20VC Roundtable: Why Early Stage Founders Should Not be Investing, Why Great Founders Have Low EQ, How the Structure of VC Firms Will Change, Will Founder-Led Funds Compete with Sequoia & Is Investing a Team Sport?

Geoff Ralston is President @ Y Combinator, the world's leading accelerator with a portfolio that includes the likes of Stripe, Airbnb, Dropbox, Coinbase, Instacart, DoorDash, Flexport and so many more. As for Geoff, he started his career running engineering at Four11, where he built RocketMail, which in 1997 became Yahoo! Mail. At Yahoo! Geoff worked in engineering, then ran a business unit, then became Chief Product Officer. After Yahoo! he was CEO of Lala, which was acquired in 2009 by Apple. Post Lala, Geoff then co-founded the world's first educational technology accelerator, Imagine K12 which funded dozens of edtech companies including ClassDojo, Remind, and Panorama Education. Imagine K12 merged with YC in 2016. In Today's Episode You Will Learn: 1.) How Geoff made his way into the world of technology and startups, came to found Imagine K12 and how that led to becoming President @ Y Combinator today? 2.) What were Geoff's biggest takeaways from seeing the boom and bust of the macro environment in the dot com and 2008? How did those times impact both his operating and investing mentality? Why does Geoff believe 2000 was "purifying"? Why can the same not be said for 2008? How was 2008 so different? 3.) Frederic Kerrest @ Okta said: "it is 70% market, 20% team and 10% product", would Geoff agree with this weighting? How has his weighting changed over time? YC has "10 Minute Meetings", how can YC really determine whether someone is investable in 10 mins? How does Geoff think about the hailed VC term, "pattern matching"? Why does Geoff believe you lose as an investor if you fall back on "profiles"? 4.) Geoff has worked with 100s of founders in the idea validation stage, how does Geoff know when a founder has the right idea? How does Geoff think about the balance between mission and vision but then also being realistic about when something is not working? When do you quit? Why is the decision internal not external? What is the most important perspective any investor can give a founder? 5.) How does Geoff think about the coined term "product-market fit" and how does he analyse it in terms of retention and growth? If they have some signs of it, how should founders think about when is the right time to raise their first round? How does Geoff think about the benefits for founders of convertibles and now SAFE's? What does Geoff believe will be the future of legal round mechanics? Items Mentioned In Today's Show: Geoff's Fave Book: Titan: The Life of John D. Rockefeller As always you can follow Harry, The Twenty Minute VC and Geoff on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

27 Mai 201934min

Mathilde Collin is the Co-Founder & CEO @ Front, reinventing the email inbox with new workflows and efficient collaboration so people can accomplish more together. To date, Mathilde has raised over $79m in VC funding with Front from some of the best in the business including Bryan Schreier @ Sequoia, Initialized, Uncork Capital, Boldstart and individuals including Andrew Chen, Elad Gil, Ray Tonsing the list goes on. With 4,500+ customers, and 100+ employees, in Paris, San Francisco and Amsterdam, Front is one of the fastest growing companies in SaaS and Mathilde has become a thought leader for the next generation of SaaS CEOs, read more on her blog here. In Today's Episode You Will Learn: 1.) How Mathilde made her way from product manager in Paris to founding one of the hottest and fastest growing companies in the world of SaaS in the form of Front? 2.) What does Mathilde mean when she says, "I would choose discipline over vision any day of the week"? What does discipline really mean to Mathilde? Why is it a priority in the early days? How can a VC stress test and determine the level of discipline a founder has in first meetings? What are the signs or leading indicators? 3.) Communications: Investor Updates: What is Mathilde's biggest advice to founders when it comes to investor updates? What should they contain? How often should they go out? How should founders ask for help in updates? Where do founders often make mistakes? Revenue Updates: Why does Mathilde do revenue updates with the team? Is there a danger of being too transparent? What are the benefits of this transparency? What is the structure of the update? Who is privy to it? Direct Reports: How does Mathilde communicate with her direct reports? Why does Mathilde believe that CEOs should have their calendar public? What is the right cadence for these direct reports? 4.) How does Mathilde approach and think about fundraises with Front today? How can founders know when is the right time to raise? How does Mathilde think about building relationships with investors when she is not raising? How transparent should founders be when they are not raising? What are Mathilde tips for always overshooting her numbers? How does Mathilde conduct DD on potential investors in the company? Items Mentioned In Today's Show: Mathilde's Fave Book: The Power of Now: A Guide to Spiritual Enlightenment As always you can follow Harry, The Twenty Minute VC and Mathilde on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

