A personal holding company. The realization doesn’t arrive as a lightning bolt. It arrives quietly, almost reluctantly, after enough repetition makes denial impractical.
I keep replaying the same conversations in my head – the acquisition calls, the half-answers, the missing systems, the founders who want an exit but have never actually prepared for one. And layered on top of that is my own recent experience: having just come through a full due diligence process myself, from both sides of the table, twice over.
I know how unforgiving that process is. I know what gets examined, where pressure builds, and how quickly optimism collapses under scrutiny. I know how much discipline, structure, and advance preparation it takes to move through it cleanly. Most importantly, I know how rare it is to be genuinely ready.
That contrast is hard to ignore.
What I’m seeing isn’t a lack of ambition. These founders are driven, capable, and serious about what they’ve built. What’s missing is perspective – the kind that only comes from having been through the exit process end-to-end, not as an advisor or observer, but as the person whose company is under the microscope.
And for the first time since selling my own business, something begins to feel obvious.
There is a real need for experienced operators who have actually been there – not theorists, not motivational coaches, not people selling frameworks – but founders who understand what it takes to turn a running business into a transferable asset.
Not because it’s lucrative.
Not because it scales beautifully.
But because the intellectual challenge is real, and the work matters.
At the same time, another truth sits alongside it, equally clear.
I don’t want this to be the center of my professional life.
Coaching as a Response, Not a Destination
As the idea takes shape, it becomes clear what this is – and what it isn’t.
No, I don’t suddenly want to become a full-time coach. I’m not interested in building a practice optimized for volume, or in positioning myself as a public authority dispensing generic advice. That doesn’t appeal to me, and it never has.
What does appeal to me is the work itself.
Sitting across from an ambitious founder who wants an exit but doesn’t yet understand what that actually entails. Helping them see their business not as a personal extension of themselves, but as an asset that must stand up to scrutiny. Working through the uncomfortable questions early, before the stakes are existential and the timelines compressed.
That kind of work is intellectually satisfying. It’s precise. It demands judgment, pattern recognition, and honesty. And it’s work I’m unusually well suited for, precisely because I’ve just lived through it.
I know what buyers care about because I’ve been interrogated by them. I know where founders tend to overestimate readiness and underestimate fragility. I know which gaps are cosmetic and which are fatal. That perspective doesn’t come from reading about exits. It comes from being inside one.
So advisory and coaching start to make sense – not as a business to be scaled, but as a focused, high-leverage way to work with a small number of founders who are serious about where they’re headed.
Important, yes.
Central, no.
Because alongside that clarity sits an equally strong instinct: I still want to build.
The Pull Toward Building On My Own Terms
The more I sit with the idea of advisory work, the clearer another truth becomes.
As much as I enjoy the intellectual challenge of helping founders prepare for an exit, I don’t want my professional energy to be spent primarily inside other people’s businesses. I don’t want to clean up inherited complexity or retrofit structure onto decisions I didn’t make. I’ve done that before, and I know exactly how much friction it carries.
What I want is authorship.
I want to build systems from first principles. To design the structure intentionally rather than reverse-engineering it later. To create products, platforms, and tools the way I think they should be built – with clarity, leverage, and optionality designed in from the beginning.
Buying an existing company increasingly feels like the wrong vehicle for that. Not because it can’t work, but because it starts with compromise. You inherit assumptions, habits, and constraints that shape everything that follows. Even when the business is sound, you’re still adapting to someone else’s architecture.
I don’t want to adapt. I want to design.
That realization settles quietly but firmly. The excitement I feel isn’t about acquisition anymore; it’s about creation. About starting with a blank sheet and building something that reflects how I want to work now – smaller surface area, higher leverage, fewer dependencies, cleaner systems.
At the same time, I’m realistic enough to know that I don’t want to build just one thing again. I don’t want another monolithic company that consumes everything around it. What I’m drawn to instead is something more modular – a structure that allows multiple ideas to exist, evolve, and compound over time.
That’s when the shape of it begins to appear.
Not a single startup.
Not a fund.
But a personal operating platform.
Designing the Container
Once I start thinking in terms of structure rather than individual ideas, everything begins to feel more coherent.
What I’m circling around isn’t a single product or a single company. It’s a container – a way to hold multiple ventures, experiments, and operating ideas under one roof, without forcing them into the same lifecycle or level of commitment. A structure that lets me build, operate, and evolve businesses deliberately, without recreating the sprawl and complexity I’ve worked hard to leave behind.
A personal holding company starts to make sense.
Not as a grand strategy, but as a practical response to what I now know about myself. A framework that allows me to launch and operate technology businesses on my own terms, while keeping optionality intact. Some ideas may grow into substantial ventures. Some will fail spectacularly. Others may remain small, profitable, and self-sustaining. A few may never make it past the prototype stage. That’s fine. The structure doesn’t demand that every experiment become a centerpiece.
What matters is that the container is intentional.
I don’t yet know what the portfolio will include. I’m not forcing a thesis prematurely. But I am certain of one thing: whatever I build next will be deeply shaped by technology – and increasingly by AI. Not as a buzzword or a pitch, but as an enabling layer that fundamentally changes what small, focused teams can accomplish.
AI shifts the leverage equation. It compresses time. It reduces the need for scale where scale once felt mandatory. It makes it possible to build systems that would have required entire departments not that long ago. For someone like me – drawn to structure, tools, and clean systems – that’s not abstract. It’s catalytic.
So the direction becomes clear, even if the details do not.
I’ll work with a small number of founders who want to prepare their businesses for an eventual exit, because that work is meaningful and intellectually honest. But the center of gravity will be elsewhere – in building and operating my own ventures, inside a structure designed for clarity, leverage, and longevity.
I don’t have a name for it yet. I don’t need one.
What I have is something more important: a sense that the next chapter won’t be about replacing what I sold, but about designing something fundamentally different.
And for the first time since the transition period ended and the inbox went quiet, that feels like enough to move forward.
Cheers,
-Thomas
