Starting your own business requires a special mindset. You have to have both a tolerance for risk, and a confidence that you will succeed despite the odds stacked against you. But how do you know if you have the right kind of entrepreneurial wiring? Before I launched my advertising and idea agency, The Weaponry I didn’t have a predictive test to evaluate my risk tolerance. But now I do.
I recenly had a very interesting conversation about risk with my friend Tom O’Hara. Tom is EVP & Enterprise Risk Management Director at Huntington National Bank. Evaluating risk is a challenging task. You must find a way to assess risk tolerance in a way that people can easily articulate.
One question Tom poses in his risk evaluation is this little diagnostic gem:
If you have a meeting with the CEO of your company at 7am, and your commute usually takes 15 minutes, what time would you leave for the meeting?
The answer to this hypothetical question reveals a lot about your risk tolerance. If you say 5:30am you have a very low tolerance for risk. If you say 6:45am you have a very high tolerance for risk. If you say 7am you have trouble understanding the time and space continuum.
My big aha!
As Tom talked through this simple predictive test, a fake lightbulb went off in my real head. I applied the same evaluative criteria to my approach to catching airplanes. When planning my departure for the airport I don’t work off the standard ‘Be at the airport 1-hour ahead of time’ rule of thumb. I know that the check-in period for domestic flights ends 30 minutes prior to scheduled departure. But I don’t use the 30-minute rule either, because I always check in online.
Instead, I use the ‘What time will they close the door?‘ rule of thumb. I have always thought this was the only indicator that really mattered. As a result I am often the last person on the plane. Which has freaked out many of my more conservative coworkers. Yet, I can only remember missing a plane one time in my entire business career. And that was because I had the wrong departure time in my head. Stupid departure time memory malfunction!
What this says about entrepreneurship
Clearly I have a high tolerance for risk. Because those airplanes, they don’t wait (I heard that in a country song). That being typed, I am never unprepared for my travel too and through an airport. I have timed my airport route to the minute, and I allow for a degree of error in traffic, difficulty finding parking, and for crowds at security. On the other hand, my drive to the airport makes me feel alive. So does owing my own business.
Know thyself (but don’t call thyself ‘thyself’). If you have to be at the airport two hours before a domestic flight you may struggle with the coo-coo crazy of entrepreneurship. But if you like rolling onto the plane just as it prepares to roll away from the gate, you likely have what it takes to stomach a couple of years of unpredictability. But there is no right or wrong answer to risk tolerance. There are just different types of rewards. So whether you are traveling for work or pleasure, always consider the rewards that make you happy when you file your flight plan.
*If you like living dangerously and don’t mind missing any of my blog posts then don’t subscribe to this blog. But if you want to play it safe, and have every post emailed to your inbox upon publication, please subscribe today.
I haven’t read Andy Grove’s book Only The Paranoid Survive. I don’t need to. I get everything I need to know from the title alone. If you want to survive in business you have to be paranoid.
Why I bring this up.
I am part of a CEO roundtable known as the Council of Small Business Executives (COSBE) in Milwaukee. We had our monthly meeting yesterday at my advertising and idea agency, The Weaponry. The theme of the meeting was clear. The CEOs in my group are all feeling paranoid.
But here’s the funny thing: none of us are in imminent danger. There is no grim reaper at the door preparing to cut our internet connections and leave our businesses for dead. Quite the opposite. Our futures all look bright. We continue to grow and add new clients. We are hitting exciting milestones that indicate our businesses are moving in the right direction.
Yet we all seem concerned that we are not doing enough. That we are not as productive as we could be. Or as aggressive as we should be. Or as focused. Or as successful. To a therapist we may all appear to have odd self-image issues. Or a lack of confidence. But that is not the case.
The Real Issue
We are doing exactly what you need to do to survive as an entrepreneur. You have to worry about issues before they become issues. You have to invest in relationships you don’t need today. You have to develop plans and infrastructure that aren’t critical right now.
You need to do the little things that are important but not urgent before they become urgent. Because if you wait until they are urgent it will probably be too late. Self-inflicted paranoia keeps you a step or two ahead of the real danger. It activates your fight or flight responses when there is no imminent fight. That’s how you prevent complacency. And that’s how your thrive.
Your personal life.
The same power of paranoia can also help your personal relationships, fitness and finances. If you are paranoid that you are not doing enough, you will invest action in each of these three critical areas before they become real problems.
