A2D Ventures is Southeast Asia’s prominent early-stage venture capital firm, syndicate, and investing platform. The firm invests in innovative and impactful companies across various sectors, with a focus on supporting entrepreneurs who are building the future of Southeast Asia.
Guest Author: Ankit Upadhyay
I’m a fan of Jason Calacanis. In part because our model for A2D Ventures is built based on learnings from him, but also just because I think he reflects the right values and has a great story.
His story is one of scrappiness. A scrappy kid from Brooklyn who ‘made it’ in Silicon Valley.
Today Jason is one of the most sought after seed funding checks in Silicon Valley. Why?
Well… in part because he is very well connected. For example he is one of the four members of “The All-In Podcast”, which is also informally known as the ‘billionaire’s podcast’ because many of the members are billionaires.
But also because has built a one-man brand that represents a mix of astute coach, talent agent, promoter, and gatekeeper to success in the game.
Not to mention the fact that he hosts five podcasts a week, sits on the board of more than a dozen portfolio companies, and talks with over two dozen startups a week about potential funding.
How did he develop this powerful platform and brand?
Well, he’s also made amazing early bets over the years like Calm (meditation app worth $2bn), Robinhood (stock investing app worth $12bn) and over 150 other investments.
Today i’m going to tell you more about Jason and how he made himself into this powerful figure in the tech world.
Early Beginnings
Jason Calacanis was born on November 28, 1970, in the Bay Ridge neighborhood of Brooklyn, New York.
He was just your average Brooklyn kid in a middle-class family. And note that in the 1970’s Brookely was not the Brooklyn it is today.
It was a far rougher and more crime-ridden place, rife with gangs. Today’s Brooklyn is like the Disneyland version of the one you would have experienced in the 1970’s.
But it was in these humble beginnings that Calacanis learned grit. He did traditional jobs for the youth of his time… he delivered newspapers, worked at a local ice cream shop, etc.
He wasn’t born with a golden spoon in his mouth like many of the other folks that made it to his level today.
And you can see this in his blunt, gut-driven style today. A style that is often described as being the ‘loudest guy in the room’.
The Rise of Weblogs, Inc.
Calacanis’s first major foray into the tech world came with the founding of Weblogs, Inc. in 2003.
He was one of the first in these early days to recognize the potential of blogs as powerful content. He and co-founder Brian Alvey created a network of targeted blogs covering a wide array of topics, from technology to travel.
Among these, Engadget and Autoblog stood out, quickly gaining traction and becoming go-to sources for enthusiasts.
Note that at the time investors were very skeptical that these content plays could be profitable. But Calacanis was able to drive substantial ad revenue.
And in 2005, AOL acquired Weblogs, Inc. for a reported $25-30 million.
Lessons from Weblogs, Inc.
- Identify and Exploit Niches: By focusing on specific interests, he was able to build dedicated communities that attracted advertisers.
- Innovative Monetization: At a time when monetizing online content was still a challenge, Calacanis proved that with the right strategy, it was possible to turn a profit.
The Mahalo Experiment
Soon after his exit, Calacanis launched Mahalo in 2007.
Billed as a “human-powered search engine,” Mahalo aimed to curate search results and provide high-quality answers to user queries, combining the best of human expertise and algorithmic efficiency.
The platform initially garnered significant attention and funding, raising $20 million from prominent investors.
However, Mahalo faced fierce competition from Google, and the rise of social media and changes in search algorithms posed significant challenges.
Despite a pivot to content creation and video production, Mahalo eventually shut down in 2014.
Lessons from Mahalo
- Adaptability and Resilience: Although Mahalo did not end up as a success story it demonstrated Calacanis’s willingness to pivot and demonstrate very strong resilience for nearly 7 years.
- Staying ahead of industry shifts: Mahalo’s challenges, especially by Google, taught Calacanis about the importance of staying ahead of industry shifts.
The Angel Investor
In the years following Mahalo, Calacanis shifted his focus to angel investing. He founded the LAUNCH conference in 2010, providing a platform for startups to showcase their ideas to investors and industry leaders.
This put him at the epicenter of startup innovation and allowed him to identify and support promising new ventures.
He made early bets into companies like Uber, Robinhood, and Calm. And it is this knack for spotting potential in fledgling startups that has solidified his reputation as one of Silicon Valley’s most astute investors.
Lessons from Angel Investing
- Diligence and Patience: Calacanis’s investment approach is based on researching and having a strong view on the space that the startup is in before investing.
- Network and Influence: His extensive network has been instrumental in his success as an angel investor.
The Power of Personal Branding
There are few in the valley that are as astute at personal branding as Calacanis is.
He makes it very hard for you to ignore. Because he makes himself present in so many places and has a style that forces people to pay attention.
At the same time… although some folks may not be his biggest fan, what you pretty much always hear is that they respect him.
Lessons in Personal Branding
- Authenticity and Engagement: He is authentic to himself and has that ‘take me as I am or get out of my face’ style that has served him so well since his upbringing on the rough streets of Brooklyn.
- Leveraging Platforms: Calacanis amplifies his reach and impact by being on a plethora of podcasts, social media, and conferences.
I hope you enjoyed and took inspiration from my article about Jason Calacanis.
If you’re interested in learning more about Jason Calacanis and his investment style, I recommend reading his book, “Angel: How to Invest in Technology Startups – Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000”. It’s a quick and excellent read.
Now for a word about my firm, A2D Ventures
A2D Ventures is Southeast Asia’s prominent early-stage venture capital firm, syndicate, and investing platform.
The firm invests in innovative and impactful companies across various sectors, with a focus on supporting entrepreneurs who are building the future of Southeast Asia.
Inspired by how well Jason’s syndicate runs – we at A2D; perform smart and thorough due diligence on all startups we invest in and have a competent team working on curated deals.
Using our digital-first platform and investment process – we communicate with transparency to our syndicate members and founders alike while ensuring our investors get quarterly business updates for the startups they invest in.
