Conversation Agent: Conversation with Skip Shuda on Entrepreneurship

In 2000, just when the technology market was starting to see signs of overheating, I decided to join a technology start up: Destiny WebSolutions.

I quickly became familiar with and very fond of Skip Shuda’s interconnected and highly fascinating way of thinking and talking. An advisor-builder with a sense of adventure, Skip founded Destiny WebSolutions in 1994 after having worked with numerous startups since 1983.

Destiny was named Startup Company of the year in 1998's Philadelphia Area Enterprise Awards and grew to $25 million in annualized revenues in 2000, employing over 120 people. Today Skip enjoys working with technology startups at Team and a Dream, using his experience, lessons and tools to assist fellow entrepreneurs.

As part of his work with entrepreneurs, Skip identified his eight Entrepreneurial Archetypes. He describes these in his blog – and you can find details at the bottom of this article.

So Skip, why recreate typologies (archetypes) for entrepreneurs?

Skip: I've only found one typology specifically targeted to entrepreneurs although there are numerous other kinds of typologies to help describe aspects of people's personalities. It turns out that people have been thinking about "types of people" for quite a long time. Around 400 B.C., Hippocrates articulated four human temperaments. More recently, types have been defined by Carl Jung, Isabel Briggs Myers, David Keirsey and many other researchers. Other insightful profiles include DiSC and Enneagrams.

These types are addressing the entire human population. The challenge that I face is that I am working with a subset of people called entrepreneurs. In the case of Team and a Dream business, it is even more specifically focused on technology entrepreneurs (i.e. those dealing with internet, software and related technologies). I found one typology for entrepreneurs by John B. Miner in a 1997 book but, with one exception, Miner’s types didn't really seem to address what I had been seeing in my entrepreneurs.

I realized I was starting to see recurring needs from the entrepreneurs I worked with. The interesting thing was that, based on the recurring needs, I recognized some other similarities between the entrepreneurs. One set of entrepreneurs really needed a marketing plan, but knew their technology inside out. Another group was seeking navigation through the whole startup process with a technology chasing a market. Still others had wide-eyed visions of how they would change the world.

This recognition of common themes and patterns is what led me to sketch out my initial list of seven technology entrepreneur archetypes. I have since revised it to include one of Mr. Miner's types, bringing my total to eight archetypes. Although my experience base is drawn from technology entrepreneurship, I believe these may have relevance in the broader arena of all entrepreneurs.

What main characteristics did you use to categorize Team and a Dream Eight (8) Entrepreneurial Archetypes?

Skip: Deep motivation is front and center. I tried all sorts of dimensions when I tried to understand these patterns. I looked at stages of life, business experience, gender, business domain, business goals, etc. To some extent, these are all represented in the archetypes that I currently track. However, none of them captured the essence of the different entrepreneurs as well as their deep motivation for starting a business.

When I say deep motivation, I mean that I am getting beyond the first 1 or 2 or even 3 answers that they give me to the question, "Why are you starting this business?". Oftentimes, that conversation goes something like:

"Why are you starting this business?"

"To get rich! Buy a nice house, provide for my family, etc."

"But you are a smart person... there are a lot of ways for you to make a lot of money. Why are you starting this business?"

"Well, I'm tired of seeing all of my good ideas being dropped on the floor by the corporate types. I also think I've learned enough about running a business that I'm ready to try my hand."

"Okay. Now we're getting somewhere... So which is more important to you, gaining some freedom from the corporate structure to exercise your own authority and build a business or to pursue your specific technology idea?"

And so on. You get the picture. In this dialogue, we're really starting to understand what makes this person tick. And what makes them tick comes will all kinds of strengths, biases and challenges. That kind of understanding allows Team and a Dream to more effectively meet their needs... and, I believe, improves their overall chances for success.

How are technology entrepreneurs different from regular entrepreneurs?

Skip: The technology entrepreneurs are what I know, so I'm sticking to my knitting. I’d be willing to bet that you'll find non-technology entrepreneurs who fit these types. However, it’s likely that I'm missing other kinds of entrepreneurs through my tech focus. For example, the archetypes really don't address family-started/run businesses. For a while, I was tracking "intrapreneurs" which I defined as entrepreneurs in corporate settings. However, I didn't feel that I had a rich enough experience base to comment meaningfully on them.

The domain of technology creates a specific set of challenges for entrepreneurs. Some quick examples might help. The markets tend to be emerging and rapidly changing. Competition is often hidden and can come from all camps – large and small. Tech entrepreneurs must have a deep reliance on virtual team members and partners.

Your career in technology spans 23 years. Can you tell me if the discoveries you summarized in your findings are consistent over time?

Skip: It’s a good question. When I graduated from the University of Delaware in 1983, I took the lowest paying job of seven offers so that I could be employee #16 in a rapidly growing, venture-funded software startup. When I reflect on my experience with entrepreneurs over the past 23 years, I believe that I could find many of the archetypes. However, I think a couple of the patterns have emerged more recently as technology has become more accessible. For example, student entrepreneurs are far more prevalent than they were when I graduated in the early 80s. In addition, second career professionals are now finding that the barrier to entry into the technology market is a lot more manageable. This has given rise to a growth in the types that I call "Get Big Fast", "Freedom Builder - Industrialist" and "Spice of Lifers".

What is your favorite a-ha story about second career professionals? I always thought that the entrepreneurial bug bit one early on, but maybe things have changed.

Skip: My favorite a-ha! story has to be a conversation I had with a good friend recently while talking about the Entrepreneurial Archetypes. He asked me what kind of entrepreneur he is and I quickly responded with a chuckle, "You're not an entrepreneur!" I said this because he is a classic corporate executive. As an accomplished businessperson, I never thought of him as an entrepreneur. However, as he went on to describe his business idea I realized that he fit the pattern that embodies a second career professional, what I call "Spice of Lifers". His business idea was to follow his passion for wine investing and to create a Web site that catered to other investors like him (as an aside, Team and a Dream helped to create this site at www.wineinvestor.com). These entrepreneurs are often very business savvy and have a really strong understanding of what they need and want out of a business. They are often looking for life-work synergy and balance with some form of a creative outlet.

I met an MBA student at The Fox School of Business who shared some thoughts on his life. Rajesh is a student, a father, and a passionate technology entrepreneur who's excited to be leaning more about marketing. I found his energy contagious. Do you find this kind of energy in the students entrepreneurs you meet? We're in a more complex world, yet...

Skip: Yes. The student entrepreneurs are at the other end of the spectrum from the "Spice of Lifers". They have tremendous energy, drive and passion for their ideas, even if they are not always business savvy. It is infectious. Its interesting that your friend Rajesh is an MBA student. I've found that many of these sorts of entrepreneurs are in business school (or recent grads). That usually translates into a good understanding of business trends and a solid basis in some fundamentals. However, a lot of times the practical business wisdom that comes with gray hair is missing. For example, I remember a bright young entrepreneur I worked with a few years ago. He had a business background from Wharton - and understood financials, the basics of marketing, etc. Yet he didn't know how to go about managing a sales person or how to close his first client. I was able to provide some of that experience and, I'm pleased to say, I spoke with him recently and he is completing his first round of venture financing after growing a successful online business.

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Thank you, Skip for sharing those stories with us. Skip specialized in artificial intelligence (AI) and natural language processing, two bodies of knowledge that we’re just now beginning to apply.

What kind of entrepreneur are you? To find out, take the poll at the Cheap Revolution, Skip’s blog for entrepreneurs who wish to use high value, low cost techniques to make the previously impossible a reality.