The Power of Vulnerability

I’ve had some time off to reflect and feel compelled to share some thoughts on vulnerability and how embracing it has improved my life personally and professionally. People who know me in the past wouldn’t have guessed this : ) I got here through fits and starts later in life than most. Maybe this will help get you there faster than me : )

Everyone is struggling in their own way — from the 1% to the 99%. Vulnerability researcher Brene Brown (check out her TED talk) noted that we are the most in debt, medicated, obese, and stressed adult cohort in history — its not surprising we have a lot of issues bottled up inside of us.

What do we want out of life? We want to be liked, respected, and successful — at the core, we crave to be “significant.” I grew up thinking (like most type A over-achievers) that to reach this state, I need to ooze confidence, optimism, and charisma…that showing weakness and vulnerability was a mistake. I was wrong. The opposite is true.


Let’s start with friendships — we want to deeply connect with people. I’ve found it’s not possible without vulnerability.

Do you fondly remember the friends that talked only about their successes? The ones that were the life of the party but didn’t really take the time to talk with you? Do you really like hanging out with them? The moments I remember, the friends I cherish are the ones where we went deep, where we went through hardship together. Where we opened up on how we felt — without worry of consequence…and we actually felt better, more alive after it. When friends are honest and expose their wounds, they end up giving the most impactful advice and comfort to each other. I’m now demanding more of this from myself and from my friends.

Small talk is important when you first meet someone but if you can’t go deeper, it’s not fulfilling nor that helpful. I’m a networker — and I’ve thought the networking end goal is to make as many connections as possible — whether in real life or on social networks. It’s not…the number of connections doesn’t really help — especially in times of major change and upheaval. In those tough and grueling times, it’s just a few people in your inner circle, your tribe, that really make a difference. The ones you deeply trust. The ones to which you can expose your vulnerability. They are the ones who help you see clearly when you are obscured by fear or anxiety.

In our youth we should cast a wide net to meet and learn about as many people as possible. We will end up learning about ourselves through that process. But at some point we know ourselves, and its best to whittle down that network and go deeper.

I also feel my Silicon Valley friends are getting more authentic. Maybe it’s age vs a change in the makeup of the Valley. I’ll take it either way : ) We are less interested in a big networking party or conference and more interested in a raw conversation with a highly curated group over wine or even at a festival where we can shed our day jobs and live out our broader edges (e.g. Burning Man) without being judged. Conversations have moved from “how successful my startup/fund is” to the real challenges we have — struggles with family life, aging parents, raising money, keeping our health a priority, and remaining more zen as the pressure goes up. We are even seeing the rise of “user-generated conversations” at conferences that are authentic vs boring panels — and the topics every year get more intimate and interesting — failure, experimenting with psychedelic drugs, divorce, parenting screw ups…


It goes beyond friendship. In business, I’ve found that vulnerability is not a nice to have but “must have” for teams to succeed. I learned this the hard way early on in my career…

It was 1996 — the dawn of the first internet boom…I thought success was all about being smart and projecting confidence (even when i didn’t know what I was talking about)… I did this at HBS where i co-founded the Internet Club and became a self proclaimed Internet expert. Meetings followed with Kleiner Perkins, Sequoia, etc & I landed exciting job offers with internet heavyweights like Steve Ballmer, Bill Gross & others and eventually chose high flying startup @Home. I dove in, worked hard, and came up with “smart MBA” strategies. I was all about being intelligent, confident, getting the right answer and showing others what to do.

This approach failed miserably, even in the medium term. I was denied a coveted promotion. I felt broken and embarrassed. I was self-unaware why this happened…the feedback was painful once I heard it — ‘you may be right, you may be charismatic, but you aren’t liked. You’re trying to lead but they aren’t following.”

I wasn’t deeply connecting and building relationships with my colleagues. Leadership and management are about empathy — connecting, listening intently, and being vulnerable — relating by being human. The best answers lie in someone else’s head. Leaders can’t bring out the best of someone without connecting, without winning trust. Sure, it’s necessary to exude confidence and charisma at times (like when I’m selling or singing on a stage) — at times it may be necessary — but not at all sufficient.

Also, most decisions have tremendous uncertainty. The data rarely clearly points to one direction vs another. When that happens, the team turns to the leader. If they don’t connect, if they don’t trust, they won’t stick with the leader.

