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.

Not sure what reminded me of this moment, but I felt compelled to write about it when I remembered the situation. This was at one of my first jobs; I was a web developer on a team of about 15-20 developers (all-in, front-end to back-end), building a .com. I was what I referred to as “middle-tier”; I wrote HTML and front-end scripting languages, but did a lot of SQL writing to feed data from the web database into the CMS. Remember, this the ’90s, it was a Microsoft world, and ecommerce platforms were rudimentary at best.

I knew my shit about what I worked on daily, but I was not a CS major. I was an English and Religious Studies major. I taught myself HTML and JavaScript and realized there were way more opportunities working in web development, than trying to be a writer, or whatever the hell else (barista, bartender, etc.) you’d do with those degrees. We had about millions in funding at the time this event occurred, and very smart people running our company. We had outgrown our space, and the developers had all been moved to this remote “camp” to crank out a few major releases (pre-agile world) of the site.

One day, all the higher-ups came by to see how things were going and get a rundown on the latest and greatest features we were building. I knew most of these people well; including the founders. I’d been employee number 9 or something, and we were up to 60 or 70 people by then. So it was a different world, but I’d interviewed with and gotten to know the founders from day one. There were some other VP level folks in the room that I didn’t know well, but for the most part I wasn’t too intimidated by the crowd. Outside of the fact that they were very smart 30-somethings and I was 1 year out of college and didn’t know anything about the business world. My CIO was an old-school Valley veteran. He hired me, and I respected the shit out of him, but he was not my direct report any more, and I didn’t talk to him all that much.

So, I can’t remember exactly how things kicked off, but the meeting started, and apparently we were going to start from 35,000 feet. I expected to mostly be sitting on my ass and listening during this meeting. Maybe asking or answering a simple question; at the least. As things got going, someone suggested we loosely diagram out our architecture on the whiteboard; how data moved between systems, what layers were in place etc. My CIO looked at me and said, “Adam, why don’t you do it.” I was astonished, horrified, and angry. But little time to think about emotions, as all of these people stared at me. I went up to the whiteboard. I rarely used whiteboards. They didn’t have them in college; they still had blackboards – for the professors to write on. I had scribbled on them here-and-there in the year I’d been working, but not extensively. I suck at drawing objects; I mean I am horrible at even drawing a cube. I had never ever done any kind of systems diagramming. I barely knew that databasess were represented with “buckets” or whatever those silos are referred to. On top of all this, I really didn’t have the greatest understanding of how data moved between our fulfillment, financial reporting, and other fringe systems. They had very little to do with the code I wrote every day.

It was a disaster. I had no idea where to start. I fumbled my words and drew some “things” on the board. The room immediately knew they were watching a train wreck. I can’t remember how I was freed from the situation; I think I only suffered up there for about 2 minutes. I’m sure it felt like an eternity, and I felt like an idiot as I returned to my seat.

As I’ve found with life at SwellPath, there is a fine line between empowerment and embarrassment. Empowerment can accomplish a lot of things; it builds confidence in the empowered, and it means that YOU (or someone else) are not handling a situation or decision that you normally would be. You’re taking some responsibility off yourself – a critical component of evolution of your role as a founder. So opportunities to empower are a win for you, and for your employee. Handing off responsibility to someone who is not ready for it, is a loss for both of you. The employee fails, feels horrible, hates you, and (at least momentarily) hates their job. You get poor output; whoever is on the receiving end thinks you or your company suck. At least some of those people watching me fumble around up at that whiteboard probably thought I was a moron, and my CIO or manager was doing a horrible job of getting the team on the same page, and hiring morons. The ones who knew me better probably just thought the CIO had made a bad decision asking a junior level front-end guy to diagram a relatively complicated system architecture.

When you make the call to empower your employee, and hand off something to them. Make sure they know how to do about 80% of what you are handing off. Less if they are a good bullshitter/charismatic person; higher percentage if they shake in their boots when you ask them how their weekend was.

There is a difference between “baptism by fire” and being “thrown to the wolfes.” Empowerment and the hand off of responsibility is absolutely critical to growing an organization. Taking ownership, understanding peoples’ levels of understanding, and giving people time to prepare for more responsibility are also critical. Throw your employee to the wolves because you think it’s a good idea, or your not prepared yourself, or you don’t want to handle something yourself – and you’ll only stagnate them, if not set them back. They’ll never forget being thrown to the wolves – even if they don’t think of it much, it’s something they might randomly be reminded of 12 years down the road.

One final thing, and there is irony and clarity in this last bit. Sometime in that general time-period, we went to a user conference for our CMS. The CIO was speaking. This was the only time I saw him speak to a large group of people not in our company. He performed one of the most epic public-speaking fails I have ever witnessed. Froze completely, had to have someone come up and salvage the talk. It was mind-blowing. Now I speak regularly in front of large groups. I fuck up six ways to Sunday, but I never fail. I always know what I’m going to cover, and it’s always something I have a solid understanding of (or am an “expert” on). I probably would have knocked that systems diagramming out of the park if I’d had an hour or so to prepare for it.