Tell Me About Your Entrepreneurial Journey

I’d like to know what you are doing, why you are doing it and how it is making a difference. Tell me about your Entrepreneurial Journey

I’m also interested in how your journey intercepts or synchronizes with what I’m doing; as chances are there is a “spark” for inspirational and engaging conversation between us.

Typical responses, when I ask this on Social Networks:journey

· I look forward to you being my lifelong mentor.

· Here are my new business ventures, please partner with me.

· Will you invest in my Startup.

Not so typical responses:

· “I see you are looking to solve this problem, design this or that… this is why I am…” A gold star for doing research and reading one or more of my profiles.

· “We seem to have a synergistic or complimentary path or journey… while you are doing that, I am doing this and therefore this is how we could work together to make a difference.”

What is the difference between the responses above?

The difference comes down to those who are “playing” at being an Entrepreneur and those who are “actually engaged” in an Entrepreneurial journey.

What actually is an Entrepreneur?

One of my favorite definitions is from 1983, and I quote HBS Professor Howard Stevenson, “Entrepreneurship is the pursuit of opportunity without regard to resources currently controlled.” More recently Stevenson told Eric Schurenberg for I N C “They (entrepreneurs) see an opportunity and don’t feel constrained from pursuing it because they lack resources, they’re used to making do without resources.”

You can design or innovate to the available resources, or you can find a way to make the resources available, which is mostly what Entrepreneurs do.

Three entrepreneurial journeys:

1.When I lived in Seattle, in the City proper, I played a game of musical chairs to accommodate my two cars in one mini-sized parking space ~ to solve this I rented another space in another building five blocks away. What a serious pain, when we only needed wheels once or twice a month… if only we could magically have had wheels when we actually needed them…. Right after that zipcar was born; I had nothing to do with the startup other than have the problem/pain for which the available zipcar resource was created.

2.There were two significant things I had noticed for sometime, but it took just the right entrepreneurial mindset to link them together, add the timing ingredient, and come up with a winner. As long as 30 years ago I noticed in Europe and in Sydney Nova Scotia locals opening their guest rooms for a fee (to make extra income) during busy holiday seasons or local events. I also noticed with the increasing high cost of both high-end and mainstream hotels many people were locked out of travel, unless they were camping enthusiasts. Solve both these in one Startup and you have airbnb. The homeowner with the empty guestroom has additional income and the traveller has an affordable place to stay; two widely spaced but readily available resources facilitated by a powerful online network.

3.Small business owners that I help have over the years complained about the difficulty of managing payment from customers; especially as we have morphed into a cashless society. Taking checks is risky and credit cards are expensive and time consuming to manage. Enter Square, a simple device & support infrastructure (run it on an iPad, iPhone or similar) which solves most of the hassle a small business has in implementing payment, especially where small transactions are the nature of their business! Having a simple payment infrastructure, which allows something as basic as the iPad to replace the expensive and cumbersome cash machines of the past, is a resource many small businesses are embracing today.

An entrepreneurial journey does not have to be as grand or large in scope as the three above, and many are not, but the entrepreneurial spin has to be there when I say “tell me about your Entrepreneurial Journey”

CASUDI aka Caroline Di Diego
Caroline Di Diego aka CASUDI is a Social Media whisperer helping Brands, Communities and individuals find their social voice. She is the creator of the successful Entrepreneurs Questions blog; an effective self-help resource for Entrepreneurs. She is an award winning documentary film-maker, using New-Media to tell people's stories with impact. Esse Group, boutique consultancy has been helping companies move from concept/chaos to fundable and or profitable for over 25 years. INCLINEDESIGN focuses on Architectural Design solutions. She is a Co-Founder of the non-profit BankOnRain, solving the global water crisis with an available resource, THINK RAIN! . She is an avid guest blogger
CASUDI aka Caroline Di Diego
CASUDI aka Caroline Di Diego




  • May 1, 2014


    CASUDI ~ You know that I am NOT an entrepreneur (I would hate to be anything so difficult to spell every time!LOL), but these lessons and insights I learn from listening and researching what you (and others) share, have helped me to become more. A better leader, manager, learner (yes!) and even, IMO, person. 
    It seems to me what you are saying is an Entrepreneur is really someone who has passion! A passion that will not be held back or down by an apparent or real lack of any resource, but will find a way.
    Ha! Thank you.

  • May 2, 2014


    AlaskaChickBlog Every time you go out into the wilderness and something unexpected happens and you need to find a resource to solve a problem, be resourceful …. you are embracing an entrepreneurial mindset. A great Leader had a good dose on Entrepreneurial DNA  in them…..

  • May 2, 2014


    CASUDI~ LOL, I was actually still thinking about all I have learned from you (and others) and the lessons, posts, self checks; this morning. It is ironic you replied with the words you did- BE Fearless, our focus, my own focus for the year ~ ALSO makes me think of this ~ #bealeader, could I have found more clearly what I was searching for? It all leads to Leadership. But not only that. It all leads to Great Leadership. For us all. To help us break the boundaries- “from where we are at right now” to know that “we are ALL leaders”. ~Thank you CASUDI (all) for all you have taught me, reminded me, shown me during this long journey.