What Eight Years Working in Higher Ed Taught Me About Growing a Business:
In 2015, I walked into my supervisor’s office and told them I was leaving to continue growing my business full time. She was not shocked. I’d been tilting toward entrepreneurship and had a tiger by the tail in the form of a growing software company. I was half-time on a full-time opportunity and made the decision to go all in.
Rewind to 2008: I moved to Chicago without a job and hit the pavement. I was applying everywhere, and a small private liberal arts college 90 minutes outside the city gave me a shot. I started as an entry-level admissions counselor at Rockford University. I’d had MANY jobs, but this was my first career. It was
Nobody Knows Who You Are:
And that’s a good thing. You have nothing to lose.
This is a good lesson in entrepreneurship. I moved from upstate New York to Rockford, Illinois. I went to high school in Rochester, attended college in Rochester, and built an incredible network of friends in Rochester.
I accepted the job in Rockford and accepted that I would be 688 miles from friends, family, and familiarity. I was starting from zero.
Everyone I met was new. I said yes to everything, and one of those moments in life where you have more time than you know what to do with. Someone wanted to go bowling and invited me? Sure! How about a minor league baseball game? You bet! Need a volunteer to go to that college fair in Wisconsin? Sign me up.
Key Learning:
When you start a business, nobody knows who you are. You’re slowly building a reputation. You can take your time; you can pick your connections, and you can test and fail without anyone noticing or caring. The stakes are low when you start, and that’s a really good thing.
Consultative Sales Rules the Day
College students and parents want help navigating an insanely complicated process. What’s the cost? What’s the value? Do professors actually care? WTF is a FAFSA?
This is true of any sales in any vertical. Once you know the business- and you should really get to know the business. You’re in the top 1% of people with that knowledge. Teach. Coach. Add value. The “deal close” increases will follow.
Key Learnings:
Inbound leads (people submitting inquiry forms, ghost applications, walk-ins, new website visitors) should get 90% of admissions counselors’ attention and focus. Calling prospect lists was arduous, expensive, and demoralizing. Spend resources on interested prospective students. What would happen if you could move all the students who listed you as their second choice up to their first choice, instead of targeting students who have you ranked in the double digits?
Be Ruthlessly Frugal When You Need to Be.
Bureaucracy gets a bad name in the “move fast and break things” culture of entrepreneurship. I remember six hours of administrative paperwork after accidentally putting a personal five-dollar-foot-long on the company card.
I’ve evolved to spend money to make money, but when starting out, the practice of thinking hard about each credit card swipe, doing more with less, making something out of nothing: these are skills acquired through practice. Had my career started with a large expense account and lavish spending, it would have been hard to backslide toward frugality and resourcefulness when starting out.
Boot Strapping GeoFli
Operate in the Frontier:
A statistic that would come up at industry conferences was the total high school-aged population. The total addressable market. If the trend was pointing toward a shrinking high school-aged population, there was a heightened sense of urgency. Urgency to send more direct mail. Urgency to send more email.
The key takeaway here is that you’re never going to send the most direct mail. It’s like competing on price. Someone can always undercut you. So we had to operate on the frontier. I visualize this as the backed-up line at a drive-through at Starbucks. You can get in line, or you can park and walk inside to place your order to skip the line. Or quietly opt-out all together.
How to Win At Marketing in 2026? Hike a ¼ Mile.
Key Takeaway:
You’ll never beat Goliath. There’s always someone who can spend more money on ads, pay top-tier talent more, and be at the front of the long, long line of best practices. Opt out. Don’t even get in the line. Look for the new storefronts. Start your own line.
Don’t Hire More People to Solve Bigger Issues
Coined by Fred Brooks in his 1975 book The Mythical Man-Month, the law states: “Adding manpower to a late software project makes it later”. Nowhere is this more present than on large teams. The concept is the false belief that team members and months are interchangeable, assuming that if one person takes 10 months, 10 people can do it in one month.
Key Takeaway:
We’ve kept our team small. And we move fast. When we’re presented with a problem that feels like the answer is “more people,” we challenge that assumption and see if there are other ways to navigate.
