20VC: Evernote & mmhmm Founder Phil Libin on Why We are Beginning a Multi-Trillion Dollar Restructuring of the World, Why Shortcuts are the Biggest Mistakes Startups Make & The Future of Video and The Unbundling of Zoom

Phil Libin is the Founder and CEO @ mmhmm, the app that allows you to level up your remote presentations, making high-quality video content in minutes. To date, Phil has raised over $30M for the company from an incredible investor base including Sequoia, Kevin & Julia Hartz, Tony Fadell, Instagram’s Kevin Systrom and Mike Krieger and Brianne Kimmel. Prior to mmhmm, Phil was a Managing Director @ General Catalyst and prior to his time in venture, Phil most famously founded Evernote, where he led the business with phenomenal success, as CEO for over 8 years.

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In Today’s Episode You Will Learn:

1.) How Phil made his way into the world of startups, came to found Evernote and how that led to his founding of mmhmm, most recently?

2.) How would Phil describe his management style today? How has it changed over time? Why does Phil believe shortcuts are the greatest mistakes startups make? What does Phil believe you can vs cannot take shortcuts on? What have been some real world lessons there?

3.) What were Phil’s biggest takeaways from his time in venture? How did it change his operating mindset? Does Phil believe there is an incentive misalignment between founder and VC? Why is Roelof Botha the best board member Phil has worked with? What makes him so special?

4.) How does Phil think about the unbundling/verticalisation of Zoom? How does he predict the market evolving? How does Phil see the differing usage patterns between consumer and business? Why does Phil believe more can be learned from looking at similarities and not differences?

5.) What does Phil believe are the two classes of mistakes when scaling startups? What have been Phil’s biggest lessons on acquiring and retaining the best talent? How does Phil create an environment of dissent where anyone can bring their entire self and beliefs to the table?

Item’s Mentioned In Today’s Episode

Phil’s Favourite Book: Kafka on the Shore

As always you can follow Harry and The Twenty Minute VC on Twitter here!

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20VC: Hims Founder Andrew Dudum on Hims Going Public, The Reasoning and Benefits of SPACs, The Biggest Misconceptions of Successful Company Building & Wall St’s Changing Perceptions Towards Growth and Profitability

Andrew Dudum is the Founder & CEO @ Hims & Hers, offering a modern approach to health and wellness and one of the fastest-growing companies to reach $1Bn. Prior to their going public on Tuesday this week, Hims raised over $158M from some of the best including Thrive, Forerunner, Founders Fund, IVP, Redpoint and more. As for Andrew, alongside his role at Hims he is also Co-Founder of Atomic, a company builder and venture fund all in one, backed by Peter Thiel and Marc Andreesen to name two. Prior to Atomic, Andrew led product at TokBox managing a team of 30 leading to their acquisition by Telefonica in 2012.

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In Today’s Episode You Will Learn:

1.) How Andrew made his way from Head of Product at Tokbox to venture capitalist with Atomic to changing healthcare with Hims?

2.) What are the biggest misconceptions people have with regards to what it takes to build a successful company? Why do you not need big teams? How can leaders drive efficiency within small teams? What have been Andrew’s biggest lessons in acquiring the best talent in market? What works?

3.) Hims is the fastest company to scale to $1Bn, how does Andrew reflect on how he managed hyper-growth? What did he do well? What was the first to break? What would he do differently? When is the right time to go from generalist to specialist? When is the right time to add more products?

4.) Why did Andrew believe now was the right time to IPO just 4 years into the founding of the business? How did the SPAC process play out? What are the core advantages to Andrew of the SPAC over an IPO? Why will more founders use it in the future? How does Andrew assess the importance or lack of, when it comes to the pricing pop on IPO day?

5.) How does Andrew reflect on his relationship to money? Why does he feel more scared of it now than ever before? How does he think about bringing up his children with an appreciation and respect for money? What 3 traits would Andrew most like his children to have?

Item’s Mentioned In Today’s Episode

Andrew’s Favourite Book: The Planet Remade: How Geoengineering Could Change the World

As always you can follow Harry and The Twenty Minute VC on Twitter here!

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20VC: Etsy CEO, Josh Silverman on 2 Defining Traits of Great Leadership, The Danger of Attaching Happiness To Milestones, How To Structure Teams To Optimise for Experimentation and Agility &Whether You Learn More From Success Than Failure

Josh Silverman is the CEO @ Etsy, leading the company as it builds a platform that empowers creative entrepreneurs around the world. Prior to their IPO, Etsy raised funding from some of the best in the business including Danny Rimer @ Index, Albert Wenger @ USV and Jim Breyer @ Accel to name a few. Prior to Etsy, Josh served as President of Consumer Products and Services at American Express, was the CEO of Skype, and CEO of shopping.com, and he held various executive roles at eBay. Josh is also currently on the board of directors of Shake Shack.

