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 for more information on the podcast, show notes, resources and more.
RSS Feed
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch










All Episodes
Now displaying: March, 2022
Mar 30, 2022

Olivia Nottebohm is the Chief Revenue Officer @ Notion where she leads the Sales, Marketing, Customer Success and Customer Experience teams. Prior to Notion, Olivia was the COO @ Dropbox where she achieved the first 4 quarters of profitable growth. Before Dropbox Olivia spent over 5 years at Google including as VP Cloud GTM Operations and Global SMB Sales. Finally, before Google, Olivia spent a whopping 15 years at McKinsey & Company.

In Today’s Episode with Olivia Nottebohm You Will Learn:

1.) Origins:

  • How Olivia made her way into the world of startups and tech?
  • What are 1-2 big takeaways Olivia has from her 5+ years at Google? How have they shaped her operating mindset today?
  • How does Olivia balance her love for analysis and data with speed and agility of decisions?

2.) Good vs Great Operations (Ops):

  • What does great ops really mean to Olivia? What are the 1-2 things founders can implement today to improve their ops immediately?
  • What are the core mistakes founders make when instilling ops for the first time?
  • How does Olivia coordinate the global Notion team to be as effective as possible?
  • What has worked? What has not worked?

3.) The Hiring Process:

  • Why does Olivia believe all leaders will have to accept they will not have all the talent they need over the coming years?
  • With that in mind, is it best to hire B players or always keep the bar high? If and when can the bar be lowered?
  • How does Olivia construct the hiring process? What are the core questions she will always ask?
  • What is the secret to great referencing? How does Olivia enable the other side to feel safe telling her everything they know about the candidate?

4.) Cross-Functional Communication:

  • How does Olivia advise founders on the best way to get different functions working together?
  • What works? What does not? What are some big mistakes Olivia sees over and over?
  • At what point in company scaling does this comms begin to breakdown?

Item’s Mentioned In Today’s Episode with Olivia Nottebohm

Grow Fast or Die Slow: The role of profitability in sustainable growth

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, 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