Entrepreneur Office Hours - Issue #86
Sometimes, entrepreneurship is counterintuitive, and that can be frustrating
I’m often fascinated by things that are counterintuitive — things that seem like they’re true but aren’t, or things that seem like they shouldn’t work, yet they do. I sometimes wonder if my interest in counterintuitive things is part of the reason I enjoy studying/teaching entrepreneurship. Over the years, I’ve noticed how things that “work” in startups tend to be the exact opposite of what I originally thought, or vice versa.
That’s the theme of this issue’s featured article. I offer three examples of things you think are true about customer acquisition, but they actually aren’t. For what it’s worth, I also try to offer an explanation for why entrepreneurship has all of the counterintuitive quirks. Let me know if you have a better explanation.
When you’re done reading that article, you can head over to LinkedIn, where I’ve shared a post about how entrepreneurs can use the 7 Deadly Sins as a framework for thinking about startup success. Because… umm… why wouldn’t you want to do that?
And this issue’s Q&A is about pitch competitions. You all know I love any question about pitches. But — spoiler alert — I’m not such a big fan of pitch competitions. Read on to find out why.
3 Business Strategies You Think Are Good for Growing Your Startup That Actually Aren’t
Getting new customers for a startup is hard when you’re following strategies meant for different types of companies.
Are the 7 Deadly Sins the Secret to Startup Success?
I was speaking with a successful entrepreneur who told me: “To get good at acquiring customers, learn to embrace the seven deadly sins.” After he said it, I didn't bother to ask him what exactly he meant, and I've been trying to figure out ever since. This article is my best guess...
Office Hours Q&A
I feel like I’ve spent a lot of time over the years preparing for pitch competitions and pitch events, and nothing ever comes from them. Even when I’ve “won” them, they still seem to be pretty useless. Especially in relation to the amount of time they take to prepare for.
I know you’ve mentioned that you’ve done a lot pitch competitions. What’s your take on pitch competitions? Are they worth the time and effort?
I’ve had the same thoughts about pitch competitions plenty of times.
During my years of building startups, I spent more hours than I’m proud to admit preparing for pitch competitions. I won my share, too. But nothing significant ever came of those victories. I think I took home a few thousand dollars in reward checks and some “free” services (e.g. hosting credits on AWS or something like that). Definitely nothing world changing.
To be fair, maybe other people’s experiences differ. I obviously can’t speak for every pitch competition in the world. Perhaps I could have (or should have) found better competitions.
I guess my advice here would be to tell you to be careful, thoughtful, and selective about which competitions you choose to participate in and why.
In my experience, anything described as a “competition” wasn’t worth my time. However, pitch events with investor audiences (assuming I was fundraising) were the better opportunities. I don’t mean you should expect to pitch in front of a bunch of investors and walk out with a check, but investor pitch events are good places to get in front of lots of investors at the same time (I love efficiency!) and find a handful of investors worth having follow-up conversations with.
In fact, I met more than one of my eventual investors via pitch events. Again, I didn’t get checks directly from any particular pitch event. Instead, the events served as valuable introductions, then I continued talking with a few of the investors I’d met, and, eventually, a handful invested. It wasn’t a quick process by any means, but the outcomes were worth the effort.
So I guess that would be my advice. Avoid competitions. They’re mostly created for the good of the people hosting them, not the good of the participating startups. But don’t avoid pitch events. The competitions are more spectacle and time waster. The events are for serious business.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!