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.
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!
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.
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 Book: Thucydides’ Trap
David's Most Recently Announced Investment: Sourcegraph
As always you can follow Harry and The Twenty Minute VC on Twitter here!
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.
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 Book: The Death and Life of Great American Cities
As always you can follow Harry and The Twenty Minute VC on Twitter here!
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.
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 Book: Never 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!
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, 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.
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!
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.
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!
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.
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:
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Elad Gil is one of Silicon Valley's most successful and prominent angels of the last decade with a portfolio including the likes of Stripe, Square, Airbnb, Pinterest, Instacart, Flexport and Brex to name a few. Prior to solely company investing, Elad was an operator as Founder and CEO @ Color Genomics for their first 3 years. Before Color, Elad was a VP of Corporate Strategy @ Twitter following their acquisition of the company he founded, Mixer Labs. Before founding Mixer, Elad spent 3 years at Google where he was involved with 3 acquisition including the Android acquisition.
In Today’s Episode You Will Learn:
1.) How Elad made his way into the world of startups and how that led to his investing in some of the most prominent companies of the last decade?
2.) How is the venture and startup landscape shifting right now? What does Elad make of the large multi-stage funds re-entering seed? How does Elad advise founders when it comes to taking secondaries?
3.) What are the core elements startups need to assess to fully understand their cash position? What is the optimal runway to have and to raise for today? How can founders stress test their runway models? Where does Elad see the most mistakes when it comes to runway?
4.) Does Elad believe the VC messages of "Open for Business" during COVID? How does Elad advise founders when it comes to valuation sensitivity today? What are the core terms that founders should watch out for when raising? How does Elad see venture fund reserve allocations changing?
5.) What are the core tenets of an effective layoff strategy? How should they determine the right level of aggression with which to make cuts? How can layoffs be done in a way that maintains internal culture and morale? Where does Elad see many going wrong when it comes to layoffs?
6.) Which business will thrive in COVID times? Which will die? What are the leading indicators of each? How does Elad determine in the businesses that are growing immensely during COVID, those that are sustainable growth and those which are purely due to COVID?
Items Mentioned In Today’s Show:
Elad’s Fave Book: Master of the Senate: The Years of Lyndon Johnson
Elad’s Most Recent Investment: Deel
As always you can follow Harry, The Twenty Minute VC and Elad and on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Ariel Cohen is the Founder & CEO @ TripActions, the company trusted by more than 4,000 companies to manage their business travel and expenses. To date, Ariel has raised more than $980M with TripActions from the likes of Lightspeed, Oren Zeev and a16z to name a few. Prior to TripActions, Ariel co-founded StreamOnce, a business multimedia integration platform which was acquired by Jive Software. Prior to StreamOnce, Ariel led Product Management in a senior leadership role at Hewlett-Packard.
In Today’s Episode You Will Learn:
1.) How Ariel made his way into the world of tech and came to change the way we think about business travel today with TripActions?
2.) What are TripActions doing in their business to be there for their partners, customers and suppliers in the long term? TripActions engaged in layoffs, how did Ariel approach the size of layoff required? What is the right way to do layoffs? How does this change in a remote world?
3.) Given the uncertainty, how does Ariel advise founders to assess and correct their burn and spending? What is a reasonable amount of runway to reserve for? For those hit hard on the demand side, what can they do to build durable defensibility when they can't scale demand?
4.) How does Ariel view the future of business travel? Does Zoom replace much of the business trips? What will the landscape look like in 3 years? What players will survive? Who will thrive?
5.) From a founder psychology perspective, what has Avi done to cope in these very challenging times? What has worked? What has not worked? What does Ariel advise founders struggling to cope psychologically? What can investors do to be there for their founders?
Items Mentioned In Today’s Show:
Ariel’s Fave Book: Mr Vertigo
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Hamilton Helmer is the Managing Partner & Chief Investment Officer @ Strategy Capital a long-only public equity fund that selects securities for investment based on Power Dynamics, a proprietary model of fundamental value, developed by Hamilton over decades of strategy consulting with clients such as Hewlett-Packard, Adobe and more. Hamilton is also the author of one of my favourite books, 7 Powers. If that was not enough, Hamilton is also an Instructor in the Economics Department @ Stanford University.