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In Today’s Episode You Will Learn:

1.) How Josh made his entry into the world of startups, came to be CEO of Skype and how he came to be CEO of Etsy? How did Josh’s political background prepare him for being a public markets CEO?

2.) How does Josh think about 10 year plans? What is the right alternative? What does Josh do when he does not know what to do? How does Josh think about head vs heart in decision-making? How does Josh think about downside protection and risk mitigation with decisions?

3.) Why does Josh believe that you should, “never let a crisis go to waste”? How does he interpret that? Does Josh believe you learn more from success than failure? Why does Josh believe many succeed in spite of, not because of? How does Josh connote happiness to a milestone of success? What is true happiness for Josh?

4.) How does Josh think about winning today? What is the framework Josh believes founders need to put in place to optimise their chance of winning? How does Josh structure his team at Etsy to optimise for speed and experimentation? What has worked? What has not worked?

5.) How can leaders create a system where failure is minimised? How does Josh implement a “red hat vs green hat” decision making process around new ideas at Etsy? What question does Josh and the team ask with every experiment? How should one analyse the cost of rolling back a decision?

6.) How does Josh determine between dogma and good practice in a company? What is the right way to remove antiquated dogma without damaging morale? What were some of the biggest challenges from his doing this on entry at Etsy?

Item’s Mentioned In Today’s Episode

Josh’s Favourite Book: Grant

As always you can follow Harry and The Twenty Minute VC on Twitter here!

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20VC: Databricks CEO, Ali Ghodsi on The 3 Phases of Startup Growth, How to Evaluate Risk and Downside Scenario Planning & Who, What and When To Hire When Scaling Your Go-To-Market

Ali Ghodsi is the Founder & CEO @ Databricks, bringing together data engineering, science and analytics on an open, unified platform so data teams can collaborate and innovate faster. To date, Ali has raised over $897M for the company including from the likes of a16z, NEA, Microsoft, Battery, Coatue, Greenbay and more. Prior to Databricks, Ali was one of the original creators of open source project, Apache Spark, and ideas from his research have been applied to Apache Mesos and Apache Hadoop.

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In Today’s Episode You Will Learn:

1.) How Ali made his way from fleeing Iran as a refugee to living in a Swedish ghetto? What was the founding moment for Ali with Databricks?

2.) How does Ali think about and evaluate risk today? Why does Ali always make his team do downside scenario planning? How does Ali think about his relationship to money today? Why does Ali disagree with gut decisions? What is his process for making decisions effectively?

3.) Stage 1: The Search for PMF: What are the core elements included in this phase? What types of leaders thrive in this phase? What type struggle? How can leaders sustain morale in the early days when it is not up and to the right? Who are the crucial hires in this phase?

4.) Stage 2: Scale Go-To-Market: What are the core roles needed to expand GTM fast and effectively? Why should you hire sales leaders before marketing leaders? Why is hiring finance leaders so crucial here? What mistakes are most often made here? How do the board resolve them?

5.) Stage 3: Process and Efficiency: What are the first and most important processes that need to be implemented? How does Ali need to change the type of leader he is to fit this stage? How does one retain creativity and nimble decision-making at scale and with process?

Item’s Mentioned In Today’s Episode

Ali’s Favourite Book: Good Strategy Bad Strategy: The Difference and Why it Matters

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC: Annie Duke on Reversible vs Irreversible Decisions, How To Evaluate Risk, The Theory of Sunk Cost in Venture & How to Optimise Both the Discussion and Quality of Investment Decisions

Annie Duke is a former professional poker player and the author of National Bestseller, “Thinking in Bets” & “How To Decide”. During her poker playing days, Annie was a World Series of Poker bracelet winner, the winner of the 2004 Tournament of Champions and the only woman to win the NBC National Poker Heads Up Championship. Today, Annie is also the founder of How I Decide, a non-profit that creates curricula and tools to improve decision making and critical thinking skills for under-served middle schoolers.

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In Today’s Episode You Will Learn:

1.) How Annie made her way from professional poker player to National Bestselling author and coach to the world’s leading investors?

2.) How does Annie evaluate the nature of risk? What is good risk vs bad risk? How does Annie think through reversible vs irreversible decisions? What is her framework? Why does Annie believe most irreversible decisions are actually reversible? How does it change your thinking?

3.) How does effective solo-decision-making differ from effective group decision-making? What decision-making biases does Annie often see venture being guilty of making? What 3 things can one do to improve the decision-making of the collective group?

4.) How does Annie think about sunk cost? How does one know when enough is enough and you have to walk away? How does this tie into Annie’s thinking on portfolio theory? How does Annie think about pre-mortems? How should they be structured? What is included?

5.) How does Annie define critical thinking? What tips would Annie give to someone in really advancing their level of critical thinking? What behaviours can one implement to seek to protect critical thinking? How does this differ in team environments?

Item’s Mentioned In Today’s Episode

Annie’s Favourite Book: The Success Equation: Untangling Skill and Luck in Business, Sports, and Investing

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

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