Reflections from the trenches of building something stupidly ambitious
As quarter 2 draws to a close, I’ve been tasked with capturing and conveying a few thoughts from what has been the second wildest adventure of my 47-ish years on this planet.
If you’re new around here, here’s what you might have missed from our quarter 1 victory lap: House of Luxury Group was ranked #34 on JP Morgan’s fastest growing companies list, we moved more than a billion dollars in luxury assets on behalf of our clients (including our first US$350+ million real estate asset), and something far less impressive also happened – I was brought in as the company’s CXO.
For the uninitiated, CXO stands for Customer Experience Officer. But we only figured that out after we’d designated the title. Given the absurdly ambitious vision our CEO had thrown down, we determined that the X would be a contextual variable. Simply stated: X = be whatever you need to be and do whatever you need to do to move the company towards its $100 million annual profit goal within five years.
This is my very personal and highly slanted perspective of Q2 2025 – the eye-watering amount of head spins, heartbeat skips, and WhatsApp voice calls that were crammed into the past three months.
Caffeinated Squirrels
For any of this to make sense, it’s helpful if I share a few things about our CEO, Kirsti Jane: she’s high functioning and moves very fast (understatement of the year so far); she has consistently proven that she can sell the unsellable (which only serves to compound her Kanye West levels of confidence); and she has the work rate of three squirrels on espresso during acorn season.
Which brings us to those absurdly ambitious goals: a business that does $100 million in annual profit within five years.
Now, while we’ve internally outlawed the word “brokerage” (because differentiation and stuff), that’s essentially what we are. And brokerage profit margins – relative to total asset sales and depending on the niche – typically hover between 0.25% and 0.5%. Do the math: we’d need to move $20-40 billion in annual inventory sales to hit that target.
Even with the rocketship trajectory we’ve been experiencing, we’d still have some distance to cover. More importantly, consistently achieving those numbers in good times and bad would require something brokerages historically struggle with: diversified, recurring revenue streams with our own products and services.
The Evolutionary Kaleidoscope
So we’ve been knee-deep in evolving and diversifying our business model while simultaneously throwing more effort into making sure the existing model fires on all cylinders. Some days we find ourselves pushing hard in three or four different directions simultaneously, learning a broad spread of lessons by the seat of our pants.
It’s challenging, exhilarating, and terrifying all at once – sometimes it feels like tumbling in a giant kaleidoscope after eating a bag of ghost pepper corn chips. A whole other level of breathtaking.
This past quarter, we’ve brought on seriously heavy-hitting board members. We’re investing in sports franchises. We’re partnering with big brand OEMs. We’re acquiring businesses from tourism to hospitality across three continents.
But here’s the biggest pivot: the real script flip that’s transforming our entire approach:
We’re making the shift from using stories to sell assets, to acquiring assets with which to tell stories.
The Great Inversion
I know that sounds meta, maybe even inconsequential, but this is a fundamental reinvention of how we operate.
From a traditional brokerage perspective, we’re used to determining buyer profiles most likely to privately acquire our off-market listings, then tailoring positioning and presentation to resonate with those profiles. We craft narratives about what ownership might mean to them, who they might become as a result, how it makes their lives better.
We got good at this. Exceptionally good, actually.
But here’s what we realized: when you’re only selling other people’s assets, you’re essentially renting your growth from inventory you don’t control.
Your revenue is hostage to market conditions, seller motivation, and asset availability.
The inversion changes everything.
Instead of waiting for the perfect asset to come to market so we can craft the perfect story around it, we’re now acquiring assets specifically because they enable us to tell the stories we want to tell.
We’re building a portfolio of experiences, not just facilitating transactions.
What This Actually Looks Like
Take our recent sports franchise investments. We’re not just buying teams as financial assets – we’re acquiring platforms for storytelling at scale. Every game becomes content. Every season becomes a narrative arc. Every championship run becomes a legend we own, not just sell.
Our hospitality acquisitions across three continents aren’t just revenue diversification—they’re physical manifestations of the luxury experiences we’ve been selling conceptually. Now when we tell clients about the transformative power of owning a piece of paradise, we can offer them the keys to paradise we actually own.
The tourism ventures aren’t just businesses – they’re experiential laboratories where we can test, refine, and perfect the lifestyle narratives we’ve been crafting for years.
The Compound Effect
This shift creates compound advantages that traditional brokerage models simply can’t access:
Recurring Revenue: Instead of transaction-based income, we’re building subscription-to-lifestyle revenue streams. Clients don’t just buy from us once – they engage with our ecosystem continuously.
Asset Appreciation: We benefit from the value creation of our own assets, not just commission on others’. When we improve an experience, we capture that value directly.
Narrative Control: We’re no longer dependent on someone else’s asset having the right story. We acquire assets that let us write the stories we want to tell.
Market Independence: Economic downturns affect transaction volumes, but they don’t eliminate the desire for extraordinary experiences. Our owned assets provide buffer against market volatility.
The Edge of Comfortable
Of course, this transformation isn’t without its chaos. We’re essentially running three businesses simultaneously: the traditional brokerage (which still generates most of our current revenue), the asset acquisition engine (which requires entirely different skills and capital allocation), and the experience curation platform (which is part hospitality, part entertainment, part lifestyle design).
Some days it feels like performing surgery while learning to juggle while riding a unicycle. On fire.
But here’s the thing about audacious goals – they require audacious methods. Safe, incremental growth doesn’t compound into the kind of numbers we’re chasing. The distance between good and great isn’t bridged by doing more of the same, better. It’s bridged by doing fundamentally different things entirely.
What’s Next
As we head into Q3, the real test begins. We’ve made the strategic pivot; now we have to execute it flawlessly while maintaining the excellence that got us here. We’re essentially rebuilding the plane while flying it, which is either the most entrepreneurial thing we’ve ever done or the most entrepreneurial thing we’ll ever survive.
But that’s exactly where we want to be – at the edge of comfortable, in the space where extraordinary things become possible.
For our potential clients reading this: we’re not just brokers anymore. We’re curators of extraordinary. We don’t just sell luxury – we create it, own it, and invite you into it.
For potential acquisition partners: we’re looking for assets that let us tell better stories, not just generate better returns. If you own something extraordinary that deserves an extraordinary story, let’s talk.
The future of luxury isn’t just about having access to extraordinary things. It’s about having access to extraordinary experiences that transform who you are. And increasingly, we’re not just the middleman in that transformation – we’re the architects of it.
Welcome to the next chapter of House of Luxury Group. It’s going to be a wild ride.
Simon K
CXO – House Of Luxury Group