Entrepreneur Office Hours - Issue #95

Y’all are the best. Seriously: THE BEST.

In my last issue, I asked for help sharing an article I wrote because it would help raise money for children with heart conditions (like, as I explain in the article, the condition my daughter has). Boy did you all deliver!

For the past few days I’ve been seeing tons of links across Twitter, Facebook, and LinkedIn, and I’m sure you all have been a huge part of that. Thanks! I’m incredibly grateful for the support. Thousands of people have already read the article, and it’s still getting tons of new readers every minute.

By the way, if you didn’t have a chance to share it but still want to help, here’s a link:


Moving on to this issue of EOH, it’s hard not to get excited by the guests I pulled in on this week’s episode of Web Masters. I tracked down Jane Metcalfe and Louis Rossetto, the co-founders of WIRED Magazine. Yup… that WIRED magazine. Pretty cool huh? Talk about tech royalty.

Enjoy the episode, enjoy this issue’s articles, enjoy the Q&A, and, thanks, again, for all your support.


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The Partners Who Published the Mouthpiece of the Digital Age

A magazine might seem like a strange way of teaching people about the Internet, but that didn't stop WIRED Magazine from becoming the mouthpiece of the digital age. Hear how it got started on the new episode of Web Masters featuring WIRED's founders, Jane Metcalfe and Louis Rossetto.

Listen now on:

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


The Naive Mistake You Don’t Want to Make When Pitching Your Startup

I can’t help but look back on some of the decisions I made about how to pitch my startups to venture capitalists, and I just want to hide my head in shame. In this article, I share one particular pitch strategy I thought was brilliant but actually made my company look terrible.

Office Hours Q&A



Hi Aaron,

I read your story about your daughter and about how unexpected life events can create big problems for startups. I’m dealing with something like that now. I don’t mean to imply it’s as bad as what you’ve had to deal with in relation to the sickness of a child, but it’s definitely causing problems for my startup.

My co-founder is going through a very messy divorce, and it’s clearly affecting his ability to work on our startup. He’s not able to spend as much time working, and, when he is working, he’s noticeably distracted and not firing on all cylinders.

We’re equal partners, so I can’t kick him out. I also wouldn’t want to. I actually understand where he’s coming from because I went through something similar a few years ago, before our company. I honestly just want to know how to best help him while not damaging the company.

Regardless, we can’t continue much longer on our current trajectory. Something has to change. I can’t keep doing his job and mine. There aren’t enough hours in the day, and it’s going to cause us to fail.

- Silas


First, to be clear, one entrepreneur’s tragedy and hardship doesn’t need to be “not as bad” as another’s. They don’t even need to be compared, and that definitely wasn’t the purpose of my article. The purpose is actually exactly what you’ve brought up here, which is that all sorts of unexpected life events happen, and they cause problems.

Regardless of the cause, what you’re describing here is the same basic circumstances of what I describe in the article. Back when you and your co-founder launched your startup, everything was great in both of your lives. But now your co-founder is going through something terrible and tragic, and that’s taking a huge chunk of his time and attention.

To be honest, it should be taking his time and attention. What he’s dealing with is important. As much as I hate to tell you this, it’s more important than your startup.

From what you’ve written, it sounds like you already know and understand that. I’m glad to read you’re not trying to pressure him into working more than he’s currently capable of, and I’m glad you want to help him as best you can.

What’s best for him might very well be to shut down the company. Again, I realize that’s not something you want to read, but it’s the truth.

Your other option, of course, is to continue plugging away without your co-founder’s full commitment and hope you can keep things afloat with you doing the majority of his work, too. Is that sustainable for you? You’re obviously the only person who can answer that question. Just remember, the timeline for your co-founder to return is unpredictable. He could be back and operating at full capacity in the next month. Or it could be a year. Maybe never.

Are you able to operate with that kind of uncertainty?

Honestly, you shouldn’t have to. I know it’s hard, but we all need to understand that life is unpredictable, and we can’t always control the things that happen to us. When bad things happen – and they will – often the best thing we can do is learn to be flexible. That means letting go of our original plans and ambitions – whatever they may have been – and adapting to a new reality and a new set of circumstances.

Your startup – at least in its current form – might not exist in that new reality. If it doesn’t, that’s not a failure. It’s a learning experience. You’ve certainly learned a ton from all the work you’ve already done, and, whatever happens next, you’ll be able to bring those lessons with you. I guarantee they’ll make you more successful in the future.

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