You have the idea. You've made the plan. But before you quit your job and go all in, you've realized that you can't go it alone…
When your cards are on the table, and the future of your next venture hangs in the balance, who will you choose to walk the entrepreneurial path with you? Just like your corporate coworkers, co-founder relationships are notoriously high-stakes, but these power moves will help you decode unspoken cues of your potential partners and make strategic decisions without the gamble.
The Set Up: A Winning (and Losing) Pair
Like each round on the felt, work and entrepreneurship are an uncertain ride of wins and losses. Your best bet to stay balanced? A robust support system. That includes finding a co-founder or collaborator who shares not only your vision for your next venture, but also your level of commitment and risk tolerance.
And investors agree. “A team reduces business risk by diversifying skills, sharing responsibilities, and preventing burnout”, according to HBR. In general, startups with multiple cofounders also raise 30% more funds, are 3x more likely to succeed, and tend to last longer.
Venture Capitalist and Rent the Runway Co-founder Jennifer Fleiss, shares with Fortune Magazine how this experience bonds you like almost nothing else. "I feel very grateful that in these dramatic highs and lows of entrepreneurship, I had someone not just to deal with the low moments... but it's way more fun to deal with the high moments and at the end of the day that's what kind of gets you muscling through the next low." But choose wisely. You’re looking for someone who understands, “you're not in this alone because your co-founder implicitly cares just as much as you do, your necks are both on the line, you both got to make it work."
It’s about knowing your partner has your back, no matter how the cards fall.
The Deal: Taking the Leap
Here’s a hand no one wants to be dealt: “Up to 43% of startup founders ultimately buy out their co-founder because of interpersonal rifts and power struggles.” So how do you bet big on a passionate, values-aligned co-founder while navigating the risk of building something from nothing?
Think about it: taking the leap from benefits and a predictable paycheck to start something you believe in isn’t on the table for everyone. That’s particularly true if what you’re attempting has never been done before or if they have a family to support.
But everything changes when you can start building toward a shared pot before you even see the cards.
The Flop: Finding Equal Footing
Turns out, those who prioritize the interpersonal are significantly more likely — 70% more likely, to be precise — to find and maintain a do-or-die co-founder.
According to HBR research, lead founders typically prioritize specific skillsets and task-execution when seeking partners, whereas co-founders “are usually more motivated by curiosity or the possibility of finding a partner for work that they enjoy more than their current position.” It’s a bit like different players focusing on different parts of the same game – one on the numbers, the other on the table dynamics. Getting that alignment early is key.
One potential equalizer? Choosing someone to help you bring your business to life before you even have the idea in place.
“When people come up with a crazy idea together, they have equal stakes in it,” says LinkedIn Co-founder, Konstantin Guericke. “When your team works together to choose and nurture an idea, you will stick together through the inevitable dark times.”
Signs of a Power Struggle: Winning “With” Vs Winning “Over”
Vying for control and power can quickly derail the entire game. For co-founders who can focus on cultivating power with instead of power over, the odds of winning big are much better.
Power with is a collaborative force, supporting joint action and alignment — think of it as chips working together to build the pot. Conversely, power over stifles the relationship, like one player constantly trying to dominate the table.
One place this dynamic shows up a lot? Money. Some business partners assume that because they put in more chips, they call all the shots. But starting a business takes more resources than just cash. Be sure everyone at the table is recognized for their individual contributions and skills.
For women+ founders partnering with male-identifying co-founders, learning how to call and check unhealthy power dynamics is crucial. As is understanding how to fully step into your power, uplifting those around you when you hold a position of influence, no matter their gender.
Decide early on how you’ll set boundaries around power grabs and focus on really getting to know your co-founder, understanding their subtle tells before you merge your professional lives.
The Turn: Getting a Good Read
Much like poker, sometimes you need to ask the tough questions to get a read on the table.
Relationship expert Esther Perel, says the best way to vet a potential co-founder relationship is by getting challenging conversations out of the way up front. Inspired by The New York Times' '36 Questions That Lead to Love,' Perel invites would-be business partners and Sifted readers to explore these six essential questions:
- Tell me about a time when you changed your mind.
- What’s the best piece of advice you’ve ever received?
- Have you ever lost a friend?
- Have you ever blamed someone else for your mistake?
- Has there ever been a moment when you thought “am I giving up?” Did you, or didn’t you, and why?
- What’s a part of your identity that was given to you and what’s a part of your identity that you’ve chosen?
Once you’re set on moving forward, get the rules of the game down on paper. Perel says doing this before there’s any tension helps you, “think of the well being of all: stakeholders and the business as a whole."
It’s a way to strategize and document your joint moves before you’re holding a tricky hand.
The River: Proactive Moves to Make It Last
Cultivating a healthy co-founder or collaborator relationship requires proactive effort, much like strategic moves in poker. These aren't just one-off plays; they're habits that build a winning partnership.
- Never stop reading: Strong professional partnerships aren't accidental; they require consistent, proactive check-ins to nurture the bond, head off potential issues, and acknowledge shared victories, much like a poker player always keeps an eye on the table, even during quiet moments.
- Cultivate a relationship outside of work: Whether that’s attending a concert, museum tour, or standing up a regular poker night, the more you can focus on your connection beyond the office, the more likely you are to survive as a strategic partnership. You’ll be together for some of your biggest life events — births, deaths, marriages — a true partner in the game of life.
- Create a shared language: No one else truly experiences your venture in the same way you two will, giving you the opportunity to understand one another like no one else can. Your co-founder sees your poker face and knows what’s behind it because they’re playing the same game, right alongside you.
The Showdown: Playing the Long Game
Just like a skilled poker player understands their opponent, truly understanding your co-founder is your winning hand. By embracing open communication, proactively addressing potential friction, and recognizing the unique bond you share, you're not just building a business — you're building an enduring partnership capable of navigating any challenge the game of entrepreneurship throws your way. You're playing your cards right, and you're betting on yourselves.
Every co-founder journey is a unique game. What plays have defined yours?

FREE DOWNLOAD
Read Our Confidence Guide
By proceeding you consent to receive marketing communications (such as newsletters, blog posts, webinars, event invitations, and new product updates), and targeted advertising from Poker Power from time to time. You can unsubscribe from our marketing emails at any time by clicking on the "Unsubscribe" link at the bottom of our emails. For more information on how we process your personal information and what rights you have in this respect, please see our Privacy Policy and Terms of Service.


