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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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Now displaying: Category: Investing
Mar 28, 2022

Jeff Lieberman is the Managing Director @ Insight Partners, one of the leading investing franchises of the last 25 years with their most recent flagship fund announced earlier this year being a staggering $20BN. As for Jeff, over the last 24 years at Insight, he has led investments in leading companies such as Qualtrics, DeliveryHero, HelloFresh, Cvent, Mimecast, and Udemy. As a result of his many investing successes, he has been selected by AlwaysOn as a Venture Capital 100 winner and by Forbes as a member of the Midas List.

In Today’s Episode with Jeff Lieberman You Will Learn:

1.) Origins into Venture:

  • How did Jeff's roommate at college open his eyes to the world of venture capital?
  • What were Jeff's biggest lessons from seeing the work ethic of his parents?
  • How does Jeff imbue the same level of ambition on his children that he had growing up with no money?
  • Why is Jeff keen for his children not to go to college? How does he advise them?

2.) Jeff Lieberman: The Investor:

  • What are Jeff's biggest observations on the current landscape given his seeing first hand the dot com bust and 2008? How is now different? How is it the same?
  • Price Sensitivity: How does Jeff reflect on his own price sensitivity? How has it changed over time?
  • Deployment Pace: How does Jeff analyse deployment pace today both for the industry and for Insight? Does Jeff agree with the notion of "playing the game on the field"?
  • The Biggest Miss: What have been some of Jeff's biggest misses? How did those misses impact the process with which he invests?

3.) Insight: The Firm

  • What are the most challenging elements of firm building today?
  • Why do all juniors have control over the Partners calendars? How does this work in practice?
  • How does Jeff create an environment of safety where very young, junior people feel like they can challenge anyone and have discussion?
  • How do Insight train young people? What is the process? What works? What does not work?

4.) AMA:

  • What does Jeff know now about venture that he wishes he had known when he started?
  • What would Jeff most like to change about the world of venture capital?
  • What advice does Jeff give to young people today entering the industry?

Item’s Mentioned In Today’s Episode with Jeff Lieberman

Jeff’s Favourite Book: Man's Search For Meaning

Jeff’s Most Recent Investment: Choco

Mar 25, 2022

Casey Winters is the Chief Product Officer at Eventbrite where he leads the PM, product design, research, and growth marketing teams. Prior to Eventbrite, Casey spent close to 3 years at Pinterest where he led the growth product team.

Andy Johns is one of the pre-eminent growth leaders of the last decade. Andy’s career started in growth at Facebook when the company scaled from 100M-500M active users. Since he has worked in some of the leading growth orgs at companies like Twitter, Quora and more recently at Wealthfront as Head of Growth and President.

Bangaly Kaba is the Head of Platform Growth @ Popshop Live, a live streaming mobile marketplace that combines commerce, entertainment, and social. Prior to Popshop, Bangaly led the product growth and consumer product orgs at Instacart and before Instacart was Head of Growth @ Instagram, where he built and led the product team that helped grow Instagram from 440M to > 1B monthly actives in 2.5yrs.

Elena Verna is a master when it comes to all things starting and scaling growth organizations. Previously, Elena spent over 7 years as SVP Growth @ SurveyMonkey where she ran product, growth marketing, and data teams. Post SurveyMonkey, Elena worked with the rocket ship that is Miro both as Interim CMO and as an advisor.

Ed Baker is an angel investor and growth advisor to various startups including Lime, Zwift, Whoop, Crimson Education, GoPeer, and Playbook. Ed was the VP of Product and Growth at Uber from 2013-2017. Prior to Uber, Ed was the Head of International Growth at Facebook.

Rob Schutz is Chief Growth Officer and Co-founder at Ro, the healthcare technology company building a patient-centric healthcare system. Under Rob’s growth leadership, Ro has become one of the fastest-growing companies in the country. Prior to Ro, Rob was VP of Growth at Bark, the makers of BarkBox, and helped scale revenue from zero to $100 million.

In Today’s Episode with Ed Baker You Will Learn:

1.) Casey Winters:

  • How does Casey define "growth"? How does it differ from product?
  • How do the best growth leaders decide between art vs science when making growth decisions?

2.) Andy Johns:

  • What is Andy's biggest advice to founders looking to build their first growth team?
  • What unexpected choice did Andy decide to make at Twitter that moved the needle for new user acquisition?

3.) Bangaly Kaba:

  • What were some of Bangaly's biggest takeaways from scaling Instagram from 440M users to 1BN?
  • What decisions did Bangaly make without data? How did they go? What did he learn?

4.) Ed Baker:

  • What are Ed's biggest takeaways from facebook around structuring growth teams?
  • What are Ed's biggest pieces of advice for startyups looking to grow internationally?
  • What were some of Ed's biggest learnings from working with Travis @ Uber?

5.) Elena Verna:

  • What is the difference between a good vs great growth model?
  • When does one need to change or amend their growth model? How does one know when it is working?

6.) Rob Schutz:

  • Why does Rob believe that startups should not diversify their customer acquisition channels too quickly?
  • How does Rob assess resouirce allocation and spend on new channels? How did this process look when partnering with the MLB for Ro?

Mar 23, 2022

Grant LaFontaine is the Founder & CEO @ Whatnot, the fastest-growing marketplace in the US, empowering people to make a living off their passion. To date, Grant has raised over $225M for Whatnot from the likes of CapitalG, a16z, YC, Scribble Ventures and Wonder Ventures to name a few. Prior to Whatnot, Grant was a PM @ Facebook working on the Oculus App Store and before that was the founder of Kit.com, ultimately acquired by Patreon.

In Today’s Episode with Grant LaFontaine You Will Learn:

1.) The Founding of Whatnot:

  • How did Grant make his way into the world of tech and startups?
  • What were some of his biggest lessons from Facebook? How did that impact how he has built Whatnot?

2.) Impossible To Hire Product Managers:

  • Why does Grant believe it is impossible to hire product managers today?
  • How does this impact the decision-making powers of engineers?
  • How does Grant test for this product knowledge in all engineers he adds to the team?
  • What are clear signals of 10x engineers in hiring processes?

