I’ll admit, I don’t have a profound lead in to this review. Phew. What an exhausting year. It was filled with the good, the bad, and the ugly. Maybe I’ll break it down like that. Hope this inspires you to do your own regular reflections.



Living for Monday

If you had said that I would run operations for an online education company to change the way people my age thought about work, I would have referred you to a therapist. If you had said I would do consulting for a Russian ballroom dance dress shop to create cashflow for that operation, I would not only have referred you to a therapist. I would have driven you myself.

Like so many of the other topics in this review, LFM could have gone in multiple categories. Living for Monday was what I consider my first serious jump into a small business… except I felt like the pool was about 40 feet deep and I was about an inch tall. Almost anything that could go wrong or throw up a roadblock did, and yet we smashed through dozens of those problems and kept going anyway.

We made mistakes around money, investors, target market, pricing, and the list could go on and on. So why is this in the “good” pile? Easy… because I learned expensive lessons from every mistake and roadblock without spending a penny…. or only a few pennies.

In a nutshell, I learned:

  • How lucky I am to have a friend and fellow ruckus maker like Barrett to accompany me on these crazy pursuits.
  • That my gift really is in a strategic execution and detail position. Call it COO. Call it operations. Call it whatever else helps you understand. (more later on why this is also in the bad pile).
  • That failing (in a business sense) is not the end of the world. The sting wears off and you aren’t marked with it like the Scarlet Letter. If anything, people respect you more for trying.
  • That money isn’t everything, but in the startup world, being under-capitalized can spell certain death no matter how great the ideas.




I almost don’t know where to start on this one. I would call it a fluke, but I think that’s a smack in the face to God. In August, after months at a job that usually made the fourth or fifth word out of my mouth in the morning a four letter expletive (more on this in the bad pile) I found myself in a job that I was ecstatic about!

It was growing fast, every day was different, and I instantly made 15-20 (now 30-40) new friends that I never hesitate to hang out with whenever I have the chance.

I’ve been very fortunate to experience a lot of different business environments from small business to infant-stage startup to corporate environments. SalesLoft is still a startup, but it is a successful startup that is in is scaling phase which is a completely different environment from all of the others I have experienced. In the 3 months since I joined, the company has doubled in size. I was there for every step of that expansion, and I still have trouble believing it.


No it wasn’t in public, but I have been writing. It has been great! I’ve been writing since about July in Evernote and covered a lot of topics. Looking forward to honing my skills a lot more in 2015, and above everything else putting many of those pieces here or elsewhere on the internet.

I told John Saddington today on Twitter that I was convinced that the fear of being the beginner again at something is what keeps adults from taking on new challenges. This is me being a beginner at something again. Good writing is rarely instantaneous… but you have to start.


My favorite phrase from a great Nike ad.



After years of me telling anyone who would listen about how as a child I could never have a dog, I finally got one! I don’t know if you can find a dog that fits you the same way you can find a girlfriend/boyfriend, but I have certainly found one that is perfect for me.

At 6 years old, this black miniature schnauzer has definitely become my little companion who follows close on my heels making sure I don’t get assassinated (he’s like a little secret service agent dressed all in black).

I had a really hard time getting used to having something around that fully depended on me and giving up a lot of my spontaneity, but it really has been worth it. I’ve learned to be patient with something that at times doesn’t know better while also being firm but caring even when he does know better. The comment I make most to people is, “I think it’s good to have something else to focus on that isn’t about me.” It just seems like good practice for a later stage in life.

Workaholism almost died

Is that a word? It is now. Now if I can only finish the job in 2015. My inability to stop working has never been a secret, but after it cost me a lot of friends, hours of sleep, negative health, and who knows what else… it had to die.

I’ve learned that there will always be more to do in a business that isn’t stagnant or dying. You only have the present right now before it is gone. You can make more money, you can NEVER slow down time or create more of it. Don’t miss it!