In Today’s Episode You Will Learn:
1.) How Hamilton made his way into the world of investing from advising some of the largest tech titans on the planet with Adobe and HP?
2.) What is a strategy mental model? What makes the most effective strategic models? What characteristics do they have? How should founders balance between sticking to models and being willing to change them? What are Hamilton's biggest takeaways from working with Netflix?
3.) "All strategy begins with invention", what did Hamilton mean by this? How does Hamilton explain the success of copycats in markets? How does Hamilton separate between first mover and creator? How does Hamilton analyse the transition from startup to pricer with scale economics?
4.) How does Hamilton advise founders to view and approach competition? Why does Hamilton totally disagree with the requirement of being 10x better than your competition? Is product innovation alone enough without brand or business model innovation?
5.) How does Hamilton define "brand"? Is brand an attainable strategy alone or is it the byproduct of something else? How transferable is brand in one category to alternative categories? How does a brand truly know when they have sustainable leverage and power?
Items Mentioned In Today’s Show:
Hamilton’s Fave Book: The Road to Reality: A Complete Guide to the Laws of the Universe, Stardust
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Sarah Kunst is the Founder and Managing Director @ Cleo Capital with a portfolio including the likes of StyleSeat, Glow Bar and PlateJoy to name a few. Prior to venture, Sarah served as a senior advisor at Bumble where she focused on their corporate VC arm, Bumble Fund, and on the board of the Michigan State University Foundation endowment. If that was not enough, Sarah is also a contributing editor @ Vanity Fair. Due to her success, Sarah has been named a Future Innovator by Vanity Fair and a top woman in VC by Wall St Journal.
In Today’s Episode You Will Learn:
1.) How Sarah made her way into the world of venture from Bumble and how that led to her founding Cleo Capital?
2.) Does Sarah believe VCs really are still "open for business"? What does Sarah make of all the dry powder sitting on the sidelines? How does Sarah think reserve allocation strategies will change today? Why does Sarah believe another great vintage of funds is to come, as it did in 08'?
3.) What would Sarah most like to change about the world of venture? Does Sarah agree that GP commit expectations prevent diversity in venture? How was the fundraising process for Sarah? How can VCs prove skin in the game without having personal capital?
4.) What is the #1 piece of advice Sarah is giving her founders in these COVID times? How does Sarah advise her founders on approaching the talent market today? How does Sarah advise her founders on burn and capital allocation given COVID?
Items Mentioned In Today’s Show:
Sarah’s Fave Book: Attached: Are you Anxious, Avoidant or Secure? How the science of adult attachment can help you find – and keep
Sarah’s Most Recent Investment: Planet Forward
As always you can follow Harry, The Twenty Minute VC and Sarah and on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Mike Maples is a Founder & Partner @ Floodgate, one of the leading early-stage firms of the last decade with investments in the likes of Lyft, Twitch, Twitter, Okta and Sonos to name a few. He has been on the Forbes Midas List since 2010 and was also named one of “8 Rising Stars” by FORTUNE Magazine. Before becoming a full-time investor, Mike was involved as a founder and operating executive at back-to-back startup IPOs, including Tivoli Systems (IPO TIVS, acquired by IBM) and Motive (IPO MOTV, acquired by Alcatel-Lucent.)
In Today’s Episode You Will Learn:
1.) How Mike made his way from founding startups to entering the world of venture and the gap he saw in the market when founding Floodgate?
2.) Mike has previously said, "a startup is not a company, it is a series of breakthroughs". How does Mike define a breakthrough? What are the 2 most meaningful breakthroughs a startup can experience? Which excites Mike the most to see? How do the best startups scale pre-breakthrough to post-breakthrough?
3.) What are the core ways inflections can create breakthrough opportunities? What were Mike's learnings on inflections from investing in Lyft? What does Mike mean when he talks about the importance of "backcasting"? What did investing in Twitch teach Mike about forecasting?
4.) How does Mike feel about the rise of operator and angel funds? How does Mike analyse the re-entrance of large multi-stage funds back into seed markets? Does Mike agree with Semil Shah, "founders are voting with their feet and taking multi-stage money at seed"?
