Recently, I’ve seen a deluge of posts on HackerNews that detailed candid accounts entrepreneurial pursuits that didn’t end the way they originally intended.  I’ve read posts that detail it takes several at-bats before you connect or 3 years to get traction.  I only lasted a little over a year.  Well, it’s my turn to add to that list.

If you’re reading this, you’re probably thinking of starting a new company or had your “entrepreneur cherry popped” and in the thick of running your startup - which are both awesome exciting positions to be in.

The point of this post is not to deter you from attempting to build an awesome company, change the world or making oodles of money from the process, rather it’s to inform of the consequences I’ve realized only after the fact I had to throw in the towel for my startup Date Ideas.

While running Date Ideas I learned the hard way that your greatest enemies are delusion, ego, your relationships and your runway as well as having a rock solid team.

Delusion

For a while, I was delusional.  I mean, a small amount of delusion is okay.  As an entrepreneur, you’re going knowing the odds are already stacked against you.  Despite that, you’re creating something out of nothing, turning vision into reality and seeing an opportunity and capitalizing on it.

The problems begin when you don’t hit milestones.  When things start to slide and excuses stop popping up over and over again.  The feeling of dread and embarrassment overtakes you when someone asks you “when are you going to launch?” and you’re left sidestepping and making up some lame excuse to cover up you weren’t able to ship.

Have a high standard for yourself and your team because time is already against you as you burn through your capital or savings.   In a startup, there are no excuses.  Just fucking do it or don’t.  Sometimes high hopes, encouragement from your friends/family and positive visualization ain’t gonna cut it.

Calculating your runway

Cash is the lifeblood of your company.  Once you run out, your startup is dead and you’re in a pretty sticky situation.  Ideally, you should have enough runway for yourself to live off of for 1.5 to 2 years.  I only had about 9 months in me.  Despite the markets being flush with seed money, there’s no guarantee that you’ll be given a lifeline.  It takes traction, some proof that you have a repeatable business model and obviously a working product released into the wild.

Your focus is to make money in a repeatable and scalable fashion, and not trying to raise money.  It’s a huge distraction and will throw off your roadmap.

Ego

This is related to delusion.  It comes down to not being honest with yourself and your team.  Sometimes living in your own world where nobody really grills or questions you repeatedly makes things easier to cope with.  I remember angrily arguing with loved ones that I *would* make it happen no matter what.  Having too much pride (ego) and being delusional is a deadly mix.  Make sure to have a solid network of friends and mentors who will not pull any punches to get you grounded in reality so you’re not bullshitting yourself or those around you.  In the end, all you have is your reputation so be sure to preserve it by not turning into a complete dick without even knowing it.

Your relationships

Your relationships with loved ones and mentors are some of the few things that can keep you going, sane and collected when shit hits the fan.  Thank you for believing in me and supporting me despite our many heated arguments, Irene.

Conversely, they can be some of your greatest obstacles as their lining of questioning or constructive criticism may instill doubt, fear and belief in your own abilities.  I don’t know the best way of handling this it varies from person to person, but I know this - treat those around you with respect, patience and empathy to understand they mean well.  It’s up to you to discern whether their concerns of your entrepreneurial efforts are genuine or destructive.

Having an awesome (full time) team

Because I wasn’t technical and couldn’t build, after having to let go of my co-founder after my experience at Extreme University, I found myself having to hustle to assemble a new team.  It raised a lot of eyebrows and definitely was not the best way of stepping with the right foot forward on your first startup, but I digress…  Luckily I had a mentor who poured a lot of time, effort and belief into me to make me understand my primary role as a product manager.  He was instrumental in pulling some strings for assembling my team.

The new team (Alvin, Andy, Grace!) I eventually brought on are fantastic people, but they weren’t all in and didn’t have much skin in the game, meaning that Date Ideas wasn’t their full-time gig.  I was the only full-time team member.

In any startup, you need to putting in stupid amounts of hours on a weekly basis.  At best, I got half of that from part time (but awesome) rails developers.  I learned the hard way that you simply cannot succeed with a part-time team.  Needless to say, looking back it was a very frustrating experience, even though it was no fault of theirs.  We tried our best with what limited resources and travelled to Montreal to start having conversations when things were starting to look promising while we had hardly any money.

In retrospect…

It was a pretty shitty feeling (downright depressing, actually) when you know the writing is on the wall and you have to break it to your team, family and investors that you can’t continue anymore.

I could go on and on writing about this seemingly catastrophic personal and professional failure.  I risked almost everything to make something happen.  From the beginning I had no idea what the fuck I was doing.  Today, a bit of that fog is clearing, and I’ll share with you what I’ve been working on in future blog posts.

Sure I’ve suffered a few scrapes and bruises, and incredibly humbled in how hard it is to make it as an entrepreneur.  Learning from many friends, colleagues and mentors (Matt O’Leary, Sarah Prevette, James Woods, Amar Varma, Mark Organ) I realize it truly was a great learning experience and I’m definitely stronger after picking myself back up.  Thank you to Dwayne Forde at Xtreme Labs for being so helpful to Grace and all those I asked for help and advice along the way.  I appreciate the chance and opportunity Extreme Venture Partners bestowed on me for my first entrepreneurial step up to the plate.  I don’t regret having gone this route and I’m forever grateful to my family, friends and mentors.  It’s time for me to start taking care of myself after putting everyone else before me until I’m ready for my next at bat.

If anyone is hiring a person in product management or business analysis/biz dev in the areas of online dating, mobile apps or social media marketing, I’d love to connect with you :)