Brian Gill is an active angel investor and business owner. He was also a successful IT consultant, software developer, and software engineer. Gill is the chairman and CEO of Gillware, an IT company that offers data recovery services from failed electronic media.
Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?
I grew up in a small farm community in southern Wisconsin. I was a nerdy little fella that excelled at math/science. It was a lower-middle-class upbringing early, and as I got into high school our family was solidly middle class. My parents had amazing work ethics and put everything they had into their kids.
What is something you wish you would’ve realized earlier in your life?
Many of the intimidating folks with MBAs and carry themselves as important executives are clueless or worse; both clueless and supremely confident. As a young software engineer, I lacked the backbone to confront these folks when I thought there were major structural flaws in their plans/thinking.
What are bad recommendations you hear in your profession or area of expertise?
Have long passwords(2FA or U2F are critical, passwords are the worst way to authenticate users). I don’t need backups because my data is in the cloud. Our digital security is good, I hired an IT guy who ran a pen test! I don’t need cyber insurance as we’re not a target for cybercriminals.
Tell me about one of the darker periods you’ve experienced in life. How you came out of it and what you learned from it?
I’ve led a blessed life. I got put on academic probation as a sophomore in college. I was having way too much fun and enjoying the social aspects of college, and I hadn’t ever needed to work or develop study habits. Turns out there’s a downside to getting straight A’s your whole life without any effort. Eventually, you bump into the subject matter where you can’t just wing it, and when you do you’ll get run over as I did. I learned that if I didn’t want to be loading trucks in a warehouse I need to figure out how to study, in a hurry.
What is one thing that you do that you feel has been the biggest contributor to your success so far?
The key to my success is my ability to build teams in the earliest days of a company. I have a knack for finding folks that want more out of life, complement the skills of the existing team so far, are willing to take risks, and make personal sacrifices. More importantly, for the most part, my intuition has dodged a bunch of bad hires over the years.
What is your morning routine?
I’ve never set an alarm unless I needed to get up at 4 AM to get to the airport. I have a new puppy so right now I’m getting up around midnight and 3 to let the little guy out, but normally I’m up by 5 AM or so. I do a little work, either a work-out or work-work, depending on how buried my day looks. I get my 3 kids up and get breakfast in their bellies. Right now with COVID, my 2 older boys have their school virtual. So, I bounce between helping them with school or helping my employees with something or other. I usually have 2-3 meetings with a small handful of staff every day to keep tabs and push things forward with the 5 business units I oversee.
What habit or behavior that you have pursued for a few years has most improved your life?
I’ve learned to say NO. Earlier in my career, every idea sounded amazing and every person seemed like someone I wanted to work with. Now my ratio is more like 1/20. With COVID, stakes in multiple businesses, kids virtual schooling.. less is more.
What are your strategies for being productive and using your time most efficiently?
Being comfortable delegating tasks to folks even when I’m not sure it’s going to work. Gotta give people a chance and it is a win-win. Either they knock it out of the park or it is a learning opportunity. For my personal time, it is really all about making sure I have 3-4 hours a day to do the tasks that I really excel at. Which I need to coordinate with my wife as she is an incredibly busy doctor. I’m writing this response on a Saturday morning that I cleared the time with my wife.
I always have a handful of monthly goals and quarterly goals we’re always working towards, which really helps make all the little decisions so much easier and faster. If a newer subordinate asks me for clarity on the direction of a particular project, I’m almost never going to spit out an answer. I’m going to ask what they think we should do, and why. And we’re almost always going to do it that way, and hopefully, we work towards building their confidence, so they don’t even ask me next time. Of all the things in business that make me happy, the very best is when a bunch of my teammates make good decisions and execute those plans without me ever hearing about it until it was done and successful.
What book(s) have influenced your life the most? Why?
While I’ve read plenty of books on business etc, I think books in the SciFi/Fantasy realm had more impact on my life. Patrick Rothfuss and Neal Stephenson are current favorites. If I had to pick non-fiction I’d say Principles by Ray Dalio. But SciFi is what really kicks my brain into creativity and relaxation; can’t put a price on relaxing these days.
Do you have any quotes you live by or think of often?
“In this world you’re either growing or you’re dying so get in motion and grow.” ― Lou Holtz