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Entrepreneurs Enjoy Independence and Rewards

Entrepreneurs Enjoy Independence and RewardsI have always been fascinated by entrepreneurs. And it’s not just the high-profile internet darlings that capture my attention. I am equally enamored with the small local business owner. It’s the act of creating something out of nothing. Seeing a future that others don’t. Taking an idea and turning it into a self-sufficient business that makes money. The entrepreneur has peaked my interest for as long as I can remember.

Over the years, I have encountered my share of entrepreneurs. When I was handling healthcare acquisitions, I spent all my time meeting with business owners, evaluating their companies, and trying to buy them. I have worked for closely-held companies started by the company owner. Also, I have family members who have owned their own businesses.

And after spending so much time in their presence, I really don’t think there is a “typical” entrepreneur. Some were hands-on, others remote. Some had started the company in an industry they knew well, others were in completely new territory.

The only commonality among the entrepreneurs was that they owned their business and that was how they made a living.


How Many Entrepreneurs Do You Know?

The other day, I started making a list of the people I know and what they do for a living. The initial question I was trying to answer that motivated me to start the list was,


How many entrepreneurs do I know who have started successful companies?


For purposes of this exercise, I defined a successful company simply as one that provides enough money for the owner to live off without working a “regular” job.

I limited my pool of people to those I actually knew. That excluded many LinkedIn connections, Facebook friends, and fellow bloggers. Essentially, the list included family members, people I know on a personal level, and people who I know professionally. There are a few that cross multiple categories, but not many. That is probably because during most of my tenure living here, I have primarily worked with out-of-state companies and individuals. So my business world and personal world haven’t overlapped much.

As I put the list together, I started to see patterns and organized everyone into one of three categories:

(1) Those who work for a company that they didn’t start or own,
(2) Those who work for their own business providing a professional service of some sort (doctors, lawyers, accountants, financial planners, consultants, insurance agents, etc.), and
(3) Those who work for their own company which is not in a professional service.


Why Do People Choose to be Employees Rather Than Entrepreneurs?

Not surprisingly, most of the people I know professionally work for a company or business they didn’t start themselves. Most of them work for a large corporation. There were a few here and there who had started businesses, but mostly these were not much more than extended consulting stints in between corporate jobs. This wasn’t surprising in that I have worked for over 20 years in the corporate world, so it would make sense that most of my professional contacts are also in that space.

While most of the people I know professionally work for big companies, most of the people I know on a more personal level (especially those that live nearby) do not. There are a few teachers in the group, and more than a few people working for the government or a government contractor, but the majority own a business providing professional services. Again, these are doctors, lawyers, accountants, financial planners, etc.

And very few of the people I know started the company they work for. This may say more about the local economy than anything else, but it is interesting.


One Year Anniversary

So why am I asking this question?

Besides my natural curiosity about entrepreneurs and how they decide to start new companies, I’ve started thinking about what I want to do.

I’m coming up on one year removed from the corporate world. And while I have enjoyed the flexibility and independence, as I’ve said before there are some aspects of the working world that I miss. I have missed a consistent income stream, but I have also been able to replace that with private finance consulting. As an independent contractor, I can make more per hour than I could as an employee. It’s just a question about how many hours I can work.

But separate from money, the other thing I miss about the corporate world is the interaction with a team. As a consultant, you will typically engage with other team members, but it’s usually short-term. It doesn’t have the same feel as working with a group to grow a business.

In my last role, I oversaw 150 or more employees. I had daily conference calls with my team and my peers. I regularly met with clients, vendors, and partners. Everyday, I faced a new challenge. And I must say, that at times, I do miss that heightened level of activity.


What’s Next?

So as I said, I’ve started to consider options.

Grow my consulting business. The first option is to grow my consulting business. There is a potential opportunity to partner with another company thereby providing access to additional resources. As I’ve indicated in prior posts, I enjoy consulting. But the challenge with consulting is that it’s a local business. Selling new business and providing consulting services often requires significant face-to-face interaction. As such, to grow the consulting business will require travel. I am no stranger to business travel, but I need to decide if I’m willing to again spend significant time away from my family to grow and manage the business.

Invest in another business. In addition to consulting, I have a few other business ventures up and running. I could invest additional time and capital into growing one of these businesses. Alternatively, there are other businesses that I could start or buy into. Similar to the challenges consulting in the local market, to be successful a business will need to draw clients from outside the area. The good news is that unlike a consulting business, the other ventures can take advantage of the leverage provided by the internet and sell into multiple markets.

Find another corporate job. My last option would be to find another job and reenter the corporate world. Over the past few years, the healthcare industry has experienced many challenges. Some of the challenges are driven by external factors and government intervention. Others are self-induced. But as the cost of healthcare continues to rise, I expect there to be a need for people experienced in dealing with these issues. The obvious disadvantage of finding another job is giving up the freedom and independence that I now enjoy.

Readers, I would be interested to hear your thoughts regarding the above options or even something I haven’t considered.



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  1. Martin - Get FIRE'd asap

    Hey there FS. That’s a great idea, throwing it out to the community for feedback and suggestions. I’m guessing you have thought long and hard about what to do and it’s left you in a bit of a quandary.