3.) A/B Testing and Risk Mindset:

  • Why does Grant not believe in the effectiveness of A/B testing? Why does it not work?
  • Why does Grant believe one of the biggest reasons for startups failing is they do not take enough risk?
  • How does Grant try to ensure that his team takes as much risk as possible with everything that they do?
  • How does mindset to risk change with scale of company and with leadership?

4.) AMA:

  • Why does Grant disagree with founders angel investing?
  • What are the biggest challenges Whatnot has faced in scaling?
  • CEO coach? Who? When? What is the biggest lesson?
  • What is the single driving metric of Whatnot? How does Grant advise founders to determine their North Star metric?

Item’s Mentioned In Today’s Episode with Grant LaFontaine

Grant’s Favourite Book: Foundation: 1/3 (Foundation Trilogy)

Mar 21, 2022

Luciana Lixandru is a Partner @ Sequoia, one of the world’s most renowned and successful venture firms with Sequoia-backed companies accounting for more than 20% of NASDAQ's total value. As for Luciana, at Sequoia she has led investments in the likes of PennyLane, Xentral, Veed and Ledgy to name a few. Prior to joining Sequoia in 2020, Luciana was a Partner @ Accel where she made investments in Hopin, Miro, UiPath, Tessian and Deliveroo. As a result of such investing success, Luciana was #2 on the Midas List in 2021.

In Today’s Episode with Luciana Lixandru You Will Learn:

1.) Origins:

  • How did Luciana make her way from a small town in Romania to being Partner @ Sequoia?
  • What were the 1-2 crucible moments in her life that changed the course of her life?

2.) Luciana: The Investor

  • How has Luciana's investing style changed and developed over the years?
  • How does Luciana reflect on her own relationship to price? What misses caused these changes?
  • Hopin, Miro, Deliveroo, UiPath, how did having such winners so early impact Luciana's investing mindset?
  • What would Luciana say is her biggest insecurity today? What drives this?

3.) Sequoia: The Team

  • What are Luciana's biggest takeaways from working with Doug Leone, Alfren Lin, Roelof Botha and Pat Grady?
  • What does the decision-making process look like for new deals within Sequoia?
  • How does the Sequoia partnership create an environment of safety where everyone can discuss and debate freely?
  • How does Luciana approach training and mentorship? What works and what does not?

4.) Sequoia in Europe + Sequoia's Arc:

  • What is Arc? Why was now the right time for Sequoia to do it?
  • What is the structure for the program?
  • How many startups are part of it? Who is able to apply?
  • How much capital do the startups receive? What else do they receive in mentoring etc?
  • In 5 years time, what would success look like for Luciana with Arc?

Item’s Mentioned In Today’s Episode with Luciana Lixandru

Luciana’s Favourite Book: The Spy and the Traitor: The Greatest Espionage Story of the Cold War

Mar 16, 2022

Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and is one of the most popular newsletters on Substack. Lenny is also an extremely active angel investor with a portfolio including Figma, Sorare, Clubhouse, Vanta, WhatNot and many more incredible companies. If that was not enough, Lenny also has the best course on product management, check it out here.

In Today’s Episode with Lenny Rachitsky You Will Learn:

1.) Origins in Product:

  • How did Lenny make his way iunto the world of product management at Airbnb?
  • What were some of his biggest takeaways from his time at Airbnb on product?
  • What mistakes did he make on product at Airbnb? How did it impact his product thinking?

2.) Product Management: 101

  • How does Lenny define product management today? How is the role of PM changing?
  • When is the right time to hire your first PM as a startup?
  • What is the difference between Head of Product and CPO? When do you hire each?
  • What are the biggest mistakes founders make when hiring their first product hires?

3.) The Hiring Process:

  • How should founders breakdown the process of hiring for their first in product?
  • What does the interview process look like? How should founders structure it?
  • What core questions should teams ask of prospective candidates?
  • What are red flags when interviewing potential product hires?

4.) The Onboarding Process:

  • How should founders structure the onboarding process for new product hires?
  • What can founders do to make PMs successful in their first 30 days?
  • Where do many product hires make the biggest mistakes in the first 30 days?
  • What can product hires do to build trust with their new team?

Items Mentioned in Today's Episode with Lenny Rachitsky

Lenny's Fave Book: The Mom Test

Mar 14, 2022

David Friedberg is Founder and CEO of The Production Board (TPB), a holding company established to solve the most fundamental problems that affect our planet, by reimagining global systems of production. Prior to founding The Production Board, David founded The Climate Corporation, a 10-year journey that culminated in their $930M acquisition by Monsanto. If that was not enough, David is the Founder and Chairman at Metromile and also sits on the board of Soylent, Clara Foods, Tillable, Cana Technologies and more.

In Today’s Episode with David Friedberg You Will Learn:

1.) Origins:

  • How David made his way into the world of startups and technology from academia and physics?
  • What were David's biggest takeaways from scaling The Climate Corp to $930M exit to Monsanto?
  • How did the exit put pressure on David for all future companies he builds? How does he manage that?

2.) The Macro: Venture + The Economy

  • How does David foresee the impending rate hikes? What impact will this have on venture and the economy?
  • What segment of the market will be first to be hit? Why is growth investing last to be hit? How does early stage play out in this very new environment?
  • How will we see the velocity of capital deployment change in this new period? What does David believe are some of the crucial flaws of the venture model?
  • How does David reflect on his own price sensitivity? What lessons has he learned from deals he has done or missed that have changed his perspective?

3.) David Frankel: The Business Builder

  • What is David's rubrik for business value creation? How has this changed with time?
  • How mentally plastic does one have to be around the time it takes to see margins, unit economics etc change from negative to positive?
  • How does David and the team approach building new companies at TPB? Where do they find the founding teams? How do they incentivise them?
  • How does TPB approach continuous funding for the companies they create? What milestones need to be hit? How do they assess them?
  • How does David approach liquidity with regards to exits for the companies they create? Why does their holding company structure mean they have different incentives to VCs?

