I Was Born this Way. Asking Entrepreneurs: Were you?

I grew up in a family of staunch adherents to the traditional path:

1. Survive adolescence
2. Go to University
3. Walk into an office
4. Walk out 25 years later with a pension and a watch
5. Retire, travel, putz in the garden, take your meds

Some people, like me, made it to the threshold of #3 but stopped at the door, turned around, and walked off. Into the unknown.

As I meander through the Social Media landscape, I notice that many people dub themselves serial entrepreneurs. I would define a typical entrepreneur as someone who gets a good idea, fires up a business, hunkers down and works at it till death do them part.

Serial entrepreneurs, on the other hand, get one great idea, fire it up, pass the responsibility on, and stalk the next big idea. Thinking in terms of serial killers, this would mean taking bigger risks each time and moving closer to the edge. What quells the fear of going too far and crashing & burning?

Do serial entrepreneurs have some Phoenix in their DNA?

Maybe so. Entrepreneurs take risks, defined here as “engaging in any activity with an uncertain outcome” (from Psychology Today). Certain factors or qualities indicate a predisposition to risk-taking; high IQ, ADHD, being tall (not making that up) …

Can we teach someone to be an entrepreneur or is one hard-wired? Cameron Herold presents significant insights in this video: Let’s Raise Kids to be Entrepreneurs. He shares his journey and the influence of nature v. nurture (watch for the “Bipolar: The CEO Disorder” list).

This post isn’t intended to be a dissertation on the psychology of risk.
I want to know what you think, as an entrepreneur.

Are you hard-wired; what was your first enterprise?
Are you not built that way but were taught or mentored by someone?
Were you presented with no other choice because you couldn’t find a job?

I’m really interested in hearing your entrepreneurial story. I hope you’ll share what prompted (or compelled) you to seek the road less traveled.

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21 Responses to I Was Born this Way. Asking Entrepreneurs: Were you?

  1. milaspage says:

    Tobey, firstly I loved your post. I also always find it very interesting to know what motivates people, how they got to where they are. The journey is always so amazing. The question you ask is one that I have given thought to quite often. I know many types of people in my RL social circles, have watched various friends grow up through childhood, seen many personalities, and it always fascinates me. My answer to your question, as an entrepreneur, is I think it may be learned or sparked somehow, but I think it is something that happens early on. I truly believe the signs and actions of a motivated leader, thinker, “do-er” are present from a very young age – perhaps 8-10. Those kids running the lemonade stands, taking charge of projects at school… You get the idea.

    My own experience and answer, its part of who I am. I see something then the ideas start flying. My earliest example – when I was about 8, I read a great deal, one month, the book club selection included a book that had a whole listing of where kids can get “free stuff”. I thought it was very cool, it showed how to write professional letter to request the items, then gave information on the items so you could know what you would want. Some people may have been happy to receive the items free, and walk away with the toy itself, or the map , or poster (whatever it may have been) – not me, once I placed many orders and saw the items come in, I thought wow, this is cool. I wants other people to have this stuff too. I figured out I could write the letters for my friends. It wasn’t enough to just do that, because it occurred to me there may be cost, so somehow I came up with this idea of a girls club. (This part I do not even remember doing, later in life old friends retold me the story of how I set it up) – I started writing “professional letters” to my friends around the world (I have lived many places and always had many friends everywhere) – I called it a “Girls Club” and went on to describe that for membership of $1 I would then send monthly stuff (the free stuff). I even made membership cards, and I am told I did receive quite a few letters with $1 in it – my mother was curious/concerned as to what this was about, and only then did I explain it to her apparently.

    So, all this to say, I truly believe the entrepreneurial spirit is a gift, it is something that comes naturally. It allows us to see opportunities and create things, that perhaps others may not. My example of the girls club always amazes me because I truly do not remember the elaborate planning that went into it – it was just a “thing” I did, but when people who remember it, tell me about it, they always say – you’ve always been such a business minded person! ~Things we take for granted are perhaps our most natural behaviors. Natural behaviors lead to success and happiness in what we do.

    Thank you for your blog, as always, wonderful.

    • tobeydeys says:

      Mila – thank you so much for sharing this with us! I would contend that yours is a case of ‘nature’ if at eight you formulated a strategy to recognize and expand upon an existing opportunity. Additionally, you recognized the power of ‘inclusion’ by creating a ‘girl’s club’.

      “I truly believe the entrepreneurial spirit is a gift” <- I love this. I do think that not everyone has, or needs to have, this spirit because we do need the 'traditional path' people.

      Thank you so much – I'm so impressed with your adventure ๐Ÿ™‚

  2. Boomergirl says:

    Interesting post. Are you a serial entrepreneur?
    I don’t know if you have to hard wired but I think passion plays a role. I know that loving what I do has been key.