Embrace your self-inflicted paranoia. It’s a great survival tool. By pulling the fire alarm in your head you’ll be prepared before any actual fire has a chance to block your escape route. Better yet, there is a good chance that fire will never come.
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If you like shopping for furniture you should become an entrepreneur. Because one of the by-products of owning a growing business is you need to buy products like chairs and table for your team. The Weaponry, my advertising and idea agency, now owns 14 comfortable chairs, a couch, several tables, and one custom-made lamp. The lamp is probably considered lighting. But this is my blog and I’m calling it furniture.
The Coffee Table Quest
We quickly found options we liked for most of our office furniture needs. But there was one piece that we just couldn’t find in stores or online. We wanted a statement-making coffee table. In full disclosure, I don’t drink coffee. So I think of it as a chocolate milk table. But because the rest of the world knows these types of drink-stabilizing platforms as coffee tables, I will give in to peer pressure and act like I will enjoy coffee on them like everyone else.
Our office space is very square. The furniture in our casual seating area is very square too. So we needed a long table with a curvy figure to round out the room. A surfboard-shaped table would be perfect.
After we had sufficient feedback from our social networks we ordered our custom designed table. Then we waited.
After about a month, and some unfortunate weather delays in the epoxification process and FedEx’s delivering-during-a-snowstorm process, our new table showed up yesterday.
The next step is for you to stop by to enjoy a tour of our office and a beverage on the board. Make The Weaponry part of your next swing through Wisconsin. If you live in Milwaukee, stop by and let’s have some chocolate milk, coffee, tea, beer or a juice box in our newly completed board room. We’re expecting you.
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There are two kinds of people… We’ve heard this intro line many times before. We love to simplify the world’s inhabitants this way. Because it offers an easy construct to think about complicated topics. I recently read one of these ‘two-types-of-people’ observations that wowed me with its simplicity and profunditude.
Here it is:
There are people who prefer to say ‘yes’ and there are people who prefer to say ‘no’. Those who say ‘yes’ are rewarded by the adventures they have. Those who say ‘no’ are rewarded by the safety they attain.
Wow! With this simple statement Johnstone summarizes the difference between accepting and denying offers that come your way. Did you notice that both outcomes are positive? You either walk away with adventure or safety. Nobody goes home empty-handed.
Which one are you?
The key is to know which outcome you really want. I am an emphatic Yes-Man. I like road trips without reservations. I am all in on the adventure or life. I am an entrepreneur. Entrepreneurship is all about saying yes. So is creativity. I see all of life’s challenges through the ‘Yes,and’ lens of improvisation. It truly makes every day adventurous, exciting and full of new possibilities. I’m not saying it is better than safety. It’s just better for me.
Make sure you know what makes you happy. Know what makes you sleep well at night. And reward yourself with more of that. If you prefer the safety, predictability and peace of mind of home then embrace it unapologetically. If you prefer adventure, embrace the bruises, wardrobe malfunctions and flat tires as souvenirs from the trip.
*Yes-Man and No-man are not intended to be gender specific. Regardless of your gender please consider subscribing to this blog. It’s written for people who prefer a safe reading adventure.
In the spring of 2016 I left my job as EVP, Executive Creative Director of a large advertising agency. It was owned by a publicly held advertising agency holding company that employed 80,000 people in over 100 countries. One of the great benefits of working for a company that size was the benefits themselves. Because when you have that many people in your organization, you have Bezos-level buying clout.
On My Own.
I love a good adventure. So I left the cushy benefits behind and started my own advertising and idea agency called The Weaponry. I love what we have built. The Weaponry is quick and nimble. Strategic and creative. It is a really fun place to work and offers a great culture of collaboration. We have a lot going for us. But one thing we do not have is benefit-buying clout.
The Hard Part
When I launched The Weaponry I asked a lot of questions of my entrepreneurial network about a broad range of subjects. In return I got a lot of great advice. But when it came to insurance I got absolutely nothing. Unless those crickets I heard were trying to tell me something (chirp chirp… run while you can… chirp chirp).
I could tell by the lack of insights that insurance was the toughest nut for entrepreneurs to crack. Those who did comment said things like, ‘Yeah, that’s hard. I don’t know what to tell you.’ And, ‘It Sucks.’ And, ‘I would love to help you, but I would rather set the world record for most paper cuts received over a 24-hour period than talk about health insurance.’
