👋, I'm Gautam. I'm currently a Partner at On Deck, leading our investing, business and expansion activities APAC + India. Here's more about why I joined On Deck. Before On Deck, I was at Skillshare, helping drive international (ex-US) product & growth, and prior to Skillshare, I was Quora's first international hire, and worked there for ~3 years. Before that, I was the Founder & CEO of AudioCompass, a company that I built for 6 years. You can learn more about my professional background here. Before On Deck, I was by no means a “professional” investor, but I do spend a disproportionate amount of time speaking, working with, and often investing in early stage founders and teams.

Investing Track Record

I started angel investing in 2010, and took a break from 2014-2017. From my initial cohort of investments, Exotel, Hotelogix, Navya Network, and Bevi are worth highlighting. I started investing again in 2018, mostly via syndicates (Yulu, nPlex, Arpeggio Biosciences, SwayPay, Blue Tokai), but have largely moved to investing directly in founders, in companies like Animall, OSlash, Equi, ION Energy, On Deck, AbstractOps, Airtribe, Fincent, and Glip. I invest in companies to support founders that have a vision of a future that I buy into. From my 2010-2014 cohort, I have 2 exits that more than returned the invested amount, and 2 more companies that will hopefully 🤞 get me to 8-10x of total invested capital for that 'fund'. There are winners emerging from the 2018+ cohort, but it's too early to tell. There have already been several shutdowns since 2018.

What I look for

I generally invest in companies where:

I'm sector and stage agnostic, but generally prefer investing in pre- to early-PMF companies. I get most excited about investing in companies where I can help the founder with thinking through product, go-to-market and growth. I also love to invest in companies where I can learn to apply my skills to a new industry or space!

Value add

In general, I tend to invest $5k - $10k ($100k if the founder allows me to syndicate the deal). In other words, I am not invited to invest because of my cheque size, but rather, because I'm an operator. Here are how some founders (from my portfolio and companies that I have not invested in) have described me:

Partnering with me

For now, the best way to partner with me is to reach out to me via email gautam {at} hey.com. If we have a common connection, ask them to introduce us with some more context (although that is by no means necessary). I also have a syndicate (more below), so I'd love to partner with potential LPs as well as founders.

AngelList Syndicate

My angel investing has resulted in my ending up in a situation where a larger-than-what-would-considered-prudent percent of my net worth is in illiquid, Pre-Seed and Seed companies.