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

The Twenty Minute VC takes you inside the world of Venture Capital, Startup Funding and The Pitch. Join our host, Harry Stebbings and discover how you can attain funding for your business by listening to what the most prominent investors are directly looking for in startups, providing easily actionable tips and tricks that can be put in place to increase your chances of getting funded. Although, you may not want to raise funding for a startup. The Twenty Minute VC also provides an instructional guide as to what it takes to get employed in the Venture Capital industry, with VCs giving specific advice on how to get noticed from the crowd and increasing your chances of employment. If that wasn't enough our amazing Venture Capitalists also provide their analysis of the current technology market, providing advice and suggestions on the latest investing trends and predictions. Join us so you can see how you can get BIG, powerful improvements, fast. Would you like to see more of The Twenty Minute VC, head on over to www.thetwentyminutevc.com for more information on the podcast, show notes, resources and a more detailed analysis of the technology and Venture Capital industry.

20VC: Vinod Khosla on What Venture Assistance Really Means, Why Many VCs Are Not Qualified To Advise Founders & Why Startups Can Innovate So Much Faster Than Incumbents 02/24/2020

20VC: Vinod Khosla on What Venture Assistance Really Means, Why Many VCs Are Not Qualified To Advise Founders & Why Startups Can Innovate So Much Faster Than Incumbents is the Founder @ , one of the valley’s most renowned firms of the last decade with a portfolio including Square, Affirm, DoorDash, Impossible Foods and OpenDoor just to name a few. As for Vinod, he started his career as a Founder, founding Daisy Systems, a company that went on to IPO. Then in 1982, Vinod founded Sun Microsystems where he pioneered open systems and commercial RISC processors. In 1986, Vinod joined his longtime friend, John Doerr and became a General Partner @ KPCB where he helped incubate Juniper Networks and helped transform the telecommunications business with Cerent Corporation, which was acquired by Cisco Systems in 1999 for $7.2 billion. In Today’s Episode You Will Learn: 1.) How Vinod made his way into the world of startups with the founding of Daisy and Sun Microsystems and how that led to his entry into the world of venture with KPCB and ultimately founding Khosla Ventures? 2.) How does Vinod feel about the term "venture assistance" today? Where does Vinod believe VCs can really drive value? How does Vinod allocate his time to drive as much value for the portfolio as possible? How does Vinod get involved when it comes to talent acquisition for the portfolio? 3.) Why does Vinod believe that most board members are not qualified to advise entrepreneurs today? Why does Vinod believe that most value is driven outside of the board? What can founders to do make their boards as efficient as possible? How does Vinod advise founders to determine which advice to take vs which to disregard? 4.) How does Vinod assess his own approach and attitude to risk today? What does Vinod believe are acceptable vs unacceptable risks in startups? How does Vinod believe the very best founders think about risk management? Does Vinod agree time is the biggest killer of startups? Why does Vinod believe startups are so much quicker to innovate than incumbents? 5.) Why does Vinod believe that tolerance for failure has gone down in Silicon Valley? How does Vinod determine between the realism of when something is not work and to give up vs the visionary persistence to see a project through to the very end? What experience of his own have really led his thinking here? Items Mentioned In Today’s Show: Vinod’s Fave Book: , As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/13273832

20VC: Twitch Founder & CEO Emmett Shear on When To Persist vs When To Give Up For Entrepreneurs, The Fundamental Tension When Scaling Orgs and How To Optimise Them & How The Role of CEO Fundamentally Changes with Scale is the Co-Founder & CEO @ , the world's leading live streaming platform for gamers and the things we love. Prior to Twitch's exit to Amazon for a reported $970M, Emmett raised over $42M in funding from some of the best including Thrive Capital, Bessemer, Mike Maples, Aydin Senkut, Paul Graham and Y Combinator. Emmett is also a part-time Partner @ Y Combinator, advising YC companies on everything from fundraising strategy to product decisions to hiring and firing. Before Twitch, Emmett co-founded Kiko, a company he later sold on eBay for 6 figures. In Today’s Episode You Will Learn: 1.) How Emmett made his way into the world of startups with Kiko? How he ended up selling that for 6 figures on eBay? How that led to the creation of Justin.TV & Twitch? 2.) Why does Emmett believe starting a startup is like "deciding to take on the burden of Sisyphus?" At what point in the journey does is start to get easier? Does Emmett agree with many on the show who say, "it does not get easier, it just gets different"? How does one know when to give up vs when to persist and follow the vision? 3.) How does Emmett think about structuring an org at 1,500 people? Why does Emmett believe there is a fundamental tension when scaling teams between centralisation and decentralisation? How does one structure a reorg without causing instability? How does one communicate the reorg to the team? Where does Emmett see many go wrong here? 4.) Does Emmett agree the best CEOs are the best resource allocators? How does Emmett approach internal resource allocation today between both functions and projects? What does he find most challenging here? What does the decision-making process look like? What are his taekaways from Apple, Amazon and Microsoft in how they determine and process resource allocation internally? 5.) How does Emmett believe he has changed and evolved as a leader over the last 10 years with Twitch? What elements has he found the most challenging to master? What has he done to combat those weaknesses? Where has he always been naturally strong? What makes him so good at those particular functions? Items Mentioned In Today’s Show: Emmett’s Fave Book: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/13246121

20VC: Ashton Kutcher on Early Lessons From Investing in Airbnb and Spotify, Why VC Ownership Requirements Are Becoming More and More Egregious & What Being Good At Product Truly Means 02/17/2020

20VC: Ashton Kutcher on Early Lessons From Investing in Airbnb and Spotify, Why VC Ownership Requirements Are Becoming More and More Egregious & What Being Good At Product Truly Means is a Founder & General Partner @ . 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: , Ashton’s Most Recent Investment: As always you can follow , and Ashton on Twitter here! /episode/index/show/thetwentyminutevc/id/13180334

20VC: How Founders Should Think Through Distribution and Customer Acquisition Today, The Challenges of the Digital Advertising Duopoly Currently & How To Structure Company Post Mortems Effectively with Gabriel Weinberg, Founder & CEO @ DuckDuckGo is the Founder & CEO @ , 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, and 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: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/13151249

20VC: Lessons from 150 Angel Investments into the likes of Carta, Gusto, Airtable and Superhuman, Creating Algorithms and Models For Investing At Seed & Why Younger Investors Have An Advantage When It Comes To Finding Deals Early with Jude Gomila, Angel I is the Founder & CEO @ , creating the world's first self-constructing knowledge database built by artificial and human intelligence. To date, Jude has raised from some of the best in the business including Founders Fund, a16z, SV Angel and one of my dearest friends, Josh Buckley. Jude is also a prolific angel having invested in over 150 companies including Carta, Airtable, Superhuman, Gusto, Linear and many more incredible companies. Prior to Golden, Jude started Heyzap (now used by 100,000 mobile apps) alongside former guest Immad, now Founder of Mercury. In Today’s Episode You Will Learn: 1.) How Jude made his way into the world of tech and Silicon Valley having been born and raised in Harrow, London? How did he then make his way into the world of investing? 2.) What models should investors and founders have common ground on? Where are founders and investors often misaligned? What does Jude mean when he says he uses "algorithms for investing"? How are these algorithms structured? What is within them? How can/should people build their own? 3.) Why does Jude very much disagree with spray and pray to be the dominant model to make money at seed? How does Jude think about portfolio construction having now made 180 investments? How has Jude's approach and attitude to ownership changed over time? 4.) Does Jude agree with Semil Shah that founders are voting with their feet and taking multi-stage money at seed today? How does Jude evaluate the approach of multi-stage funds back into seed? How does Jude think about VC value add? Where does he believe they really can add value? Where do people think they do but they actually do not? 5.) How does Jude foresee the future of the early-stage market? Will we see a generation of old school venture firms die out? Why does Jude believe younger investors have a higher chance of finding and winning the next best deal? How does Jude believe the angel ecosystem will shake out? Will we fundamentally see the unbundling of capital? Items Mentioned In Today’s Show: Jude’s Fave Book: Jude's Most Recent Investment: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/13105187

