10 Things You Always Wanted to Ask an Entrepreneur

ask entrepreneur

I was recently invited to speak to a group of high school students.

Over the past few years, I’ve had the opportunity to speak to a variety of audiences – from college students to seniors – but rarely to the 18-under crowd.

Most of my seminars focus on generational trends, entrepreneurial shifts, and general marketing and public relations strategy. But the high school contact requested I share my entrepreneurial story with an audience full of teenagers and answer any questions they might have about entrepreneurship.

And boy, did they have some questions!

One of the beauties of being young is that naiveté is a culturally-accepted excuse for asking things others one not (or be too embarrassed to). As a fellow millennial, I appreciated my high school audiences candor, and was reminded by their questions of many of the concerns I had just a few years ago, when faced with my very first business decision.

So here’s a list of 10 things you always wanted to ask an entrepreneur (but were too afraid to):

​Do you ever freak out when faced with making big decisions about your company?

Yes – embarrassingly, yes. I freak out, as you put it, a lot less today than I did four or five years ago.

It takes time and making it through a lot of experiences to build up your confidence. When I first started my business everything was new. I remember the first person that defaulted on their bill – my cash flow was off and I just about lost it.

​Today dealing with that kind of stuff is old hat, which means less freak outs. Spirituality and self-discipline have helped a lot – regardless of what your religious beliefs are, The Four Agreements and You Are Here are two great resources for minimizing the panic. Over the past year, I’ve spent some time prioritizing mindfulness training, which helps with emotional reactivity.

Click here to read 3 Mindfulness Tips for Entrepreneurs.

​Do you ever regret starting your own business?

Yes – I think most entrepreneurs that were honest with themselves (and not bankrolled with a cush trust fund) would admit feeling a twinge of regret during the low points. As a military spouse (a demographic with record low employment and earnings) market value employment wasn’t even an option for me, so I knew that if I wanted to make more than couple bucks as hour, I’d have to create my own opportunity.

​But there are times – especially following significant investment/pre revenue period – where I have caught myself looking at my civilian employed colleagues who were buying up vacation homes, imported cars, and Caribbean trips while I’m in a position of making money or losing it all and I think, “Damn, must be nice to have that type of security.” But most days, I’m pretty happy entrepreneurship. It’s not easy, but the autonomy is amazing.

​How much money do you make?

As a consultant, I charge by the hour and my hourly is on par with what other MBA consultants charge in the US markets. I’ve had a few peers react to my hourly rate with, “Wow – you must be rich!” but they fail to consider all the overhead expenses that hourly must cover. My hourly rate includes: health insurance, life insurance, car expense, travel, marketing, continuing education, office equipment, contract employees, taxes, and a lot of other miscellaneous costs of doing business. What I see, after all the overhead expenses are covered, is just a fraction of what I’m charging per hour for my time.

​Can you get a mortgage like employees can?

Securing traditional mortgage can be a real challenge for entrepreneurs, post mortgage bubble burst. Subprime mortgages aren’t readily available anymore, thus requiring fairly stringent approval (two years of stable business financials) for self-employed. It’s frustrating, especially since employees rarely have to even show more than three pay stubs to get approved for a mortgage. Owner financing and lease to own are good options for entrepreneurs wanting to purchase their own home.

Click here to read 5 Life Hacks for the Entrepreneur. 

​Have you ever lost money?

Yes, several times. Losing money is part of the entrepreneurial game – few folks win them all. As a business professional, I’m trained to always assess risk and act accordingly. In the four ventures that went bust, the destructive variable that tanked us wasn’t “traditional” business issues. It was always something totally out of left field, like one of my main customers being arrested for fraud, or my equipment exploding, or a family member hospitalized for months. A savvy business person tries to identify as many potential risks as possible, hedge against those, and then dives in. Acts of god still happen, and some of theme are hard to protect against.

Does running a business strain your personal relationships?

At times. The type of stress associated with entrepreneurship is very different than the type of stress associated with employment. Personally, I feel the type of stress that frequently accompanies entrepreneurship is more “eustress” (healthy drive) vs. health damaging stress, but that’s just my two cents.

​The demands of a business during startup and growth phases can be challenging, especially when operating with limited resources. Being upfront with my loved ones about how unavailable I’ll be during these seasons of business intensity has helped keep things from rocking the boat, but everybody’s different.

Click here to read How to Be in a Relationship as an Entrepreneur.

​How do you know if you’ve made the right decision if you don’t have a boss to talk to?

Mentors. I love mentors – totally game changer for my career. I believe everyone needs a mentor (or two or three) – even employees. Having someone else to run things by is extremely helpful. Even if they don’t have experience with your immediate problem, they can help connect you with the people and resources that can, or even just provide a fresh perspective. As an entrepreneur, it’s easy to get lost in the trenches; a mentor helps you take the mile high view and put everything in proper perspectives. Most things aren’t really as big a deal as they seem at the time.

​What do you do when your business doesn’t make any money?

Well, you figure out why your business isn’t making any money and you fix it – ASAP. In the meantime, you find other ways to pay your bills. Most entrepreneurs will pick-up side gigs or freelancing opportunities to help keep the lights on while their business matures. I’ve done everything from portrait photography to bartending to breaking colts to keep my family afloat when my business wasn’t performing. Unlike employment, you can’t always count on a business, especially a new one, to consistently profit enough to meet all your needs. When that happens, you just have to get creative.

​Does it ever get lonely working for yourself?

Yes, but it also got lonely working for other people as well. Working all day around difficult personalities and uninspired people can be more of a drain than even the loneliest of days as an entrepreneur.

​When I first started my business, I (mistakenly) believed that working for yourself meant working by yourself – all the time. That simply isn’t true. Even though many home based self-employed may log a couple hours a day alone in their home office, most prioritize “getting out there” on a regular basis. Local networking groups, chatting with fellow treps, meeting with potential clients are all just a few regular activities marked on my weekly calendar.

As an entrepreneur, I also have way more free time on my hands than I did as a full-time employee, meaning that I can (finally!) invest time in a few of my favorite hobbies (and not just on Saturday morning). I run competitively, ride dressage on my two mares, travel extensively, and even have hours of free time each week to volunteer at my favorite veteran organization right here in Kansas City.

​How do you handle failure?

This is one of those questions that if you asked 100 different people, you’d get 100 different answers. Everyone (successfully) handles failure differently, depending on your personality, processing preferences, belief systems etc. Main thing is that you find a way to move beyond failure that works for you.

How do I handle failure? I let myself “feel” it – the pain, frustration, etc. – for a set amount of time (usually no more than 48 hours).  I may cry, run an extra five miles, beat the crap out of my well-worn punching bag, but after the designated “pity party” – aka “processing” time – is up, I move forward. I take out a piece of paper, list the contributing factors associated with project flop (note: negative self-talk is NOT allowed here – just tangible contributing factors), and write down five to ten lessons I learned from the experience. I think about how I can apply these lessons to projects moving forward. Then I do just that – move forward. Spending too much time wallowing in “I failed, I failed, I failed” is extremely counterproductive to any future success.

Click here to read Trial and Error: an Essential Part of Success.


You Might Also Like

No Comments

Leave a Reply