Prompt Cast
Jason Calacanis: From Selling VHS Tapes to Becoming a Tech Industry Influencer
TLDR Jason Calacanis, one of the top angel investors of all time, shares his journey from selling VHS tapes to founding multiple companies, making over 200 angel investments, and becoming an influential figure in the tech industry. He discusses his early experiences, his desire for fame and success, his rivalry with Nick Denton, his investments in companies like Uber and Stripe, and his advice for angel investors.
Timestamped Summary
00:00
Jason Calacanis has founded multiple companies, podcasts, and conferences, made over 200 angel investments, and is considered one of the top angel investors of all time.
06:24
Jason Calacanis grew up in Brooklyn in the 70s and 80s, where he worked at his dad's bar and got exposed to commerce at a young age, even starting his own business selling copies of the Empire Strikes Back on VHS tapes.
12:47
Jason Calacanis talks about his early experiences with group viewing and playing poker with Silicon Valley folks, which eventually led to hosting a famous poker game at the D conference and starting a weekly poker game in Silicon Valley.
18:36
Jason Calacanis talks about his early experiences with scams, selling video games, and starting his own magazines, including Cyber Surfer and Silicon Island Reporter, which eventually caught the attention of Rolling Stone creator John Winter.
24:11
Jason Calacanis reflects on his desire for fame, power, and money, and his goal of becoming a media mogul, as well as the collapse of his magazine and his determination to come back stronger.
29:57
Jason Calacanis tries to recruit talented writers from Gawker, such as Elizabeth Spears and Peter Rojas, by offering them equity in his company and the promise of becoming millionaires, as he believes that blogs will surpass magazines in the future.
35:31
Jason Calacanis and Nick Denton had a rivalry in the early days of blogging, but eventually reached a truce and agreed to not poach each other's writers.
41:26
Jason Calacanis invested in Uber because he had a previous relationship with Travis Kalanick and believed in the company's potential.
47:37
Jason Calacanis became an influential figure in the tech industry after his success with Mahalo, which was backed by Sequoia Capital and led to him being anointed by both the East and West Coast venture capitalists.
53:16
Jason Calacanis discusses the founding of his company Mahalo, how he pitched the idea to investors, and the eventual downfall of the company due to Google's actions.
59:05
Jason Calacanis discusses his investments in various companies, including Uber, Stripe, Thumbtack, and Datastacks, and his initial skepticism towards online investing before being introduced to Angel List by Naval Ravikant.
01:04:23
Jason Calacanis discusses his decision to start a podcast and his role in connecting influential people in the tech industry.
01:11:05
Jason Calacanis started his podcast as a fun way to promote his friends, but it quickly grew in popularity and he was able to sell advertising slots, making a couple million dollars and supporting a team of seven or eight people.
01:16:31
Jason Calacanis advises angel investors to make a large number of smaller bets in startups that have already launched their product and have some customers, in order to increase their chances of success.
01:22:43
Investing in companies with some amount of revenue, even as little as two to 10,000 a month, can eliminate a significant amount of risk for angel investors.
01:28:57
Jason Calacanis discusses his investment strategy, which involves making multiple bets on companies and aiming to reach a 10-20% ownership stake.
Categories:
Technology
Business