20VC: Why You Never Want To Fight A Fair Fit For Distribution, Why No Great Company Is Built with 1 Product and When To Release Your Second & What Founders Can Do To Extract The Most From Their Cap Table with Shoaib Makani, Founder & CEO @ KeepTruckin is the Co-Founder & CEO @ , the modern fleet management platform building solutions that make drivers and fleets safer, smarter, and more efficient. To date, Shoaib has raised over $229M from some of the world's leading investors including Index, GV, Greenoaks, IVP & Scale Venture Partners. Pre-founding KeepTruckin, Shoaib was an investor @ Khosla Ventures where he led investments in Instacart, Everlane and Indiegogo to name a few. Before venture with Khosla, Shoaib was on the operations side enjoying roles at both Google and Admob. In Today’s Episode You Will Learn: 1.) How Shoaib made his way from the very comfortable world of venture to changing the way trucking fleets are managed today with KeepTruckin? How does Shoaib analyse and assess his own attitude to risk today? 2.) How has Shoaib seen himself change and evolve as a leader over the last few years? How did his time investing impact how he approaches the role of CEO? How does Shoaib think about appropriate market sizing today? What advice does he give to founders on this? What is a reasonable market penetration to assume if successful? 3.) What advice would Shoaib give founders when it comes to successful board management? How does Shoaib ensure investors have the right context at the right time to provide advice? What does that information flow to investors look like? How does Shoaib determine between the advice to accept vs what to reject? 4.) Shoaib thought about distribution and customer acquisition long before he launched the product, why? What did this thought process conclude with? Does Shoaib believe you have to own your own lines of distribution to succeed? How does Shoaib feel when it comes to current CAC's on incumbent platforms? 4.) As a founder, what does Shoaib say is his biggest mistake made in the KeepTrickin journey? How does Shoaib think about what it takes to acquire the very best talent? How does Shoaib advise founders work with recruiters? What can they do to really get the most out of them? When can this function be brought in house? Items Mentioned In Today’s Show: Shoaib’s Fave Book: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/13055939

Breaking News: Meet First Round Capital's Newest Partner, How To Approach Generational Transition as a Venture Firm & The Dangers of Attribution In Venture 02/04/2020

Breaking News: Meet First Round Capital's Newest Partner, How To Approach Generational Transition as a Venture Firm & The Dangers of Attribution In Venture is 's newest Partner (announced today) having spent the last 2 years as a Founder-in-Residence working with the FRC portfolio. Prior to his time in venture, Todd spent close to 3 years at Dropbox as VP Product & Design. Before that he was with Twitter as Director of Product Management, following his startup, Cover, being acquired by Twitter in 2014. Before founding Cover, Todd was a Product Manager @ Facebook where he helped lead major redesign of Newsfeed. Finally, Todd started his career at Google as a Product Lead taking Gmail from 0 to 200m users in 4 years. Todd is joined today by his Partner @ First Round, . Phin also writes the most fantastic blog, , that really is a must-read. In Today’s Episode You Will Learn: 1.) Phin, what is the exclusive news you would like to break on the show today? Todd, taking one step back, how did you make your way to this stage, what was your entry into technology and how did you come to be a Partner @ First Round Capital today? What were Todd's biggest takeaways from working on some of the most transformative social products in Gmail, Twitter, Newsfeed @ Facebook and Dropbox? 2.) What advice does Phin have for Todd when it comes to entering a venture partnership? Where do many people go wrong in their first year in venture? What should Todd be optimising for in the partnership? In terms of measurement, how does one measure success of the first year of work as a Partner? 3.) Todd, making the move from angel to institutional VC is a mindset shift, how does Todd think his investment mentality will be impacted by the shift from angel to institutional VC? Having raised funding as a founder, what type of founder experience and investor does Todd want to be and bring? 4.) Phin, it has been a long time since FRC added a Partner, walk me through the recent changes at the top of FRC? What are the most important qualities for First Round when adding a Partner? What are the biggest tips to doing generational transition well? Where do many firms go wrong in generational transition? Items Mentioned In Today’s Show: Todd’s Fave Book: , Todd’s Most Recent Investment: , As always you can follow , and on Twitter here! Businesses are always looking for ways to shorten their sales cycles. provides secure, effortless eSignatures proven to speed up contract signing by 80%. Most clients go from a multi-week turnaround to a multi-hour one. They’re an industry leader and have been voted #1 for Ease of Use two years in a row on G2 Crowd. Don’t let pen and paper processes slow you down. to join the millions of users already using HelloSign to close more deals faster! /episode/index/show/thetwentyminutevc/id/13012022

20VC: Alexa Von Tobel on Raising NYC's Largest Ever Female Led Fund , Portfolio Construction, Compression of Fundraising Timelines, Reserves Management & Personal Branding in Venture 01/31/2020

20VC: Alexa Von Tobel on Raising NYC's Largest Ever Female Led Fund , Portfolio Construction, Compression of Fundraising Timelines, Reserves Management & Personal Branding in Venture is the Founder & Managing Partner @ , announced in 2019 as the largest ever female-led VC fund based in NYC. Prior to co-founding Inspired, Alexa founded LearnVest where she enjoyed an incredible 11-year journey culminating in their $250M exit to Northwestern Mutual in 2015. Alexa is also the author of New York Times Bestseller "Financially Fearless" and is an inaugural member of the Presidential Ambassadors for Global Entrepreneurship for the White House. In Today’s Episode You Will Learn: 1.) How Alexa made her way into the world of startups with the founding of LearnVest? How did that experience running LearnVest lead to her founding NYC's largest-ever female-led VC fund in the form of Inspired? 2.) How does Alexa think about portfolio construction with the new $200M fund? What does she mean when she says they have segmented it into 3 distinct and separate buckets? How much is in each bucket? How does Alexa think about reserves and re-investment decision making? What is the process here? 3.) As a former entrepreneur, how does Alexa think about those moments when the VC and the Founder are no longer aligned? What are those moments? How does Alexa approach the aspect of saying no to founders? What is the right way? How does Alexa feel about the compression in fundraising timelines? How does Alexa meet founders before they raise their round? 4.) Why does Alexa believe that capital is no longer the differentiator? How does Alexa think about personal brand in venture today? Where does Alexa believe are the most crucial times for reputation building? How does Alexa approach time allocation across the portfolio? What is the correlation between decision-making and reputation? Items Mentioned In Today’s Show: Alexa’s Fave Book: Alexa’s Most Recent Investment: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12961814

