Who I'm Writing Beyond Bootstrapping For

A while ago, I went in to have my orthodontic braces adjusted. I was chit-chatting with Jessica, the orthodontist's assistant, and she asked what I did. I told her what I tell most people on the street: I'm a small business consultant. (Editorial note: this post was originally drafted in April 2011; it's been longer than "a while" since I've had braces.)

You'll note that that's a bit different than how I describe my services here. Outside of the echo chambers of the blogosphere, people don't quite get coaching, online business, entrepreneurship, Social Media strategy, and the whole nine. Even the tagline a la Michael Port tends to be too much in a purely social, chit-chatty environment, so I give an accessible, easy version.

She leaned over and whispered "I have my own small business. I'm struggling because I'm trying to get my taxes prepared right now."

I could tell that she was open to talk about her business, and I'd much rather talk about business than try to run through the deck of small talk cards that flip through my mind. I started asking a bunch of questions about how it was going, what she was having challenges with, and so on.

She had a house-cleaning business with two employees. She first said her business wasn't growing because she thought she needed some more employees. I asked a few questions, crunched a few numbers in my head, and, given what she told me, let her know that she was losing $800 a month by not hiring another employee.

She looked at me and asked why I told her that; she preferred not knowing. I asked why she tells her patients that they need to floss. In both cases, it's just what we do.

One of the reasons she hadn't hired another employee was because she didn't have the time to interview and train the new employee. I asked if one of her current employees could train a new employee. She hadn't even thought of that, but figured that would work.

She still wanted to do the interviewing, though, which I completely understood. At that scale of business, you absolutely have to have the right people.

I knew something was off, though, so I inquired further about whether she could handle any more houses than she currently had with her current employee set. It turns out that she could handle four more houses at her current capacity. Her current employees would also like to have more houses and work, too, so I couldn't see why she would want to increase managerial overhead by bringing on someone else. When I put it that way, she couldn't see why she wanted to do it either.

The conversation went on in this fashion for the rest of my few minutes in there. You can probably anticipate that we started talking about her marketing and promotion activities, since that's the natural thing to do when you're not at full capacity. If she acts on some of the stuff we talked about, she could make between $2,000 - $5,000 this year on her side business. It could be more if it starts a positive momentum spiral that she leverages well.

We didn't talk about anything revolutionary or innovative in that 20 minutes. Aside from the fact that it's hard to do that with someone's fingers in your mouth, that's not what she needed. She needed to focus on business basics. All of the information is out there, but it's not reaching Jessica. Or Jessica's not reaching for it.

It's Our Fault that Jessica Isn't Getting the Information She Needs

Can you blame her, though? Most of the business literature out there is focused on Big Business. Do we really want to hear about GE, Starbucks, Apple, Walmart, Intel, Microsoft, and Southwest Airlines anymore? Besides that, the perspective there is so different than the perspective of small business. They're talking about workforces in the thousands, operating capital in the billions, and global dominance and competition.

Jessica has two employees and is trying to figure out how to make a few extra hundred dollars a month. Her primary concern is that her word-of-mouth, referral-based marketing in a neighborhood within Portland is working effectively. She would spend so much time filtering out what's not for her in those books that who could blame her for deciding that the whole lot isn't for her?

I've spoken to a lot of other business consultants and advisors, and there's a bit of disdain for small businesses of the type we're talking about. They're filled with "drama" and "worry" because the owners are too emotionally invested in them at the same time that they're "not taking it seriously." It's been so long since many of those consultants had to worry about putting food on the table that it's hard for them to see that it's something anyone would be worried about. It's been so long that they had to have a full-time job during the day and a second shift at home with the family and don't understand that there aren't enough hours in the day for "continuing education."

The other frustrating thing is that since Jessica can't or won't pay for a guru, those gurus won't invest their time in her, whether that's in their writing, outreach, speeches, or, sadly, when they're sitting in a chair being taken care of by her. The publishing industry also assumes that she won't buy books, so it's harder to get a publisher on board when you're talking about writing a book for her.

Is Jessica in her own way with her business? In a lot of ways, yes. She's scared, overwhelmed, confused, and worried - and it's keeping her from making the strategic moves that would actually make her feel better. She's also balancing the mindset of being a reactive employee with being a proactive businesswoman. There are some pretty distinct operating assumptions at work there, as well as the associated mind shifts that have to happen for her to make progress.

At the same time, we can do better about helping Jessica. We can speak her language and take her business seriously. We can provide resources for her and treat her as if she were one of our high-paying prospects - or might potentially be in a year. We could, but we don't. Most won't.

Much of my work is for the Jessicas of the world - the bootstrappers who moved on an business idea despite not having everything they needed at the start. Up until now, it's been mostly online, but that's just because we needed to build the resources up to do more. We all have to work with what we have to get what we need to get where we're trying to go.

To riff on Shumacher, small is beautiful. Small is also hard. Let's get some help in there where it's needed.