It’s now mid-2018 and I’m updating a post from 2016 with the added benefit of perspective and clarity. My older post had mostly the right stuff, but this one is designed to get more to the point.

There are tons of great advice out there shared through blogs, startup events and knowledge-sharing forums aimed at nurturing the startup ecosystem with a view to optimizing the success of its members. In truth, you have to extract those nuggets of wisdom from a virtual deluge, not all of which is sage advice or otherwise on point.

So, this post is about the more potent common denominators of what others have shared that intersects with my own beliefs and experience. These elements sit at the very top, such that any entrepreneur should aspire to have all in common. Be deficient in one or more of these, and your path to success will be anything but linear if not completely uncertain.

  1. You can spot an opportunity.

Many entrepreneurial ventures start with a product idea. When I get exposed to one my first question is “why are you developing/marketing this product/service?” – and I listen intently to the answer. The true magic lies in the why, not the what.

Most of us can ideate, but not that many of us can find a viable opening in the market. The best entrepreneurs are less passionate about an idea and more hyped by the opportunity created by an unmet need. Because if you can find that, you can always come up with a product or solution to fill it. Taking a product and trying to reverse-engineer a market for it – the reverse paradigm — works much less often.

To get to the right opportunity from wherever you are in research and development, you have to have the ability to ask the right questions. You see this at play in Shark Tank type environments. The investors involved in these productions are sophisticated in how they evaluate a pitch that outlines both opportunity and solution. In real time, they can draw from piles of mental frameworks build from years of experience evaluating business models to poinpoint the exact questions to fill information/insight gaps. Almost instantly, they can with a high level of confidence assess a business opportunity.

Most entrepreneurs don’t think this quickly, but the need to prioritize the key questions that map to critical success factors for your busines is nonetheless there. And this theory applies through all phases of the business lifecycle as a necessity to focus your time and resources on the matters of greatest impact to your success.

The final and arguably most important key to identifying an opportunity lies in not only your passion and inquisitive mind, but a virtual obsession with people who may become customers. Your success in spotting an opportunity lies in your ability to read and understand them. You know not only their needs but also the emotion behind the needs that drives them to engage with or pay for a (better) product. You know how you are adding value because of how they currently solve a problem and why your solution is distinctly better. You know under what conditions a potential customer will merely like your product versus actually use it….or better yet, advocate for it.

People/customers are super tricky to sort out. They don’t know themselves all that well while they both purposely and inadvertently mislead you. It straight up takes time and experience to untangle the details of what they say and do.

  1. You can create a customer experience.

Our deep knowledge of people comes in handy here along with a profound desire to serve them at every step.

A long time ago when I worked in web marketing, I read an article where the author compared a digital journey to taking a flight. This one event is completed through a long list of smaller tasks – such as parking, check in, luggage drop, screening, gate access, boarding etc. The extent to which the ‘flight’ was a positive experience  depends on each step being a delight, or at least exactly as expected. One mess up and you ruin the whole thing.

As entrepreneurs, we have to consider every moment when our customers engage with our product. One false move and we risk disengagement. For this reason, so many app and digital platforms fail, even when the core proposition was solid. We have to overthink the customer journey and nail it, or we have lost that customer for good.

I don’t find this sensitivity to be in great supply based on my interactions to date, especially with new entrepreneurs. Here in Toronto there is a periodic city-wide open house day for startups. The general public including other entrepreneurs can visit and meet the teams and network. I have attended many….and boy, what a disparity in experience. I would say less than half of the startups occur like they were expecting you: greeters at the door, timed presentations, drinks, engaging conversation, stations to visit. The rest just couldn’t bring themselves to leave you feeling like you mattered. I have been stuck on a ground floor of a building because I needed a pass to get to the desired floor. I and others have walked into an office and stared at other guests arriving wondering what to do. I have even been in environments where no more than a dozen people were in the room, half of which had company Ts on – yet they talked among themselves and ignored the guests. Yet, these are professionals designing customer journeys for themselves or their clients. I could easily tell which ones were more likely to be successful at it.

And lastly, while you’re off building a customer journey, you can’t lose sight of the roots of your opportunity, along with the key features and benefits of your product that are required to seize that opportunity. Your path as an entrepreneur is to ensure strong connective tissue from opportunity to final product, with all decisions embedded in what’s best for the end user.

  1. You can package and sell your idea or product.

This point is one that’s almost parenthetical but is worth mentioning. If you ever talk to smart peeps in PR, they will tell you that in the startup world especially the biggest challenge to driving awareness and traction in media is teaching founders how to talk about their product. Yup, you have to get your messaging right or else you’re wasting your money sharing it to drive your business.

