20VC: 500 Startups' Dave McClure on Whether Unicorns Are Necessary For Venture Returns & Why Ownership Is Not The Math To Think About When Investing

Rishi Garg is a General Partner @ Mayfield Fund, where he focuses on new media platforms, disruptive financial services and new marketplaces. Prior to joining Mayfield, Rishi was as Vice President of Corporate Development and Strategy at Twitter where he led the company's most active M&A program, including the acquisitions of Periscope, TellApart, TapCommerce, and many others. Prior to Twitter, Rishi was the first Head of Corporate Development at Square. Rishi was also the Founder of a leading venture-backed startup, FanSnap and has also held roles at Google, Highland Capital Partners and Morgan Stanley. In Today's Episode You Will Learn: 1.) How Rishi made his way into VC following time at Twitter and Square? 2.) How does Rishi look to analyse the state of co-founder relationships? What questions get to the core issues? What are the signs that encourage and worry Rishi? 3.) To what extent does a co-founder leaving the company concern Rishi? In what circumstance is this understandable? How should this process be played out? 4.) How much of a role should VCs play post-investment in the relationship of the founders? What are the dangers of this? How should VCs balance helpful and over involved? 5.) Why is Rishi anti the rise of the very large Series? What are the inherent dangers of this? How does he convey this concern to founders? Items Mentioned In Today's Show: Rishi's Fave Book: The Tibetan Book of Living & Dying, Malcolm X Rishi's Fave Blog or Newsletter: Wait But Why As always you can follow Harry, The Twenty Minute VC, Rishi on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner's sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com Cirrus Insight is a plugin for sales pros who use Gmail and Outlook. It automatically updates activities in Salesforce so you don't have to. It was named #41 on the Inc. 500 list of fastest-growing companies, and it has more than 1,700 customer reviews on the Salesforce AppExchange. Today, it serves over 150,000 sales people across 5,000 organizations using Gmail, Outlook, iPhone, iPad, and Android. Cirrus Insight is perfect for sales, support, and success teams who want to save time, schedule 3x more appointments, track email opens and much more with Salesforce information at their fingertips in the inbox. www.cirrusinsight.com/20VC

18 Jan 201731min

Tim Chang is a Managing Director @ Mayfield Fund and Tim was referred to me by many other VCs as 'the fittest man in silicon Valley', notable tech publications even write it. His eclecticness does not stop there as he is also a musician in 3 bands and a serious body hacker. As for his investments, he has had AdChina (acquired by Alibaba), Playdom (acquired by Disney) and Basis (acquired by Intel) just to name a few. Prior to Mayfield, he spent time at notable institutions including General Motors and Norwest Venture Partners. It is not only us that appreciate Tim's skills though as he has also been named to 'Top 100 Innovators' on Forbes Midas List for 2 years running. In Today's Episode You Will Learn: 1.) How Tim made his way into the wonderful world of VC following Stanford Business School? 2.) How did Tim's perspective of starting VC around 9/11 shape his perspective coming into the industry? Why does Tim believe you need to see multiple cycles to be a good VC? 3.) Where are theWhy does Tim believe that startups need to be better capitalised than they currently are in the early days? Why does Tim argue for the existence of the Series B Crunch? 4.) How does Tim view the creation of a business model for machine learning? What are the 2 elements that founders need to consider before deciding in a pricing mechanism? 5.) How does Tim evaluate machine learning startups today in the plethora that have been created over the last few years? How does Tim determine true machine learning talent? Items Mentioned In Today's Show: Tim's Fave Book: Nexus Tim's Fave Blog or Newsletter: Wait But Why Tim's Most Recent Investment: Next Entertainment As always you can follow Harry, The Twenty Minute VC, Tim on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner's sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com Cirrus Insight is a plugin for sales pros who use Gmail and Outlook. It automatically updates activities in Salesforce so you don't have to. It was named #41 on the Inc. 500 list of fastest-growing companies, and it has more than 1,700 customer reviews on the Salesforce AppExchange. Today, it serves over 150,000 sales people across 5,000 organizations using Gmail, Outlook, iPhone, iPad, and Android. Cirrus Insight is perfect for sales, support, and success teams who want to save time, schedule 3x more appointments, track email opens and much more with Salesforce information at their fingertips in the inbox. www.cirrusinsight.com/20VC