24 Mai 201933min

Jeff Housenbold is a Managing Partner @ Softbank Vision Fund, the leading and most influential firm in the venture space investing more than $93 billion in the businesses and technologies they believe will enable the next stage of the information revolution. To date, Jeff has backed the likes of OpenDoor, DoorDash, Wag, Clutter, Brandless and Katerra just to name a few. Prior to Softbank, Jeff spent 11 years as President and CEO @ Shutterfly, during his tenure the company enjoyed incredible growth with the growth of the team from 103 to 2,600 employees. In the past, Jeff has sat on the board of Caesers Entertainment (the world's largest casino entertainment company), Groupon and Chegg and is currently a member of the Board of Trustees of Carnegie Mellon University. In Today's Episode You Will Learn: 1.) How Jeff made his way from being President and CEO of Shutterfly for 11 years to writing $200m-2Bn checks as Managing Partner @ Softbank Vision Fund? 2.) We have Wag on the small end and Uber on the high end, so how does Softbank think about portfolio construction and insertion point today? Blended, at what stage would Softbank like their capital to be most concentrated? Does Jeff believe that ownership is largely built on the first check or built over time? 3.) What does the internal investment-decision making process look like for Softbank? How does this decision-making process change when considering reserve allocation? How does Softbank think about and approach reserves given their later entry into companies? Given the size of check being written, what does diligence look like in the standard process for Softbank? 4.) Given the forthy pricing environment today, how does Jeff assess his own price sensitivity? Does this differ depending on the stage of entry? With many suggesting Softbank have extended the period of privatisation for companies, how does Jeff and the team think about liquidity? How does Jeff think about the future of secondaries for seed managers and angels? 5.) Question from Eric Wu @ Opendoor: How does Jeff think about and analyse the opportunity in fragmented categories? What is the bottoms up thought process to this thesis? Speaking of Opendoor, how does Jeff most like to work with the founders he backs? How does Jeff think about he allocates his time across the portfolio? Items Mentioned In Today's Show: Jeff's Fave Book: The Fountainhead Jeff's Most Recent Investment: Katerra As always you can follow Harry, The Twenty Minute VC and Jeff on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They've built the world's largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they're built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you're taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add "company savior" to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

20 Mai 201933min

Jon Dishotsky is the Founder & CEO @ Starcity, the startup on a mission to make cities more affordable to everyone allowing you to live with great people in the city you love. To date, Jon has raised over $28m in funding for Starcity from the likes of Social Capital, Y Combinator, Bullpen Capital, NEA and Kima Ventures in Paris, just to name a few. Prior to founding Starcity, Jon did over 3M square feet of commercial real estate transactions for clients including Optimizely, Cruise Automation, Weebly, Zenefits and many more. Before that he spent 8 years at the prestigious Cushman & Wakefield. Jon is also an active angel investor with investments in the likes of Remote, Fond and Savvy. In Today's Episode You Will Learn: 1.) How Jon made his way from doing real estate transactions for clients including YC to being one of the hottest prop tech startups making cities affordable with Starcity? 2.) Why did it take so long for the venture ecosystem to get excited by the rise of proptech? What was the catalyst? When advising VCs, how do you advise them to get comfortable investing in these heavy asset, non-lean startup businesses? What are the biggest mistakes investors make when analysing proptech? 3.) What were some of Jon's biggest takeaways from his time at YC? How does Jon advise other founders looking to get into YC today? When it comes to investor selection, in what cases would Jon take a lower valuation against other offers? How does Jon advise founders on investor selection? What questions should they ask? Why is it like hiring? What are the common mistakes that Jon sees founders make when selecting investors? 4.) How does Jon advise founders when it comes to improving the quality of their mental health? Where do Jon struggle? How does Jon engage with social media knowing the psychological effects it has? What have been some major breakthroughs for him? Why does Jon believe having kids has made him a better founder? Why does Jon believe that older entrepreneurs are actually more successful than younger founders? 5.) What is Jon's biggest advice to founders when it comes to building relationships with VCs? Should founders "always be raising"? How transparent should founders be with VCs both in the relationship building process and the fundraise itself? As always you can follow Harry, The Twenty Minute VC and Jon on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

