I have a confession to make. My name is John and I'm a bootstrapper. I've seen a lot of mega-corporate types giving advice on how to sell to us lately. Most of their advice is terrible because it's based on what's best for them. With all due respect, anyone who works for a large corporation doesn't have a clue about the bootstrapper psychology. If we're in your target market, here's some free advice on how to sell to us.

What is a bootstrapper?

For those of you who don't know, a bootstrapper is an entrepreneur who finances their company out of their own pocket. Many have a successful corporate life behind them and have accumulated enough wealth to invest in themselves. Many people think we're crazy - they may be right. Before even starting to spend any of our own money, we take a six-figure pay cut to quit our corporate jobs and build our own future.

We're not like the entrepreneurs at Pied Piper on the HBO sitcom Silicon Valley. They're spending someone else's money. Some may guess that Paris Hilton is a bootstrapper. She's not - she's spending Daddy's money. If you're a bootstrapper, you're going to spend a lot of your own money before you see the return on your investment in yourself.

Most bootstrappers don't pay themselves for a significant period of time. I was recently selling to another bootstrapper who put things in perspective for me quite nicely, "Why should I pay you when I'm not paying myself?" Tip number one for those selling to bootstrappers - have an answer to that question.

It takes huevos to become a bootstrapper. We're taking all of our chips and pushing them towards the center of the table while holding a pair of eights. There's a fine line between courage and stupidity. Depending on the day, I might have a different sense of what side of the line I fall on.

One thing we all have is an unshakable belief in ourselves and a disdain for putting our fate in someone else's hands. We've seen the politics and inefficiences of the mega-corporate world and don't want anything to do with it. We have an unshakable belief in ourselves that pushes us through seemingly insurmountable challenges.

If you're not humble when you start out as a bootstrapper, you soon will be. Despite our belief in ourselves, we've been kicked in the teeth enough to know that it's a tough world out there. What makes us different is that every time we get kicked in the teeth, we pick ourselves up and get back in the fight.

We're accountable by definition. If you're in a corporate job and aren't performing, you'll continue to pick up a paycheck until the corporation overcomes its inertia and fires you. If we don't perform, we don't get paid - period, punkt, punto.

That description probably gives you the impression that we're unrealistic jerks. You're probably right. But we buy a lot of goods and services. We pay our employees before we pay ourselves. And we love every minute of it.

You need to have a compelling value proposition to sell to a bootstrapper.

Dr. Flint McLaughlin of MEC Labs has what I think is the best definition of a value proposition. According to Dr. McLaughlin, a value proposition is the answer to the question, "If I am your ideal prospect, why should I buy from you rather than any of your competitors?"  Let me add that the biggest competitor is always the choice to do nothing. So if you want to sell to a bootstrapper (or anyone else for that matter), you need to ask yourself that question. And you need to be painfully honest with yourself about the answer.

If your value proposition is that you are "innovative", "customer-focused" or "best in class", you'd best rethink that. If you haven't noticed, everyone uses these trite cliches to the point of rendering them meaningless. For SMB companies, the best way to have a unique, compelling value proposition is to focus on a narrow niche and become an expert within it.
If you want to sell to bootstrappers, have a value proposition that ties directly to results - lower costs or higher revenues.

You need to understand how bootstrappers prioritize purchase decisions.

This one is easy. We prioritize purchase decisions or hires on the perceived ability of that purchase or hire to result in us saving money or increasing revenue. Not a lot of hidden meaning there. Cash flow is the lifeblood of any small business and it's even more important when the business owner is paying the start-up costs out of their own pocket. If you want to sell to a bootstrapper, make sure to communicate how that purchase will enhance cash flow.

We're only concerned about image or brand or other esoteric concepts in terms of how they will increase cash flow. I don't care if my brand conveys that my company is insouciant, sassy or brooding. I want my brand to convey the message that my company delivers value to customers and encourages potential buyers to consider me. That might change when I get a little higher on Maslow's Hierarchy of Needs chart.

Many of us have achieved the physiological level - we have sufficient cash flow to keep the doors open. We're now working on the safety level - brining in sufficient cash flow to let us breathe a little and start expanding. We don't have time to think about esteem and self-actualization, it's a vague concept that has nothing to do with the world we inhabit. For those selling  to us, I would advise asking the right questions to find out which level we're on and helping us get to the next one.

Summary

I hope that gives you a little insight into the psychology of a bootstrapper. While we may be difficult to sell to, we have tremendous loyalty to vendors who understand and help us. From the services side, we couldn't survive without some of our vendors. They perform functions that employees would at a larger company. Regardless of whether you sell products or services, keep in mind that we're looking for any kind of help that gets us to the next level.