visa).

Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, just announced last week, Theory is a $230M fund that invests $1-25m in early-stage companies that leverage technology discontinuities into go-to-market advantages.

Sarah Tavel is a General Partner @ Benchmark, one of the most successful and renowned venture firms in the world. At Benchmark, Sarah has led rounds in Chainalysis, Hipcamp, Medely, Rekki, Glide, Cambly and more.

In Today's Episode We Discuss:

  1. Will foundation models be commoditised?
  2. What is the end state for the foundation model landscape in 10 years?
  3. How will large cloud provider incumbents approach M&A with smaller foundation model providers?
  4. When will we see marginal revenue exceed marginal cost in the foundation model business model?
  5. Where is the value: the application layer or the infrastructure layer?
  6. How can startups know whether they will be threatened by OpenAI?
  7. What are good tests/questions to know if you are in the path of one of the large foundation models?
  8. How does the business model of SaaS fundamentally change in a world of AI?
  9. Will we see the end of per-seat pricing in a new world of AI?
  10. What is the right way to approach pricing in a world of AI? Consumption? Tokens?

 

May 22, 2024

Aaron Levie is one of the OG founders of the last two decades as the Co-Founder and CEO of Box. Today, Box does over $1BN in revenue with a market cap of $3.85BN, and has raised over $560 million from the likes of DFJ, Andreesen Horowitz, and Coatue. 

In Today’s Episode with Aaron Levie We Discuss:

  1. What You Need to Know Entering This AI Wave:

  • Why does Aaron think we are currently in a transformative window in AI?

  • What does Aaron think it takes to be successful in this next wave?

  • Which areas does Aaron think founders should be focusing on today? Where should they not?

  1. AI Adoption: Business Model, Implementation, Regulation.

  • How does Aaron think AI will change how we work & run a business?

  • What does Aaron think is the single biggest obstacle to AI adoption in large organizations?

  • Does Aaron agree with Sarah Tavel @ Benchmark AI companies will be selling work not tools? 

  • How does Aaron think AI will change the SaaS business model?

  • Why is Aaron not as worried about AI regulation? What are his biggest concerns today?

  1. The Next AI Breakthrough: AI Agents

  • Why does Aaron believe the next big breakthrough in AI will be agents?

  • How does Aaron think AI agents will change org structures?

  • How does Aaron think agents will differ from RPA? How will RPA companies benefit from AI? 

  • What does Aaron think AI agents will look like in five years?

  1. Startups vs Incumbents: Who Wins?

  • What is Aaron’s advice to startups today building against OpenAI?

  • Does Aaron think startups have more advantage in foundational models or the application layer?

  • What advantages do incumbents have? What are their biggest weaknesses?

  • Who does Aaron think are the biggest winners in AI today? Who is underperforming?

  • Why does Aaron think Apple isn’t losing the AI race?

 

 

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