January 24

BoringBack — Why a Boring Business Has Sex Appeal

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Seduced By Sexy

The idea for my first business, Twistage, came to me while I was reading an article about iTunes. The music industry was struggling with piracy and being dragged – kicking and screaming – onto the Internet. I was acutely aware of what was happening to the music business. It wasn’t just from reading articles either. My then girlfriend (and now wife) was the music editor at People magazine and between appearances talking about Britney and Christina on shows like Access Hollywood and Entertainment Tonight, she would regale me with stories about declining album sales and frustrated label execs. I was closer than most to seeing how the sausage was made, but despite watching all of the butchering, there was something so…sexy about the music world.

As cool as music was, video seemed even cooler. So when I reached the conclusion that online video would, in the coming years, dramatically alter the landscape for traditional broadcasters, I pondered the kind of business I would build so that I could ride this impending wave. Then I set out to do it. Despite how appealing the business looked from my vantage point, it was tough to get traction. It took two-and-a-half years to raise dollar one from investors. And then there were the pivots. We went from b2b content distribution to a p2p content portal and finally landed back in the b2b world with a platform for online video publishers. Whichever iteration of the product we were developing, however, always oozed sex appeal in my mind. We might have been a bunch of nerds building technology, but we were doing it in the media space.

It didn’t take long to cast aside whatever illusions I had about the inherent coolness of our offering. Sure, we powered the video on pop culture staples like PerezHilton and Fast Company, but it only takes one or two 5am “This is an emergency — none of our videos are working!” phone calls to realize what we truly were: a chassis. We are absolutely integral part of the video ecosystems of our customers. But they were the sleek lines and the high-horsepower engines. Us? We provided a platform that brought everything together so that they could drive.

Embracing My Boring Ways

Bored Girl In spite of my ultimately coming to grips with the kind of business we were, I would never have predicted that I would legally incorporate my next business with the name “Boring But Great, Inc.” And if you’re wondering, that is the actual legal name of my current startup. (We’re doing business as Vendorful because Boring But Great is a mouthful!) Sure, it’s a funny name, but it also speaks — very, very honestly — to what we’re building. Our mission is to create products that improve the buyer-vendor dynamic, ultimately improving ROI. Still think there is a thin veneer of sexy? The first product we developed focuses on RFP facilitation. How about now? Indeed, any time we give someone a demo and hear comments like, “That’s really cool,” I feel compelled to offer a correction: there is nothing “cool” about RFPs. 🙂

Lest you think that working on a “boring business” means that you don’t get to do all of the sexy entrepreneurial stuff, don’t worry – you do! You absolutely get to avail yourself of the subtle pleasures of running payroll, reviewing contracts, filing taxes, and cold calling – each of which will dazzle the people flanking you at the next dinner party you attend. And let’s not forget iterating on your PowerPoint deck, freaking out about your next round of funding, and the ever-so-sexy reorganization of your Kanban board. (If you’re one of the many first-time entrepreneurs who have reached out to me, you know that it’s a goal of mine to help reset expectations about what it means to start a business. While startups might be portrayed in a glamorous light in the media, the day-to-day reality of running a new business is far less sexy.)

Two Kinds of Businesses

Here’s the deal. Starting a business is hard work irrespective of the idea. If you take pleasure in masochism, then you might well be cut out for life as an entrepreneur. Should you choose to go down this path, I would encourage you to prioritize “broadly useful” over “really cool.” This is not to suggest that these two concepts are mutually exclusive. Indeed, YouTube has built an amazing business by being both broadly useful and really cool. There are literally billions of possible video creators and billions of possible video viewers. YouTube’s offering absolutely meets the criteria of providing value to a large audience.

On the other hand, consider Salesforce. It’s an amazing company with – by all accounts – an amazing culture. People who attend their Dreamforce convention rave about it. Everything about that business exudes awesome with the exception of the core underpinning of the business: they provide tools that help salespeople sell. Yes, I admit that at this point in Salesforce’s evolution, that assessment is a bit reductive, but if you distill their offerings, that’s basically where you end up.

The TL;DR Take

Ultimately, whether your business has surface-level coolness isn’t important. Work your ass off and find a way to provide value to a large market and execute. If you can do that, your customers and investors will think your business is sexy as hell.


business, startup