Why Sales Success Is Especially Critical for Bootstrappers

[Note: This is a guest post by Charlie Gilkey: A friend and all-around brilliant dude who writes at Productive Flourishing.  You should click here to check out his stuff].

When it comes to selling, I’ve seen three main perspectives in my years of advising entrepreneurs:

  1. People who love selling
  2. People who don’t love selling but understand that it needs to get done, and . . .
  3. People who absolutely detest it and don’t want to have anything to do with it

Let’s get real here.

If you’re in business and you’re in Camp #3, you either need to get into Camp #2 or get out of business. You can’t make yourself love something you don’t, but you can still do it effectively.

If you’re building a bootstrapped business – that is, a business that doesn’t start with external funding or significant upfront capital – the only way you can keep the lights on is to sell whatever it is you sell. No sales, no lights, game over.

Avoiding Failure Isn’t The Same As Epic Winning

That black-and-white failure scenario rarely happens, though, because we bootstrappers keep our overheads low. Our businesses are launched off kitchen tables, bedrooms converted into offices, and coffee shops.

Instead, what happens is that many bootstrappers find themselves squeaking by month to month but never really getting a positive cashflow spiral to catapult their businesses forward. That’s one of things that gets us stuck in Stage 3 – we have enough capital to keep operating at our current level, but not enough to grow to the next level.

Our next launch looks like our last launch because we have the same time and cashflow as we did last time. We can’t hire the talent we need to because we don’t have sufficient margins or reserve to pay them. We can’t beachhead into more profitable markets or segments of our markets because the hurdles are higher and we don’t have the resources to make the jump. And so on.

Yes, we can build better brands. We can improve our marketing efforts. We can develop better products.

But the bottom-line is that the better we get at selling, the faster our businesses grow to whatever right-size it should be for us. If you’re not continually improving your sales effectiveness, it will catch up with you.

Why Focusing on What People Want Is Killing Your Sales Success

Sales success is important for every business, but funded startups and established businesses have (what they refer to) as a “runway” to figure out who their customers are and what they want. I’ve always found that backwards, but that’s precisely because I’m a bootstrapper, and in our world, we start with who the customers are and what they want. Everything else is secondary.

At least, that’s what those of us in Camp #2 wrongly think. It’s not what people want, it’s what people will buy that counts. I’ve wanted a Corvette since I was 13, but I don’t think I’ll ever actually buy one. The Corvette marketers can do everything they want to woo me, but my wallet’s never coming out for that one.

And here’s the catch: you don’t figure out what people will buy from you until you start actively selling them stuff. A survey asking people what they want and would buy doesn’t cut the mustard either, for many a bootstrapper has been let down when 20% of their surveyed people said they’d buy something and 1% of those very people actually buy what they said they would.

Listen, Sell, Assess – Rinse and Repeat

I haven’t said anything groundbreaking here, and that’s fine by me because it wasn’t my intent. My intent was to remind the people in Camp #2 and #3 to focus on the basics because the alternative of not focusing on sales effectiveness leads to either direct failure or a long plateau of mediocrity. (I don’t have to remind the sellaphilliacs about this one – we have other conversations. 🙂 )

Relentlessly focus on who your customers are and what they are actually buying. Do the marketing you need to develop the know, like, and trust with them. But selling stuff (in a way that’s in alignment with you and your brand) is paramount.

If your sales efforts are successful, figure out why and keep doing what works. If they aren’t successful, figure out why they didn’t work and don’t keep doing the same thing. Sales mastery is something that takes years to learn; it’s not you, it’s just the lay of the land.

If you’re in business, you’re always going to be selling something. Consider this an invitation to make the journey work for you – but make sure you’re doing the work of the journey.

Charlie Gilkey shows entrepreneurs how to get and keep momentum in their businesses and is the founder of Productive Flourishing. His work is routinely cited, showcased, and shared in places like Inc.com, BNET, Project Domino, Lifehacker, Copyblogger, Problogger, Zenhabits, and others. His forthcoming book, Beyond Bootstrapping, helps entrepreneurs and small business owners build better businesses from the business they’ve already built.