The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

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Alex Pall and Drew Taggart are the Founders of The Chainsmokers and Mantis. The Chainsmokers are one of the most sought after musical acts of our time. As for Mantis, just last week they announced their first $35M venture fund and have backing from Ron Conway, Mark Cuban and Keith Rabois. They have already invested in hotly contested rounds for Fiton and Loansnap. Drew and Alex also own a production studio, are stakeholders in the spirit brand JaJa Tequila and last year co-founded the anti-scalper ticketing platform Yellowheart. In Today’s Episode You Will Learn: 1.) How Drew and Alex made their way into the world of tech and startups and how they came to found a venture firm with Mantis? 2.) Why did Alex and Drew decide now was the right time for the fund? What did they look for in their LPs? How do they use their LPs to strategically help their companies? What is their preferred stage, sector? Do they have ownership requirements? 3.) Are Alex and Drew nervous about making the move into venture? If everyone has a chip on their shoulder, where does the chip on their shoulder come from? How do they think about their own vulnerabilities? How do they manage them? What works? What does not? 4.) What ways do Alex and Drew most like to work with their founders? Where do they provide outsized value? What are some examples of this? How do they think about working with VCs to get into the best rounds? How do they want to position Mantis in the ecosystem? 5.) With the tequila brand, the film production company and now the venture fund, how do they think about the expansion of "The Chainsmokers Empire"? What does this look like in 10 years? How would they like it to expand and grow? Items Mentioned In Todays Episode Drew's Favourite Book: The Unbearable Lightness of Being 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.
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! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    
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!
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! 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.
Matt Mochary coaches some of the world's leading venture capitalists and founders helping them to build the best organizations possible. On the VC side, Matt has worked with Peter Fenton @ Benchmark, several Sequoia Partners, Hemant @ GC and Mamoon @ Kleiner to name a few. As for founders, Matt has worked with the founders of Brex, Coinbase, Plaid, Reddit, Flexport and more. Prior to coaching, Matt began his business career as an investor with Spectrum Equity Investors.  He then co-founded Totality, eventually sold to MCI/Verizon.  In his own words, Matt went on to have fun (making the Academy Award short-listed documentary Favela Rising) and do good (starting the Mochary Foundation). In Today’s Episode You Will Learn: 1.) How Matt made his way from growth investor to immensely successful founder to now coaching the world's leading investors and founders? 2.) How does Matt advise founders to think about their relationship towards fear and anger? Why doe they generate bad quality of decision-making? What should be done when one recognises they are fearful or angry? Where do many founders and investors go wrong here? 3.) How does Matt advise founders who struggle with issues of self-doubt and imposter syndrome? What process should they go through to gain their confidence? What should they not do? How should they communicate their self-doubt to their team and the world? 4.) How does Matt advise founders in terms of the optimal communication strategy both with their team and their co-founders? Does radical transparency need to be instant or should it be timed correctly? What are the best conflict resolution strategies between founding teams? 5.) Why does Matt believe boards are the death of investors? Why are board members not optimally placed to advise their founders? What does Matt believe makes the best board members having worked with the likes of Peter Fenton? What does Matt advise new board members to be the best board member they can be? As always you can follow Harry, The Twenty Minute VC and Matt on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Ashton Kutcher is a Founder & General Partner @ Sound Ventures. Over the last 5 years, Ashton and his partner, Guy Oseary, have built Sound into one of the West Coast's leading new entrants with a portfolio including Lambda School, Calm, Gitlab, Affirm, Bird and many more incredible companies. As for Ashton, he started his investing career as an angel with early home runs including Spotify, Alibaba, Skype, Airbnb and Optimizely. Due to his immense success both in media and technology, Ashton has been named one of TIME magazine’s “100 Most Influential People in the World”. In Today’s Episode You Will Learn: 1.) How Ashton made his way into the world of startups with his foray into angel investing in Skype, Spotify etc? How did that lead to his founding Sound Ventures most recently? 2.) How does Ashton's background in the world of media impact Sound's investment strategy and the type of deals they get excited by? Question from Daniel Ek @ Spotify: How did your deal sourcing look lin the early days? How has that changed over time and with the institutionalisation of Sound? 3.) Why does Ashton believe people creating the future are perpetually young? What question does Ashton always like to ask founders? What does he look for in their answer? How does Ashton ensure founders feel comfortable with him? What does he do to allow them to open up? What is the hardest thing Ashton feels he has persevered through? 