20VC: Moxxie Ventures' Katie Stanton on What It Takes To Raise A First Time Fund As A Solo GP, The Entrance of Multi-Stage Funds Into Seed Rounds and The Inverse Relationship of Those That Fund Diverse Managers and Those That Say They Do is the Founder and General Partner of , investing in founders who make life and work better. Prior to Moxxie, Katie was a Founding Partner of #angels and has the most incredible angel portfolio including Airtable, Carta, Cameo, Coinbase and Modern Fertility to name a few. Katie also served in numerous executive operating roles at, , , and and also served in the (Obama) White House and State Department. If that was not enough, Katie is also on the board of Vivendi and previously sat on the board of Time Inc. In Today’s Episode You Will Learn: 1.) How Katie made her way into the world of tech with Yahoo? How did that translate into her investing in Lowercase Fund I? How did the angel investing lead to founding Moxxie? How has Katie found her investment mindset has changed moving from angel to VC? 2.) How did Katie find the fundraise for Moxxie? How many LPs did Katie meet and how did she structure the process? What does Katie think she did well in the fundraise? What would she look to improve or change when raising for Fund II? What advice was Katie given in the process by Semil Shah which really changed her thinking? What advice would Katie give to other emerging managers raising today? 3.) Does Katie agree with Semil Shah that "founders are voting with their feet in taking multi-stage money at seed"? What advice does Katie give to founders who do have these offers from multi-stage funds at seed? How does Katie assess these later stage funds moving earlier? How should smaller micro-managers respond to this? 4.) How does Katie think about portfolio construction today with Moxxie? What are the hard rules that mean Katie is willing to walk away from a deal? How does Katie think about and assess her own price sensitivity? In terms of decision-making, what support system has Katie built around herself to enhance her decision-making process? 5.) How does Katie advice founders when it comes to selecting their VC? What are the most common ways founders look for and need to help with? How does Katie think about party rounds? When are they good? When are they not? Why does Katie believe so much of the power has shifted to the hands of the founders? Items Mentioned In Today’s Show: Katie’s Fave Book: , Katie’s Most Recent Investment: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12898490

20VC: The Most Successful Companies Are Not Where Employees Work The Most, How To Know When To Promote From Below Or Bring in External Candidates & Why It Is A Unique Advantage To Be Building A Company Outside A Tech Hub with Rick Nucci, Founder & CEO @ G is the Co-Founder & CEO @ , the knowledge management platform that delivers everything you need so you can spend less time searching and more time doing. To date, Rick has raised over $38m with Guru from some of the best in the business including Thrive, Emergence Capital, Firstmark, Slack and Salesforce. Prior to Guru, Rick was the Founder of Boomi, which defined and led a new segment as the first-ever cloud integration platform-as-a-service. Boomi was ultimately acquired by Dell where Rick went on to grow the organisation into the industry leader it is today. In Today’s Episode You Will Learn: 1.) How Rick made his way into the world of startups originally and how he came to change the way we think about knowledge management with his founding of Guru? 2.) How would Rick describe his leadership style today? How has he seen his style change over the years? What have been those learnings and the inflexion points causing them? Does Rick believe can be learned as a leader? What does he recommend to founders wanting to become more empathetic? 3.) Culture is a fluffy and overused term, what does it mean to Rick? What has Rick done to purposefully build a very specific culture that he wanted to create? What specific initiatives have worked well? What have not worked so well? How does Rick think about culture maintenance with scale? What are the challenges with scaling culture? 4.) How does Rick think about the interview process when adding to the team at Guru? How do they literally structure it? What does their culture interview encompass? How heavily is it weighted? What specific questions do they ask and responses they look for? If it does not work out, what have been Rick's biggest lessons on letting people go? 5.) Rick is based in Philadelphia, often people say if you are not in a tech hub it is not possible to get the best talent, does Rick agree with this? In what roles does it make sense to hire from a tech hub for? What are the advantages of hiring outside of a hub? Fundraising wise, does Rick believe you have to have a presence in a core hub to raise from Tier 1 VCs? Items Mentioned In Today’s Show: Rick’s Fave Book: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12871607

20VC: Oaktree Capital’s Howard Marks on The Most Important Skill An Investor Can Have, The Right Way To Think About Price Sensitivity & Where Are We At Today; Take More Risk or Less? 01/20/2020

20VC: Oaktree Capital’s Howard Marks on The Most Important Skill An Investor Can Have, The Right Way To Think About Price Sensitivity & Where Are We At Today; Take More Risk or Less? is co-chairman and co-founder of , 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 , 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: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12806618

20VC: Portfolio Construction, Optimising SPVs, Opportunity Investing "Between Rounds", Being Distribution-Centric Over Product-Centric and Capital Concentration Within Funds With Sumeet Gajri, Chief Strategy Officer @ Carta is the Chief Strategy Officer @ , the startup that helps companies and investors manage their cap tables, valuations, investments, and equity plans. Sumeet is largely responsible for all things fundraising and M&A and Carta have raised over $485m from a16z, USV, Thrive, Spark, K9, Lightspeed and Meritech to name a few. Sumeet is also Managing Partner @ Original Capital, where he has partnered with companies including Front, Tonal, Instabase, Everlywell and Cockroach Labs to name a few. Finally, Sumeet is also an LP in world-leading firms such as USV and Valar Ventures. In Today’s Episode You Will Learn: 1.) How Sumeet made his first foray into the world of venture in NYC having grown up in Scotland? How that led to his move to operations with Carta? How his learnings from Carta led to his establishing Original Capital? 2.) How is Original Capital different from every other micro-fund? How does Sumeet approach portfolio construction with the fund? What is the optimal number in a portfolio? How does Sumeet think about loss ratio? What 3 criteria dos every new investment have to pass to make it into the portfolio? How does check size vary by deal? 3.) How does Sumeet invest in some of the best companies in between "official rounds"? What does this conversation look like with the founders? How does Sumeet analyse reserve allocations? What makes the right strategy? What are his capital concentration limits per company? How does Sumeet think about using SPVs effectively? 4.) Sumeet helps his companies fundraise a lot, what does the first step look like? How does he advise on investor selection? How does he advise on pipeline management? Should founders speak to investors when they are not raising? How open should they be in these meetings? What can founders do to catalyse the process? Where does Sumeet see many founders make mistakes? 5.) How does Sumeet think about distribution vs product? What can founders do to adopt a more distribution first mindset? What have been some of Sumeet's biggest lessons in turning Carta from a single product company to a multi-product company? Do companies have to own their own lines of distribution today? Items Mentioned In Today’s Show: Sumeet’s Fave Book: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12777887

