Welcome! After four years of successfully dodging covid, it finally found me. UGH! Thankfully I was only down for a couple days, but it definitely threw off my groove this week. Luckily David was already on deck to write this week’s feature piece. This week he shares thoughts and tips about how we can better encourage the people in our lives, including ourselves. So much of what he’s learned about this topic has come from the school of hard knocks, and I’ve so often been impressed with his willingness and ability to just TRY things and see how it goes. If I’m totally honest, I feel a little more like Piglet in this arena, cautious and unsure. Opposites attract? I hope you enjoy and benefit from reading this week’s newsletter. Thanks for spending a little of your time with us. —Mindy

How do you find the bravery and courage to be your best self?

If you’re like me, you had too many experiences as a child with adults trying to scare you straight. I’ve never met anyone who disagreed with the idea that living life well requires courage. We all know that courage is bravery in the face of fear. Yet, what I was modeled was anger and fear in the face of fear. 

Fifteen years ago, I was a young man just getting started. I had recently spearheaded the effort to create a new bank. My dad got swept up in the idea, too, and he joined me and helped me find potential investors from his network of high-net-worth individuals who had donated to the universities he’d raised money for over his career. I was excited. Then, he came to me one day and told me he had turned over our ownership to the attorney he had decided to work with. I felt betrayed and demoralized. 

That bank project was a beautiful experience working with my father until it wasn’t. Seeing the shadowy truth of a person can be gut-wrenching when you so fully love them. It would not be the first or last time he would show up that way in my life.

As we were phased out of the bank project, I looked for something else to work on. Unfortunately for me and Mindy, I had not learned this important lesson: No matter how I wish and try, I cannot fix any man who reminds me of my father. So, of course, I immediately fell in with a man with weak self-esteem, a constant need for external validation, and no boundaries.

I’ll cut to the chase. Two years later, I found myself across the table from him. He had surreptitiously stolen our production server, declared bankruptcy, and was telling me that if I wanted to get paid the $140,000 that he owed me, it was a “long fucking line.”

It is really challenging to show up courageously when fear and cowardice are the only things that the “mentors” in your life modeled to you. 

Defeated and feeling like a piece of shit, I reached out to people who I admired, but that had not been deeply in my life. One such person was an entrepreneur and venture capitalist with a mixed reputation in the tech community, so I won’t name him to avoid distracting you from the sweetness of what he told me.

He listened patiently as I told him how I was struggling, what had been so hard about these past two experiences, and how stupid I felt. He smiled, and then he looked me dead in the eyes and said:

“David, it may take a few more tries to figure it out, but I want you to know that your appetite for risk is one of the greatest gifts God ever gives anyone.”

To be seen without moralistic judgment, and to be appreciated by someone you admire for what you are feels so good.

I would go on to make many more mistakes over the years, but I would also go on to have many more successes than failures.

18 months ago, when I left the company that acquired the company I built, I spent several months Taking Inventory and reflecting on lessons taught over the previous six years (the total time from founding to sale to leaving). I have a list of 25 lessons taught from that experience, but two stood out to me as I considered what I would do next:

1. David, focus your maximizer ray on what someone is good at and excited to pursue. You see great potential in people, and they love how that feels, but they are unlikely to reach that potential without a strong base and momentum. If they do not build on a strong base and momentum, they will burn out and constantly feel like they are disappointing you. (this was a lesson my co-founder shared with me)

2. David, you are a gifted engineer and data scientist, and so you can ship incredible solutions through force of will. But if you want to be happy, work well, and have energy, make lots of tools!

After talking to several startups and to a score of people working in psychedelics, something stood out to me: The enterprise folks sounded like me 10 years ago, and the folks I was meeting in psychedelics were absolutely brilliant careerists who had decided their lives would be richer by focusing on wellbeing. As I seriously considered a move into AI-supported wellbeing, I envisioned a very narrow target on what would make an excellent co-founder:

• World-class operator with product management expertise

• Creative visionary obsessed with personal transformation and growth

• Incredibly stable personal life and deep self-knowledge 

• Passionate connection to and skill working with psychedelics over many years

Honestly, I made the target so specific because such an unlikely constellation of skills and passions meant I probably wouldn’t find anyone and a part of me wanted to take the easy route and go be a CTO for some enterprise SaaS startup. 

I met Tonia in January 2023. She was everything I envisioned! We quickly got to know each other, propelled by a mutual desire to build technology in service of our shared vision of helping people to feel better being alive.

It took almost nine months for her to find that stable base and momentum. For most of that time, she was certain that our partnership was mismatched and that she wasn’t bringing as much to the table. Now, she sees what I saw and feels her full capability mixed with a new entrepreneurial mindset. This mindset sees the unlikeliness of new things being successful and chooses to find hope in the mere fact that new things are successful at all. 

I have a profound relationship with the word encouragement now. Encouragement plays a pivotal role in imparting the courage needed to navigate life's complexities with bravery. It acts as a catalyst that ignites the inner strength required to face challenges, take risks, and step out of comfort zones. Here are ways I’m finding that encouragement fosters bravery:

1. Instilling Belief: Encouragement instills a belief in one's abilities and potential. Hearing or feeling that someone believes in you can transform self-doubt into confidence. This newfound belief empowers individuals to tackle challenges with courage, knowing they have support.

2. Reducing Fear of Failure: Fear of failure is a significant barrier to bravery. Encouragement helps mitigate this fear by shifting the focus from the possibility of failure to the growth that comes from trying. Understanding that failure is not a setback but a step forward encourages taking bold actions without the paralyzing fear of mistakes.

3. Providing a Safety Net: Knowing there is support provides a psychological safety net, making the stakes of taking risks feel lower. This perceived safety net encourages individuals to leap into the unknown, brave enough to explore uncharted territories because they know they're not alone.

4. Highlighting Past Successes: Encouragement often involves reminding individuals of their past successes and strengths. This reflection acts as evidence of their capability, providing a solid foundation upon which they can build new acts of bravery.

5. Inspiring Vision: Encouragement helps paint a vision of what's possible, often expanding the individual's perspective on what they can achieve. This vision acts as a beacon, guiding them through uncertainty with the courage to pursue their dreams, even when the path is unclear.

6. Emotional Support: The emotional support inherent in encouragement acts as a buffer against the stress and anxiety associated with challenges. Knowing they have emotional backing, individuals feel bolstered to face fears head-on, armed with resilience.

7. Modeling Bravery: When encouragement comes from someone who demonstrates bravery, it serves as a powerful model. Seeing others confront challenges with courage inspires similar bravery, showing that it's possible to act boldly despite fears.

Encouragement, therefore, is not just a buffer against the negative. It is a proactive force that equips individuals with the courage to engage with life proactively and bravely. It transforms the landscape of possibilities, making living well—a courageous endeavor in itself—seem achievable and worth the effort. Encouragement assures that while the journey may be fraught with uncertainty, the strength to endure and thrive is both within us and supported by those around us.

A few months ago, I introduced the idea of a collaboration that would be called ThisIsReal as potentially a way in which Mindy could find more of and a deeper connection to “our people.” We are early on this journey. Mindy has not done this before but has so many skills and talents that will help to make this successful. My hope is that in a few more months, she, too, will see in herself what I see and that, in the meantime, I will continue to be encouraging.

–David/Gonzo

NEAT!

Stuff we are digging. David⚡️ & Mindy✨

• I love a deep dive into a framework, looking into what it influenced and how one might practically incorporate it into one’s life (read Part III). ⚡️

• A neuroscientist shares why brains need other brains.

• I’ve been familiar with the book, Games People Play, for over 30 years but dismissed it as a pop psychology polemic of the how-to-win-friends variety. I was wrong. It’s great. ⚡️

• Our twins said this song sounds like it’s a fiesta in a haunted house in space. I’m here for it! ✨

SOMETHING TO TRY

While not everyone has an inner monologue, most people do. It can be fascinating to step back and just notice what it says. You may start to feel like, as Michael Singer describes it, you have an inner roommate who seldom shuts up. One day I was out running errands and driving to Costco when I decided to try something. Inspired by the Ram Dass meditation I Am Loving Awareness, I observed all the people around me and consciously directed love towards them. The way I did this was to notice something, anything, about them and think, “I love people who ________.” I love people who walk their dogs. I love people who have one big dog and one small dog. I love people who are a little overpowered by their strong, not quite leash-trained dogs. I love people who put stickers on their car’s rear windows. I love people who bring their whole family on a grocery errand. I love people who dress their twins in matching outfits. I love people who stop to ooh and ahh over toddler twins in matching outfits. I love people who ponderously scratch their beards while talking. I love people in hairnets working in food services. I love people who do their jobs in a relaxed and happy way—thanks for the eye contact and smile, cart return guy in the parking lot. I love people who obey the traffic laws. I love people who leave a big gap in front of them (though I do wonder why they leave such a big gap) when stopped at traffic lights. This is just a small sampling of the thoughts I had. By the end of my errands I was in a really wonderful mood and felt like I was seeing the best version of the world. It’s so easy to live in a kind of daze and only be shaken out of it by the unpleasantness of things. With a little mindful effort, we can instead be awake to the beauty and quirky delights that are all around us.

-Mindy

PARTING

WORDS

I learned that courage was not the absence of fear, but the triumph over it. The brave man is not he who does not feel afraid, but he who conquers that fear.

Nelson Mandela

PIC

That’s all for this week! If you’re into this, share this newsletter with all your friends. Connecting with new subscribers is magical! 🧚🏻‍♀️

DISCLAIMER: This newsletter is for educational and informational purposes only and is not intended as a substitute for professional medical advice.