4.) David Friedberg: Father and Husband

  • How does David reflect on his own relationship to money today? How has it changed over time?
  • What have been David's biggest realisations on what provides him true happiness?
  • How did having children change his operating mentality? What does being a great father mean to David?

Item’s Mentioned In Today’s Episode with David Friedberg

David’s Favourite Book: Zen Mind, Beginner's Mind

Mar 11, 2022

Sid Sijbrandij is the Co-founder & CEO @ GitLab. GitLab’s single application helps organizations deliver software faster and more efficiently while strengthening their security and compliance. Prior to their IPO last year, Sid raised funding from some of the best including ICONIQ, GV, Tiger, Coatue and D1 to name a few. Under his leadership, the company has grown to over 1,500 employees and over 30 million registered users. If that was not enough, Sid is also an active angel and sits on the board of Meltano, a spinout of Gitlab that allows you to manage all the data tools in your stack.

In Today’s Episode with Sid Sijbrandij You Will Learn:

1.) The Founding of Gitlab:

  • How did Sid make his way into the world of tech and startups?
  • What was it about Gitlab as a project that excited Sid so much from Day 1?
  • How did Sid convince his co-founder to turn Gitlab from a project into a company?

2.) The Future of Work:

  • Why does Sid believe it is a fallacy that everyone will go back to the office?
  • What are the 1-2 most important things for companies to do when moving to a remote work environment? Where does Sid see many make mistakes?
  • What have Gitlab done to create a remote working environment so successfully? What have they tried that has not worked?
  • What stage of company building does remote work best for? When is it most challenging?

3.) Sid: The Leader

  • How has Sid changed and evolved as a leader over the Gitlab journey?
  • How does Sid look to get as much feedback as possible on his leadership?
  • How does Sid create an environment of safety where everyone feels they can provide feedback?
  • How does Sid work with his CEO coach? Should every CEO have one? What should one look for in them? How do you know when you need to change your CEO coach?

4.) Sid: The Board Member:

  • What have been Sid's biggest lessons on what makes successful board management?
  • In prep for the meeting, what materials does Sid provide? When does he send them? Does he present to the board? What mistakes do founders make in boards?
  • From being on the other side as a board member, what does Sid believe the best members do?
  • What would Sid most like to change about board meetings today?

Item’s Mentioned In Today’s Episode with Sid Sijbrandij

Sid’s Favourite Book: High Output Management

Mar 9, 2022

Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. In this role, Jeanne is responsible for all sales functions across the region including Sales Development, AEs, Solutions Architects, and many more. Jeanne also continues to spearhead Stripe's Enterprise strategy. Prior to this role, Jeanne was Stripe's Head of North America Sales where she built out Stripe's Acquisition Sales teams. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM.

In Today’s Episode with Jeanne DeWitt Grosser You Will Learn:

1.) Entry into Sales:

  • How did Jeanne make her way into her first sales job in tech?
  • What did Jeanne learn from her many years at Google about how sales should interact with engineering?
  • In hindsight, what would Jeanne have done differently/improved from her time with Dialpad?
  • How did the role with Stripe come about?

2.) The Playbook:

  • Does the founder need to be the one to create the sales playbook?
  • When is the right time to bring in the first sales hire? Should they be a sales leader or rep?
  • How does both the playbook and the type of sales hire change when hiring for a product-led-growth motion vs a traditional enterprise motion?
  • What are the single biggest mistakes founders make when hiring their first in sales?

3.) The Hiring Process:

  • How should founders structure the hiring process for their first sales hires?
  • What did Dialpad do in the sales hiring process that worked well? How has Jeanne taken that to her hiring process at Stripe?
  • What should be achieved or learned in each consecutive interview?
  • How can founders use sales case studies most effectively? How can founders know if sales candidates truly have a strong grasp of the product?
  • What are early signs of a 10x sales hire? What are red flags to look out for in the process?

4.) Sales Onboarding:

  • What does the ideal onboarding process look like for new sales hires?
  • What tasks and duties should all sales hires perform in the first 60 days?
  • What are early signs that a new hire is not performing to the right standard?
  • How does the first few months differ for sales reps when comparing a product-led-growth company to an enterprise company?
  • What should sales leaders do to ensure that new hires engage with product and customer success efficiently?

Mar 7, 2022

Harley Finkelstein is the President of Shopify, the platform modern commerce is built on. Over the last 12 years, Harley has partnered with Tobi to the tune of building Shopify's revenue to over $4.6BN in 2021 and the team to over 10,000 employees. On the side, Harley is an Advisor to Felicis Ventures and in the past has held board seats at CBC, Omers Ventures and The C100. If that was not enough, you can see Harley on a screen near you as one of the “Dragons” on CBC’s Next Gen Den.

In Today’s Episode with Harley Finkelstein You Will Learn:

1.) The Founding Story:

  • What was Harley's first entrepreneurial endeavour?
  • How did seeing his family lose everything impact Harley's mindset and ambition?
  • How did Harley first meet Tobi @ Shopify? How did the Shopify journey begin?

2.) Leadership Lessons:

  • How has Harley changed as a leader over the 13 years with Shopify?
  • How does Harley embrace vulnerability and authenticity in his communication with the team?
  • What is Harley most insecure about when he looks at leadership today?
  • What have been some of the biggest lessons Harley has learned from his board on what great leadership is?

3.) The Art of Marriage:

  • What does Harley believe makes the most successful marriage?
  • Why have Harley and his wife been seeing a marriage therapist from the early days?
  • What is the biggest mistake people make when communicating with partners?
  • How has Harley changed as a husband over the years?

4.) The Joy of Fatherhood:

  • Does Harley always believe he has been a good father?
  • What was his realisation moment that he was not being the father he wanted to be?
  • What core elements of his behaviour did he change? How did that impact his relationship with his kids?
  • How does Harley ensure he performs at the highest level while also being there and being present for his family?