4.) How does Ashton build strong product intuition about products in areas he is not familiar with? In terms of great product, Ashton backed Spotify with Daniel Ek and Shak Khan, what did Ashton see in Spotify way back then? How did Shak and Daniel innovate on distribution and customer acquisition with him and Spotify? 5.) What have been Ashton's learnings in what it takes to truly win the best and most competitive deals? Before as an angel, Ashton's check size was friendly, now with Sound it is competitive with VCs, how does Ashton approach the element of now competing with many VCs he once co-operated with? What does Ashton make of the rise of many celebrity investors today? Items Mentioned In Today’s Show: Ashton’s Fave Book: The Undoing Project: A Friendship that Changed the World, Scale: The Universal Laws of Life and Death in Organisms, Cities and Companies Ashton’s Most Recent Investment: Community As always you can follow Harry, The Twenty Minute VC and Ashton on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  
Gabriel Weinberg is the Founder & CEO @ DuckDuckGo, the Internet privacy company that empowers you to seamlessly take control of your personal information online, without any tradeoffs. Over the last 12 years, Gabe has scaled DuckDuckGo to doing 1.6Bn private searches every month, a team of 83 full time fully remote employees, raising funding from some of the best in the business; USV and most importantly, being a profitable company. If that was not enough, Gabe has also written two phenomenal books, Traction and Super Thinking.  CLICK TO PLAY CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Gabriel made his way into the world of startups and came to found one of today's leading search engines and privacy companies in DuckDuckGo? 2.) Gabriel decided to raise $13M from USV 4 years into the life of DDG, why did he believe that was the right time? Why does Gabe believe that DDG never needed any primary capital? How does Gabe advise founders to think when it comes to chasing profitability early? How does Gabe view the relationship between growth and capital? Are they in conflict or aligned? What does Gabe make of the many $100M rounds getting done today? 3.) How does Gabe feel about the lack of free and open distribution today? How does Gabe strategise when it comes to channel diversification? What is the right level of marketing channel diversification to have? How do you know when to really double down on one that is working? How should founders be thinking about channel saturation rates? What have been Gabes biggest lessons on payback period over the last 12 years with DDG? 4.) How does Gabe feel about the digital advertising duopoly on the internet between Facebook and Google? Why does Gabe argue that this duo of incumbents are so much more powerful than any other prior generation of incumbents? How does Gabe think about strategies to reduce their data monopolies? 5.) DDG is 83 people and fully remote, what have been Gabe's biggest lessons on what it takes to run a fully-remote team from Day 1? What mistakes did they make? WHat would Gabe advise founders contemplating the fully remote strategy? Why does Gabe have nor formal hierarchy or org chart internally at DDG? Why is this so important for culture and employee morale? Items Mentioned In Today’s Show: Gabe’s Fave Book: The Advantage: Why Organizational Health Trumps Everything Else In Business As always you can follow Harry, The Twenty Minute VC and Gabe on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Steve Huffman is the Co-Founder & CEO @ Reddit, home to thousands of communities, endless conversation, and authentic human connection. To date, Reddit has raised over $550m in funding from some of the world's leading investors including Sequoia Capital, Marc Andreesen, Peter Thiel, Ron Conway, Sam Altman, Josh Kushner, Alfred Lin and Tencent, just to name a few. Steve started his career at Y Combinator as one of their first alumni back in 2005. At YC, Steve co-founded Reddit with Alexis Ohanian, which they sold in 2006 to Conde Naste Publications. In 2010, Steve co-founded Hipmunk, making business travel seamless and easy. Then in 2015, Steve re-joined Reddit as their CEO. In Today’s Episode You Will Learn: 1.) How Steve made his way into the world of startups and came to be one of the very first ever entrants in the now hailed Y Combinator? How did that lead to the founding of Reddit? Why did Steve return to Reddit, the company he founded, in 2015? 2.) What were Steve's biggest lessons from his journey with Hipmunk when it came to product feedback and iteration? How does Steve assess people's reliance on data today to drive product decisions? Why does he believe 3 criteria must be considered? What are the other two? What time did Steve see the confidence of his own intuition really increase? 3.) How does Steve think about stress management today? What was he like when he was younger in his relationship to stress? What did he actively do to change his relationship to stress? How has Steve seen himself change and develop as a CEO? What have been the inflection points? What has he struggled and also made mistakes in the journey? 4.) What have been Steve's biggest lessons when it comes to hiring truly A* talent at scale? What are the commonalities in the very best hires Steve has made? In the cases of it not working, what does Steve advise founders on the right way to let someone go? How does one do it with efficiency and compassion? 5.) Why does Steve believe that in dense cities, self-driving cars will not be that useful? How does Steve envisage the future of consumer transportation? What does he believe are the alternatives to self-driving cars? How does Steve see the future for the unbundling of social networks? Will they be unbundled into specific communities? How will this look? Items Mentioned In Today’s Show: Steve’s Fave Book: Shogun: The First Novel of the Asian saga: A Novel of Japan 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.
