Jason Calacanis: The World's Greatest Angel Investor

Jason Calacanis: The World's Greatest Angel Investor

Jason Calacanis is arguably the world's greatest angel investor with over 60 investments including the likes of Uber (1st round), ThumbTack and Calm, just to name a few. Jason is also the Host of This Week In Startups, the world's biggest startup podcast and Founder of Launch and Launch Festival, the world's biggest startup festival.

In this interview we discuss, how Jason invested in Uber's 1st round, what Jason looks for in startups, how Jason can tell whether a founder has got what it takes, which VC's Jason most likes to work with, which entrepreneurs Jason most likes to invest in, what pisses Jason off more than anything, what inspires him more than anything, what industries will see the most disruption in the coming years, what makes a great entrepreneur and how startups can position themselves best for entering a round of funding.

Enjoy! All show notes, links and resources from this episode can be found at http://www.thetwentyminutevc.com and you can follow Harry, Jason and The Twenty Minute VC on Twitter.

Mentioned in Today's Show:

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20 VC 071: Pre-Seed Investing, Why Now Is The Best Time with Nicholas Chirls @ Notation Capital

20 VC 071: Pre-Seed Investing, Why Now Is The Best Time with Nicholas Chirls @ Notation Capital

Nicholas Chirls is the Founder and Partner @ Notation Capital, one of New York's genuine pre-seed funds investing in pre-growth startups with huge potential. Prior to Notation, Nichoas was Head of Investment at Betaworks, leading investments in companies such as Electric Objects, Estimote, URX, Namo Media (acquired by Twitter) and Grand St. (acquired by Etsy). If you would like to email Nick, his email is nick@notationcapital.com In Today's Episode You Will Learn: 1.) How Nick made his move into the venture industry? 2.) Who does Nick consider a mentor and thought leader in the VC industry? 3.) Why now is the best time to be a pre-seed fund in NYC? 4.) At the pre-seed stage what metrics does Notation focus on? 5.) How does Nicholas evaluate the valuation ecosystem? 6.) How does Nicholas handle deal sourcing? Where does he find startups to invest in? 7.) Does crowdfunding act as a competing finance method at the pre-seed stage? Items Mentioned In Today's Episode: Nick's Fave Book: My Brilliant Friend by Elena Ferrante Nick's Fave Newsletter: Wait But Why Nick Most Recent Investment: Zipdrug: Your Prescriptions Delivered on Demand Best Meditation Apps: Headspace, Calm As always you can follow Harry, The Twenty Minute VC, Nick and Notation on Twitter here! If you would like to see a more colourful side to Harry with many mojito sessions, you can follow him on Instagram here!

14 Sep 201529min

20 VC 070: Do Investors in California Outperform The Rest of The World with Eric ver Ploeg @ Recursive Capital

20 VC 070: Do Investors in California Outperform The Rest of The World with Eric ver Ploeg @ Recursive Capital

Eric ver Ploeg has sat on both sides of the table as an entrepreneur and a VC. Eric started his career as an entrepreneur with the founding of Adknowledge, the 1st internet ad serving company, which was sold for $193m. He then went on to Angara, a Kleiner Perkins backed startup which led to his move into venture with VantagePoint, where he led VantagePoint's investment activities in the mobile arena, leading over $160m in investments. Eric is also a fantastic writer and his articles can be found on Medium here! In Today's Episode You Will Learn: 1.) How Eric made the move from Angara, Kleiner Perkins company, to his role in venture? 2.) How being a founder affected how Eric interacted and invested in startups? 3.) How can founders learn the skills of interacting with their investors and board? 4.) What makes the hot companies, hot and the others struggle? 5.) Does Eric agree with startups raising a 'warchest' of funds if they can? How can startups determine what is the right amount to raise? 6.) Why are SF angels so much more successful than other investors? What do they have that other do not? Items Mentioned In Today's Show: Eric's Fave Book: The Lean Startup by Eric Ries, Crossing The Chasm by Geoffrey Moore Eric's Fave Newsletter or Blog: Tomasz Tunguz Research and analysis provided by CB Insights As always you can follow Harry, The Twenty Minute VC and Eric on Twitter here? To see a more colourful side to Harry's personality and a few mojito sessions, you can follow Harry on Instagram here!

