If there is one truth I’ve internalized over my 52+ years walking this earth, it’s that life is chaotic. It doesn’t matter who you are, what you do or where you’re from, navigating life as a human in an ever-changing world is challenging. Period. I personally find the state of feeling overwhelmed to be both unpleasant and unproductive, and have spent the better part of my adult life trying to combat this feeling. Given my particular makeup, I have found being hyper-organized and (at times annoyingly) vigilant to be effective life hacks for imposing order on the fundamental disorder of life. Further, I find decision frameworks to be very helpful as I think about important issues across both personal and business domains. But if there is one super-power I’ve developed that has applicability in all aspects of life and which brings clarity to decision-making is what I refer to as “80/20.” While the notion of 80/20 is pretty hard to describe and has a lot of nuance, it can be thought of in shorthand as the intersection of “perfect is the enemy of good”, “get the big things right”, “optimization rather than maximization” and “a bias towards action.” From this you can infer that I find the concept of perfection to be wasteful, especially at the cost of speed and engagement. And you’d be right. But this only scratches the surface of that 80/20 really means.

Every human interaction is a negotiation, whether you like it or not, in the same way that either choosing to do something or not to do something still represents a decision. If I’m meeting with a company founder, my goal is to both give and receive, not only to get information and have them go away. If I’m having a heated discussion with my wife, I want her to hear my feelings, but I also want (and need) to hear hers as well. I do not view these interactions as win/lose, or what I call 99/1 encounters, but to get what I need and to have the other person leave fulfilled as well. Even in “traditional” negotiations, such as around a term sheet for a financing, raising money for a venture fund or another financial transaction, I’ve found that getting what I need without completely crushing the other party yields far better long-term outcomes than viewing the encounter as a 99/1 win/lose. Get what I need, don’t sweat the small stuff, optimize the relationship for the long run rather than maximize assuming a one-turn game, move on. Believe it or not, I even applied this rubric to my days on Wall Street structuring complex derivatives transactions for some of the most sophisticated corporations in the world, or bringing on a new trading team that was inexperienced and lacked the leverage and reputation of a team spinning out from a high-profile hedge fund. Even in these cases leaving the other party feeling respected and well-treated paid dividends over time, even though economics in the short-run weren’t maximized — but the relationship was optimized.

Some of the most amazing people I’ve had the luck to encounter combine the engineer’s 99/1 precision and problem-solving ability with vision and the pragmatic and balanced worldview of an 80/20 business leader. Building cool stuff doesn’t mean much without colliding with the market and getting feedback. 99/1s hate this because they don’t want to release anything until they perceive it to be perfect. Unfortunately it is extremely rare to build things in a vacuum, release them to the market and have them fly off the shelves. Even if a founder truly has a secret about customer preferences, nailing product out-of-the-box without any feedback is almost always a fool’s errand. In the same way that companies that go public have muscles that pre-IPO companies lack, products that haven’t been kicked around by users and run through the gauntlet are often ill-suited in their initial state. Adopting an 80/20 mindset doesn’t mean releasing something that’s crap just to release it, but it does mean being honest about the minimum viable product needed to get important feedback that can impact both product features and the product roadmap. 99/1s are afraid of scrutiny and/or devalue customer input. I find these people very, very challenging to work with.

All of this presumes a certain level of humanity as well as the belief that life is fundamentally filled with more repeat interactions than idiosyncratic collisions. By seeking to optimize across time rather than maximize for the moment, and by focusing on doing without fear rather than living inside one’s head and burdened by doubt, I believe one can lead a happier life, build a better business, and have more fulfilling relationships. While I could write more and perhaps write better, I’m following my 80/20 rule. Hitting Publish now.


partner @ebergcapital. owner @iasportsteam & @marlins. founding partner @iaventures. @thetradedeskinc @Wise. @UMich @Columbia_Biz. family man. wolverine. 〽️

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Roger Ehrenberg

partner @ebergcapital. owner @iasportsteam & @marlins. founding partner @iaventures. @thetradedeskinc @Wise. @UMich @Columbia_Biz. family man. wolverine. 〽️