Entrepreneur Office Hours - Issue #8

Entrepreneur-ing during the holidays, building pocket universes, and rejecting overnight success

It’s the holidays and, let’s be honest, nobody is actually reading this issue. Why am I even wasting my time putting it out? Well, I’m hoping some small portion of you are like me: you secretly (or not-so-secretly) hate holidays because they prevent you from getting work done.

Don’t be ashamed! I love working, too. That’s a big part of what makes us entrepreneurs. We don’t dread going to work in the mornings. Instead, “work” is a big part of what gets us excited to get out of bed.

So this issue of Entrepreneur Office Hours is a special post-Thanksgiving issue with tips, tricks, and advice for how to keep entrepreneur-ing during the holidays.

If you know anyone else working today — or who wishes they were working — forward this email along and invite them to join our community. And, even though it’s the holidays, I’m still answering your questions about startups because that’s what I enjoy doing. So reply to this email, @-me on Twitter, or message me on LinkedIn.


How Entrepreneurs Can Make Holidays More Productive

Trying to figure out how to optimize your holiday work schedule? Here are some tips for making the holidays at least feel a little more productive.

Philip Rosedale - The Physicist Who Built a Pocket Universe

If you were born by 1990, there’s a good chance you’ve heard of Second Life. In 2006, over 600 articles per day were being written about it. And even though virtual worlds like Second Life haven't become as popular as people once thought they might, the featured guest from the latest episode of Web Masters thinks we're still only at the beginning. His name is Philip Rosedale, and he's the founder of Second Life.

Listen to his story on:

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

How to Train Yourself to Ignore the Myth of Overnight Success

From an outside perspective, successful startups often seem like they were overnight successes, and it causes entrepreneurs lots of anxiety. It’s also rarely ever true. In order to avoid the stress of thinking other companies are growing faster thank yours, you have to train yourself to ignore what appears to be overnight success.

The Two Simple Steps for Successfully Cold Emailing Venture Capitalists

I liked the Q&A from EOH Issue #7 so much, that I turned it into its own article. In case you missed that advice on how to successfully cold email venture capitalists, here’s a more polished version.

Office Hours Q&A



I hate trying to fundraise during the holidays.Every year, like clockwork, from the week of Thanksgiving to the week after New Year’s, I feel like every investor basically shuts down and it becomes impossible to get any meetings. Why is this? Who can afford to just shut down their businesses for almost two months? Any advice for how to fundraise effectively during holidays?

- Drew


Great question! Back when I was constantly fundraising, I always hated the strange between-holidays time period, too.

To be fair, it’s not just VCs who seem to disappear from Thanksgiving to New Year’s. Customers and employees are harder to deal with, too. In my B2B companies, we always offered bigger discounts during October deal negotiations just because we knew it was better to try to close a sale before November than risk losing it once the holidays rolled around and people got distracted.

For what it’s worth, even now that I’m doing less business building and more content creation, I see the same trend. My readership stats trail off, my podcast listeners dip, and I’m not even sure anyone is going to read this issue of Entrepreneur Office Hours.

And that brings me to my answer, which is: you accept it as something beyond your control.

I realize this is an unsatisfying answer. As entrepreneurs, we like to think that, if we work hard enough, we can bend anything to our wills. Unfortunately, like everything else related to entrepreneurship, there’s no magic solution. However, there is a smarter approach.

Since the hardest thing to do in entrepreneurship is convince people to change their behaviors, when possible, the better approach is to adjust your own strategies. For example, since I know less people are reading content about entrepreneurship between Thanksgiving and New Year’s, I’m not going to spend the next six weeks trying to convince people to skip Christmas dinner in order to read my Medium articles. I’m just not going to put out as much content. Instead, I’m going to use the extra time to build a back catalog of content I can share once readership picks up again.

You can do this for fundraising, too. Since you already know investor meetings are difficult to schedule in November, December, and January, account for that drought ahead of time.

For starters, never have an open fundraising round at the end of the year. For what it’s worth, Summer is also a bad time to fundraise. Instead, always plan to start fundraising either in mid-February or mid-August. It’s not a guarantee of success by any means. And it’s also not impossible to fundraise at other times. But your odds of success will be better if you pay attention to the calendar and fundraise when more investors are writing checks.

Second, plan your own work calendar around the holidays. By that I mean if you know you won’t be able to effectively fundraise or reach customers from Thanksgiving to New Year’s, and you also know your own employees will be taking lots of vacation during those times, then save time-intensive projects that don’t require other people for the holidays. Personally, back when I was running my companies, if I had any big coding projects on my plate, I usually tried to push them to the holidays (or mid-summer) when I knew I could lock myself in my office without being disturbed and nobody would miss me.

And third, use the time to prepare. After all, if we’re honest with ourselves, fundraising doesn’t mean constant investor meetings. A big part of fundraising involves building decks, crafting pitches, researching investors, hunting down email addresses, and so on. Those are all things you can do ahead of time. So spend the next couple months figuring out who you want to talk to, find their contact info, pre-draft your emails to them, then start practicing your pitch. By the time February comes around, you’ll be well-prepared and ready to fundraise.

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