5.) As Mike's peers have all moved into larger funds, Mike did not, why? How does Mike view "fund size as your strategy"? How does Mike think about the centrality of ownership? Does Mike really believe you can concentrate capital into your winners? What are the challenges? Why does Mike feel self-promotion is one of the biggest challenges in VC?
Items Mentioned In Today’s Show:
Mike’s Fave Book: Superforecasting: The Art and Science of Prediction
Mike’s Most Recent Investment: CommonStock
As always you can follow Harry, The Twenty Minute VC and Mike and on Twitter here!
Conor White-Sullivan is the Founder & CEO @ Roam Research, the tool taking over our industry providing a seamless note-taking tool for networked thought. Prior to founding Roam, Conor founded 2 prior businesses and also worked at HuffPost as a Co-Founder of HuffPost Labs where he reported directly to Arianna Huffington and HuffPost CTO.
In Today’s Episode You Will Learn:
1.) How Conor's high school wrestling career taught him "how to win"? What was the founding story with Roam? How does Conor think about when to stay true to the vision and persist vs when to give up?
2.) How does Conor think about the product design philosophy they have @ Roam? Conor has said before, "Roam is not about taking better notes", what is Roam about then? How does Conor think about the importance of adding challenge to a product? What does he mean when he discusses the importance of "low floors and high ceilings" with regards to product design?
3.) How would Conor analyse his own hiring and team-building philosophy? Why are the two most important traits, "girt and autodidacts"?How does Conor really stress these two characteristics in an interview process? Why does Conor choose to live with the team? What are the benefits of this?
4.) Does Conor believe we are in a phase of bundling or unbundling when it comes to collaboration tools? Does Conor believe we will see large players acquire and consolidate over the coming months? Why does Conor compare Roam more to Google than other collaboration tools?
5.) How does Conor think about go-to-market today? What were some of Conor's biggest takeaways for bootstrapping for years with revenue from customers? Why is Conor borrowing from the Tesla GTM? What does that really mean in practice?
Items Mentioned In Today’s Show:
Conor’s Fave Book: How to Read a Book: The Classic Guide to Intelligent Reading
As always you can follow Harry, The Twenty Minute VC and Conor and on Twitter here!
Mark Cuban is a serial entrepreneur, investor, and owner of the Dallas Mavericks. His career began with his founding of MicroSolutions, a company he went on to sell to CompuServe in 1990. Then in 1995 Mark co-founded Broadcast.com - streaming audio over the internet. In just four short years, Broadcast.com (then Audionet) was sold to Yahoo for $5.6 billion dollars. Following the acquisition in 2000, Mark acquired the Dallas Mavericks where since his taking over they have competed in the NBA Finals for the first time in franchise history in 2006 - and becoming NBA World Champions in 2011. They are currently listed as one of Forbes' most valuable franchises in sports. If that was not enough, Mark is also one of ABC's "Sharks" on the hit show Shark Tank.
In Today’s Episode You Will Learn:
1.) How Mark made his way into the world of technology and startups having been fired from his first job in sales?
2.) How does Mark evaluate his relationship to wealth and money? How has that changed over time? What advice does Mark have to those that tie happiness and money together?
3.) What does Mark think about Silicon Valley investors today? Why does he believe they and the valley are like Hollywood? Why does Mark believe that if the greatest tech companies of today had been started elsewhere, they would be more successful?
4.) How does Mark evaluate his own investing philosophy today? How does Mark think about price and price sensitivity? Why is Mark so keen to have his investment funded from the cashflow of the business? Does this not narrow opportunity and limit upside? How does Mark evaluate risk today?
5.) Why does Mark believe post-COVID is the single greatest time to be an entrepreneur? What advice would he give to an entrepreneur starting their new business in this time? How would Mark go about the re-opening of society post lockdown?
Items Mentioned In Today’s Show:
Mark’s Fave Book: Rebooting AI: Building Artificial Intelligence We Can Trust, Healthy Buildings: How Indoor Spaces Drive Performance and Productivity
As always you can follow Harry, The Twenty Minute VC and Mark and on Twitter here!