16 Jan 201726min

Maran Nelson is the Co-Founder & CEO @ Clara Labs, the truly human interface that uses conversational intelligence trained on high-quality data to schedule your meetings. They have secured funding from some of the best in the business including previous guest Kent Goldman @ Upside Partnership and Greg Brockman, Founder of the prestigious OpenAI. As for Maran, she is also the Founder of Interact, a community of 100 young makers and technologists coming together for an annual retreat in Tahoe. In Today's Episode You Will Learn: 1.) How did Maran come to found one of the hottest AI startups of the day in Clara Labs? 2.) What is the right way to think about a digital assistant? How does Maran think consumer expectations and behaviours will change towards them in the coming years? 3.) Question from Shivon @ Bloomberg Beta: How does Maran think about building an AI company for the long term? How does Clara look to build scalable and transparent feedback loops? 4.) Why is Maran so bullish on the conversational interface? To what situation does this interface lend best? What other verticals and applications could this have in the future? 5.) Does Maran think that humans will always be needed in this process? At what stage will they become obsolete? Items Mentioned In Today's Show: Maran's Fave Book: East of Eden by John Steinbeck As always you can follow Harry, The Twenty Minute VC and Maran on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner's sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com Cirrus Insight is a plugin for sales pros who use Gmail and Outlook. It automatically updates activities in Salesforce so you don't have to. It was named #41 on the Inc. 500 list of fastest-growing companies, and it has more than 1,700 customer reviews on the Salesforce AppExchange. Today, it serves over 150,000 sales people across 5,000 organizations using Gmail, Outlook, iPhone, iPad, and Android. Cirrus Insight is perfect for sales, support, and success teams who want to save time, schedule 3x more appointments, track email opens and much more with Salesforce information at their fingertips in the inbox. www.cirrusinsight.com/20VC

13 Jan 201731min

Emily Melton is partner at DFJ, where she focuses on consumer and mobile technology, as well as healthcare technologies and marketplaces. Emily has made investments in the likes of BetterUp, Elation Health, Livongo, Redfin, Shift, and Wellframe. Early in Emily's career, she sourced investments in Box (NYSE: BOX), Meebo (Google), Kudo (Google), RichRelevance, and Flux (MTV Networks). She was also an advisor to Pulse Network (LinkedIn), Healthtap, and Poshmark. In Today's Episode You Will Learn: 1.) How Emily made her way into the wonderful world of VC following her meeting with Tim Draper? 2.) How does Emily view the importance of pattern recognition? Why does Emily believe that you should not invest from patterns? What is the difference between a pattern and an investing fad? 3.) Why does Emily hate analogies? Why does she believe it is simplistic thinking? How can this be mitigated for startup founders in describing their company? 4.) How does Emily view the portfolio approach to risk in venture? What questions need to be asked to determine the potential outcome of the business? 5.) Why does Emily get concerned by the rise of the 'celebrity investor'? How can investors build their brand in the proliferated world of early stage startup investing? Items Mentioned In Today's Show: Emily's Fave Book: Mindset by Carol Dweck, A Theory of Justice by John Rawls Emily's Most Recent Investment: BetterUp As always you can follow Harry, The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner's sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com Cirrus Insight is a plugin for sales pros who use Gmail and Outlook. It automatically updates activities in Salesforce so you don't have to. It was named #41 on the Inc. 500 list of fastest-growing companies, and it has more than 1,700 customer reviews on the Salesforce AppExchange. Today, it serves over 150,000 sales people across 5,000 organizations using Gmail, Outlook, iPhone, iPad, and Android. Cirrus Insight is perfect for sales, support, and success teams who want to save time, schedule 3x more appointments, track email opens and much more with Salesforce information at their fingertips in the inbox. www.cirrusinsight.com/20VC

