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: 2022
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

Jan 31, 2022

Roger Ehrenberg is a Founding Partner @ IA Ventures, one of the most successful seed funds of the last decade with $475 million across their four funds. Previous investments include The Trade Desk, Datadog, Digital Ocean, Wise and Recorded Future. Most recently, Roger took a step away from the day-to-day running of the firm, since he started IA Sports Partners, investing in sports franchises and other sports-related assets. Last month, Roger, alongside his two sons, started Eberg Capital, an investment vehicle focused on web3, crypto, NFTs and next-gen infrastructure.

In Today’s Episode with Roger Ehrenberg You Will Learn:

1.) How Roger made his way into the world of angel investing and venture having had a successful career on Wall St? How did seeing the booms and busts of the dot com and 2008 impact his investing mindset today? How does today compare to those times?

2.) The Investor Mindset:

  • What is Roger's #1 rule when it comes to managing investor psychology in volatile times?
  • What does Roger do to calm his mind and prevent worry and fear when markets crash? What works? What does not work?
  • How does one assess how close we are to the bottom? Why does Roger believe there is more "blood on the streets to come"?
  • When does Roger believe is the right time to pullback vs when to be aggressive in deployment?
  • What company profiles will do well vs poorly moving into this new cycle?

3.) Investing Strategy:

  • How does this new market impact the three different investing categories; early, Series A & B and growth?
  • Why does Roger believe deployment timelines will be extended? How will pricing be impacted?
  • Why does Roger believe that the Series A & B crunch is the most worrisome? How will their bar for what makes a great company change?
  • Should early stage managers alter their reserves strategy in the face of more stringent Series A rounds? Why does it not make sense to invest in "pay to play" rounds?
  • How does Roger adivse the companies that he works with today on burn vs growth?

4.) AMA:

  • How does Roger evaluate his own relationship to money today? How has it changed over time?
  • What does Roger believes makes a truly successful marriage? What can one do to foster extreme trust and safety in a marriage?
  • What does Roger believe have been some of the biggest insecurities he has had to overcome over the last decade? How did he overcome them?

Item’s Mentioned In Today’s Episode with Roger Ehrenberg

RIP Good Times by Sequoia Capital

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, 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?

Jan 17, 2022

Frank Slootman currently serves as Chairman and CEO at Snowflake and has over 25 years of experience as an entrepreneur and executive in the enterprise software industry. Prior to Snowflake, Frank served as CEO and President of ServiceNow taking the company from around $100M in revenue, through an IPO, to $1.4B. Before ServiceNow, Frank served as President of the Backup Recovery Systems Division at EMC following the acquisition of Data Domain Corporation/Data Domain, Inc., where he served as the CEO and President, leading the company through an IPO to its acquisition by EMC for $2.4B. You must check out Frank's book, Amp It Up. It can already be pre-ordered here.

In Today’s Episode with Frank Slootman You Will Learn:

1.) Narrow the Focus, Increase the Quality:

  • How does Frank determine what to focus on? What does the prioritisation process look like?
  • What one question does Frank ask his team to ensure they are focused?
  • What are the best answers? What are the worst? When should you change focus?

2.) When There is Doubt, There is No Doubt:

  • What does Frank mean by this? What does it apply to? When is there nuance?
  • How long does Frank give people who are underperforming? How does he communicate their underperformance to them directly but productively?
  • What is the right way to fire someone? Why are performance reviews BS?

3.) Make The Good People Great:

  • How does Frank get the very best out of his teams? How does he make the good great?
  • How does he use compensation and equity structures to supercharge his teams?
  • How does Frank set stretch targets that are both ambitious but also attainable?

4.) The Art of Leadership and Board Management:

  • Why does Frank believe every CEO should be anxious?
  • How has Frank changed as a leader over time?
  • What is the biggest mistake founders make when it comes to board management?
  • How can founders actively manage and control their board?

Item’s Mentioned In Today’s Episode with Frank Slootman

Frank’s Favourite Book: Courage Is Calling: Fortune Favours the Brave, The Speed of Trust: The One Thing that Changes Everything

Jan 14, 2022

Devin Finzer is the Founder & CEO @ Opensea, the world's first and largest NFT marketplace allowing you to discover, collect, and sell extraordinary NFTs. To date, Devin has raised over $423M for the company with their last $300M round valuing Opensea at $13.3BN. Before changing the world of NFTs, Devin co-founded ClaimDog which was acquired by Credit Karma and before founding ClaimDog, Devin was an engineer at Pinterest. Do want to say, I always love Semil Shah's startup of the year, for 2021 it was Opensea, check out his piece here.

In Today’s Episode with Devin Finzer You Will Learn:

1.) How Devin made his way into the world of NFTs and came to found the first and largest NFT marketplace in the form of Opensea?

2.) The Scaling Story:

  • What were the first early signs that Opensea was working when they were in YC? What core metrics did they look at to determine success?
  • Given NFTs not being "hot" at the time, how was the fundraising process for Opensea coming out of YC? What were the early investors most excited about?
  • What was the inflection point when Opensea and NFTs really started to take off? What most surprised Devin about the way in which the inflection point happened?
  • When scaling from $150M to $4BN in GMV, what are the first things to break in a company?
  • How does Devin maintain company morale with such volatile crypto and NFT markets?

3.) The Next Decade of NFTs:

  • How does Devin predict large brands and companies will utilise NFTs for their businesses?
  • In what ways does Devin think creators and celebrities will use NFTs moving forward to create more efficient business models?
  • How does Devin respond to the statement, "NFTs do more to harm than help income inequality?"
  • What are Devin's biggest concerns moving forward when analysing the NFT market?
  • How does Devin see the future for the development and experimentation of NFTs?