17 Mai 201931min

Mamoon Hamid is a Partner @ Kleiner Perkins, one of Silicon Valley's most prestigious venture firms counting Google, Airbnb, Amazon, Spotify, Square and many more $Bn companies among their portfolio. As for Mamoon, he has invested in and served on the boards of some of the most innovative software companies of recent times including Box, Figma, Intercom, Netskope, Slack and Yammer. Prior to joining Kleiner Perkins, Mamoon was a Co-Founder and General Partner at Social Capital and before that Mamoon was a Partner at U.S. Venture Partners (USVP), where he spent six years. In Today's Episode You Will Learn: 1.) How did Mamoon make the transition from electrical engineer to VC and how did that translate to his role today as Partner @ KPCB? 2.) With Kleiner's new $600m early stage fund, Mamoon had a blank canvas, how does Mamoon think about portfolio construction from a bottom-up perspective? Why is that strategy optimal? How important does Mamoon believe it is for VCs to have a sector focus today? What does he mean when he says, "VCs need to have both majors and minors"? 3.) In today's heated early stage ecosystem, how does Mamoon analyse and reflect on his own price sensitivity? What deal has changed the way he thought about price and he either regrets not paying it or is thrilled he did pay it? How does Mamoon feel about the compressed fundraising timelines we are seeing today? Is this a concern? 4.) How does KPCB think about reserve allocation with the new $600m fund? How do they approach the opportunity cost of dollar deployment in terms of when to stop following on? How does the investment decision-making process change when comparing initial to reserve investment? 5.) Where does Mamoon believe that founders need the most help from their venture investors? Where does Mamoon see the commonalities in founders struggles to scale themselves with their role? What are the biggest mistakes Mamoon sees being made when initial traction has been hit and they start to scale? How can founders avoid these? 6.) How does Mamoon think about and address what it takes to build the most successful and efficient venture partnership? How does Mamoon compare this to a basketball team? Is venture really a team sport today? what are some of the biggest challenges in scaling venture firms over time? Items Mentioned In Today's Show: Mamoon's Fave Book: Principles: Life and Work by Ray Dalio Mamoon's Most Recent Investment: Viz.ai As always you can follow Harry, The Twenty Minute VC and Mamoon on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

13 Mai 201932min

Michele Romanow is the Founder & CEO @ Clearbanc, the startup that provides entrepreneurs capital to grow without giving up a piece of their company. In 2019 alone, Clearbanc plans to invest $1B in 2,000 companies. To fund these ambitious plans, they have backing from some of the best in the business including Founders Fund, Santi @ Emergence, Social Capital, Precursor Ventures and Y Combinator just to name a few. As for Michele, prior to Clearbanc, she founded SnapSaves, a leading mobile savings platform that was acquired by Groupon. Before Snapsaves, Michele founded Buytopia, one of Canada's leading e-commerce companies with over 2.5m customers. If that was not enough Michele is also a Dragon on Dragons Den Canada, the youngest dragon ever. In Today's Episode You Will Learn: 1.) How Michele made her way from serial entrepreneur with exits to Groupon and being a Dragon on Dragons Den to changing the way we fund today's businesses with Clearbanc? 2.) Why does Michele fundamentally believe we need to rethink the way we fund our businesses? Why does giving away equity to buy FC and Google ads not make sense? What is the solution? What types of business with what types of revenue does this work for? Why does Michele believe we need to fundamentally stop celebrating fundraisings? 3.) So if Clearbanc lends on repeatable revenue from Google and Facebook, how does Michele think about the volatility of CACs we see as businesses progress? Is Michele concerned by the large incumbents pushing up CACs on traditional platforms? Investors can also be wise strategic advisors, how does Michele think about the potential loss of these advisors and board members with an alternative financing mechanism? 4.) From Clearbanc's data, what have been the big learnings on how venture is currently distributed across the US? To what extent does Michele believe that unconscious bias pervades into the decision-making of much of venture? What have Clearbanc discovered in terms of the diversity of the founders they back, purely through objective data analysis of their businesses? 5.) How does Michele respond when shit hits the fan? What is her coping mechanism? How would Michele advise young founders today in coping with tough times? What were Michele's lessons from her first sturgeon caviar business not being a success? Items Mentioned In Today's Show: Michele's Fave Book: Little Black Stretchy Pants As always you can follow Harry, The Twenty Minute VC and Michele on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They've built the world's largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they're built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you're taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add "company savior" to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

