The original article, 5 awkward situations you’ll have to navigate as a first-time entrepreneur, was shared to me by Joe Koufman. I decided it would be a great #blindpost, and in the spirit of the #blindpost rules, I did not read the article but instead took the title and wrote my interpretation of it.

As an entrepreneur, you’ll have a lot of awkward moments. But as a first-timer, yeah it gets awkward a lot.

Stumbling through your “elevator pitch”.

You’ll get asked this question a lot: What does your business do? And if you don’t have a solid answer ready, you’ll look (and feel) foolish. It’s tough to nail it and even tougher to feel confident delivering it. But it’s necessary for your employees to hear you nail it, as well as potential customers and investors. Stumbling through talking about your business will not inspire confidence in anyone. The best solution: practice, practice, practice.


Having to fire one of your friends.

As a young entrepreneur, I realized the hard way that if you’re going to hire your friends, or become good friends with the people you hire, then you are setting yourself up for very awkward situations. I don’t have a good answer to this one. I enjoy working with my friends, so I’m always setting myself up for a fall. Fortunately, I try to only hire friends that are bad&ass at their jobs, so that reduces the chances I’ll have this problem ;)

Struggling to pay your bills/employees.

This one is rough. In most small businesses, there are times when cash flow is tough and you have to either pay bills late (and deal with frustrated vendors) or ask employees to get paid late. My only advice here is to put your employees first, always, and deal with frustrated vendors. But most importantly, keep a tight eye on cash flow so that you minimize the amount of times you have to deal with this.

Partner/co-founder struggles.

Yikes, this one can be tough. If you have a partner or co-founder(s), and I usually recommend that you do, there will be awkward conversations along the way. How much stock does everyone get? Who really is THE boss? How do you give constructive criticism? How do you receive it? Who gets paid how much and why? The best solution here is to always be quick to have honest and open conversations. Just put it on the table and get it out in the open, and if your partnership is strong, it will work out for the best. Have those talks early and often.

Not knowing what kind of benefits you have.

Remember that scene in Jerry Maguire where he’s asked by his new (and only) employee, “We’ll have insurance right?” And he says, “Yes of course…..I don’t know.” Benefits, who has time to think about benefits? Your employees, that’s who. But as a first-time entrepreneur, you might not have your hands around all of those details right out of the gate. “What’s our vacation policy? Do you have plans for a 401k? How much time do I get off for maternity leave?” If you get asked those questions and don’t know the answer, just roll with it. Or fake a seizure or something and then go figure it out real quick. 


Here is a recent #blindpost I wrote, The two traits every entrepreneur needs. And here are more #blindposts you can check out. And a handful of my friends will suggest blindposts for me to write from time to time, please feel free to do that too!