9 Sep 201529min

20 VC 069: Jeff Clavier, King of Seed Funding @ SoftTech VC on Brad Feld, Fitbit and Standout Startups

20 VC 069: Jeff Clavier, King of Seed Funding @ SoftTech VC on Brad Feld, Fitbit and Standout Startups

Jeff Clavier is the Founder and Managing Partner of SoftTech VC, one of the most established seed VC firms in Silicon Valley, having closed 150 investments since 2004. An early angel investor in Web 2.0, Jeff and his team have backed successful startups like Mint (Intuit), Milo (eBay), Bleacher Report (Turner), Fitbit, Eventbrite, Sendgrid, Postmates and Vungle. The portfolio has also seen acquisitions by Groupon, Twitter, Facebook, Yahoo and AOL. The firm is currently investing out of its $85M Fund IV, making 16 commitments of $850K per year in mobile/cloud saas, consumer hardware, marketplaces and healthcare IT. In Today's Episode You Will Learn: 1.) How Jeff made his entry into the world of VC? 2.) In a time when hardware was not heavily invested in, what attracted Jeff to Fitbit? 3.) How did Jeff convince Brad to invest in Fitbit? 4.) What can startups do to standout in the crowded market that exists today? 5.) What do startups need to have to get a meeting with you at SoftTech? 6.) What VCs does Jeff most like to invest alongside? Items Mentioned In Today's Episode: Jeff's Fave Book: June by Gerbrand Bakker As always you can follow Harry, The Twenty Minute VC, Jeff and SoftTech VC on Twitter here! For a more colourful look into Harry's life, you can follow him on Instagram here!

7 Sep 201526min

FF 012: Acquired by Microsoft for $200m with Javier Soltero @ Microsoft

FF 012: Acquired by Microsoft for $200m with Javier Soltero @ Microsoft

Javier Soltero is Corporate Vice President of Outlook @ Microsoft. This position arose due to Javier's startup, Acompli, being acquired by Microsoft for $200m in 2014. Prior to Acompli, Javier spent a year at Redpoint Ventures, where he assisted in helping the firm extend their reach into both enterprise and mobile markets. However, Javier's entrepreneurial career did not start with Acompli, as he co-founded Hyperic, which he bought for $1 and within 5 years turned into a $10m+ revenue generating company. In Today's Episode You Will Learn: 1.) How did Javier start his entrepreneurial career and what were the origins of Acompli? 2.) What was Javier's biggest takeaway from the failure of his first startup, back by Sequoia? 3.) How did Javier control his burn rate once large amounts of VC money was in his company? 4.) How does Javier approach product market fit? 5.) How did Javier meet his investors for Accompli and how did Javier find the fundraising process? 6.) What were Javier's reasons for selling Acompli? Was there any conflict with his investors in selling the company? Items Mentioned In Today's Episode: Javier's Fave Book: 100 Years of Solitude by Gabriel Garcia Marquez Javier's Fave Newsletter or Blog: Wait but Why? As always you can follow Harry, The Twenty Minute VC and Javier right here on Twitter! If you would like to see a more colourful side to Harry with many a mojito session, you can follow Harry on Instagram here!

6 Sep 201529min

FF 011: 'The Savviest Investors Don't Ask What If' with Ben Nader, CEO & Founder @ Butterfleye

FF 011: 'The Savviest Investors Don't Ask What If' with Ben Nader, CEO & Founder @ Butterfleye

Ben Nader is Founder and CEO at Butterfleye, the most advanced wireless home monitoring system. In other words, Google Nest meets Dropcam. Butterfleye's investors include some of the biggest and most prominent names in the industry including our friends and past guests Brad Feld and Jason Calacanis. Butterfleye currently have a campaign on Indiegogo, which you can support here!   In Today's Episode You Will Learn: 1.) How did Ben come up with Butterfleye? 2.) How does Butterfleye differentiate itself from other competitors like Dropcam? 3.) How much better does a new product have to be to beat the existing incumbents? 4.) Does Ben prefer mass market testing or small targeted testing with fewer individuals? 5.) How did Ben get his first customers? 6.) What has Ben done to drive the success of his Indiegogo campaign? What tips would he give to founders looking to raise on these platforms? 7.) How did Ben get Jason Calacanis as an angel? How did Ben find the fundraising process?                  Items Mentioned In Today's Show: Ben's Fave Book: The Alchemist by Paolo Coelho Ben's Fave Newsletter or Blog: Brad Feld's Feld.com, Jason Calacanis' Launch Ticker Ben's Fave Productivity Apps: Asana, Sunrise Calendar, Calm Meditation App As always you can follow Harry, The Twenty Minute VC, Ben and Butterfleye on Twitter here! If you would like to see a more colourful side to Harry with some mojito sessions to come, you can follow him on Instagram here!

