Entrepreneur Office Hours - Issue #145
What if you could turn $25k into $100m?
I explained a couple months ago that I was cutting back on podcasts from weekly to monthly. Aside from freeing me up to work on other things, it also gave me more time to curate guests. I think you’ll be pleased with the result. Specifically, my latest guest on Web Masters is the one and only Jason Calacanis, well-known investor, host of This Week in Startups, and the man perhaps best known for turning a $25k investment in Uber into $100 million. Not bad, right?
Before Jason was one of the elite Silicon Valley investors, he was at the center of the East Coast tech scene running a magazine called Silicon Valley Reporter. Most people don’t know about that time in his career, but it was incredibly formative, and I was lucky that he sat down with me for an hour to talk about it. I hope you enjoy listening to the conversation as much as I enjoyed having it!
Everyone in the startup world has advice, but the good advice only comes from one place. (I promise the answer isn’t “Entrepreneur Office Hours.” Well… maybe it is…)
Today, Jason Calacanis is one of the most prominent names in the Silicon Valley tech and entrepreneurship community. But, before he was a well-known West Coast investor, Jason was at the center of the smaller bust fast-growing East Coast tech scene in New York known as "Silicon Alley." Hear him talk about that early NYC tech scene on the new episode of Web Masters.
…or search “Web Masters” wherever you listen to your favorite podcasts.
Office Hours Q&A
I was reading back through your old articles, and I noticed at one point you reference teaching a class for helping people find good startup ideas.
I feel like I am an entrepreneur in search of a good idea, but I struggle to find the right one. Could you please share one of maybe your best pieces of advice to your classes about how to find a truly great startup idea?
With much thanks,
I struggle with “one best” questions because I worry I can’t answer sufficiently without drastically oversimplifying things. In other words, lots of factors go into whether or not a startup idea will be successful, so, of course, I don’t want to imply there’s “one thing” that’s going to ensure startup success.
With that caveat out of the way, my two years of podcasting and talking with lots of successful entrepreneurs allowed me to zero in on one factor that seems to be one of the biggest predictors of startup success/failure, and that factor is: timing.
Simply put, a great idea is “great,” in part, because it’s being launched under the right circumstances.
Some people would argue that timing is “luck,” but that’s not entirely true. Yes, luck plays a role, but a savvy entrepreneur can (and absolutely should!) consider timing when making startup decisions in order to best position themselves to “get lucky.”
For example, look at technology and cultural trends. How is the world shifting and what directions are things going in? Understanding the basic trend lines of technological and cultural progress is critical for focusing on ideas that leverage emerging, growth markets where gaining initial traction is going to be easier.
You can also consider things like laws and regulations. As laws and rules change, it opens the door to new innovations and entrepreneurial opportunities that weren’t previously available, which means the markets for those innovations have lots more room for growth and less friction from incumbents (both helpful factors when launching a new startup).
I guess all this is a long way of saying my “best” piece of advice is to start by thinking about your timing. Ask yourself: “What’s changing in the world and how might that lead to new opportunities?” It won’t guarantee a good idea, but not having good timing will almost certainly guarantee you a bad outcome.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!