Howard Marks is co-chairman and co-founder 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.) Where does Howard think we are in the cycle today? What leads his thinking here? What is it crucial for all investors to remember at any point in the cycle? From a risk distribution and diversification perspective, does Howard believe now is a better or worse time to increase risk? 3.) Having worked through and been at the forefront of some of the most significant downturns of financial markets, what have been Howard's biggest learnings from seeing the booms and busts? How did it impact his investment mindset? At a point in 2008, Oaktree were deploying $600M per week for 15 weeks running, so how does Howard think about when is the right time to be aggressive vs when to pullback? 4.) How does Howard think about and assess his own price sensitivity? If there is one thing Howard wants to know to determine the right price, what is it? How does Howard believe we are seeing pro-risk mindsets alter investors attitude to price? How does Howard think about his right vs wrong and consensus vs non-consensus matrix? 5.) Howard and his Partner, Bruce have a very special relationship, what have they done to foster a relationship of radical intellectual honesty and that environment of safety? What are some things Howard will say to his team to encourage productive disagreement? What to Howard is the most important skill an investor can have is? 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.
Cyan Banister is one of the most successful and renowned early-stage investors of the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few. Today Cyan is a Partner @ Long Journey Ventures, joining the team there following a 4-year stint @ Founders Fund where she led deals in both Niantic and HQ Trivia. Prior to Founders Fund, Cyan was a super successful operator and angel, co-founding Zivity and before that being an early employee at Ironport, leading to their acquisition by Oracle. In Today’s Episode You Will Learn: 1.) How Cyan made her way into the world of startups? How SpaceX came to be her 1st angel investment? How that led to her joining the world of VC? 2.) How does Cyan think about and assess her relationship to money? Why does someone believe she had a fear or loathing of money? What made Cyan the capitalist she is today? How does Cyan analyse her relationship to risk? Has Cyan always trusted her own convictions? 3.) How does Cyan think about her own investment decision-making process? What were Cyan's biggest lessons from her experience with HQ Trivia? How did she change how she interacts with founders pre-investment? Why does Cyan never Google someone before meeting? 4.) How does Cyan think about price sensitivity today? Why does she believe there will be a reckoning? How will this shake out in terms of who succeeds and who fails? Why is Cyan in favour of party rounds? How does she think about VCs with sharp elbows? 5.) Why does Cyan believe SF is eating itself? What can be done to reinvigorate the city positively? What can be done to solve much of the homelessness problem? Why does Chesa Boudin never convict anyone? Why does Cyan believe her "BLM tweet is not spicy"? Why is Cyan fundamentally sad and worried for the current state of the world? Items Mentioned In Today’s Show: Cyan’s Fave Book: Snow Crash 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.    
Spike Lipkin is the Founder & CEO @ Newfront Insurance, the modern insurance brokerage empowering risk management experts with advanced technology to deliver innovative solutions to their clients'. To date, Spike has raised from some of the best in the business including Founders Fund, Meritech and 20VC Fund. Prior to founding Newfront, Spike was one of the first employees at Opendoor, where he helped grow the team from 5 people to an enterprise value of over $5Bn today. Prior to Opendoor, Spike was an investor at Blackstone, where he served on the startup team that built Invitation Homes into the largest owner of single-family real estate in the United States. In Today’s Episode You Will Learn: 1.) How Spike made his way from banking to be one of the first operators at Opendoor to founding the next generation of insurance with Newfront? 2.) What were some of the biggest takeaways for Spike from his time at Opendoor as employee #5? How does Spike approach prioritisation? How does he determine what to delegate vs what to control? 3.) How would Spike describe his own style of leadership? How has Spike needed to change his style with the business? What does Spike believe is his biggest weakness as a leader? What is he doing to confront it and grow as a leader? What is the most important thing a leader can do? 4.) How does Spike think about what it takes to acquire the very best talent? What does his framework for hiring look like? Why did Spike decide to hire a COO? Why was then the right time? How does Spike think about the balance between hiring external vs promoting internal? 5.) Why did Spike believe it was important not to announce any of his prior fundraises? How did Spike approach investor selection with Newfront? Does Spike believe founders should meet with VCs between fundraises? Which angel has done the most to move the needle for the company? How? Items Mentioned In Today’s Show: Spike’s Fave Book: Team of Rivals: The Political Genius of Abraham Lincoln 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.
