One thing uncomfortable to talk about as a tutor: you’re not just in it to help kids. You’re in it for the validation.
To a student, to a parent, I can be a savior. I'm smart. I get paid well. I'm trusted. I get gifts: thank you cards, bottles of fancy tequila, “we couldn’t have done it without you’s,” admiration. I’ve been called a visionary, a guru. I’ve been told that nobody could get through to their daughter/son, but then there was me.
So, it’s been 15 years in the industry, and I’ve been spoon fed validation like this every year for a decade and a half. At the heart of this validation: it wasn’t true. My secret was that I created conditions to let students be. That’s it.
And then, I decide to build a product that not only exists without me, but is actually better without my presence: the Room HQ. A scalable version of what I try to do, with even less of me.
A room energetically charged, in the heart of Venice, that can be used for high stakes poker on a Friday night, SAT Sunrise Sessions on a Saturday morning, Omakase with jaded finance bros on a Saturday night, and each group would think that the room was built for specifically that purpose.
To do this, I can’t exist. I have to be a ghost. I can’t be the center of it. I have to be invisible. I can’t matter.
What matters the most is the machine that believes in the power of humans and their relevance, that AI allows creatives to be limited only by their imaginations rather than their access to technical skill or money to hire technical talent. This belief in humanity allows the room to exist and thrive, not a central guru-figure dominating the attention and adoration. This is why Ashland Prep has no me, no credentials, no testimonials. Just my writing.
So when three high school students come to the Room HQ for the first time, expecting an adult (me) to be there, to hover, to have to perform and give thanks for that adult, and they don’t have to: they’re here with no expectations, no goals other than the ones they create for themselves, no need to perform for anybody but themselves, no need to even perform at all, just to be… and they draw beautiful sketches on the table, they wander Venice, they come back, they maybe doom scroll for 30 minutes and… that’s it, no "OMG THANK YOU SO MUCH," no “THIS CHANGED MY LIFE” — I have to remind myself that this is the machine in action. I’ve designed it to make adults irrelevant, to ensure students themselves ARE genuinely the center and not my ego, and that the permissiveness of the model is what makes it work, because I'm creating conditions for real motivation to happen. And yet, here I am, a glutton for validation, yearning to say “hey just checking in on how it went yesterday,” even though I know this will kill the machine, only serve myself.
On January 29, 2025, envisioning the concept: I wrote on my whiteboard: “Restraint. Do Less.” I have to let it run. Let people do their thing. Let things grow. Let students come in and out, let it evolve into what it needs to be. This is the biggest challenge of building something like this: even more than cash flow. Emotions, deep seated, probably stemming from when I was 14. The 14-year-old-boy emotions that just stick around. I think it does for all of us: the teenage versions of ourselves that feel really hard.
Just have to remember what I’m building, and why.