Wealthsimple makes powerful financial tools to help you grow and manage your money. This is the latest installment of our "Dear Ms. Etiquette" series, in this edition The Financial Diet guest-answers your money questions.

Dear Chelsea,

How long should I support my boyfriend while he's doing his "startup"? How do I even broach that conversation with him? And what are the factors I should be considering?

Supportive Within Limits

Dear Supportive,

I have to be honest: this question feels a little awkward for me, since I have been through nearly this exact scenario. Only in my case, I was the boyfriend and my now-husband was the person who very likely thought at many points throughout the first two years of launching my small business that he (and I) was making a grave mistake. When I started The Financial Diet, my co-founder and I quit our jobs in advertising and media, and we did it before the business was even remotely profitable. And not only did Marc, then my boyfriend, support me unconditionally, he even took a paid sabbatical from work to help us build our site’s ad infrastructure. He was as all-in as a person can be and for those two years the only meagre earnings I brought in were from freelance work while I put everything we made from TFD back in the company. He never once made me feel guilty or ashamed. We continued to invest together emotionally while he invested financially by being the major breadwinner — not to mention providing health insurance, and being the only contributor to our retirement. That, more than any editorial skill or intelligent business decision, allowed TFD to be possible, let alone healthy and profitable. So you’ll understand when I say it’s hard not to feel some outsized empathy for the boyfriend in your question. A stable, supportive, and financially-secure partner at home is the greatest gift any entrepreneur could ever be given. (Well, perhaps a close second would be a distant relative being hit by a bus and leaving a sizable fortune with no emotional strings attached.)

If the success of the business isn’t as important to you as helping him go after something he’s passionate about, it’ll still be important to figure out how long you want to support him, and then say it out loud.

That being said, all of those gifts he gave me in the early days were gifts that he could afford to give. His earnings were enough to support the two of us, his insurance covered me, and he was able to make this decision without completely compromising his own goals — financial and career. So that’s the first relationship stress test you need to pass: can you afford to help your boyfriend? Are you able to support the two of you for as long as it’ll take for the business to get off the ground — several months or potentially years? Do you even think his startup is a good idea? And does it matter to you if it’s a good idea or is it OK if it’s just his passion project? (A friend who went along for the ride with her boyfriend on a very poorly-conceived startup found that her every waking day was a practice in biting her tongue so as not to scream, “YOUR APP IS BULLSHIT” across the coffee table, and that wasn’t a job she liked having.) Are you willing to make some serious downgrades in lifestyle? Is his making this choice going to derail some of your important financial goals, like debt repayment? If those answers aren’t good, you probably have a hard conversation ahead of you.

It’s about more than just the money, of course. There’s an emotional component to this, too. There were times when prospects for TFD seemed bleak and my husband probably cringed inside thinking that he had made the wrong financial bet. But he never made me feel that way. And if he had (or even if he’d repressed those feelings), it would have caused vastly more tension in our relationship. Are you emotionally ready to support him even through what are likely to be some fairly bleak early days? My advice is, don’t go into this grudgingly. You have to do it with enthusiasm and a full heart. It’s easy to fantasize about the bohemian (start-up) life wherein a couple is happy to scrape by on love alone so one partner can pursue their far-flung dreams. But if we’re being honest, living that way can absolutely suck in practice.

Are you emotionally ready to support him even through what are likely to be some fairly bleak early days? My advice is, don’t go into this grudgingly.

If your answers to those questions are positive and it’s feasible for you to support him, it’s well within your rights to require that this agreement be treated like a business plan, with the requisite degree of seriousness. Don’t feel guilty — sitting him down with a simple, “I love you, I want to do this with you, and I want to make sure we do it right,” is an incredibly generous gesture. If the success of the business, or your belief in its viability, is important to you, you’ll want to layout a clear-headed idea of the business itself and how it is intended to become self-sustaining. In the case of TFD, I had long worked in the industry in question and was very familiar with how exactly we would monetize and grow our platforms and that was reassuring to my partner. I presented a solid business plan to him, with timelines and numbers. It’s the least he can do and it will allow you to form a coherent idea of how long you can realistically afford to support him and a fair cutoff point if he has not yet reached a place of earning steady money.

If the success of the business isn’t as important to you as helping him go after something he’s passionate about, it’ll still be important to figure out how long you want to support him, and then say it out loud — there should be an explicit timeline from the beginning so that it doesn’t drag on forever, past the point of being a reasonable financial decision for you.

And an important note: it appears you two are not married and therefore have no real financial obligations to one another. You should consider the idea that, as someone who is not a spouse, you may want to receive some kind of ownership stake in the business in exchange your financial support. That’s the agreement I came to with my partner since we were not married at the time and the fact that I was treating him fairly made his decision to support me feel healthier and more like a true investment. And now he owns a meaningful percentage of a profitable company! Win-win. The conversation of ownership, compensation, or at the very least financial recognition should be had along with the timeline. It’s not inappropriate or greedy, and will help make your risk-taking here feel more equitable.

All of that said, though, there will never be a perfect system. Even with the best business plan, there’s always risk; even if you have a stake you’ll still wonder about putting your financial life on hold sometimes. But what you can do is make sure that you are a part of his plans, that you are given the consideration and respect that any early-stage investor would be (which is what you are), and that you are never in the dark about the decisions he is making. You can do this as a team — a true partnership. And if you both go into it with the right combination of optimism and pragmatism, your support can be the key thing that helps him knock it out of the park.

– Chelsea, from The Financial Diet

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