Entrepreneur Office Hours - Issue #37

Should entrepreneurs hate themselves? And how important is great timing for a startup's ultimate success?

The more entrepreneurs I talk with, the more I’m convinced that timing is the most important factor in a startup’s ultimate trajectory. To be clear, I don’t mean timing is the only factor. I just think timing has an outsized impact on whether or not a startup succeeds.

I won’t get into my full argument here. Instead, in this week’s EOH issue, you’ll find two articles exploring the topic. Plus, my guest on this week’s Web Masters episode is Andrew Weinreich, founder of the first social networking website, and he talks about timing as well. Once you’ve checked everything out, let me know what you thin. How important is timing in startup success?

Also in this week’s issue, I explain why entrepreneurs need to learn to hate themselves. And, in the Q&A, I tackle a question about finding enough interest for your product.

Got questions of your own? Reply to this email and ask whatever you want to know.


I Became a Better Entrepreneur When I Leaned How to Hate Myself

The self-help gurus of the world want you to love yourself, but is that really the best thing for entrepreneurs? Find out why it probably isn’t.

The Lawyer Who Patented Social Networking

Can you name the first social networking website? It wasn't Facebook. It wasn't MySpace. It wasn't even Friendster or LiveJournal or Blogger. It was SixDegrees. And that's what you're going to learn about on this episode of Web Masters in a conversation with SixDegrees founder Andrew Weinreich.

Listen to Andrew's story on:

…or search “Web Masters” wherever you listen to your favorite podcasts.

Is Startup Success a Product of Great Timing?

Lots of people think timing is completely luck. I disagree. Having great timing as an entrepreneur is a skill you can cultivate, and this article will get you started.

Entrepreneur Who Built and Sold the First Social Network for $125 million Explains How He Did It

A follow-up article on this week’s podcast episode where I examine Andrew Weinreich’s strategy for identifying a business opportunity by focusing on — you guessed it — timing!

Office Hours Q&A



**Note**: This question comes from a comment on a Medium article where I give advice on how to find a market for a product you’ve already built. He’s specifically asking about a point I make about evaluating the success of an advertising campaign based on whether it drives a “significant amount of interest.”


Curious of your definition of [significant amount of interest]. My "one-size-fits-all" approach has been a 2% click-through rate. How would you define "significant amounts of interest" in a quantitative way?

- Adam


I definitely understand why specific numbers would be helpful here. Unfortunately, like most things in the entrepreneurial world, context controls meaning, so there’s not a “one-size-fits-all” answer. As a result, I’m going to have to be frustratingly un-quantitative in my answer.

To me, “significant interest” is a personal choice for entrepreneurs because it’s inherently tied with what the entrepreneur perceives as valuable. After all, the things I care about in life, and my goals for pursuing a given venture are going to be completely different from the things you care about and your goals.

For example, let’s imagine I’m an entrepreneurial scientist/researcher interested in treating diseases. Objectively, I’d probably want to tackle the biggest disease possible because that’s going to help guarantee me a large market. Using this strategy, I might explore entrepreneurial opportunities surrounding conditions like diabetes or heart disease because being able to help a large number of people is going to factor into how I calculate significant interest.

Now imagine my wife suddenly gets diagnosed with an extremely rare disease that only affects

a few thousand people. At that point, the parameters around what might qualify as “significant interest” completely change. I’m going to focus my attention on my wife’s disease because of how invested I am in helping her, and my calculations for significant interest will be impacted accordingly.

In other words, assessing whether or not I’ve identified a market with a significant amount of interest is something I -- and all entrepreneurs -- have to determine largely based on personal goals. It can’t be quantified in a “one-size-fits-all” manner because every entrepreneur has different goals.

This, by the way, is why I tell my students that the first step in any entrepreneurial process -- or, honestly, any life process -- is to set your goals. Your goals are your “north star.” They help guide you through the hundreds of decisions you’ll have to make. That’s particularly helpful when building startups because of how rarely you’ll find “one-size-fits-all” answers.

Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!