Entrepreneurial Career and Life Design

Chapter 6 – Managing Risk Using Prototypes and Portfolios

Watch Module 6 – Hunting (7:26)

Watch: Module 7 – Affordable Loss (15:04)

As you work on Assignment #3, you should have several well-refined Career-Related DCQs and know which entrepreneurial methods and tools you are following depending on who your customer is. You are using a number of divergent and convergent tools to research, interview, network and get to know your potential customers. You are setting goals, managing your time and achieving your daily To Do list of activities to ensure you stay on track.

So now that you are off and hunting for customers with your first handful of principles and tools, I thought it would be a good time to give you a fun video with a hunting analogy and a lighter approach to remembering and using the principles and attitudes associated with your effectual search-based approach to discovering what kind of career will bring meaning, well-being and happiness to your life.

It’s also time to give you a few more principles and show how they can help you improve your search as your make progress during Assignment #3.

We’ve covered 4 key principles so far:

ENT Principle # 1 – Bird-in-the-Hand. Start with your given means. David is a great artistic image to remember this principle by. A young boy, armed with nothing but a slingshot and belief in his own skills and the righteousness of his cause brought down the greatest warrior of his age. A great role model for any entrepreneur fighting to survive in a world full of giants like Goliath.

ENT Principle #2 – Experiment and Learn using the Diamond Design Thinking Method. It doesn’t matter what your hopes and dreams are, you need to test them against reality using the Scientific Method. In the same way that scientists use reason and experimentation to discover the laws of gravity, entrepreneurs use design thinking and lean methods to discover the laws of the market. But use the right tool – don’t bring a knife to a gunfight.

ENT Principle #3 – Radical Collaboration, Radical Candor and Crazy Quilt. Never Go Hunting Alone! You are looking for weak signals and you may need help when you find your prey.

ENT Principle #4 – User-Centricity. Think Like Your Prey. Understand your customers’ problems before you try to sell them on your solutions. Follow the Flow. Understand your customers’ habits and behaviors in order to find their watering holes (i.e. conferences, networking events, blogs, magazines, etc.)

We’ve also touched on several important entrepreneurial attitudes and mindsets like curiosity, alertness, proactivity, and re-framing. You can remember these with the principle or expression “Never Stop Hunting” (Image from Covertress.blogspot.ca).

You may recall from ECLD Module 3 that I also gave you a bonus principle I discovered while Hiring a VP Sales at 3DNA – Deliver Value Before Asking for Value Principle and the power of volunteering before taking a job. I’ve heard this one also called something like “Dig the Well Before You’re Thirsty”.

This principle will become increasingly important to you as you meet with more interested potential employers/customers/partners/connections. Sometimes you need to give something to your network before you can ask for something from them.

Deliver Value Before Asking for Value Principle

When I was CEO and Co-Founder of 3DNA Corp., a Toronto-based startup company building immersive 3D Desktop software sold to graphics card, motherboard and chipset companies as well as consumers, we wanted to hire a VP of Sales. We found an interesting guy, Dave, living in California with significant experience in the gaming industry. He seemed like a very strong fit.

We wanted to offer him a position and discuss his salary and stock option expectations. He demurred and suggested that he work for free for us for a few weeks and set up client meetings for us at an upcoming trade show. (I think it was the Electronic Entertainment Expo or COMDEX in Las Vegas.) Boy we thought we were getting a good deal since we didn’t have much cash and our revenues were less than $1million at the time.

Dave exceeded our expectations! He seemed to know everyone and pre-arranged meetings with high level executives at all the companies we most wanted to see, including hardware vendors, game publishers, magazines and a few customers we hadn’t even imagined. His in-person sales skills were amazing, asking targeted questions about who the decision makers were, their budgets and signing authority, purchase process, next steps, and clarifying objections and proof-points. He seemed to really “get” our company and our products and be able to pitch our vision without us having to train him.

By the end of the trade show my co-founder and I were drooling. Dave was perfect – we had to hire this guy! Then we finally discussed his salary and stock options and we ended up giving him far more than we had ever budgeted for. If he had told us what he wanted before the show, we would have laughed and said no. But after delivering value and proving himself to us, we paid way more than we could have imagined and were happy to do so.

