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.
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Now displaying: February, 2022
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, 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 – streaming audio over the internet. In just four short years, (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