    For what it’s worth, and since I have also been in your position a few years back, I suggest taking a bit of options 1 and 2. However, that depends on whether you want to spend the time and effort building up another business or not. This can be very time and energy consuming as I’m sure you know. And do you really want to do that. As you say, do you want to spend more time apart from your family?

    Another option would be to offer your services to another, larger company or companies.

    Continue growing your own business and developing your own clientele, but also work in with other companies, perhaps on a contract basis.

    That means that you can still maintain control of your own destiny (very Obi Wan) with your company, but have the benefits of regular work and the team environment working with the other companies.

    In addition, you will probably learn ways to improve your own business from their experience.

    Option 3 should remain just out of reach unless absolutely necessary but as I’m sure you can attest, once you’ve worked for yourself, it’s very hard to go and take orders from another employer.

    Just my humble thoughts and opinion.

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    1. Financial Slacker

      Thanks for your feedback, Martin.

      I do think offering my services through a larger company is a good idea. There is another consulting firm I know that might be a good fit. It’s definitely something to consider.

      View Comment
  2. Vicki@Make Smarter Decisions

    Great points about entrepreneurs and I agree – they all do things in different ways! I understand your point about being part of a team – and missing that. I worked in schools for almost 30 years and you were always with people (and on too many teams and committees at times) – and although I don’t miss a lot of that work, I do miss the people. I am going to look into other ways to get involved in groups – doing things like volunteering for specific events. That would allow me some focused efforts but still allow for travel and my own projects too.

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    1. Financial Slacker

      Thanks, Vicki.

      I have thought about volunteer activities. And I’ve served on not-for-profit boards in the past.

      That might very well be a good way to get what I’m looking for and give back to the community at the same time.

      Thanks for your thoughts.

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  3. zeejaythorne

    My LLC work is just me at the office, but I have a core group of people (besides my clients) whom I interact with on a near daily basis. We also do at least a monthly dinner as a group. Many of us have our own small businesses, but some do the work in bigger organizations. It really helps to feel like I have colleagues, but I don’t have to travel for that, which matters a great deal to my time and happiness level. If you miss being in charge of over 100 people, it may be time to work for a corporation again. There’s nothing else quite like that.

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    1. Financial Slacker

      Thanks for the comment, ZJ.

      I really like the idea of a regular group dinner. In the past, when I have been part of a group, it’s always had another purpose. Usually a chapter in some business networking group. I’ve found those to be tedious.

      My father has owned his business for almost as long as I can remember and he participated in weekly lunches for most of that time. There’s a social aspect, and a business aspect, and a support aspect.

      Might be worthwhile to get something like that up and running.

      Thanks for the idea.

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  4. Chris @ Sleepy Capital

    I love the idea of investing in another business. Being able to leverage the internet to expand would be beneficial and perhaps require less travel time. You would also be able to leverage your consulting experience as an investor. Depending on the amount of your stake in the business, you may also be able to take more of a semi-passive role depending on your partners. This way you’ll have time to continue to develop your blog while still contributing a team to grow the business venture. Best of luck as you consider your options!

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    1. Financial Slacker

      Thanks, Chris.

      I agree that leveraging the internet might mean less travel. At least once something was up and running. It also expands the market exponentially. The small market is a nice testing ground to get something up and running and then once you’ve got a solid idea, use the internet to expand to a much larger market.

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  5. Finance Solver

    Entrepreneurship is hard. I’ve had the over-optimism bias for the longest time and I still do and as a result, results always turn out worse than what I expected (sometimes even losing money).

    Because I’ve been kicked to the curb multiple times, I just can’t take on that much risk to start a company from scratch without a safety net because it can fail because of something that’s beyond my control. I will never ever start a company by going all-in and quitting my job. I will start one on the side to see if it’ll pay off, however then I will consider quitting to start something. I learned my lesson to never let my ego get in the way of success.

    I commend you for having the courage to go away from a consistent paycheck schedule and try entrepreneurial pursuits.

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    1. Financial Slacker

      Thanks, Finance Solver.

      It’s a different decision when you have a steady job as opposed to not having one. In the past, when I had a corporate job, I tended to look at entrepreneurial opportunities in terms of how long it would take to replace my corporate salary. And it was always hard to make the numbers work. That usually kept me from jumping ship, although not always.

      Without a corporate job, when your income stream is less predictable, the entrepreneurial leap seems less daunting. This is even more so when the corporate job prospects aren’t appealing.

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  6. ambertreeleaves

    Nice post. It is exactly this kind of questions I imagine that pop up after FI.
    Although I am still working, I expect that going after 1 would be the best pick. You keep in control and can stop ate any time. The travel might not be fun. After a few face2face meetings, maybe skye can help? I did a few Skype meetings with my boss already. works fine!

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    1. Financial Slacker

      Thanks, ATL.

      I do think Skype can serve as a decent proxy replacing some face-to-face interaction. As a consultant, once you’ve built a relationship and as long as you have a certain level of periodic interaction, Skype should work.

      As a remote employee, it’s a little different. I still felt out of the loop quite often even with Skype. It’s the spur-of-the-moment discussions that are always happening. It’s the quick lunches to talk about something that just came up. These are the things you miss as a remote employee.

      But as a consultant, you may be able to function fine without.

      Thanks again.

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