Some say you don’t become an entrepreneur - you’re born an entrepreneur, but I certainly didn’t start my career as one. After a dozen years climbing the monkey bars of large organizations, I traded my corporate attire for an irregular paycheck, uncertainty, doubt and worry. This week I was asked to speak to a class of students on my journey in starting a new business and so I sat back and thought about the steps that I took that brought me here.
Step One: Get bored. Or get Crushed.
Either way - get creative. Back when I worked in technology management (my first career), after a while my job became a well oiled “system”, leaving me with plenty of after-work time to think about other stuff. I was bored. Fast forward 10 years and I was in career number two. Working for a large law firm resulted in the opposite problem - getting crushed with work left me with no free time, and that was stifling to my creativity. In both cases, I started to gravitate to the creative and people-aspects of my job - idea generation, sales, negotiating, pitching new business.
I started to ask myself (and annoyingly and persistently asked my work friends) if I was more suited to doing something else - something non-traditional. But I had already declared to the world that I was a people manager, and then a lawyer - so to take a left turn into the unknown world of startup was worrisome, and filled me with a lot of existential and personal credibility questions.
Step Two: Sniff around for Inspiration.
No boss + no rules = no paycheque, which is why it’s daunting to jump into entrepreneurship when working for someone else is all that you know. As an outsider looking in at the dot com people (in my early technology days), it all looked so sexy. I attended tech events to learn as much as I could, and even volunteered in the late nineties for the dot com boom Toronto tech education event company Spadina Bus.
When I returned to school for my MBA I hung out with the former entrepreneurs (soon to be serial entrepreneurs) who were in my class. I continued to volunteer, co-running the MBA student organization Entrepreneurs@Ivey. This gave me a chance to meet more folks who were “out there”, “trying things”. I think I was still fearful about making the jump but it was starting to become more “accessible”.
Step Three: Get Impatient and Start Small
The initial idea for Clausehound formed months - maybe a year - before I launched. Tired of waiting for our first version of Clausehound to go live as a result of software development delays, I scrapped our initial version, rolled up my sleeves, and pushed version 1.0 of Clausehound to the web by myself: It was far from perfect, but six months later we saw 400% increase in web traffic from month one and I knew I was on to something. This was an early lesson for me: to get impatient, get over the fear of looking silly, and to just get started.
Step Four: Save money
Diving into my venture was a hard decision, but doing so without money in the bank would have been impossible. I needed a “runway” - the ability to survive without making any money. For many people that runway can come from savings, friends and family, a co-founder who continues working at their job while you’re out building and hustling, or possibly an investor (although in my experience investors typically arrive after you’ve proven out some early elements of your business launch). I started my venture with a tight personal and work budget that gave me a runway of 3 years before bankruptcy. Of course that changed really quickly once I started hiring my team.
Step Five: Don’t Give Up (and Get Really Lucky).
Once you get started, It’s easy to fail, and running out of money is certainly a roadblock to success.
“Sticking with it” - a stubborn, sometimes foolish determination to not fail, is harder than it sounds, but if it’s one of your qualities then buckle up and get ready - starting a business will throw you into a world of uncertainty. I’ve had a few brushes with entrepreneur non-existence and have bounced back more than once as a result of finding a customer in a moment of need, which has a lot to do with good karma and staying positive and optimistic (a.k.a getting really lucky).
Step Six: Build a support structure.
You answer to nobody as an entrepreneur - and in most cases that’s not going to work for you. From school days, aren’t we’re all used to receiving assignments, meeting deadlines, and getting measured? Remove that structure and you might find that the lack of accountability will turn an activity that should take a week into a month long saga (can any PHD thesis writers out there relate to this?).
Early on I organized a board to whom I had outside accountability. When I had zero clients they held me to task on my go-to-market strategy. We held monthly board meetings and I took very seriously the presentation of my business plan and board updates. This was a somewhat artificial reporting structure as it was self-created, but it was important and worthwhile to keep the business on track. A support structure can also be friends, spouses, anyone who can give you perspective on your ideas and the way that you present them. I’m still getting by with a lot of help from my friends: this month I called a friend and walked him through my investor pitch on a one hour call and was thankful for the feedback.
Step Seven: Believe in the value that you’re creating.
Building a new product in the highly competitive market of legal services in North America would be impossible without a commitment to value creation. The first version of Clausehound went live exactly four years ago this past Friday. Four years later our 4.0 version has just been “committed to live”.
Getting here took a lot of faith, and for many months the “fuel” was hearing positive feedback from entrepreneurs or lawyers who told us in passing that they had bookmarked our site. Persistence in creating value has led us to customers, and continued persistence has led us to customer referrals. It wasn’t easy become an entrepreneur and still isn’t.
My pathway to entrepreneurship can be traced to a series of steps (and missteps), a few of which I have listed here, and many more to come I’m sure.