4 Sep 201526min

20 VC 068: Why Now Is The Best Time To Be An Entrepreneur with Sean Seton-Rogers @ PROfounders Capital

20 VC 068: Why Now Is The Best Time To Be An Entrepreneur with Sean Seton-Rogers @ PROfounders Capital

Sean Seton-Rogers is a founding Partner at PROfounders Capital, a venture capital fund for entrepreneurs powered by entrepreneurs. Their investors and principals number some of the best-known players within the digital media space -- people who have built some of Europe's most successful companies. Prior to PROfounders, Sean has been investing in technology companies across both the US and Europe, when he was at both Balderton Capital and Commonwealth Capital Ventures in Boston. In addition to the PROfounders portfolio companies, he has in the past worked closely with others such as Bebo, Wonga.com, and ConstantContact. In Today's Episode You Will Learn: 1.) How did Sean make his entry into the VC world at the peak of the first tech bubble? 2.) What was the biggest lesson Sean learnt from experiencing the bubble imploding? 3.) Why are we seeing this trend of US VC funds investing in Europe? 4.) What are the key drivers to the growth of the European tech ecosystem? 5.) Why is there a serious decline in the amount of Series C rounds, only 7 in Q2 2015? 6.) Is Sean concerned by the rise of Crowdfunding? Does Sean see it as a competing finance model to VC? 7.) Do investors on Crowdfunding platforms experience the same deal terms as VCs? Items Mentioned In Today's Episode: Sean's Fave Book: Robert Cialdini: Influence, The Psychology of Persuasion, Neal Stevenson: Cryptonomicon Sean's Fave Blog or Newsletter: Benedict Evans Newsletter Sean's Must Have Productivity Tools: Evernote, Google Apps Sean's Most Recent Investment: Made.com As always you can follow Harry, The Twenty Minute VC, Sean and PROfounders on Twitter right here! For a more colourful view of Harry and maybe a few mojito sessions follow Harry on Instagram here!

2 Sep 201529min

20 VC 067: Scaling Startups Into Unicorns with Atomico's Mattias Ljungman and Carolina Brochado

20 VC 067: Scaling Startups Into Unicorns with Atomico's Mattias Ljungman and Carolina Brochado

Mattias launched Atomico in 2006 alongside Niklas Zennström. In that time, Mattias has been involved with exits including Supercell (sold a majority stake to SoftBank), 6Wunderkinder (acquired by Microsoft in 2015), The Climate Corporation (acquired by Monsanto for $1.1B in 2013), Xobni (acquired by Yahoo! in 2013). Mattias works closely with a number of portfolio companies on their expansion, including Truecaller, Klarna, Hailo, and ChemistDirect. Carolina is Vice President @ Atomico, working on sourcing, evaluation and due diligence of investments. Carolina is based in London, however she travels frequently to Latin America to evaluate opportunities for Atomico to help companies in the region to scale. Prior to Atomico, Carolina started her career at Merrill Lynch's investment banking division before moving to private equity firm Madison Dearborn Partners. Did you like the double guest show today? If so click here! If you prefer a single guest click here! In Today's Episode You Will Learn: 1.) How Mattias and Carolina made their way into the VC industry with Atomico? 2.) How important is it for VCs to have entrepreneurial backgrounds? 3.) What advice would Mattias and Carolina give to anyone looking to enter the VC industry? 4.) What is Atomico's selection criteria? Average cheque size? Round preference? Sector preference? 5.) Why is now the best time to be a European entrepreneur? What has changed? 6.) What does it take for a tech ecosystem to thrive and grow? 7.) What is required for startups to scale from small markets to mass market adoption? Items Mentioned In Today's Show: Mattias' Fave Book: The Girl Who Saved The King of Sweden by Jonas Jonasson Carolina's Fave Book: Midnight in the Garden of Good and Evil by John Berendt Mattias' Fave Blog or Newsletter: Benedict Evans Carolina's Fave Newsletter: The Skim, Dan Primack: TermSheet Atomics's Most Used Productivity Tools: Wunderlist, Evernote, Pocket, SmartNews Atomics's Most Recent Investments: TrueCaller, GymPass As always you can follow Harry, The Twenty Minute VC, Carolina and Mattias on Twitter here! For a more colourful image of Harry and maybe some mojito sessions, follow Harry on Instagram here!

31 Aug 201528min

FF 010: Becoming Europe's Hottest Startup with Carl Waldekranz, Co-Founder and CEO @ Tictail

FF 010: Becoming Europe's Hottest Startup with Carl Waldekranz, Co-Founder and CEO @ Tictail

Carl Waldekranz is the CEO and co-founder of Tictail. With the vision of creating the worlds most used and loved e-commerce platform Tictail has been called the Tumblr of e-commerce and been celebrated as one of Europe's hottest startups. The vibrant community now hosts more than 85,000 stores on their service. Due to this phenomenal growth Tictail recently closed a $22m Series B from Balderton, Acton, Thrive and Creandum. In Today's Episode You Will Learn: 1.) What were Carl's entrepreneurial origins and how did Tictail get started? 2.) What does Carl's idea creation process look like? How does Carl brainstorm? 3.) Tictail now sells 2m products on their platform but how did they get their first customers? 4.) At what moment in the Tictail journey was Carl the most worried or frightened? 5.) What would Carl say are the essentials for funding? How did Carl meet his investors? What is the difference between the different funding rounds for startups? 6.) Why did Carl pitch other startups before pitching VCs? 7.) Question from Daniel Waterhouse @ Balderton: How has Tictail maintained the magic company culture in Sweden, whilst expanding to NY? 8.) If Carl could start his time with Tictail again, is there anything he would have done differently? Items Mentioned In Today's Show: Carl's Fave Book: The Score Takes Care of Itself, My Philosophy of Leadership by Bill Walsh Carl's Fave Blog or Newsletter: First Round Capital Blog As always you can follow Harry, The Twenty Minute VC, Carl and Tictail on Twitter right here! If you would like to see a more colourful side to Harry and a few mojito sessions, you can follow Harry on Instagram here!

28 Aug 201526min

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