Lessons for entrepreneurs from the Chairman of The Board

Lessons for entrepreneurs from the Chairman of The Board. (Frank Sinatra that is) — Over the holiday break I was spinning a lot of music from Frank and it occurred that two songs in particular speak to the journey that aspiring entrepreneurs. My favorite examples are ‘My Way’ and ‘That’s Life.

#1 — “My Way”: The Anthem of Autonomy and Authenticity

“And now, the end is near, and so I face the final curtain. My friend, I’ll say it clear, I’ll state my case, of which I’m certain.”

Frank’s start to “My Way” speaks to the entrepreneur’s need for clarity of vision. As Ben Horowitz, co-founder of Andreessen Horowitz, often emphasizes, successful entrepreneurs are those who “start with the end in mind and work backward.” They know where they want to go, and they lay out a strategic path to get there.

“I did what I had to do and saw it through without exemption.”

Sinatra’s acknowledgment of following through on his actions mirrors the advice given by many VCs: persistence is key. Marc Andreessen himself advises founders to be tenacious and relentless. Resilience in the face of adversity is often what separates successful ventures from those that falter.

#2 — “That’s Life”: The Rollercoaster of Entrepreneurial Ventures

“That’s life, that’s what all the people say. You’re riding high in April, shot down in May.”

In “That’s Life,” Sinatra captures the inevitable ups and downs of entrepreneurial endeavors. This echoes the words of Paul Graham, founder of Y Combinator, who reminds us that “startups are a rollercoaster.” One moment you might be on top of the world, and the next, you’re facing challenges that threaten your venture’s existence.

“I’ve been a puppet, a pauper, a pirate, a poet, a pawn, and a king.”

The entrepreneurial journey can have many roles, and flexibility is vital. Venture capitalists Craig Cummings and Kelly Perdew of Moonshots Capital advocate for an adaptable mindset, stating that “Great leaders are hard to come by. We believe the best ones are military-trained or trial-by-fire repeat entrepreneurs who have the ability to motivate others to action, inspire trust, and plan heuristically.” — In other words, they have done and tried it all. And they are not afraid to work all the jobs needed. Embracing the different phases of the journey is crucial to navigating the entrepreneurial landscape.

The Sinatra Blueprint — Both songs, with their rich narratives and emotional depth, offer a blueprint for the entrepreneurial journey. They remind us to lead with conviction (“My Way”), stay resilient in the face of challenges (“That’s Life”), and above all, to embrace the journey with all its twists and turns.

And please, don’t misinterpret Frank’s final lines in That’s Life:

“But if there’s nothing shaking, come this here July
I’m gonna roll myself up
In a big ball and die” — -

He just recommends that you fail fast and pivot to a new idea!

Here’s to doing it your way, in 2024 and beyond.