wheresitworking?

As an founder at a bootstrapped or early-stage startup, you have the opportunity to really utilize the strengths and skills you possess as an individual. You also have to do things that require (force) you to use your weakest skills or traits. Often this means having to step out of your comfort zone and do something that is generally uncomfortable. It may be personality related stuff like speaking in front of a group, understanding relationships, making quick decisions, etc. Or they may be larger “business” oriented disciplines like marketing, sales, front-end development, etc. Either way you look at it, whatever you suck at, you’re probably going to have to do it as an entrepreneur. Now, the more co-founders you have, the better the odds that you’ve allocated work so that you’re doing what you’re good at, and they’re doing what their good at. If you have co-founders with similar skills and personalities, this isn’t going to be the case; someone is doing something they’re not good at. And if you’re a solo founder, you’re spending a lot of your time doing things you suck at. As you grow and can hire people to take on responsibilities, and off-load the some of the things you might suck at,  but when you’re small and scrapping, most of the heavy work falls on the founders.

Doing things you suck at generally means stepping outside your comfort zone. I’ve been doing sales, true sales, for a few months now at SwellPath. Before this we worked entirely off word-of-mouth and referrals. Those kind of sales are easy. Reaching out to someone who’s never heard of you, doesn’t operate in your town, doesn’t think they need your offering, and is slightly pissed that you’re bothering them – is a lot different then WOM and referrals. If sales is your thing, maybe this is no big deal. If it isn’t your thing, it’s a very uncomfortable thing to do. I’ve been doing this kind of sales for years – when I was in high school I sold Daily Herald subscriptions door-to-door in the Chicago suburbs. I’d get yelled at by elderly women who tole me “you all” had destroyed their flower gardens with errant paper throws. I sucked at sales then – sold very little papers and went and found a new job after only a few weeks. I was also forced to essentially cold-call on people at RYZ. I pretty much failed. Sales is still something I’m not great at, but I can’t quit this job. Like most people, I generally don’t like doing things I’m not good at. So every day for the last few months, I’ve stepped outside of my comfort zone and slugged through it. But a funny thing is happening; I’m starting to really like it.

The pitch is improving, and we’re able to more easily convey our value proposition to leads. Over time we’re always increasing the value in our offering, so that makes things easier also. But I also am improving. I’ve read dozens of blog posts and (parts of) books; I’ve spent hours and hours thinking about how to respond to concerns from leads. I’ve thought hard about how I personally interact with leads (I suck at “listening” to people, and much prefer to talk about myself). By forcing myself to do this constantly, I’m improving my self worth and gaining skills.

It’s not limited to sales either; this is happening for me in other ways. The initial journeys outside the comfort zone, and feeling your weaknesses exposed (which feels like those dreams where you show up at school naked), are stressful, awkward, and mentally painful. But the price you pay early on, pays off big when you start to figure it out and put it all together. I’m finding it to be one of the most rewarding aspects of this journey at SwellPath.

Now, I don’t think this kind of self-improvement happens to all entrepreneurs. Keep in mind I’m not just making my entrepreneurial assumptions based on my personal experience at SwellPath. I am reflecting on the experience I have working for 5 startups before SwellPath. Three of those had co-founders (one of those was a solo founder who’s wife ran half the business, and I count as the co-founder), and two had solo founders. Including John, that means direct experience with 9 startup founders. In addition, I have countless conversations with other founders. So, I’ve seen founders who failed to self-improve – and the results of this weren’t pretty.

I’ve obviously improved my skills in the positions I’ve held working for others in the past; I’m not suggesting that being an entrepreneur is the only way to improve one’s worth in business. But I think that the improvement is accelerated and it is exponentially more effective when it comes from the kind of atmosphere and pressure that being a startup founder provides. One more reason I am loving the experience at SwellPath, and love supporting the entrepreneur community and entrepreneurial spirit in general.