Until recently, I’ve been the primary breadwinner in our family while Emily has been at home taking care of the four kids.  By the way…I’ll take what I was getting to do any day of the week over what she got to do!  Teamwork makes the dream work.  I’ve always taken my job/career very seriously.  This was mostly by necessity because providing a family of 6 all the niceties of the life they desire requires a steady stream of cash flowing in (and out…YIKES).

High School Jobs

I started working when I was 14 ½ for Mr. Trent at Ace Hardware in Springfield, TN.  Then, when I could drive, my friend Beau put me in line for one of the best jobs in towns.  Mr. Clinard, of Clinard Drugs, brought me in to help with the soda fountain, cleaning, drug deliveries, etc.  NWA had recently released their song ‘Dopeman’ so I thought I was especially cool delivering the little old ladies their ‘dope’ every afternoon after school while drinking a freshly prepared chocolate soda fountain milkshake.  I also kept Mr. Clinard’s cars spotless when not at work (and his friend’s cars too).  I was side giggin’ before anybody even knew that was a thing.  Try to keep up people!

Picking My Major

I originally went to college to study ministry and was going to a preacher (with a minor in accounting).  After several religion classes, I realized the world of religion was much larger than my limited Southern Baptist upbringing.  I didn’t feel like I was up to the task of convincing people what to believe when I barely knew anything (seemingly).  I had always enjoyed my accounting classes and was good at them in high school.  I dropped the religion part and kept the accounting.  But I didn’t think I really wanted to be an accountant.  So now I was in school without a real direction.  I didn’t really know what I wanted to do but I did know 1) I wanted to make money, and 2) I wanted to know what to do with it once I made it.  I switched my major to get a finance degree.  I figured whatever I wound up doing in life I could use the skills I’d learn there.

College Jobs

By the time I went to college in Nashville at Belmont I had started working at UPS on the night shift.  I’d go in at around 10 PM and get off around 2-5 AM.  My first position with UPS was loading trucks at their big sorting hub on Whites Creek Pike.  I worked there several years so I promoted up to the bigger, faster volume trucks, then up to bottom pickoff, then top pickoff (weak side), and then the pinnacle of my UPS career top pickoff (strong side).  There were discussions of moving on up the chain of command (and running my own belt) but I didn’t think that was what I wanted in life.  So, for me climbing that great big ladder and directing the flow of most packages for a bunch of trailers was it for me.

Now, that said, I didn’t have a lot of use for college.  I hated almost every second of it.  My main gripe was it required me to do a lot of work but didn’t pay me to do it (even worse they made us pay them).  I had bills to pay so I started valet parking while I was in school.  I’d valet park during lunch, go to classes in the afternoon and night, and then work at UPS at night.  It was a frantic pace and when something had to give it was always school.  I maintained this schedule most of my college life and I missed a lot of classes but did enough to make it through most of them with a GPA that was good enough to keep things moving along.  My mentality was, ‘give me my sheet of paper and let me go make some money’!


As the final semester of my junior year ended, I knew I needed to get some experience in the real world within the career path I was working towards.  I had no clue what to do or what steps to take next.  I went to my school’s business program office.  “I’d like to get an internship!”  They looked at me like I was from Mars.  Thanks for nothing!

At this point, I had started waiting tables.  I decided it was time for switch after almost driving off the road a few times late at night getting to/from UPS (falling asleep).  Also the valet company I was working for lost their clients and got shut down (very shady operation).  I met a lot of great people along the way while waiting tables (at a restaurant near school in Green Hills).  One night I waited on a young couple and this energetic man was telling me about his new company.  The book ‘The Firm’ by John Grisham had recently come out and I had read it under my desk in some stupid business class.  I loved the book.  The way Joe described his financial company it sounded just like The Firm.  He was doing investment performance reporting (hey…I was studying that) and it sounded like there was a lot of mahogany involved (just like in The Firm).  I would work for Joe!  I pulled his name off his credit card, looked him up, and started calling his house.  His wife grew tired of me calling very quickly and told him to talk to me, so I’d quit calling her.  This is called stalking or is it harassment?!?  Regardless, it worked.  I met with Joe one day and told him I’d work for him for free and would help out with anything I could.  After many years of working for Joe I now know that he likes anything free so I got the ‘internship’.  When I started there was, in fact, no mahogany.  There was a one-room office in the basement of a real office building.  The one-room office had an old recliner from Joe’s dorm room in one corner.  This was my ‘desk’ and my first task was to take a stack of Wall Street Journals and put them into a box.  The box would be stored underneath my ‘desk’.  My responsibilities grew from there…thankfully. 

