Tag Archives: Broke CEO

How I Left Corporate – Part III

Fighting foot traffic to get to the office? Not anymore!

Fighting foot traffic to get to the office? Not anymore!

If your just joining me for the final installment, let me do a quick recap of what you’ve missed.  In Part I I talked about what sparked my desire to leave, how I came across my road map and what my backup plan entailed.  In Part II I spoke on some of the intricacies of that plan and how it went from ideation to implementation.  In this post I’ll give you all the minutia of how I executed the plan and how that has played out over time.

A Day In The New Life
January 16, 2012 marked my first day heading up operations full time. In my 2012 post A Day In The Life of A Small Business CEO I speak about what that life looks like.  Four years later, daycare drop offs have been replaced with school, but the routine is still mostly the same.  Needless to say, I love what I do and I really don’t see it as work.  Our site/blog has numerous post on having passion about what you do, how to deal with fear and how manage through growth.  But the key takeaway that I would like to share about my new life is that it’s a fit for me and who I am.

Not everyone is “built for this” as I like to say, and rightly so.  Personally, I think you have to be a little bit “off” in order to strike out on your own or head up your own business.  However, if you do so, make sure that you are doing it for the right reasons.  In the 2013 post Why You Shouldn’t Become An Entrepreneur we talk about the 5 reasons you should NOT jump into this lifestyle.

Working The Bridge Plan

Can I come back as a contractor?

Can I come back as a contractor?

As I mentioned, my bridge plan was to work as a contractor via an agency.  So, when I was getting ready to leave corporate, I reached out to many of the placement agencies that I had used to get full time positions and asked them if they had a contract division.  Some of them did and some didn’t.  Needless to say, one agency found my resume in April of 2012 and got me placed on a 6 month contract.  This allowed me to pay my bills and still work on the business, which of course was in a slow period since it’s seasonal.

Now, contract work was originally only supposed to be a two year thing.  However, I found myself financially in a position where I needed to do it again in year 3 due to a lot of unexpected incidents (e.g. broken collar bone in a bike accident, car repairs, medical expenses, etc).  In year 4, I was able to reduce my schedule slightly (e.g. 2 days a week versus 5 days) and in a few weeks I will be in the business 100% (hopefully permanently but you never know).

The key point of the bridge is that it 1) is designed to tide you over until the business can support you and 2) it should also serve a purpose outside of financial motives.  What I mean by the latter is that it should enhance your skills, give you exposure to new things (e.g. industries, markets, etc), provide additional training for your new life or at a bare minimum, maintain your skills so that you can continue to be marketable.

My contract assignments kept my skills sharp as I essentially worked in the FP&A department of two different companies in two separate industries.  This essentially extended my corporate FP&A career by an additional 4 years.  It also allowed me to see how different industries worked (e.g. energy and heavy durable goods) as well as work with new teams of highly talented people.

Watching The Company Grow
Looking back at 2012 and where we’re at the end of 2015 makes my head spin.  I remember how mad I was at the end of 2012.  The short version of it was that the company performance was far off from our initial projections and I couldn’t figure out how or why.  But I quickly trained myself to focus on the mantra “the only thing I can control on a daily basis is my attempt to go out and find sales.”

Subsequent to that year I would go on to work with Intuit as an Ask A Tax Expert and in their Personal Pro product due to the acquisition of a platform I was participating in.  Our client base would grow by double digits in each of the years from 2012 thru 2015.  We got picked up by some pretty sizable companies to handle their finance function.  And somehow in the midst of all this we launched a secondary web site to help folks file all of those old tax returns!

While we’re now at the point where things are starting to stabilize, I have to reiterate that it wasn’t easy.  That “not easy” part is outlined pretty well in the post Do You Really Have What It Takes To Start A Business.  Thus I would encourage you to read it if you have some time.  But in summary, if you are looking on the “how” to leave Corporate America piece, it involves:

  • Identifying what your second or new life will look like
  • Outlining how you can bridge your current and new life
  • Developing that bridge plan
  • Implementing and working that bridge as your new life takes shape
  • Adjusting and remaining fluid until you arrive at your destination

I hope that you have gotten something out of these posts.  Going from corporate to CEO took me many years.  I had to learn and work through lots of lessons, some of which I had no direct mentoring on.  But if you have the desire to make the change and the heart/drive to learn and then try new things, I am pretty confident that you can achieve the success you desire.

Best of luck in your endeavors and here is to a prosperous 2016!

Mr. Jared R. Rogers, CPA
President & CEO
Wilson Rogers & Company, Inc.

Why You Shouldn’t Become An Entreprenuer


Many of us dream of having our own company or at least working for ourselves.  Let’s face it, how liberating would it be to not have to report to the “man” day in and day out?  Well, while that might sound all fine and dandy, it’s quite another thing in practice.  We’re in the fortunate business that we get to counsel many aspiring entrepreneurs before they take the big leap.  Our advice?  Simple; don’t do it.  Well, don’t do it for the wrong reasons at least.