20VC: Khosla Ventures Founding Partner, Samir Kaul on Why Pro Rata Is A Cop Out, Why He Likes Technical Risk and Does Not Take Market Risk & How To Approach Time Allocation Across The Portfolio In Venture is a Founding Partner and Managing Director at , one of the valley's most renowned firms of the last decade with a portfolio including Square, Affirm, DoorDash, Impossible Foods and OpenDoor just to name a few. As for Samir, he led the firm's investment in Guardant Health, , [NASDAQ: NTNX], , among others. Prior to Khosla, Samir spent five years at Flagship Ventures where he started and invested in early-stage biotechnology companies, including Helicos Biosciences which went on to IPO. Samir was also founding CEO of Codon Devices and led the Arabidopsis Genome Initiative at Craig Venter’s Institute for Genomic Research. In Today’s Episode You Will Learn: 1.) How Samir made his way into the world of venture from the world of biotech and came to found one of the leading firms of the last decade? 2.) How did seeing the booms and busts of the last 2 decades impact Samir's investing mindset? Why does Samir think it is dangerous for a VC to have a "conservative mindset"? How does Samir analyse and think about upside maximisation when investing today? How does Samir think about when to sell your position and how to determine the right time? 3.) What does investment decision-making look like at Khosla? What are the criteria that re-investments are made upon? Why does Samir believe that pro-rata is a kop out? Which should be the core questions that determine whether to double down or not? How does Samir and the partnership think about time allocation across the portfolio? 4.) How does Samir approach the exercise of market sizing? Why does Samir never want to take a risk when it comes to market? Why does Samir want to maximise his risk when it comes to technological risk? How does Samir think through having to carry these deep tech companies for longer? What were his learnings from the clean tech days on this? 5.) How would Samir analyse his own price sensitivity today? What was his most formative inflexion moment as an investor? What did he learn from it? From a people side, who had the biggest impact on Samir as an investor? What were the core elements he learned from them? How does Samir deal with the element of self-doubt? How does he get through those moments? Items Mentioned In Today’s Show: Samir’s Fave Book: Samir’s Most Recent Investment: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12714443

20VC: Raising $105m in Just 13 Months Over 3 Separate Rounds, The 5 Core Ways VCs Can Add Value & How Founders Can and Should Fully Leverage Their Cap Table with Kurt Rathmann, Founder & CEO @ ScaleFactor is the Founder & CEO @ , the startup providing an automated bookkeeping solution at its core, bringing all of your company’s important financial information into one place. To date, Kurt has raised over $105m with ScaleFactor from the likes of Byron Deeter @ Bessemer, Coatue, Canaan Partners, Stripes Group and Firebrand to name a few. As Michael @ Coatue told me before the show, there is no way Kurt was not going to be the founder of a bookkeeping company given his background. Prior to ScaleFacotr, Kurt was the CFO of KNS Communications and a Senior Audit Professional @ KPMG. In Today’s Episode You Will Learn: 1.) How did Kurt make his way into the world of startups and come to found the gamechanger for bookkeeping in the form of ScaleFactor? Does Kurt believe that Founders do need to be mission-driven or can founding a company be a more analytical exercise? 2.) How did it come to be that Kurt raised 3 separate funding rounds and over $105m in just 13 months? How does Kurt feel about the saying, "when there is money on the table, take it"? Having had his B and C pre-empted, how does Kurt feel about the rise of pre-emptive rounds today? How did Kurt approach the mental challenge of transitioning from resource-starved to relative resource abundance? Was that tough to do? 3.) What is Kurt's biggest advice to founders when it comes to investor selection? What does Kurt believe are the 5 things that VCs can do to add value? Why does Kurt believe it is the responsibility of the founder to extract that value from the VC? What can founders do to really get the most out of their investors? What has Kurt found to be the biggest value from his cap table? Where do founders think VCs add value but they do not? 4.) What are some very unique and deliberate things that Kurt does to create an amazing culture at ScaleFactor? How does he advise on creating great energy in the office itself? How does Kurt think about retaining that core ethos with the expansion to multiple offices? What have been some of the biggest challenges in scaling communications internally? 5.) Does Kurt believe that being outside of a core tech hub severely limits his ability to hire the best talent? What do founders outside of these hubs need to very strategically do? How does being outside of a core hub also impact how Kurt thinks founders need to approach fundraising? What specifically can they do to increase their odds? Items Mentioned In Today’s Show: Kurt’s Fave Book: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12687908

20VC: Why Now Is The Hardest Time To Raise an Institutional Pre-Seed in the Last Decade, What To Do When The Founder and VC Interests Do Not Align & The Rise of Pre-Emptive Rounds with Gaurav Jain, Founder & Managing Partner @ Afore Capital is Co-Founder & Managing Partner @ , one of the west coast's leading pre-seed funds with a $124M fund focused purely on pre-seed. To date, they have backed the likes of Petal, BetterUp, BenchSci and Modern Health to name a few. Prior to co-founding Afore, Gaurav was a Principal @ Founder Collective where he was directly involved with some incredible companies including Cruise (Acq. by General Motors for $1B+), Periscope (acq. by Twitter), Airtable and Dia & Co. Before venture, Gaurav spent time in operations both at Google as one of the first engineers for Android and then also founding his own company, Polar, a leading mobile solutions provider with $10m in funding. In Today’s Episode You Will Learn: 1.) How Gaurav made his way into the world of venture with Founder Collective and how that led to the realisation that Afore needed to exist in the funding landscape? What were the 3 biggest takeaways for Gaurav from his time at Founder Collective? 2.) Why does Gaurav believe now is the hardest time in the last decade to raise your first institutional round of funding? What is driving these capital reductions at pre-seed? How does Gaurav assess the rise of operator funds and super angels we have seen in the last 5 years? How does Gaurav advise founders on investor selection at pre-seed? 3.) What does Gaurav make of large multi-stage funds entering into pre-seed? Why does Gaurav strongly believe that you cannot apply the same financing product to a different market? Does this mean the multi-stage funds will revert back to later stages? 4.) How is Gaurav seeing Series A funds behaving? Why are they more aggressive now than ever before? What does Gaurav make of the rise of pre-emptive rounds? How does he advise founders on pre-emptive rounds? 5.) How does Gaurav think about portfolio construction today with Afore? What is the right level of diversification across the portfolio to be sufficiently diversified at pre-seed? How does Gaurav think about reserve allocation today? How does the decision-making process compare when comparing initial to re-investment decision? Items Mentioned In Today’s Show: Gaurav’s Fave Book: Gaurav’s Most Recent Investment: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12629993

20VC: Rahul Vohra @ Superhuman, The Most Downloaded Founder Episode of 2019 01/03/2020

20VC: Rahul Vohra @ Superhuman, The Most Downloaded Founder Episode of 2019 is the Founder and CEO @ , the fastest email experience in the world. Fun fact, users get through their inbox twice as fast — and many see Inbox Zero for the first time in years! To date, they have raised funds from our friends at Boldstart, First Round, John Collison, Sam Altman, Wayne Chang, Mike Ghaffery and Yes VC just to name a few. Previously, Rahul founded Rapportive, the first Gmail plugin to scale to millions of users. Rapportive was ultimately acquired by LinkedIn. In Today’s Episode You Will Learn: 1.) How did Rahul make his way into the world of startups with the founding of Rapportive and how did that transition to changing the world of email with Superhuman? 2.) What does Rahul mean when he says, “you can reverse engineer a process to get to product-market fit”? What does Rahul believe is the defining metric which determines your “product-market fit score”? What is Julie Supan’s framework? How did Dropbox and Airbnb use it to increase their product-market fit? How can founders implement it into their process? 3.) What can founders do to expand the customer base to include users that currently are “somewhat disappointed”? What are the right questions to ask? What do we do with this feedback? How do we further segment the user base? Why should we “disregard the users whereby the primary benefit of the product does not resonate”? 4.) How does Rahul approach product roadmap and prioritisation? How can founders ensure that continuous tracking and user feedback is engrained within the organisation? What tools does Rahul do to monitor and capture this? What are some of Rahul’s biggest lessons from going through this painstaking process stage by stage? 5.) Finally on fundraising, what does Rahul mean when he says, “always be raising but never be actively raising”? What are the benefits of this? How can founders transition catch up coffee into fundraising subtly? How does Rahul feel about party rounds? What are the pros? What are the downsides? How does Rahul advise founders here? Items Mentioned In Today’s Show: Rahul’s Fave Book: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12604910