    • tobeydeys says:

      I think I might be ๐Ÿ™‚

      You’re right that passion plays an huge role; I’ve found (and still do) that if I don’t truly believe in a project then I have real fear that it will fail. It’s tough to fake faith – and certainly makes for a life not well lived!

      Thank you so much for reading and for your comment!

  3. Great question Tobey. I have some serial entrepreneur friends that continuously get back into the startup game trying to do it bigger, better and faster. It may not be in their DNA, but it is certainly expected of them within our peer group.
    For me, I founded one Company after spending 10 years working as an engineer in high-tech. At the time (dot-com bubble 15 years ago) , it just seemed like the right thing to do. I have always had the two traits of (1) being able to make things happen through sheer will and determination, and (2) being comfortable with a high level of risk and uncertainty. I believe that these two qualities are essential for any entrepreneur.

    • tobeydeys says:

      Hey Christopher – thank you for your insight.

      I might suggest that your (2) point may rank as (1)! Without the comfort around risk and uncertainty, no one would take a leap into entrepreneurship. Determination behooves all enterprise – whether one is digging trenches or single-handedly building an empire.

  4. mack collier says:

    Hi Tobey, great post and interesting thoughts. For me, I think the most accurate option would be that I was presented with no other choice cause I couldn’t find a job. To give you a bit of background, I live in a very rural area of the South, and due to several reasons I don’t want to get into here, I need to stay in this area of the state. By the end of 2003 I had just earned my BBA and MBA, and the massive student loan debt that went along with it. That was when I began looking for a job, and realized a very unsettlingly truth about job-hunting in rural Alabama; Having an MBA on my resume was actually keeping me from getting hired. I learned this the hard way when employers informed me that I needed to take the MBA off my resume, that employers were assuming ‘that you want too much money, and that you will use this job as a stepping stone to get out of state as soon as you can’.

    Soooooo….after the realization that I had just accrued thousands upon thousands of dollars for an MBA that was actually worthless to me in my particular job market, I decided to switch gears a bit. I was still looking for a ‘good’ job in 2005, when I started learning about blogs, and social media. I decided that getting some experience blogging and understanding social media could only help my chances of getting a job, so in the Fall of 2005, I was invited to join the group blog Beyond Madison Avenue. I took to blogging like a fish to water, and within a few weeks I was ‘promoted’ to editor of the blog, and it went from 0 visitors a day, to 2,000. In March of 2006, I decided to launch my own marketing blog, The Viral Garden. Still looking for my ‘real’ job the whole time. Then later that year I started getting paid writing opportunities, and a few consultant friends started pulling me in to help them on projects. Or 2007 this increased, a few more writing assignments, a few more consulting projects here and there.

    By early 2008, I started getting paid speaking gigs, which, along with the increase in writing and consulting work (and the ever-present lackluster Alabama job market) made it an easy choice to start consulting full-time. So my working for myself was borne out of necessity as much as anything else. Interested to read what others say motivated them.

    • tobeydeys says:

      Hello Mack,

      I love how you say that you were looking for your ‘real job’; it seems to me that your ‘real job’ found you. ๐Ÿ™‚
      Help from friends and guidance from mentors is so critical to building confidence in staying the course when we’re not sure that we’re even on the right path. (I know your wisdom and support are invaluable to me; I wouldn’t be writing this right now if not for you ;-))

      Mack, thank you so much for sharing your story with such candor. I’m honoured to have you as my mentor and, most importantly, as my friend.

  5. Dan Perez says:

    I was the second oldest of 7 kids. I grew up in the Bronx and lived there until I was in my late 20’s. My father worked in a factory and my mom stayed home taking care of us. My parents wish was that we not end up on drugs, in jail or dead (all of which I barely managed to avoid). I found myself at 27 having worked a dead-end job at the New York Public Library for the past 9 years.

    Upon meeting the person who would ultimately become my wife, I began to aspire to greater things and a new career. I interviewed for a sales job with Prudential selling life insurance (my sister had to lend me $200 for a suit, shirt, tie & shoes) and got the job. I soon realized, however, that being popular in the neighborhood and having the proverbial gift of gab didn’t translate to success in sales.

    As I networked in the various business groups in the Bronx, I met Daniel Garcia who was CEO of Salsa Caterers. He saw something in me and offered me a job in corporate catering sales. Though we were about the same age, he became my first mentor. He taught me about being a professional, listening, and consulting. He also introduced me to Brian Tracy, Zig Ziglar, & Tony Robbins. I started listening to audio tapes in my car and within four months I was out-selling the other 4 salespeople combined.

    After getting married and moving to Long Island, I left Salsa Caterers after 2+ years and took a Sales Manager position at a 60k square foot entertainment center close to home. After 3 years there, I relocated my family to South Florida where I was offered a Director of Sales & Marketing position at another family entertainment center. Bought a nice house and making the kind of money I only dreamed about; the Bronx kid had done good.

