In previous posts, I’ve addressed the two root causes of co-founder tension and how to self-coach yourself through a co-founder relationship on the rocks. I often get related questions from aspiring entrepreneurs about how to “date” potential co-founders or how to address future challenges proactively while still on the “honeymoon.”
What’s with all the relationship and marriage metaphors? There is even a successful entrepreneur matchmaking organization called Founder Dating.
As a startup coach, I know how deeply personal co-founder relationships can feel for my clients so the metaphor seems fitting in several ways. This got me curious about how I could apply marriage/relationship advice to coaching tips for co-founders. Here goes.
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The best marriage/relationship advice I ever received was in a hot tub outside of a yurt from an elementary school teacher. Seriously. But the slight sketchiness of the source aside—his advice was pure gold.
This guy (not my future husband) told me: “You only need two things for a successful long-term relationship: First, you need to have complementary values. Second, you need to have the ability to grow together. The first one you do your best to figure out upfront. But the second one you can only figure out by trying it out and seeing what happens.”
I took his advice back in 2002 and then took the risk to start dating my then-best-guy-friend. Over a decade later, we are still together and are now happily married. We had more-or-less similar values at the time, and we have worked hard over many years to grow together and continuously improve our ability to keep growing together. I often tell people that I actually dated several men in my 20s—my husband and I changed so much during that decade that it really feels like that.
I hope that each of you in your co-founder relationships will find the kind of long-term and hard-earned satisfaction I have found in my marriage. I hope you will be able to look back at a decade of working and growing together and feel tremendous pride in what you have built and given birth to—even if that is the birth of a new product or new company, as opposed to a new human.
To that end, I am sharing below five marriage- and dating-inspired tips for the co-founders out there who are still dating or on their honeymoon:
1. Make Your Contracts Explicit.
In my earlier post in this series about roles, I emphasize that anytime you decide to work with someone else on something you are entering into a contract. Even a contract that you don’t spell out explicitly is still a contract. So, why not take the time to have an explicit conversation about what is important to both of you about how you work together? I don’t want to get too prescriptive about what you should talk about and when you should talk about it because each co-founder relationship is unique and context matters. Similar to dating, it might be genuinely weird or premature for two 22-year-olds to talk about whether/when to have children on their first date, but that might be expected or more understandable for two 42-year-olds. At the same time, I understand the desire to have some sense of a framework, some range of ideas for what you MIGHT address in contracting conversations with your co-founder. Here are two resources to help you think through what you might discuss:
A Co-Founder Equity Calculator:
This equity calculator is designed by tech entrepreneurs for other tech startups so the other entrepreneurs out there who are reading this may need to do some translation to their specific business and financing models. Punching in answers and getting a numerical output is cool and satisfying in a certain way—but that is not why I refer this tool to founders who are preparing to discuss equity or have other contracting conversations. The real value of this tool is in the conversations it will spark between you and your co-founder(s). When you read down the list of roles, responsibilities and contributions—what thoughts or feelings emerge for you about which co-founders on your team are taking on which roles? Which roles and responsibilities do you personally value more? There are many reasonable disagreements and debates out there about the most fair or most effective way to split founders’ equity. Whether you choose to use a calculator, a weighted-value approach, or you follow Joe Spolsky’s philosophy to always split equity evenly among founders, what is most important is to use the equity discussion as a way to deepen your contract with each other and get some early practice at having important and, yes, emotionally-loaded conversations with your co-founder. Don’t shy away from a heated discussion now. The stakes will only get higher the longer you work together.
A Compatibility List from An Experienced Entrepreneur:
In this post, Hunter Walk (formerly of Google/YouTube, respected blogger and co-founder of Homebrew, a $35M seed stage venture fund) shares a list of 16 things an accomplished serial entrepreneur would use to “filter” potential co-founders. If you are a first-time entrepreneur who is considering co-founding something “with a friend”, please take a look at the list at the very end of his post. As you will see, many components of this list address areas where values or mindsets could be different but still complementary. Founders can behave differently but co-exist harmoniously—a point I address in greater detail in the first installment of this series.
Without a doubt, my favorite part of a wedding ceremony is when a couple decides to write and say their own vows. And this post’s cartoon aside—vows are some of the most poignant examples of contracting out there. Of course, your co-founder “vows” don’t need to be raw or personal—but they should be said out loud and shared with each other.
