Friends With Benefits
It’s one of the oldest adages (of wisdom?) shared with budding entrepreneurs. Everyone knows you don’t go into business with your friends. Total 101. Not only are the odds stacked against the success of your endeavor (the Bureau of Labor Statistics says 50 percent die a tragic death within their first five years), but your Facebook friend list may be a bit shorter by the time you’re done. As evidence, would-be business gurus point to a glorious path littered by a litany of failed friendships and, just as likely, failed businesses.
We missed that memo. Like the three musketeers, we (Adam, Wylie, and Chris) joined together to grow Collective Medical, the leading real-time clinical collaboration platform in the United States with thousands of hospitals, tens of thousands of medical providers, and tens of millions of patients. Our only excuse is that Adam’s mom, Patty, is a super intimidating (but really nice!) lady and when she told us to do it, we were too scared to say no.
For background, we grew up in Boise, Idaho as close friends, all went to BYU undergrad, roomed together, and have been pretty much inseparable for most of our lives. 2020 marks a decade of working on Collective together. So, at the invitation of Silicon Slopes and using Collective as the backdrop, we thought it might be interesting to reflect on a handful of lessons we’ve learned about how to succeed in business with your friends. We hope they are instructive in the event you decide to take the same plunge with your besties. Without airing all our dirty laundry, we’ve included real examples so you can hopefully avoid some of our mistakes. The punchline, at least for us, is that not only are we lucky enough to get to work together at a company about which we feel incredibly passionate and which is driving scale impact in improving patients’ health, but we get to do it with loads of truly extraordinary, talented teammates who are empowered to change the world for the better—in spite of us. And, bonus, we’re still friends.
Stay in your lane and presume trust. If a prophet is without honor in his own land, then the same can surely be said of friends in business. We intimately know one other’s foibles and follies and it would be easy to overly anchor on these. Here’s an example: Collective faced a true existential threat early in its growth. At the time, we only had a single customer segment and its governing body had just announced its intention to build its own, competing platform. Our customers would no longer need to use our solution. Chris did what Chris does and moved us straight to DEFCON 1. Our team banded together to immediately develop and begin executing a comprehensive strategy to deal with the situation. Along the way, Chris called Adam out for what he perceived to be a lack of urgency vis-à-vis this major threat that imperiled our future. And in doing so, he failed to presume trust. As it turned out, Adam also felt great urgency; he just displayed it differently and was working with equal diligence to address the threat. This was a key moment for us to realize that our different working styles weren’t a bug and cause to distrust one another, but rather, a feature to provide counterbalance, stability, and diversified thinking.
We’ve also learned to presume trust with respect to one another’s competencies. For example, Wylie is expert in information security, so while it’s okay for Chris to ask hard questions when big decisions arise, at the end of the day, Chris stays in his lane and defers to Wylie’s judgment, trusting the purity of Wylie’s intentions and knowing that he wouldn’t actually willingly impose a 56-character laptop password requirement unless he truly believed it was necessary (just kidding, Wylie only requires 55 characters).
Over time—and it has taken time—we’ve learned to trust: that each of us has the others’ best interests at heart without exception, that we’re fully committed to working our very hardest and that we respect one another’s unique abilities. At the end of the day, we’re trading on some three decades of friendship.
Don’t fight in front of the kids. This one seems obvious, but sometimes we get into it like cats and dogs (unsurprisingly, we have a lot of passion for Collective and the work we’re doing). We’re also unfailingly quick to resolve our differences and walk out the door as friends (even if sometimes still annoyed). The problem, as we’ve learned, is that not all of our teammates—especially those who are newer and may not know us as well—understand the depth of our friendship, have seen the trust and mutual respect we share, or see how quickly we make up. That can destroy morale and cause nervousness in the ranks. So, best to keep particularly tense conversations a bit more private.
What happens in friendship… should maybe stay in friendship. Two points here. First, we failed to appreciate just how different working together would be from playing together. In friendship, you play with your Tonka trucks in the sandbox, and if you want a break from your friend, you go home. But working together is like one constant sleepover, and sometimes you just need a recovery night back in your own room. Said differently, friendship is generally convenient, entertainment-based, and able to be throttled as needed. Building a company is often inconvenient, objective-based, and obligatory, requiring total commitment all. the. time. So, we’ve developed other friends we don’t share in common. While there’s a risk that can lead to FOMO and resentment, we’ve learned that mixing things up is not only a very good thing, but necessary. It’s okay to take a break from one another. It promotes fresh thinking, enables different experiences, and ultimately reminds us how much we value each other. At the same time, it’s essential to make time to do non-work things together: video games, chile con queso, and Letterkenny are some of our persistent unifiers. Friendships wane when not cultivated—ours has definitely not been all daisies and unicorns—and it’s taken us a while to learn that we have to keep investing, off the field, to prevent atrophy.