20VC: Inside The Acquisition Decision-Making Process at Cisco, How To Measure True Success in M&A Evaluation & Why By Not Speaking To Corp Dev Teams You Are Closing The Door On The Biggest Potential Accelerator To Your Business with Rob Salvagno, VP of Co is VP of Corporate Development and at Cisco, where he is responsible for leading all M&A efforts as well as managing Cisco’s strategic venture capital which invests hundreds of millions of dollars annually. At Cisco, Rob led the $1.2 billion acquisition of Meraki, one of the most successful platform acquisitions in Cisco’s history, and the $3.7 billion acquisition of AppDynamics, cementing Cisco’s place in the business intelligence, analytics and IT operations market. Most recently, Rob engineered the $2.3 billion acquisition of Duo, the leading provider of unified access security and multi-factor authentication delivered through the cloud. Prior to the world of M&A, Rob was a technology investment banker at Donaldson, Lufkin & Jenrette. In Today’s Episode You Will Learn: 1.) How Rob made his way from investment banking to leading the M&A and venture activity for one of the world's largest tech players of the last decade? 2.) How do M&A teams like to get to know startups that they could invest in or acquire? How does Rob like to work with the venture ecosystem? How does Rob think on Paul Graham's comment of "do not talk to corp dev"? What are the nuances here? How does it differ for consumer vs enterprise? 3.) How does Rob define true success when it comes to M&A evaluation? Should corp dev be strategy first or transaction first? What have been Rob's biggest lessons on successful integration? Where do so many go wrong with integration post M&A? What questions can be asked ahead of time to know if integration and culture will be a fit? 4.) How does Rob reflect on his own price sensitivity today? How does Rob feel about the multiples enterprise companies are currently trading at? What have Rob's most successful acquisitions taught him about price and price sensitivity? How does Rob deal with the inherent conflict of investing and also acquiring companies? How does he communicate that to the companies he invests in? 5.) What does the acquisition-decision making process look like at Cisco? How does it differ on a deal by deal basis? What do Cisco do to allow them to move so much faster than any other M&A teams? What have been Rob's lessons on the importance of speed in winning the best transactions? Items Mentioned In Today’s Show: Rob’s Fave Book: Rob’s Most Recent Acquisitions: , As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12561470

20VC: Most Downloaded Episode of 2019 with Bill Gurley, General Partner @ Benchmark Capital 12/23/2019

20VC: Most Downloaded Episode of 2019 with Bill Gurley, General Partner @ Benchmark Capital is a General Partner @ , one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston where his research coverage included such companies as Dell, Compaq, and Microsoft, and he was the lead analyst on the Amazon IPO. In Today’s Episode You Will Learn: 1.) How did Bill make his way into the world of VC from Credit Suisse and come to be GP at one of the world’s leading funds in the form of Benchmark? What were Bill’s biggest takeaways from seeing the boom and bust of the dot com? How did that impact Bill’s investment mentality today? 2.) Why does Bill believe that one of the biggest challenges today is the abundance of capital? Subsequently, does Bill agree with Peter Fenton statement, “never turn down a deal based on the valuation it is a mental trap”? How does Bill assess his own price sensitivity? What was his learning here in meeting Larry and Serge early on with Google? 3.) How does Bill think about and approach market sizing today? How important is it to him when analysing an investment? Where does Bill believe a lot of managers make mistakes when assessing market sizing today? What was his big lesson here with Uber? How does Bill think about and evaluate market creation and market expansion plays? 4.) Bill has spent over 3,000 hours on some of the most famed boards of the last decade, how has Bill seen his style of board membership change over the last 10 years? What advice would you give to someone who has just joined their first board? How does Bill think about time allocation across the portfolio? What is the right ratio? 5.) How does Bill and Benchmark approach the element of partner selection today? What are the 5 core things that Bill looks for when adding to the partnership? What have Benchmark done that have allowed them to be so successful in generational transition? Why is an equal partnership so transformative when it comes to generational transition? Items Mentioned In Today’s Show: Bill’s Fave Book: Bill’s Most Recent Investment: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12506108

20VC: Inside UiPath, The World's Fastest Growing Startup, How The Best Leaders Approach Decision-Making & WhY Vulnerability Is Central To SuccessFul Leadership Today with Brandon Deer, VP of Operations & Strategy @ UiPath is VP of Operations & Strategy @ UiPath, one of the world's fastest-growing companies providing a complete software platform to help organizations efficiently automate business processes through robotic process automation. To date, UiPath has raised over $977m in funding from some of the best in the world including Sequoia, Accel, Meritech, IVP, CapitalG, Kleiner Perkins, Coatue and more. As for Brandon, prior to UiPath he spent 4 years as Vice President @ OpenView Partners where he made investments in Expensify, Logz.io, VTS and Pipefy to name a couple. Before OpenView, Brandon spent close to 4 years at Intuit in Strategy and Business Development. In Today’s Episode You Will Learn: 1.) How Brandon made his way from being a rising star in the world of venture with Openview to leading one of the fastest-growing companies in history in UiPath? What has been the most surprising element in making the transition from investor to operator? 2.) How does Brandon think about decision-making today? How does he determine what to spend time on vs what to delegate? What does he mean when he says, "you have to think whether it is rubber or crystal?" How does that ultimately guide decision-making? 3.) What does the UiPath software actually do? What is the relationship between RPA and AI? Where do they differ? Where do they intersect? Recently, RPA has seen a meteoric rise, is this sustainable over the long term? How does Brandon respond to the suggestion that RPA is replacing human jobs? What is the human and societal impact? 4.) How does Brandon think about vulnerability in leadership? Why does Daniel and Brandon's relationship work so well today? What has Daniel (Founder) taught Brandon about communicating that vulnerability the right way and authentically? What does Brandon advise founders in terms of being open to their vulnerabilities? 5.) What are the biggest challenges in scaling an organisation to the 1,000+ person organisation that UiPath is today? What breaks When does it break? How does one maintain culture wit such scale? What have been the challenges of building a truly global business from Day 1? How do they look to mitigate them? Items Mentioned In Today’s Show: Brandon’s Fave Book: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12477341

