20VC: Andrew Wilkinson on Building The Berkshire Hathway of Tech, Sustainable vs Unsustainable Growth and The Relationship Between Money and Freedom

Andrew Wilkinson is the Managing Partner @ Tiny, a vehicle that buys, builds and invests in wonderful internet companies. Within their family of companies is Dribble; home to the world’s best design professionals; MetaLab and Supercast to name a few. Tiny does also make venture investments in the likes of Superhuman, SpaceX, Pitch and Buffer. Today Andrew oversees a group of companies with over 300 employees and tens of millions in revenue.

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In Today’s Episode You Will Learn:

1.) How Andrew made his way from founding a design agency in Canada to starting Tiny and building a family of companies with over 300 people?

2.) What does Andrew mean when he says, when buying companies he looks for companies like New Zealand? What qualities/features do they have? How does Andrew think about price sensitivity when acquiring these companies? What determines paying a premium price to Andrew?

3.) How does Andrew assess and analyse true defensibility within company strategies today? Why does Andrew not believe they will lose any companies? How does Andrew think about grow vs profitability? Are they mutually exclusive? When does one pour fuel on the fire and raise big?

4.) How has Andrew seen himself develop and change as a leader over the last 5 years? What does truly great delegation look like? What is Andrew’s biggest weakness? What is his biggest insecurity? How does Andrew think about sink the boat vs non-sink the boat decisions?

5.) Does Andrew believe we will see the unbundling of social networks moving forward? What are the core characteristics that determine whether a social network will win? Why does Dribble have defensibility as a brand against all large incumbents?

Items Mentioned In Today’s Show:

Andrew’s Fave Book: Tao of Charlie Munger: A Compilation of Quotes from Berkshire Hathaway’s Vice Chairman

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: Craft Ventures’ David Sacks on How To Assess Founder Psychology, How To Accurately Evaluate CAC, Burn and Churn & What Makes The Very Best Startup Boards

David Sacks is the Co-Founder @ Craft Ventures, one of Silicon Valley’s leading early-stage funds with David’s portfolio including the likes of Facebook, Tesla, SpaceX, Palantir, Affirm, Airbnb, Slack and Bird to name a few. David started his career in tech as the first product leader and COO @ Paypal, growing payment volume from $0-$500M per month, leading to their $1.5Bn acquisition by eBay. David then founded Geni.com, creating a family tree for the whole world, the company was acquired 3 years later by MyHeritage. David then founded Yammer, the secure solution for internal corporate communication and collaboration, acquired by Microsoft for $1.2Bn. Finally, David then became COO and Interim CEO @ Zenefits before starting Craft.

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In Today’s Episode You Will Learn:

1.) How David made his way from founding Yammer to creating one of the valley’s newest and most prestigious firms in Craft Ventures? Given David’s operating success he could have angel invested continuously, why decide to start a fund? What does he ultimately want to achieve with Craft?

2.) How did experiencing the Dot Com Bubble with Paypal and then 2008 impact David’s investing and operating mindset? Does David believe VCs really are “open for business” today? How is VC behaviour shifting when comparing early to later stage? How is Craft responding?

3.) Unit Economics: How does David assess unit economics in early-stage opportunities he is looking to invest in? What does proper attribution look like? Where do many go wrong with unit economics? Is it too early to try and assess unit econ at seed? How does David think about having mental plasticity towards unit economics, recognising how they change over time?

4.) Customer Acquisition: Does David agree with Peter Fenton, “there is a complete lack of free and open distribution”? What are the rules of thumb on CAC that David does and then does not agree with? How does David feel about blended CAC? What separates good from great when it comes to CAC/LTV?

5.) Churn: How does assess net negative churn in the businesses he works with? What is great, good, decent and poor? How does avid think about logo vs dollar retention? How does David advise founders who feel COVID has not impacted churn for them? What should they expect?

6.) Burn + Capital Efficiency: How does David analyse burn and capital efficiency today? What does he mean when he discusses “the burn multiple”? How should the burn multiple change with the stage of the business? How does David advise founders on how aggressively to cut burn today?