Item’s Mentioned In Today’s Episode with Harley Finkelstein

Harley’s Favourite Book: The Book of Ichigo Ichie: The Art of Making the Most of Every Moment, the Japanese Way

Feb 28, 2022

Scott Dietzen is Vice Chairman of the Board of Pure Storage and served as the Company’s CEO from 2010 to 2017. Under his leadership, Pure grew to thousands of employees and
completed an IPO in 2015. Dietzen is a four-time successful entrepreneur with WebLogic, Zimbra, and Transarc. Before Pure, he was President and CTO of Zimbra (now part of VMware), but originally acquired by Yahoo!, where Dietzen served as interim SVP of Communications and Communities. Prior to Zimbra, Dietzen was CTO of BEA Systems, where he helped craft the technology and business strategy for WebLogic that drove BEA from $61m in annual revenues prior to the WebLogic acquisition to over $1B.

In Today’s Episode with Scott Dietzen You Will Learn:

1.) The Journey to Pure Storage CEO:

  • How did Scott make his way into the world of tech and startups?
  • What was the hardest element of making the transition from CTO to CEO?
  • What advice would Scott give to more technical leaders looking to make the move to CEO? Where do so many make mistakes?

2.) How To Build Trust in a Team:

  • What are the most important ways that leaders can build trust with their teams?
  • How can leaders be honest and share the hard truths without damaging role?
  • What is the right tone to communicate both the big wins and big losses?
  • Why does Scott always believe the losses teach more? How does Scott approach post-mortems?

3.) The Biggest Mistakes Founders Make:

  • What are the single biggest hiring mistakes that founders make?
  • What are the single biggest firing mistakes executives make?
  • Why should founders sometimes say no to customers?
  • How should founders approach investor selection and valuation for rounds?

4.) How to Optimise a Board:

  • What specifically can founders do to optimise their board?
  • What are the biggest errors founders make when communicating with their board?
  • What is the value per word framework? How does it tell which board member is the best?

Item’s Mentioned In Today’s Episode with Scott Dietzen

Scott’s Favourite Book: The 22 Immutable Laws Of Marketing

Feb 25, 2022

Sahil Bloom is the Founding Partner @ SRB Ventures, a $10M fund that leverages the 500K followers Sahil has amassed to invest at the intersection of venture and media. Previously, Sahil spent 7 years at a large investment fund managing >$3.5 billion in capital and serves on the board of 4 companies. He has also been an active angel investor in over 30 companies.

In Today’s Episode with Sahil Bloom You Will Learn:

1.) How Sahil made his way from a career in traditional finance to building a media company and leveraging that to raise the latest SRB fund? How does Sahil advise others is the best way to "find their zone of genius"?

2.) How To Build a Media Engine:

  • What have been some of Sahil's biggest lessons on what works on Twiter and what does not work?
  • What is the golden rule for Twitter?
  • How does Sahil plan and come up with ideas for his Twitter threads? What tools and software does he use? How long does each thread take?

3.) The End of the Road for Traditional Venture:

  • Why does Sahil think traditional venture is dying?
  • What newcomers will take the place of the existing incumbents?
  • Why does he think they are weak? What do new players provide that they do not?
  • Which existing players will remain and be strong? Which will fade out?
  • Does Sahil believe that VCs really provide any value?

4.) SRB Ventures:

  • Why did Sahil decide to raise the new fund?
  • How did he decide on size of the fund? What is the strategy? What is the portfolio construction?
  • How does SRB provide media services others do not?
  • How did Sahil meet Tim Cook and get him to invest in the fund?
  • What is the biggest thing Sahil believes most people misunderstand about luck?

Item’s Mentioned In Today’s Episode with Sahil Bloom

Sahil’s Favourite Book: When Breath Becomes Air: Kalanithi Paul

Sahil’s Most Recent Investment: Wander

Feb 23, 2022

Tiger Global are one of the most discussed venture firms on the planet. With a deal cadence and capital deployment speed that is unmatched, they have made their mark on the venture landscape like no other over the last 24 months. Today we are joined by leaders from Sequoia, Benchmark, Thrive Capital, General Atlantic, GGV and Aleph to discuss the rise of Tiger and how it impacts the venture ecosystem.

In Today’s Episode on Tiger Global You Will Learn:

1.) Doug Leone: Sequoia Capital

  • Why we need to change the words when use in venture? Why we need to get rid of "the game"?
  • How does the rise of Tiger compare to the rise of prior entrants with the same approach?
  • Why does Doug believe that the craft of venture will persist despite these new entrants?

2.) Bill Gurley: Benchmark Capital

  • How does Bill analyse the change in late stage venture today?
  • What are the main drivers of the increased competition in late stage venture?
  • Why does Bill get concerned not by Tiger but how others respond to Tiger's model?
  • How does Bill analyse the entry of hedge funds and PE funds into traditional venture models?

3.) Michael Eisenberg: Aleph

  • How does Michael think about the "weaponisation of capital"?
  • What are the significant benefits for a fund of having more capital than their competitors?
  • How does this capital advantage change in boom and bust times?

4.) Anton Levy: General Atlantic

  • Why does Anton believe that funds are leveraging their assets more efficiently than ever?
  • How does Anton approach the mindset of AUM scaling without lowering returns?
  • Why does Anton never want to compete on price?
  • How does GA think about competing in a world of Tiger and hedge funds investing in tech?

5.) Hans Tung: GGV

  • Why did Hans always believe the model to look at moving forward was Tiger?
  • Why does Tiger's business model allow them structural and financial advantages over their competitors?
  • What does Hans make of the data network effects of Tiger with their strategy?

6.) Kareem Zaki: Thrive Capital

  • Why does Kareem think Tiger's approach makes absolute sense?
  • Why does Kareem believe so many in venture like to try and discredit the Tiger model?
  • How does Tiger's approach differ to Thrive's?

