My Thoughts On Entrepreneuring

Today it seems like everyone wants to be an entrepreneur. In London, you can’t throw a rock without hitting a startup, incubator, accelerator, etc. It’s the “cool” thing to do. A generation ago if you told someone you were an entrepreneur they probably thought it was because you couldn’t get a “real” job.

I was of that time and for better or worse, I have been a serial entrepreneur ever since I gave up being a corporate lawyer in New York City 40+ years ago (the best thing that ever happened to me and the legal profession). The catalyst then was the heady mixture of job dissatisfaction paired with the allure of an entrepreneurial opportunity that appealed to me viscerally, at a real gut level. In my case, it was in Alaska, of all places. I pursued it and have never looked back.

That effort turned out quite well but it only whetted my appetite for further entrepreneurial pursuits. Many entrepreneurs are happy to maintain their early success with the same business for the rest of their working lives. In many cases, that is the smart thing to do. It is very hard to make lightning strike twice in the same place.

Then there are the serials, those entrepreneurs for whom the chase is everything and find success at the end almost anticlimactic. Those inveterate risk takers who are willing to gamble it all confident that their soundness of vision and inability to be deterred will overcome any obstacle. It is into this category that I fall motivating me to undertake my current qiviut (ad)venture at a time in life when most of my peers are perfecting their backswing.

To be sure, not all of my past efforts have turned out successfully and the jury is still out on this one but along the way I have been able to distill a few key points that I think improve the chance for success. For veteran entrepreneurs, I am sure none of these will be revelations but for those just considering such a high-risk gamble and wondering what it takes to succeed and whether or not they have it, they may help.


In my experience, there is no substitute for perseverance, not money, not luck, nothing (although the first two certainly help). As the well-known poem puts it,“Success is failure turned inside out”. When the chips are down, sheer dogged determination, often in the face of doubters and naysayers, will win the day. I believe this more than I believe anything else about entrepreneuring.

If It (Doesn’t) Feel Good, (Don’t) Do It

Many entrepreneurs will disagree with me on this point. They are the ones for whom the process is satisfying enough irrespective of the product or service they are promoting. But I don’t think that typically works for first-time entrepreneurs even if they have that talent. It is tough enough doing any start-up but if you don’t have that fire in your belly or voice in your head telling you that what you are trying to accomplish is positively, absolutely right, it is even harder. Don’t become an entrepreneur just because you don’t like working for someone else or are not sure what you want to do in life or admire someone else doing it. All of these are good motivations in and of themselves but the grass is not always greener. If not coupled with a burning desire and belief in what you want to do, you start out with one hand tied behind your back (making perseverance a lot more difficult to sustain).

Fail to Plan, Plan to Fail – But Not Too Much

Planning is essential in a start-up – up to a point. You need some kind of road map just to keep clear in your own mind where the entrepreneurial journey needs to go and how you will get there as well as to make it easier to communicate that vision to others. Typically, this is a business plan that will force you to think through all of the component steps and the assumptions underlying them. But understand that this plan will never happen as detailed. Reality intrudes to knock you off course. So don’t be one of those entrepreneurs who is intimidated by this first step or agonises over the planning stage to the nth degree only to stumble when executing. Broad strokes are usually sufficient to get something off the ground. There is a good reason investors want to hear elevator pitches. Better to remain nimble, expect the unexpected and re-plan as needed.

Entrepreneurs Need A Sixth Sense: Common Sense

There will be no shortage of “experts” available to tell you how to do what you want to do. Much of that advice will be good, sound counsel. But some of it won’t or just won’t be right for what you specifically are doing or how you work or for a number of other reasons. This is where your entrepreneurial sixth sense should kick in. If something – a colour, a shape, a process, a description or whatever – doesn’t seem or sound right, it probably isn’t. Most entrepreneurs, indeed most people, have pretty good common sense. Trust yours when in conflict with the advice of experts.

“Herd of Musk Ox?”

As the old comedy duo response goes, “Of course, I’ve heard of musk ox!” (although Abbott and Costello used “cows”).

OK, maybe not so funny today and out of context. But my point is that maintaining a sense of humour throughout the entrepreneurial journey is pretty important. In any start-up effort, there will be plenty of times to be deadly serious, frustrated and despondent. It is at these times that a sense of humour, as black as it may be, can reassure you that the world is not coming to an end, you won’t starve and the best is yet to come. I’m not talking whoopee cushions and squirting lapel flowers here, just an ability to step back and see the lighter side of whatever the situation at the time may be. Few entrepreneurs mention this as part of the process but I think it is a vital key to success. It gives you balance and keeps things in perspective.

This list is certainly not exhaustive. I haven’t even touched on the nuts and bolts aspects of entrepreneuring like finances, market research, team assembly, etc. Those things are for another blog. But at a top macro level, I have found these five points to be pretty reliable constants. Will embracing them ensure success? No, but it will improve the odds in my opinion.

Robert J Gould

6 Replies to “My Thoughts On Entrepreneuring”

  1. Bob, as someone who has benefited from several of your ventures as a consumer, thanks for your perseverance…and your wise counsel to other entrepreneurs.

    1. It pretty much conflicts with the first point I made. If you have the mindset of pulling the plug early, you have pretty much abdicated the perseverance concept. In my experience, if you really have a fire in your belly about your entrepreneurial idea then most often perseverance will overcome most obstacles to make it a success. Obviously, there are judgment calls to be made along the way and one size determination certainly does not fit all but if your approach to a start-up is to fail fast, I think it is a self-fulfilling prophecy. With few exceptions, most “overnight successes” take years and an abundance of perseverance.

  2. Bob: I thought this was great and read through it twice. If 20% sinks in, I will be that much better for it.


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