The Glamorous Life of an Entrepreneur (Spoiler: It's Mostly Sweat and Rainstorms)
Entrepreneur Office Hours - Issue #287
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A few days ago, I was visiting another college’s campus and making some videos. It was the latest stop in my ongoing summer adventure of traveling around and creating content about universities, teaching, and entrepreneurship. On paper (and, let's be honest, on social media), it probably looks like a dream gig — exploring beautiful campuses, engaging with interesting people, and sharing entrepreneurial insights along the way.
But let me paint you the less glamorous picture of what this day actually looked like.
For starters, it was about 95 degrees and miserably humid. And by the way, I wasn’t strolling leisurely around campus in shorts and flip-flops. Nope. I was in full professor mode: tweed blazer, dress shirt, tie, and dress shoes. I parked in a visitor lot, which apparently was located in another zip code, so it took me forever just to reach the center of campus. And because I'd never been there before, I spent a good chunk of time wandering in circles, missing turns, getting confused by poorly marked paths, and basically hiking in clothes better suited for lecturing than trekking.
After several sweaty hours of filming, re-filming, and talking to myself into a camera while confused students hurried past me wondering who the weird professor guy was, I finally started heading back to my car. Just as I was thinking, "Well, at least the hard part's done," the sky opened up in a sudden, torrential thunderstorm.
Within seconds, I was completely drenched. Not just wet — soaked through to the bone. Tweed blazer dripping, shoes squishing, and my phone precariously clutched beneath my jacket in a desperate attempt to save my footage.
When I finally reached the car, I collapsed into the driver’s seat, took one look at myself in the mirror, and burst out laughing. I looked exactly like what you'd imagine a professor would look like after walking through a monsoon in a full suit. It was absurd. And, of course, nobody was around to see it.
As I sat there dripping and laughing, I found myself thinking about how perfectly that moment captures the reality of entrepreneurship and underscores the messy, awkward, uncomfortable moments nobody ever sees. Social media and startup mythology tend to emphasize success stories: the slick pitches, the polished products, the glamorous funding rounds. But those moments are the highlight reels. What they miss are the countless sweaty hikes, the sudden rainstorms, the long, tedious hours spent wandering around feeling completely lost, thinking "What the heck am I even doing?"
I'm sharing this less-than-flattering story because, if you're an entrepreneur, you need to know you're not alone. If you've ever sat soaked, confused, exhausted, or frustrated (literally or metaphorically) you need to remember: every entrepreneur goes through those moments, even if they don't show them publicly.
The real measure of entrepreneurship isn't how good you look on stage or online. It's how quickly you can laugh at yourself when you're sitting in your car, drenched, wondering what just happened, and still decide to go back out and do it all over again.
-Aaron
This week’s new articles…
The Only Word You Can Trust in Entrepreneurship
People are going to tell you lots of things during your startup journey, but there’s only one word you should pay attention to.
What if Being Friends With Your Co-Founder Is Killing Your Startup?
Startup co-founders have a special type of relationship, but is it possible to get too close to your co-founders?
Office Hours Q&A
QUESTION:
Hi Aaron,
I moved to the U.S. a few years ago and I’m now trying to build my own business here. Back home, I ran something small, but the way things work here feels very different. I’m working hard to adjust, but sometimes it feels like I’m missing something important. Maybe something about how people think or how they expect things to be done.
So my question is: When you’re starting a business in a new country, especially one with a very different culture, what do you think are the most important things to focus on first?
Thanks for everything you share,
Ali
For starters, thanks for the trust behind this question. I’ve never had to do what you’re doing. I’ve never tried to start a company in a country where I didn’t grow up, didn’t speak the language natively, didn’t understand all the social cues or unspoken expectations. Honestly, even just moving to a new country and making a life for yourself is an enormous feat. Doing that and trying to build a startup? That’s a level of courage and determination most people will never fully appreciate. So I just want to say: I see you, and I’m impressed.
As for your question, having not been in the situation, I don’t feel like I have a clean checklist to offer. In fact, in a case like this I might be smarter to just skip the question since I’m clearly not the expert. However, I feel like I have a few thoughts that might help you shape your thinking as you go, and I figured I’d share them.
If it were me, I think I’d focus first on becoming a really close observer. Culture is invisible until it isn’t. And when you’re coming from another place, even little things — how people say no, how they handle conflict, how they show excitement, how they make decisions — can throw you off. So maybe the first job is almost anthropological: watching, listening, noticing what people respond to, what feels familiar to them, what makes them curious or hesitant or confused.
And second, though this might sound contradictory, I’d think hard about what not to change. Just because you’re in a new place doesn’t mean you have to erase where you’re from. Some of the best businesses come from that blend where you bring something different to a culture and it feels refreshing, not foreign. So yes, learn the norms. But also protect your instincts. There may be something powerful in the way you see the world that your customers haven’t experienced before.
Finally, I’d try to find others who’ve done this too. Not necessarily to get advice, but just to not feel alone. There’s real power in community, especially when the rest of the world feels unfamiliar.
I don’t know if that helps. Like I mentioned, I haven’t walked your path. But I’m rooting for you. And I hope you’ll keep building, keep watching, and keep trusting that there’s real value in your perspective even (maybe especially) when it feels different.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.