Wayne Chang and Jeff Seibert are the co-founders @ Digits, the company that gives you a complete, real-time understanding of your expenses, all in just a few clicks. To date, Wayne and Jeff have raised over $32M for Digits from some of the best in the business including Peter Fenton @ Benchmark and Jess Verrilli @ GV and then with the most incredible base of angels with the founders from Box, Github, Stitch Fix, Tinder, Gusto and more. Prior to Digits, Wayne and Jeff co-founded Crashlytics, acquired by Twitter for a 9-figure sum in Jan 2013 and then acquired from Twitter by Google in 2017. If that was not enough they are also LPs in some of the world's most exclusive funds and angels in the likes of Gusto, OpenDoor and SoFi to name a few.
In Today’s Episode You Will Learn:
1.) How did Jeff and Wayne make their way into the world of tech and startups? How did Wayne crashing a startup dinner start everything for them?
2.) How did Jeff and Wayne's prior success with Crashlytics impact their operating mindset scaling Digits today? What worked? What did not work? What gets easier with time? What gets harder the second time around?
3.) What have been Wayne and Jeff's biggest lessons from having a remote team from Day 1? What structure and framework do they use to hire the best remote talent? How does that change at the exec level? How do they think about optimising product management for remote teams?
4.) How would Wayne and Jeff summarise their design philosophy with Digits? Why does Wayne believe "minimalism only favours the designer"? When does it make sense to actually add some complexity to your product?
5.) Digits raised $33M pre-launch, why did they favour this approach? How do they think about when to transition from lean and iterative to aggressive and pouring fuel on the fire? Why did they choose to work with Peter Fenton? How do they think about optimising their angel network?
Items Mentioned In Today’s Show:
Wayne’s Fave Book: Enders Game
Jeff's Fave Book: Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Howie Liu is the Founder & CEO @ Airtable, the all in one collaboration platform that has taken so much of our ecosystem by storm. To date, Howie has raised over $170M from some of the best in the business including Benchmark, Thrive, Coatue, Caffeinated Capital, Founder Collective, CRV and Freestyle to name a few. Prior to founding Airtable, Howie was the Co-Founder @ Etacts, an automated intelligent CRM that was acquired by Salesforce just 9 months after creation. Howie then led the social CRM product at Salesforce. Fun fact, Howie started his career as an intern at Freestyle Ventures.
In Today’s Episode You Will Learn:
1.) How Howie made his way from founding Etacts to changing the way we think about databases and spreadsheets today with Airtable? How did Salesforce acquiring Etacts impact Howie's operating mentality with Airtable?
2.) With the rise of remote work, what have been Howie's core observations from the last month of the world going WFH? What does it take to succeed? What mistakes have Airtable made in their process of work from home? Why did it not work? What lessons did Howie take from that?
3.) How does Howie think about Airtable's transition from an application to a platform? What does he perceive as the core challenges in making the transition? What lessons has he learned from studying others who have done it? Why did Howie choose Peter Fenton @ Benchmark to work with?
4.) How has Howie seen himself evolve and scale as a leader over the last few years? What have been the most challenging elements? How does Howie think about which individuals he would like as mentors? How does he determine which advice to ingest vs to reject?
5.) How does Howie analyse the remote work/collaboration tools environment today? Does Howie believe we will enter a period of consolidation with the proliferation of new tools created? Does Howie believe we will see an unbundling in collaboration tools?
Items Mentioned In Today’s Show:
Howie’s Fave Book: Hard Drive: Bill Gates and the Making of the Microsoft Empire, Spying on Whales
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Rahul Vohra is the Founder & CEO @ Superhuman, the startup that has rebuilt the inbox from the ground up creating the fastest email experience ever made. To date, Rahul has raised over $56m with Superhuman from some of the best in the business including a16z, First Round, Box Group and then 2 of my favourites in Jeff Morris Jr @ Chapter One and Ed and Elliot @ Boldstart. Prior to founding Superhuman, Rahul was the Founder @ Rapportive, a company later acquired by LinkedIn in 2014. If that was not enough, Rahul is also an investor having co-founded a new firm with Todd Goldberg just last year.