Me vs Goliath
However, I am very proud to say that as of January 1st, 2018, The Weaponry offers insurance benefits. I wanted to share my experience with anyone thinking of starting their own business, or wondering how Obamacare impacts a small business and its ability to grow and compete.
Starting The Search
Over the second half of last year I began planning our employee benefits for 2018. I wanted to offer health and dental insurance. But I also considered a couple of other benefits, including life insurance for full-time employees. But as with so many other aspects of this startup adventure, I decided to simplify to make sure we completed the critical mission.
I began with research. I learned right away that you need at least two non-related employees in your business to be able to offer insurance as an employer. We qualified. I found my way to the health insurance marketplace and started poking around and modeling various products and prices. But in a vacuum it was pretty hard to evaluate what was good, what was necessary, and what was not. From this initial poking I learned my first lesson:
Key Insight: You will not feel empowered to make a good health insurance purchasing decision if you try to do it on your own.
My business finance advisor encouraged me to talk to an insurance broker, and preferably more than one. He encouraged me to have them model a variety of options so that I could get a feel for the landscape available to me. By talking to more than one broker, he said, you can compare and contrast styles to know that you are getting the right option for you. This was all good advice. But I still didn’t know how to find a reputable broker, let alone multiple brokers.
My Wife To The Rescue
My wife Dawn is a smart woman, and an important part of The Weaponry brain trust. She was the one that finally got us moving in a positive direction on health insurance. How? She talked to our neighbor Sally.
Sally’s husband, Bruce is the President at EBSO, a third party administrator (TPA) benefits solutions company. However, because of our size and our specific needs EBSO couldn’t help us, yet. But Sally said that Bruce frequently partners with Jon Rauser at The Rauser Agency for clients of our size. Dawn got Jon’s contact info. And within a few days Dawn and I were sitting in Jon’s office.
Key Insight: A good wife is the best business asset in the world. This may also be true of good husbands, but I’ve never had one of those.
Dawn and I met with Jon, and it couldn’t have gone much smoother. He started by offering us a range of three or four different insurance providers. Based on our preference, and the providers prevalence in our healthcare market, we quickly narrowed in on one health insurance provider. Then it was a matter of comparing deductibles to get to the final premium options. We simply had to share the ages and family status of our employees. With that we were able to see projected costs, broken down by employee.
Once we provided the names and ages of our employees who would be opting in for our insurance we had to sign a couple of forms to initiate coverage. We also needed forms signed by the full-time employees who were opting out, acknowledging that they had been offered coverage. Next, we had to decide how much of the premium we would pay for our employees. Then we had to send in a check for the first month’s premium.
Then we were done. Seriously.
We Did It!
We had an employer health insurance plan! We have dental insurance too, which was easy to get. We were all grown up! And we were becoming an even more attractive place for smart creative people to work! We had climbed the most daunting mountain on the Entrepreneurial Range. And we planted The Weaponry’s flag at its peak.
Why was the process so easy? Obamacare. I should insert here that I am a staunchly independent voter. I grew up in Vermont where independent thinking flows like maple syrup. I think the two parties are antiquated and don’t allow for my complex vision of the world. But Obamacare made it really easy for this startup to insure our employees. There are no pre-existing conditions. We didn’t need medical exams. We didn’t need to take a lie detector test. I didn’t have to tell anyone that my Great-Great Uncle Nels choked on a peach pit when he was eight years old. (RIP Little Uncle Nellie…)
Is Obamacare perfect? No. It has driven insurance costs up by 30%. But you know what? My baseline is today. So I simply look at the price today and ask, ‘Can we afford to pay this?’ And the answer is yes.
I can’t change the costs. But what should it really cost? I have no idea. All I know is that we were able to get it fairly easily, and all we had to do was pay for it. Our premiums are not much more expensive than the COBRA prices I had been paying since I started The Weaponry.
I may hate Obamacare in the future. And I certainly don’t want to ever pay more than I have to. But today I am happy to have easy access to health insurance for my team. I want to make sure they are protected. So as you follow the political fight over Obamacare, know that this independent voter, who owns a small business said it was easy to protect his team because of Obamacare. And the small price to pay is simply a larger price to pay. And today, we’ll take it.
