Recently, I’ve had the chance to talk to a lot of talented people who are working on new projects or new startups, most of which aren’t really companies yet, but all of which are interesting to various degrees. It’s quite a privilege, to be trusted by people who are sharing ideas that are important to them, and it’s exciting, because seeing people’s creativity is always inspiring.

But as I talk to more and more creators/founders, I find myself repeating a few of the same suggestions, questions, and conversations, and I thought more people might find the perspective useful. A disclaimer: I may very well not know what the hell I’m talking about. That’s true for almost everybody who opines on matters of “startup advice”, though. A few people have told me they found the feedback useful, so here is the way the conversation usually goes:

• What do you consider “success”? This is one of the first questions I ask people, and usually the one they’re least willing to answer. Sometimes there’s a clear “well, we offer pet food reviews, and we want to be the biggest pet food reviews site on the web” answer, but as often as not, people plug away at something without a clear idea of what they’re working toward. You can’t say what resources you need unless you know where you wanna go.
• Why do you need money? This flows naturally from the preceding question. People ask me, with varying degrees of directness, to either help them get money or to introduce them to people who have money. (I don’t invest money in startups.) When I ask what they need the money for, it’s great to hear “Oh, our system admin woman is part-time and we want to bring her on full-time.” But as often as not, the reply is “Well, you know, for stuff!” Don’t be that person.
• If you need money, how do you want to get it? There’s such an overwhelming tech industry bias towards this archetypical narrative of “first you get angel funding, then a VC round, then a bigger VC round, then you’re set!” And the vast majority of the time, that’s horseshit — you’re not set at that point, you’ve just got a lot of stakeholders. Increasingly, when appropriate, I’m recommending that people max out their credit cards (even evil credit card companies only want a tiny fraction of the return that VCs do), or run a Kickstarter campaign, or do other things to self-fund until they’re further along so they can retain control and power over what they’re creating. That’s not to say venture investing might not be the right choice for some creators’ goals — it’s just not the only option for making something great.
• VC is not a magic bullet. Part of the reason I recommend some small degree of financial independence for creators is that I’m just saddened by how many people see getting venture capital funding for their projects or startups as the end goal instead of as merely a milestone that reflects a starting point. I alluded to this a few years ago with the starting line is not the finish line, but the simple analogy is that you train for a marathon with months of running, and then you begin running the marathon. Getting VC funding is the starting line, not the finish line, and you’ve gotta actually do the running.
• Assuming you succeed, what do you want that success to look like? This is the corollary to the first question. If you make a great app that gets tons of users, but it’s covered in ugly ads instead of the cleanly designed experience you initially created, will you be happy? If you make a huge amount of money but it’s because you’re selling tons of personal data on your users or clogging up the web with absolutely crappy content, will that be a fair trade to you? Is the continuum of choices in these matters something you’re willing to compromise on in exchange for making sure your kid goes to college? What if it’s just to buy yourself a fancy car?

I’m far from the first person to ask a lot of these questions, but many of the entrepreneurs I speak to, especially first-time entrepreneurs, seem to never consider these questions. Think about them, write down your answers, and then refer back to them as you have conversations with advisors, potential investors, and even your customers.

As with almost everything else, success comes from you knowing who you are and what your values are, and from being able to recognize success because you’d already defined it for yourself in the first place. Diving into an endeavor without those fundamentals is a pretty sure recipe for making sure you never accomplish the thing that it turns out you wanted.

Oh, and I never ask whether people are making something meaningful that they care about, or if they’re just making something because they want to have a startup. Because I’m lucky enough that I don’t have to endure the conversations with people in the latter group.

Related Reading

• Making Something Meaningful, from 2006.
• Re: Vision, from 2009.