I have been an entrepreneur since 2009.
I was the CEO of nearbuy.com (which I founded in 2015), from its inception until 2019. Prior to that, I was the founding CEO of Groupon's India business in 2011.
In my current avatar, I am bootstrapping an education company, while creating content across multiple platforms (5.5Mn+ followers as of Mar '22) and mentoring founders.
While I have been an active angel investor since 2015, I have for the past year done more late-stage deals (Series A), where the PMF is well established, there are reputed institutional investors backing the company and I am able to get an allocation.
There are 2 types of deals I get access to:
1. Late Stage, mature deals, where its almost impossible to get on their cap table!
As a content creator, I work with a lot of growth stage startups, helping them with distribution and content. To have skin in the game, I prefer taking part equity for such partnerships.
As my personal brand has grown, so have such opportunities to work with high-growth startups.
As an extension, I now ask for a higher allocation of equity than what I have personally. And I use this syndicate to crowdfund.
These deals, by design tend to be more expensive ($50-100Mn+ post-money valuation) but come with a lot less risk.
2. Early stage, super risky deals
As a founder I get a steady deal flow of super-early startups raising a pre-seed or seed round.
Herein, I usually bet on the team, because there is frankly very little information to drive judgement.
As a preference, I try and limit such deals and also take slightly lesser allocation, while giving us the opportunity to pro-rate invest as the company grows.