Hey there! I’m Robert. Welcome to a free edition of my newsletter. Every week, I share my story of bootstrapping my AI startup focused on hyper-personalization and Alignment. I’m documenting my journey to become my best self—and helping humanity do the same to survive and thrive in the age of AI.These newsletters include my reflections on the journey, and topics such as entrepreneurship, startups, growth, leadership, communication, product, and more. Subscribe today to become your better self.
About 5 months ago, I started running.
I fucking hated it.
I’d gas out, my lungs burned, and my brain told me to quit. There was no “runner’s high” about it.
It was awful.
But, I wanted to make myself love it.
And last weekend, I just completed my first ultramarathon—31 miles and >5k feet of elevation gain.
Unsupported.
There was no official race, there were no accolades or celebrations.
There was no crew, no spectators.
Nobody cheering me on.
I did it alone.
And now I’m going for 100 miles unsupported next year.
Why?
Two Reasons
#1 Longevity:
I want to live longer—not just in years, but in quality.
I want this, because I want to be the best dad ever. I want to be able to be active with my future kids until I’m 100.
The outcome I desire long term, is a result of the habits I exercise today.
My future kids—this one’s for you. Your dad loves you. (‘:
Running is one of the most efficient ways to build cardiovascular health. And it’s super low friction, you just put on shoes and you go outside.
In my busy schedule, I need low friction and high synergy.
I pair running with listening to the latest podcasts or news or audiobooks in the entrepreneurial arena I’m competing in.
I even take business calls when I’m doing zone 2 running.
Hell, lately I’ve even been recording running motivational videos as content for my ICP (Ideal Customer Profile) for Clarity.
I can get ~10-15 shorts done in a 1 hour run. Hyper-optimal.
#2 Entrepreneurship:
I’ve learned building a company is a game of endurance.
Last human standing wins.
Running feels like training for that mental marathon.
Because if you’re a founder, you are running in that mental marathon every goddamn day.
It’s HARD.
You go through this Emotional Cycle of Change almost daily, where your competence is challenged constantly.
Tell me if this sounds familiar to you as a founder and entrepreneur.
You have an idea or new direction.
Then…
1. Uninformed Optimism
“We totally got this—we’re gonna change the world!”
You’re fired up, imagining all the benefits and barely noticing the challenges. It’s brainstorming, big dreams, and excitement. Everything feels possible.
2. Informed Pessimism
“WTF I didn’t know it’d be this hard.”
Reality sets in. The costs of change feel heavy, and the benefits seem distant. Doubt creeps in, and you start questioning if it’s all worth it.
3. Valley of Despair
“Maybe a day job isn’t so bad.”
This is the make or break point. Progress feels nonexistent, and quitting feels easier than pushing through. But giving up now means starting over later.
4. Informed Optimism
“Finally, we’re seeing results.”
Momentum picks up. The benefits become visible, and the challenges feel manageable. You start believing again and push forward with renewed energy.
5. Success and Fulfillment
“Okay that wasn’t so bad, we made it through!”
The hard work pays off. The benefits are real, and the struggles were worth it. What once felt impossible is now routine. You’re ready for what’s next.
Rinse and repeat.
Sound familiar?
The Highest Leverage Skill
Both longevity and entrepreneurship are long games.
And long games demand one thing above all: the ability to keep putting one foot in front of the other—especially when it SUCKS.
Basically, I wanted to prove to myself I can keep going even if I don’t want to.
I wanted to prove to myself that I can force myself to enjoy anything I don’t want to do.
Much of life, I’ve learned, is about doing things you don’t want to do even if you know they’re good for you.
I believe that is one of the highest leverage skills in life: the skill of enjoying doing things you do not naturally want to do.
It started with eating broccoli as a kid.
Then exercising as a teenager.
Then therapy, journaling, and more as an adult.
And now that I want to be a successful entrepreneur, it’s all the things I don’t naturally find fun as CEO that I NEED to find fun to succeed:
Building pipeline
Making content and marketing
Operations
Accounting and finance
Admin meetings
etc.
I naturally love everything around product. That type of work gives me the most joy.
But… The product is just one side of the business.
That was the biggest mistake I made in my first tech startup as CEO.
I focused too much on what I loved.
Winning doesn’t care about what you love. It cares about what you do.
So my thinking: learn to love everything that it takes to win.
And the product is just one small factor in the true outcome I want to drive:
Empower everybody on the planet to become their best selves.
That purpose takes much more than the skill of building a great product.
So to get there, I’ve learned I must enjoy the journey and everything that comes with it.
Every great thinker has said some version of the same thing:
“The journey is the reward.” — Steve Jobs
“Success is peace of mind, which is a direct result of self-satisfaction in knowing you did your best.” — John Wooden
I have found that the paradox of true mastery is that the goal only appears when you stop chasing it.
When you love the act of showing up—
when the effort itself becomes the win,
the outcome becomes inevitable.
And the outcome I want:
To be my best self.
Entrepreneurship is an Ultramarathon
I kind of think of founding a startup as an ultramarathon for the soul.
Every great entrepreneur I’ve studied says the same: it’s the game of last human standing.
You will fall.
You will fail.
You will question yourself more times than you can count.
The game isn’t about talent… it’s about recovery speed, and the will to keep going.
Can you fall and get back up, again and again?
Can you face uncertainty without needing motivation?
Can you keep going when nobody claps?
That’s what running trains: the capacity to move forward in pain and suffering.