20VC: How To Think Through Portfolio Construction and The Business Model of VC, Why You Cannot Grow Ownership In Your Best Companies Over Time & How To Make The Space for Serendipity To Strike in VC with Adam D'Augelli, Partner @ True Ventures is a Partner @ , one of the West Coast’s leading early-stage funds with a portfolio including the likes of Fitbit, Peloton, Hashicorp, Tray.io, Ring, Automattic (makers of WordPress) and many more amazing companies. As for Adam, he has spent close to 10 years at True where he has led investments in Hashicorp, Ring, Splice and Namely, just to name a few. Prior to joining the world of venture with True, Adam was an instructor at The University of Florida in Business Finance. Before that Adam was the Founder of Perfect Wave Records, a donation-based record label - helping bands better monetize the relationships with their fans. In Today’s Episode You Will Learn: 1.) How Adam made his way into the world of venture with True having had a slightly unorthodox start as an Instructor at The University of Florida? 2.) How does Adam think about portfolio construction today with True? Is it still possible to get 20% ownership on first check? Does Adam believe you can build ownership in subsequent rounds? Does this mean we are seeing the end to rounds being co-led? What does Adam make of pre-emptive rounds? How do True respond to them today? 3.) How does True think about initial vs re-investment decision-making? How do the decision processes differ? Does Adam believe it is possible to stack rank companies and allocate capital accordingly? What is the right way to tell a founder you will not be re-investing? How does Adam think about risk maximisation at a company level? 4.) As a partnership, how does True look to create an environment of safety where both conviction and concerns can be expressed? What should partnerships not do? Why is attribution so dangerous to this EQ of the partnership? How does the partnership work with the companies at a company level? How does True view board seats? How does True think about when is the right time to roll off boards? 5.) What were Adam's biggest takeaways from leading Ring's seed to their acquisition by Amazon? How does Adam think about the importance of market vs the importance of people when investing? How does Adam think about company failure, post-mortems and subsequent next steps? Items Mentioned In Today’s Show: Adam’s Fave Book: Adam’s Most Recent Investment: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12415316

20VC: Unusual Ventures’ John Vrionis on Why We Need To Raise The Bar In Venture, Why Taking Multi-Stage Money At Seed Is Not In The Best Interest of Founders & Why To Be The Best, You Have To Specialise To Be The Best is the Founder and Managing Partner @ , the firm that is redefining seed investing and raising the bar for what entrepreneurs should expect from a seed investment firm. Prior to founding Unusual, John spent 11 years as a Partner @ Lightspeed where his investments included Mulesoft, AppDynamics, Nimble Storage and Heptio to name a few. Before Lightspeed John spent time in product management and sales @ Determina and Freedom Financial Network. In Today’s Episode You Will Learn: 1.) How did John make his way into the world of venture and come to be a Partner @ Lightspeed? How did that lead to his founding Unusual? How did his father's MS diagnosis change his mentality towards both investing and how he views the world? What were John's biggest takeaways from his 12 years with the Lightspeed partnership? 2.) Where does John feel the bar needs to be raised in venture? What does the current product not offer? What do seed-stage founders fundamentally need? How have Unusual structured the firm to provide this? How was the fundraise for John? What does John know post-closing that he wishes he had known at the beginning? What advice would John give to aspiring emerging managers? Why is LP diversity so important to John? 3.) Why does John believe taking multi-stage money at seed is not in the best interests of the founder? How does John explain this logically to founders? Does John agree with Semil Shah, "founders are voting with their feet and choosing multi-stage funds"? Why does John believe to be truly best in class, you have to specialise? Does this not go against the data of Benchmark, Sequoia, Founders Fund, all generalist funds, having the best returns? 4.) How does John think about being company vs being founder first? What does one do when alignment erodes between the interest of the firm and the interest of the founder? How does John look to build a relationship of trust and honesty with his founders? What works? What does not work? How does John feel about VCs being friends with their founders? 5.) What is the most challenging element of John's role today with Unusual? Who is the best board member John has ever sat on a board with? Why and what did he learn? What would John most like to change about the world of venture today? What would he like to remain the same? Items Mentioned In Today’s Show: John’s Fave Book: , John’s Most Recent Investment: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12329159

20VC: Why Raising A Mega-Round Makes Your Life Harder Not Easier, Why Your Board Is Not Your Boss and Lessons on Successful Board Management & The Biggest Breakpoints in Company Scaling with Emmanuel Schalit, Founder & CEO @ Dashlane is the Founder & CEO @ , the company that provides your all-in-one internet shortcut for passwords, payments and personal info. To date, Emmanuel has raised over $192m in funding for Dashlane from some of the best in the business including Jim Goetz @ Sequoia Capital, Rick @ Firstmark, Alex @ Bessemer and Habib @ Rho, just to name a few. As for Emmanuel, prior to founding Dashlane, he was the CEO @ CBS Outdoor in France and before that COO @ La Martiniere Group. In Today’s Episode You Will Learn: 1.) How Emmanuel made his way from CEO of 5,000+ people companies to founding Dashlane and changing the world of passwords and identification? How does Emmanuel asses his own risk profile moving from CEO of a large company to starting Dashlane? 2.) Is Emmanuel concerned by the excess capital available today? Why does Emmanuel believe that raising a mega-round makes your life as a founder harder, not easier? What specifically becomes harder? How does Emmanuel advise founders when it comes to burn and capital efficiency? How does Emmanuel think about when is the right time to pour fuel on the fire? 3.) Where does Emmanuel think that VCs do tangibly add real value? Where does Emmanuel believe that despite what some think, VCs do not add value in certain areas? What have been Emmanuel's biggest lessons of operating and managing a VC board? What does he advise founders starting out on this learning curve? 4.) What does Emmanuel believe are the core challenges of scale? What breaks at what specific points? How has Emmanuel seen himself scale in his role as CEO? What have been the most challenging element to scale into? How did Emmanuel get through them and what does he do to mitigate them now? Items Mentioned In Today’s Show: Emmanuel’s Fave Book: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12304376

20VC: BoxGroup's David Tisch on Whether Concentrated Investing At Seed Works, Do Founders Really Want Direct Feedback and Is It Good For Them & Why Consumer Social Is Interesting Again 12/02/2019

20VC: BoxGroup's David Tisch on Whether Concentrated Investing At Seed Works, Do Founders Really Want Direct Feedback and Is It Good For Them & Why Consumer Social Is Interesting Again is the Founder & Managing Partner @ , one of the leading early-stage firms in NYC with a portfolio that includes the likes of Flexport, RigUp, Ro, Glossier, Clearbit, PillPack and Plaid, to name a few. Recently they raised their first external capital with 2 separate vehicles totalling over $160m. David is also Professor and Head of Startup Studio @ Cornell Tech. Prior to BoxGroup, he was Managing Director of Techstars NYC and before that was an Executive Vice President @ KGB. In Today’s Episode You Will Learn: 1.) How David made his way into the world of early-stage investing? How he made the transition from prolific angel investor to raising $160m+ in external capital? Why did David feel now was the right time to raise external funding after 10 years of self-funding? How has taking on external capital changed his investing mindset? 2.) Many suggest that "concentrated seed investing does not work", how does David think about and assess portfolio construction? May others also suggest that, "seed investors are not company builders", does David agree with that? Does David believe investors can change the trajectory of a company? Where can they help the most? Where do many think they help but they actually do not? 3.) Why does David believe that founders do not speak openly about bad experiences with VCs? What have been David's biggest lessons on the right way to turn down an opportunity? Do founders really want direct and honest feedback? Is it actually damaging to give it to them? Why? How does David approach this? 4.) Why does David believe "consumer social is interesting again"? Why was it not interesting for a while? How does that mean David is approaching the category? What does David mean when he says, "for the first time ever there is no channel to arbitrage on the internet"? Is David concerned by the state of CACs today? How much attention does David pay to CAC/LTV in the early days? What are the key signals? Items Mentioned In Today’s Show: David’s Fave TV Show: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12244481