George Zachary is a General Partner @ CRV, one of the nation's oldest and most successful early-stage venture capital firms with a portfolio including the likes of Airtable, DoorDash, Dropbox, Niantic and many more. As for George, today at the firm he focuses on advancing health through revolutionary computer science, centred around bio-engineering. During his incredible 16 year tenure at CRV, he has led deals in the likes of PillPack, Udacity, Scribd and HealthIQ. Before joining CRV, George was a General Partner @ Mohr Davidow Ventures for over 6 years. In Today’s Episode You Will Learn: 1.) How George made his way into the world of venture over 21 years ago and how he came to be a General Partner @ CRV 16 years ago? 2.) How did seeing the booms and busts of the dot com and 08 impacts George's investment mindset? What is the right way to voice concerns in an internal investment discussion? How does George now view capital intensity? How does it impact his conviction and check size? 3.) Why does George believe one should invest in founders who do not need their investors help? Why does George believe the best founders have experienced some form of parental instability? How does George detect the psychological need to win when he meets founders? What are the signs? 4.) How would George describe his own philosophy of board membership? How has it changed over time? What are the 2 control functions that a board member has? What advice does George give to new board members today? Where do many young board members make mistakes? 5.) How does George analyse his own personal relationship to money? How has it changed over the years? How did his relationship to money change his relationship with people? Was that challenging? How did he cope with it? How does he advise others who experience the same? Items Mentioned In Today’s Show: George's Favourite Book: Foundation Trilogy George’s Most Recent Investment: Glympse Bio 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.
David Lawee founded CapitalG, Alphabet’s independent growth fund, in 2013, drawing on his experience both at Google and as a serial entrepreneur. Since then, he has helped transform high-potential startups into some of the most highly valued businesses of our generation, including Airbnb, Lyft, Snap, Robinhood, Credit Karma, Oscar, Lending Club and Thumbtack. Prior to CapitalG, David played a pivotal role in Google’s growth story--first as Google’s Chief Marketing Officer and then as the instrumental VP of corporate development where his group spearheaded over 100 acquisitions for the company. CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How David made his way into the world of startups, came to be the first CMO @ Google and how that led to his founding CapitalG? 2.) Having operated and invested through both the dot com and 08', how has seeing the booms and busts impacted David's investing mindset? How does David think about temporal diversification today with CapitalG? Why does David believe diversification is largely overrated? 3.) How does David think about portfolio construction today, given CapitalG is a growth fund? How does David compare early-stage to growth today? How does David think about loss ratios at growth? How does David benchmark good vs great from a multiple perspective at growth? 4.) How does CapitalG approach investment decision making today? How does David avoid consensus thinking/following the crowd when it comes to deals? Why does David believe investment clubs operate much more successfully than partnerships? How does that change the structure for CapitalG? 5.) How has David seen himself evolve and develop as a board member of the years? What type of board member would David say he is today? How does that change with the founder? Who is the most memorable board member David has sat on a board with? Items Mentioned In Today’s Show: David’s Fave Book: Born A Crime: Stories from a South African Childhood  David’s Most Recent Investment: Albert 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.
Arlan Hamilton is the Founder and Managing Partner @ Backstage Capital, the seed fund that has paved the way investing exclusively in startups that are led by underrepresented founders. Backstage Capital also expanded their model and now have Backstage Accelerator working with companies across 4 cities. Last month, Mark Cuban gave Arlan $6M to invest in underestimated founders (ArlanWasHere Investments Fund I). Arlan is also an Author of "It's About Damn Time". If you would like to invest with Arlan, you can, check out BackstageCrowd.com with over 2,000 accredited and non-accredited investors, they just completed their 6th deal and $1m raised within 3 months of launch. In Today’s Episode You Will Learn: 1.) How Arlan made her way from the airport floor to founding her own venture firm, Backstage Capital and writing a book, "It's About Damn Time"? 2.) How does Arlan assess her own relationship to money and wealth? What is Arlan's thinking around her desire to give away 90% of her wealth? How does Arlan evaluate her own appetite for risk? How has that changed over time? 3.) From a strategic perspective, what are some core elements to Arlan's strategy that are not obvious? What are the main misconceptions that remain with regards to under-represented founders? What does Arlan believe are the leading indicators when assessing founders today? 4.) What does Arlan believe have been the biggest challenges in building the firm that is Backstage? What have been the core breaking points in the scaling of people and strategy? How does Arlan think about the relationship between brand vs reputation? What does Arlan believe are the main misconceptions people have about her? 5.) How would Arlan like to see the world of venture change over the next decade? What can LPs do to encourage more under-represented founders are backed? How can this be measured? Who should be held accountable? Items Mentioned In Today’s Show: Arlan’s Fave Book: What I Know For Sure by Oprah Winfrey 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.