More importantly I learned that you cannot tie your sense of worth to the performance of your career. You’re setting yourself up for an emotional roller coaster. When work is great, you feel great. When it sucks, you feel like you’re a failure. Sounds fun right?


Lost my grandfather

I couldn’t put this one under good, but it also isn’t ugly. After YEARS of medical problems, my grandfather passed away at 89. He left such a legacy and while it was very sad, it was really inspiring to see all of the people who came from all over to pay their respects and say how much his life had impacted them. I only hope I’m as lucky to have people say at my funeral the things I heard from others.

I’m thankful that our whole family was by his side during his last hours and got to say our goodbyes each in our own way. We had all been through long years of surgeries, recoveries, his slipping into dementia and providing endless hours of care. That time was really special and he was so ready to go by the end.

I know it won’t mean as much to anyone who didn’t know him, but the memory that will forever stick out is as we were saying goodbye, my grandmother leaned over to him and said that she loved him so much and she’d miss him and she kissed him on the forehead. My grandfather just looked over and smiled and kind of laughed and said simply, “Well thanks!” Even at the very end he could make you laugh.

The unknown becoming known

Most people would consider this an area of great growth and self-awareness, and while I agree, I wasn’t a fan of what I found out. Throughout this year, I had completed a couple different assessments (both on paper and in real life testing) that showed me some realities about myself. In addition, this was the first year I really looked back and fully reviewed the year flaws and all… and boy there were some ugly spots.

1) It is unavoidably clear that my talents are in (as I said before) strategic execution, operations, and the details. 

While part of me was thrilled to have some clear answers that made clear sense because I saw the signs in my everyday life, the other part was mad with what I did not see.

Now I know that while people are predominantly one way, it does not mean that they do not possess other personality characteristics and talents in other areas as well. It was not do much disappoint really, as much as it was that I knew I would have to battle my ego on this for some time to come.

Most people like to think of themselves as the leader. The one who is out front and that has lots of eyes on them. The reality, is a lot of us do not fit that mold and while you can learn how to cope in those situations, you will always struggle until you settle into where you are most ideally suited. For me, in a lot of ways, that ideally suited place is one spot to the right of the person I just described.

After talking to people in those roles and my own reflection, I’m seeing that isn’t bad at all, it’s just different.

2) I seriously dropped the ball in certain arenas in 2014 with regards to follow through.

Now this particular point is painful and came really close to making the ugly pile. This is hard to say because people who don’t fully follow through make me CRAZY! There is clearly some truth in that saying that you see in yourself what you hate in others.

The funny part is that the dropped balls weren’t in my work life, but more in my personal life. It was in the extras I took on or outside commitments I made. I won’t give you all the gruesome details, but just know that it wasn’t pretty and while I’ve righted a lot of those wrongs, I don’t ever want to be that person again. No telling what personal capital and respect that period of time cost me, but it’s done and I prefer not to look back at it with too close a lens.


Job in health insurance

I think saying “ugly” and “health insurance” might be redundant, but it bears emphasizing. The 5 months I spent at a health insurance broker in Atlanta was the result of what happens when you do not financially plan for a startup to fail. I believe my exact words were, “Well I can’t go long without a check, so why not?”.

I could now give you at least a dozen reasons why not.

I saw:

  • people hating their jobs day after day
  • the results of an owner who thinks company culture “just happens”
  • the financial stresses of a company that was failing because it refused to change fast enough (thinking you’re a leader when you are in fact the caboose)
  • an industry being crippled by regulations and legislation (in fairness, in no way the fault of the firm I was at)

Well enough negative. The upsides were that it is the job where I learned (thankfully at a young age) that money is not near as important as you think. I also got to be a part of an industry in the midst of revolution which was exciting in its own right.

Sometimes learning what you NEVER want to do is as valuable as finding the things you do want to do.

I know I could sit long enough and think of plenty of other highs and lows, but I think that sums it up for now. Here’s to a year of lessons (learned both the easy and the hard way) and to a brand new year of adventures and growth.