The startup smoke test: three factors for entrepreneurial success
What do you think indicates the success of an entrepreneur? How hard you’re willing to work and how forgiving your family is? How long you can last eating nothing but instant ramen? How many people you know who wear a suit regularly?
It’s a mystical formula, and every successful entrepreneur will seem like an outlier, with some unique background or opportunity that you can’t possibly identify with. I even found myself saying the other day “Well, if I’d chosen to go to Stanford for grad school, and I were a few years older, and…”
Having said that, successful startups have certain qualities in common among their founders, and this triangle — which I stumbled across in Simon Middleton’s excellent “Build a Brand in 30 Days” book — totally resonated with what I’ve observed and learnt, so I decided to share it with you.
(Derail: The aforementioned book is terribly named. I randomly saw it in Borders, as part of my regular management/business porn browsing, and a quick flick through redeemed it. It’s not a 30-step “learn PHP in 24 hours!!” style brand intensive so much as a guide for small business owners and entrepreneurs on how to figure out what you’re all about, and how to present that to your potential customers. I haven’t got to the online section yet, so I may change my mind…)
The triangle of success
Here’s Simon’s exercise. It can work for individuals or teams.
First, write down your talents. What are you good at? What do you have a proven track record in? If a stranger read your CV, what would they think? What do your friends and business acquaintances say you absolutely rock at?
(Your friends might laud your event planning skills to the skies – you’re the one who always gets the trips and parties together without any stress or fuss. Your coworkers or boss might have no clue about that, but describe you as a deeply logical and analytical person. It’s interesting to get both sides, and I have always been surprised as to how people describe me.)
Second, write down your passions. No matter what they are, how silly or idealistic, just get them out. Are you a die-hard scrapbooker? A World of Warcraft fanatic? Are you drawn to helping others, working with children, preserving the environment? If you won the lottery, what would you do? Make a list of the hobbies, side projects, volunteer activities and events you have been involved in over the last year (or whichever time period makes sense) – do you notice a surprising theme?
Now look at both lists. Is there a magical connection? Are you by any chance a deeply skilled database engineer and also fortunate enough to have a true passion for data storage? Is your talent in visual communication and design, and you really love creating new illustrations and flowing presentations? Maybe you’re the go-to party planner among your friends, and you happen to have a deep love of the romantic, especially weddings.
If there’s no obvious connection, maybe there’s a more subtle one – you’re really good at solving hard problems and allocating resources, and you’re passionate about your business idea, so your talent will come into play while actually running the business. Or you can develop the skills and credentials needed to follow your passion, such as doing a degree or course, getting more experience, or simply giving it a go and learning. If you have a solid track record in a field but aren’t sure how to connect that to what gets you really motivated, the next point may come in handy: turn it on its head, and think about the problems and solutions that relate to both areas, and maybe you’ll discover something interesting.
The final step is: assuming you have a business (/idea), what is the evidence of a market? What problems and solutions do your potential customers face, and what supports the theory that your idea is The One? A great situation here is when you are your market, and you have a strong belief you are not an outlier; many technological projects and companies have been started simply to scratch a personal itch.
Combine these three elements and you get:
If all three are aligned, you’re in an awesome place, better off than most. But even if two are aligned and the third needs work, you’ve got a great foundation – and you know what needs fixing! You can now answer the question “Who’s the first hire” with confidence. If you’re over in one corner of the triangle, don’t give up, but use the answers above as a base for your next steps.
Which is the least important? This is totally arguable and there are counter-examples of just about any configuration.
Highly skilled people without a true passion for the idea, but with a great market demand and obvious direction to go in, can get caught up in the process of running a startup and develop a passion — often because their customers have one, and after a while, you see everything through your customers’ eyes. Whenever I see a really dull-looking startup I chastise myself for judging, and realise that to those knee-deep in that particular problem, it’s probably surprisingly interesting.
People driven by passion and a need, but without the skills needed to excel at it, can still do pretty well. You can buy in a lot of skills, finance and legal being the obvious two. The issue with this setup is getting the initial traction – why would people come to you, trust you over others, or invest in you? Assuming that everyone is good at something, you might be surprised how your apparently useless skills have a way of making themselves useful later down the line. (The number of times I end up using skills I learned from improv in the totally unrelated world of software is frightening.)
If you have passion, and skill, but no market, you could be in a sticky situation — but especially if you have passion, there are likely others that do, which means there are customers, and you just have to figure out what they would pay money for. It’s wise to use customer development strategies and rapid iteration so you can try stuff out, figure out if customers would buy it, and pivot (which is just trendy-speak for ‘change what you’re doing’) if they won’t.
So that’s the triangle of success, and a quick three-step self-evaluation process. Make it your smoke test before you dive headfirst into an idea you care little about, with no guarantee anyone else ever will, and lack the ability to execute.




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