Outlined below are five reasons you should NOT become an entrepreneur; which account for 90% of the reasons people want to become one.  However, we then follow this up with five reasons you should take the plunge.  Ready?  Let’s get started.

Reasons against becoming an entrepreneur

You want to be rich. Going into business because you want to make loads of money is just a bad idea.  Truth be told, making money on your own is an extremely hard and volatile venture.  And if you think it’s a good return on investment, that’s just bad math.  Most businesses fail within a few years and those that do make it often take years to become profitable.  Plus, for the first few years don’t expect to take a check.  Total up all of the above and the phrases “starving artist” and “struggling musician” start to make sense.  So if you’re motivated by money, you’re far better off being a banker, investor or consultant or something.

You hate your boss. If you think that getting rid of your boss frees you up from having to report to anyone, think again.  Every CEO of a major company still has a boss.  They are called the Board of Directors, shareholders and customers.  So when you become the CEO, all you really do is just trade one boss for thousands more (e.g. customers).  And guess what?  Customers are some pretty demanding folk.

You want to work less.  People often tell us that they want to work for themselves because they want to spend more time with their kids or family.  Okay.  Unfortunately that’s not how it works.  In reality you will get “flex time” but in the form of you picking any 24 hours of the day to work your tail off.  Over time a successful entrepreneur may work less than they did in Corporate America, but this often takes many years to accomplish.  In the beginning, you will be responsible for making everything happen.

You like the idea of control. Some individuals are enamored with power.  Titles, money, expensive toys etc. exemplify this for these individuals.  What it’s really like: everyone else is your boss – all of your employees, customers, partners, users, media are your boss.   On top of that, there is very little control in a business.  Things are constantly happening and needing to be addressed.  What’s worse is that if you’re one who likes predictability, you will soon find yourself pulling your hair out.  Entrepreneurship is far from predictable.

You want to get rid of the stress of corporate life.  Sure, reporting to a demanding boss is stressful.  So is figuring out how your going to negotiate a line of credit to keep the company open 20 more weeks while you wait on that Federal Government vendor payment to come in.  The reality is that we make our own stresses and they follow us.  Building a business is cool but it involves a lot of work.  So if you’re trying to escape for stress reasons, you may want to reconsider.

Okay, so now that we’ve got that covered, why should you take the plunge to head up your own endeavor?  Follow us please.

Reasons for becoming an entrepreneur

You’ve identified an unfulfilled market space.  Most ideas that come to market tend to be slight modifications of existing concepts.  This is not to say that we don’t derive benefit from what they provide, it’s just that it’s not earth shattering (e.g. ATMs vs. a personal banker).  However, if you have figured out a new concept that isn’t being used by your competitors and can truly cause a paradigm shift, therein lies a market opportunity (think Segway).  And where opportunity and demand intersect, money is often made.

You are passionate about something.  A good friend of ours always says that you shouldn’t go to college to major in what you love, but what you can find a job in.  While that is good financial advice, it’s not the best advice for those seeking to run their own show.  You see, we’re big believers that passion carries a lot of weight and can take you places that “doing a good job” simply can’t.

Take Tony Robbins for example.  While many will say that Tony isn’t extremely talented and he didn’t go to college, few will argue that he hasn’t made himself a household name.  How did he do it?  By taking the bull by the horns so to speak and forging his own way.  That takes a lot of guts giving how hard this entrepreneurship journey tends to be.  But if you have passion, good things tend to follow; which is typically a result of how hard you are willing to work and the lengths which you are will to strive to make your dream a reality.

You’ve figured out a better way to do something. Capitalistic societies are cool in the sense that if you have an idea that can improve life in some fashion, you can probably do well financially.  Thus, if you have a concept or product that will truly change the way things are done (e.g. powering cars off water vs. gasoline); you should by all means go for it.

You want to make a difference in society.  This world is full of individuals and companies that just want to make a quick buck.  The ones that are truly great are those that want to make things better.  Back in the day Ben & Jerry’s was one of the pioneers of the now common “Corporate Responsibility” movement.  But some companies such as One Laptop Per Child (see them in this article) take it a step further in trying to improve situations, people, socioeconomic groups and the like.  So if you are trying to make things better and you can make a little coin in the process, by all means be our guest.

You just can’t live your life any other way.  Sometimes you will hear people say that they weren’t meant to go to college, or work inside an office, or work for someone else.  If you truly thrive in working in an entrepreneurial environment, then it’s probably best that you become one.  Yet, the keyword here is thrive.  Whenever you find a situation that lets you be the best that you can be, you should embrace it.  Whether it’s your job, hobbies or love interest; when you find something that fits perfectly, don’t attempt to resist it.  Often times, you will regret it if you do.

"Do what you love. The money will follow!"

“Do what you love. The money will follow!”