Interview With Sunny Dhillon

Explore private investing insights, the importance of strong teams, emerging innovation themes, impact goals, investment challenges, lessons learned, preferred industry sources, personal hobbies, and a recommended book in this informative blog post.

How and why did you get started in private investing?

Company formation at the inception stage is what I’ve always found most interesting. Working for big corporates and investment banks taught me one thing really well – these 800lb gorillas don’t get startups nor do they have innovation in their DNA. They do have rich balance sheets to offer fat ARR-generating customer contracts to flocks of external innovators though – that’s really where I wanted to come in. Helping startups get customer contracts from corporates who didn’t (figuratively) speak their language.

What is the single most important thing you value in an investment opportunity?

Team. Team. Team. You’re working together for 5-7 years on average before an exit event so we have to make sure we get along and can work well together. Is there a strong technical cofounder on the initial roster? Is the product one that has been thoroughly well researched before seeking funding? Has the team gleaned unique insights into the pitched market opportunity based upon prior, deep professional and relevant market experience? Do they have a bunch of spring-loaded customers ‘ready to go’ as soon as we invest? What are their organic marketing plans and unfair distribution advantages that de-risk our initial investment for a go-to-market plan?

What are the best innovation themes that you see in the market today?

Vertical applications of computer vision to highly automatable, low-skilled, repetitive tasks – e.g. mowing lawns, parts of the home building process, packing groceries. I also see disruption of traditional banks and financial infrastructure in crypto through flash loans, yield farming pools, and other DeFi initiatives as very interesting.

Beyond economic return, what kind of impact do you hope to make with your portfolio?

The goal is to help expand our global production possibility frontier – only strides in technology can help make that happen during a single life time. Enriching quality of life and bringing communities closer together are absolutely other noble goals in the pursuit of strong returns for our fund investors.

What’s the most pressing challenge or pain point in managing your day-to-day private investment activity?

We’re in the midst of fundraising for our new fund right now and the limited partner community is an incredibly opaque one. There’s not an efficient way to know who is in market for early stage managers, how over/under-exposed to venture they may currently be, and/or when they might be ready to deploy additional dollars to new managers. We thankfully have pre-existing relationships that we have leveraged, but the LP part of our business is definitely inefficient in how it currently allocates capital.

What is the hardest investment lesson you’ve learned and/or the biggest investment mistake you’ve made?

I  have a giant anti-portfolio. It’s too depressing to dwell on this too much right now to be honest. 🙂 In brief though, don’t always worry about the market or product being pitched – sometimes just go off of your belief in a founder. Products pivot – integrity, drive, and intelligence don’t.

What are your favorite industry information sources and/or services?

Industry press (Techcrunch, WSJ, etc.), conferences, etc.

Please leave us a book recommendation.

Troublemakers by Leslie Berlin – Talks about the founding stories of Atari, Genentech, Apple, Roam, and other Silicon Valley companies.

What’s your favorite non-business interest or hobby?

I go to Comic Con every year – I’m a huge geek! 🙂

What’s your take on the private market overall?

Scored: 8