20VC: Sequoia's Leadership Transition | Michael Burry Shorts NVIDIA and Palantir | Gamma Raises $100M at $2BN | Has Defensibility Died in a World of AI | Datadog Surges as Duolingo Plummets: What is Happening

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

Nitesh Banta is the Founder and CEO @ B12, the startup that uses AI to superpower their team of world class creatives to create even more intelligent websites. They have backing from the likes of Jim Breyer, General Catalyst and our friends at Founder Collective. As for Nitesh, prior to B12, he was on the dark side as a VC with General Catalyst for 5 years before Co-Founding Rough Draft Ventures, the General Catalyst program designed to develop the next generation of student founders. In Today's Episode You Will Learn: 1.) How Nitesh made the move from VC with General Catalyst to AI Startup founder with B12? 2.) How difficult was it for Nitesh to leave the security of venture to start B12 as Founder? What does Nitesh suggest to those that are unsure of whether to make the jump? 3.) Why does Nitesh believe that AGI (artificial general intelligence) is not as close as people predict? What are the implications of this towards humans relationship with technology? 4.) Is Nitesh bullish on humans creating new and unique machine learning algorithms or the rise of 'machine learning as a service as a sector? Where does the real value lie, the data or the machine learning algorithms? 5.) Why is Nitesh contra the common pessimism surrounding AI and the future of work? How does Nitesh believe AI will impact human work processes in a positive way? Items Mentioned In Today's Show: Nitesh's Fave Blog: Bill Gurley: Above The Crowd, Nuzzel Nitesh's Fave Book: Oh The Places You'll Go As always you can follow Harry, The Twenty Minute VC and Nitesh on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. Pearl believes the latest automotive technology should be available to every driver – whether it's time for you to buy a new car or not. RearVision is our first step in driving this commitment forward. Pearl RearVision is the only wireless backup camera and alert system that installs in minutes and updates throughout its lifetime. Pearl literally takes less than 10minutes to install and is completely wireless because it's solar powered. Since RearVision is software based, we're able to push updates and new features over the Pearl App in the exact same way you receive updates for other apps on your phone. Pearl RearVision is perfect for anyone who wants to upgrade their car in minutes. Pearl RearVision is $499.99 and available at PearlAuto.com. It's also available on Amazon and through Crutchfield.

30 Dec 201628min

Kent Goldman is the Founder of Upside Partnership, one of the leading seed-stage investment firms in SF with investments in the likes of Laurel and Wolf, Digit and Lily. In 2015, he was named to the Midas Brink List. Prior to forming Upside Partnership in 2014, Kent was a Partner at seed investment pioneer First Round Capital. While there he led investments in companies including Airware, Hotel Tonight, and MemSQL. He also served on the board of Mashery (acquired by Intel). Earlier in his career, Kent was a member of Yahoo!'s corporate development team and also led business strategy for Yahoo! products generating $1 billion in annual revenue. In Today's Episode You Will Learn: 1.) How Kent made his way into the world of early stage investing and came to found Upside? 2.) What were the big takeaways from First Round for Kent? How has he applied those learnings to his formation of Upside? 3.) What does Kent look for in the LPs that invest in his fund? Why should founders look to learn which LPs are invested in the fund investing in them? 4.) How has Kent seen his investment decision-making process alter with time? What have been the big changes? 5.) Why does Kent believe valuation does not matter so much at the seed stage? What does really matter to him at the seed stage? How does this progress with rounds? Items Mentioned In Today's Show: Kent's Fave Blog: Howards Marks: Oaktree Capital Kent's Fave Book: A River Runs Through It And Other Stories Kent's Most Recent Investment: Live Neighborly As always you can follow Harry, The Twenty Minute VC and Kent on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. Pearl believes the latest automotive technology should be available to every driver – whether it's time for you to buy a new car or not. RearVision is our first step in driving this commitment forward. Pearl RearVision is the only wireless backup camera and alert system that installs in minutes and updates throughout its lifetime. Pearl literally takes less than 10minutes to install and is completely wireless because it's solar powered. Since RearVision is software based, we're able to push updates and new features over the Pearl App in the exact same way you receive updates for other apps on your phone. Pearl RearVision is perfect for anyone who wants to upgrade their car in minutes. Pearl RearVision is $499.99 and available at PearlAuto.com. It's also available on Amazon and through Crutchfield.