Katherine Boyle is a Partner @ General Catalyst, one of the leading venture firms of the last decade with a portfolio including the likes of Stripe, Snapchat, Airbnb, Canva, Cazoo, the list goes on. As for Katherine, at GC she has led deals in game-changing companies such as Anduril, Nova Credit, Spring Discovery and Airmap to name a few. Prior to General Catalyst, Katherine entered the world of venture with Founders Fund and before that spent an incredible 4 years at The Washington Post where Katherine investigated entrepreneurship in many forms. In Today’s Episode You Will Learn: 1.) How Katherine made her way from investigating entrepreneurship at The Wall St Journal to being an intern at Founders Fund to today, being a Partner @ General Catalyst? 2.) Why does Katherine believe that journalism is like venture? Why does Katherine believe there are two different styles of venture? What were Katherine's biggest takeaways from her formative years in venture with Founders Fund? How did that impact her investing mindset? 3.) What does Katherine mean when she says she "invests solely on founder narrative fit"? Are there leading indicators of this fit? What advice did Katherine take from her conversation with Mike Moritz pre VC career? How does Katherine strategically avoid consensus thinking and decisions? 4.) How does Katherine approach market sizing? How does Katherine think about strategic insertion into niches that expand to much larger markets? How does Katherine assess market timing? How does Katherine determine the velocity of a market tailwind? What is an example of this? 5.) How does Katherine evaluate the rise of pre-empted rounds today? What advice does Katherine give to founders considering taking multi-stage money at seed? Why did it make sense for Anduril? How does Katherine gain the time of the founders when they are not raising? Items Mentioned In Today’s Show: Katherine’s Fave Book: The Decadent Society: How We Became the Victims of Our Own Success Katherine’s Most Recent Investment: Ophelia 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.
Palmer Luckey is the Founder @ Anduril Industries, founded on the premise of radically transforming the defence capabilities of the United States and its allies by fusing artificial intelligence with the latest hardware advancements. To date, Palmer has raised over $385M with Anduril from Founders Fund, a16z, Elad Gil, Spark Capital, Lux Capital, General Catalyst and 8VC to name a few. Prior to changing the world of defence, Palmer founded Oculus VR where he designed the Oculus Rift. Oculus VR was acquired by Facebook for $2.3Bn in 2014. In Today’s Episode You Will Learn: 1.) How Palmer made his way into the world of startups, made his way from trailer to selling Oculus for $2.3Bn to changing the defence industry with Anduril today? 2.) How does Palmer evaluate his own relationship to money? How has that changed since his $2.3Bn Oculus exit? How does Palmer assess his relationship to risk? How does Palmer approach the correlations between money, risk and happiness? 3.) What were some of Palmer's biggest takeaways from his time scaling Oculus? How have they informed his mindset with Anduril? What worked? What did not work? How has Palmer changed as a leader? How does Palmer approach personal development? How does he optimise for it? 4.) Palmer scaled Oculus to 1,400 people in 1 year, where do organisations break with scale? Why does Palmer believe, "you never want to play yourself"? Where does he feel his biggest weakness is as a scaling leader? How does Palmer approach hiring at scale yet maintaining culture? 5.) From a defence standpoint, why does Palmer feel the US needs to be more like the Chinese? Why is the DoD so poor at investing in innovation? What does it take to sell into the DoD really effectively? Why have the only 2 successful defence companies been founded by billionaires? Items Mentioned In Today’s Show: Palmer’s Fave Book: The Three-Body Problem 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.
Shishir Mehrotra is the Founder & CEO @ Coda, the startup that brings all of your words and data into a flexible all-in-one doc. To date, Shishir has raised over $140M from some great names including Greylock, Kleiner Perkins, General Catalyst, NEA and Homebrew to name a few. Prior to founding Coda, Shishir spent an incredible 6 years at Google in a couple of different roles; first as Director of Product for Youtube Monetisation and then moving to Youtube VP of Engineering, Product and UX. Before Google, Shishir was with Microsoft for 6 years as a Director of Program Management. Shishir also serves on the board of Spotify. In Today’s Episode You Will Learn: 1.) How Shishir made his way into the world of tech, came to be VP of Engineering, Product and UX @ Youtube and how it led to founding Coda? 2.) What is the No 1 quality of a good decision? How does Shishir think through reversible vs irreversible decisions? What are the 4 phases of decision-making? When should decisions be based on speed vs not? How can teams adjust questions to come to more productive outcomes? 3.) How does Shishir encourage debate and dissent within team discussions? How can leaders build deep trust with their teams? How can leaders create true democracy for idea sharing and meritocracy? Should ideas always be acted on immediately? What are the pros and cons? 4.) How does Shishir think about and evaluate his own operating cadence? How has this changed over time? How does Shishir approach time allocation? What have been his core learnings? How does Shishir divide his time between proactive and reactive tasks? 5.) How does Shishir approach OKR setting? What can leaders do to create aspirational and inspirational goals? How should goals be correctly communicated across orgs? How many OKRs should one team/person have? How should attribution across OKRs be given? Items Mentioned In Today’s Show: Shishir’s Fave Book: Switch: How to change things when change is hard  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.
