In this Real Humans: Alumni, we meet entrepreneur Chris Deitrick, Columbia MBA ’23. He took a reflective pause during the pandemic and recharted his path toward entrepreneurship—ultimately leading him to found two companies, Small Bear and Spring Companies, focused on acquiring small businesses. With a background in implementation roles at Epic Systems, Honest Buildings, and Procore Technologies, Chris entered Columbia Business School aiming to pivot into product management and eventually launch his own venture. At CBS, he discovered the world of Entrepreneurship Through Acquisition (ETA), a revelation that changed his post-MBA trajectory. An internship at Amazon provided practical experience and confidence, but it was the exposure to alternative paths to ownership that fueled his leap into founding. Based in New York and committed to building lasting connections, Chris credits Columbia’s network and culture for giving him the push to bet on himself—and encourages future MBAs to explore broadly, take risks, and let curiosity guide their choices. Read on for his Columbia alumni story.
Columbia MBA Alumni Profile: Chris Deitrick, Founder at Small Bear and Spring Companies
Age: 31
Hometown: Richmond, VA
Undergraduate Institution and Major: Psychology, James Madison University
Pre-MBA Work Experience: All in technology industry – 2015-2018 – Epic Systems (leading health software company) – Implementation consultant; 2019 – Honest Buildings (series B start-up later acquired by Procore) – Implementation lead; 2020-2021 – Procore Technologies (leading construction software company) – Sr. implementation lead
Post-MBA Work Experience: 2024 – Amazon – Senior Technical Product Manager – technology; 2024-2025 – Founder, Small Bear & Founder, Spring Companies – private equity
Why did you choose to attend business school?
I have always planned to become an entrepreneur, eventually. When the pandemic struck, I reflected and realized my career wasn’t meeting the goals I had set for myself in my early 20s.
I had always assumed founding my own tech company was the right path, and the best skills you can learn for that are (arguably) in the product management function. However, that’s a long transition if you’re not a software developer, software designer, or coming from a prestigious background.
I figured I could spend 2 years making the transition internally, or I could attend business school and, in 2 years, make the transition and jump to a top firm in terms of product-building learning and culture.
Why CBS? What factors figured most prominently into your decision of where to attend?
First, from a career outcome perspective, I didn’t see much difference in how the schools performed, at least in the technology industry. Some schools have slightly better networks, but the difference is less important in tech.
Second, I saw Columbia and New York punching below their weights in terms of their tech community and activity. New York has a reputation for finance, and so Columbia does as well, but it still employs a massive number of people in the tech industry. I liked the idea of attending a school where I could correct that.
Finally, personally, I was living in New York City and wanted to build a new network. Mid- and post-pandemic, lots of people shuffled into and out of the city – and business school could rebuild a community.
This has completely proven true almost 2 years later. Anecdotally, I believe a higher percentage of Columbia’s student body stays in the region than any other business school. Students are all jostling for New York jobs, and so you actually get to keep your friends.
As a related point, for someone like me who wanted to stay in New York post-MBA, being at Columbia provided an extra advantage (beyond the obvious physical proximity), because companies recruiting there know that students want to stay there. A large percentage of Amazon’s offers to Columbia students were to stay in New York, for example.
What about your MBA experience prepared you for your current career?
My current role is a founder/co-founder of two firms focused on buying small businesses.
The most obvious way the MBA prepared me – it taught me this was even a thing people could do.
Beyond that, the MBA pushed me to believe I was ready for entrepreneurship. Going into school, I always thought – “I’m not ready; I need XYZ.” But, seeing other students doing it at school made me realize – no one has this figured out, and if they can do it, you probably can.
Without those points of comparison, I probably never would have made the jump.
What was your internship during business school? How did that inform your post-MBA career choice?
I interned at Amazon, and I enjoyed the work and level of responsibility. It felt like the right step while I figured out what kind of company I wanted to start (and continued to battle the ‘am I actually ready for this’ syndrome … and save up).
Why did you choose your current company? What factors figured most prominently into your decision of where to work?
After I completed my internship and signed my return offer, I took the Entrepreneurship Through Acquisition class at Columbia on a whim. This is where I learned that there is another way to own and lead a company – by buying it with money from banks and external investors.
The concept was a revelation to me, and I realized that after 2-3 years at Amazon, I could afford to take off another ~2 years to either start a company or find one to buy.
I ended up trying both in the months between graduation and starting at Amazon. And while I enjoyed both, I realized that starting a company would be a much longer process.
After some time at Amazon, I realized I had the financial runway much sooner than I expected, and I took the plunge.
Advice to current MBA students:
–One thing you would absolutely do again as part of the job search?
Experiment with different career paths – I actually tried some consulting coffee chats early on, and quickly realized it wasn’t for me. I’m glad I got those ‘what-ifs’ out of the way. And I lost nothing by doing so, because the recruiting cycle didn’t overlap with tech.
–One thing you would change or do differently as part of the job search?
Experiment more and seek part-time internships. I wish I’d have been more persistent in building internship experience, because that would have given me a better sense of what different paths were like.
I also felt compelled to only take opportunities with what I felt was a reasonable hourly wage, and I now am less sure that’s reasonable. After all, the student positions we take in career centers and the like often pay much less than a market rate. Why not just accept the same for helping and building relationships in an industry of choice?
–Were there any surprises regarding your current employer’s recruiting process?
Luckily I didn’t have to “recruit” for my current role. But selling myself in an entrepreneurial context has been an interesting contrast to recruiting.
When you work for others, and especially when seeking new jobs, you come to learn that your experience – your resume, every bullet – matters.
But when you’re selling ‘yourself’ to a potential partner – even if that partner is a business owner who will sell their business to you, and make you the CEO – you rarely give more background than a 2-3 minute introduction. You might strategically call out some points of your experience here and there.
But by and large, you are telling a story. Your actual background is nearly irrelevant. And that’s despite the fact that the role you’re seeking is certainly the hardest one you’ll ever do.
–What piece of advice do you wish you had been given during your MBA?
I would say to try more varied activities and take more varied classes. I’ve talked about in-semester internships and career paths already. But beyond that, join as many new and interesting clubs as you have time to – even at the expense of things that seem directly career relevant – and take classes outside of your past/future domains.
The reality is that none of your MBA experiences will be the thing that accelerates the career path you’ve chosen.
But they might expose you to something totally new. That’s literally what happened to me, and I got lucky – the Entrepreneurship Through Acquisition class was the only finance-related class I took besides the core corporate finance course.
Ironically, I don’t use what I learned in that class – I’m doing a different type of acquisition than what they taught – but without it, I’d be somewhere totally different than where I am today.
So if you’re unlikely to directly apply the experience after school, you’d might as well let it take you somewhere new.
