Repeat after me, I will not do another startup as a non-technical founder unless…

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(above: the original paper mockup of Twitter by @jack)

I have spent nearly the past year working on my startup MyFavorites and I thought this was finally the time that I had learned all my lessons on failure. I hadn’t.

What I have learned this time around are a slew of things I can’t possibly begin to document. Some of these lessons I can’t even see yet, but there are some obvious ones.

I’m a non-technical founder, aka I can’t program. I have held every role in the book at web companies, including being a programmer back in the late 90s, so I understand web technology — I understand what it can do and the limitations. I leaned towards the business/marketing side of things many years ago. I’ve been reading about new technology and startups since the days of the Business 2.0 and Red Herring publications in the 90s, and then I was the 4th writer at TechCrunch back in 2006. I have consumed nearly every article on TechCrunch the past 5 years and tried many early-stage apps/sites. I can look at a new service, software, website, mobile app, and my mind just starts spinning with ideas for improvement, marketing, and monetization.

I will not do another startup unless:

  1. I have full paper mockups for every screen of the user experience, and I have had real people use the experience via these paper mockups. I have to fully think out the user experience more than I ever have before — and I need to do it before I start hiring a graphic designer.
  2. I can program it. At least a minimal version of it. Dennis Crowley learned what he needed to get the first version of Foursquare out, and Philip Kaplan dabbles a bit pushing out little projects here and there.

If I can’t program it, then I need a technical co-founder (there’s no room for an idea guy). Finding cofounders is just like finding a significant other. You don’t marry someone immediately. You date a lot — most last an hour, some can last months, others for years. Finding “the one” is just as difficult as it is when marrying. You both have to believe in the same principles and what you’re looking to accomplish in the future. You have a baby together — or babies. Long distance doesn’t work.

What happens when you aren’t programming a web/mobile startup yourself is that the project costs escalate and get out of control. Even if you get a fixed price on your project, someone’s going to get screwed — you or the programmer. 110% of the time you have not defined every nook and cranny of a project. And what if it does take off — there’s ongoing maintenance, support, tweaks, features, etc.

Being a non-technical founder is difficult, because the balance of work shifts greatly during pre-launch. At first, the non-technical founder (possibly with the technical founder) is hopefully bringing the user-experience to the table — and maybe money for design and marketing. (But I’m learning you shouldn’t be wasting any money on design or anything — put out something simple. If it’s awesome, the people will come and use it.) Then the technical founder does the programming while the non-technical founder sits there buying sandwiches. Then launch hopefully occurs, and then the non-technical founder can really have a role — customer support, marketing, social, blogging, press, bizdev, etc. Meanwhile the technical founder is doing support, tweaks, new features, and scaling.

There’s a reason startups typically happen by college kids — they have nothing to lose and everything to gain. They aren’t tied down by families, wives, kids, mortgages, etc.

So I’m contemplating my next steps in the work aspect of my life. I question whether I should be trying to start companies myself — whether I even want to run a company. I’m not an operational manager and I’m not a project manager. I think if I was working on a solution to something that I truly passionately believe in, then I may take another stab, but I don’t know when or if that problem will ever exist for me. Meanwhile, I get fascinated by a lot of cool stuff that’s being built by people.

I know one thing, I need to start blogging again. I love consumer internet startups and I know I could lend a lot of value on the product/marketing/bizdev/monetization/sales/community/rolodex side of things. I think I may want to work for an investor, or group of investors, or start a small fund and invest some money from people looking to get into these exciting times we’re living in. That way I’d have a vested interest in the success of the portfolio and I would work to assist the startups (and source new promising startups that look to change the world).

Much more thinking too come, but for now I’m going to enjoy and appreciate this awesome summer that’s upon me — new home, marrying the girl of my dreams, trip to Europe, and all the other awesome things to do in sunny Buffalo.