2. Deepen Your Commitment In Phases.
If your co-founder is not someone who you could honestly discuss the scenario: “What happens if this company fails or we decide to split up?” then you might think twice about whether or not this is the person with whom you want to start building a company. You could call this a buzz kill, but the chances are this will happen. If we accept the Harvard research that 2/3 of high potential startups are failing then the founder divorce rate is substantially higher than the marriage divorce rate these days. There is no way to protect yourself from a founder break-up, there are only ways to proceed cautiously and mitigate the risks along the way. First, you must accept the possibility early on that this partnership may not be forever. This is where the metaphor to marriage is the weakest—because while no one wants to head into a marriage planning for a separation, I encourage co-founders to enter into partnerships accepting that at some point they might need to part ways and that could be necessary, okay or even a really positive thing for the company. There are steps you can take to protect yourself in stages. Some couples who move in together wait to combine books, belongings or finances until they are engaged or married. Co-founders might set a timeline upfront on their initial work together. That gives them an explicit trial period and a protected time to evaluate, debrief and freely decide whether to keep moving forward together. Based on my belief that you should protect yourself and deepen commitment in stages, I also support others’ arguments for founders’ equity to follow a vesting schedule.
3. Share What’s Important and Then Validate What You Hear.
Share your values by communicating your desired behaviors and pet peeves. Sometimes I hear a founder confess to me, “Well, I thought we both shared a value about X, but I was wrong.” It’s very likely one of you did think you had a value about X, but sometimes it’s really difficult to know what your values are. If I were to ask you right now: “Tell me what your three most important values at work are.” It might be hard, but after a while you might come up with some possible-but-not-likely-definitive answers. However, if I were to ask you: “Tell me the top three things that people at work could do that would annoy you the most.” I bet that list would come out of your mouth much faster, and you’d be crystal clear on what to say. We don’t all have a deep track record in self-reflection and really getting in touch with our values. (And even if we do, our values can change and evolve over time and we might not be keeping up to date with ourselves as we might like.) But we all know what drives us nuts at work.
For this reason, I don’t usually recommend that early-stage co-founders simply “talk about their values” because 1) those conversations can scare off a founder who “just wants to get down to work” and 2) those conversations can lull you into a false sense of intimacy when, as you read in Part I of this series, your behaviors tend to speak volumes about what your underlying values truly are. A more effective question might be: “What is most important to each of us about how we work together?” Then, once you’ve shared these desired ways of working together and the don’t-even-think-about-doing-this-pet-peeves, it is important that you validate whatever you are saying to each other with actual observations of behaviors. Your co-founder might have claimed to hate unnecessarily long meetings, so what’s going on with his long-winded explanations during your weekly lunches? You talked about how being on time to meetings was really important to you—so why are you always late to interviews with prospective candidates? When you see discrepancies between alleged values and actual behaviors, it usually means there is another value driving behavior or that someone inaccurately communicated what their true values were. You co-founder might value confirming understanding more than an efficient lunch meeting. And you might value preparedness for an interview over showing up on time for an interview. By validating values with actual behavior you can start to learn what truly is most important to your co-founder (and yourself). This awareness can help you avoid the first root cause of co-founder tension—when values that seem complementary at a fundamental level end up causing tension over behaviors clashes at the surface.
And if you can’t anticipate what personality traits or habits/behaviors might cause tension down the road in your partnership—consider booking a meeting with a marriage counselor.
True story! My friend and fellow GSB alum Brian Helmick, co-founder of Algentis, actually met with a Catholic marriage counselor with his co-founder. I checked in with him recently and asked him about how that experience continues to impact them to this day. Brian told me: “The marriage counselor administered the same personality test he normally uses for couples about to marry. It was incredibly insightful and one report in particular, “Differences to Watch,” helped us see how the same traits that were complementary strengths could be sources of friction. The counseling impacted our working relationship in many positive ways. It definitely clearly signaled to each other mutual respect and created a powerful framework for discussion during the years to come.”