In Today’s Episode You Will Learn:
1.) How Rahul made his way from making the first plugin for Gmail with Rapportive to changing how we think about email today with Superhuman?
2.) Why does Rahul believe game design is worth doing? What is the difference between game design and gamification? What does it take to create a game? What is the truth on game design?
3.) What are the core 5 factors that make up effective game design? How can products incorporate goals to make the user feel emotion when engaging? What emotions does one want the user to feel? How can they be tested? What controls should be placed around the UX? Why are controls so fundamental?
4.) What is the difference between a toy and a game? How can one effectively incorporate toys into their product? How has Superhuman done this effectively to date? Hw can designers create a system of flow in the user experience? What works? What does not work?
5.) Did Rahul intentionally create an entirely new category when it comes to onboarding? Why does Rahul pushback on people that suggest 1-1 onboarding is not scalable? What does the unit economics look like? How does this scale to $100M ARR?
Items Mentioned In Today’s Show:
Rahul’s Fave Book: The Art of Game Design: A book of lenses
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.
Mark Suster is the Managing Partner @ Upfront Ventures, one of LA's leading and largest venture firms with a portfolio including the likes of Bird, GOAT, Maker Studios and Ring.com to name a few. Prior to joining the world of venture, Mark was the founder & CEO of two successful enterprise software companies, the most recent of which was sold to Salesforce.com where Mark became VP, Products. Mark is also the author of one of my favourite industry blogs, Both Sides of The Table.
In Today’s Episode You Will Learn:
1.) How Mark made his way from founding enterprise companies to joining "the dark side" of venture with his move to Upfront?
2.) How does the current economic landscape change the world of B2B? How will renewals be impacted? How will customers approach discounting? Similarly, how will the world of B2C be impacted by COVID? How does this impact marketing and ad spend?
3.) How does Mark think about reserve allocation today with Upfront? How does that change in the face of COVID? Why does Mark believe this environment will redefine valuations? How should founders respond in the face of heavily changed valuations?
4.) Does Mark believe we will see a graveyard of new venture firms who have deployed too quickly and have too many hungry mouths to feed? How does Mark think about building temporal diversification into the portfolio? How can managers use reserves more intelligently moving forward?
5.) Does Mark agree with the Twittersphere that VCs remain "open for business"? How will we see deal volume impact? How will we see size of transaction impacted? What is the most important role a VC can play today? How will the M&A market also be impacte din the face of COVID?
Items Mentioned In Today’s Show:
Mark’s Fave Book: Disunited Nations: The Scramble for Power in an Ungoverned World
Mark's Most Recent Investment: Solve
As always you can follow Harry, The Twenty Minute VC and Mark and on Twitter here!
Sarah Cannon is a Partner @ Index Ventures, one of the world’s leading venture funds with a portfolio including the likes of Dropbox, Skype, Figma, Bird, Slack and many more incredible companies. As for Sarah, at Index, she works with groundbreaking companies including Notion, Slack, Pitch, Quill and Instabase. Prior to Index Sarah spent time at CapitalG, Warburg Pincus and even worked in The White House as Policy Advisor for the National Economic Council.
Akshay Kothari is the COO @ Notion, the company that has taken the modern working world by storm as the all-in-one workspace to write, plan, collaborate and get organised. Just last week Notion raised a $50M round led by Index at a reported $2Bn valuation. Prior to Notion, Akshay spent 5 years at LinkedIn following his prior company, Pulse News, being acquired by LinkedIn in 2013.
In Today’s Episode You Will Learn:
1.) How did Sarah make her way into the world of venture from The White House and come to be a Partner @ Index today? How did Akshay parlay his angel investment into Notion into joining as COO the company 5 years later?
2.) With such a proliferation of collaboration tools today, how does Sarah see the remote work/collaboration tools landscape playing out? Are wein a phase of bundling or unbundling? Will we enter a phase of heavy consolidation? How does Notion think about the transition from an application to a platform? What are the challenges in doing so?
