Startup – Page 5 – Maybe I'm crazy

Step away from the micro and think about the macro

As a designer, developer, and an entrepreneur, I am a detail-oriented, perfectionist. I obsess over the details of every design, line of code, or product. It is almost like I have an itch that I have to itch and if I don’t then it just bothers me beyond belief. This “perfect” vision that I have in my head drives me to keep pushing until I can accomplish it. By staying up all night or not shipping a product till every feature is working, I work till the last minute. With all this said, I still manage to stay level headed and focused on putting the pieces together, but it can be challenging.

Over the past few days, I have been faced with this challenge. Next week, I have a big investor pitch presentation and I have been reviewing each slide and its content for “perfection.” Additionally, not only have I been reviewing the deck I have had an investor also review it with me. He sees things differently than I do (as expected) and therefore picks and prods at certain elements. This has been challenging because I have already picked it apart myself to the last degree, then to have him do it again is quite frustrating. As with many presentations, its good to have a second eye and in this case is self inflicted as I asked him to help, but it is making me go crazy.

A day in the life

Startup

As I have made this transition, the question I continuously get from friends, family and prospective entrepreneurs is what is your day like. Before leaving my job I had this understanding that it was going to be busy and stressful but couldn’t really put it into words beyond that because I frankly just didn’t know. My girlfriend thought about it logically if you were working 80 hour weeks with 2 jobs then when you just work careband you will have more time to hang out. The reality is that’s not the case.

Just this morning as I am writing this, I looked at my calendar and I have 3 back to back meetings this morning and one more in the afternoon. What comes with this is the question, how do you ever get work done. And that question is a tough one. When looking at the to do list there are a hundred things to do, things that require my time, attention and focus, not just delegating to others. My strategy so far has been to bring my computer and a notepad with me everywhere I go and use my time between meetings and events wisely. With this I mean, working on the train, the bus, at local coffee shops for spurts of time 15 30 min. I have cut out the occasional social media browse or news article browse when I have a few extra down minutes. The other area of time is at night after the “work day”. I usually spend that time working and doing the things I need to do to move the company forward.

Take time for yourself

Startup

I had a great week, not just because I am starting to feel situated but because I took a trip to Denver, CO. One of the things I had told myself before I joined my company full time was that I was going to take me the trip as soon as I left my previous job. Unfortunately, I couldn’t get the details situated fast enough so had to do it this past week instead. I had decided to take a trip to Denver, CO to climb some mountains and clear my head. Also, a good friend of mine whom I started my first company with in college lives out there, which gave me a chance to spend some time with him and a free place to stay. My goal in going to Denver was to take a break. To help me close the chapter of my past job and start the new chapter of this journey of my company. I was hoping I could just get away from the city and surround myself in nature in order to refocus and energize myself for the coming year.

On the plane to Denver, I was fortunate to sit in the middle seat on a Southwest flight. Many people would dread sitting in the middle seat, but I love to sit there. I also am different than most as I love to talk to the people around me. It is a game to me to see how long it takes me to get my neighbor to open up and tell me their story. It is also an opportunity for me to be who ever I want to be. Because the chances are you will never see that person again, you have this rare chance to live your dream or make up a few details in your current life. (I once convinced someone that I worked for google, because I was flying from San Fran to Chicago wearing a google shirt. That was a fun conversation. I can talk about this weird interest of mine for hours, and may in another post.) On this occasion though, I didn’t fill in any details and just told my story. Most of the time though I end up just listening and asking questions to learn about their stories as I did this time with Ruth.

Getting Organized

Startup

In an effort to transition smoothly from my fulltime job to working for myself (my company), my advisor suggested reading The First 90 Days. The First 90 Days is a book for people (mainly executives) transitioning into new leadership positions to help them quickly and efficiently “prove their worth” to a company. Although, a little different for my situation I hope to take the techniques and strategies and apply them to my role as CEO of my company. One of the first chapters talks about how each month of your plan should have a specific goal or outcome. For me, I have made month 1 (August) all about getting organized. Without a clear roadmap or known framework of getting organized, I set out to create my own roadmap. Ironically, the timing is similar to how freshmen in college start their university experiences in August. I hope to apply similar steps as I did when I was a freshman in terms of meeting people, getting into a routine, completing homework on time, and many other important areas.

I cannot decide between two women

Startup

People constantly ask, usually with a bit of shock, how I could possibly do such a thing. A nice, trustworthy, honest guy, sneaking around, splitting my time between not one, but two women, and keeping it up for more than a year! My short answer is that I love each one for different reasons and I see a future with both – their interests and passions directly line up with mine. When I am spending time with each one, I feel empowered and confident enough to accomplish anything. I know that I will have to choose at some point. I’ll have to make up my mind and go full force with one while leaving the other behind. The conversation will be difficult; to discuss all we’ve been through and why I have to move forward with my other love… and if it’s even possible, to break up on good terms.