4. Create Values You Won’t Forget.
My fellow startup coach Dave Kashen writes and advises on the importance of a values-driven startup. I would recommend reading his post and it’s worth clicking through to his example of how the startup Sharethrough talks about their values. I see a lot of companies (both established and just starting out) promulgate a list of values with noble-sounding adjectives and ideals—but who knows what they actually mean? If it’s fairly easy for two co-founders to misinterpret each other’s values, what happens when you grow to a team of 5 or 30 or 100? I appreciate that Sharethrough takes the time to talk explicitly about what each of their values means and what each does and does not look like in practice.
I would challenge the early-stage co-founders out there to go one step further (or maybe it’s one step less) and articulate values in a way that you won’t forget. Use informal language, stories or inside jokes to describe your values so you will truly understand and remember them. The stories your co-founders tell and those your future employees will subsequently re-tell are powerful forces that pass on values and build your culture.
My husband and I have a set of explicit values for our family. At first, we tried the inspiring-sounding ideals (e.g., Joy, Stewardship) but it felt too stilted for our family startup and, more importantly, a few months later we couldn’t rattle off the list from memory. (If you can’t actually remember your values without looking at where they are written down, I would venture to say you have too many and they don’t truly reflect your core culture.) So, we shortened the list and re-named our family’s cultural ideals after inside jokes and compelling shared memories.
We have a value about enjoying life and laughing together, but we refer to it as “Dance Break” because of that gas-station-karoke-dancing-couple video that went viral earlier this year. We have a value about stewardship, about really respecting and caring for our home and our stuff, but we call it “Neatening” to pay homage to the early days of our co-habitation when I nervously asked my then-boyfriend to help me clean up our apartment by asking “Will you help me, um, neaten?” At the time, I thought “will you help me clean?” would come across as too cliché-naggy-live-in girlfriend. He thought my term “neaten” was really endearing, and has joked with me about it ever since. If an outsider were to look at our list of family values (Dance Break, Neatening, etc.) they would have NO CLUE what we were talking about, but what’s important is: 1) we do; and 2) outsiders have a clear experience of our values-in-action.
There is a lot of stress you have to endure when starting a company and you spend a lot of time working under severe resource constraints, but when it comes to values and culture the early days are when you have an unparalleled freedom and unfettered opportunity that bigger companies long for. So, don’t waste your time coming up with the perfect aspirational adjective to encapsulate your emerging values and culture—instead try a phrase from a story or inside joke or shared experience. You will never forget them and the stories will help your values stick.
5. Learn Together => Grow Together.
Now, to return to that hot tub outside the yurt, I learned that the only way to ascertain if I could “grow together” with the future co-founder of my family was to “try it out and see what happens.” Your co-founder might look great on paper or you might have a great gut feel, but the only way to tell if you will have the ability to grow together is to try it out. And when I say “try it out” I don’t mean some casual “let’s give it a shot,” I mean: view the whole relationship as one big experiment from which you can learn every day.
Just before the birth of my daughter, one of my mentors warned me how tempting it would be for my husband and me to judge ourselves at times of peak newborn-induced stress. Instead, she encouraged us to approach every stressful moment as a learning opportunity because that mindset would help us grow together as true co-parents. A few months after my daughter was born, I paid that same advice forward and wrote the following to a friend who was about to give birth herself:
“Whenever I miss a cue from my baby and try to feed her when she is sleepy or sleep her when she is hungry, I sometimes feel tempted to judge myself as a “bad mom” or I think, “crap! Mommy really screwed this one up!” But then I remember that Mom is actually just learning. It helps me to take a breath, try to glean something learn-able from a not-so-ideal situation, and then move on. It helps me to not get (too) frustrated with my kid and not get angry with myself or with my husband. This does not mean letting it go or pretending things aren’t hard sometimes or living in denial. It’s just acknowledging that something [a diaper change, a pediatrician visit, a long tear-filled car ride, taking a rectal temperature, etc.] didn’t go well and then asking, ok, so what can we do better next time?”
As you and your co-founder venture forth in your startup, I encourage you to view every day as an experiment. And then incorporate that active learning into every re-contracting conversation—big or small. What worked well and what didn’t work well? How can we do it better next time?
Just like a marriage, the co-founders that learn together are more likely to grow together. There are no guarantees of what the future holds and whether your founding team will remain the same as it is now. But by approaching the relationship with a commitment to learning and contracting, you set yourself up to have a more satisfying working relationship along the way.