3.) What have been some of Akshay's core observations and learnings from watching the world move to remote work overnight? What behaviours will remain post COVID? What behaviours will not? What sectors will be forever changed due to the crisis? What opportunities does that bring about?
4.) Why did Notion decide to keep the team so small for so long? What are the advantages? How does Notion think about maintaining quality when hiring for scale now? What have been some of Akshay's biggest learnings in what it takes to attract A* talent to Notion?
5.) Why did Notion choose the route of profitability over the more conventional early path of the VC treadmill? How does one's mindset change when suddenly raising a large round of new financing? What becomes possible? What guard rails still need to be set?
Items Mentioned In Today’s Show:
Akshay’s Fave Book: Order without Design: How Markets Shape Cities
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.
David “DHH” Heinemeier Hansson (@dhh) is the creator of Ruby on Rails, founder and CTO at Basecamp (formerly 37Signals), and the best-selling co-author of Rework and Remote: Office Not Required. If that was not enough, fun fact, he went from not having a driver’s license at 25 to winning, at 34, the 24 Hours of Le Mans race, one of the most prestigious automobile races in the world. It is often called the “Grand Prix of endurance and efficiency.”
In Today’s Episode You Will Learn:
1.) How David made his way into the world of tech and startups from his childhood living in Copenhagen and how a cold email led to the founding of Basecamp with Jason Fried?
2.) What have been some of David’s core observations as people move to remote work over the last few weeks? What is the #1 mistake that 90% of teams make? How does David advise founders to approach loneliness and depression in their team? What strategies have Basecamp used to unite the team and inspire collaboration and teamwork?
3.) Why have David and Jason always tried to keep the Basecamp team as small as possible? Why does David believe one of the biggest problems is that execs have too much time? How does that manifest itself? What does David’s week look like? How does he approach meetings?
4.) Why does David hate the majority of “mission statements” today? What are the best composed of? What are the worst? What feelings does David believe your mission statement should inspire in the reader? What does David believe one needs to do to build a challenger brand today?
5.) Why has David and Basecamp always resisted the conventional path of raising VC funds? Why does David believe needs VC money is total BS? Why does David believe it is BS to chase being a unicorn? Why have founders got this so wrong today and what can they do to change?
6.) How would David describe his relationship to money? How has that relationship changed over time? What are the core challenges as one moves from a monetary to a deeper appreciation of what makes one happy? How did the transition occur for David? How does David advise others in terms of finding their moment for the transition?
Items Mentioned In Today’s Show:
David’s Fave Book: Erich Fromm: To Have Or To Be
As always you can follow Harry, The Twenty Minute VC and David and on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.
Blake Scholl is the Founder & CEO @ Boom Supersonic, the world's fastest commercial aeroplane, aspiring to bring back supersonic passenger flight at an affordable price. To date, Blake has raised over $166M in funding with Boom from the likes of Paul Graham, Sam Altman, Ray Tonsing @ Caffeinated Capital, Homebrew and 8VC to name a few who have featured on the show in the past. Prior to changing the world of commercial flight, Blake started his career with a 5-year stint at Amazon as a Manager of Social Networks and Automated Advertising. Blake then went on to found his own company, Kima Labs, acquired by Groupon in 2012 where he then spent 2 further years before founding Boom.
In Today’s Episode You Will Learn:
1.) How Blake made the move from Groupon to changing the way we think about commercial travel today with Boom Supersonic?
2.) How was the fundraising process for Blake given he was raising for supersonic jets? What is his most memorable fundraising moment? Where does Balek believe investors provide outsized value? Where could the investing class improve? How should the fund structures today change?
3.) What deliberate choices and decisions has Blake made to find and acquire the best talent? What is Blake's favourite interview question? What works? What does not work? What specific elements has Blake built into the culture at Boom to build operational excellence?
4.) How has Blake seen himself evolve and develop as a leader over the last few years? What have been the most challenging elements to develop and scale? How does Blake feel on whether founders should have experience on the industry they are entering or if there are benefits of not having so?
5.) What would Blake really like to change about the world of tech and Silicon Valley today? How does Blake feel about the current level of both innovation and founder ambitions? What can be further done to foster this in the coming years?