Items Mentioned In Today’s Show:

David’s Fave BookThucydides’ Trap

David’s Most Recently Announced Investment: Sourcegraph

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: Substack Founder Chris Best on The Future of Public Journalism, Why The Economics Of Attention Have Been Flipped & Why Micropayments For Content Will Not Work

Chris Best is the Founder & CEO @ Substack, the company that makes it simple for a writer to start a paid newsletter. To date, Chris has raised over $17M in funding from the likes of a16z, Y Combinator, Twitch CEO Emmett Shear and Zynga Co-Founder Justin Waldron to name a few. Prior to founding Substack, Chris was the Co-Founder & CTO @ Kik, letting users connect with friends, groups and the world around them. The company raised over $220M in funding from Spark, Tencent and USV to name a few.

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In Today’s Episode You Will Learn:

1.) How Chris made his way into the world of startups and came to found Kik? How his journey with Kik led to his founding Substack?

2.) During COVID, traditional media publications have been hit hard and Substack has taken off, how does Chris see the correlation there? Given the public journal of record has always been free, how does Substack interact with public news? What does Chris

3.) Why does Chris believe that micropayments are a fundamentally bad idea? Structurally why would they not work? Does Chris agree the biggest problem consumers face today in content is one of discovery? Why not?

4.) When designing the Substack product today, how does Chris think about incentive design? Why does Chris believe with incentives, Substack is the opposite of Twitter from a product perspective? Why have the “economics of attention now been flipped?”

5.) How has Chris seen himself evolve and change as a leader over the last 3 years? What advice would Chris give to CTOs making the move into the role of CEO? What does Chris believe his greatest strengths and weaknesses are as a leader? How does Chris find the war for talent today?

Items Mentioned In Today’s Show:

Chris’ Fave BookThe Death and Life of Great American Cities

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: Lightspeed Partner, Merci Victoria Grace on The Future of Collaboration Tools, Bundling vs Unbundling, Synchronous vs Asynchronous & What It Means To Productise The S*** Out of Venture

Merci Victoria Grace is a Partner @ Lightspeed Venture Partners, one of the valley’s leading venture firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Affirm, AppDynamics and more. As for Merci, prior to entering the world of venture, Merci spent 3 years at Slack including as Head of Growth where she grew the growth team to over 50 people and drove DAU’s from 500K to 5M in under 2 years. Merci is also the Founder of Women In Product a global community of incredible women in product management.

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In Today’s Episode You Will Learn:

1.) How Merci made her way into the world of venture having led the growth team at Slack for close to 3 years?

2.) Merci has been working to productise venture, so what core elements of venture need productising? What systems and tools has Merci put in place to create a product around these processes and methods? What have been the biggest challenge in the attempt to productise VC?

3.) How does the decision-making process look like at Lightspeed? How does Merci use post mortems to help her improve post having lost a deal? How does she structure those post-mortems? What have been some of the core takeaways? What internal tech stack does LSVP run itself on?

4.) How does Merci see the future of the collaboration tools market? Are we entering a period of bundling or unbundling? How does Merci feel about the debate between synchronous and asynchronous? How does Merci determine between those who have grown sustainably vs unsustainably in the time of COVID?

5.) Why do the majority of collaboration tool startups fail? What do they get so wrong in their go-to-market? For those that succeed, what are the commonalities in those that succeed? Why is being good at Twitter a competitive advantage? How does Merci feel about the Superhuman, high touch onboarding style?

Items Mentioned In Today’s Show:

Merci’s Fave BookNever Split The Difference: Negotiate As If Your Life Depended on It

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: How To Scientifically Measure Product-Market Fit, How To Efficiently and Accurately Segment Users Into Cohorts & Why Investors Analysing CAC’s at Pre-Seed Is Not Useful with Daniel Erickson, Founder & CEO @ Viable Fit

Daniel Erickson is the Founder & CEO @ Viable Fit, the startup that allows you to find product-market fit faster than ever by collecting structured user feedback to measure PMF on an ongoing basis. Daniel has raised funding from the likes of David Sacks @ Craft Ventures, Jeff Morris Jr, Todd Goldberg and Superhuman Founder, Rahul Vohra and then also Brianne Kimmel @ Worklife Ventures. Prior to founding Viable Fit, Daniel was VP Engineering @ Eaze and before that spent time as CTO @ Getable and then also had a front-row seat for the hyper-growth of Yammer with a 3-year stint there.

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In Today’s Episode You Will Learn:

1.) How Daniel made his way into the valley and startups from setting up a consultancy in Portland and how that led to founding Viable Fit?

2.) How does Daniel define product-market fit today? Why does Daniel believe it is the single most important metric for startups? What happens if you do not have product market fit? How does Daniel feel about investors spending so much time analysing unit economics at seed?