4.) The Future of NFT & Gaming:

  • How does Devin see NFTs impacting the world of gaming most?
  • How does Devin think about interacting with these gaming communities that are external to the centralised Opensea marketplace?

Item’s Mentioned In Today’s Episode with Devin Finzer

Devin’s Favourite Book: Homo Deus: A Brief History of Tomorrow

Jan 12, 2022

Ralf Wenzel is the Founder & CEO @ JOKR, a global platform for instant retail delivery at a hyper-local scale serving both the US and LATAM. Ralf has raised over $260M for the company, most recently valuing it at $1.2BN. Prior to JOKR, Ralf spent 7 years as the Founder & CEO @ foodpanda, as well as, enjoying roles as Chief Strategy Officer @ Delivery Hero, Interim Chief Product and Experience Officer @ WeWork and even moving to the other side of the table as a Managing Partner with Softbank.

In Today’s Episode with Ralf Wenzel You Will Learn:

1.) What is the unit economic breakdown for quick commerce business models? What levers can be used to improve it over time?

2.) Comparing the US to LATAM:

  • What is the AOV (average order value) in the US vs LATAM?
  • What is the order frequency in the US vs LATAM?
  • How does labour cost vary when comparing LATAM to the US?
  • How does real estate cost for fulfilment centres differ when comparing LATAM to the US?
  • How do product margins on a per product basis differ when comparing US to LATAM?

3.) New Market Growth and Maturation:

  • What is the payback period for new markets? How has this changed over time?
  • How does the payback period reduce with every new market being opened?
  • What % of AOV is spent on marketing when a new market is opened? How does this marketing spend change over time?
  • In mature markets, how much new customer acquisition is organic vs paid?
  • What is the average weekly growth rate in new vs mature markets?

4.) Business Model Expansions:

  • How does Ralf and JOKR approach the potential for private label goods?
  • How does private label change the margin structure of the goods?
  • What have been their lessons from starting their first private label goods?
  • How does Ralf approach the ability to integrate advertising and paid search?
  • What is needed for paid search and advertising to be a meaningful part of the business?

Jan 10, 2022

Mark Carney is Vice Chair of Brookfield Asset Management and Head of Transition Investing. Prior to Brookfield, Mark served as the Governor of the Bank of England from 2013 to 2020, and prior to that as Governor of the Bank of Canada from 2008 until 2013. Mark was also Chairman of the Financial Stability Board from 2011 to 2018. Mark is a long-time and well-known advocate for sustainability and is currently the United Nations Special Envoy for Climate Action and Finance. If that was not enough, Mark serves on numerous other boards including Stripe, Bloomberg Philanthropies and the Foundation Board of the World Economic Forum to name a few.

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

1.) How Mark made his entrance into the world of finance and came to the role of Governor of the Bank of Canada? How did that role lead to his becoming Governor of the Bank of England? How did seeing multiple booms and busts impact Mark's investing mindset?

2.) Governments, Central Banks and Regulation:

  • How do governments and central banks retain control in a completely decentralized financial world?
  • Can traditional currencies and digital currencies peacefully co-exist?
  • What are Mark's predictions for central bank digital currencies?
  • How does Mark expect governments and central banks to regulate digital currencies in the coming years?

3.) The Winners and Losers:

  • What does the future hold for crypto exchanges?
  • How do competitors for digital gold perform?
  • Why does Mark believe in crypto "only the niche will survive"?
  • What does the rise of Defi mean for traditional banks? What will determine those that survive?
  • What does Mark mean when he says the winners will decide "what is my interface with this crypto world?''

4.) The Future of NFTs:

  • Do NFTs do more to help or to harm income inequality?
  • How does Mark see the future for the development and experimentation of NFTs?
  • Who are the winners and losers in the next decade for NFTs?
  • How does Mark feel about the pause between productivity gains and real wage benefits that exist today? 

Item’s Mentioned In Today’s Episode with Mark Carney

Mark’s Favourite Book: Arcadia by Tom Stoppard

Jan 5, 2022

Will Ahmed is the Founder and CEO @ Whoop, the company on a mission to unlock human performance with their wearable device that is your digital fitness and health coach. To date, Will has raised over $400M for the company with the last round valuing Whoop at $3.6BN and with a cap table including the likes of Softbank, Accomplice, Founder Collective, Foundry Group, IVP and more.

In Today’s Episode with Will Ahmed You Will Learn:

1.) How Will went from being a professional athlete and college student to founding one of the hottest startups in fitness and healthcare? What are the similarities and differences of being an athlete and being a CEO?

2.) What does Will mean when he says, "there is value in the struggle early on"? How does Will advise founders on when to give up vs when to stay the course? If Will had not struggled with funding in the early days, would the Whoop journey be different? How does Will advise founders when it comes to taking funding when it is on the table? What are the nuances to this?

3.) In what way does Will believe "realism is overrated"? When does Will believe it is good to be realistic? In what ways can it be good to be idealistic? How did Will get some of the largest sports stars on the planet to use Whoop in the early days? Why did Will always refuse to pay sports stars to use Whoop? What were the benefits of doing this?

4.) How does Will define high performance? Why does Will believe it is crucial for leaders to disassociate their own personal feelings from the progress of their company? What advice does Will give to leaders in an attempt to do this? What has Will done to be a better CEO in the last year? What does Will believe are his biggest weaknesses as a CEO? 

Item’s Mentioned In Today’s Episode with Will Ahmed

Will’s Favourite Book: Shoe Dog: A Memoir by the Creator of NIKE

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