…and like that it’s over. 10 things I realized over the past 7 months as an entrepreneur.

For anyone who has been following my stint as an entrepreneur, I wanted to update the world one last time. I’ve decided to join Canpango, a Salesforce and Marketing Automation company located in Milwaukee, WI… and I couldn’t be more excited. I feel like I owe some kind of explanation, though, after my last posts.

I realized the happiest moments of my career/life have been centered around helping people, mostly on a 1-1 basis. Whether it was supporting sales, leading projects that excited colleagues, or training on new processes/technology… that’s what all my thoughts & conversations always go back to – moving people forward in different ways. Hopefully, those 1-1 instances add up and are either paid in advance or emulated by others, enabling the masses.

The end goal from a business standpoint is to be a Chief Executive Officer, stewarding the people, vision and assets of a major company/organization. I’m realizing as I get older just how much more experience I will need to have a chance at being successful in that. I will need to further understand people (and not assume I know). What they want and why. To understand situations. To not buckle under some unforeseen pressure. To trust people. To respect them. I’ll need failures & frustrations. I’ll need successes & euphoria. I’ll need experiences with other job functions that are outside my comfort zone. Perhaps most of all, I will need people to teach me. To have faith in me. To trust me.

^ Those were all things I was getting before I became an entrepreneur… I also feel I have a certain skill in Digital Marketing at the moment that should be utilized to it’s maximum. I can make these Marketing Automation platforms sing … and am really looking forward to the opportunity ahead of me.

… but I firmly believe entrepreneurship has helped me, because it taught me so much more about myself. Here’s what I learned over the past seven months. Take it with a grain of salt, as it’s very subjective and only meant to be a window into my personal career journey for anyone who is contemplating making similar moves. I’ll warn you it’s contradictory at times (My hunch is that listening to David Bowie’s, ‘Cat People,’ while writing had something to do with this).

When I first made the leap, I knew I’d be working from home and on my own for awhile. I’ve always enjoyed time to myself, so I wasn’t too concerned, but everything has it’s limits. What I found interesting was that being alone wasn’t so much a problem. The problem was how much I enjoyed being alone. I didn’t think about it at first, but I’d spend pretty much all week by myself…and I was fine. It wasn’t until I realized that I was getting a little anxious (I’m fine, really) at times before I’d have to go out and be social that I wondered if maybe I was spending too much time on my own.

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Where some of the magic happened.

The solution? I quickly learned I needed to stick to a strong routine. Up before 7 am every morning, shower, big breakfast, move through the To Do List, exercise, bedtime at a consistent time, etc… analyze if you must, but get MOVING! I also began to incorporate social activities (luckily I’ve got the best friends and family) on a regular basis. Keeping a schedule actually helped keep me ambitious… An object in motion stays in motion and as I said, I want to help people. You need to be around in order to do that..

I’ve been in the private sector. I’ve been in the consulting world. I’ve been in the agency world. I always had a reputation as a polite, smart and hardworking individual that could give a commanding presentation, but was my success because of that… or because of other people? I could write an entire blog on everyone in my career that have helped me and instilled their knowledge/wisdom (or at least tried to…).

This was on my mind, though. In this case, I had no one else to blame, praise, question, etc. about what was working and what was not. It was all on me. Well, as I wrote last time, I not only established my business, but I secured five clients … and we did good work together. I feel like some of the relationships I developed were on par with similar ones I’ve helped cultivate in the past. I’m very proud of that.

I found it’s easy to be defined by others and to forget our true passions. Once perceptions are created they are hard to break. Tides go in and out, but in random order, I’ve been told I’m too nice. I’ve been told I lack empathy. I’ve been told I talk too much. I’ve been told I’m too quiet. I’ve been praised as an excellent listener. I’ve been told I don’t listen at all. I’ve been told to own the things I’ve earned. I’ve been told I act entitled. I’ve been pegged as “just a sales guy”. I’ve been pegged as “just a technical guy”. I’ve been pegged as “just a creative”. I’ve been told I’m too detailed. I’ve been told I lack attention to details. I’ve been told I don’t know how to take care of others. I’ve been highly recommended as someone who looks out for the best interests of others. I’ve been told I’m not a writer. I’ve been told I’m a great writer and to write more. I’ve been complimented on how much I’ve made people feel at ease. I’ve been told I make others uncomfortable and can be downright terrifying. The list goes on… but it all led to confusion and some restless nights.

I talk about how I want coaching, feedback and advice. I’m very grateful I received some, but what was I going to do with it?..and what goal would I apply it to? I had to accept (and did) that in different situations all of the above were true (and in some cases on purpose). Then I began to wonder how much I wanted to smooth off my rougher edges, as individual instances will not define me. I will be defined by what I accomplish… and I suppose that takes time, more effort..and just being a human (or not trying to be so perfect). My point is that I realized people were always at the center of what I wanted to do and it was great to see that naturally come back out. When I think back on all the things I’ve been involved in, there was always a person or group of people at the end of the scenario. It feels silly to type, but sometimes it can be hard to do (and easy to forget) what you want to do.

… and then I began to sleep again.