10 Mai 201931min

Brendan Wallace is the Co-Founder and Managing Partner @ Fifth Wall, the fund with the core thesis being the physical world around us is colliding with technology. Within their portfolio is the likes of Lime, OpenDoor, Clutter, ClassPass, Lyric and Hippo just to name a few. As for Brendan, before co-founding Fifth Wall he co-founded Identified, a data & analytics company focused on workforce optimization that was acquired by Workday in 2014. Prior to that, Brendan co-founded Cabify, the largest ridesharing service in Latin America. If that was not enough, Brendan has been an active angel investor having led over 60 angel investments including Bonobos, Dollar Shave Club, Lyft, SpaceX, Clutter, Philz Coffee and Zenefits. In Today's Episode You Will Learn: 1.) How Brendan made his way from founding the largest ridesharing platform in Latin America to changing the face of early stage real estate and consumer retail investing with Fifth Wall? 2.) What is really going on in retail today? Is "retail apocalypse" a fair term to give to the landscape today? What formats does physical retail no longer work for? What is it perfect for? How does Brendan think about the distribution of physical retail for emerging brands? Will they need 1,000s of stores or is the 1,000 store brand era over? 3.) Why do digitally native brands fundamentally need retail? How much of consumer US spend relies on physical retail still today? When do these DNVB's need to expand into physical retail? From speaking to DNVB CEO's what are the most common challenges they face when making the expansion? 4.) How does expanding into physical retail change the game in terms of customer acquisition for DNVBs? At what point do DNVBs hit the invisible asymptote where acquiring customers through traditional online channels is no longer efficient? How have Amazon impacted the CACs for DNVBs in recent years? 5.) Given the consumer retail focus of the fund, one would expect a lower loss ratio, is it right to assume the lower loss ratio? How does Brendan think about portfolio construction with the fund? How does reserve allocation differ when investing in physical retail vs pure software plays? Is Brendan concerned by the lack of downstream capital in the physical retail space? 6.) How does Brendan assess outcome potential when comparing physical retail to pure software plays? Why des Brendan believe we will see a ton of intermediate outcomes? How does this change the type of entrepreneur that Brendan looks to back with the retail fund? Items Mentioned In Today's Show: Brendan's Fave Book: The Great Gatsby Brendan's Most Recent Investment: Heyday As always you can follow Harry, The Twenty Minute VC and Brendan on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They've built the world's largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they're built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you're taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add "company savior" to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

6 Mai 201937min

Frederic Kerrest is the Founder & COO @ Okta, the independent and neutral platform that securely connects the right people to the right technologies at the right time. To date Frederic has raised over $415m with Okta from some of the best in the business including Doug Leone @ Sequoia, Marc Andreessen @ a16z, a dear friend of the show in Mike Maples @ Floodgate, Aneel Bhusri @ Greylock and Vinod Khosla, just to name a few. Okta IPO'd in April 2017 at a stock price of $17, today they sit at $102. Before founding Okta, Frederic enjoyed roles with Hummer Winblad on the other side of the table as a VC and also at Salesforce and Sun Microsystems on the operations side. In Today's Episode You Will Learn: 1.) How Frederic came to found the now public Okta having spent time with Salesforce, Sun Microsystems and Hummer Winblad as a VC? 2.) What about an idea makes it worth pursuing and investing in? Does Frederic agree with the advice he was given, "it is 70% market, 20% people and 10% product"? When evaluating a market, what characteristics make for the most attractive markets? How does Frederic think about insertion points into markets? How does he evaluate market adjacencies? Why is it so good to be a monopolist in a small market? 3.) What were some of the hardest times Okta went through? How does Frederic determine the balance between vision and realism? How does Frederic as the leader personally deal with these challenging times? How can a founder determine from their hiring process whether they have product-market fit? What were the key turnings points that contributed to Okta's success? What did you have to get right to keep scaling? 4.) A little birdy told me there was an amazing story behind the a16z investment, what is that story? How did Frederic meet Marc and Ben and how did his relationship with them evolve over time? When analysing his investor base, where did each add real strategic value? What advice does Frederic give to founders today on the theme of investor selection? What should the core considerations be? Items Mentioned In Today's Show: Frederic's Fave Book: Battle Cry of Freedom: The Civil War Era As always you can follow Harry, The Twenty Minute VC and Frederic on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

3 Mai 201936min