My Accelerated Path to Entrepreneurship

On January 1, 2015 I knew it was time to get serious about becoming an entrepreneur. Running my own business full-time has always been a dream of mine, and it seemed like ‘now’ was as good a time as any to get started. Seven months later, I am one week away from my last day of regular employment and my first day of working for myself full-time. This is how I did it:

1. I made a written plan, and stuck to it.

My wife, Whitney, deserves all the credit for this one. Somehow after five years of marriage and seven years of living together, I never realized how masterful of a planner she was. When it occurred to her I was serious about starting my business (and that my planning skills needed a big boost), she sat down with me for several hours and helped me understand how to properly list, prioritize, and organize my plan effectively.

My biggest issue at the time was the same issue most of us have – too much to do, too little time. Not to mention I had several ‘side projects’ and part-time distractions taking me away from my primary goals. Whitney helped me get focused on the truly important things, the things that would “move the needle.” Most critically, she taught me how to estimate how long individual tasks would take, then schedule blocks of work time based on my availability on a week-to-week basis.

It was an eye opener to realize how little free time I had. Especially since much of that free time was already reserved for family engagements, chores, grocery shopping, laundry, and a second job doing part-time consulting work (on top of my full-time sales job). Therein was the power of this exercise, though. It enabled me to identify and capitalize on the few blocks of time I did have available, which would not have been possible without seeing it on paper (or in my case, on Google Calendar and Asana).

2. I saved enough money to cover my living expenses for a year.

There probably wouldn’t be anything more anticlimactic than quitting your job and setting off on your own, only to realize you’re about to run out of money in a few months before you reach revenue. This is why I saved as much as possible once I knew I was “jumping off the cliff” to become an entrepreneur. Fortunately we’d already been saving for quite some time, and I only had a little ways to go before hitting my savings target.

We also tightened up our budget. Grocery and food-out expenses were minimized, I quit drinking alcohol (mostly), and made other financial sacrifices in order to save for my dream. Things that were categorized as ‘necessities’ one day turned into ‘wants’ the next. To my surprise, many of these things ceased to provoke any desire at all as I adjusted to my reduced standard of living – perfect.

3. I created a detailed Year 1 personal cash flow projection and budget.

In addition to saving money and reducing expenses, I created a detailed personal cash flow projection for my first year as an entrepreneur (feel free to grab a copy of the template I used, which I obtained from my business partner). This helped my wife and I get on the same page with our expected expenses.

We also started using a free app called GoodBudget, which made it easy for us to track our expenses every time we made a purchase. By simply opening the app on our smartphone, typing in the amount of a purchase, and categorizing it, we suddenly had a full-scale view of our monthly and yearly expenses. This was the only workable method for us, because the idea of saving receipts and punching in the data later just wasn’t in the cards.

Importantly, both the cash flow projection worksheet and GoodBudget allowed us to plan for ‘irregular’ expenses (ones that don’t occur monthly), and visually see them and track them in a simple way. This one thing was always a hangup of mine with other budgeting systems and methods in the past, so it felt good to finally get on top of this part of my life.

4. I created a dynamic and detailed business plan.

This is a prerequisite when starting any new business. What I found was the plan itself wasn’t as valuable as the simple exercise of thinking it all through. Business planning and forecasting forces you to think about expenses, processes, competition, and project management. It injects some healthy fear into the equation while also getting your gears turning in regards to how things will actually get done.

Notably, the business plan was a living, breathing thing. Weekly meetings were conducted with my business partner so we could strategize. Emails and phone calls were exchanged with our primary supplier and support company, to ensure the logistics were hammered out and that a solid relationship was in place prior to opening our doors. Financial forecasts and cash flow projections were constructed. Operating agreements were signed, and business registration paperwork was filed with the Secretary of State. Communications networks and key software were installed to ensure we could hit the ground running.

While the outcome of our venture is still uncertain (small business statistics suggest we have a 1/3 chance of success), I embark on this journey with great confidence given our careful planning and preparation.

5. I secured an amazing support network of family, friends, colleagues, and mentors.

It is well-known that new entrepreneurs work very hard and have a healthy dose of stress to manage. Not to mention it can be hard to see things clearly sometimes without a little perspective from an outsider. This is why I’m so grateful that my wife, my parents, several friends, and even my current boss (and my former one!) are so supportive of this venture. My business partner, Thomas, is a huge source of inspiration and support as well.

In the absence of a staff, I’ve gotten help from my support network in many ways – from providing emotional support and encouragement to reviewing legal documents and doing research. One of my personal mentors, James Adamy of Ju-mp, has provided strategic advice and user feedback alike, having gone through our consultation process as an end-user. Another friend, mentor, and consultant – Jordan Arbuckle of the CNQR Academy and SmartInbound – has provided similar advice and feedback, for which I’m very grateful.

Bottom line, I’m not sure where I’d be without the support of these key individuals. Altogether there are 7-10 of them who I’ve leaned on these past seven months, all of whom have supported my mission and done everything possible to keep me on track. Should you be aiming to start your own business, I’d highly recommend keeping an active dialogue with a close, diverse, and trusted support group like this.


Walking away from my full-time sales job and becoming an entrepreneur wasn’t easy. Getting all the pieces in place, though, was easier than I originally thought. By doing intelligent planning and practicing self-discipline, it came together much sooner than I expected. For more information or questions, please feel free to contact me – I’d love to help you in any way I can.

Share This Article: