Founder Coaching: 6 Insights from coaching Noah Kagan, CEO at AppSumo

Since I began recording for my new show “Out in the Open”, I’ve had some fabulous guests on. This one, however, is hands down the craziest show I’ve done to date! I’m taking a startup hero of mine, Noah Kagan into his underworld to meet some demons. Watch him take his shirt off, become the Tasmanian Devil and eventually settle into his inner Rhino roaming the savannah with his buddies.

Noah is the CEO of AppSumo.com and accompanied me as an unofficial mentor with his articles in my early startup journey and eventually became an investor in my company too.

Noah’s story from being at Mint.com, an early Facebook employee and many of his other adventures are deeply inspiring to me. What does so equally is his ability to go as deep as we’ve gone today. This episode has it all: Deep humanity, rage, anger, shame, disappointment, and eventually chilled relaxedness and deep inner power. Enjoy and let me know what you think.

There were a number of big takeaways in this episode for me that I wanted to highlight:

1. “Isn’t this all just human psychology?”

Towards the end of the episode where Noah and I have cycled through a number of different human emotions, he takes a step back and asks the above question: Wait, isn’t this all just basic human psychology? What I love about this insight is that yes, I agree with him 100%. As humans, we are much less complex than we sometimes make it out to be. Yet, that doesn’t mean it is easy to be human. Feeling fear, feeling shame, feeling joy, those are not super complex ideas. Yet, we come up with all kinds of hyper-complex models with our minds so we can avoid the basic experience of being human, which is at times deeply painful, disappointing and lonely. What Noah points to here for me is that life in its essence is always simple, yet not easy. Where are you avoiding the simple, but maybe painful truth and trading it for complex ideas and models?

2. “Is this enough? Am I enough?”

You’d imagine that someone like Noah doesn’t bump into this question. He runs an 8-figure business, has had success at some of the largest companies in tech, has a large online presence across Youtube, Instagram, Twitter and yet, he does find himself there. Is what I have to offer, without gimmicks, without better lighting for my podcast, is that good enough? The demon of “Is this good enough” in my own personal experience often stems from way back in our childhood, when we were maybe 0-10 years old. A parent that snapped at us, told us to shut up, or simply ignored us accidentally can leave this deep imprint in our psyches and bodies: Am I good enough?.

We come up with all sorts of strategies to reconcile that, yet the most powerful one is simple, yet the painful approach to go right into the feeling of “Am I good enough?”. To feel the self-doubt, the shame, the disappointment and to hold ourselves tenderly in that place. From there, we naturally come back to a more regulated version of ourselves that wants to go out and contribute powerfully to the world.

3. Spirit animals & Archetypes: Noah’s inner Tasmanian Devil, Squirrel & Rhino

As you can guess from the show, Noah is clearly no stranger to self-examination and self-exploration, otherwise, he wouldn’t have gotten to where he is in life today. One way that this shows up in our coaching session is by his access to a number of spirit animals or archetype. I believe that those are extremely helpful in the exploration and reconciliation of our psyche to become the most powerful versions of ourselves. Archetypes like the ones Noah is mentioning are powerful here for 2 reasons:

• First, it’s a way to speak to a part of yourself, without making that the whole essence of who you are (Rhino, Squirrell, Tasmanian Devil). This deidentification with your core self can free up tremendous energy and aliveness. Instead of saying “I’m bad and always angry”, understanding that “The Tasmanian Devil sometimes comes alive in me” is a way to acknowledge a part of who you are, understand how it serves you and also make that not everything there is to you.

• Second, when we come in contact with feelings, sensations and generally parts within ourselves, giving them names like the spirit animals that Noah has come up with, can make the processing of them more enjoyable. Instead of saying “accept your fear” or “feel your anger”, it’s a lot more fun to take up the posture of the Tasmanian Devil – the same result, but less taxing on the body in my experience.

4. “What’s your intention here?”

Noah coached me back a little bit in the session with this question towards the end. Why are you doing this Leo? What’s your expectation here? You can probably tell that this caught me off guard a bit and I took a moment to check in with myself. It was a good reminder to center myself around why I was doing what I was doing. Who is this show “Out in the open” for? What kinds of people am I hoping will see it? What do I hope they will learn from it?

I liked what I said to Noah in response. Which is to show any entrepreneur out there what it’s like to be in touch with our deep and dark places. To not be afraid to go there and to witness that even some of the most successful people out there are no different when it comes to their inner worlds.

5. The balanced human: Noah’s triangle

Early on in the session, I offered Noah what I like to call a “buffet” of all of the big topics that were on his mind. The core word he used was “congruency”. From there, he drew a triangle for himself and us around topics that most concerned him in this regard. They were:

• Location (I might offer a reframe of Community)
• Relationships
• Work, money (I might offer a reframe to fulfillment, purpose, contribution which Noah also shared)

We moved into the third topic for this session, but the others seem equally important in my opinion. Not just for Noah, but I think for any of us, that are looking to live a life that is rich and fulfilling in all aspects. It can be easy for me personally to ignore the first two, in favor of the third, because it’s very easy to see tangible results there. Few people congratulate me on a great relationship to my partners or for being a great friend. The rewards for that are solely experienced in those relationship or within myself. It can be harder to steer that way sometime I find. On the whole, I love the reminder to paint a bigger picture of what we’re wanting from life and how to navigate through it.

6. When are we done?

At the end, Noah put a powerful question in the room. He acknowledged having done therapy and a friend of his confronting him about doing more inner work. He wondered “Am I done with all of this or do I need to go back and do more?”. The answer for what he should do, isn’t mine to give.

But the question of “When are we done?” is one that I enjoy living into. I personally found that the inner unfolding and inner developing never ends. How we choose to go about it, with coaches, therapists, ayahuasca, meditation, walks in nature, journaling, you name it, is a different one. I’ve personally come to the conclusion that continuing to evolve and unfold with the support of a professional is both more powerful and scary than anything else I’ve done before in my life. Hence also my calling to be a coach to extraordinary people myself these days.

What does this prompt in you?

If you get a chance to see Noah in reflection, I’d love to hear what these prompts stir up inside of you and in your life. What are the biggest questions moving to you? Send me an email or message me on Twitter.

PS: I mistakenly didn’t record my own screen in the session above – oops. This way though, you get to see Noah’s full transformation all the way – pay attention in particular to his facial coloring, a great sign of when things shift in our nervous systems.