Feb 18, 2022

Max Rhodes is the Co-Founder and CEO @ Faire, the online marketplace where retailers discover their next bestsellers from independent brands across the globe. To date, Max has raised over $1.1BN with Faire from some of the best including Sequoia, Founders Fund, DST, Forerunner, Lightspeed and many more. Prior to starting Faire, Max spent close to 5 years at Square in numerous different roles including Director of Consumer Product at Caviar.

In Today’s Episode with Max Rhodes You Will Learn:

1.) The Founding Story:

  • How Max made his way into the world of startups with his joining an early Square team?
  • How did his 5 years at Square impact how he approaches company building with Faire?
  • How did Square's approach to product and mission impact Max's thinking?

2.) How To Hire Effectively:

  • How does Max construct the hiring process? Where do many founders make mistakes?
  • What does Max mean by "deep behavioural interview"? What questions does he ask?
  • What are the signals of 10/10 candidates? What are red flags he looks for?
  • How does Max determine capability? What literal tests can be done to test for this?

3.) How To Reference People:

  • How does Max approach the referencing process when hiring people?
  • How does Max make the other side feel comfortable, so they will open up and share everything?
  • What have been some of Max's biggest lessons on what it takes to do referencing well?
  • Where do many make mistakes with referencing?
  • How does Max use an "out of 10" system to determine the quality of the candidate?

4.) How to Strategise:

  • How does Max use strategy docs to orient the direction of the company?
  • How often does Max write them? How long do they take to write?
  • What are the core components of the strategy docs?
  • Who else is involved in their writing? Once written, what is the right format to discuss with the team?
  • How does Max approach how rigid he is to the strategies outlined? How does he determine whether he should change strategy or stick to plan?

Item’s Mentioned In Today’s Episode with Max Rhodes

Max’s Favourite Book: Good Strategy Bad Strategy, Who: The A Method for Hiring

Feb 16, 2022

Ed Baker is an angel investor and growth advisor to various startups including Lime, Zwift, Whoop, Crimson Education, GoPeer, and Playbook. Ed was the VP of Product and Growth at Uber from 2013-2017. Prior to Uber, Ed was the Head of International Growth at Facebook, a company he joined after they acquired a startup he co-founded called Friend.ly, which had grown to over 25 million users.

In Today’s Episode with Ed Baker You Will Learn:

1.) Ed Baker: Entry into Growth:

  • How Ed made his way into the world of growth from his start founding a dating site while at Harvard?
  • How he made his way to lead international growth at Facebook? How his time with Facebook led to his joing Uber to start Uber's growth team?
  • What were Ed's biggest lessons from Uber and Facebook? How did his approach to growth and mindset change as a result of his time there?

2.) When is the Right Time:

  • When is the right time for startups to hire their first growth leads or reps?
  • How should they determine whether to promote from within or hire externally?
  • What are the biggest mistakes startups make on the timing of this hire?
  • How can startups accurately assess whether they have product-market-fit?

3.) Who To Hire:

  • Step by step, how does Ed structure the interview process for all new growth hires?
  • What are the must ask questions for growth leaders to ask candidates in interviews?
  • What are the clear signs and answers that suggest a 10x growth hire?
  • What literal tests does Ed do to determine the quality of a hire? How do the best perform?

4.) Onboarding and Integration:

  • What is the optimal onboarding process for all new growth hires?
  • How do the best growth hires start in the first 60 days? What do they achieve?
  • What are some of the early signs that a growth hire is not working out?
  • How should the relationship be between the CEO and the Head of Growth?
  • How can the Head of Growth foster a strong relationship between growth and product teams?

Feb 14, 2022

Geoff Lewis is the Founder and Managing Partner @ Bedrock, now with over $1BN in AUM, Bedrock invests in breakout technology companies that are incongruent with popular narratives. In the past, Geoff has backed some generational defining companies such as Wish, Lyft, Nubank, RigUp, Vercel, Anduril and many more. Prior to founding Bedrock, Geoff was a Partner @ Founders Fund.

In Today’s Episode with Geoff Lewis You Will Learn:

1.) How Geoff made his way into the world of venture with his joining Founders Fund? How his time with Founders Fund led to his co-founding Bedrock with Eric?

2.) Geoff Lewis: The Investor:

  • How does Geoff reflect on his own relationship to price? How does he determine when to pay up vs walk away?
  • How does Geoff approach the re-investment decision-making process? Where do most go wrong when it comes to allocating reserves?
  • What have been some of Geoff's biggest misses? How did they impact his investing mindset?
  • Why does Geoff not believe that ownership is as crucial as other VCs suggest?

3.) Bedrock: The Firm

  • What have been some of the biggest challenges in building Bedrock?
  • Where does Geoff believe many firms make core mistakes in firm building?
  • What are the differences between principles and rules? Why does Geoff believe all firms need to have principles?
  • How does Geoff approach internal talent building? What are the signals of people that will succeed in venture? How do they approach learning?

4.) The Market:

  • How does Geoff analyse the current state of the venture market?
  • Does Geoff agree with the notion of "play the game on the field"?
  • Why does Geoff think markups are BS and just VCs looking for external validation?
  • How has Geoff learned to isolate from the VC community and retain that purity of mindset working with great entrepreneurs?

Item’s Mentioned In Today’s Episode with Geoff Lewis

Geoff’s Favourite Book: Friedrich Nietzsche

Geoff’s Most Recent Investment: Praxis

Feb 11, 2022

Aaron Levie is the Founder and CEO @ Box, the company incorporating the best of secure content collaboration with an intuitive user experience suited to the way people work today. Prior to their IPO in 2015, Aaron raised from some of the best in the business including the main man Mark Cuban, a16z, Emergence, DST, Coatue, DFJ and many more. Aaron founded the company from his dorm room at the University of Southern California and has led the company to 1,900 employees and over $770M in revenue, as of 2021 data.

In Today’s Episode with Aaron Levie You Will Learn:

1.) How Aaron founded Box from his dorm room at the University of Southern California? What was that founding a-ha moment? What did the first year look like? Does Aaron agree, "serial entrepreneurship is overrated"?

