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.
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.
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.
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 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.
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.
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 :)
One of my favourite scenes in Naruto Shippuuden.
Just the other day, I watched an episode of This Week in Venture Capital with Mark Suster.
At one point in the show, he had mentioned that at some point, a “young person” or aspiring entrepreneur should take up a role in sales as it’s a lifelong skill that will pay off in spades down the road in one form or another.
While I was on the fence and had iffy feelings about Sales as a profession and sales people in general, I’m leaning towards Mark’s sentiment towards Sales.
If I were to really pinpoint my “beef” with sales is that it’s highly uncomfortable. Just thinking about it gets me a bit flustered. Maybe it’s the high rate of rejection. (Who likes being rejected?) or my aversion to failure - whether it’s cold calling, prospecting, lead generation and the like, it’s all so foreign to me. You need balls of steel, persistence, and hungry to make money and deliver value. Strangely enough, despite the uncomfortable sentiment towards Sales, that’s what also has me so intrigued and excited to learn about the sales process in general.
An element of being a kickass salesperson is being “fearless” and having a rock solid confidence and belief in oneself that you will prevail overall. I think that’s just a condition of the people you surround yourself with as well as the material you absorb. Not to toot my own horn, but I think I’m a pretty good connector and “relationship guy” and have a strong network of mentors. But that doesn’t quite cut it.
I need to dive into Sales and work in it to learn more about the all the nuances of Sales - as an artform, as respectable profession and as a science.
Outside of doing “biz dev” while I was doing Transforming for SickKids and a bit of freelance for TeamBuy in terms of “real world” experience, I’m slowly going through Neil Rackham’s “Spin Selling” as well as a the Sandler Sales Institute audio course.
Let’s see how this goes.
In a previous post of mine, I wrote about Consistency and Rituals. Today, I’m going to write about my process that leads up to building consistency and rituals - cultivating habits - desired ones at that.
For those who know me, it’s been a bit of a hobby of mine to soak up anything personal development or productivity related. From blogs like Leo Babauta’s “Zen Habits” to personal development systems from Tony Robbins.
Over the last little while, I’ve put a lot of effort into building a “fitness habit”. Just recently, I finished a Crossfit Bootcamp over at Crossfit Toronto. A fantastic program, which is constantly varied, forces you to wake up at an ungodly hour (they only had a 6am and a 7am class.. I opted for the later :), that WILL. KICK. YOUR. ASS. The result is that I feel stronger and more energetic by getting up first thing in the morning and getting a killer workout out of way to set the tone for the rest of my day.
Anyway, a few of the challenges for me before in instilling this habit was accountability and just being plain bored from working out alone. Over the last 3 years, I had started and fizzled out on programs like P90X and Insanity. The thing I sorely missed was that I didn’t have others I was in constant contact with or guidance in order to perform certain movements or exercises properly. I was a loose cannon. I had a lot of freedom to work out whenever I wanted but it turned out I made too many excuses by not putting in effort to block out time at a certain part of my day that was “sacred” to my fitness.
In retrospect, through the bootcamp, I had a few things going for me in building up the habit. For one, I paid $250 for the bootcamp - not a paltry sum so I didn’t want to waste my money, which definitely helped with me following through. The workouts were set for us and our instructor Ryan really pushed us and was ever so helpful in correcting our form - so I didn’t have to put conscious effort in wondering if I was doing things properly - I got almost instantaneous feedback. Also, I didn’t have much choice in what time I was to attend their bootcamp. 6am or 7 am. That was it. Although it was tough the first two days, I quickly fell in line with my other classmates and just showed up consistently. A little over a month later, it feels really weird to not head to the gym for that short hour to start my day or just simply blow off some steam.
A simple concept that Leo (of Zen Habits) wrote about in many of his materials are 30 day challenges. His logic was that anyone can complete a 30 day challenge right? Whether for self-experimentation or simply to pour in conscious and deliberate effort into building a habit and blogging about it for accountability purposes in order to “program” some positive change for the long term.
I think it’s kind of bullshit having to self-experiment in complete isolation with no real-time feedback in understanding a new endeavour properly. I didn’t blog, I just used Facebook’s check-in service to detail my effort to my friends. Those that cared gave me all the “virtual” feedback and encouragement I needed to continue.
Looking back, maybe I was a slow learner, but it simply didn’t work for myself doing 30 day challenges without some community I could lean on whenever I had some difficulties. I’ve a slew of journals that detailed my experiences, but they just trailed off. As with anything in life, simply being *physically surrounded* by people of similar mindset and striving towards a common goal is probably the single most crucial aspect of reaching goal or cultivating lifelong habits.
Come to think of it, this resonates in all things I’ve done where I’ve experienced any modicum of lasting success. Having some sort of in person community (not just virtual) that will push, encourage, keep you accountable and kick your ass (in a good way) to prevent you from failing or faltering.
Sometimes things can’t happen no matter how badly you want it to make it happen — at least not in the timeframe you originally wanted.
I realize that with Date Ideas first iteration in Rails 3 proper (finally!!) behind me with its imminent launch, despite several setbacks and months of delays, that I accept it for what it is - something that can grow organically and where me and my team can learn from as our first stab in the consumer web startup space.
It takes a very special set of circumstances for a team to come together. The right timing, stage in life, mindset, passion, money in the bank for decent runway, having a full moon and the perfect windspeed, whatever it is to be aligned perfectly in unison to start and build something great.
Despite your being “relentlessly resourceful” and no matter how hard you try with boundless passion/enthusiasm, sometimes things that can’t happen now doesn’t necessarily mean it can’t happen later.