Learning to love running, has taught me to love hard effort in the face of pain and suffering.
To love persistence.
Rewire Your Brain
Now let’s talk about meditation.
It’s one of the most powerful tools I’ve encountered in my journey to become my best self.
Meditation is one key to how I train my mind to love doing things I do not naturally enjoy.
It strengthens the prefrontal cortex (self-control, planning, focus) and shrinks the amygdala (fear, stress, reactivity).
My interpretation from this is that you can use meditation to literally train your brain to get better at doing things you don’t want to do—and to enjoy them.
And I definitely find that true in practice.
This past year I determined to be consistent, to continuously exercise the skill of doing things I don’t want to do and enjoying it anyway.
To continuously build up the capacity of rewiring my brain.
Now I’m at 315 days of daily meditation for at least 30 minutes.
Side note: I’m going to post some YouTube videos soon of my meditations, where you can follow along. I’ll share those when they’re out.
What has the result been?
Well—these days, I find myself enjoying being in the Valley of Despair of any entrepreneurial challenge I face.
I attribute much of my ability to learn to love doing things in life I don’t naturally enjoy but are good for me, to meditation.
That’s how I went from hating running… to craving it.
I’ve found that the magic in meditation and running is that they’re feedback loops for growth.
This is how I think of it:
Running trains the body to endure discomfort and pain.
Meditation trains the mind to sit with discomfort and silence.
Running teaches persistence in motion.
Meditation teaches persistence in stillness.
Together, I have found my ultimate mental-physical practice for building freedom—the freedom to act independent of mood, motivation, or momentary pleasure.
Every time I sit for 30 minutes and focus on my breath, I’m teaching my brain:
“You’re not in charge of me. I am.”
Every time I run 10 more miles after my legs scream to stop, I’m teaching my brain:
“You don’t decide when we stop. I do.”
Are You Really Free?
Here’s a question that will trigger defensiveness in many:
If you do not have the will to choose healthy food and hitting the gym over eating junk food on the couch doomscrolling…
Are you really high agency? Do you really have freedom?
If you can’t even control what you put in your mouth or where your time goes, how free are you really?
In my mind, not at all.
I used to let my impulses and base desires drive me when I was younger. Probably like 80% of the time.
Nowadays, I would guess it’s more like 2% of the time.
I’m not perfect, but I always strive to be high agency.
Why?
Because I believe you don’t really have true freedom if you let your impulses, base desires, and temptations drive you.
If those drive you, you are a slave to them. You are not free.
And I don’t know about you, but as much as I can I want to exercise my own free will.
I believe everybody can be better than their base desires.
As a kid, I used to mistake freedom as the ability to do whatever we want.
I craved going and getting McDonalds, because all the other kids in school got to have it.
I craved that new toy, because the other kids in school got to have it.
As an adult I see it around me:
people buying fancy cars,
fancy homes,
fancy clothes,
to fit in.
People thinking they need to check boxes on partnership and kids by a certain date, otherwise they’re broken and “not good enough”.
People thinking that the solution to all their problems is just that next promotion on the hedonic treadmill of Corporate America.
People constantly comparing themselves to others in every respect, as if comparison is ever really fair.
Our world is noisy.
That causes you to lose sight of the signal and clarity inside yourself.
Do the fancy things really make you happy?
Do the check boxes handed to you by society really mean a full life?
Do the promotions give you purpose—or just a new title and less time?
Does the constant comparison bring you joy?
I have found in my journey, that the answer is no.
I almost fell into that trap. I dipped my toes in, and decided it wasn’t for me.
I’m glad I went to therapy 9 years ago and built the skill to recognize which beliefs were mine, and which ones society gave to me.
I hold close the ones that are mine—truly mine.
And I discard the rest.
In that, I find true freedom and agency.
My fundamental belief is that real freedom and agency comes from the ability to do what’s good for us—even when we don’t want to.
Not from giving into your base desires, impulses, or temptations.
That’s why I believe most people stay stuck and are uncertain in who they are.
They mistake ease for happiness.
They confuse friction as “not for me”.
They avoid the real work of parsing signal from noise, to find their own voice and beliefs.
They avoid journaling, therapy, mindful practices, and healthy habits that fuel true self-growth.
But from my experience, the friction is where your better self begins.
Every repetition of something difficult is a step towards the person you want to become.
Because you are what you do, not who you say you are.
Every meditation, every run, every early wake-up, every therapy session, is a declaration:
“I am the best dad ever to my future kids.”
Every single time I do things I don’t want to do for the business, and enjoy it anyway, is another declaration:
“I am the entrepreneur that empowers everybody on the planet to become their best selves.”
Challenge
So here’s my challenge to you this week:
Do something you don’t want to do—on purpose.
That project you’ve been avoiding.
That run you’ve been postponing.
That silence you’ve been filling with noise.
Set a timer for 30 minutes.
Do it anyway.
While you’re doing it, notice your thoughts.
The resistance, the excuses, the bargaining.
And instead of fighting them, smile.
That’s the sound of growth.
I have found for myself that over time, the voice that once said, “You don’t have to do this,” becomes quieter.
And a new one emerges—steady, grounded, unstoppable—whispering:
“This is who I am.”
And I know you will find it too.
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P.S. If you haven’t already checked out my podcast, ABCs for Building The Future, where I reflect on my founder’s journey building my AI startup in the open and invite awesome guests building the future to talk about theirs. Check out my learnings on product, leadership, entrepreneurship, and more—in real time!
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