Any it’s not only messaging; the key messages and insights have to be sequenced and intertwined into a provocative whole. We call that storytelling, which is an essential skill all marketers and entrepreneurs need to motivate all constituents.

Same goes for the process of generating investment. Same also goes for inspiring and creating engagement in your team. You have to have the skill set to communicate clearly and in a universally-relevant way, or you’ll spin your tires.

And then, of course, you have to sell it to your customers. That’s where that intimate knowledge of your customer thing comes into play again. You have to establish a brand and communicate in the right tone and voice. More importantly, you have to know the triggers that motivate your customers to think and act the right way, which requires deploying your message using the precise words to match how your customers language their situation to themselves.

  1. You have vision.

Business-wise, better than 20/20.

Yes, your startup idea is very 1.0. It’s an idea, a product. It’s one thing.

But that one thing doesn’t drive never-ending growth and it can’t be expected to generate sustainable profits. It’ll feel like it at first; I mean, there are 8 billion people on this earth, and it takes a minute to get to all of them. When you’re small, 300% growth comes weekly; that phenomenon becomes intoxicating and creates a sensation that you’re on your way.

Then suddenly, you’ll hit a wall, and it’ll happen almost overnight, when the lake of interested customers is fished dry. Or, you get so big that you attract competition, some of which who work to discredit you.

Ongoing growth is more likely if you have a mission and a vision attached to your product idea – a sense of what you want your new company to be when it grows up. What impact you want to have on the market and society…and what is the product roadmap that ladders up to it.

That kind of thinking leads you to new product ideas and revenue streams. By the time you scale your company a little you have to shift from your 100% focus on this cycle’s results for this product. You have to split yourself off to plan for your next startup within the startup, all in the context of your vision for your company and where you think the world is headed.

Google never planned on being a search engine company for eternity. Search was a means to an end, for it meant volumes of customer data that would open up countless doors. Now, you don’t have to think on that kind of scale but you as a CEO definitely need to know where you’re headed. If you don’t, you’re likely headed to obsolescence.

  1. You go through walls.

In many articles you’ll read about how founders must have ‘passion’. I simultaneously nod my head in agreement and roll my eyes in irritation. Passion is a good thing but it’s not worth much unless you engage it to do something important. Otherwise you’re just a bundle of directionless energy that eventually becomes rather annoying to talk to.

And the things that are most important in business are often the tough things. And your passion must give you the drive to address them.

The more common examples of entrepreneurial challenges include: being able to make difficult complex decisions when no one else can; being told NO many times, yet still finding a way; having courage to pivot when your idea isn’t working; finding new growth avenues when progress has slowed.

What’s even more important is the passion to tackle difficult people challenges. Engaging in tense negotiation, resolving conflict, giving difficult feedback – you have to be about all this stuff. And I worry about this when I see the latest trends in business practice. We are more and more becoming a society that bails or ghosts when awkward or difficult situations arise. Otherwise, we de-prioritize the stuff we don’t like until issues fester and become something more calamitous. These habits challenge our reputation to manage, partner and lead…and ultimately progress.

(Heads up: two paragraph venting digression!) I myself just lost a business partner of sorts, who for a year had been bartering help with each other’s app because he didn’t know how to tell me in a meeting that he wanted a deeper, more embedded relationship with shares. Instead, he asked me a vague question in the hopes I might get the message and just offer them up. I didn’t get the point of the question so he didn’t get the answer he had hoped for. We continued merrily on with other subjects to plan next steps for the coming months. Little did I know he at that moment planned to go in a different direction, because he chose not to even tell me. Ok well he did months later, when I was chasing him for an update. Sigh.

The funny thing is, this wasn’t even a tense issue. He could have easily had shares if he had asked with some defense of his position. I would have been totally open to and we would be rolling along at this minute as we had all along. We worked so well together. I was considering reaching back out to him to offer the shares and re-engage, but changed my mind. I realized I no longer saw him to have the necessary chops to partner and run a company.

I’ll offer that it’s not only important to be ‘OK’ with tackling tough stuff, but it’s better to crave to tackle problems. I’m going through this right now with the app I’m developing. I have been showcasing the value proposition and detail with close business contacts with a view to finding problems. I don’t need validation — I know it’s a good concept. What I’m trying to find is what criticial issue am I overlooking….or what user insight am I missing or did I read wrong. I’m 100% looking to punch a hole in the concept, and then close it. I think that mentality will serve me well.

I have met and guided other entrepreneurs who have taken exception to my constructive feedback, even when asked. In my view, I think I’m helping them by pointing out vectors working against them. To them, it’s like I bullied their child. I don’t get it, and I’m lefting wondering if they will as well.

