My typical lunch break activities.

Learnings from a Year in Venture Capital

David Cheng
Startup Grind

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It’s been about a year since I joined DCM Ventures and while I would say 75% of my day is spent flirting with startup dudes — mostly at demo days, tech meet-ups, coworking spaces, and the occasional coffee shop — I have definitely picked up some other nifty skills.

Here are some of my learnings so far for any others getting started in venture or just looking to learn more about the industry:

1. It doesn’t matter what side you’re on, you still got to sell!

So sell yourself, sell your firm, but don’t sell your soul. Back when I was at Accenture, my buddies and I came up with a ratio that we accepted as the governing metric for the rest of our lives. We called it the Age to B****-To ratio or A:B-T ratio. Essentially, your age relative to how many people you bent over backwards or forwards for. Buy side is where you call the shots right? Nope. Not saying that this is a bad thing, if anything I’ve learned how important of a skill selling is.

2. You will constantly be asking for help, so get good at it.

Company X walks in the door and is in the business of selling Ys to millennial Zs. You know nothing about X, Y, or Z but you think that it will still be a big business. What do you do? Open up LinkedIn, RelateIQ, and Facebook because now is the time your mom’s advice about making smart friends comes in handy. Of course, you’ve also got to do your own research — banking reports, CapIQ, Slideshare, Quora, Github, Survata, SurveyMonkey, and even Techcrunch will come in handy here.

3. It’s all about empathy.

You may never buy Ys and you can’t imagine any Zs who will but maybe this will sell really damn well to baby boomer XYs. Keep an open mind. Who would have thought that one of the world’s most valuable startups would be built on strangers picking you up in Toyotas?

4. The earlier you are, the more it’s really about the team.

Unlike other asset classes, venture is way more hands-on. The best piece of advice that I’ve gotten is to make sure that you’re willing to go down with the entrepreneur if things go south.

Bad boys 4 life, ride or die.

If you can’t stand the entrepreneur or team then don’t think about investing. It doesn’t matter how big the market is or how good the product is. You’re going to be spending a lot of time with them.

5. The best thing you can do for the longevity of your career is to not be a dick.

Regardless of how stupid the idea is or how arrogant the entrepreneur is, be nice. Whether it’s getting an entrepreneur to agree to terms or turning down the world’s worst business plan, you never know when your douchebaggery will come around. Conversely, you never know when your graciousness will save you.

6. Don’t sit on your ass and wait for good things to come to you.

The pretty girl is never going to ask you out. Your muscles won’t just attach themselves to you out of nowhere. The great deal will never land in your inbox. Just like in most things in life - you have to find the good stuff, the good stuff won’t find you.

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David Cheng
Startup Grind

Partner @ DCM Ventures investing in consumer technology, vertical software, and marketplace startups