2.) Phases of Leadership and Company Growth:

  • How does Aaron define the different phases of leadership required as a company grows?
  • Which phase did Aaron find the most challenging? How did he overcome it?
  • What are the first things to break when companies grow? What can founders do to prevent this?
  • Does Aaron agree, "the best CEOs are the best resource allocators"?

3.) The Market:

  • How does Aaron thinkj about the dislocation between private company valuations and public company market caps?
  • What does Aaron believe are the biggest challenges founders face when they are over-capitalised?
  • What does Aaron mean when he says, "raise when cash is cheap, spend as if it was expensive"? How does Aaron advise founders on fundraising today?

4.) The Team and Culture:

  • How does Aaron create a safe space where all team members can come to him with anything?
  • How does Aaron approach effective goal setting? How does one balance between achieveable and also aggressive goals?
  • How does Aaron approach the art of delegation? What is his decision-making framework for what to delegate vs what to control?

Item’s Mentioned In Today’s Episode with Aaron Levie

Aaron’s Favourite Book: Innovator's Dilemma: When New Technologies Cause Great Firms to Fail (Management of Innovation and Change)

Feb 9, 2022

Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe’s Chief Product Officer and Executive Vice President, Creative Cloud. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, the leading online platform for the creative industry, and served as CEO until Adobe acquired Behance in 2012. Behance now has over 25M members. Scott is also an early advisor and investor in Pinterest, Uber, Sweetgreen, Carta, Flexport, Airtable, and several others. Finally, if that was not enough, Scott is the author of two national bestselling books - Making Ideas Happen and The Messy Middle.

In Today’s Episode with Scott Belsky You Will Learn:

1.) Narrow the Focus, Increase the Quality:

  • What does Scott believe is the core challenge in product?
  • What was the single biggest product challenge Scott faced at Behance? How did they overcome it?
  • When should product teams listen to customer feedback vs ignore it?
  • What are the core questions product teams should ask user groups to extract the most feedback and value?

2.) The Importance of the First Mile:

  • What does Scott believe makes a great first mile when it comes to the product experience?
  • Where do so many companies go wrong in creating the first mile user experience?
  • Which company at scale has retained this simplicity of the first mile? How did they do it?
  • What does Scott mean when he says, "the devil is in the defaults"? What can product teams learn from this?

3.) The Makings of a Great Product Leader:

  • What are the 3 core questions every great product leader should ask on every screen?
  • How do the best product leaders structure product reviews?
  • Who is invited to product reviews? How often are they? Who sets the agenda? When is it sent?
  • What do the best product leaders do to retain direction and productivity in reviews when there are many people and many ideas? How do they stay on track?

4.) The Hirings of a Great Product Team:

  • How can founders know whether to hire the product leader or retain the role? When is the right time?
  • What are the single biggest mistakes founders make when hiring their first product hires?
  • How should founders structure the hiring process for product hires? What should they look to gain from each interview?
  • What are the must ask questions in those interviews? How do the best respond?
  • What case studies or physical tests can be done to determine the quality of a candidate?

Feb 7, 2022

David Frankel is a Co-Founder and Managing Partner @ Founder Collective, one of the great seed firms of the last decade with a portfolio including Uber, Coupang, Airtable, Whoop and many more incredible companies. Previously, David was Co-Founder and CEO of Internet Solutions (IS), the largest ISP in Africa, ultimately acquired by NTT. David is also a founding board member of Endeavor SA and in the past has been selected by the World Economic Forum for the Global Leader of Tomorrow (GLT) program.

In Today’s Episode with David Frankel You Will Learn:

1.) How David made his way into the world of angel investing? How his mindset changed when making the transition from angel to an institutional investor with the founding of Founder Collective?

2.) Building the Firm: Founder Collective

  • What are the biggest challenges in venture firm building today?
  • Why is "deploy" and "the game" banned as words within Founder Collective? What terms are promoted as an alternative?
  • How does David construct investment decision-making in the partnership?
  • How does David create a safe space where all team members can share their thoughts in a non-judgemental, safe environment?
  • What are the biggest mistakes or challenges that David sees firms make when building?

3.) David Frankel: Investor Mindset

  • How does David analyse the current seed market today? What does he like? What worries him?
  • Does David agree that early stage investing has never been less collaborative?
  • How does David reflect on his own relationship to price today? How does he determine when to pay up vs when not to?
  • How does David think about the compression on fund deployment timelines? Will this change?
  • How does David keep a fresh and clean mind when viewing new opportunities, having seen many work and not work? How does one retain that mental purity when investing?
  • What have been some of David's biggest misses? How did it impact his style of investing?

4.) The Partnership:

  • What was the most recent disagreement David had with the partnership? How was it resolved?
  • How does David approach self-doubt and insecurity within the partnership? How can this be managed successfully?
  • What have been some of David's biggest lessons on how to give effective feedback without being judgemental?
  • In a world of Zoom, how did the partnership retain the same level and quality of connection that they had in person? What works? What does not work?

Item’s Mentioned In Today’s Episode with David Frankel

David’s Favourite Book: The Code Breaker: Jennifer Doudna, Gene Editing, and the Future of the Human Race

David's Most Recent Investment: PairTree

Feb 4, 2022

Mark Cuban is a serial entrepreneur, investor, and owner of the Dallas Mavericks. Today we are focused on Mark's latest entrepreneurial endeavor, starting Mark Cuban's Cost Plus Drug Company, the online pharmacy taking out the middlemen, meaning no price games and huge drug savings. As mentioned, Mark is also the proud owner of Dallas Mavericks, since his taking over they have competed in the NBA Finals for the first time in franchise history in 2006 – and became NBA World Champions in 2011. Before Dallas Mavericks, Mark co-founded Broadcast.com – streaming audio over the internet. In just four short years, Broadcast.com (then Audionet) was sold to Yahoo for $5.6 billion dollars. If that was not enough, Mark is also one of ABC’s “Sharks” on the hit show Shark Tank.

