Ask Ash: 'Should I Go Into Business With a Friend?'

Dear Ash,

I want to start a travel company with my best friend—we work so well together, and we would have so much fun! Buuuuut, I’m also worried that if it doesn’t work out, it could seriously ruin our friendship. I know you have done several joint venture partnerships in the past: what’s your advice on going into business with a friend? Should I do it, or should I bite the bullet and just fly solo???

Sincerely,

Worried & Peeing Herself

Dear Worried & Peeing Herself (me too, most days),

Funny you should mention this: I’ve JUST been chatting with my very bestest biz babe Jamie Varon on an exciting new collaboration. (Shhh!) Which is to say, this topic is fresh in my mind—and I have plenty of advice to give: the good, the bad, and the ugly. (Definitely stay tuned for the ugly—you’ll never believe what I’m about to tell you.)

First of all, you’re absolutely right: working with a partner toward a business goal can be so fun, and so energizing, and so rewarding. (Even if you hate people, like me.) There’s something really energizing about working together as a team. (Even if you hate teams, like me.) You share the ups and the downs, you have someone to bounce ideas off of, you can brainstorm together, split the workload, bring different skills to the table, and feel like you are A PART OF SOMETHING. This is so weirdly lovely: when you work for yourself, it’s easy to feel isolated. This is especially true for nomads working from anywhere: not only are you professionally isolated, but you’re socially isolated in some ways, too, since you are traveling without your usual network. Having a biz partner can help alleviate a lot of that, since you’re working together regularly online, chatting, and working toward something bigger than yourselves.

Another pro? It’s way less scary. TEN THOUSAND PERCENT this is one of the biggest reasons people do go into business together: it alleviates a lot of the “holy shit I have no idea what I’m doing” feeling. Now, you can feel that together, with another person, and then blame them when it all goes wrong. (Actually don’t do that.)

But seriously: having a business partner can give you a little extra backbone to pursue the biiiiig stuff. You know, the kind of stuff you’re secretly dreaming about doing but it’s a little intimidating because who are you to do that??? And how would you do it all? And isn’t that a little nutty? On the other hand, with a partner in tow, everything feels more approachable. You guys can be nutbags together—and isn’t that great?

These are all reasons I LOVE collaborating. The energy! The enthusiasm! The teamwork! The sense of accomplishment! Plus, it’s really nice to have someone to share the burden with when the tech goes wonky, or a customer is unhappy, or the taxes are due, or the contractor disappeared. It’s also nice to have someone to share the expenses with, making some ventures more palatable for the ol’ bank account.

But these are things you already know.

You already know the good stuff. You’re already imagining how great it could be. Friends + business + money + passions = happily ever after, right? What could go wrong?

That’s exactly what I’m here for: to rain on your parade and your little Target rainboots.

Just kidding, Target rainboots are legit. But what I do want to do is help you understand the hard stuff about partnerships, so you can decide if you really want to go down this road (and make sure your friend is not a lunatic and can handle the hard stuff).

Because, lemme tell ya: there is ONE BIG THING that ruins even the best of partnerships, and it’s not what you think. Believe it or not, it isn’t money. It isn’t a mismatch of personalities. It isn’t different visions for the company. It isn’t that you’re bad at business, or they’re bad at business, or both of you are heinous freaks. (In other words, all the stuff you’re probably worried about.)

Rather, there is one super surprising, weird little detail that you you gotta get hammered out before going into business with another person, and I guarantee it’s the one thing you probably haven’t thought through yet. (Because none of us did in the beginning!)

In fact, most new partnerships never figure this out until it’s too late. (And you’re both pissed & writing passive aggressive emails.)

I’ve seen this happen way too many times: it’s happened to me when I was younger and less experienced, it’s happened to friends who are experienced, it’s happened to clients, it’s happened to the Pope.

Because you know the #1 thing that ruins every partnership I’ve ever seen?And the #1 thing you NEED to get right before you go into business with your friend?

Here it is—the surprising piece of advice you’d never guess:

It’s not setting appropriate. fucking. expectations.

GREAT EXPECTATIONS should be the name of every business partnership ever started, because you both go into it so optimistic, full of passion and energy and stamina and hope!

In your hopped up, punch-drunk state of rose-colored enthusiasm, you decide, while squirting champagne out your nose, that they’ll do the administrative stuff, the business stuff, the invoice stuff, the operations stuff, the practical stuff—and you’ll do all of the creative stuff, the marketing stuff, the sales stuff, the social media stuff, the happy horseshit stuff.