I learned a real lesson by forming this principle and I’ve followed that same principle with almost every one of my clients ever since. I formed a principle to “always deliver value before I ask for value”. Get to know the client, impress them, and allow them to recognize the tremendous value I can deliver before I tell them what I’d like to be paid. People rarely try to bargain me down on my fees after they know what I can do. If for any reason I can’t deliver tremendous value, then I normally decline to ask for the contract.

An expert entrepreneur should be fluent with dozens of principles, rules-of-thumb, stories, heuristics and expert scripts. These are powerful ways to remember how to act in any given situation. This is why so many successful entrepreneurs and executives write books about their top 10 leadership lessons, or top 20 things an entrepreneur should do, or the 7 habits of highly effective people (now with an 8th habit and sold alongside its companion Franklin-Covey Day-Timer). These experts summarize and essentialize the lessons learned during their successful lives and give them to you nicely pre-packaged with examples and stories. But simply reading about something in a book is not of much value if you have not consciously memorized it and practised how to apply the principles to your own life.

That’s one reason why stories are such a powerful way to convey principles through “The Moral of the Story”. Stories are sticky. People remember them and can more easily remember the morals embedded in a good story. Who can forget “The Boy Who Cried Wolf” or “Don’t Kill the Goose that Lays the Golden Eggs”?

A former boss of mine used to annoy me with his stories. I would ask him what to do in a given situation and he’d invariably reply with “Let me tell you a story about that.” I wanted a quick 10 second answer and instead always received a 5 minute story and then still had to figure out for myself what to do. I hated it at the time, but many of his stories still stick 20 years later and I have long ago forgotten all the specific situations! I now find myself doing the same thing with my students. They want a quick answer and I reply with a story and a principle or two to consider. [I’m sure they love this as much as I did!]

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Like my younger self, I find that many students prefer simple answers and like to blindly follow a prescriptive step-by-step method or process rather than figure out how to apply the more abstract principles and mindsets. It takes less effort and if it doesn’t easily work the first time, then just ask for more instructions or another simple answer or tool to use.

We’ve also been deeply trained by an educational system designed for us to sit in rows and follow the same instructions as everyone else to create obedient citizens and rule-following employees. We’re trained to follow established rules of order, give the correct answers and fit into corporate hierarchy structures. In this teacher-centric teaching approach to education, the teacher knows the answers and transfers that knowledge to the student primarily through lecture, textbooks, and examinations by the “sage on the stage”. There are right and wrong answers (goals) to be learned (using planning-based logic).

These step-by-step approaches don’t work very well for entrepreneurial effectuation search-based design and discovery. Instead of teacher-centric teaching, the educational pedagogy is based on student-centric learning where students have to discover for themselves and construct their own learning. There are no right and wrong answers to questions like what career might bring you prosperity and happiness. Or who your customer should be. There are hundreds of different perfectly valid paths you can take and lives you could happily lead. There are many potential goals/hypotheses you may pursue with your design challenges. Instead of answers to be taught, the educator is a “guide from the side” helping coach students to apply principles using a student-centric experiential learning approach. The educator sets the learning environment; provides content, assignments and coaching; and helps the students figure things out on their own or with their peers.

In order to be learned and integrated into your activities, principles must be consciously called into your active mind in order to be applied to any given situation (e.g. “which element of active listening should I apply to this current conversation”). After consciously practising a given principle over time you eventually transform it into a Mindset that you apply almost automatically as a habit. It’s kind of like playing the guitar. The scales are principles that you need to practise and practise until they become automatic and your fingers seem to fly over the fretboard of their own accord to nail the right notes without you thinking about it at all.

ENT Principle #5 – Affordable Loss

ENT Principle #5 – Affordable Loss gives you some additional advice now that you are off and hunting your customers, interacting with them, segmenting them, understanding them and using divergent and convergent tools to document their problems that you might be interested in solving. This principle involves more than just establishing what you are willing to lose – it also includes the idea of using a portfolio approach and prototyping.

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We’ve all heard the expression “Don’t Put All Your Eggs in One Basket.” You can rarely expect any single job to help you develop all the human and social capital you need for your next job. Employers in general care about training you to meet their needs, not some other company that you might work for next as you advance in your career.

