July 9, 2026
We covered A LOT of ground in this one. Whether you are an online creator, an entrepreneur, a self declared freethinker, or you simply find interest in philosophy and psychology, this conversation has something in it for you to take away.
I am truly grateful to have spent the morning talking with Arooba Asim, who I know as Ruby, and who I think is one of the most thoughtful, insightful people publishing digital content today.
Ruby is a wife, a writer, and the COO of Mogul Media, where she leads a team of thirty writers producing content for founders, CEOs, DTC brands, and SaaS companies. When we first started planning this conversation she described herself as an operator, and that word turned out to be the key to everything else she shared.
Her story starts with a diary she kept at seven years old in Pakistan and runs through her family completely starting over in Ontario, 40-hour weeks at a thrift store at fifteen to buy a bed set for the room she shared with her sisters, and a Twitter account in 2019 that turned a lifelong writing habit into a passionate career. Now she lives in Latin America, repeating her parents’ journey in a new language, running a business by day and writing a novel about immortality in the background.
What I appreciate most about Ruby is her honesty about the things people usually perform around. Money. Advantages. The dream you keep warm while you build the thing that funds it. She said one line near the end that I wrote down mid-conversation and am still sitting with:
“Life can be extremely simple, but what we’ve been through can make it hard to choose that simplicity.
You can also listen on Spotify
You can get in touch with Ruby in any of the following ways:
Substack: Ruby
X: @tishray
Instagram: @therealroobz
What we cover
The diary she’s kept since she was seven years old, the entries that read “I went to the park today and it was fun,” and why flipping through it is her favorite party trick
Studying psychology at university, starting to write on Twitter in 2019, and the classical education company that hired her and turned a lifelong habit into a business
Leaving Pakistan at eight, watching her parents start over in their 30s with five kids, and the sentence she still tells herself in hard seasons: “You can do this, because your parents moved to a new country with five kids”
Moving to Latin America now, repeating her parents’ journey, and the moment she realized she’d been carrying an invisible expectation that everyone on earth speaks English
Unfair advantages: two-parent homes, stable childhoods, money in the family, and why everything she’s building is meant to hand those advantages to her future kids instead of making them learn the hard way
Her dad coming home from work and taking the kids to Dollarama to pick out whatever they wanted, and his rule: if you have money, spend it, don’t hoard your wealth
Working 40-hour weeks at a thrift store at fifteen to buy a bed set for the room she shared with her sisters
The family dog she bought at sixteen with her own savings, who passed away just two months before we recorded
An honest conversation about money: “If you have money you will get further in life,” and the choice between denying that reality and working with the cards you’ve been dealt
Passion as skills rather than a task, and the pattern recognition sitting underneath her psychology degree, her business, and her novel
“I love my business, but it’s not my dream,” and why the revenue engine and the dream should be separate machines
The Leila Hormozi post about motherhood and choosing what matters most in the phase of life you’re actually in
What a COO does all day: creating efficiency, wondering how the head chef runs the kitchen, and getting a team of thirty to see what she sees in her head
Leadership as making people curious about themselves rather than curious about things
The scorekeeping wiring she inherited, and the list of good things she writes every night to counter it
Jung’s shadow, the golden shadow, and why willpower is a finite resource that will eventually lose to a desire you keep suppressing
The writer who shelves the dream long enough to start resenting the people around them for it
Shame and guilt as the lowest vibrational states, and tracing “I’m not good at math” back to a belief somebody else handed you
“If you’re so smart, why aren’t you happy,” and the smart person’s habit of rejecting the simple answer because it feels too simple to accept
“Don’t pick the toxic person,” the relationship advice she knows people will hate her for
The pain-as-art identity she had to drop when she realized she was sabotaging herself just to relate to the world
My own sliding glass door moment, getting sober two and a half years ago, and what an ayahuasca ceremony in Peru finally let me put down
The line I wrote down mid-conversation: “Life can be extremely simple, but what we’ve been through can make it hard to choose that simplicity”
AI leveling the playing field, 18-year-olds building apps to $200K a month, and her answer to whether closing the gap is always a good thing: “I don’t know”
Why learning a language hasn’t gotten easier with ChatGPT, and what shortcuts cost your long-term memory
The Count of Monte Cristo, 1,300 pages that distill down to “wait and hope,” versus the Instagram carousel version you’d forget by morning
The Great Divorce by C.S. Lewis, the book she picked up and put down for years until the exact moment she was meant to read it
Whether there will ever be another classic, Michael Jackson, and a culture too fragmented for anything to reach everyone
Pete Dawkins, the halftime speech at West Point, and the clouds that parted while he spoke
Astrology, stelliums, and the birth charts of people who seem born for what they became
Being Muslim while studying every religion she can, Jung’s collective unconscious, and the girl who drew the crucifixion without ever being taught it
Using Marcus Aurelius to motivate her team, and developing people so well that their next employer inherits the benefit
The novel she’s writing: two lovers who opt into a ritual for immortality and discover it strips away the very thing they did it for