*If you know someone thinking of starting their own business that could benefit from this story, please share it with them. If you would like to learn more from my entrepreneurial journey consider subscribing to this blog. If you have more specific questions about my health insurance experience please contact me directly. I am happy to share what I know.
Your first act of the day sets the tone for how your entire day will go. Some people cuddle with a cup of coffee. Some read. Others exercise. While still others begin their morning by repeatedly jabbing at the snooze button on their alarm clock as if they were picking a fight with the Pillsbury Doughboy.
My First Habit
My first act of the day is simple, and more impactful than any of the above. The very first thing I do each morning when I wake up, is smile. I smile and instantly the day is good. It makes me feel as if the day is a game that I am ready to play. I feel funny and playful. Because smiling to yourself in the dark for no reason is a funny thing to do. But it puts me in the right frame of mind for the 18-hour adventure ahead.
Life Comes At You Fast.
Like everyone else, I face challenges every day. I have 3 semi-domesticated children (12G, 10B and 7B). I have a home that regularly throws me surprises. I have a commute that I don’t control. I own an advertising and idea agency called The Weaponry, which comes with employees, contractors, clients, finances, insurance and a landlord. And they all have the potential to hip-check my plans each day.
But that first smile in the morning makes me feel as if I won the day before the sun even gets out of the starting blocks. It sets the tone for everything else. It reminds me that funny things are going to happen that day, and it is up to me to see those events as humourous, and not tragic, vengeful or a clear sign of how much the universe hates me.
Put a smile to work for you.
Try it yourself. It is the easiest positive thing you’ll do all day. Yet it has the power to propel and protect you until you crawl back into bed at night. And if you have not yet smiled today, do it now.
If you find that a morning smile helps set a positive tone for your day let me know. If you have a great way to start your day that might help me, please share. I’ll take all the help I can get.
*To learn more about how I approach life and business you could shadow me 24-7. Or you could subscribe to this blog. It’s really up to you.
There are some business secrets they don’t teach you at Harvard Business School. Like the fact that every great business needs a great sticker. The Weaponry, my advertising and idea agency, now has a great sticker. It comes from Sticker Robot. Which I think is where The Jetsons and R2-D2 get their sticker supplies.
Sticker Robot makes the best silkscreened stickers in the business. But if you want some for your business you should order them the same day you establish your legal business entity. Because they take a loooong time to produce. We ordered ours back in November. They finally arrived on January 16th.
A video on how Sticker Robot make their world-famous stickers.
The Modern Branding Iron.
The whole concept of branding originated from ranchers who branded their livestock with a hot iron to identify their little dogies. Today I find very few people who will let me sear them with a red-hot iron. So we use these 2.5 inch X 2.5 inch vinyl stickers instead. I have already placed one on my computer, my Yeti tumbler, my car and all three of my children.
Check out that backside… (It’s stickerlicious!)
But what I really love about them is their backside. Sticker Robot allows you to print a message or design on the back of the sticker. So we added some of our philosophy. And some of our philosophy about our philosophy. And we added a call to confusion. Which is like a call to action, if the action actually leads to more confusion, like our website does. Visit theweaponry.com to see what I mean.
Then we also added a note about the importance of proofreading. See the *note below? I’ll wait while you review.
Did you find the typo? Did you look carefully?
If you didn’t find the typo it is probably because there is no typo. We just thought it was a funny addition. And perhaps it would increase engagement. Who reads the back of a sticker two or three times? Well, if it’s a sticker from The Weaponry, and you feel challenged, maybe you will. Then, maybe you walk away with a story about how you spent 60 seconds looking for a typo that wasn’t really there.
This sticker sums up The Weaponry pretty well.
We believe in the power of a consistent brand look.
Red reflects our enthusiasm.
We believe the most powerful weapon on Earth is the human mind.
We believe that business is war.
We believe we shouldn’t take ourselves too seriously.
And we believe in finding fun ways to increase engagement.
If you would like a sticker just ask (I now carry them with me everywhere). Or leave a request in the comment section below. You can also stop by The Weaponry to pick one up (1661 N. Water Street In Milwaukee). If you are looking for a job, an internship, a chance to network or just a good excuse to come for a grand tour of The Weaponry’s World Headquarters, a sticker request is a good in. And we have a sticker with your name on it. Well, actually our name is on it. That was just a figure or speech.
*If you would like to stick around to learn more about The Weaponry and my entrepreneurial journey please subscribe to this blog. You may even find some real typos.