Inside Out Leadership

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Welcome, Jason

Welcome Entrepreneurs, I'm so glad you're here. If you haven't already, check out last week's issue on how to work with technical and adaptive problems.

Big news this week. Inside-Out is continuing to evolve in wonderful and unexpected ways, and I've been excited to announce this next step for a couple weeks now.

Without further ado, I'd love to introduce you to one of my favorite people.

Longtime readers will remember that a couple years ago I decided to do my best to surrender to the Universe. I gave myself permission to let go of trying to get anywhere and simply do the best work I could each day, for the sake of the work itself.

Since then, my professional life has expanded in so many wonderful ways – ways I could have never predicted. Here’s a short list of what’s unfolded out of simply listening for what’s being asked of me each day:

  • My executive coaching practice, Inside-Out, has grown faster than I can keep up with;

  • I’ve helped On Deck conceive and build its CEO Group Coaching product for scale-up founders; and

  • I’m launching (what I believe to be) the world’s first Leadership Forum at the intersection of startup leadership development and racial equity systems work

…all while not really working that hard (Laura may disagree). It’s amazing what’s possible when you align yourself with the flow rather than trying like mad to push your own agenda. 

Today, the surrender experiment brings forth something wonderful yet again. 

I’m delighted to announce that Jason Pliml will be joining Inside-Out as an Executive Coach, a role in which he’ll partner with our team of five wonderful humans to help founders and VCs transform into authentic, realized human beings, and support them in creating companies that will change the world. 

Jason himself has been building companies for 20+ years, during which time he’s raised multiple rounds of financing, exited one of his companies, and bought another which he still owns today. He has also served many businesses as a formally trained coach, board member, and advisor to founders for more than eight years. All that aside, I’ve known Jason to be a wonderful human being, ever since we started an ill-fated Twitter app fifteen years ago in our “spare time” while we were both running other companies. My, how things have changed since then. 

By now you’ve heard my story, but I’ll leave it to Jason to share a bit of his: 

“Like most journeys, mine resembles anything but a straight line. I began my career as a software engineer before leaping off the employee wagon and starting multiple businesses. In those days, people often said, “I wish I could do what you do,” but what they didn’t know was that I wasn’t being honest with them or myself. I painstakingly focused on highlighting my successes, while filtering out my constant uncertainty, the periodic financial struggles, my raging imposter syndrome, and the missed memories that resulted from prioritizing my fear of failure above all else.

The more I checked the success boxes that were supposed to provide happiness and a sense of accomplishment, the more I noticed the underlying feelings that were actually running the show for me. Recognizing that satisfaction gap started me down the path of seeking answers.

For several years, I hokey pokey-d therapy with one foot in and one foot out. My inner struggles kept bubbling to the surface and I increasingly saw how they resulted in sabotaging my success and hurting people closest to me, yet I continued to focus on upgrading the curtains and wallpaper of a house with a cracked foundation. I was terrified of looking too deep out of fear of what I might discover. 

After years of half-hearted attempts to make change, years during which I began consulting for tech startups in addition to running my own businesses, I stumbled onto a course entitled Sacred Pilgrimage which weaved together psychoanalysis and Buddhism. It was the first time I willingly looked into my depths and uncovered the stark backing track belief to my existence: “I’m unlovable no matter what I do.” Acknowledging that unconscious mantra out loud didn’t magically neutralize its power, but it gave me a clear sense for why I functioned the way I did and why I required so much of the external validation that work conveniently provided.

Consulting for tech founders led me to coach training. Providing sound advice that clients embraced, but repeatedly struggled to implement left me repeating the same advice and watching the same inaction. It was a struggle I was intimately familiar with. I signed up for Co-Active Coach Training in 2015 with the goal of learning techniques to help consulting clients navigate around their internal roadblocks to implementing my advice. Little did I know the coach training program and subsequent 10-month leadership program would rebuild me to my core.

Prior to really embracing this journey, I lived as two people: thriving “work Jason” and struggling “home Jason.” At work, I felt accomplished, creative, in my element. At home, I played the role of supporting cast and backup parent. It brought me delight and peace of mind when I unified the Jasons into a single Me. This was never more apparent than when I reached a level of feeling as competent as a parent as I did as a business owner. 

These days the backing track no longer plays on an endless loop, and I’m able to sit in silence and feel gratitude, rather than a barrage of self-doubt and self-judgment. Instead of introducing myself as Jason the busy, hard working achiever, I confidently introduce myself as Jason, the compassionate, funny, intuitive human who values equity, human connection, and showing up authentically above all else.

My journey has defined my coaching philosophy and fueled my passion for coaching. I’ve been incredibly fortunate that people generously shared life lessons, observations, and wisdom with me, and I’m passionate about paying that forward. I recognize that you can’t become an effective, influential leader simply by learning techniques. To be a leader, you have to transform how you show up each day. As a coach, I invite clients to dive deep into the murky, uncertain places. Knowing that a client feels safe and fully seen through the uncertainty brings unmatched joy. I appreciate Ryan’s invitation to join his surrender experiment and I look forward to working with you and being part of your journey as a founder, a leader, and a fellow human.”


Things I read this week

One: How to know when to stop (AndyJohns)

Someone once asked Rockefeller how much he'd need before he had enough. He said "just a little more." If you're on a similar hedonic treadmill, this article by Andy Johns is an honest story of burnout, and a dense little resource for finding balance in your own life. 

LINK >>

Two: Eye movements could be missing link in memory (Neuroscience News)

A core practice of Neurolinguistic Programming is tracking a client's eye movements to see how (not what) they're thinking. Before learning the practice I thought it was voodoo, but science is now catching up to exactly why this works.

LINK >>

Three: Via Character Assessment

I was introduced to the VIA Character Assessment by a well known coach who described it as "a very useful tool for those diving deep in an attempt to understand who they are below all the conditioning." Now a few weeks removed from taking it, I'm finding myself referencing it often, and expect that VIA might join the Enneagram in one of the few tools I regularly use in my practice. 

LINK >>

Four: The Tail End (Wait But Why)

In one of my CEO groups we dove deep into the topic of parent mortality. At 37, I'm older than the author of this post, who created a graphic showing how much of his total time with his parents he had left. Click if you want some perspective. 

LINK >>

Five: What I learned about people who scale (Building Brex)

Assessing whether a person has the ability to scale along with a fast growing company is of primary concern to many CEOs I work with. But what makes a person able to scale? This post has an insightful perspective on the topic.

LINK >>


Want to dive deeper?

If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.

Here are a few of my favorites:


Executive Coaching for Entrepreneurs

There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.

I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency supporting founders to rapidly scale themselves as leaders, so they can thrive professionally and personally as their company changes the world. Leveraging 15-years as a founder/CEO, along with deep training in mindfulness, psychology, Neurolinguistic Programming, psychedelic integration and more, I have helped leaders from some of the fastest growing companies and VC funds in the world design a more conscious life and make key changes to improve their performance and satisfaction.

I coach leaders how I want to be coached:

  • Focused on the person, not the role.

  • Focused on results, without the fluff.

To learn more about working with me, click here.