3.) What is the single most important question one can ask to determine whether you have PMF? How does customer segmentation play a role in revealing the true PMF number? How do you productise this and put it in a process? What does Daniel make of the rise of closed betas?

4.) Once they have the customer data, what elements of the data should founders double down on to determine PMF? How do they determine between feedback to adopt vs discard? Why does Daniel believe PMF is transient and you always have to measure it?

Items Mentioned In Today’s Show:

Daniel’s Fave Book: Atomic Habits by James Clear

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: It’s Time To Talk About Drinking; How To Stop, The Impact It Has, How Life Changes Post-Alcohol and The Biggest Misconceptions on Drinking with Ryan Petersen, Founder @ Flexport, Justin Kan, Founder @ Twitch, Matteo Franceschetti, Founder @ Eight Sleep & Steve Schlafman, Coach & Investor @ High Output

Ryan Petersen is the Founder & CEO @ Flexport, the operating system for global trade with over $1.3Bn in funding from the likes of Softbank, Founders Fund, DST, GV and First Round to name a few.

Justin Kan is the Founder @ Atrium and Twitch (acq by Amazon for $1Bn). Justin is also a prolific angel with a portfolio including the likes of Scale AI, Digits, Cruise and Triplebyte to name a few.

Matteo Franceschetti is the Founder & CEO @ Eight Sleep, the #1 Smart Mattress, designed to help you fall asleep faster and stay asleep. To date, Matteo has raised over $70M from Founders Fund, Khosla Ventures, Craft Ventures, Kevin Hartz and Ryan Petersen to name a few.

Steve Schlafman is a Coach and Investor @ High Output. Previously Steve was a Partner @ Primary Ventures in NYC and before that Principal @ RRE.

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In Today’s Episode You Will Learn:

1.) What was your realisation moment for stopping drinking? How did it come about? What was your prior relationship to alcohol like?

2.) For me I always found an excuse to not stop drinking, when you think about your attempts to give up, what excuses did you provide as reasons for continuing to drink? What insecurities and vulnerabilities did drinking hide and mask for you? How did it impact them?

3.) From a literal standpoint, how did you approach giving up the act of drinking? What tools did you find most helpful? What resources do you recommend? How has your life changed since you stopped drinking? Matteo, you have the data from Eight Sleep, what does the data say about how stopping drinking truly impacts your sleep?

4.) People often say that stopping drinking kills your social life, what would you respond to that commonly held belief? What other core misconceptions do you find people hold towards drinking? To those considering giving up drinking, what would you advise them? What do you know now about alcohol that you wish you had known earlier?

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: TravelPerk’s Avi Meir on Why 2021 Will Be A Record Year For Business Travel, The 3 Priorities For All Founders During COVID, What VCs Can Do To Really Support Their Founders In A Recession

Avi Meir is the Founder & CEO @ TravelPerk, the travel management platform that combines the best of leisure and corporate travel into one smooth experience. To date, Avi has raised over $134m with TravelPerk from the likes of DST, Spark Capital, Felix Capital and Heartcore to name a few. Prior to founding TravelPerk, Avi co-founded HotelNinjas, a hotel management product that was acquired by Booking.com. Before that Avi was VP Product at budgetplaces where he managed a team of 50 across product and marketing.

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In Today’s Episode You Will Learn:

1.) How Avi made his way into the world of startups and came to change the way we think of corporate travel with TravelPerk?

2.) Why has Avi advocated for the re-opening of society much sooner than others have done? If Avi were in government, what would he advocate for and do? How does Avi try and effectively assess the core risks of COVID both from a societal and economic perspective?

3.) How does Avi feel when he hears the comparison of COVID to Saars or 9/11 when it comes to their impact on travel? Why is this so different? Why does Avi believe 2021 will be a bigger year for business travel than 2019?

4.) How does Avi advise founders heavily impacted by COVID to really effectively analyse their spend and optimise runway? How does Avi think approach the element that sales and marketing is now non-revenue driving? How does Avi approach resource allocation as a result?

5.) Does Avi believe we will see a fundamental re-shaping of corporate travel? What will change? How does domestic travel change? What will the landscape look like on the other side? Who will survive? Who will thrive? Does Avi feel now is an opportune time for M&A?

Items Mentioned In Today’s Show:

Avi’s Fave Book: The Hundred-Year-Old Man Who Climbed Out of the Window and Disappeared

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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