20VC: Uber's Journey to Becoming the Most Valuable Private Tech Company in History, Raising $3BN From Saudi in Just 60 Days, Uber's $30BN Mistake in Food Delivery, Why Recent Uber M&A Will be the Worst in Tech & Mastering Negotiations and Deal-Making with

Josh Udashkin is the Founder and CEO @ Raden, essentially making the unsexy sexy with a design-forward app-connected piece of luggage that provides a superior end-to-end travel experience. Prior to founding Raden, Udashkin practiced law and did international development for Canadian shoe company, Aldo. To date, Raden have raised funds from our friends @ First Round Capital, Lerer Hippeau, Pritzker Group and many more incredible investors. In Today's Episode You Will Learn: 1.) How Josh came to found Raden and what the a-ha moment was for him? 2.) Why does Josh believe in the benefits of the dual approach to selling both being online and with physical retail stores? 3.) Why have we seen such innovation in the space in the last 30 years? The incumbents have said, they are bad at selling online, what are they doing wrong? What is Josh doing to optimise the process? 4.) Why is Josh bullish on omni-channel retail? What are the benefits? 5.) How are hardware products innovating on the hardware as a service model and integrating physical retail products with superior mobile experiences? 6.) What trends have we seen in investing in hardware products in the last 5 years or so? Why is hardware becoming more attractive an investment field? Items Mentioned In Today's Episode: Josh's Fave Book: Shoe Dog: A Memoir by the Creator of NIKE Josh's Fave Blog: Business of Fashion As always you can follow The Twenty Minute VC and Harry on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here! If you are looking to make your move into the world of VC or improve your investing skills, Venture Capital Unlocked: Secrets of Silicon Valley Investing is a must! It is a 2 week crash course at Stanford run by Stanford Professional Development Centre and 500 Startups. You will learn the mechanics of all things Silicon Valley investing, check it out here. The Twenty Minute VC is brought to you by Leesa. Lees is like the TOMS Shoes or Warby Parker of the mattress industry. Here are 3 reasons why they are the best place to get your new mattress: Leesa has done away with the awkward mattress showroom experience by allowing a fully online experience, shipping to your doorstep for free. Their 10 inch mattresses come in all sizes and is crafted with 3 unique layers o foam including2 inches of memory foam and 2 inches of really cool latex like foam design to keep you cool. All Leesa mattresses are made 100% in the US or UK and they give you a 100 night trial, to make sure the mattress is perfect for you. Go to leesa.com/VC and enter promo code VC75 to get $75 off!

1 Jul 201628min

Wesley Chan is a Manging Director @ Felicis Ventures where he has led investments in the likes of Canva, Flexport and Luma, just to name a few. Prior to Felicis, Wesley was a General Partner @ Google Ventures. Before Google Ventures he was an early employee at Google, where he founded and launched Google Analytics and Google Voice, resulting in his being awarded Google's Founders Award–the company's most prestigious recognition–for leading the development of Google's early client efforts, which led to the development of Google Chrome. Fun fact about Wesley he is a massive hacker and IOT enthusiast with over 100 connected devices in his home. In Today's Episode You Will Learn: 1.) How Wesley made the transition from Foundering Google Voice and analytics to being a VC? 2.) What were Wesley's biggest takeaways from leading investment at Google Ventures? When looking at his investment in Nest, what makes Nest such a truly phenomenal connected device? 3.) Wesley previously said, 'I look for patterns similar to Google Analytics in how if you build something great.' What are those patterns and what does that thought process lead to in terms of thought outcome? What is a good example of this? 4.) Where does Wesley think we are on the programmable interface element of consumer hardware? What would he like to see change or improve in the space? 5.) How has Wesley seen the investor sentiment to hardware change over the last decade? What have been the rivers in the rising positivity of investing in hardware? Items Mentioned In Today's Show: Wesley's Fave Book: The Big Short Wesley's Most Recent Investment: Luma As always you can follow The Twenty Minute VC, Harry and Wesley on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Snapchat here! If you are looking to make your move into the world of VC or improve your investing skills, Venture Capital Unlocked: Secrets of Silicon Valley Investing is a must! It is a 2 week crash course at Stanford run by Stanford Professional Development Centre and 500 Startups. You will learn the mechanics of all things Silicon Valley investing, check it out here. The Twenty Minute VC is brought to you by Leesa. Leesa is like the TOMS Shoes or Warby Parker of the mattress industry. Here are 3 reasons why they are the best place to get your new mattress: Leesa has done away with the awkward mattress showroom experience by allowing a fully online experience, shipping to your doorstep for free. Their 10 inch mattresses come in all sizes and is crafted with 3 unique layers o foam including2 inches of memory foam and 2 inches of really cool latex like foam design to keep you cool. All Leesa mattresses are made 100% in the US or UK and they give you a 100 night trial, to make sure the mattress is perfect for you. Go to leesa.com/VC and enter promo code VC75 to get $75 off!

