Michael Simmons participated in multiple liquidity events, including partner divestitures, inventory acquisition and the purchase and sale of both web and mobile software. He’s passionate about the user experience with a specific focus on the seamless migration of people from physical to digital environments. Michael’s current projects include Dallas-based Hayloft and Oyster.io, a data-driven creative shop. He holds a journalism degree from Texas A&M University and an MBA from the Mays School. Michael has a loving wife, three super cute kids and a dog. Follow him @mosimmons. 

Who is your hero? 

I’ve always been partial to Sir Richard Branson. How can you not be impressed by someone knighted in large measure due to his success as an entrepreneur? He is a bold entrepreneurial spirit personified. Whether in work, play or philanthropy, Branson is an excellent role model for any budding business leader. However, in life I tend to look toward my dad and several college friends serving in the armed forces for inspiration. Those guys are my real heroes.

What’s the single best piece of business advice that helped shape who you are as an entrepreneur today, and why?

While in graduate school I was told to schedule interviews with a couple Fortune 100 businesses visiting campus. These companies were looking for candidates to participate in their respective leadership development programs. I skipped the interviews. Ignoring that advice was among the best pieces of business advice I’ve received.

Nothing motivates me more than the thought of not working for a large corporation. My goal is to build one, not work for one. Startups aren’t easy. I’ve had my doubts, but as I embark on my tenth startup I don’t regret skipping those interviews.

What’s the biggest mistake you ever made in your business, and what did you learn from it that others can learn from too?

Hire a good accountant. My startup was laser focused on revenue and execution. Our books were only reconciled every couple of months, then quarterly, then twice yearly. It was a disaster. Without solid data upon which to make good business decisions, I found myself always living in the past.

When you’re a young, bootstrapped company you worry about lots of little things. If you don’t get a handle on the books, however, small problems tend to grow into big problems. Good accountants pay for themselves over and over again, because playing catch up with your books gobbles up loads of time and kills productivity.

What do you do during the first hour of your business day and why?

The first hour of my business day is like a brainstorming warm-up session. I make a quick run through Twitter, a few news outlets, and low priority emails. This usually gives my brain enough time wake up, which in turn results in a more productive second hour. This also works as a cool down at the end of a day, acting as bookends for an otherwise busy day.

What’s your best financial or cash-flow related tip for entrepreneurs just getting started?

Whether you’re bootstrapping or spending other people’s money to get your business off the ground, be so cheap you squeak. What you don’t need might shock you. It’s always easier to ramp up spending as your business strategy takes shape. Reducing spend is a little hairy.

Quick: What’s ONE thing you recommend ALL aspiring or current entrepreneurs do right now to take their biz to the next level?

Ask for help. I often fail to heed my own advice, but there is no shame is asking mentors, colleagues, friends, family or total strangers for help. This might be the quickest path to find success as an entrepreneur. You never know where you’ll find a spark that takes your business to the next level.

What’s your definition of success? How will you know when you’ve finally “succeeded” in your business?

Find a metric and stick with it. Maybe it’s an exit, or maybe it’s getting 100 paid customers. Whatever you choose, don’t move the goal posts. Each business is different, so finding the best, quantifiable measure of success for a business is among the most important decisions you’ll make. Success in life is a little harder to measure. Knowing the difference between a successful life and successful business almost assuredly increases your chances of finding both.