My First Job (In My Career)

The company raised money and I transition from an unpaid intern to a real live job.  I was off to the races (and so was the company).  I worked for Investment Scorecard for a little over 15 years in a variety of roles.  I started off in operations and wound up on the software development side of the business (in all kinds of different roles).  I felt like I had 3-4 different careers while at Scorecard.  The company was sold to a huge company about 12 years after we started it (in 2007).  I had been a part of a successful financial technology startup…during the 2000 internet bubble…AND during the 2008 financial crisis!  We sold vaporware (software that wasn’t even built to people who thought it was built) at the start.  We spent many nights at work sleeping under our desks and chasing FedEx trucks to the airport to deliver to our first clients their reports.  Then we got more clients, and more, and more.  Soon we were providing Investment Scorecard performance reports to financial institutions I had actually heard of?!?!  What a roller coaster!

Career Change (Off To The C Level)

In 2010, a guy I had worked with at Investment Scorecard, Chopper, had gone on to work for a company that provided home care services.  He called one day looking for a recommendation for an operations guy.  I told him he was talking to him!  We worked it out and I joined a company that provided caregivers across the state of Tennessee that he and his partner had bought from the company’s founder.  When I told my Mom that I was going to work for a caregiver company she said, “but you don’t have a heart”.  Touché!  It was a decent size company with 7 offices across the state.  It was growing quickly.  It was also an operational mess.  My OCD was pinging…where in the heck is the org chart?!?!  Where in the heck is all the money going?!?!  Why is so much of it missing?!?!  I love startups and this felt like a startup…but it wasn’t.  After a few years of hard work, we had doubled in size and the place was running like a top.  We sold the company to a public company after almost 4 years.  It was my favorite job/career/industry by far…so far.  The people that worked for the company were fun to work with and hard working.  I liked that!

Back To Software

At this point, I bounced back to software/finance for a little bit.  I went to work with several of the folks I had worked with at Investment Scorecard at another company they had started, Shareholder Insite.  I helped out in product management while they worked out a sale of the company.  The company tracked/valued venture backed and privately held companies. I got learn a ton about these types of investments and the capital structure of them. The second I heard the sale was done (and that I’d be working in a big company again) I decided it was time to move on.  I also knew I was out of my element and in over my head with all the new really smart people that were now my bosses.  At this point in my life I’ve been successful enough that I don’t have to hang out in a role I’m not truly excited about.  So, another opportunity arose, and I seized it.

Back To Home Care

While at Aid & Assist At Home I had worked side by side with my boss almost every single day.  Stuart and I sat in the same office together and visited all our locations across Tennessee regularly.  He was great at things I was horrible at and I was decent at things he didn’t want to even think about.  When he and I were both looking for our next adventure we decided to start a home care company—Bluebird Homecare!  I’ve always wanted to own part of where I worked.  I love startups because every day throws something at you that you probably didn’t expect.  I like solving business problems that help the company live to fight another day.  It is very easy for me to correlate my efforts directly to the success of the company.  I love that part of it.  It matches up with my personality extremely well.  That said startups are scary as hell.  So. Freaking. Scary!  In so many ways.  I don’t necessarily like that part of it but I tolerate it and am honestly wired for it.  I’ve invested sweat equity, worked hard, and it has paid off.  This was the first time, however, where I’ve walked away from a very nice salary/job to go work for no salary (that’s a zero…$0…noda…nothing…zip…zilch), no clients (no old people), no employees (no caregivers), no nothing, in a super competitive industry like homecare.  Oh, and my four kids were about to start college…did I mention that?!?

I’ve worked there a little over 4 years.  We are not out of the woods yet but we are better off than we’ve been in the past (a trend has been stable).  We have 5 offices up and running (2 more booting up) and several hundred great people providing a great service to so many clients who couldn’t function in daily life without us.  It is easy for me to get up and go to work every day when I get to work with the team I get to work with.  I love it (even on the hard days).

Back to teamwork makes the dreamwork.  Emily got drug into this startup indirectly.  We needed something called ‘money’ flowing into Dean Manor so she became a pre-school teacher.  She had done this earlier in life on and off and went back to work at one of her old schools.  She kept the lights on at the house as the primary breadwinner for our family for some time.  For anyone who says that starting a company isn’t hard and does not involve the commitment of the entire family…ask mine!  We all learn the value of money and how precious time is on a daily basis.  Which is fine, by the way!

I don’t know what the future holds but I’m as happy with my job/career as I have ever been.  There is much more to do and many opportunities exist.  Hammer Down!


Published by deanorolls

Well, if I told you that you wouldn't need to go to my website...now would you?!?!

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