29 Jun 201631min

David Cohen is the founder and managing partner at Techstars, so a few amazing stats on techstars first, they have a total of 762 companies of which 90% are active or have been acquired, having raised more than 2bn in funding, as for David he is a serial entrepreneur having founded Pinpoint Technologies which was acquired by ZOLL Medical Corporation in 1999. and David was also the founder and CEO of earFeeder.com, a music service which was sold to SonicSwap.com in 2006. In Today's Episode You Will Learn: 1.) How David made the transition from Founder to VC with Techstars and Fund I? 2.) Fund I is one of the most successful funds in history; what was the structure with Fund I? Why did David choose a $5m fund size? How did he decide initial to follow on ratio? 3.) Why was David so valuation sensitive with Fund I? Why was David so rigid on a consistent cheque size on Fund I? 4.) Why did David decide to expand from being a solo GP fund? What are the challenges and complexities of fund scaling and did David approach this? 5.) Question from Ari Newman: What does David think about uncapped notes? Why does David like big boring companies? Brett Jackson: How did you meet Ryan Graves @ Uber and how did the Uber deal come about? Jason Seats: Where does David still see inefficiencies in the current venture model? Items Mentioned In Today's Show: David's Fave Book: The Soul Of Money David's Fave Blog: Mattermark Daily As always you can follow The Twenty Minute VC, Harry and David on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Snapchat here! If you are looking to make your move into the world of VC or improve your investing skills, Venture Capital Unlocked: Secrets of Silicon Valley Investing is a must! It is a 2 week crash course at Stanford run by Stanford Professional Development Centre and 500 Startups. You will learn the mechanics of all things Silicon Valley investing, check it out here. The Twenty Minute VC is brought to you by Leesa. Leesa is like the TOMS Shoes or Warby Parker of the mattress industry. Here are 3 reasons why they are the best place to get your new mattress: Leesa has done away with the awkward mattress showroom experience by allowing a fully online experience, shipping to your doorstep for free. Their 10 inch mattresses come in all sizes and is crafted with 3 unique layers o foam including2 inches of memory foam and 2 inches of really cool latex like foam design to keep you cool. All Leesa mattresses are made 100% in the US or UK and they give you a 100 night trial, to make sure the mattress is perfect for you. Go to leesa.com/VC and enter promo code VC75 to get $75 off!

27 Jun 201626min

Dennis Mortensen is the CEO and Founder of X.ai, the artificial intelligence driven personal assistant that lets people schedule meetings using plain English and nothing more than a CC to amy@x.ai. Their female persona Amy is so lifelike that users have asked her on a date at a rate of one request per month! X.ai is now one of the best funded AI startups having raised over $30m from our friends at FirstMark and a big thanks to Matt Turck for making the intro and from DCM, who also helped us with some of the questions for Dennis! In Today's Episode You Will Learn: 1.) How Dennis came to found X.ai and what the a-ha moment was for him? 2.) What did the training look like for X.ai? How long did it take? How much data did you have to painstakingly annotate? What is more important; data or algorithms? 3.) Many VCs are concerned about large incumbents having proprietary data sets. Does this concern Dennis and what can be done to mitigate this 4.) Question from David Cheg @ DCM: How will AI startups interact with giant corporates also investing heavily in AI research? 5.) How was the fundraising journey for Dennis? How did he approach it strategically? What challenges did he face? How did he go about choosing his investors? Items Mentioned In Today's Episode: Dennis' Fave Book: How To Get Rich by Felix Dennis Dennis' Fave Blog: Wait But Why As always you can follow The Twenty Minute VC, Harry and Dennis on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here! If you are looking to make your move into the world of VC or improve your investing skills, Venture Capital Unlocked: Secrets of Silicon Valley Investing is a must! It is a 2 week crash course at Stanford run by Stanford Professional Development Centre and 500 Startups. You will learn the mechanics of all things Silicon Valley investing, check it out here. The Twenty Minute VC is brought to you by Leesa. Lees is like the TOMS Shoes or Warby Parker of the mattress industry. Here are 3 reasons why they are the best place to get your new mattress: Leesa has done away with the awkward mattress showroom experience by allowing a fully online experience, shipping to your doorstep for free. Their 10 inch mattresses come in all sizes and is crafted with 3 unique layers o foam including2 inches of memory foam and 2 inches of really cool latex like foam design to keep you cool. All Leesa mattresses are made 100% in the US or UK and they give you a 100 night trial, to make sure the mattress is perfect for you. Go to leesa.com/VC and enter promo code VC75 to get $75 off!