That’s why I am strongly urging you to have a portfolio of design challenges and consider making progress toward finding a job, but also toward building your human and social capital outside of that through side-hustles and/or changemaking involvement (as shown in the figure).

This portfolio approach holds true in most aspects of your life. Don’t invest in only one stock – buy a portfolio of stocks or mutual funds. Don’t play only one sport – try a number of them to discover which ones work for you and expect to change them as you age. Don’t have only one friend – seek out relationships in a variety of areas with a number of people. Don’t interview for only one job – shop around. Don’t expect to have one job for the rest of your life – anticipate changing jobs every 2-3 years on average and having several major career changes during your life.

The other important aspect of this principle is the idea of prototyping everything. Prototyping is absolutely fundamental to design and design thinking and is normally considered to be its own tool and one of the stages in every method or textbook. Instead of spending 2 years building the “perfect” product (that nobody wants), get a rough prototype into a customer’s hands (or Minimum Viable Product – MVP) early and start getting feedback and learning and pivoting. Here’s one sub-principle that I’ve discovered.

Remember the Grape Vines Principle

My wife once asked me to cut a few pieces from the old grape vines in our backyard so she could make a Christmas wreath. In my enthusiasm, I did a good job clearing away a fairly large section of wild grape vines and gave her much more than she needed to do the job. Instead of being thrilled with the large selection of vines, she was unhappy. “Why did you cut down so much? The vines looked charming before. I just wanted a small amount.” She said, “Now it looks bare and it will be over ten years before they all grow back.” I should have cut down the minimum required, seen how it looked, consulted with her on this prototype and then gone back later to cut down more if needed.

I had failed to follow the Loss Avoidance Principle! In fairness to me, effectuation had not yet been published so I had never learned this principle. My wife and I had to create our own new principle and now, whenever I am gardening or trimming trees, we tell each other “Remember the Grape Vines”.

Recently a couple of trees needed to come down at my wife’s family cottage. The arborist in charge of the job convinced us to cut down several trees more than we had planned on. Afterward we were very upset. There is too much sun on the cottage and an empty space we don’t like. We forgot to “Remember the Grape Vines.” We should have told them to cut down only 2 or 3 trees first, seen how that looked, and then asked them to come back again if more trees needed to go, or we could have had them remove just a few branches. There are so many incremental steps we could have taken, but we forgot to “Remember the Grape Vines.”

You can prototype virtually anything before you go “all in”. If you are interested in bicycling, you should start off by renting a bike or using someone else’s bike to prototype how you like it and what style of biking you prefer (off-road, long-distance, touring or just exercise around your neighborhood). Don’t run out and blow $8,000 on a top-end model that you rarely use.

The same principles apply before getting a pet dog which you will be stuck with for 10-14 years. You might want to care for a friend’s dog for a few weeks first, or try providing a foster home for a dog or even start with an easier pet first like a cat or hamster. This last idea works especially well as a prototyping tool if your children want a dog – get them a plant or hamster first and see how well they handle the responsibility.

In a similar vein, don’t just agree to marry the first person you meet or the first person you date. You can apply the explorer mindset (i.e. curiosity and experimentation) to first get a divergent set of experiences with different people and develop insights into the kind of person you might want to spend the rest of your life with, and the kind of relationship you might want to have. You can apply the Affordable Loss Principle to prototype what such a relationship or marriage might look like. You can go on a number of dates in different circumstances and see how the prospective candidate interacts with your friends, family and work colleagues. You can travel together on a vacation or go camping together to see how the other person deals with uncertainty and getting out of their comfort zone. There may be rare “love at first sight” experiences that work out “happily ever after”, but the rate of divorce seems to indicate the people could learn to look a bit more closely before they leap.

This brings up the question of having children, a major life-long commitment from which you cannot get divorced. Here again you can prototype before committing by spending time with other people’s children, interviewing parents, analyzing how much education and child care cost, and trying to determine if having children is a higher value to you than other values you might pursue if you chose not to have children. If you really love children, perhaps your career could involve teaching or coaching kids before deciding whether or not to have your own. The key is to make all your choices based on prototyping and experimentation and not have a decision thrust onto you accidentally or by making no choice at all.

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Entrepreneurial Career and Life Design Copyright © 2024 by Dr. Steven A. Gedeon is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License, except where otherwise noted.