Second, things that are okay to do as friends don’t always translate well in the workplace. For example, Adam is very sarcastic—even cynical—and he’s hilarious. But when we recently started to explore a new body of work in an adjacent workspace that appeared unnecessarily cumbersome but also held out promise of a high impact, his frequent pop shots demoralized the team and negatively impacted morale. He, and we, learned that his sense of humor doesn’t scale fully across the organization and he has to keep it in check in the office.
Company > Role. One of the best things we ever did was unanimously, unequivocally, and non-negotiably commit / promise / agree to / uphold / recite daily / and whatever else this maxim. The company matters more than our roles in the company. Over the years, it has served us well. Inevitably, roles will (need to) change, certain skillsets will prove inadequate as needs increase, and blind spots will emerge. You must have the agility to change course. An unflinching commitment to the company over self allows otherwise hard conversations to be just a bit less so. But we’ve had plenty of hard discussions. Let us explain by example:
We each have our day-to-day roles, but they’re free to change over time. Wylie used to run a large IT team but now owns our Lambda effort (think: super cool, next-gen, skunkworks rapid prototyping and innovation) with a small team. Adam used to run a small development team, now runs all of engineering, IT and related functions, but has a coach to help him do so. Chris was once CEO with overly broad responsibility for nearly every major function but had blind spots and finite capacity so now has a strong support who has taken over functions like operations and finance. In each instance, these changes were preceded by difficult conversations. We didn’t always make up the same day. Some took months and feelings were raw. But because of the promise we made to one another, we’ve been able to make changes for the good of the team and company, ultimately without worry for ego, territorialism, or power struggle. And we’ve been able to do so because we care more about Collective’s success and its impact on our patients than we care about our individual roles in the same. This sounds academically easy but can be very difficult in the moment. So, commit to the principle early and never let go.
Establish Checks and Balances. We’ve learned, mostly through trial and error, that power dynamics matter. See Lesson 5 for an example of why. Imbalanced dynamics lead to mistrust, resentment, and failure. So, we have clear checks and balances. Chris is CEO, responsible for running the day-to-day business, making decisions when necessary, and ultimately serving as the single point of accountability to our stakeholders. But he reports to a board, which he chairs and on which Adam and Wylie sit with significant authority. This creates balance and enables us to function as true partners, irrespective of our assigned daily roles (which are free to shift over time as the company needs) and any implied hierarchy. This balance promotes trust and ensures we don’t get bogged down by consensus decision making (which, despite being effective for some businesses, is not a recipe for success at Collective) but also don’t have to worry about power struggles that otherwise arise from asymmetric information and authority.
Avoid cliques and empower others to blow yours up. A tight friendship makes it easy to drink your own Kool-Aid and bask in the ensuing echo chamber. Though we wish we would have learned it sooner, we eventually learned the importance of infusing new blood and thinking. Collective effort produces better outcomes, after all. So, we’ve learned not just to bring others into the business, but to bring strong others in who are truly empowered to challenge our thinking, disagree, outright fail, and most importantly, have true decision-making authority within their lanes of responsibility. Alas, this wasn’t always the case. Early on, we had an engineering lead who was a true rock star. He was highly competent, knew how to hire and train, was skilled at process management and had real passion for our mission. However, Adam and Wylie, as technical cofounders, struggled to let go of the reins and empower him to effectively run his team. It didn’t matter if he made a decision because no one respected his decision-making authority; everyone knew a decision only mattered if it was explicitly blessed by Adam or Wylie. This bred resentment, inefficiency, and ultimately led to this individual’s departure. This was a loss for Collective save that it taught us an incredibly powerful lesson. There is little worse than bringing in great talent and subsequently stifling their ability to contribute because we withhold autonomy to act and lead. We’ve learned that it’s easy to find people better than us at pretty much everything in the business. So, best to find them, empower them, make sure everyone else knows they’re empowered and accountable, and then get out of their way so they can do extraordinary things about which we could previously only dream. People who are micromanaged ultimately regress to do only the things required of, and managed for, them. But investments in autonomy pay dividends in productivity and outcome. We’ve found that people who are given rope sufficient to hang themselves rarely do so, and instead build bridges to success (seriously, we know that’s super cheesy, but go with us!).
There you have it. Six seemingly obvious but hard-won lessons. We hope they’re helpful to you and that, should you so desire, you might be as lucky as we are in getting to do something you love with the people you love just as much. Alfred Montapert said that “All lasting business is built on friendship.” Collective is the result of one such friendship.
by Chris Klomp, Adam Green, & Wylie van den Akker| Cofounders| Collective Medical