In Today’s Episode with Mark Cuban You Will Learn:

1.) Cost Plus Drugs: Origin

  • Why Mark decided to build Cost Plus Drugs?
  • Why has no one done it before?
  • How does Mark think about resource and time allocation with Cost Plus?

2.) Building the Team: Hiring

  • How does mark analyze his approach to hiring? Where is he weak? Where is he strong?
  • What one motto does Mark always use when it comes to hiring?
  • What is the most common mistake Mark sees founders make when it comes to team build?
  • How does Mark identify stress removers? What are the core signals?

3.) Brand + Capital + Business Strategy:

  • Why is the current cost structure of healthcare so damaged in the US? How does Cost Plus change this?
  • How does Mark think about what it takes to build great brand today? Why will Cost Plus not be doing big TV and traditional media advertising?
  • What types of guerilla marketing is Mark most excited by? Why will Mark never have a billboard in Times Square?

4.) AMA with Mark Cuban:

  • What 3 traits does Mark most want his children to adopt?
  • What worries Mark most today?
  • What are Mark's biggest strengths? What are his biggest weaknesses?
  • What single purchase has brought Mark the greatest joy?

Feb 2, 2022

Dannie Herzberg is a Partner @ Sequoia Capital and one of the great sales leaders of the last decade. Prior to entering the world of venture, Dannie spent 4 years at Slack as their Head of Enterprise Sales, there Dannie built & scaled the self-serve / SMB, mid-market, and enterprise sales orgs across the Americas as Slack grew from $100M - $1B in revenue. Before Slack, Dannie spent over 5 years at Hubspot building sales, opening an SF office, and then joining product to launch CRM & platform.

In Today’s Episode with Dannie Herzberg You Will Learn:

1.) How Dannie got her first job in sales at Hubspot through being a waitress in a Boston Diner? What were her biggest lessons from her 5 years scaling sales at Hubspot? How did Dannie's 4 years at Slack impact her operating and sales mindset today?

2.) The Playbook:

  • Does the founder need to be the one to create the sales playbook?
  • When is the right time to bring in the first sales hire? Should they be a sales leader or rep?
  • When is the right time to bring in a CRO, sales enablement and revenue ops?
  • What are the single biggest mistakes founders make when hiring their first in sales?

3.) The Hiring Process:

  • How should founders structure the hiring process for their first sales hires?
  • What should be achieved or learned in each consecutive interview?
  • How can founders use sales case studies most effectively?
  • What are early signs of a 10x sales hire? What are red flags to look out for in the process?

4.) Sales Onboarding:

  • What does the ideal onboarding process look like for new sales hires?
  • What tasks and duties should all sales hires perform in the first 60 days?
  • What are early signs that a new hire is not performing to the right standard?
  • How does the first few months differ for sales reps when comparing a product-led-growth company to an enterprise company?
  • How can new sales hires really engage with broader functions within the team in the first 30 days?

Item’s Mentioned In Today’s Episode with Dannie Herzberg

Inbound Marketing, Revised and Updated: Attract, Engage, and Delight Customers Online

Jan 28, 2022

Scott Sandell is the Managing General Partner of NEA, one of the leading firms of the last 3 decades with now close to $24Bn under management and a portfolio including Salesforce, Robinhood, Plaid, Databricks and more. As for Scott, since joining the firm in 1996 he has led investments in Salesforce.com, Tableau Software, WebEx and Workday and serves on the board of Robinhood, Cloudflare, Coursera and Divvy to name a few. 

Rick Yang is a General Partner and Head of Consumer Investing @ NEA, since joining in 2007 he has led investments in the likes of Masterclass, Plaid, Robinhood and many more.

In Today’s Episode with Scott Sandell and Rick Yang You Will Learn:

1.) How Rick came to meet Vlad, Robinhood Founder, for the first time? What impressed Rick most in that first meeting? How did the internal discussions proceed at NEA? Was it a unanimous decision to make the investment?

2.) The Market:

  • How did Rick and Scott evaluate the market at the time? Bottoms up, top down?
  • How did the market change and evolve both in ways they did and did not expect?
  • How do Rick and Scott evaluate market timing risk today when investing?
  • How did Rick and Scott approach outcome scenario planning with Robinhood?

3.) The Traction:

  • What core signals and datapoints made Rick realise Robinhood had product-market-fit?
  • How did Rick and NEA analyse Robinhood's early organic customer acquisition? How did the board advise on how to spend their first marketing dollars?
  • How does the cost structure of the business compare to Charles Swaab and eTrade? Why is Robinhood such a superior model?

4.) The Team: 

  • How has Vlad evolved and developed as a leader over time?
  • How did Vlad handle the 36 hours in Feb 2021 when he had to go and raise $3BN+?
  • Who is the unsung hero of the Robinhood team? What have they done to deserve this?

Jan 26, 2022

Jonathan Neman is Co-Founder & CEO of Sweetgreen, the mission-driven restaurant brand that serves healthy food at scale. Alongside his co-founders, Jon has scaled Sweetgreen from one small restaurant to one of the US' leading food brands with over 5,000 employees, over 140 locations and $300M+ in revenue. If that was not enough, Jon is also an active board member of MeUndies.

In Today’s Episode with Jonathan Neman You Will Learn:

1.) How Jon took the decision to leave his "dream job" as a consultant at Bain to start Sweetgreen? What did his Bain boss tell him that persuaded Jon it was the right decision to leave? How does Jon think about and advise people when it comes to choosing the safe vs the risky path?

2.) How Sweetgreen was not an Overnight Success:

  • At what moment did Jon really not think that Sweetgreen would make it? Why?
  • How did he deal with those moments of intense stress and pressure?
  • How does Jon test for true grit and resilience both in hires and in founders today?

3.) Brand + Capital + Business Strategy:

  • How does Jon think deeply about what brand means today?
  • What did Sweetgreen do right when it comes to their brand building? How did they marry art and science in the right way?
  • What do the unit economics look like on a per store basis? What is the payback period on a per store basis? How has this changed over time?
  • How does the store design impact the profit per store? How has store design changed over time?
  • What have been some of the biggest lessons in terms of when, where and how to open new stores?