    It was during this time, that I started dabbling in video editing. It started when I re-edited my wedding video footage and soon I was creating short family music videos. I thought my work was pretty good but never thought I could make a career out of it. During a networking event one day, I met a fellow who owned a video production company. I told him I did some small video productions and he asked to see my work. I sent him a few samples of the stuff I’d done and a few weeks later, I got a call from him. He said he was blown away by my work(!) and wanted me to videotape his wedding in a few months(!!!). This was when I realized I had, what they call in the Bronx, “skillz”.

    Suddenly, the career I was very very good at and that I once loved became an afterthought. I wanted to pursue a career in video production; start my own business. I had sat on committees on several Chambers of Commerce, was a Board Member at several non-profit organizations; I had the network to do it. My wife had to talk me out of quitting almost every week. I promised her I’d be making money in just a few months. Then the best thing that could have happened happened. I ended up getting fired (mentally, I had already been gone for several months and my sales numbers reflected that). Now, I was finally able to take over the world of video production and make the really big bucks I promised my wife!

    A year and a half later, I’d made about $15k. It didn’t exactly work out as I had planned but the business was always creeping up ever so slightly; enough, at least, to keep me going forward. Thank God I married a patient woman!

    I had taken some temporary consulting jobs with a few non-profit organizations during those early years to make up some of our lost income but in 2008 I dedicated myself to just the business. Over the next three years, I’ve seen the business grow by close to 30% a year. During that time, I produced & directed two documentary films that went on to win major awards at film festivals (and award-winning filmmakers can charge more for their work, yes?). This year, the company has already made over half of what we earned last year and I’m working on my third documentary film.

    Was I hard-wired? No, I was destined for an unremarkable life but God had other plans for me. I’ve learned to just sit in the back seat and let Him do the driving.

    I had a mentor. Several of them, in fact.

    I had another choice: stick with my job and the security it provided my family. I chose to pursue my new found passion. Why? So that I can look my daughter in the eye and tell her not to be afraid to go after what you love (and have actually done it myself). You can always get a job.


    • tobeydeys says:

      Dan – what an awesome journey! I could not agree more ardently with listening to the whispers from your soul and your Guide and trusting. I think it takes a lot of courage to do this especially when stable and secure alternatives are staring you in the face.

      Thank you for sharing, Dan. Your story is an inspiration that the road less traveled doesn’t have to be dark and scary (especially when you let Someone else do the driving ๐Ÿ™‚ ) You are such an awesome friend and have been so wonderful supporting me as I stumble along finding my way!

      Huge Hug.

  6. Dan Perez says:

    DANG!!! Did I just write all this???

  7. Ken Lingad says:

    I don’t believe that DNA or “hard wiring”/pre-destined-for-success scenarios are catalysts for entrepreneurial pursuits. Growing up in two minority demographics – Native American and “dirt poor” – there were no positive role models or mentors within any reasonable proximity to my little corner of the Indian reservation; however, my mother did everything she could to expose me to a variety of experiences in the “white” world: dance lessons, musical theatre, fine arts, etc.

    Seeing how the world off the reservation revolved, it never occurred to me that I couldn’t do anything I set out to accomplish – despite our financial situation. I have encountered almost every form of discrimination one can be saddled with: ethnic, appearance (I’ve worn my hair long since I was a boy), gender, and class. That is one of the reasons I am an entrepreneur: I am the captain of my own ship. I answer to no one.

    What set me on my current path of entrepreneurial endeavors (I have several), is the wish to use the gifts of my business acumen to benefit myself and those I am associated with, as opposed to always building successful projects for every entity from hi-profile personalities, public and private groups, and non-profits to state/federal government interests only to get shut out or cut after my time and resources were drained from me. I had grown weary from making others look good and be successful, and decided it was time to focus on doing things for me and “mine.”

    The traits I believe identify me as an entrepreneur are the following:
    1. Do what it takes to finish a project
    2. Willingness to go “all in” when I decide to do something. I am not afraid to jump without hesitation. I never blink.
    3. I am not daunted by the unknown. I embrace opportunities to learn what I can. I make it my business to know what I need to know about every aspect of my pursuits, but am quite comfortable seeking guidance or tutelage when necessary.

    I have also been dabbling in the particular studies regarding behavioral finance, specifically Prospect Theory. I find parallels between what drives financial risk-takers such as gamblers, and some walks of entrepreneurs – two groups that tend to display similar “irrational behaviors.” I note this because losses and gains seem to have more of an emotional impact for these groups than what we accept as “traditional” ways of thinking. I believe this is a key component to identify when discussing what “makes” or “drives” an entrepreneur.

