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Entrepreneur Office Hours - Issue #153
Would you buy a 10 cent piece of candy for $100?
I got to choose the title of the first entrepreneurship class I ever taught, and I decided to call it “Learning to Fail.” If you’re an experienced entrepreneur, you know exactly why. Entrepreneurship is a series of failures, and successful entrepreneurship is a byproduct of understanding those failures, learning from them, and then trying again based on your new knowledge.
As much as I love helping my students learn from their failures, I also experience plenty of screw ups in the class because I’m as prone to failure in the class as my students. One of those failures led to the story I’ve shared in this issue’s featured article. It’s about what happens when you challenge your students to sell a Jolly Rancher — a cheap piece of candy — for an exorbitant price.
While I’m on the subject of failure, I’ll also highlight this issue’s Q&A, which, in its own way, also deals with failure. Specifically, it’s a question about the unglamorous side of entrepreneurship.
Umm… yeah… where do I begin? Maybe I’ll start with all the epic failures…
Apparently, people will buy anything no matter the cost. All you have to do is figure out the right sales pitch.
Investors aren’t always great at telling founders what they’re really thinking, and founders aren’t great at listening carefully.
Office Hours Q&A
What’s the unglamorous part of entrepreneurship?
This was an IRL office hours question (as opposed to a question someone emailed), but it was so adorable, I felt like I had to share it.
What’s the unglamorous part of entrepreneurship? Umm… EVERYTHING!!!!!
For me, the question illustrates the fundamental misperception between what people perceive entrepreneurship to be like and what it’s actually like.
Before I start lamenting how challenging an entrepreneur’s life is, I want to be clear about one thing: getting to be an entrepreneur – especially the type of entrepreneurship I discuss – is an enormous privilege. I don’t mean it’s always easy or fun or glamorous or anything like that, but, in order to do it, you have to have some level of flexibility and freedom. That’s not to suggest everything is perfect in your world or that you’re rich beyond comparison. However, you’re probably not dealing with some immense tragedy or hardship. For example, you’re not battling stage-four cancer right now; you’re not cowering in a basement because air raid sirens are going off all around you; you have electricity and Internet, a decent phone, etc.
So… yes… I’m incredibly privileged I’ve gotten to be (and, in some cases, still get to be) an entrepreneur. But that doesn’t make the work glamorous. The vast majority of my work is exhausting, frustrating, time-consuming, expensive, and it almost never goes how I envisioned it. However, I can see how, on the outside, people might think the work is glamorous, which is what the above question is demonstrating.
For example, you might imagine securing a multi-million-dollar round of venture capital is glamorous. After all, large amounts of money are things “rich people” have. But, raising lots of money from venture capitalists doesn’t mean you’ve suddenly got millions in the bank to do whatever you want. It means you A) probably needed that money; B) spent lots of time (and frustration) trying to get that money; and, C) now have an enormous burden on you to accomplish something unfathomably difficult using what is, to you, an amount of money that’s not nearly as much as you’d like, want, or need.
Maybe, when you’re thinking about entrepreneurship, you’re imagining someone like Elon Musk standing in front of a huge crowd, sharing his vision with the world. That seems glamorous, right? Except… umm… no. Giving compelling talks to large audiences takes tons of prep work. If you want to be exceptional at it (which Elon Musk is not), you’ll spend months preparing for a 10 minute speech. Plus, when it’s all over, you’ll most likely find yourself working late into the night trying to catch up on all the work you missed by giving that talk.
Even this newsletter, which we might call my current entrepreneurial venture, isn’t glamorous. Sure, I’ve got a large audience of people who want to read my thoughts every week. And, to be clear, it’s wonderful, and I value all of you immensely. But I’m also writing this answer at one o’clock in the morning the night before this issue of EOH publishes. I’m exhausted, and I’d really like to go to be right now, but I can’t because, after I finish writing this answer, I’ve got client proposals to finish reviewing and somewhere between 10 and 10,000 emails to answer.
To be clear, I love every second of being an entrepreneur… even the exhausting seconds. But glamorous? No.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!