Fears of a Startup CEO


I have not been writing much on Jeffsauer.com, but that doesn’t mean I haven’t been writing. In fact, you can see my newly written words often on the web at the various websites I have been working on recently. You surely know about Jeffsetter and Jeffalytics, my two other narcissistically fueled “Jeff” websites, but I’m also trying to build an amazing travel community at Free World and I’ve recently started to share everything in my brain about marketing at Knowledge Land. Add to that several other sites that I have worked on in the past and I’ve been staying busy.

The last two endeavors are the startup ideas I have been working on since going back on my own at the end of last year. They are what excites me for the future and keeps me occupied in the present. They are my attempt to build something substantial and add value to the world. They are my passion projects, and they are how I am chasing the dream.

I’m writing today because I just read an article that hit very close to home on Pando Daily, where a startup CEO talks about their fears. Holy shit! This is such an accurate depiction of the fears that go through my head every day as I work toward building a long lasting company around my passion.

I highly encourage you to read the full article, where 44 fears are listed. They are realistic fears and I have thought at least 80% of them over the past 4 months as I work on my startups. For the purposes of this post, I just wanted to share the first 10 fears expressed by this CEO:

Fears of an NYC Startup CEO

Keep in mind that there is a good chance that this is a successful company! The reality is that no matter how successful a company becomes, it’s the duty of the CEO to worry about creating a great company that will satisfy employees, investors and the marketplace for years to come. Heavy is the head of the CEO for any company, even if they are the only employee.

Every single day I’m faced with doubt about whether I am doing the right thing by taking the entrepreneurial plunge, and every day I keep on plugging away because I can’t imagine myself doing anything else. It’s easy to get tempted by the “easy” money of taking a well paying job as a VP of Marketing or taking on consulting gigs to pay the bills. But each minute spent on those projects is a minute that is not spent accomplishing my dreams.

I admit it, I’m afraid. At times I’m scared shitless. And that’s what keeps me going.

Opening Photo Credit: alles-schlumpf via Compfight cc

Presentation Block or Writing a Business Plan

You’ve surely heard of writers block, but that isn’t my problem right now. The words have been flying out of my fingers for the past week, and I show no signs of slowing down.

Right now I am having a different kind of block that is causing me to feel guilt, and that is what I am going to call Presentation Block.

Technically, it’s really business plan block, but that is too many syllables to continually write. As some of you know, Three Deep has launched a product called Crossfuse, and I am leading the team to develop this product and set us up for the future.

After good press from Tech.MN announcing that we have secured $750k in funding for the project, and a fantastic writeup by the Minneapolis Star Tribune, we have started to see momentum around Crossfuse.

In fact, we have seen enough momentum and we know that our target market is so strong, that we are looking into receiving additional funding to develop out Crossfuse FASTER. You see, up until recently, Crossfuse was a “bootstrapped” project, meaning that we used our own money and client payments to fund development. While this is a great way to get started, it also provides its own limitations – and that is you can only provide resources to the project that generate revenue immediately – so you are never getting ahead of the curve when it comes to development.

Here’s where presentation block comes in. In order to secure funding to the magnitude we need, we must first come up with a business plan and a “pitch” deck to get investors interested. For me, this should be easy, because I have had this business plan in my head for the past 5 years. I know that it can be done, and I know that the market needing Crossfuse is HUGE (about half of the Fortune 500 could use our platform for immediate impact). I am just having trouble putting it into writing.

This is supposed to be the easiest deck I’ve ever done

I know why I am having the problem, too. I’ve known it all along, but I don’t have a clear solution. I figure maybe writing about them will solve the problem?

  1. I’m afraid of being wrong. I have never written a business plan and I fear that what I write will be utterly preposterous to investors. What if people laugh at the stupid idea? What if it’s not a good idea at all?
  2. I’m afraid of the change. What if we do succeed? What does that mean for the company? What does it mean for me?

When I write it down it sounds stupid. There is no way that this is wrong – Crossfuse is something corporate marketers have lusted after for the past 20 years (they just haven’t seen it in a completed package yet). In addition, I have never been afraid of change before, and have structured my personal life and career to embrace change in every scenario. I love change, so why worry here?

Maybe this is all I need to finally get over the hump. If that’s truly all that was getting in the way, then there is nothing to fear.

I am going to try not let perfect get in the way of “good enough” on this deck, and submit a rough draft this week.

In the meantime, I am going to use the pitch deck from Mint.com as my inspiration moving forward. These guys clearly had their shit together!