24 Jun 201630min

Annie Kadavy is a General Partner @ Charles River Ventures. The prestigious VC fund that is now on it's 16th fund and has backed the likes of Twitter, Yammer and Mailbox just to name a few. At CRV, Annie focuses on all things consumer and has either led or sourced their investments in ClassPass, Cratejoy, Patreon, Laurel & Wolf and DoorDash. Prior to CRV, Annie spent time with SV Angel and Warby Parker. In Today's Episode You Will Learn: 1.) How Annie made her way into the world of VC? 2.)Why have we seen the explosion of marketplaces in recent years? What are the inherent challenges of two sided marketplaces; typically consumers and micro-entrepreneurs? Does Annie agree with Jeff Jordan in stating that these marketplaces need to nurture and manage conditions of perfect competition? 3.) What are the core components to growing traditional producer consumer marketplaces? How do they broach the chicken and the egg problem of supply and demand? 4.) Why is Annie so excited for the potential of bots? 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: Annie's Fave Book: Mindset: How You Can Fulfill Your Potential by Carol Dweck Annie's Fave Blog: The Skimm Annie's Most Recent Investment: Roam

22 Jun 201631min

From 1995 until 2004 Andy Rachleff was a co-founder and General Partner of Benchmark Capital, who have backed the likes of Twitter, Snapchat, Dropbox, Uber and Instagram. Upon his retirement from Benchmark, Andy joined the faculty of the Stanford Graduate School of Business to teach a variety of courses on entrepreneurship. In 2008 he co-founded Wealthfront Inc, the online financial advisor and investment management solution, where he now serves as Executive Chairman. In just 3 years, Wealthfront now have over $2bn AUM. In Today's Episode You Will Learn: 1.) How Andy made his way into the world of VC and what was the origin story behind the founding of Benchmark? 2.) Andy took the opposite route to most having been a VC and then founding Wealthfront. So what does Andy make of doing VC first and then becoming an operator? 3.) Why does Andy believe Ivy League endowments are the best managed pools of capital? What do they do well and what separates the good from the great? 4.) Andy has worked with some of the world's best CEO's and board members, so what makes the best board member and what makes the best CEO? 5.) How has Andy seen the VC industry evolve and develop over the last 20 years? How has Andy seen his own investment decision making process and patter recognition alter over that time? Items Mentioned In Today's Episode: Andy's Fave Book: The Innovator's Dilemma As always you can follow The Twenty Minute VC, Harry and Andy on Twitter here! The Twenty Minute VC is brought to you by Leesa, the Warby Parker or TOMS shoes of the mattress industry. Lees have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is order completely online and ships for free to your doorstep. The 10 inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com/VC and enter the promo code VC75 to get $75 off!

20 Jun 201626min

Sasha Orloff is the CEO and Co-founder of LendUp, a fintech startup offering online and mobile personal loans and credit cards in the United States. Prior to launching LendUp Sasha was on the other side of the table as a VC with Citi Group's corporate venture capital arm. On the topic of VC funding, LendUp raised an incredible $150m in Jan 2016 from likes of SV Angel, Yuri Milner our friends at Susa and Google Ventures just to name a few. In Today's Episode You Will Learn: 1.) How did Sasha come to found LendUp following a stint in VC with Citi Group? 2.) What Sasha learnt from VC about running a successful startup and how he applied them to his founding of LendUp? 3.) Was it difficult leaving the security of a VC job to found a startup? Would you have done the same had you had children at the time? 4.) What trends in FinTech is Sasha most excited for? Why does Sasha think banks are in so much trouble? Is there the potential to co-operate rather than replace banks? 5.) How was the fundraising process for Sasha? What was his preferred round and how did they differ from stag to stage? Items Mentioned In Today's Episode: Sasha's Fave Book: Banker To The Poor Sasha's Fave Blog: Sam Altman As always you can follow The Twenty Minute VC, Harry and Sasha on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here! The Twenty Minute VC is brought to you by Leesa, the Warby Parker or TOMS shoes of the mattress industry. Lees have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is order completely online and ships for free to your doorstep. The 10 inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com/VC and enter the promo code VC75 to get $75 off!

17 Jun 201624min

Chris Douvos is Managing Director @ Venture Investment Associates (VIA) where he is a member of the Firm's Investment Committee and has responsibility for the management of relationships with the funds' managers and its limited partners, as well as the identification and development of new relationships for the Firm. Prior to joining VIA, he spent time at The Investment Fund For Foundations (TIFF). where he was responsible for over $1 billion. Prior to that, Chris worked on Princeton University's endowment team. One of Chris' most notable investments is his pre-first fund investment in First Round Capital. Chris is also the author of the fantastic blog, www.SuperLP.com, definitely check that out if you have not had the chance yet. In Today's Episode You Will Learn: 1.) How did Chris make his way into the world of limited partners? 2.) How does Chris respond to FOMO as an LP? Does it affect his decision making process? How does he look to avoid it? 3.) What patterns and processes has Chris developed to asses the ability of potential GPs? 4.) Is Chris concerned by the increasing time it is taking for startups to exit? How does this affect his think as an LP and cash on cash relationship to this asset class? 5.) In 2013, Chris aid micro VC was the most exciting space in VC, where is he most excited for now? Where will we see innovation in the VC market? Items Mentioned In Today's Episode: Chris' Fave Blog: RedEye VC, Tomasz Tunguz Chris' Fave Book: The Great Gatsby Chris' Most Recent Investment: Other Lab As always you can follow The Twenty Minute VC, Harry and Chris on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here! The Twenty Minute VC is brought to you by Leesa, the Warby Parker or TOMS shoes of the mattress industry. Lees have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is order completely online and ships for free to your doorstep. The 10 inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com/VC and enter the promo code VC75 to get $75 off!

15 Jun 201629min