It’s been one year since I left my job to pursue life as a full-time entrepreneur.  It’s been a wild ride so far and the journey is really only just beginning.  I’ve been spending time recently reflecting on the past year, what has gone right and what has gone wrong, and thought what better than to post some of these reflections on Built in Chicago.

A little over a year ago I was leading business development for a startup in San Francisco (see this blog I wrote last year on my thoughts of West Coast vs. Chicago startups).  Prior to that, I spent five years in a corporate job and was the co-founder of a corporate spin-off where I ran global operations.  Both of these positions gave me the discipline, leadership skills and knowledge to run my own company, but what they didn’t prepare me for was the emotional aspect.  A while ago, someone told me something that has stuck in my head ever since - that in a startup the highs are very high and you can feel on top of the world, but the lows are very low and sometimes make you want to give up in frustration.  There is rarely a middle emotional ground in building a startup.  A year in now, this couldn’t be more true.

Recently, Ethan Austin tweeted “The hardest part about running a startup, isn’t running the startup.  It’s having the courage to take the leap in the first place.”  I would second this advice for anyone who is still working a regular job, but thinks day and night about starting their own business.  Just take the leap.  Last June I left my full-time job, got married, went on my honeymoon to Italy and came home the first week in July, unemployed, and ready to start my company (thanks to my understanding and loving wife). 

My company, Ideavation, develops technology solutions for the wine and beverage industry.  Our flagship product is Uncorkd, a software-as-a-service platform for restaurants to create and manage interactive menus on iPads.  Our product helps restaurants increase their wine sales by 20%, allows them to update their inventory in real-time, reduce printing, and best of all, improves the customer experience by helping diners feel more comfortable and confident ordering wine.  I started the company after seeing celebrity chefs moving towards iPad menus and reporting great results, but spending tens of thousands of dollars in development.  I didn’t invent iPad menus, but I made them better, easier and more affordable.  Since last July, we’ve come a long way – we now have seven full and part-time employees, have our software being used in restaurants across North America (by chains such as Ruby Tuesday, hotels such as the Four Seasons, casinos such as Tropicana and country clubs such as Congressional), and are finalizing large distribution deals.  We were also honored to be a finalist for the Moxie Awards (hey Code Academy – couldn’t you have just settled for two awards and let us win one?).  Here are some of the key lessons I’ve learned over the past year:

1.       As I’ve already mentioned, the hardest part of running your own company is the emotional aspect.  One day you win a big key account and feel amazing only to wake up in the morning and see your competitor did something even better.  What I’ve learned is that you can't let your emotions of the moment cloud your thinking and stray from a long-term focus.  You need to share your thoughts and feelings with those around you – not only your family and friends, but also your employees and co-workers.  Which leads me to #2…

2.       Make sure the people you work with are as engaged and committed as you are (or close to it).  As a sole founder, I think it would have been easy to treat everyone as if they were just employees, but we wouldn’t be nearly as successful.  I want my teammates to feel pride and ownership of the company.  It’s not about how many stock options they have, it’s about how you talk and behave and engage your co-workers in the company.  It’s about the culture you build.  We are all successful together; the company is my baby as much as it is theirs.

3.       You must break out of your comfort zone.  It is hard, very hard, but you must do it.  For me, cold calling brings instant butterflies to my stomach.  One year ago, I could never get myself to pick up the phone and pitch a prospect on our product.  Even today, I still get squeamish, but I can at least pick up the phone and do it now.  It gets easier every day by practicing and knowing that the product I am selling them will actually deliver value.

4.       Surround yourself in good company and don’t be afraid to ask questions.  I started working from home last year before having the wonderful opportunity to work alongside the great folks at Sandbox Industries.  It was great to be in a place with so many passionate people willing to help each other.  More recently we moved to 1871 which has also been amazing.  Just being in the community doesn’t do it though, you have to be willing to ask for help when you need it.  The great thing about Chicago is that there are so many awesome communities and so many people willing to go out of their way to help.

5.       You need to be a showman, a promoter, and a great storyteller.  This is probably the area where I can still improve the most.  I’m pretty humble about our company and the progress we’ve made, but what I’ve learned is that if you don’t show excitement and passion about your startup, then no one else will either.  That doesn’t mean being arrogant, but showing your love for what you are doing is different than bragging about your success.

I hope these five lessons will be helpful to those just getting started in their endeavors.  If you’re one of the thousands of people just getting started, dive right in and don’t look back.

As for me, I’m even more excited for year two and what’s to come.  We’re now raising a seed round (follow us on AngelList), experiencing fantastic growth, have a great team and awesome product roadmap.  I’m super excited about the Chicago community and the great things happening here.