11 Jan 201735min

Josh Stein is Partner @ DFJ where his current board responsibilities include Box (NYSE: BOX), Chartbeat, LaunchDarkly, LendKey, SugarCRM, and previous guests with me on SaaStr in Periscope and Talkdesk. He is also actively involved with the firm's investments in AngelList, Doximity and Twilio (NYSE: TWLO) just to name a few. Prior to joining DFJ, Josh was a VP at Telephia, where he managed a group providing strategic analysis and information to the nation's largest wireless carrier. Previously, Josh was a co-founder for ViaFone (NYSE: SY), a DFJ portfolio company and a leading provider of wireless enterprise applications. Josh met the DFJ team when the firm co-led ViaFone's Series A investment. In Today's Episode You Will Learn: 1.) How Josh made his way from the world of operations to Partner @ DFJ? 2.) How does Josh analyze the VC/ Founder fit? How does Josh look to build trust and transparency in that relationship? What is an example of how Josh has changed his style to fit the character of an entrepreneur? 3.) Question from Greg Sands: What did Josh see in the early days of Box with a young Aaron Levie, what was it that made him so excited? 4.) Question from Mamoon Hamid @ Social Capital: Looking at Box today, what will it take for Box to 10x their value? What needs to happen in the market? What needs to happen to the product roadmap? 5.) Question from Jason Lemkin @ SaaStr: How is it that we are seeing companies like TalkDesk and Twilio grow at a rate never seen before in today's SaaS environment? Items Mentioned In Today's Show: Josh's Fave Blog: TermSheet Josh's Fave Book: Insanely Simple: The Obsession That Drives Apple's Success Josh's Most Recent Investment: LaunchDarkly As always you can follow Harry, The Twenty Minute VC and Josh on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner's sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com Cirrus Insight is a plugin for sales pros who use Gmail and Outlook. It automatically updates activities in Salesforce so you don't have to. It was named #41 on the Inc. 500 list of fastest-growing companies, and it has more than 1,700 customer reviews on the Salesforce AppExchange. Today, it serves over 150,000 sales people across 5,000 organizations using Gmail, Outlook, iPhone, iPad, and Android. Cirrus Insight is perfect for sales, support, and success teams who want to save time, schedule 3x more appointments, track email opens and much more with Salesforce information at their fingertips in the inbox. www.cirrusinsight.com/20VC

9 Jan 201725min

Henry Ward is the Founder & CEO @ eShares, the No 1 cap table management platform providing equity management, 409A valuations and liquidity all in one place. They are backed by leading investors and past guests including USV, SV Angel, Spark Capital, Semil Shah, Manu Kumar, Tim Draper and Kamal Ravikant, just to name a few. Prior to eShares, Henry was Founder @ SecondSight, the first registered investment advisor to go direct to your brokerage and improve your portfolio. In Today's Episode You Will Learn: 1.) How Henry made his way into the world of startups and came to found eShares? 2.) How does Henry challenge the notion that investors should have such high fail rates? How does Henry believe investors can build a strong and sustainable portfolio without home runs? 3.) Why does Henry believe that investors will never accept market risk? How much of a role does Henry believe herd mentality plays in the VC ecosystem? 4.) How does Henry view the increasing exit horizons for startups? Is this a problem? How can we create liquidity options pre large exits? 5.) How does Henry view the role of regulation in private markets? How does this differ to public markets? What would Henry like to see change in the VC ecosystem? Items Mentioned In Today's Show: Henry's Fave Blog: Hacker News Henry's Fave Book: The Essays Of Warren Buffett As always you can follow Harry, The Twenty Minute VC and Henry on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner's sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com Cirrus Insight is a plugin for sales pros who use Gmail and Outlook. It automatically updates activities in Salesforce so you don't have to. It was named #41 on the Inc. 500 list of fastest-growing companies, and it has more than 1,700 customer reviews on the Salesforce AppExchange. Today, it serves over 150,000 sales people across 5,000 organizations using Gmail, Outlook, iPhone, iPad, and Android. Cirrus Insight is perfect for sales, support, and success teams who want to save time, schedule 3x more appointments, track email opens and much more with Salesforce information at their fingertips in the inbox. www.cirrusinsight.com/20VC

