Catch Jason Calacanis at TIA Tokyo 2018 as he shares how he turned $100K to $100M

Jason Calacanis is perhaps most well-known for being one of the earliest investors in Uber. In 2009, the ride-hailing company was valued at US$4 million and was raising its first funding round. Fast forward to today, Uber is valued at US$72 billion – making it worth 18,000 times more compared to when Jason first bet on the business.

Today, Jason’s estimated net worth stands at US$20 million. Back in 2003, he co-founded Weblogs Inc, which was bought by AOL for US$30 million after 18 months of operation – netting him US$10 million.

In addition to having founded Silicon Alley Reporter, Weblogs Inc, Mahalo, and Inside.com, Jason is also the creator of startups festival LAUNCH, as well as the podcast This Week in Startups.

Learning from missed opportunities

Jason didn’t immediately get attracted into the world of angel investing. He missed several investment opportunities – Twitter (a US$50 million mistake) and Zynga. He also passed on investing in Tesla despite being good friends with Elon Musk. After realizing the golden opportunities missed, he was determined to start investing in the ideas of people around him.

This was how he became one of the first investors in Uber. Before even hearing about ex-CEO Travis Kalanick’s idea, Jason decided that he wanted in.

Till date, Jason has invested in 150 companies, out of which six are unicorns – including Uber, Thumbtack and Robinhood.

Investing in billion-dollar founders

When asked what qualities to look out for when investing, Jason shared that it’s crucial to invest in resilient founders. He believes that startups fail because the founder quit; not because the founder ran out of money.

Instead of being intrigued by the business idea, Jason invests in entrepreneurs who are passionate, capable and persistent. He shared in an interview with Recode Media: “You’re investing in the person and the more outlandish the idea is, and the less people understand it, the greater the chances you should invest in it are”.

Looking to attract angel investors?

For startups looking for angel investors, Jason has several tips – be product ready, and your business should ideally have five to 10 customers. At the idea stage where the business is undergoing a pre-product or pre-market fit, Jason advises that it is likely too early to look for angel investors.

To address the problem of investors keeping their options open without committing to startups, Jason encourages founders to have a “forcing function”. This means to email investors they’ve met and ask if they’re interested in investing with three options – yes, no, or not yet. By doing so, entrepreneurs will be able to efficiently move on.

Jason Calacanis on what he learned from picking six unicorns as an angel investor

Whether you’re looking to attract angel investors for your startup or looking to learn lessons from investing, be sure to catch the session “Fireside Chat with Angel Investor Extraordinare, Jason Calacanis” happening at Tech in Asia Tokyo 2018 on 20 September.

In addition to soaking in insights from industry experts, you’ll be able to check out 120 handpicked exhibitors at Startup Factory, where entrepreneurs will be showcasing their innovative products and services. You’ll also get to network with 2,000 investors, media, and inspiring tech enthusiasts.

Here’s the part you’ve been waiting for. From now till this Sunday, 5 August, tickets are going at a 15 percent discount (code: tiatokyo15). Prices will increase after this week, so don’t sit on it for too long!