20VC: Why Startup Valuations Are Not As Overpriced As You Think, How To Determine Whether An Investor Is Truly Aligned To Your Mission and What 2 Traits Make The Truly Special Board Members with Jason Brown, Founder & CEO @ Tally is the Founder & CEO @ , the startup that allows you to pay off your credit card debt faster and save money. To date, Jason has raised over $92m for Tally from the likes of Mamoon @ Kleiner, Angela @ a16z, Nikhil @ Shasta and Aileen @ Cowboy just to name a few. As for Jason, prior to Tally, he spent 5 years as the Founder and CEO Kleiner Perkins backed, Gen110. Before that Jason founded Bask, a company providing both technical support and pro-active maintenance. In Today’s Episode You Will Learn: 1.) How Jason came to change the world of consumer finance with Tally having spent 5 years in the solar financing sector and even a year in venture? Given his prior entrepreneurial activities, does Jason agree with Joe Fernande @ JoyMode that "serial entrepreneurship is overrated"? 2.) Does Jason believe that founders should always be raising? What is the right way to truly determine whether an investor is aligned to your mission? What should you look for in how they behave and speak? How does Jason like to build relationships with investors pre-term sheet? Is Jason concerned by the compressed fundraising timelines today? 3.) Why does Jason believe that VC funded companies are largely not over-priced? What elements of the macro-economy does Jason attribute as the reason for the high valuations today? Why does Jason believe that we should not celebrate new fundraising? Is the celebration not good for the morale of the team? What should we celebrate instead? 4.) Why does Jason believe that the target for investors is they provide no value? What are you looking to avoid? What are the core ways an investor can damage the success of a company? What can founders do to truly extract the most from their investor base? Does Jason believe one should focus on the VC partner or the firm? Why? 5.) What does Jason believe makes the best board members? What advice would Jason give to new board members on how they can truly be the best board member? Why does Jason do onboarding sessions for all new board members? What does he look to instil in this process? What behaviour at the board should not be tolerated? How should the founder communicate this to their investor? Items Mentioned In Today’s Show: Jason’s Fave Book: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12220325

20VC: Why The Best Entrepreneurs Are Cockroaches, What Everyone Underestimates About Customer Acquisition & What You Don't But Need To Know About Payback Periods with Josh Buckley, Founder & Chairman @ Mino Games manages a $50m early-stage fund and as an angel has built a portfolio that includes the likes of Clearbit (Chairman), Rippling, Boom Supersonic, Lattice, Embark and many more incredible companies. Josh is also the Founder & Chairman @ Mino Games, the gaming studio he scaled to $20m in annual revenue and raising $40m in funding for the company. In Today’s Episode You Will Learn: 1.) How did Josh make his way into the world of startups at the age of just 15? How did that lead to becoming the youngest YC founder ever? 2.) What does Josh mean when he says, "the best entrepreneurs are cockroaches"? How does Josh think about capital efficiency today? Does Josh agree with Bill Gurley in stating the biggest challenge today is "the oversupply of capital"? How does Josh advise his portfolio today on raising big rounds? Capital efficiency? Burn rates? 3.) As both a fund manager and founder, what have been some of Josh's biggest takeaways from now investing in 100+ companies as an angel? How has investing impacted Josh's operating mentality? What are the benefits of angel investing? What are the potential dangers? What advice would Josh give to founders entering the world of angel investing? 4.) What are the biggest elements people underestimate when it comes to CAC? What have been Josh's biggest lessons on the volatility of CAC over time? How are we seeing the platforms evolve and develop their tech and pricing? How important is channel diversity to Josh? What is balanced? What is not? What have been Josh's biggest lessons when it comes to payback period and it changing over time? Items Mentioned In Today’s Show: Josh’s Fave Blog/ Newsletter: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12162851

20VC: Ash Fontana on The 5 Core Characteristics That Make Data Valuable, What VCs Can Learn From Italian Craftsmen and Howard Marks & The Importance of Vertical Integration In Scaling Today is a Managing Director @ , the fund that invests in AI-first companies with B2B business models. As for Ash, prior to Zetta he started the money side of AngelList, where, he launched online investing, created the first startup ‘index fund’. He also ran special projects like AngelList’s expansion into Europe and the UK. Simultaneously, Ash led syndicates and made investments in Canva, Mixmax and others. Before AngelList, Ash co-founded Topguest, a Founders Fund-backed company that built customer analytics technology and was ultimately sold in an 8 figure transaction 18 months after the company was founded. In Today’s Episode You Will Learn: 1.) How Ash made his way into the world of venture with AngelList and how that led to his joining Zetta today, investing exclusively in AI? What did Ash's time working on his family farm teach him about vertically integrated businesses? What were his biggest takeaways from AngelList and working alongside Naval? 2.) What does AI-first really mean to Ash? How crucial is it for companies to have proprietary datasets today? Are data moats truly defensible and real? What are the 5 characteristics that determine the level of defensibility of a dataset? How does Ash analyse the quality of a dataset? What does Ash do to determine if they are predictive of value? 3.) We often hear the term, "system of record", why is Ash so much more excited by the "system of intelligence"? Why is the basis of competitive advantage shifting from SaaS today as a model? How do the margin structure vastly differ when comparing AI-first companies to SaaS companies? How does that mean one should view capital efficiency? 4.) What does Ash believe drives business model quality? What are the commonalities in the business models of those that have made it big? Why does Ash believe it is difficult for incumbent companies to become AI-first? How difficult is it for incumbents to acquire smaller AI-first firms and integrate their policies and technology? 5.) Why does Ash love Howard marks and what has been his biggest learnings from studying him? How has Ash applied these learnings to his investing today? What has Ash also learned from the Italian masters of design? How has this study helped Ash as a VC? What has Ash optimised lately? What is Ash's favourite optimisation? Items Mentioned In Today’s Show: Ash’s Fave Book: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12074687

