Who's on your personal board of directors?

Today I'm sharing my friend Raj Kapoor's story—of battling it out in the fitness startup world and ultimately needing to swallow his pride and merge with a competitor.

It's a testament to the indispensable value of trusted advisors—those who'll hit you with hard truths, kick your ego to the curb, and steer you through life's gnarliest decisions.

I hope this inspires you to cultivate your own circle of mentors and advisors. Trust me, whether you're a founder, exec, or just navigating a busy life, having this group in your corner is transformative.

With love,

Dave

At a Glance:

• From Reignition, the story of Raj Kapoor whose personal board helped him see past his ego and find the right path for his business. 

• The three types of boards we need: personal, inner and company.

• Why a group of trusted, loving, experienced advisors can support better decisions and a more meaningful life. 

• How to compose and work with your personal board of directors. 

Building Raj’s Personal Board

Here’s an abridged version of my friend Raj Kapoor’s story from Reignition. 

Raj is a successful entrepreneur. He was a co-founder of Snapfish, a venture capitalist with Mayfield, the chief strategy officer of Lyft, and now is a general partner for Climactic, a VC fund focused on climate startups.

In 2013, Raj founded FitMob, a marketplace for live fitness classes. Desperate to succeed on a larger scale, he pivoted to become an open network of group classes. He threw everything he had at building out the network that would make the company a huge success. But he faced massive headwinds. 

Specifically, ClassPass, another startup that had gotten to market first and built a more extensive network of studios. Despite Raj's experience and persuasive skills, FitMob struggled to keep up with ClassPass's growth. But he kept at it. Long after he should have seen the writing on the wall. 

Fortunately, Raj had a personal board of directors—peers and professional friends who knew him well. They told him, "You need to let go of your ego. You're selling yourself on a false narrative and are going to waste time, money, and energy on a fight you can’t win. There's a time to fight and a time to surrender."

In 2015, FitMob merged with ClassPass. Raj reflected, "I had to put my ego down and go to my competitor, a company we had viciously fought with for years, and give them the keys. It took everything I had, but it was the right call. If I didn't have my friends and spiritual advisors to help, I would have kept blindly fighting."

Why Build a Board

Effective leaders benefit from three types of boards: a Company Board, which oversees the business and our performance; an Inner Board, which is an internal conversation among the different “parts” of ourselves that drive decisions and our emotional state; and a Personal Board of Directors, a group of trusted advisors who help us grow personally and professionally. 

Today’s newsletter is about how a personal board of directors can be game-changing when it comes to big and hard decisions. This group of mentors is accountable to you, not investors or shareholders, so they adhere to your values and purpose, and your personal development is always top of mind.

Want to rebalance your life? Talk to the personal board. Sell your company? Board. Ditch it all to become a goat herder in Bhutan? Therapist first, then your board. Loneliness and solitary thinking can be brutal, even after your company becomes an 800-pound gorilla. Having people there for you who know you is the best way to ensure you’re growing, learning, and making good decisions.  

How to Build a Personal Board

This isn't just for founders or executives but anyone navigating a busy creative life. By formalizing it as a “board,” you give their role meaning and gravity and set expectations around structure and cadence, which I’ve learned makes a huge difference compared to just calling on people periodically. Here are four factors to consider when creating a Personal Board of Directors:

• Ensure diverse backgrounds and perspectives, including different industries, ages, genders, and ethnicities, to help you avoid built-in blind spots. This is why it’s different from mentorship—careful composition supports the best outcomes.

• Choose members disconnected from your business. This separation maintains objectivity and unbiased advice, free from politics or conflicts of interest.

• Select people who care deeply about your joy and success. But also look for bidirectional mentorship, where you can support and elevate each other in meaningful ways.

• Engage thoughtfully by articulating your ask, the feedback you’re seeking, and why you think they’re well-positioned to help. 

Your mileage may vary, but I find five to eight people to be the right amount. I connect with them individually two to four times per year or on an as-needed basis. There’s no compensation other than meals or supporting them when they need it. 

Ideally, as we age, we connect to a deep reservoir of intuition that navigates us through the cacophony of modern life. But it’s hard to stay in that place. A well-chosen personal board can provide crucial perspectives and align our decisions with our values, principles, and aspirations.

Who do you know that might benefit from creating their own Personal Board of Directors? Share this newsletter with them—especially if they're facing new challenges or feeling isolated in their leadership role.