I solve every business problem by firing myself

I'm writing this newsletter on a keyboard that costs more than a MacBook Pro and an iPad Pro combined.

Yes, you read that correctly. A keyboard.

It was meticulously built in California by an artisan workshop, Norbauer & Co., whose retrofuturist designs and meticulous attention to detail have created an almost mythical status in the keyboard community.

I love the story of how it came to be on my desk, because this object (and our investment in the company behind it last year) encapsulates everything that I enjoy about being an investor, and what I think makes Tiny's approach to partnering with company founders special. Though modest in size compared to today's announcement, Norbauer is one of my absolute favorites.

I also like this story because it underscores the point that, in business, emotional and subjective considerations are often as important as the dollars and cents of a deal.

It all began with a serendipitous encounter sixteen years ago.

In 2008, I spotted a guy getting off the L train in Chicago as I headed back to my hotel after a tech conference. We were both wearing the same SEED Conference badges around our necks. I glanced down and saw "RYAN NORBAUER", a name I recognized from a blog post I'd read on my then-favorite productivity blog, 43Folders. I stopped him and said hello.

It turned out that we both ran digital agencies, his specializing in development and mine in design. We were both skeptical of Silicon Valley hype, which is what had prompted us to attend SEED, a conference on bootstrapping creative businesses hosted by our mutual heroes, Jason Fried, David Heinemeier Hansson and Jim Coudal. We swapped emails and quickly became friends, bonding over the shared struggles that come with building services businesses.

By 2010, Ryan had sold one of his startups to OKCupid (Match.com) and was running two others, but he was losing his joy for entrepreneurship. His three businesses had caused him a profound amount of stress, and after years of struggling through the aspects of running a business that he didn't enjoy, he decided to sell everything, vowing to leave the business world forever.

He chose to dedicate his remaining decades to projects driven by curiosity and creativity rather than profit. A clean break from his former life.

Of all things, he went deep into the world of mechanical keyboards.

If you're not familiar, there is a whole passionate subculture of keyboard enthusiasts, obsessed with tactile feedback, unique sound profiles, and meticulous craftsmanship. They seek the satisfying vintage-style "thock" of a mechanical input device over the lifeless whisper of an off-the-shelf keyboard.

Ryan started documenting his build process on online keyboard enthusiast forums, occasionally selling a few extras to help offset the production costs of making one for himself. His work quickly captured the imagination of the keyboard world, and the community kept nudging him to make more and more. He became something of a celebrity in this obscure community, with fans lining up at keyboard conventions to ask for autographs and selfies.

At some point he had stumbled into running yet another business, an accidental little keyboard empire.

Because this was a passion project, he went to extraordinary lengths in the pursuit of keyboard perfection—partnering with a Danish luxury engineering firm to create custom internal mechanics, sourcing rare materials and finishes, and spending countless hours refining every detail from sound dampening to textures.

He became the Enzo Ferrari of keyboards, not by following a business plan—truly, no sane person focused on the bottom line would have created these products—but by pursuing an extreme creative vision, competing for creations that would disappear from inventory within minutes.

Ryan's keyboards are engineering marvels, like mechanical watches in a digital age, but for his passionate clientele they are also deeply sentimental objects. There's absolutely no practical or purely rational reason for them to exist, but they embody the same passion that makes a Patek Philippe special: hundreds of custom precision components working in perfect harmony, assembled by hand, with every detail finessed down to the microscopic level.

In tech companies and finance firms across the world, Norbauers can be found sitting quietly on desks as one of those "if you know, you know" objects, connecting a community of people with a very nerdy but passionate form of taste that many people don't even know exists. They embody nostalgia for the history of computing, and extreme discernment in matters of design and acoustics.

But success brought its own problems. What began as a carefree hobby gradually transformed into a demanding operation. Ryan eventually found himself again miserably consumed by business mechanics, focusing on endless logistical challenges rather than design and engineering. The curse of the creative entrepreneur.

Because of all this, Ryan actually nearly shut the business down a little over a year ago. But, one major thing kept him from clicking "DELETE ALL". Up to this point he had been focusing on making "aftermarket upgrade" components for keyboard enthusiasts to use in modifying existing platforms. But, his real ambition was to create a ready-to-use luxury keyboard entirely from scratch, something no-one has ever done before. He didn't want to throw in the towel without seeing this vision into reality.

This crossroads brought Ryan to our door at Tiny.

What he wanted from us wasn't money. He needed a partner to handle the operational aspects that were increasingly consuming his attention so he could focus on what he was actually good at—designing and creating beautiful products. He needed someone to take the day-to-day off his hands so he could return to his workbench, focusing on matters of taste while knowing that the business was running efficiently, growing its technical capacities and creative options.

He thought of me, his old friend who has often written about having navigated this sort of problem successfully many times (albeit with copious speed bumps along the way) and reached out.

A pattern exists across hundreds of the most successful companies. The brands that endure often share a critical ingredient: a visionary paired with an implementer. Walt Disney had his brother Roy. Steve Jobs had Tim Cook. Coco Chanel had Pierre Wertheimer. Their magic emerged from this symbiotic relationship between creation and execution.

