9 Brutal Lessons We Learned About Business Partnerships
par Cara Kapler
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Business partnerships are like marriages—exciting in the beginning, but full of challenges that will test your patience, resilience, and, most importantly, your ego. After 7+ years of running Lash Line together, we’ve learned a thing or two (the hard way). Here are nine brutal but necessary lessons we picked up along the way that helped us achieve our healthy thriving business partnership!
1. You Are Not the Main Character Anymore
"It’s no longer just your vision—it’s OUR vision. That means compromise, even when your ego has you convinced your idea is way better." – Jessi Love
Sharing decision-making power is one of the hardest adjustments in a partnership. The days of making snap choices because you feel like it are over. Now, every decision is a team effort, and that means finding a middle ground even when you’re 100% sure your way is the best way.
2. Money Will Test the Both of You
"The moment cash flow gets tight (and it will), you’ll see your partner’s true spending habits. Are they a spender, a saver, or just plain reckless?"
Money is one of the biggest stressors in business. There will be moments when the business bank account is looking rough, and as owners, you might have to skip a payday to keep things afloat. If you and your partner are in very different financial positions, expect tension. The key? Have clear financial agreements from day one, including how you’ll navigate financial stress together. – Cara Kapler
3. No One Works Exactly Like You Do
"Just because you grind 24/7 doesn’t mean your partner will. If you’re expecting a clone of yourself, you’re setting yourself up for disappointment." – Jessi Love
Work ethic can make or break a partnership. If one person is hustling 12-hour days while the other is clocking out after four, resentment builds fast. Before going into business together, align your expectations on workload and commitment.
4. Agreements Solve Arguments—Put Everything in Writing
"Handshake deals = chaos. Contracts save friendships. Get everything in writing before emotions or money get involved." – Jessi Love
Think of your business agreement like a prenup. It should cover worst-case scenarios: What happens if one of you wants out? What if someone gets sick or injured? What if you just don’t vibe anymore? The agreement protects both of you before things get messy.
"In Canada, this is called a Unanimous Shareholders’ Agreement (USA)—a legal contract that dictates decision-making, dispute resolution, and ownership structure. Having this in place ensures that everything is crystal clear and legally binding before emotions or financial struggles come into play."
– Cara Kapler
5. Decision-Making Will Take Longer
"That quick pivot? It’s now a discussion. A debate. Maybe even a full-blown battle. Choose your battles wisely." – Jessi Love
Having a partner means every decision has to go through another person’s filter. It’s slower but can also lead to better, well-rounded choices.
For us, Jessi is a big-vision creative planner, while I'm a numbers-driven planner. When we disagree, we talk it out until we land on something that works for both of us (and the business). – Cara Kapler
6. The Dreaded Ego is the Silent Killer
"If one of you always needs to be right, the business loses. Put the brand first, or watch it crumble to pieces." – Jessi Love
Business is not about you. It’s about what’s best for the brand. If one partner constantly pushes their ideas while dismissing the other’s input, resentment builds, and the partnership will suffer. Ego-checks are mandatory if you want your business (and friendship) to thrive. – Cara Kapler
7. You Need to Like Them as a Human
If you wouldn't take a road trip with them, you shouldn't run a business with them. You'll spend way too much time together for fake energy. I couldn't imagine my life without Cara now." - Jessi
"Jessi and I started as business partners, not friends. Our dynamic initially was strictly professional, and then before we knew it... we were family. You'll go through a lot together in business and rely on each other for emotional, mental and business support. You spend more time together than you do with your families sometimes - so that bond will be a strong one! I'd pick Jessi over and over again, because we bring out the best in each other." - Cara
8. The Exit Plan Matters More Than the Entry Plan
"Getting in is fun. Getting out (if things go south) is where the real mess happens. Build an escape plan before you need one. Too bad for Cara she's stuck with me forever.)" - Jessi
"Any seasoned business pro will tell you that an EXIT STRATEGY is always a wise idea. You'll already know what to do if one of you decides to leave. It's called a Shotgun clause!
I have a feeling Jessi and I are going to be creating together, side by side in the senior home. We probably won't ever get around to using ours." - Cara
9. It’s Either the Best or Worst Decision of Your Life
"There’s no in-between. The right partner will elevate you. The wrong one will drain you. Choose wisely. You ask me, I made the best decision of my life." – Jessi Love
"Life throws curveballs—health struggles, family crises, financial ups and downs. The right partner will support you through it all. Someone's personal life has a major impact on their ability to be present, focused and driven. I had no idea some of the curveballs we would face together. But that was the biggest and best surprises of our partnership... the true strength and support in a strong partnership through it all... So I feel pretty lucky that Jessi let me into her business, and her heart." - Cara Kapler
A business partner can be your biggest asset or your biggest liability.
When we started this, we had no idea our business partnership would turn into a ride-or-die friendship. Lash Line is now celebrating 10 years, and through pandemics, soaring sales, and dead months, we’ve had each other’s backs.Here’s the real secret: When one of us succeeds, the business succeeds. Jessi and I feel that our business partnership is almost more important than the business itself. Treat it like it is. We plan little "bonding dates" together, even if it's just sitting on FaceTime catching up on life and work over a tea.
Want to watch/listen to more of our business/personal stories?!
We dive more in depth on business lessons and life lessons on our podcast, Twofold Uncensored - Anywhere you get your podcasts!
Listen to episode 1 here! - Turning Sh*t into Grit
Thinking of Starting a Business Partnership?
Do it wisely. Find someone who complements your skills, aligns with your work ethic, and, most importantly, someone you’d actually enjoy building a legacy with. Because at the end of the day, this journey is better when you’re in it with the right person.
Would you go into business with a partner? Or are you more of a solo entrepreneur? Let’s chat in the comments!
xo Cara + Jessi