Austen Allred is the Founder & CEO @ Lambda School, the startup that remotely trains people to become a web developer or data scientist and the students pay no tuition until they are hired. Just last month, Lambda's $74M Series C was announced led by Gigafund bringing their total funding to date to over $129M with prior investors including Stripe, Bedrock, GV, Gigafund and GGV to name a few. Prior to founding Lambda, Austen was Senior Manager for Growth @ LendUp and before that co-founded Grasswire. In Today’s Episode You Will Learn: 1.) How Austen made his way into startups having slept in a Honda Civic and how he went from homeless to rockstar founder @ Lambda? 2.) How does Austen evaluate his own attitude to risk? How does Austen think about downside protection today? How has this changed over time? How does Austen feel about founders taking secondaries? How does Austen think about his own relationship to money? 3.) Having raised his Series C last month, why did Austen choose the investors he did? How did the round progress? What made Gigafund different to alternate options? What makes the best board members in Austen's mind? What makes the worst? 4.) What have been the most challenging elements for Austen of scaling the team? How does complexity change with time in team scaling? Why did Austen bring in a COO? What did he look for in the role? How does Austen advise others on bringing in a COO? 5.) Why does Austen believe that post-COVID we will never go back to the valley as we knew it? Why does Austen believe the valley represents the biggest potential squandering of wealth in history? How does Austen evaluate the government intervention we have seen? 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.
Ravi Gupta is a Partner @ Sequoia Capital, one of the world's leading venture firms with a portfolio including the likes of Airbnb, Instacart, Stripe, UiPath, Zoom, the list goes on. As for Ravi, prior to Sequoia, he spent 4 years as COO & CFO @ Instacart playing an integral role in their hyper-growth journey. Before that Ravi spent 10 years as a Director @ KKR. In Today’s Episode You Will Learn: 1.) How Ravi made his way from KKR to being one of the key execs leading Instacart? How Instacart led to Ravi becoming a Partner @ Sequoia? 2.) When thinking about team, what does Ravi believe is the single most important question to ask? How does Ravi determine between good and great when assessing talent? What are the leading indicators? What have been Ravi's lessons on what it takes to acquire those great talents? 3.) How does Ravi think about and approach prioritisation today? How does Ravi analyse what to delegate vs what to control? Should you get good at your weaknesses and double down on strengths? How does Ravi think about vulnerability within leadership? How did he show that vulnerability as a leader at Instacart? 4.) In joining Sequoia, what has Ravi been most impressed with in regards to the team? What has he been most surprised by? Why is Ravi so bullish unanimous decision-making is right? How do founders determine which Sequoia Partner will be on their board? 5.) How does Ravi think about what it takes to be the very best board member? Who is the best board member Ravi has worked with? What made them so special? What advice does Ravi give to new board members adopting board seats for the first time? Items Mentioned In Today’s Show: Ravi’s Fave Book: Clay Christensen: How Will You Measure Your Life? 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.
Alex Tew is the Co-Founder and Co-CEO @ Calm, the #1 App for Meditation and Sleep allowing you to find your calm, sleep more, stress less and live better. To date, the company has raised over $143M in funding from some of the best including Lightspeed, Insight, TPG and then some very cool names such as Ashton Kutcher, Harry Styles, Brad Feld and Jason Calacanis. Prior to Calm Alex founded numerous other startups including PopJam, Pixelotto and most famously rose to internet fame with his founding of The Million Dollar Homepage. In Today’s Episode You Will Learn: 1.) How Alex went from playing Fifa with Michael Acton Smith in Berwick St, London to founding one of the hottest startups in the valley, Calm? 2.) What does Alex believe the very best brands do today? How do they message? How do they present? How do they divide opinion? How did Alex think about the early Calm brand? How has it changed? How does Alex advise others looking to build a company brand? 3.) Does Alex agree with Peter Fenton, "there is a lack of free and open distribution"? How does Alex analyse the economics for customer acquisition costs today? What is a good paid vs organic ratio? How do CACS change over time in Alex's experience? 4.) What have been Alex's biggest learnings on what it takes to build a viral product? Where do many people go wrong? Why does Alex believe pressure is the enemy of creativity? Does Alex believe people should create time for creative thought? What does Alex do to stimulate idea creation? 5.) How has Alex seen himself evolve and develop as a leader over the last 5 years? What have been the hardest elements to scale? How does Alex think about effective delegation? What have been Alex's biggest lessons on what it takes to hire A* people consistently? Items Mentioned In Today’s Show: Alex’s Fave Book: Godel, Escher, Bach: An Eternal Golden Braid 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.