Brene Brown found that we tend to be particularly sensitive to signs of trustworthiness in our leaders and this trust is correlated to team performance. You can even see this in the brain. Employees who recall a boss who resonated with them show enhanced activation in parts of the brain related to positive emotion and social connection. The reverse is true when they think of a boss who did not resonate.

Jim Laudan and Katharine Lind wrote, “Being vulnerable in the workspace doesn’t mean you walk around with a box of tissues and share your deepest, most personal secrets with everyone. It simply means you are ready to let your guard down, put aside any pretenses, and be your real self. A vulnerable leader is one who checks his or her ego at the door, is comfortable with not having all the answers, and is ready to wholeheartedly embrace the perspectives, opinions, and thoughts of his or her people.”

I learned and applied these lessons to my first startup Snapfish and then later had to painfully re-learn it again as a VC. My most recent startup, Fitmob, really benefited from this power of vulnerability…

Some context — after a good seven year run as a VC at Mayfield, I was itching to get back into the operating world. I felt I would be a better leader and it would be easier the second time with all my scars. I started Fitmob with the goal of becoming the largest marketplace for fitness.

I was personally passionate about the fitness space — and I thought I could nail it. In many ways it was easier than the first time — I could raise money with less effort, hire faster, spend far less to get results, and iterate and pivot with less emotional angst. Also, it was easier to be authentic and vulnerable in my 40s and it resulted in a very transparent and tight culture. However, one thing remained super challenging where experience doesn’t help (and sometimes hurts) — product market fit. We had to iterate three times before we found a model that worked — and the final model wasn’t original — it looked a lot like our competitor ClassPass.

We pivoted into a studio/gym class capacity utilization model (away from our initial model creating neighborhood pop-up gyms using trainers) which, as ClassPass proved earlier, consumers loved. We quickly raised more money and launched 7 cities. ClassPass was ahead of us with 20 cities and over $50M raised. After some brutal competitive fights, we realized that maybe it was better to join forces. It wasn’t like an Uber/Lyft dynamic (which I saw first hand as the first VC investor in Lyft) where two could survive and thrive.

Luckily, by this time, I was comfortable expressing this vulnerability to my board and key investors. I had been careful to pick people in my trust circle. I was self-aware that despite my past success and ability to raise more money, it’s better to join forces with competition vs fight. When I exposed my concerns with trusted advisors like David Kirchhoff, Tim Chang and James Currier, they validated my thinking. We decided to give it a shot.

Merging with a competitor — especially two private companies — is really really hard and most of the time fails. Particularly when they are fighting each other so publicly and fiercely. I knew from experience that ego and grandstanding can get in the way of the right business move. I also decided that I didn’t have to be CEO — i could help with out having to run it. That took some deep soul searching.

I felt the initial approach to the CEO of Classpass would be critical to setting the tone. I got some of the best advice from my friend and legal counsel, Ted Wang as well as the Exec Chairman of ClassPass — Fritz Lanman. They recommended that instead of posturing in the first meeting, I should be completely honest and vulnerable. Just admit upfront that I copied their model. The critical thing was making the human connection between the two CEO’s…

When I sat down with the ClassPass CEO, Payal, the first thing I said was “We copied you — because you came up with a better model than we did.” It melted the tension and we had a great three hour dinner. When we got to the tough issue of running it, surviving brands, etc — I suggested she run it and keep their brand as they did a better job branding. This openness not only got us to the table but resulted in a super fast negotiation on price. Because we were transparent about how we were both going to determine value, there was no price negotiation. They submitted an offer and it was exactly at the discomfort point for both of us (which defines a well priced deal). It was one the fastest negotiations and I hope it will go down as a successful private combination of fierce competitors.

Another hopeful example of fierce competitors coming together

It’s Not Easy

Being vulnerable in life and business is not easy and requires a lot of trust. We are afraid of rejection and of not being respected. There are some people out there looking to pull us down — they feel better when they see us fail — the haters.

For these reasons its important to build a circle of trust — to have a tribe — that we can depend on for advice, that we can do business with, and that blossom into meaningful friendships.

I am by no means an expert nor a master — however, I’m inching forward every day. I’m aware — and knowing is half the battle.

As Howard Schultz of Starbucks said, “The hardest thing about being a leader is demonstrating or showing vulnerability… [but] when the leader demonstrates vulnerability…the team wins.”

Hopefully you will find your tribe, open up, and see what the world delivers to you.

Note: here’s a nice soundtrack for this article -

Thanks to James Currier, Tom Patterson, and Lydia Alexander for editing drafts!