AITAH for Not Wanting to Help My Friend Start a Business?

I never thought I’d be questioning a 10-year friendship over something like this, but here we are. My best friend since college wants me to be their unpaid marketing director, accountant, and emotional support animal for their new “passion project.” And when I hesitated? Well, let’s just say things got awkward.

Before you judge me (or them), let me walk you through exactly what happened—because I genuinely can’t tell if I’m being reasonable or if I’m about to lose my oldest friend over this.

The Business Pitch

Last month, Sarah (not her real name) invited me to dinner at our favorite sushi place. I thought it was just a catch-up session until she slid a 32-page business plan across the table. Her dream? An eco-friendly yoga studio with a vegan juice bar. Admirable? Absolutely. Realistic? Well…

Here’s the kicker: She wanted me to handle all digital marketing, redesign her website (“since you’re good with computers”), and help with bookkeeping—all while keeping my full-time job. Her offer? “5% equity and free smoothies.”

My Immediate Concerns

My stomach dropped harder than Bitcoin in 2018. I’ve seen Sarah’s track record: three abandoned Etsy shops, that ill-fated dog-walking app idea, and the essential oil MLM phase. Each time, I’d spent dozens of hours helping before she lost interest.

This time felt different though. She’d actually rented a space and signed a lease. But when I asked about her financial runway? “I figured we’d crowdsource if needed.” Her marketing budget? “That’s why I need you!” The business license? “Is that really necessary at first?”

The Friendship Factor

Here’s where it gets messy. Sarah isn’t just any friend—she was my college roommate, my bridesmaid, and the person who nursed me through my divorce. But that’s exactly why this feels dangerous. If this venture fails (statistically, it probably will), will our friendship survive the resentment?

When I gently suggested she hire professionals instead, she teared up: “I thought you believed in me. I’d never say no to you.” That guilt trip has been sitting in my gut for weeks.

Professional Boundaries

As a marketing consultant, I charge $125/hour for the services she’s requesting. Doing this for free wouldn’t just cost me time—it would set a precedent with other friends and devalue my expertise. Yet when I mentioned this, Sarah scoffed: “Since when do friends nickel-and-dime each other?”

Worse? She’s already told mutual friends about our “exciting collaboration,” putting me in this awkward position where saying no makes me look like the villain.

Alternative Solutions

I’ve tried compromising:

• Offering a one-time strategy session to point her in the right direction
• Creating a list of affordable freelancers
• Even suggesting we revisit this in 6 months if she hits certain milestones

Each suggestion was met with some version of: “I need you now, not later.” Yesterday, she sent me a Venmo request for $500 as my “initial investment.” I haven’t responded.

The Emotional Toll

What hurts most is realizing our friendship might have been conditional this whole time. The moment I set boundaries around my time and skills, I became “just like everyone else who doesn’t support my dreams.”

I’ve lost sleep over this. Part of me wants to cave just to preserve the relationship. But another part knows that real friends don’t weaponize guilt or demand professional favors worth thousands of dollars.

Your Verdict?

So tell me honestly—am I the asshole here? Should I:

1. Swallow my doubts and help despite the red flags?
2. Stand firm but risk losing the friendship?
3. Offer a middle ground I haven’t thought of?

Comment below with your take. Have you been in this situation? How did it turn out? I’m desperate for perspective before this blows up any further.

And if you think I’m being unreasonable? Well… I guess I’ll start practicing my smoothie order.