Chief executive officer
“At Heartland, a time-tested, consistent framework for evaluating companies is at the center of every investment decision we make. Over the years, I’ve seen how this ‘investment mentality’ also helps in managing a successful business – including finding the time to actively work on the business.
“For example, successful investing requires zeroing in on critical information about each potential opportunity. A consistent framework helps avoid missing either the big picture or a vital detail.
“The same applies to managing the business. I’ve found these lessons from investing helpful in identifying and asking mission-critical questions. Those questions are vital in shaping strategy as well as keeping an organization’s focus on meaningful results.
“Part of asking tough questions is the willingness to hear ‘tough’ answers and to listen to differing views. Just as we strive to bring together different perspectives in analyzing an investment opportunity, it’s helpful to bring varied—and even conflicting—approaches together to support business progress.
“In both investing and business management, careful listening can help avoid unnecessary risks. It also carries the benefit of freeing up time, as trusted team members put their talents to work in pursuit of a common goal.”
Chief operating officer and co-founder
Vytal Health (formerly Wellness Script)
“Unplugging completely has been the best and most eye-opening thing I can do for myself and my business. I regularly save up travel points and get away for three to five days somewhere exotic. I use my time there to take in the sun and a few drinks but most importantly to reflect and think. I always come back with pages full of ideas and one to two major revelations.
“Changing up the scenery and being able to focus without distractions has been very helpful. My co-founder and I regularly take turns being away from the office and working out of local coffee shops. I use specific coffee shops when I need to grind and others when I need to zoom out and think or read.
“Doing a yoga practice is great because it helps clear my head from all the daily noise. When my mind inevitably wanders off during the practice, I end up having an ‘aha!’ moment of some kind or I am able to think about something very important I’ve been putting off.”
President and chief executive officer
Octavian Technology Group
“If someone is not steering the ship, building a plan and a strategy to work toward our goals, it will be a lot harder to achieve them.
“I was with a former company about 18 months and we were not making headway advancing the business. I talked to one of the owners, who was my boss at the time. He said, ‘You have a diamond in Milwaukee.’ But I knew that I couldn’t grow this diamond in the rough by myself. So, I simply told my staff, ‘I need help.’ After that, people in the office got involved, and it was only then that the business began to take off. We aligned as a team around a vision and that made all the difference.
“Most business owners and entrepreneurs have trouble giving up control. I want to let go so that others have an opportunity to grow. It’s a leadership skill that you build once you realize it’s not all about you. Over the years, I had managers that I didn’t like because I never felt empowered. Give your people autonomy, hold them accountable and it will allow you the time to work on the business. Be humble. Trust people to do their jobs.”