“I’ve Actually Invested Twice” - Rajesh on Diversifying Multiple Concentrated Positions
"I've been in the valley for the last 30 years and I think the valley has been kind to many of us," Rajesh says.
He built his career across startups, larger companies, and advisory roles. He also invested early in pre-IPO companies. Several of them did extremely well.
"What was initially a very small investment ended up becoming a very large value in the market."
Five years of searching
Rajesh didn't act quickly.
"I've actually been thinking about how to diversify for a few years," he says.
The barrier was taxes.
"The challenge obviously is that the diversification creates a huge taxable event."
He watched markets shift. Companies that had driven returns gave way to others. His original investment theses weren't wrong. The environment had evolved.
"Maybe the companies that you initially invested in, your investment thesis was solid," he says, "but the market has changed and they're no longer likely to outperform the market, or the risk associated with having such a concentrated position becomes too difficult."
Why Cache felt different
Rajesh knew that exchange funds existed.
"Exchange funds are offered by other firms and other investment organizations," he says, "but they're always extremely expensive and not as transparent as I wanted them to be."
Cache offered something else.
"What I found with Cache was a company that was leveraging technology, that was very open, that was pretty clear and transparent about how they structure things."
He did the work before committing.
"I did quite a lot of due diligence to really get that sense of trust," he says. "I also looked at the team and was very pleased to see the kind of team that was assembled, and the thoughtfulness of that process and how they approached it."
Investing twice
"I have not invested once, I've actually invested twice with Cache for two diversified positions," he says.
"By diversifying with Cache, I was able to firstly sleep more peacefully because now I am highly diversified [...]"
He's candid that the job isn't finished.
"I think there is still more diversification to do, to be honest," he says. "Sometimes you like to hang on to your darling stocks and you're not very rational as an investor."
Who this is for
Rajesh sees the problem as structural to Silicon Valley.
"I think Cache is a great solution for many, many of my friends, many people that I probably don't even know in the valley," he says. "People who have been early employees or even more recent employees at […] companies in the valley who have very concentrated positions."






