That sounds about right, right? Like every partnership that ever started???

Right?

RIGHT.

And also, so, so wrong.

Most people, when going into business together, decide roughly on each other’s responsibilities, just like that. It makes sense, right? Plus, you don’t know enough about the business yet to determine anything more specific, right?

Wrong again. (I love you.)

The real reason people get butt-hurt in partnerships—and those partnerships thus end up failing—is because of mismatched expectations about what the other person will be doing, how much of it they’ll be doing, for how long they’ll be doing it, and which results that person is responsible for acquiring.

To say that someone is going to “be in charge of marketing” is a really vague, weird, slippery thing. What does that really mean? Are you in charge of writing the newsletter? How many times per week? And how about social media? Where are you posting? When are you doing that? With what graphics? And what copy? Who gets to decide? Are you also in charge of the sales pages? And working with designers? And buying ads? And are you supposed to be publishing about your business on your personal channels? How many leads are you supposed to be bringing in per month?

To “be in charge of sales” is the same thing. What does that mean? How many hours per week are you dedicating toward this activity? What are you doing while working on this activity? Are you expected to be talking on the phone? Visiting clients in person? Going to conferences? Flying places? How often?During which hours? What about time with your family? Are you expected to work nights? What if your partner wants to work nights, and you aren’t available???

You see where I’m going with this.

While these all seem like details you can “hammer out later,” they are not. A partner’s job responsibilities need to be determined up front, and agreed on by both parties.

This is the only way you can both determine whether or not the other person is doing their job.

Because you know what happens if you don’t agree on this stuff up front???

Your partner’s gone all in on the business. They’re excited. They’re working 24/7 on the business. They’re fronting all the costs up front for the business. They’re doing SO MANY THINGS.

…and meanwhile, they’re sitting there fuming because you’re at your kid’s soccer game (again), on the phone with your daughter for 7 hours (again), prioritizing your other side hustle business (again), not getting as many sales in the door as you need (again), not dedicating 100% of your efforts (again), not appreciating how much capital you’ve spent (again), not contributing in the ways they expected you to (again), and generally being a big, fat disappointment that slowly builds into a seething rage that starts coming out in passive aggressive comments and ends in a total business explosion—and friendship explosion, too.

You could see how quickly that could spiral out of control, right?

There’s always one partner who’s secretly mad at the other partner for not acting the way they’d expected—even if, in your mind, you’re doing your job. Because that’s the real key here, isn’t it: feeling like you are both putting in an equal amount of effort.

^^^That, right there, will tank a partnership within weeks. If one person assumes you’ll be doing X, Y, Z, but you’re over here doing A, B, C, it’s a recipe for disaster.

ALAS, my dearest hopefuls, my advice to you is this: YES, go into business together! YES, get excited! YES, run with your wildest, most dangerous ideas!

But be a professional about it.

Sit down and outline each person’s detailed responsibilities, to the extent you are able.

Think of anything you aren’t thinking of.

Think of all the ways your partner could become resentful.

Think of all the ways you could become resentful.

Then, use those possibilities to form a plan for your partnership: what each person is responsible for, how many hours per week, during which hours, and with what results.

Also think through what happens if one person wants out. Or one person wants to spend money and the other person doesn’t agree. Or one person is frustrated that the other isn’t adhering to their agreed upon duties.

Make sure it’s all in writing.

Put it in your partnership agreement.

Or at the very least, make sure it’s documented in an email.

And start your partnership confident that you know exactly what you’re responsible for—and what your partner expects you to do—and vice versa.

Most people do not do this.

Most business partners end up resenting one another in a bitter flamey pit of hell.

But, it can all be avoided! And the BEST partnerships can happen. The key is avoiding unspoken resentment.

So, with that in mind: is the person you want to go into business with responsible enough to handle their duties? Will they be a person you need to constantly babysit? Will they be someone who lets you down? Could you see yourself getting angrier by the minute?

Or, are they someone who you know will be a good partner, and a good communicator, and faithful to their commitments, and mature enough to handle any differences with grace and an open mind?

What it all boils down to in the end, Worried & Peeing, is not whether your business partner will be a good business partner.

It’s whether you’ll both be able to be mature and respectful and communicative people, even when you aren’t.

With all my grit + guts,

Ash