Angela Strange is a general partner at Andreessen Horowitz, one of the leading venture firms of the last decade with a portfolio including the likes of Facebook, Github, Slack, Airbnb, Asana and more. As for Angela, she largely focuses on investments in financial services and is currently a board member of Addi, SynapseFi, and Tally. Prior to a16z, Angela was a product manager at Google where she launched and grew Chrome for Android and Chrome for iOS into two of Google's most successful mobile products. In Today’s Episode You Will Learn: 1.) How Angela made her way into the world of venture and came to be one of the leading fintech VCs with Andreesen Horowitz? 2.) Why does Angela believe that every company is going to be a fintech company? What is driving this shift? How does removing the barriers to entry for more products change both product quality and cost? How does Angela think about the role of regulation here? 3.) How does Angela think about what makes the best insertion points? How big does the initial wedge into the market have to be? When do you need to be able to prove you can transition from the insertion to the wider market? How does Angela fundamentally assess market size today? 4.) How does one transition to being the system of record? Do you have to be the system of record from day 1? Which examples are most striking for Angela on becoming a system of record? What are the biggest challenges in making this transition? Which metric tells you if you have become it? 5.) Does Angela think we are in a period of bundling or unbundling? What are the leading indicators of each? How does Angela assess the Fintech M&A market today? Will we continue to see large consolidatory moves in the form of Credit Karma, Plaid etc etc? Items Mentioned In Today’s Show: Angela’s Fave Book: Investing: The Last Liberal Art 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.
Alyson Friedensohn is the Founder & CEO @ Modern Health, a one-stop solution for employee mental well-being through evidence-based support and digital content. To date, Alyson has raised over $45M in funding from some of the best in the business including Kleiner Perkins, Founders Fund, John Doerr, 01 Advisors and Katrina Lake to name a few. Prior to founding Modern Health, Alyson was a Product Partner for Operations at Collective Health and before that was an operations manager @ Keas (acquired by Welltok). CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Alyson made her way into the world of startups and came to change how we think about mental health with Modern Health? 2.) How does Alyson think about and assess her own psychology? How does Alyson deal with crisis modes? What works? What does not? What is the driver for Alyson to get her through the very toughest of times? How does Alyson approach her own attitude to risk? 3.) What is Alyson's biggest pieces of advice for non-technical founders? What are the biggest challenges Alyson has had to overcome as a non-technical founder? How did she do it? How did Alyson strategically invest in the sales process? What worked? What did not? How does Alyson think about the balance of hitting sales quota and mental health? 4.) With some of the best VCs in the world, how did Alyson approach the process of investor selection? What can VCs do to build that relationship of trust with their founders? How does multi-stage VCs investing impact whether the founder remains in a "sales process" for the next round? How does Alyson temper the weight of John Doerr's words? 5.) What have been Alyson's biggest lessons in making it work marrying another founder? What works? What is challenging? How do they as a couple think about switching off? How does Alyson advise Harry on his own love life?! Items Mentioned In Today’s Show: Alyson’s Fave Book: How to Win Friends and Influence People 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.
Kevin Hartz is Co-Founder & Partner @ A*, a newly listed special acquisition company which raised $200M to acquire and take public a tech startup. Kevin is also the Co-Founder, former CEO, and Chairman Eventbrite (NYSE: EB). Before Eventbrite, Kevin was the Co-Founder & former CEO of online money transfer service, Xoom (acquired by PayPal for $1.1B). Kevin is also one of the most successful early-stage investors in the business with a portfolio including the likes of Airbnb (Seed, Series A), Uber (Series B), Pinterest (Seed, Series A), Trulia (first check) and PayPal (Seed). Troy Steckenrider is Kevin's co-founder and Partner @ A*. Prior to A*, Troy was COO @ ZeroDown changing the landscape for homeownership with $136M in funding. Before ZeroDown, Troy spent 5 years at Opendoor as Director of Capital Markets. Before that hyper-growth experience at Opendoor, Troy enjoyed roles at both Bain Private Equity and McKinsey. In Today’s Episode You Will Learn: 1.) How Troy and Kevin came together to co-found A*? What is a SPAC? What are Kevin and Troy looking to achieve with the SPAC? 2.) What does Kevin believe are the primary drivers for the rise in SPAC's over the last few years? How will they change the structure of both the VC and startup industry? How will the SPAC landscape evolve over the next few years? What is the biggest challenge they face? 3.) Why does Kevin believe that the fee structure for SPACs is egregious? How would they like to change the incentive structure? How does the timeline for a SPAC transaction compare to that of an IPO? How does the fee structure compare when comparing SPACs to banks in IPOs? 4.) Why did Kevin and Troy choose $200M for the right size for their first SPAC? How does the size of the SPAC determine the type of company the SPAC will merge with? What are Kevin and Troy looking for in their partner company? 5.) What does the fundraising process look like for a SPAC? How do SPAC sponsors deal with the challenge that LPs call pull out if they do not like the proposed partner deal? When evaluating SPACs, what do investors look to invest because of? What makes A* special? Items Mentioned In Today’s Show: Troy’s Fave Book: Churchill: Walking with Destiny 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.