28 Dec 201623min

David Politis is the Founder & CEO @ Bettercloud, the first ever unified SaaS management platform. Bettercloud have raised over $40m in funding from some of today's best investors including past guests from Accel, Greycroft Partners and Flybridge Partners, just to name a few. Before founding BetterCloud, David was an early employee of Cloud Sherpas (acquired by Accenture [NYSE: ACN]) where David led Cloud Sherpas to become the leading Google Apps services provider and reseller to SMBs worldwide. Prior to Cloud Sherpas, David was the founding employee and General Manager of Vocalocity (acquired by Vonage [NYSE: VG]), which he grew into one of the top providers of cloud PBX technology. In Today's Episode You Will Learn: 1.) How Dave came to found Bettercloud? What was the a-ha moment for him? 2.) Why does David like to invest in everything but perks? What are the challenges of incentivising a team with Perks? What are the alternatives? 3.) What are the limits to transparency? Can there ever be too much transparency? How do you engender a culture of radical transparency within the workforce? 4.) How was the fundraising process for David? how did it alter and develop with every round? What did he do well and what would he improve upon? 5.) How can founders optimise the on boarding process for new hires? What is fundamental? What are the common mistakes and how can this be hacked for success? Items Mentioned In Today's Show: David's Fave Blog: Recode David's Fave Book: Banker To The Poor As always you can follow Harry, The Twenty Minute VC and David on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. Pearl believes the latest automotive technology should be available to every driver – whether it's time for you to buy a new car or not. RearVision is our first step in driving this commitment forward. Pearl RearVision is the only wireless backup camera and alert system that installs in minutes and updates throughout its lifetime. Pearl literally takes less than 10minutes to install and is completely wireless because it's solar powered. Since RearVision is software based, we're able to push updates and new features over the Pearl App in the exact same way you receive updates for other apps on your phone. Pearl RearVision is perfect for anyone who wants to upgrade their car in minutes. Pearl RearVision is $499.99 and available at PearlAuto.com. It's also available on Amazon and through Crutchfield. Xero is beautiful, easy-to- use online accounting software for small businesses. With Xero, you can easily manage your accounting anytime, anywhere from your computer or mobile device.When you add Xero to your small business you are able to: Send online invoices and get paid faster. Get an instant view of your cash flow. Track your payroll and keep tabs on your inventory. Partner with your accountant and bookkeeper in real time whenever you like. You can also customize your Xero experience with over five hundred business apps, including advanced solutions for point-of- sale, time tracking, ecommerce and more. Sign up for a free thirty-day trial at xero.com/20vc

23 Dec 201629min

Parker Thompson is a Partner @ AngelList and creator of popular parody Twitter Account, Startup L Jackson. At AngelList Parker has made investments in the likes of former guests, Algolia, Realty Shares and Keen IO. Prior to joining AngelList, Parker was a Partner at 500 Startups in SF and his illustrious path prior to investing includes Pivotal Labs, co-founding PlaceSite, preserving the interwebs at the Internet Archive, and working on digital copyright at UC Berkeley's iSchool. In Today's Episode You Will Learn: 1.) How Parker made his way into the world of early stage investing from the world of operations? 2.) How does Parker look to evaluate startup founders? What questions does he like to ask? What traits does he like to see in the core exec? 3.) Why does Parker think "not enough traction" is a BS VC excuse? How should VC's approach saying no to founders? What are the real reasons a VC is saying no in this case? 4.) Why does Parker believe the jump to Series A is bigger than ever? What has caused this? What metrics do startups have to achieve to make this move successfully? 5.) How should founders determine how much money to raise? If they can should they raise a 'warchest'? Why should founders not be concerned with dilution in the early days? Items Mentioned In Today's Show: Parker's Fave Blog: Stratechery, Nuzzel Parker's Fave Book: The Modernist Cuisine Parker's Most Recent Investment: Common Networks As always you can follow Harry, The Twenty Minute VC and Parker on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. Pearl believes the latest automotive technology should be available to every driver – whether it's time for you to buy a new car or not. RearVision is our first step in driving this commitment forward. Pearl RearVision is the only wireless backup camera and alert system that installs in minutes and updates throughout its lifetime. Pearl literally takes less than 10minutes to install and is completely wireless because it's solar powered. Since RearVision is software based, we're able to push updates and new features over the Pearl App in the exact same way you receive updates for other apps on your phone. Pearl RearVision is perfect for anyone who wants to upgrade their car in minutes. Pearl RearVision is $499.99 and available at PearlAuto.com. It's also available on Amazon and through Crutchfield. Xero is beautiful, easy-to- use online accounting software for small businesses. With Xero, you can easily manage your accounting anytime, anywhere from your computer or mobile device.When you add Xero to your small business you are able to: Send online invoices and get paid faster. Get an instant view of your cash flow. Track your payroll and keep tabs on your inventory. Partner with your accountant and bookkeeper in real time whenever you like. You can also customize your Xero experience with over five hundred business apps, including advanced solutions for point-of- sale, time tracking, ecommerce and more. Sign up for a free thirty-day trial at xero.com/20vc

21 Dec 201632min