The last and most important element of going through walls is the idea of ‘without fail’. This is also something I’ve had to adjust to since leaving Tier A corporate marketing. Not coming through for a teammate or business partner — even for something small — is not an option. And I’m talking about people with crazy robust lives, who work 12 hour days, run marathons, serve on boards and raise a pack of kids. It’s rare to have to follow up on a commitment of any sort. I rarely get return emails that way “oh, sorry….been real busy. What did you need again?” (even though it’s all laid out in the email thread if you scroll).

I’m not saying that entrepreneurs don’t honor commitments or drive to milestones with unwavering focus. What I am saying is that while many do, many (many) don’t. These days I spend way more time following up and repeating myself….even on matters that are way more about the other person than me.

It must be said that going through walls is all for the sake of a clear outcome on the other side. In a very early article I highlight results orientation as a top ‘soft’ skill for marketers. I stand by it. As for you, set your goals and your milestones, and then use your brains, your brawn, your passion, your willingness to do the hard stuff. Without fail.

  1. You are self-aware.

This is the catch-all, because if you are lacking any of the above (or other important attributes not on this list) you have to know that you have this gap. If you do, you’ll move to close those gaps through the partners or close advisors you recruit. If you don’t, you are likely to make a raft of bad business decisions, and more importantly, you’ll be working those notorious 100 hour weeks because so much of what you yourself have to do will be new to you.

Yes, as an entrepreneur you’ll be working on a small team for at least the first year or two. So, if you want to be efficient and move quickly, you have to start the profession with not only the above personal attributes but with a multitude of technical business skills. To make entrepreneurship feasible for you, you and your team had best begin by already knowing how to do many things. If you don’t, everything you do will take you 2-10x longer than a skilled person. And you’ll be exhausted and overwhelmed. Daily.

And the list of things to know is exhaustive. Ask yourself, how quickly can I:

  • identify and recruit talent well?
  • compile financial statements, diagnose problems and take action?
  • develop advertising assets and buy media?
  • determine in a marketing partnership meeting if synergies are there and a deal is possible?
  • create a pitch deck that tells a compelling story?
  • create and upload an employee performance measurement program?
  • unocover user wants and needs, even when potential users don’t know what they want or why they want it…and never mind the fact they tend to misrepresent their feelings on the regular?
  • map user needs to specific features and benefits to create a winning value prop?

This is only the tip of the iceberg. The real list goes on for pages.  Are you ready…and how fast can you move? Your cycle time for every little thing you do will have as much to do with your long term success as your core business idea. You risk ending up buried in to-do-list hell.

I have met a solid handful of individual entrepreneurs or small sets of partners who in totality are missing a number of these fairly basic superpowers. Yet, they don’t know what they don’t know. These are the circumstances that cause me to take a giant step back when it comes to getting involved. I just don’t have the energy to invest in convincing someone how improperly they are set up to succeed before I can even get around tohelpind them address the situation.

  1. You process information and advice well.

If you’re self-aware, you know you have gaps in knowledge and wisdom that you seek to close. You do this through people and resources.  The sensation of what comes at you amounts to drinking out of a fire hose, for there are now endless terrabytes of information and waves upon oceans of advice to be had if you seek it.

The challenges are these: not all you take in is correct or properly contextualized; great advice is hard to find and often comes from unlikely sources; the more information you gather, the tougher it is to reconcile, because much of it starts to conflict.

What makes being a business person so tough is that you simply cannot accept all of what you hear, what you read and what you told at wholesale value. Data is data, and that’s a whole separate process and skill to mine it, extract insights and tell stories with it; but as for the rest, you must filter, process, reconcile and harmonize all that you have to extract what’s right for you and the business you manage. And that’s all on you — especially if you’re an entrepreneur, when you have no one above you to make those calls. Your ability to manage the complexities of a runaway ecosystem that generates fact and opinion in hair-raising quantities will greatly impact your outcomes, or at least the extent to which your path to achievement is linear.


Yes, to succeed as an entrepreneur requires many things. These to me are the ones that sit at the top, that apply to practically every situation. The others you may be able to do without, at least under certain conditions. Great entrepreneurs know themselves well; they can see, create and communicate. And once the stage is set, they just make it happen.



If you’re not sold on my article, this post from Product Hunt is an outstanding collection of some of the better advice from an array of successful business people.  🙂

April 2019 – LOVE this article about how ‘finding your passion’ can be a trap. Some great insights to think about when considering entrepreneurship, including the pitfall that we expect our passions to be pursuits that are natural or easy for us. They often are not!