Jennifer Tejada is the CEO @ PagerDuty, the company that provides a real-time operations platform ensuring less downtime for your digital services. Prior to their IPO in 2019 PagerDuty raised funding from some of the best in the business including Accel, a16z, Baseline, Bessemer and Harrison Metal to name a few. As for Jennifer, prior to PagerDuty, she was CEO of Keynote Systems leading to their acquisition by Dynatrace. Before Keynote, Jennifer was Executive Vice President and Chief Strategy Officer at Mincom, leading them to their acquisition by ABB. If that was not enough, Jennifer is also on the The Estée Lauder Companies Inc. (NYSE: EL). CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Jennifer made her way into the world of SaaS and came to be one of the leading enterprise CEOs today with PagerDuty? How does Jen advise graduates on joining a startup vs large incumbent? 2.) How does Jen analyse and evaluate her relationship to risk? What does Jen do to remove herself from her environment and make the clearest decisions? How has Jen's decision-making process changed? How does Jen encourage debate and free thought sharing internally? 3.) How does Jen think about the role of insecurity within leadership? What would Jen say are her biggest insecurities? How does Jen manage them and mitigate them today? What works? What does not? Why does Jen believe data is the key to overcoming insecurities? 4.) What have been Jen's biggest lessons on what successful board management looks like? What separates good vs great board members? How can CEO's structure their board in an optimal way? What do they need? What do they not need? How does scale change this? 5.) How does Jen think her style of leadership has changed over the years? What have been Jen's lessons on what it takes to both acquire and retain the very best execs? Where do many go wrong here? Items Mentioned In Today’s Show: Jennifer’s Fave Book: Tuesdays With Morrie: An old man, a young man, and life's greatest lesson 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.
Sahil Lavingia is the Founder and CEO @ Gumroad, the company that helps creators do more of what they love. With Gumroad, Sahil has raised funding from an all-star list of investors including Accel, Kleiner Perkins, First Round and then Max Levchin, Chris Sacca, Ron Conway and Naval Ravikant on the individual side. However, most recently Sahil has made waves launching one of the first rolling funds on AngelList with his being $6M per year. In the past, Sahil has backed the likes of Lambda School, Figma, HelloSign and Haus to name a few. In Today’s Episode You Will Learn: 1.) How did Sahil make his way into the world of startups and angel investing? What were his biggest takeaways from being employee #2 at Pinterest? How did that experience impact his mindset? 2.) Why did Sahil decide to make his new fund an AngelList rolling fund? How is it structured? Does Sahil think this will represent a seismic shift in early stage investing? Is this a game of the 1%? Why does Sahil think early-stage remains so undervalued? How will this impact Series A pricing? 3.) How does Sahil assess his own price sensitivity today? How does Sahil think about the right way to turn down a founder? Where do many go wrong? How does Sahil feel about the rise of pre-empted rounds? How does Sahil advise seed founders with offers from multi-stage firms? 4.) What does Sahil believe founders care most about today in their investors base? How does Sahil think about investor brand and distribution? How does Sahil analyse the pros and cons of party rounds? How does Sahil advise founders on constructing their early cap table? 5.) How does Sahil think about his relationship to risk and to money? How did Sahil deal with it when his investors wrote off his company? How did Sahil feel about the weight of expectation placed on his shoulders at such a young age? How did he deal with this? Items Mentioned In Today’s Show: Sahil’s Fave Book: How to Win Friends and Influence People 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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Podcast Details

Created by
The Twenty Minute VC
Podcast Status
Active
Started
Jan 13th, 2015
Latest Episode
Oct 19th, 2020
Release Period
2 per week
Episodes
714
Avg. Episode Length
30 minutes
Explicit
No
Order
Episodic

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