20VC: Why Speed Is The Biggest Differentiator a Founder Can Have, How To Hire Seasoned Tier 1 Talent To An Early Stage Startup & How To Start, Scale and Manage Remote Teams with Domm Holland, Founder & CEO @ Fast is the Founder & CEO @ , the world's fastest login and checkout with no more passwords, no more typing credit card details or shipping addresses. The special announcement today, Fast have just raised their seed round led by Jan Hammer @ Index, joined by Susa Ventures, Kleiner Perkins, Global Founders Capital and then angels including Nick Molnar, Founder @ Afterpay and proud to say I joined the round as an angel also. Prior to Fast, Domm was a Director @ Tap Tins, a network of smart tap-to-donate collection terminals. Domm was also the Founder & CEO @ Tow, an on-demand towing platform which transacted $50m in its first 4 years. In Today’s Episode You Will Learn: 1.) How Domm made his way from founding an on-demand towing company in Queensland, Australia to founding one of Silicon Valley's hottest new startups in Fast? 2.) What did Domm do in prior companies that worked and he will do again with Fast? What did not work and he will look to avoid? Does Domm agree with Joe Fernandez @ JoyMode in saying, "serial entrepreneurship is overrated"? What advice does Domm give to first-time founders? Where do they most often make mistakes? 3.) Over the last few years we have seen incredible innovation on the merchant side of payments with Stripe and Adyen but why does Domm believe we have seen no innovation on the consumer side? Why have large internet platforms not built it themselves? Does it have to be an independent 3rd party, external to Google, Facebook, Amazon etc? 4.) With the war for talent, rising rents and a lower standard of living, why did Domm choose SF as the base for Fast? How has the move been? What have been the biggest challenges? What would Domm advise founders contemplating moving to SF? How has Domm been able to hire some big hitter valley operators so early on? How does Domm think about equity sharing and optimising ESOP plans? 5.) Jan Hammer @ Index has discussed Domm's work mentality, so how does Domm structure his day? What does Domm do to ensure he optimises every minute? What work habits has Dom found to be most effective? What has not worked? How does Domm think about balancing speed and quality when executing today? Items Mentioned In Today’s Show: Dom's Fave Productivity Tool: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/12047687

20VC: Firstmark's Rick Heitzmann on The Rise of Pre-Emptive Rounds, His Biggest Learnings From The Pinterest Board, 2 Things VCs Can Do To Prepare Their Companies For The Downturn and Why Now Is A Good Time to Be Contrarian and Invest In Consumer is a Founder and Partner @ , one of the leading East Coast venture funds of the last decade with a portfolio including the likes of Airbnb, Pinterest, InVision, Shopify and Discord to name a few. As for Rick, he led the seed round for Pinterest and also led the deals from Firstmark in Ro, Riot Games, Draft Kings, Discord and Airbnb. Prior to founding FirstMark, Rick was an entrepreneur as a founding member at First Advantage which he helped grow and sell to First American (NYSE: FAF). Rick has been recognized by CB Insights and the New York Times as a Top 100 Venture Capitalist globally. In Today’s Episode You Will Learn: 1.) How Rick made his way into the world of venture and came to found one of NYC's leading venture funds in the form of Firstmark? 2.) How did seeing the booms and bust of the macro impact Rick's investment mentality today? With the impending crash, what 2 things does Rick advise managers need to prepare their portfolio by doing? Does Rick agree with Bill Gurley in saying, "the biggest challenge of today is the over-supply of capital"? 3.) How has Rick seen his style of investing change over the last 20 years? How does Rick think about price sensitivity today? How has that changed over the years? How has Rick seen himself change and evolve as a board member? What does Rick believe makes the best board members? What advice would Rick give to someone who has gained their first board seat? 4.) How does Rick think about the structure of the Firstmark portfolio today? How important does Rick believe it is to have temporal diversification within the portfolio? How does Rick think about optimising investment decision-making processes at Firstmark? Why does Rick believe, despite the negatives, that attribution is fundamentally important? 5.) Does Rick believe that we are in a consumer bubble today? What are the core elements that pique Rick's interest when analysing a consumer investment today? How does Rick think about CAC's scaling way faster and higher than anyone expected? Why does Rick believe the duopoly of FB and Google is now over? Why does Rick believe that true venture size exits can still occur in consumer? Items Mentioned In Today’s Show: Rick’s Fave Book: Rick’s Most Recent Investment: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/11986061

20VC: Why Pre-Product Market Fit Is About Systems Design Not Engineering, The Right Way For Leaders To Approach Wartime Leadership Today & A Guide To Recruitment Forward Planning with Ryan Denehy, Founder & CEO @ Electric is the Founder & CEO @ , the company that provides a world-class IT solution that's centralized, secure, and lightning-fast. To date, Ryan has raised over $37m in funding from some dear friends of the show in Rich @ GGV, Bessemer, Primary, Bowery, just to name a few. As for Ryan, he started his career at the tender age of 17 launching an action sports video production company, which was acquired just 4 years later. Ryan then spent 5 years at USA Today in numerous different roles. Following USA Today, Ryan started his second company, Swarm, acquired by Groupon just 3 years later. In Today’s Episode You Will Learn: 1.) How Ryan made his way into the world of startups from launching an action sports video production company at the age of 17? 2.) Having founded 2 prior companies, would Ryan agree with Joe Fernande @ JoyMode in saying that "serial entrepreneurship is overrated"? What did he do right in the first 2 companies that he would look to do again? What did not work that he is avoiding? Where does Ryan most often see first-time founders make mistakes scaling? 3.) How does Ryan think about and assess wartime leadership? What is the right leadership style and approach to battle through the really tough times? Ryan's investors talk of his speed of execution, how does Ryan balance the speed with the quality when it comes to execution? How has Ryan seen both his role and the way in which he executes it change with the scale of the company and of himself? 4.) How does Ryan thnk about and assess forward planning when it comes to recruitment? How should this recruitment planning align to fundraising? Why must it start before the fundraise? How does Ryan think about levelling up individuals internally vs hiring external candidates? How does Ryan think about and present internal expectation setting? Items Mentioned In Today’s Show: Ryan’s Fave Book: As always you can follow , and on Twitter here! /episode/index/show/thetwentyminutevc/id/11961056

20VC: Inside The Mind of A Leading LP: How LPs Evaluate New Fund Managers on Everything from First Meeting to Portfolio Construction To Fees and Carry with Lisa Edgar, Managing Director @ Top Tier Capital Partners is a Managing Director @ , one of the leading venture fund of funds over the last decade. Included in their stellar fund portfolio is the likes of Index, Initialized, True Ventures, a16z and Boldstart, to name a few. Prior to Top Tier, Lisa was part of the asset management team at WR Hambrecht + Co focusing on new and emerging private equity funds. Before that, Lisa spent ten years at Horsley Bridge. In Today’s Episode You Will Learn: 1.) How did Lisa make her way into the world of investing in funds and how did that lead to her becoming Managing Director at one of the leaders, Top Tier? 2.) Lisa has seen the boom and bust of the macroeconomy twice now, how has that impacted her mindset today when investing in funds? What have been the most prominent changes in the venture ecosystem that Lisa has seen over the last 20 years? What changes have been good? What changes have been bad? 3.) What is the best way to get in the room with LPs? Does it have to be through warm intro? What are the signs for the GP that that first meeting went well? If an LP does not respond to emails, does that mean they don't want to do it? How does Lisa and Top Tier structure the investment decision-making process? How does that differ when re-investing in existing managers? Is it worth it for first-time funds to pitch institutions for fund 1 when they know they will not invest in the fund? 4.) How does Lisa think about GP commits today? How does Lisa look at what is reasonable and what is required? Is it individual and context-based? How does Lisa feel about different carry structures? Are kickers when past a certain return profile amenable to LPs? 5.) Lisa has seen some of the best emerging managers in the US over the last decade, what learnings does she have from them in terms of what separates the good from the great? How do they think about partnership dynamics? How do they think about firm culture? How do they think about generational transition? Items Mentioned In Today’s Show: Lisa’s Fave Book: Lisa’s Most Recent Investment: As always you can follow and on Twitter here! /episode/index/show/thetwentyminutevc/id/11904239

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

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