    In my case, ego contributes to my success in some positive ways. Knowing that I possess the skills and acumen to do what I do better than those I’ve worked under in the past remains the sole catalyst for anything I put myself to now. And if I can’t do what I set out to better than my competitors, I surround myself with talent that can.

    Ken Lingad – 1680PR / 1680, LLC

    • tobeydeys says:

      Ken, my dear friend, what a powerful comment – thank you!
      By accident of birth, I have never had to endure discrimination of any kind so I couldn’t say with any confidence that I can relate. Such adversity could prove to crush even the strongest resolve to succeed.

      I would hazard the thought that, on some level, you are ‘wired’ for entrepreneurship – that you have vision beyond the present and the strength of character and purpose. I love that you also possess an altruism to share your success with those close to you; I know that you engender great confidence and trust from your team.

      You (insert you know what here) rock! Thank you so much for your generosity – for sharing this insight into your continuing journey. Deepest Gratitude.

  8. Luke Davis says:

    I agree w/Ken about not being hard-wired… But I do feel strongly that those folks who are inherently ‘risk averse’ will not get there.

    My first enterprise was founded when I was 10 years old in bad hood in Oak Cliff, TX. I couldn’t spell ‘entrepreneur’ let alone know what it meant; it’s founding wasn’t out of some crazy drive to drive flashy cars when I grew up or even compete with the neighbor-kid’s lemonade stand.

    I would have loved that though. That’s what kids should care about (lemonade stands, and the like). My first ‘venture’ was a courier service and desktop publishing biz that also distributed the wares that we published.

    It sounds more advanced for a 10-year-old than it really was: we found a need among mom-and-pop business owners strip-mall where the Kroger grocery store was. They need errands done, foo brought to them at lunch, and flyers made and put on car windshields in the parking lot to drive traffic.

    I was the youngest of 5 kids growing up with our single mom an we were broke. This wasn’t the great adventure I feel entrepreneurship is for me today, it was what paid for our PB&J sandwiches.

    That said, I did make it to step #3 and did walk in the office after university…. I became a military officer and enjoyed every moment. But there was always an intense drive to innovate and discover real problems that needs solutions. Even better when you get there before the other guy.

    I was already acclimated to risk-taking when I decided to join my first ‘full-blown’ start-up after grad school. That startup was fast, fun, and a terrible failure. I learned lot working there–especially from the mistakes that the founders (and employees including myself) made. This didn’t squelch my intense desire to head down this path–it merely field the flames.

    As much as I’d like to believe my case is unique, I find that many folks are conditioned in life to follow similar paths if the right catalysts are present.

    So, is it inate? I don’t think so, but I do believe there are factors that drive peoples’ risk aversion.

    Are we built this way? Possibly–if by ‘built’ we mean the bricks that get stacked as we grow and develop character.

    Is it somehing that can be taught in a classroom? I’ve never seen it, but I can’t say it couldn’t be done. However, I’m more incline to feel it could be better learned in a psych/sociology discipline rather than the biz school route I took.

    Last, I apologize fo horrible gramm/syntax/typos/etc…. This was type on A lame iPhone keyboard that really sinks (sorry apple, but lame)

    • tobeydeys says:

      Hey Luke – first off, I’ll forgive any iPhone-caused errors. With fingers like canoe paddles, I feel ya’.

      “That startup was fast, fun, and a terrible failure. I learned lot … This didnโ€™t squelch my intense desire to head down this pathโ€“it merely field the flames.” Love this! Failing brilliantly has also driven me to find a better answer, a new direction – take what worked, learn from what didn’t, and rebuild. (Phoenix-esque perhaps? ;-))

      As Mack said, necessity often drives entrepreneurship. Given your propensity (at ten years old!) to discover and drive solutions, I sense that you are a born innovator. I think that innovators can settle comfortably within a traditional structure if given the opportunity to ‘fail & solve’ but would wither with nothing to solve.

      Thank you so much, Luke, for so openly sharing your story with us ๐Ÿ™‚ I’m humbled by your generosity.


  9. Dino Dogan says:

    Looking at everyones long answers I fear (hehe) that mine will fall short ๐Ÿ™‚ But here goes…

    I think Entrepreneurs are in fact made. At least I was. I certainly didnt grow up an Entrepreneurs and I wasnt taught to be one either. Not by my parents, not by my teachers, not by anyone else I knew personally.

    It took a lot of self directed learning to have the balls to do it. And my first real venture into Entrepreneurship was a miserable failure that took me over 2 years and over 40K to fail…how is that for painful.

    But, I’ve learned from it and now run much leaner and smarter. Money is no substitute for resourcefulness.

    Hope all this makes sense…great question, great post. Good work Tobey ๐Ÿ™‚

  10. I been writing this for days but we have talked about it so I am just letting you know how amazing I think you are and that I love your writing.
    you are my dictionary, rock of gibralter and so much more!

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