6 Jan 201725min

Phil Libin is Managing Director @ General Catalyst and Founder and Executive Chairman @ Evernote. At Evernote, Phil took the company from idea generation to productivity powerhouse allowing millions of users around the world to remember everything and in the meantime, providing Evernote with over $160m in VC funding from some of the very best including Sequoia Capital. Now in the world of VC, Phil has a particularly fondness towards all things bots, a theme we discuss heavily today. Phil has also made several angel investments in the likes of Gusto, TellApart and Binary Thumb just to name a few. In Today's Episode You Will Learn: 1.) How Phil made his way from Founder @ Evernote to Managing Director @ General Catalyst? 2.) Niko Bonatsos, Managing Director @ General Catalyst asks: What were your biggest takeaways from your time with Evernote that lend to you being a better investor? What are the biggest surprises about the move into VC? 3.) Why have we seen an explosion of hype and excitement around the bot space over the past year? What was the catalyst for the rise of the bot? 4.) Why are we not there yet with bots? Should all be conversational? How does the infancy of messaging platforms affect the rise of bots? What unsolved technical challenges remain? 5.) Will the transition to bots and conversational interfaces represent a major point of disruption or more of an evolution in the interface paradigm? Items Mentioned In Today's Show: Phil's Fave Blog: The Economist Phil's Fave Book: The Three Body Problem Phil's Most Recent Investment: Sunflower Labs As always you can follow Harry, The Twenty Minute VC and Phil on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner's sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com Cirrus Insight is a plugin for sales pros who use Gmail and Outlook. It automatically updates activities in Salesforce so you don't have to. It was named #41 on the Inc. 500 list of fastest-growing companies, and it has more than 1,700 customer reviews on the Salesforce AppExchange. Today, it serves over 150,000 sales people across 5,000 organizations using Gmail, Outlook, iPhone, iPad, and Android. Cirrus Insight is perfect for sales, support, and success teams who want to save time, schedule 3x more appointments, track email opens and much more with Salesforce information at their fingertips in the inbox. www.cirrusinsight.com/20VC

4 Jan 201722min

Charlie O'Donnell is the Founder and Sole Partner @ Brooklyn Bridge Ventures, the first venture capital fund based in Brooklyn, who manage $23m across 2 funds. Prior to founding Brooklyn Bridge, Charlie worked at the prestigious First Round Capital, with the likes of Josh Koppelman and Union Square Ventures with Fred Wilson. If that wasn't enough Charlie is one of only a dozen to be named to Business Insider's 100 Most Influential People in NY Tech five or more times and has served on the founding board of the New York Tech Meetup and is one of the group's first 100 members. His blog, This is Going to Be BIG!, is one of the ten most widely read VC blogs in the country with over 8,000 readers. In Today's Episode You Will Learn: 1.) How Charlie made his move from college to venture and then struck out on his own from USV? 2.) Charlie has previously said that 'venture capital is humbling'. How does Charlie look to construct his portfolio with Brooklyn Bridge? How does he come to terms with the fact he will be wrong most of the time? 3.) What are Charlie's views towards follow-on funding and allocating reserves of the fund? How important is this from a return multiple perspective? How much of a difference does it make for founders to raise a next round with 100% of seed investors committed? 4.) Charlie has previously suggested the importance of being helpful and hard working. Is that really enough to build a brand in today's competitive VC environment? Is brand a form of defensible IP? 5.) How does Charlie react to Ben Lerer's suggestion that Jet.com and Dollar Shave Club are the first dominoes of an incoming wave of e-commerce M&A? Items Mentioned In Today's Show: Charlie's Fave Blog: Wait But Why Charlie's Most Recent Investment: Industrial Organic As always you can follow Harry, The Twenty Minute VC and Charlie on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner's sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com Cirrus Insight is a plugin for sales pros who use Gmail and Outlook. It automatically updates activities in Salesforce so you don't have to. It was named #41 on the Inc. 500 list of fastest-growing companies, and it has more than 1,700 customer reviews on the Salesforce AppExchange. Today, it serves over 150,000 sales people across 5,000 organizations using Gmail, Outlook, iPhone, iPad, and Android. Cirrus Insight is perfect for sales, support, and success teams who want to save time, schedule 3x more appointments, track email opens and much more with Salesforce information at their fingertips in the inbox. www.cirrusinsight.com/20VC

2 Jan 201728min