I have mixed feelings about people discussing their own level of emotional intelligence, but I do think I improved mine over the past year. I spent a lot of time in coffee shops (more on that later) and I began to see some regular faces. I couldn’t help but study their expressions or wonder what they were thinking and what they’d been through. Some people were always in there by themselves and you began to get a sense of their feelings. Some seemed lonely, some seemed ambitious, some seemed nervous as they waited for an obvious first date or job interview, some cooling down post workout, some writing a novel, some were just there to study or pass the time until something better came along …and everything in between. I absolutely loved being an observer.

I began saying hi to people just because I worried no one else had said it to them in awhile…then I began to wonder what people thought of me, as I was doing much the same thing every day… but the best part? I carried it with me after I left. You don’t always know what kind of day people had or what they are dealing with, so whether at the grocery store, or getting cut off on the highway during rush hour, or sharing the elevator with the grumpy man at 6 pm… I started to smile more and just ask people how they were doing…and actually wanted to know. Cool things started to happen. One such conversation was about the cold brew a gentleman next to me was having. I also saw he was reading, “How to win friends and influence people,” by Dale Carnegie. On his way out, he bought me the same cold brew and had the cashier bring it over to me, giving me the peace sign as he walked out the door. I thought that was wonderful. It was great to see another person thinking about this kind of stuff…

I also realized empathy wasn’t about having pity on people. Whatever race we’re in is with ourselves, and some people don’t want or need help. They don’t want you to ask them certain things. They don’t want you digging into their business. They don’t want you to plan things for them or assume you know how they think/feel. They don’t want to save the world, destroy it or anything in between. They just want to live their lives and need a means to do so. Sometimes staying away or out of the way was the best thing to do. Understanding that makes for an interesting balance and I haven’t figured out how to put it into words yet. Even furthermore, in other cases, some things couldn’t be my responsibility and/or I didn’t grasp the situation, no matter how much I wanted to…

The most interesting part? I’m still not sure I’m right about any of it..

I didn’t mention it before, but this is actually my second entrepreneurial stint. The first one failed pretty miserably. Speaking of experience, I knew from the first stint that I’d need to establish the LLC, a business checking account, organize some marketing, etc… but I took it more seriously this time. I wrote up an actual business plan, created a balance sheet and hired other professionals to help me with legal, marketing and accounting efforts.


I hired Katie Robleski to create my website.  I told her I wanted a touch of Michael Mann throughout.

This allowed me to focus on sales and execution right away. What I’m happiest about is the fact that I not only kept the lights on, I made a good profit. I very much feel I ran a successful business, something I didn’t feel like last time.

Accounting is hard. Legal is confusing. The best sales people are truly a special breed.

I have a good friend who agreed to help me with my taxes and he is as passionate about his job (and better at it) as I am mine. It was great to share in and see.  Another good friend created videos for me, for free (and he knew what he was doing). I hired a lawyer to help with all the legal aspects. He loved talking about it… and it made me feel like I had the right guy. As for sales..to be able to take the rejection day in and day out and 1) keep doing it, 2) not let it affect other aspects of your day  and 3) close some deals …is all beyond impressive. I definitely have some sales in my blood, but I’m too sensitive to get turned down so much or just straight up ignored. Maybe it was because of Karma and an example of me not being empathetic. I don’t always get back to sales people, either..

So I admit I didn’t like all of the sales rejections, but I understood that in order to market my company, I would have to market myself… and that meant I’d have to be out there…ALL the way out there. All of the quote photos, blog articles, client information, videos etc. I knew it may be too much information, but I also knew that certain percentages of people were going to react differently. Some were going to love it. Some would applaud it. Some would like it. Some would dislike it. Some would make fun of it. Some would absolutely hate it.

It didn’t matter. My intentions were good and I’ve known for awhile there is no in between. You either get everything…or nothing from me and I needed to be comfortable with the reactions to that. … and there was something about both failing and succeeding in front of a massive audience. Regardless of the outcomes, the sun still came up every morning and whether you dusted yourself off or settled down after a “Risky Business” victory dance, it was, “Okay now what?” Life moved forward..

Wow. Turns out I was getting taxed twice. Once on my over-all net profits and again when I paid myself (What!!?). Furthermore, not only was I spending my own money to run my business, but I had to spend additional money for my health benefits and to keep my retirement fund growing, which was detrimental to my income at the end of the year…something I took for granted working at other businesses. I also learned what you can write off, what you should write off, what you shouldn’t write off…and really just how the whole process works.

It made me even more fascinated with people who can launch and maintain successful businesses.

I recently went to the doctor for my annual physical. My weight was down, my blood pressure excellent and my cholesterol numbers all got better. A big improvement over last year, when I began to notice a ton of grey hair invading my scalp…

Did I lower my stress level? Was I having more fun? Was I eating better? Jogging more? Tanning (lol..)? Yes – all of the above, but all of that was more manageable for some reason on my own. There were still some occasional, moody cigarettes, though (oops).

Colectivo was my office for the past seven months. Go there. The atmosphere they have created at their shops is amazing. The coffee? I regularly had to ditch my medium sized mug because of the caffeine jitters… and I’ve been a black coffee drinker for about ten years. The green tea, though? I think I supplied their demand.. I’ll miss being able to spend my days there..

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Colectivo – my other office.

So there you have it. This little journey has been such a special experience and one that I’m certain I’ll recall fondly as I move forward. I hope to keep you all updated occasionally, but it might be a bit as I undertake my new challenge.


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