Last week concluded my final semester as an entrepreneurship instructor at my alma mater, The University of Texas at Dallas. For context, I taught an advanced course in the business school called Startup Launch, which was capped at 15 students and structured like a real-world startup accelerator. While I emphasized market validation and analysis (with heavy inspiration from The Mom Test by Rob Fitzpatrick), we also covered special topics such as building a team, legal, and finance leading up to a rigorous final pitch to a panel of judges. Students had to apply with a real business idea for consideration. Class met every Wednesday from 4-7pm, so it was reasonably unobstructive to my schedule. (Side note: ironically, I graduated from the computer science school, not the business school.)
It has been a rewarding (albeit sometimes trying) four semesters. When I was invited to join the faculty at 25, I had recently left my acquirer, and my new startup was still in its infancy. I saw this as an opportunity to meaningfully give back to the next wave of aspiring entrepreneurs. Before long, it had become my favorite passion project/hobby (which I’m sadly ending now because my startup is going nuts). I revamped the syllabus and rebuilt the lectures from scratch based on my experience building companies. And I made two bold promises at the beginning of every semester:
- I care about you more than any of your other professors.
- If you truly put in the work, you will grow more personally and professionally here than in any other class.
My biggest confession: teaching entrepreneurship is a paradox. Startups are much more of an idiosyncratic art form than a science. As hard as I tried to simulate the work ethic, pressure, and critical thought required when starting a company, I knew I couldn’t come close to the real-world rigor in a safe classroom environment. Sometimes I could give a secondhand glimpse through storytelling, but that never does it justice. There is simply no standard blueprint for teaching entrepreneurship, especially in a limited academic setting. Besides, I believe that a leading indicator of potential success is the inherent qualities and values of the founder(s), which can’t be isolated or forced in a classroom. Trust me, if I could take a group of random people and systematically turn all of them into successful founders like a conveyor belt system, I’d sell my own course.
In my final email to my last class, I described this as follows:
Startups are, to put it bluntly, brutal: you will constantly fight against strong competitors, doubters, the status quo, luck, and even yourself. You will cycle between the arduous and the sublime—sometimes within the same day. And there is no easy escape when you are responsible for the team, customers, friends, and family who placed their trust in you. To this day, I haven’t figured out how to articulate the mental turmoil in a way that others can understand without experiencing it firsthand. It is like a rite of passage for every serious founder.
Every instructor has a teaching philosophy. I was required to submit one before joining the faculty. In the context of teaching entrepreneurship, particularly in this advanced course where students express a desire to start a company by applying (as opposed to an introductory survey course), I view my role as being as candid as possible about the realities of taking this path. There is a pragmatic danger in not properly balancing encouragement with criticism (especially in today’s participation trophy culture…no wonder people hate on my generation). If I’m not transparent enough with these students, that could lead to them deluding themselves into an opportunity cost that will hang them dry. And I don’t want my students to experience that pain if they can avoid it.
In that lens, managing emotions was one of my biggest challenges—it was not unusual for me to be the first person to tell a student that their idea (or market analysis, deliverables, business partner, etc.) sucks. (To be fair, I provided many warnings up front about the difficulty of this course and encouraged students to drop if they didn’t want to commit to the work.) But someone must deliver that feedback. That approach sometimes ruffled feathers, but I’ve accepted that it can’t be helped. As I tell every class: my job is not to be liked—it is to be effective.
The good news is: I designed this course to rebuild the students after deconstructing them. I took inspiration for this structure from my time at Techstars Austin in 2019-2020, as well as my closest advisors and investors, who effectively paced the push and pull with me. Part of the process involves helping the students build a thick skin, rewire how they think about market analysis, and convey their business effectively. As long as they recovered from the shock and worked with me to improve, they ended the semester in much better shape. It’s admittedly a delicate balance and an aggressive teaching style, so it tends to be suboptimal for students who just want a credit. But I’ve found that it still results in a net positive. Unsurprisingly, the top students have consistently thrived and grown rapidly with this style. And if it dissuaded some of the lower performers from rushing headfirst into a startup, that was likely for the best. I much prefer that over encouraging disillusioned students to continue their path and blow however much time, money, and energy on a venture that will probably never succeed. (Not to say they will never succeed, but perhaps they need more personal growth first, or at least a better idea.)
One caveat to this strategy, however, is that the instructor must bring strong credibility and earn respect to pull this off (otherwise, the students won’t feel driven to accept your criticism and push through adversity). I had two main advantages here:
- I had a prior exit and was an active CEO with my second company. The students knew I understood best practices and spoke from modern experience. Plus, good stories are entertaining.
- I was uniquely in the same generation as my students. This allowed my students and me to empathize with one another, bond easier, and unironically use Gen Z slang without getting side-eyed (no cap). The borderline peer dynamic seemed to help us slog through the course together. I don’t know if I’ll ever teach an academic course again, but if I do, I’ll certainly miss this aspect.
And yes, my final email did have a more positive ending:
However, if you decide that this path is for you, then chances are you struggle to imagine doing anything else. You desire to make an impact. You learn to accept that with great risk and pressure comes potentially unparalleled reward—not just financially, but also personally. Take comfort in knowing that even if your venture does not go as expected, you can still end with a net positive outcome (e.g., if you accomplish enough and get your name out there, you could more easily start another venture or get recruited into a relatively high role). In any case, I can attest that nothing makes me feel alive like startups do. I encourage you to understand your reasons for choosing this path and remember them when things inevitably become challenging.
Looking back, my proudest accomplishments in this course don’t involve the students who began the semester with existing momentum towards their idea. Those students were highly driven and fun to work with, but I argue that while they benefited from my guidance, they didn’t need me to succeed in the first place. Rather, my proudest accomplishments involve the students who began the semester unsure of themselves. Who had an inkling of a dream (and great potential) but lacked the confidence in themselves and their ability to navigate this daunting path. Pushing them to think bigger and take the leap has been my greatest joy. And it continues to be a joy when they reach out for help after departing my course.
To my (now former) students: thank you for making my professor experiences among my fondest memories. I hope that in the end, you found that I kept my promises.