Entrepreneur Office Hours - Issue #59

Why the most valuable resource in entrepreneurship will make you feel crappy

Being an entrepreneur means you’re probably a bit of a masochist. It means, in a weird way, you enjoy and embrace the inherent pain and suffering you’re surely going to experience. And that’s a good thing because, as I explain in this issue of EOH, embracing that pain is going to allow you to tap into one of the most valuable resources in entrepreneurship.

And while we’re on the topic of painful things, in this issue you’ll find a Q&A about hiring. You’ll also find an article where I share a strategy entrepreneurs can use to help them make difficult decisions. Sounds helpful, right?

But before you get onto the reading, I’ve got one little request. Medium — where you’ve probably noticed I do a lot of publishing — has created a referral program. You don’t need to register for any of the links I share. However, if you like what you read, and if you want to read other great content on Medium, consider registering for Medium using my referral link.

I’m not just telling you to do that because it make me money if you ultimately decide to subscribe (though I won’t complain about that part). I honestly love Medium. It’s got some incredible writers, it’s one of my favorite social media platforms, and, if you’ve gotten this far into EOH, I’m guessing you’ll like it, too.

Anyway — sales pitch over. Enjoy the rest of the issue!


Share Entrepreneur Office Hours

Why Great Entrepreneurs Thank the People Who Make Them Feel Terrible

What’s best for your startup might not always be enjoyable. Learning to embrace that discomfort could be the secret to your success.

A Simple Strategy For Helping Entrepreneurs Make Difficult Decisions

Entrepreneurs face lots of challenging choices. But making the right decisions doesn't have to be hard. You just have to know one thing.


Office Hours Q&A



Hi Aaron,

My company was able to raise its first round of funding, and we did it in order to be able to expand our team. We’re hoping to hire 2 or 3 more people. The problem is we’re having a lot of trouble actually hiring people or even getting good applicants.

I know there’s a hiring crunch everywhere, so I don’t think we’re alone. But, in our case, I feel like a lot of the issue is that a small startup like ours just can’t compete with bigger, more established companies.

What would you suggest we do? What’s the best way for small startups (less than 10 people) to recruit?

Thank you,



First, congrats on raising your round. I’m sorry hiring isn’t as easy as you’d like, but let’s call that a “good problem to have.” Better to be in a position of having the resources/need to hire and not being able to than not having the resources (or product demand) to hire.

(BTW… did you like how I’ve switched this to a “glass half full” question?)

As for the challenge of hiring as a small startup, you’re right that you’re definitely not alone. However, I’d frame the issue differently. You seem to think of yourself as competing with bigger, better-resourced companies for talent. In my experience, that’s not actually the case. In reality, the kinds of people who like working at bigger, more established companies simply aren’t the same as the types of people who like working at small, sub-10-person companies.

Sure, there’s some overlap. However, I suggest you avoid those “in the middle” people. Instead, you should focus your search on people who prefer working for tiny companies.

The next question is obviously: “How do I find those people?” True, it’s harder, but it’s not as hard as you might think.

If I had to guess, I’m betting you’re marketing for your position using more traditional strategies like job postings and career fairs. People applying to jobs online probably aren’t a good target for you.

Instead, the best way to find people who like working for tiny companies and early startups is networking and referrals. Start by spreading word about the job through friends. To be clear, I don’t mean you should hire friends. But let your friends know you’re hiring and ask if they know anyone who might be a good fit.

Another good strategy is to try poaching an early employee from a growing company. True, if the person already has a job, you’re probably going to have to pay more to hire them away, but… well… that’s usually the case for any good talent. The fact that the person currently has a job is a good sign that the person is employable.

The reason I suggest you target early employees from growing companies is because there’s a decent chance they joined their respective companies when they were small and prefer working at small companies. However, as their companies grow, they’re probably less happy and looking to get back to something smaller.

One last thing you might consider -- and I’m obviously biased here -- is to network with local university faculty. Every year I have a handful of students looking for jobs who fit the mold of “small company” types of people. They tend to struggle during recruiting season as their peers take jobs at Google and Goldman and Bain and whatever other monster companies, and, as the end of their senior years approach, they start getting a bit desperate.

I don’t mean you should hire desperate people. I just mean these are students who don’t necessarily fit the mold of working for big companies, but they don’t really understand that lots of great small companies like yours exist, you just don’t have the resources to attend university job fairs. However, every college professor knows a few students like this, and we want to help them. If we know about your job, we’re usually more than happy to pass it along.

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