Items Mentioned In Today’s Show:
Blake’s Fave Book: Atlas Shrugged
As always you can follow Harry, The Twenty Minute VC and Blake and on Twitter here!
Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.
Fred Destin is a Founding Partner @ Stride.VC, one of Europe's newest and largest early-stage seed firms. Prior to co-founding Stride, Fred was a General Partner @ Accel where he was the lead investor and board member at Deliveroo, Pillpack (acq. AMZN for $1BN) and Carwow. Prior to Accel, he was a partner at Atlas Venture (now Accomplice) where he invested in and served on the board of Pillpack, Zoopla (IPO), Secret Escapes, Integral Ad Science (partial exit to Vista at $850M) and TheCurrencyCloud to name a few. Fun fact, his portfolio has a total enterprise value of more than $10BN and he generated in excess of $700M in exit value to investors.
In Today’s Episode You Will Learn:
1.) How did Fred make his way into the world of venture and come to co-found one of Europe's newest and largest seed funds in Stride.VC?
2.) If you look to Twitter, all VCs are "open for business", does Fred really believe the market is still open for business? How will deal volume be affected? How bad does Fred think this could get? How does this downturn compare to that of the dot-com and 2008?
3.) Why did Stride decide to take the decision to pause on investing at this moment in time? How does Fred respond to the suggestion of better pricing and less competition at this time? How does Fred believe venture investors view of risk evolves at this time? What is the first to change?
4.) With many new funds deploying their first fund in 18 months, does Fred think we will see a gravyard of new fund managers out of cash and with cash hungry portfolios? What advice does Fred give to newer managers of other elements they have to be minfdul/aware of?
5.) How does Fred think about the right way for managers to communicate with their LPs at this time? What has Stride done that has worked? Does Fred believe we will see many LPs defaulting on their initial commitments? How does Fred think emerging managers can navigate this?
Items Mentioned In Today’s Show:
Fred’s Fave Movie: Mulholland Drive
Fred’s Most Recent Investment: Collective Benefits
As always you can follow Harry, Fred and The Twenty Minute VC on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Ravi Viswanathan is the Founder and Managing Partner @ NewView Capital, launched in 2018 with their $1.35Bn Fund I, they have already set themselves as leaders in the world of growth funding with 3 massive exits in less than 2 years in the form of Plaid, sold to Visa for $5.3Bn, Acquia, sold to Vista Equity for $1Bn and then Scout, sold to WorkDay for $540M. Prior to founding NewView Ravis spent 14 years at one of the largest venture firms in the business, NEA where he co-led their venture growth equity practice and in 2016, became COO @ Nea. Before the world of venture, Ravi spent 4 years as a VP @ Goldman Sachs and before that was at McKinsey & Co.
In Today’s Episode You Will Learn:
1.) How Ravi made his way into the world of venture from investment banking and how that led to his founding the monster $1.35Bn Fund I for NewView Capital?
2.) Given the first fund being $1.35Bn, how did Ravi find the fundraising process for NewView? On reflection, what did he and the team do well that they would do again? What did they not do well that they would alter? What advice would Ravi give to first-time fund managers raising today?
3.) Would Ravi agree with Bill Gurley, "the biggest challenge today is the sheer quantum of capital flowing into the industry"? What does Ravi make of the rise of private equity (PE) houses entering the venture landscape? How does it change the exit landscape?
4.) How does Ravi think about the right way for funds to navigate and approach the secondary market? What advice would he give to emerging managers? How does Ravi feel about founder secondaries? What framework does he use to determine whether the amount is reasonable?
5.) How does Ravi think about what it take to truly win the best deals in competition today? If one does not have the budget of a16z, how does one build a venture platform? Where do the majority of investors make mistakes when it comes to VC value add?
Items Mentioned In Today’s Show:
Ravi's Fave Book: Shoe Dog: A Memoir by the Creator of NIKE, Born A Crime: Stories from a South African Childhood
Ravi’s Most Recent Investment: Plaid
As always you can follow Harry, Ravi 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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Jean-Charles Samulian is the Co-Founder & CEO @ Alan, the startup revolutionising health insurance with a service centred on people, simplicity and comfort. To date, Jean-Charles has raised over $85M in funding with Alan from some of the best in the business including Jan Hammer @ Index, Shakil Khan, Tom Stafford @ DST, Xavier Niel and Brent Hoberman to name a few. Prior to changing the healthcare insurance system, Jean-Charles founded Expliseat, revolutionising airline seating for economy class, now used by some of the world's leading airlines.
