The Path of Preparation for a Start-Up

This article was originally published on Medium.com

Today I’m starting a new chapter, and my latest venture. I’ve been preparing for the last 3 years and I’m as ready as I can be.

When I stepped down from the last business I started, I knew immediately that I wanted to do it again. Despite the ups and downs, sleepless nights, intense mental and physical stress, financial strain, disappointment and heartbreak, I wanted to start again from the beginning. Only this time, I took years to prepare.

I have a few startup “losses” under my belt at this point. With each attempt comes extreme learning, and with each loss comes intense reflection. With my last company, I became acutely aware of what I would need to change for the next time I took the leap.

The following is a checklist I created to set myself up for success in a path of uncertainty, and where I’ve focused my time and energy for the last 3 years. Hopefully this will help those of you who need inspiration in strategizing the next big change in your life:

THE LIST

Clear My Head

I’d lived in or around Boston for 14 years and after departing from the business I’d built, I was exhausted and needed to clear my head in a new environment. With my fiancé on-board, we sold our house, put everything in storage and hit the road to move to the Florida Keys (with a pit stop in Alabama to get married along the way). While I had a full-time job, living in paradise gave me the opportunity to focus on family and other “meditative” activities like kiteboarding and spearfishing. It was important that I change my physical, mental and emotional state to focus on becoming a stronger leader next time around. The Keys helped with this.

Learn From My Mistakes

We all make mistakes, but the ones I had made in business had lead to a very unfavorable outcome, and it’s hard not to dwell on that. It took some time to convert the “mistakes” to “lessons” in my head but it was critical that I do this in order to move forward with a clear mind.

More Experience

Once mistakes become lessons, you can really start digging into the details. I knew there were areas I needed to improve from things as simple as better task management, to learning how to scale a company, to becoming a better leader. I was fortunate enough to be hired by one of the most premier digital agencies, Acceleration Partners, where I had the opportunity to work with talented team members, prominent start-ups as clients. I worked with client after client to craft scalable digital strategies, giving me the freedom to test growth hypothesis and the visibility to know what worked and what didn’t. It was like a fast-track MBA in growth marketing for various verticals.

More Focus

I’m scattered. My mind races and my focus is pulled from one thing to another with each new Slack notification. It’s important that I improved in this area, and so I resorted to guided meditation through the Headspace app. At first I think maybe I was expecting some sort of tangible result (focus-superpower), but I was not able to reach a noticeable difference for five months or so. I have a long way to go, but I do find myself less distracted at times, and am thankful to have started the practice.

More Energy/Less Stress

I remember all too well the exhaustion, headaches, back-pains, indigestion and anything else that comes with the package of starting a company. This time around, I knew it would be critical to put my health first. I started working with a nutritionist and working out fairly regularly in order to be in better physical shape. The increase in energy so far makes me feel like I’ll be able to handle and accomplish much more.

Less Financial Burden

Money weighs on me. I live pretty conservatively, but the weight consumes me when my savings account starts going in the wrong direction (as it typically does when starting a company). I knew that this time around, I could not have that be a distraction for me, and so (with the blessing of my wife) we once again sold our house in the Florida Keys, and moved close to the in-laws where the cost of living is extremely low. The proximity to her parents would also be helpful in what is likely to be a hectic travel period in my life very soon.

More Time

Much of the above list requires a time commitment. As a new dad, time is a resource that is becoming increasingly scarce. Enter, “The Morning Routine”. The only way to fit all of my new habits (meditation, exercise, reading), full-time job, and work on my start-up is to sleep less and work more efficiently. I wake up very early now even on weekends, and start a regimented morning routine to get the most out of each day. Painful at first, but well worth it.

I’ve completely redesigned my life around what I believe it will take to succeed with this new venture. I’ve always been goal oriented, but have struggled at times to build the strategy and milestones needed to reach that goal. As I get older, I know now that planning the journey is critical in obtaining any major accomplishment in life. This preparation is just one example of that, which I’m confident will pay off.

If you’re interested, check out Pillow.io to see what I’m building.

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