Closer look
Alex Bridgeman
Age: 24
Education: 2019 graduate of University of Portland with a degree in accounting and minor in entrepreneurship
Company: Think Like an Owner, The Operator's Handbook
What the companies do: Think Like an Owner: "A weekly podcast interviewing small company owners and investors, with a focus on search funds, micro private equity, and small business operations." The Operator’s Handbook: "A quarterly print-only publication with long-form stories of small company operators improving and growing their companies in the endless pursuit of better." Funded by reader subscriptions
Founded: Podcast, 2018. Publication, November 2020
Accelerators, incubators or competitions: a pitch competition in Denver through UP’s Entrepreneur Scholars program
Outside funding: Has chosen to bootstrap
How did your company come about? Both companies came to exist for the same reason: a lack of attention given to owners and investors of small companies. I also found owners generally didn’t know other owners or peers like themselves. Think Like an Owner and The Operator’s Handbook both exist to change that.
Why start? I started both companies when I couldn’t find other media companies shedding light on the small company ownership and investing world. It’s such a huge part of our economy. I felt it deserved better.
Have you always wanted to be an entrepreneur? I’ve loved studying businesses since I was a kid, when I would read the business section of the newspaper, but didn’t decide to become an entrepreneur until late in college. I always thought entrepreneurs had to start huge companies, but that’s a very small part of the startup world and I realized it was possible to start something small but meaningful to me.
Do you ever feel like you are missing out on anything because you are following this path at such a young age? There’s certainly some opportunity cost to working for yourself at an early age, with the greatest being giving up the opportunity to learn under an expert in the field in which you aspire to excel. I am very aware of this and I’m trying to supplement by building close relationships with mentors.
Have you felt any specific challenges around your work because you are still so young and early in your career? One challenge I’ve struggled with, but have overcome somewhat with support from family and mentors, is consistently underestimating what I’m capable of because of my age. I love the Steve Jobs quote about the world being built by people no smarter than you. I’m lucky to have a village that supports me.
Are there any founders or business people you look up to or want to emulate? I admire any entrepreneur who has built a business around their own intellectual curiosity. A few examples include Nick Fisher (also a UP alum) of Pilot Wealth Management; Ben Thompson, founder and editor of Stratechery; and Jim Grant, the founder and editor of Grant’s Interest Rate Observer.
What has you most excited about your future? The support around me through my wife, family, and countless friends I’ve met gives me confidence to keep going. I’ve been running the podcast long enough that I can see the opportunities for growth and it’s just a matter of executing. The demand is there and I have a plan to address it.
