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If I told you that you were more likely to get split up with your  co-founder than get a divorce, would you believe me? A Harvard Business school professor studied 10,000 companies and found that 65% of businesses failed because of  co-founder conflicts. By the numbers, it can seem like having a co-founder is pretty risky in the first place. So what makes the risk worth it? The right partnership will make you more successful and more fulfilled (in our completely biased opinion) than a solo experience. Successes and struggles are always so much better to experience when you’re not alone. 

As in any other part of life, every relationship is different. You and your co-founder will undoubtedly have your own set of challenges and opportunities to grow stronger. That said, a lot of them will likely spring from the same core problem: bad communication. So how do you mitigate against that? 

My HeyMama co-founder Amri Kibbler and I see a direct correlation between the time we spend together outside the office and how it affects our energy exchange and alignment when we’re at work. When we connect one-on-one on a human level, that connection carries over when we’re back at our desks. And I’m not just talking about some old-fashion girl time (although everyone should make time for that too) — when Amri and I go offline together, it’s to throw ourselves into crucial, high-level, big-picture, magic-making time. It’s when we get the cold pressed version of brain juice that we normally can’t squeeze out amid the distractions of our regular workdays.

For the last 3 years, Amri and I have taken time for an annual co-founder “workcation” retreat. This yearly experience is so powerful for us. And because so much of our business is rooted in our relationships with our daughters — who were born just a week apart, so they’re as close as Amri and I are — we bring them along too. (It’s their favorite week out of the entire year, naturally.) 

For this year’s retreat, we chose the absolutely stunning Four Seasons in Wailea, Maui as the place to connect, and honestly I don’t think we have ever made a better choice for the site of this invaluable time together. The property had everything we could ask for — kid’s clubs and activities to keep the girls busy to delicious food and incredible service to make the stay even more effortless and elevated. The Four Seasons resort allowed us to really relax in ways that allowed us to truly focus on our time together as co-founders and best friends.

The investment we make each year in this retreat together is core to both our business and personal relationship, and I can’t recommend it for co-founder teams strongly enough. 

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Business Reasons to take a co-founder retreat:

  1. If there’s ever a time when you will inevitably come up with an idea that will change the course of your business that year, it’ll be this time of concentrated, distraction-free, co-founder mind meld. Creativity is constrained when we are in front of our desks all day. Magic needs space to come out.
  2. Knowing your co-founder on a personal level is such an important investment of time and energy. The strength of your connection as co-leaders will often be the thing that makes — or breaks — your company during challenging times. And just like in a marriage, any future fights (you will undoubtedly have them) will happen on top of a much stronger foundation of understanding if you two regular take time to stay connected and aligned.
  3. You’ll be happier and have better energy returning to work to lead your company. No one wants a burnt out leader. If you’re burning out, you’ll set that tone for your team. As always, self-care is a necessity, not a luxury.
  4. You can have hours-long brainstorms about strategy that you would never have time for in the office. And so what if you happen to be having these brainstorm sessions by a gorgeous pool… I mean, who is it hurting?  
  5. You can dive into your feelings with each other in a way that feels less corny than doing it back in the real world. When you and your co-founder tell each other how much you appreciate and admire each other and that you couldn’t imagine being on this insane journey with anyone else, while the sun is setting, and you’re both two margaritas deep,it is truly very special. Sometimes you have to set the scene for that kind of real-talk moment, especially when you’re both as busy as you are. 
  6. If you do decide to take your kids, get to know your co-founder’s kids better which ultimately allows you to get a window into their lives that you might not often see. Having more context into what your co-founder is experiencing in their life as a whole is immeasurably useful when it comes to being a comprehensively supporter partner to them. (Amri and I happen to be best friends, and I still always get new insights into her life on these retreats.) 
  7. You finally get a chance to have all those conversations you have been meaning to have. It’s a time for both of you to open up, be vulnerable, and get to the bottom of any lingering feelings or sentiments you’ve had, either about each other or the business.
  8. You can take beautiful content, which maybe you can repurpose for work, or maybe it’ll just be a nice visual cue for later when you’re back in your real life and need to be mentally transported back to that place of clarity. (Personal tip: We use Flytographer, and they nail it every year. (Yes, we have a discount code, of course: HEYMAMA50.)


Personal Reasons to take a co-founder retreat:

  1. You’ll create memories you won’t forget. For us we saw humpback whales within 30 feet of us and it was one of the greatest moments of our lives to see that with the girls.
  2. Our kids are really inspired and motivated by what we do. Our relationship has helped them have an intimate understanding of what it means to be an entrepreneur.
  3. You. Need. A. Break.
  4. You can take beautiful content which your grandma will want to frame, and then you can send pics to all of your family unprompted earning you major points.
  5. A co-founder retreat could be the difference between a connected and powerful relationship, and one that is purely business. We know our friendship is the backbone of why we built HeyMama, and hope anyone with a  co-founder remembers the most important point of all: cherish one another, and don’t forget to tell them they’re doing a great job.

A co-founder retreat could be the difference between a powerful, well-rounded relationship between two whole humans and one that is purely business. And when you’re a founder, and you work as long and hard as we do, it’s much nicer to do that next to someone you have a real human connection with.

3 pearls of wisdom


Knowing your co-founder on a personal level and building (and rebuilding) your connection will pay off over and over again as your business faces challenges.


When you get the other mastermind and visionary of your business to be distraction free alongside you for a few days, you get access to the pure, white-hot mental focus that can be nearly impossible to create space for back in the real world.


A co-founder retreat could be the difference between a powerful, well-rounded relationship between two whole humans and one that is purely business.

xx Katya Libin
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