This isn’t your average holiday spread, and it’s not your average holiday message-from-founder: hold on to your sleigh bells, cause things are about to get… CHEESY! 🧀❤️
I started my first company with my partner of now almost 20 years, Christy. When people we interacted with in the course of business discovered that she and I were also together in that way, usually they’d get somewhat uncomfortable at first. The most common reaction was one of feigned admiration: “Oh, wow, I could never do that – we’d kill each other!”
Spoiler: Christy and I didn’t kill each other. In fact, not only did we live to tell about it, we’ve already embarked on several more ventures together in varying capacities (in Outlaw she’s not a co-founder, but rather an advisor and investor).
Fast-forwarding nearly a decade, my current co-founder at Outlaw, Dan, is the long-term partner – yes, in that way – of Christy’s sister, Lindsay. If both couples were legally married, Dan and I would currently be brother-in-laws. But we’re not, so now you know how we came up with our edgy legal tech startup name. The point is, here I go again, mixing business with personal.
It doesn’t stop there either. Our Director of Customer Success, Julie, is my sister. Our VP of Engineering, Keven, is a close friend I’ve worked with on and off for about 15 years. Our Technical Advisor, Jorge, was a college roommate and co-founder in my first startup.
Christy, Dan, Julie, Keven, Jorge – these are deep, lifelong relationships. These are people I love. But these are people whom, according to traditional wisdom, I should keep at arm’s length when it comes to business, because “work” and “personal” should be kept separate.
Google published a study about this in 2016, and while it’s largely confounded by confirmation bias, it does introduce some apt terminology: segmentors are the people who looked at me and Christy like we were crazy to found a startup together. And integrators are people like us, who blur or outright erase the lines between work and personal.
This is just one aspect of the broader “future-of-work” field of study, and needless to say, there are adamantly held, conflicting viewpoints pretty much everywhere you turn in that field. While I do have some hopeful predictions of my own on the subject, my purpose here is not to enter these debates, nor is it to attempt to convince anyone who identifies as a segmentor that their way is worse or inferior.
In fact, my purpose is quite the opposite. Most of the working world is already designed for segmentors (hence the confirmation bias) – and that works well for millions of people. My purpose is simply to share that there are also some wonderful benefits of being an integrator – both personal and organizational.
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Firstly, running a startup is stressful as fuck. Hopefully that’s not news to anyone, and I’m not complaining; I know what I signed up for. But being on this rollercoaster with people I care about deeply and trust unequivocally is what makes the stress manageable. The highs are higher and longer-lasting, and the inevitable lows are not as low, with faster recovery. Seriously, it’s therapeutic.
And it spreads. Every weekday at 5PM, we take 15 minutes on Zoom (it would be IRL but, ya know, covid) to go around and give each team member an opportunity to share a personal “win” from their day. It’s been a delightful exercise in optimism and gratitude, which shouldn’t be surprising, given that the teammate who came up with this format is our very own Olympian! But I’ve also noticed another surprise benefit. It’s easy to celebrate obvious accomplishments – a new customer signed, or a new feature launched – but the reality is that not everyone can muster a genuine win every single day; sometimes someone is really struggling with something, or simply having a shitty day.
That’s not a rare occurrence (especially when, ya know, covid); these moments arise a couple of times a week, sometimes daily. When people share their vulnerabilities and ask for help and guidance, the outpouring of genuine support, collaboration, and – let’s call it what it is – love, from across the entire team, is downright inspiring and heartwarming.
That brings me to the biggest and most quantifiable organizational benefit of this mode of operation. The same group at Google who published the study linked above has also been studying team effectiveness for years. To summarize a vastly complex and infinitely nuanced topic down to two words, it all hinges on psychological safety.
That’s a mouthful, but it encompasses a lot of the underlying principles and existential factors I’ve been talking about in this post: openness, vulnerability, trust, humility, etc. The long and short of it is that when people on a team feel comfortable acknowledging fear and uncertainty and admitting mistakes, the whole team can learn and improve faster. And when that team’s mission is developing and selling software, that difference isn’t marginal or incremental; it’s exponential.
When you’re working with people you love, everything is easier. Brainstorms and creative collaboration are more fun and more fruitful, because you’re free to focus on the ideas rather than the egos of the people presenting them. Sprints toward aggressive deadlines are exciting instead of soul-crushing, because they include a magical added element of shared experience. Even hard conversations and conflict resolution are smoother and less gut-wrenching because, ironically, they’re not personal; they’re about the results of the work.
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Outlaw is still an early-stage startup, so I meet with investors regularly. When they see our leading-edge platform and delighted customers vis-à-vis our time in-market and amount of capital raised to date, they’re consistently amazed. They look at me with the same cockeyed expression that Christy and I used to encounter, trying to discover the x-factor that makes it even possible. I can answer them using pseudo-scientific terms like “psychological safety” on the team, or I can invoke safe-for-work business jargon like “deep domain experience” and “proven working relationships”. All of those things are true. But the more direct and authentic way to put it is this:
There’s a lot of love at Outlaw, and love is a competitive advantage.
I won’t attempt to recap 2020’s challenges here – we’ve all been through it. I’ll simply say, from myself, Dan, everyone mentioned in this post and the whole Outlaw team: happy holidays, happy new year, and here’s to next year being better, healthier, brighter, and filled with love.
