I Started My Business Ten Years Ago

In 2006 I got laid off, performed the “worst job search in the history of job seeking,” and decided to start my own business. Well, I really wanted to get my next dream job and work my way up the ladder again, but I didn’t have that option, and so Plan B was to just go out on my own.

I had a superb idea: create a website to help job seekers organize and manage their job search, just like a CRM system helps salespeople stay organized and not miss follow-up opportunities.

I figured that, within three months, I’d be on track to buy islands and jets. You see, timing is everything, and at the time, anything internet and social was hot. I was sure I was on to something big.

I was, but here we are, ten years later, and I’m buying nether islands nor jets. That’s okay. I’ve matured a lot in the last ten years, as has my company (JibberJobber.com). We still help people manage and organize their job search… that is the core of our offering. But the road to get here has not been linear. As an entrepreneur, I’ve been able to dabble in this, try a little of that, and spend a lot of time on some other things. Some would be distractions and failures, others would add significant value to my company.

Here are some of the lessons I’ve learned over the last ten years. I hope this helps you, whether you think you want to be an entrepreneur, or you’ve been “trying” to be an entrepreneur for a few years.

Use your own metrics to measure success.

If you pay attention to the Silicon Valley mindset, success seems to be measured in getting funding and some very quick metrics, like getting a gazillion what-they-call-users.

Getting funding means (a) you have cash in the bank, and (b) the company and decisions are no longer yours. The very quick metrics can be fatally misleading. Getting a “user” doesn’t mean you have someone that uses your system, nor does it mean you will get any money out of it. Not that money is everything, but it helps you pay the bills and keep your company open.

I used to measure number of signups per day. One day I switched to measuring number of upgrades per day. Today I measure a certain type of upgrades per month, and when my next “offering” (that is an MBA word to mean either product or service) comes out, I’ll be monitoring a specific metric related to that very closely.

I’m not saying things other smarty-pants business people say to measure is worthless… indeed, knowing how many people sign up and comparing that to how many people upgrade (or, log in X times, or other metrics) is helpful, you have to figure out what the most meaningful metrics are to you, based on your goals. Is it to get more exposure and signups, or to get more cash in your account? Those are two different goals, and you should monitor different numbers to see how you are working towards your goal.

Evolution is inevitable.

When I first started JibberJobber, I thought my entire world would focus around the web app (mobile apps weren’t really a big deal in 2006). I couldn’t see doing anything else until JibberJobber was “successful” enough that I could step away.

However, from September to the end of December, in 2006, my revenue was $400. I didn’t need to be a math major to know that earning $400 in 1/3 of a year was not good for business. Remember, I thought my success would be overflowing within three months of starting. $400 isn’t overflowing.

In addition to not seeing financial success, I started running out of things to do. My development team was heads-down busy with their projects, and me asking for the umpteenth time “how are things going? Are you almost done?” was only distracting them and slowing down their progress. I had written articles and blog posts for every outlet I could think of, and needed to throttle my marketing a bit. So I had (a) time on my hands, and (b) a need for money since my master plan of having my users upgrade wasn’t working out as well as I had hoped.

Long story short, I wrote a book. Fortunately, I wrote “The Book” on LinkedIn. It was the second-ever published book on LinkedIn. This was a time when LinkedIn didn’t have customer support, and their help center was “lacking.” The timing and topic couldn’t have been better. Here’s the interesting thing: writing a book meant that I would soon start speaking for money (which is what I call “professional speaking”).

You can imagine that writing a book and travelling the U.S. to speak took time away from JibberJobber. But, it took care of the (a) time on my hands, and (b) need for money. So my schedule and focus evolved, and I spent more time on the speaking, and even put out two more books.

Later, I started doing courses for Pluralsight. This was a four-year adventure for me, and in those four years I produced thirty courses to their high standards. Of course, I still worked on JibberJobber, and still managed my team and the direction of the product, but it was an evolution in my business plan that I didn’t foresee at all.

The next twist in JibberJobber’s evolution will take what I’ve learned over the last ten years and really enhance the job seeker’s experience. It is going to be awesome, and I’m as excited about this as I was when I first started JibberJobber.

If you think you’ll start something and you have a long-term linear path to “success,” realize that you are going to be tempted with good and fruitful distractions along the way. You’ll either have to figure out how they will fit into your long-term journey, how they complement your core offering, or how you’ll say NO to a lot of seemingly great opportunities.

There’s a time to learn, and there’s a time to DO.

I have this memory of watching Shark Tank and Marc Cuban made a comment that you sell all day long… when your company is open for business. If you want to do other stuff… back office stuff, sharpen your saw, read articles, etc., then you do that after hours.

The point is, don’t take prime time to “book learn.” I’m not against learning, but if you are open for business, then run your business! The most important thing you can do is to get a clear path that you can get on as soon as possible to generate revenue.

Be careful comparing your company to others.

I compared my company to Facebook, LinkedIn, Twitter, and others. The problem is that my company was nothing like those. I didn’t have the funding, or the staff, or the connections, or the development and marketing teams, etc. that those companies had. I started with a “bootstrap” mentality and they started with the resources in place to take them to multi-billion dollar valuations very quickly.

If you compare your business to others, you’ll sometimes be delighted (“ooh, we did this better than they did!”) and many times be disappointed (“why did they get news coverage for something so lame, and we still haven’t gotten any news coverage??”). Comparing your company is about as mentally healthy as comparing yourself to others. It’s just not a good idea.

Know what your vision is, and work towards that vision. Focus on creating and adding value to your customers, not on what your competition is doing that you could copy.

It’s okay to be uncomfortable.

The most uncomfortable thing I’ve had to do is make cold calls. It’s not my favorite thing to do… and it gives me a fair amount of anxiety.

Of course I know that you shouldn’t make cold calls… you should always get an introduction. But sometimes that has just been impossible to do, and so I’ve had to brace myself to do the uncomfortable.

Eventually, I got to the point where it wasn’t so frightening. I found that I normally go to voice mail anyway, and I leave a nice, short message. And I usually follow-up a few times, and then move on. And that is okay. It’s better than being paralyzed with fear of rejection (or fear of whatever I was afraid of) and knowing that I chickened out.

Look, to get to that next level of success requires you to be somewhat uncomfortable. Students are uncomfortable before exams, job seekers are uncomfortable as they ask their network for help, and CEOs are uncomfortable when they have to get up in front of a group of people and tell them their jobs are ending. Don’t think that just because someone makes something look easy that their aren’t a bunch of butterflies in their stomach creating havoc.

I’ve learned a lot more over the last ten years.

Those are just a few lessons. I thought that I’d write this post after having sold my company, and that I’d be respected as an internet success, but I no longer have the patience to wait that long. I hope that this helps you get a reality check on being an entrepreneur.