Every creative founder needs someone who genuinely loves the operational work they find draining. Someone who gets excited about the things they hate.

I've confronted this reality many times in my businesses. Over two decades, as each business has scaled, I've invariably found myself in a prison of my own making, buried in operational details that I hated.

More often than not, I've solved this quagmire in a counterintuitive way: by firing myself.

Last year, after becoming completely overwhelmed with the operational details of overseeing some forty-odd companies, I fired myself as CEO of Tiny to refocus on what I do best: setting the vision, telling our story, and acquiring wonderful companies.

My business partner Chris and I found our own Tim Cook in Jordan Taub, a former Constellation Software executive who we'd steadily promoted through the ranks at Tiny over the years. Eventually, it became clear that Jordan was the ideal person to handle the day-to-day operations we'd always struggled with.

Since making this change last June, Chris and I have felt completely revitalized, rediscovering our passion for the work we love and significantly increasing Tiny's dealflow and opportunity set by doing the things we're best at.

This is exactly what Ryan sought to do: fire himself from the agonizing details that distracted from his creative vision.

This is why I understood Ryan's dilemma so deeply. Throughout my career, I've seen how success can become its own kind of prison—especially when creators sell their businesses.

I've experienced this first hand after selling some of my own companies. It felt like watching a beautiful garden I'd cultivated for years being methodically paved over for a parking lot. The DNA that made the company special vanished, replaced by all-or-nothing decisions that prioritized gains over long-term vitality.

These painful lessons shaped my philosophy when founding Tiny: create the acquisition partner I wish I could have sold to—one that preserves what makes a business special rather than imposing standardized "best practices."

We've found three patterns in our acquisitions: founders who want to exit completely, those who just need us to buy out a troublesome partner, and those like Ryan who seek liberation—someone to handle what they hate while they refocus on what they love. This third case is surprisingly common. They don't want to abandon their creation; they want to fall back in love with it.

Most private equity firms, with their McKinsey-trained MBAs and 5-year exit timelines, are fundamentally misaligned with this approach. Ryan needed something different: operational expertise paired with respect for his creative vision.

With all this in mind, I realized that in order for our partnership with Ryan to work, I needed to find him his perfect executional partner. I paired him with my partner Caleb Bernabe—a perfect match for Ryan's sensibilities.

When Caleb isn't running a highly profitable portfolio of businesses at Tiny, he co-owns a hip wine bar in Victoria and obsesses over vintage Leicas and Porsches. I knew that he would understand Ryan's pursuit of perfection—someone who could appreciate both the craftsmanship of the keyboards and translate his vision into a business that can slowly compound its profits and endure for decades.

The most important aspect of our deal wasn't financial. It was psychological.

I promised Ryan three things:

1. If the business failed, we'd both shrug and move on.
2. He could walk away whenever he wanted.
3. He could tell us to "fuck off" if we got in his way.

I encouraged him to pass off anything he didn't enjoy to Caleb and his team, giving Ryan space to develop the brand and product line.

One year into our partnership, and the results speak for themselves. Norbauer just launched the Seneca—its most ambitious keyboard ever—to exceptional praise, and they also recently added legendary keyboard tastemaker and content creator Taeha Kim to their team.

The Seneca stands as a masterpiece of engineering—682 custom parts built entirely by hand, with every component custom-made. Priced starting at $3,600, it's not for everyone, but for writers, coders, and thinkers who spend their days at a keyboard, it's the ultimate escape.

Here's how Ryan puts it:

"The Seneca is my middle finger to the aesthetic homogeneity and economic over-optimization of 21st century life.

Its intricate mechanisms can only be assembled and tuned by human hands, over hours of skilled work—typically by a single artisan, from start to finish.

Every component is custom made (right down to the individually-machined screws), hyper-engineered from first principles for maximum acoustic, artistic, and tactile refinement—costs be damned.

On paper, nothing about this makes any sense. It is over the top. Needlessly lavish. Exuberantly irrational.

And that is the point."

I'm happy to say that the response so far has been wild.

I could quote endless breathless praise from obsessive members of the keyboard community for Ryan's work, but perhaps the most succinct is what the keyboard-obsessed Senior Reviews Editor Nathan Edwards at The Verge wrote in that publication about the Seneca the other day:

"The most expensive keyboard I've ever typed on, and also the best."

Exactly what Ryan has always been going for.

An interesting byproduct of the Tiny partnership is that Norbauer is now a more profitable and sustainable business than before our involvement. What's even better is the whole thing is built on such a beautiful idea: make someone smile when they sit down at their desk.

I love how randomness brought us together, the extraordinary product our partnership enabled (my fingers are tapping across my Seneca's keys as I write this), and how it redefines success by thriving through craftsmanship rather than scale—proving exceptional profitability doesn't require endless growth but instead, exceptional brand, deep relationships with a passionate base of clients, and a commitment to quality.

Ryan tells the story of our investment far more eloquently in a post here. I highly recommend reading it, it includes some fun details and has a few cringe-worthy photos of me from my twenties.

Happy typing.

Originally published in the A $3,600 keyboard and a $66 million dollar investment issue of Never Enough.