In Today’s Episode You Will Learn:
1.) How Jean-Charles made his way from re-inventing the airline seating industry to re-inventing the way consumers experience healthcare insurance? How did re-inventing the airline seat prepare and impact Jean-Charles' mindset going into the highly regulated healthcare market with Alan?
2.) How does JC structure his investor updates? What framework does JC believe these investor updates should take? Does he include thank you's at the end? Does he include requests for help? How does he involve the team in the writing of these updates? How does JC insert core strategic thinking into his updates? How much time does JC allocate to writing updates? How does JC think about transparency when coming investor updates?
3.) How has JC created a culture of distributed ownership combined with radical transparency? What are the key elements to achieve this? Where do so many go wrong with culture maintenance and creation? What have been the biggest challenges in scaling from 20 to 190 people in just 2 years? What has worked? What has not worked?
4.) How does JC structure the hiring process at Alan? Why does JC believe in the importance of "shadowing" for people to be excellent at hiring? How does JC define "excellence" in a potential candidate? What questions does JC most like to ask candidates? How does JC think about the right way to optimise new employee onboarding? Where do many go wrong with onboarding? What have been their core lessons at Alan as to what it takes to make it great?
5.) How does JC think about extreme self-organization today? How does JC structure his day and his time? How would JC summarise his relationship to his phone? What does he actively do to reduce his dependence on his phone? What has worked and what has not worked with regards to increasing productivity? How does JC advise others looking to make their first steps in increasing their productivity?
Items Mentioned In Today’s Show:
Jean-Charles’s Fave Book: The Everything Store: Jeff Bezos and the Age of Amazon
As always you can follow Harry, The Twenty Minute VC and Jean-Charles and on Twitter here!
Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.
Howard Marks is the Co-Founder and Co-Chairman of Oaktree Capital Management, a leading investment firm with more than $120 billion in assets. Prior to founding Oaktree, Howard spent 10 years at The TCW Group, where he was responsible for investments in distressed debt, high yield bonds, and convertible securities. Previously, Howard was with Citicorp for 16 years, where he served as Vice President and senior portfolio manager in charge of convertible and high yield securities. Howard has also written two books, most recently Mastering the Market Cycle: Getting the Odds on Your Side, and it was Warren Buffet who said, “When I see memos from Howard Marks in my mail, they’re the first thing I open and read. I always learn something.”
In Today’s Episode You Will Learn:
1.) How Howard first made his way into the world of finance over 50 years ago? How did not getting an investment banking job change the course of Howard’s life?
2.) What does Howard believe is the fundamental economic crisis occurring today? How does Howard expect liquidity availability to change over the next few years? What analogies of prior downturns and recessions can we look to learn from? How does this downturn differ and align to prior recessions and downturns? What policies would Howard like to see governments enact to prevent the worst-case scenario?
3.) In conditions of such uncertainty, how does Howard think about how to manage and move forward with such volatility? What are Howard's frameworks and mechanisms to analyse crises events like this? Taking the analysis one level further, how bad does Howard believe this could get? If short of The Great Depression, are there scenarios that could lead there? What are the leading signals?
4.) Being proactive, how does today's situation change the mentality and activity at Oaktree? Why does Howard not agree with the notion of "the falling knife"? How does Howard think about market bottoms? How does Howard determine the right insertion point? Why does Howard believe the best investors are unemotional? How can one manage the psychology of catching a falling knife that falls further?
5.) What advice would Howard give to the may millions of working professionals today that have never seen a recession in their professional career? What makes Howard the most nervous when he looks at and assess the landscape today? What does Howard believe is the biggest misconception people believe with regards to the current economic crisis?
Items Mentioned In Today’s Show:
Howard’s Fave Book: Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets
As always you can follow Harry, The Twenty Minute VC and Howard on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.