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My guest today is Steve Schlafman, a venture capitalist, leadership coach and partner at Primary VC. This episode is a wide-ranging, emotional journey through the nooks and crannies of investing, introspection, and sobriety.

Steve is a man of many passions. In the business world, he’s invested in breakthrough companies like Zipline, Brightwheel, Bark & Co., Managed by Q, Bowery Farming, Citizen, Care/Of, Boom Aerospace, TheSkimm and View The Space. Our exploration of investing was driven by five themes: leadership, market demand, customer focus, emotion, and human impact.

Outside of the office, Steve lives a sober life free of alcohol and other substances. He’s a passionate cyclist and rides more than 2,500 miles every year. This episode is particularly profound. Steve and I down down, deep into the depths of human emotion — from struggle, to pain, to addiction, to wonder and joy. I hope you enjoy this episode.

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3:30 – Steve explains his role and his program learning what’s called “transformational coaching” and how he became attracted to the idea of coaching.

6:30 – The value of coaching and common misconceptions of how a coaching can push and direct people. As Steve puts it, as a coach, “you shouldn’t be trying to fix, but instead, [trying] to understand. You’re not coaching the issue, you’re coaching the client.”

9:50 – The mindset of a good coach.

10:30 – David raises the questions of what makes a good coach versus a great coach.

11:04 “Self management” as a coaching mechanism.

13:45 – Steve reflects on coach Belichick and what he admires about him as a coach.

15:45 – Steve continues to dive into some of the abilities beyond coaching that Belichick exemplifies, namely the ability to asses and project players potential before even becoming their coach as well as his ruthlessness and situational awareness.

19:25 – The “human centric investment philosophy” Steve pursues. 

22:48 – Steve dissects genuine leadership and how it’s relevant to success as a coach and individual.  

26:45 – Where does that “drive” that successful people share in common come from? 

29:20 – Steve explains “Market Demand” via a story about opiate addiction and recovery. 

30:10 – David and Steve dig a deeper into the opioid crisis and how they have seen it affect those around them 

35:15 – Digital desensitization; how our modern relationships to tech and social media have been affecting our empathy and view of what’s going on in the world around us.

38:14 – What makes a brand a brand and the following and loyalty that having a good brand generates.

42:00  -Steve gives some examples of how great things happen organically, and not always when planned. 

47:50 – David reflects on the form of expression and communication GIFs introduced when communicating digitally.

52:40- Having children is on a downward trend. David and Steve discuss some of the factors surround this new trend. 

55:45 – Steve shares some of his observations from his recent trip to Sweden and the perceived quality of life by its residents.

01:02 – Steve shares some of the reasons he fell in love with cycling and what makes the sport so unique and non mundane to him. 

01:08- Steve talks sobriety and what it means to him.  He details the positive and transformative effects it has had on his life.  

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