neilkam

Entrepreneurship is one of the things that makes this moment in history really special — we’re at a point in time where technology is disrupting everything we know about the world and, as a group, the entrepreneurs who are building that technology right now are going to leave a mark our great-grandchildren will learn about in school. I don’t think that’s an exaggeration. But should you be one of those entrepreneurs, in the true sense of someone who starts a brand new company from zero? It’s a personal choice, of course, but how should you even start to frame that question to yourself? I think it’s important to be really honest and ask yourself “Why do I want to do this?”. It’s going to be a struggle with daily peaks and valleys, so you need to have your answer to that question really honestly defined. 

The obvious disclaimer here is that I’ve never started a company from scratch myself. I have been fortunate enough to be there for the journey from 3-4 people up to 150 (where TC is now) and watch a founder from a few feet away along the whole way. And I’ve thought a lot about whether I want to start a company from zero myself one day, either as my next step or sometime down the line. From all of that, I keep coming back to these four potential reasons, at least for my own evaluation. Not all of these reasons are necessarily good reasons, by the way, but it’s really your call which of these are enough for you.

• You can’t NOT solve this specific problem: To me, this is the best reason and would need to be the majority of my rationale if I ever started a company. Many of the most successful companies of the past few decades (think Google or Apple) haven’t come from serial entrepreneurs who’ve jumped from industry to industry. They were born from a perfect blend of the founder(s)’ personal talents and passions with a problem they wanted to solve so badly that they couldn’t work on anything else. It’s really an order of operations thing: these founders didn’t set out to be entrepreneurs first and then find a problem to solve second. The problem found them, and they felt like they were uniquely qualified to solve it so they started a company to do it.
• You want to control your own destiny: Serial entrepreneurs fit into this category, and many of them are very successful because of it. Some people are just happier, more productive, and feel more fulfilled when they work on something that’s under their full control. They won’t want to work for someone else, who may or may not have the vision and ambition that they have, so they would feel limited and pinned down in any sort of larger company. Freed from that, they can find a problem to solve and make it happen. The question to ask here is this: do you dislike working for other people enough to take on everything that starting your own company would require? Or are you just working for the wrong people?
• You want to win: I’m a really competitive person. I hate losing (my brother and I don’t play 1-on-1 basketball anymore because it always ends badly). Most entrepreneurs are like that, because there’s really no more satisfying professional “win” than building something that didn’t exist and making it successful. In a startup, there’s pretty clear accountability for success and failure — there aren’t many other people around to claim the credit or blame. That clear ownership is attractive because it’s the fastest way to build a reputation and, let’s face it, some high school-style popularity in the professional scene. You think Jack Dorsey has 10M Twitter followers or whatever because his tweets are just so interesting?
• You want to make a lot of money: No one wants to openly admit this is a motivator, but if a concentrated earning period in your career is a goal of yours (maybe you want to spend your 40s and 50s traveling), entrepreneurship is one of the only ways to get it. When a liquidity event happens, founders deservedly exercise the vast majority (think 90%) of all employee shares. You’re probably not going to retire off a non-founder employee grant unless your company exits for a number in the Bs, and that pretty much doesn’t happen. I wouldn’t advise a friend to let this be his or her primary motivator, because it probably won’t turn out well, but just be honest with yourself.

Those are four possible reasons to start a company. It’s up to each of us to decide which of these is good enough.

When we were just getting started at Trunk Club, we needed to validate our model and do it fast. That meant getting customers and revenue in the door one way or another. We didn’t have any salespeople or marketing, or much of a product, for that matter. Brian, our CEO, gave me a challenge — find 10 customers in my first week and convince them to buy clothes from us. 

I fancied myself a pretty smart, scrappy guy at the time — but I was really uncomfortable selling. Most smart, ambitious people want their work to speak for itself, rather than having to “ask for favors”, but the early stages of entrepreneurship are a lot about convincing other people to take a risk on you and help the cause. Whether it’s early customer acquisition, fundraising, or recruiting, you can’t succeed if you don’t learn how to put yourself out there and ask for help.

I took Brian’s challenge and reached out to about 75 potential customers in my network. I told them I wanted their help getting our company off the ground. Many of them never responded to my emails and voicemails (ouch). A handful of them might have been annoyed at me (oh well). But within a few days, I had leads on about 20 customers that became an important part of our revenue that first quarter. 

Selling and asking for help aren’t as sexy and talked about as a lot of what you hear about in startup blogs, but I’d argue they’re the most important part of building a company (thanks Brian). Recently, I found myself reaching out to an acquaintance who I thought could connect me with a potential designer recruit. Instead of feeling shy about it, I was honest: “We need help - would really appreciate anything you can do”. He made the connection. I’m glad I asked.