4.) Leading Through COVID:

  • What were some of Jon's biggest lessons from leading a consumer brand through COVID
  • What were some of the toughest elements for Jon? How did he overcome them?
  • How can founders bring people along with their thought process and inspire?
  • Who is Jon's biggest mentor? What has he learned from them?

Item’s Mentioned In Today’s Episode with Jonathan Neman

Jon’s Favourite Book: Thinking, Fast and Slow: Daniel Kahneman

Jan 24, 2022

Anne Wojcicki is the Founder & CEO @ 23andme, offering DNA testing with the most comprehensive ancestry breakdown, personalized health insights, and more. To date, Anne has raised over $1BN for the company from the likes of Sequoia, GV, NEA and many more incredible names. Prior to founding 23andMe, Anne spent a decade on Wall Street investing in healthcare and felt frustrated by a system built around monetizing illness instead of incentivizing prevention. If that was not enough, Anne is also on the board of Cazoo and The Anne Wojcicki Foundation and is an active angel investor with investments in the likes of Embark and Maven Clinic.

In Today’s Episode with Anne Wojcicki You Will Learn:

1.) How Anne made her way from Wall St healthcare investing to founding one of the leading healthcare companies of the last decade in 23andme?

2.) Trust and Friendship:

  • How does Anne determine whether someone is genuine or is being transactional? What are the signs?
  • How does Anne approach trust in relationships? Start from a base of full trust and it is to be lost or start with none and it is to be gained?
  • What does Anne believe are the core of the best and most healthy relationships she has?

3.) Leadership:

  • How does Anne reflect on her own decision-making processes today?
  • How does Anne create a safe space where her team feel they can pushback on her and tell her how they feel?
  • How does Anne approach internal role migration? What does Anne do to get the very best out of her team?
  • How has Anne's leadership style changed over the years?
  • How has being on the board of Cazoo changed how Anne reflects on her own board leadership? What have been some of her biggest lessons from Alex Chesterman?

4.) AMA:

  • What is the hardest element of Anne's role with 23andme?
  • What is Anne's morning routine?
  • What 3 traits would Anne most want her children to have?
  • Anne can have a billboard anywhere, what do it say on it and why?
  • What would Anne most like to change in the world of healthcare over the next decade?  

Jan 21, 2022

Ali Partovi is the CEO @ Neo, a mentorship community and communal VC fund that announced their new $150M fund last year on the back of early hits from Fund I including Vanta and Kalshi. As an angel, Ali has made personal investments in Dropbox, Uber, Airbnb, Facebook, Convoy and many more. Prior to investing, Ali founded 2 companies, the first; LinkExchange which he sold to Microsoft for $265M in 1998 and the second, iLike which was acquired by Microsoft in 2009.

In Today’s Episode with Ali Partovi You Will Learn:

1.) How Ali made his way into the world of startups with the founding of his first company? How Ali made his way into angel investing and then starting and raising Neo, as a fund?

2.) How To Kill a $125M By Being Too Honest:

  • How did Ali lose this $125M with Jerry Yang and Yahoo?
  • What led Ali to believe that Paul Graham was so special in 1995? What would Ali have done differently with the benefit of hindsight?
  • How does Ali feel about investment misses today? What are his biggest misses? How has it impacted his mindset and approach to investing?

3.) The Meeting with Steve Jobs Did Not Go Well:

  • Why did the meeting with Steve Jobs not go well?
  • What was wrong with the way Ali phrased his final statement? What did this teach Ali about how founders should communicate the difference between hype and reality?
  • What did this experience teach Ali about how founders should run both fundraising and M&A processes? How does Ali build trust with every touchpoint?

4.) U2, Airbnb and Google at Seed:

  • How did Bono come to save the day for Ali for his startup in 2009?
  • What did this teach Ali about how to frame risk and when to go all in vs hold back?
  • How did Ali miss investing in the seed for Airbnb? How did he make up for it with a later investment?
  • How did Ali come to miss investing in the Google seed round? Does FOMO haunt Ali today?

Item’s Mentioned In Today’s Episode with Ali Partovi

Ali’s Favourite Book: Sapiens: A Brief History of Humankind

Jan 19, 2022

Rob Schutz is Chief Growth Officer and Co-founder at Ro, the healthcare technology company building a patient-centric healthcare system. To date, Ro has raised over $870M with a last reported valuation of $5BN and under Rob’s growth leadership, Ro has become one of the fastest-growing companies in the country. Prior to Ro, Rob was VP of Growth at Bark, the makers of BarkBox, and helped scale revenue from zero to $100 million. He also founded a Washington DC-based daily deals site that was acquired by kgbdeals in 2011.

In Today’s Episode with Rob Schutz You Will Learn:

1.) How Rob made his way into startups and growth through the world of daily deals? How that led to his leading growth for Bark and ultimately founding Ro? How did leading marketing for Bark impact his growth strategy today with Ro?

2.) What is "Growth" and When to Hire For It:

  • How does Rob define "growth and "Head of Growth"?
  • When is the right time to start thinking about a growth team?
  • Should founders hire a "Head of Growth" first or hire younger growth reps?
  • Where should the growth team sit within the organization?

3.) How to Hire Growth Leader and Reps:

  • What is the step-by-step process to hire growth leaders and reps?
  • How does it differ when hiring growth leaders vs reps?
  • What questions does Rob always ask? What separates good from great answers?
  • What case studies does Rob like to use to determine candidate quality?
  • How can one tell whether marketeers and growth candidates truly understand data?

4.) How to Structure the Onboarding Process:

  • What does the optimal onboarding process look like for new hires?
  • What tasks and duties do you expect reps and growth leaders to complete in the first month? 
  • What are some early red flags that the candidate you have is not good enough?
  • How can leaders deliberately manufacture moments for growth teams to interact with other teams?
  • What are the biggest mistakes growth teams and leaders make in the early days?

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