Leadership and Management Lessons from Benny the Butcher — “Me & Doug”

Joe Stuntz
3 min readOct 20, 2020
Benny The Butcher

As someone who grew up in the 90s and played AAU basketball, most of the music I listened to was rap & hip-hop that certainly shaped what I listen to today. Early albums I owned were DMX “Its Dark and Hell is Hot” and Jay-Z “Reasonable Doubt Vol 2” in addition to records from the Lox and Ruff Ryderz (there were lots of others but those are what I remember). All this to say that while I listen to many types of music (metal in particular)today, hip hop that reminds me of that type of sound will always get played.

Recently one group in particular, Griselda, out of Buffalo has been leading that charge. In addition to the music, in the past couple of years I have seen them live a couple of times and love the energy and passion they bring. There are many music focused reviews of recent albums by Benny, Conway, and Westside and those are better than I could do, but what I enjoy it taking the lyrics from them and putting them into my world. So please enjoy the first in what will be an occasional series, Leadership and Management Lessons from Hip-Hop and especially Benny the Butcher and Conway the Machine. Also occasionally I will change a word or two in quotes as these albums are wonderfully explicit but I want to focus on the messaging.

“Me & Doug” is off Benny The Butcher’s 2016 album My First Brick and has been one of my favorite tracks for a while now.

“How you a boss and never took a loss in the game, its funny though cause sometimes your loss is your gain”

As someone who works at software company and who has been around technology for a while you hear “fail fast” or “fail often” too much in my opinion. These statements are missing the critical word of “learn” to me. Failure is only valuable if you learn something from it. If you fail fast doing the same things, that is just a waste of time and resources.

On the other hand, through social media, VC driven investing, and other avenues, there is a fake it until you make it approach leading all the way up to frauds like Theranos. Being able to learn and grow while you fail, pivot, modify, etc is critical as there is never a straight line in growth, product maturity, etc. This is where I feel Benny is going with this line. Whether in tech or in hip-hop, anyone who is really successful has failed but more importantly learned from that failure. Ignore the shiny and slick messaging and learn from failures to get better and win down the road.

“dont forget to stash something off for when it rains”

This is just good advice for any business or even individual. As the Covid pandemic demonstrates, there are risks that we cannot forecast and in general we have over optimized for lean when we should have a stash somewhere that may not be generating the top return, but will keep us going in tough times.

“real ones never worry about getting exposed”

This applies to businesses and individuals but I will focus on how I see it for leaders in particular. Treating people regardless of level in the organization with honesty and transparency in both good times and bad will build credibility and trust. If you treat people one way in good times but another in bad, or if you are one way in public but the opposite in private settings this will lead to problems. These problems may not happen right away and you need to adjust as a leader as the situations around you change, but you have to be viewed as honest (a real one) to keep the trust and faith of the team you need to lead to be successful.

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Joe Stuntz

Trying to figure things out working at the intersection of cybersecurity, business, and government