People often ask how I decide what companies to invest in, and where I get the conviction to actually put money in.
In thinking about it, most of my investments have come from decades of thoughts about a specific problem that a company is solving.
This is the story of how and why I believe The Browser Company (Arc) is the operating system for the future of the internet.
Here is some insight into the thousands of hours and deeply emotional personal experiences (erm, what…?) spanning the past decade, that ultimately led me to posting the tweet above.
July 2014 - It All Started With A Chromebook
July 2014 - It All Started With A ChromebookI got my first Chromebook as a college graduation present from my mom back in 2014. She could immediately tell that she had made a mistake.
You could see the thoughts as if they were painted directly on my face (I couldn’t even pretend to hide it):
Where did this come from and… why?
She handed me the receipt and gave me permission to return it if I’d like, saying that it wouldn’t upset her. Oh, and added that “I’m incredibly difficult to shop for” – Yep 😅 and so I returned it.
Awful son, right?
Well, for context: I learned how to build my first gaming PC at something like 13, and then proceeded to build more than a dozen or so thereafter (4 for myself, a handful for family and friends, and quite a few more for some of my clients). Oh yeah, I was also four years into running my IT Services company. Not to mention, I also already had a top-of-the-line Windows Ultrabook (laptop) that I was super happy with. So in summary, I literally had no use for it.
Don’t get me wrong. My mom wasn’t wrong, I loved Chromebooks (just… for other people - not myself). She heard me regularly talking about it because I was often recommending them to family, friends, and even clients.
Why? Because Chromebooks were so easy to setup, backup, manage remotely, and hey, no antivirus required! You spill coffee on your laptop? All good! No files are lost and no programs require reinstalling. Simply grab a new Chromebook and log into your Google account. Good as new!
This convenience is what later became a healthy obsession:
What actually makes a computer, a computer? 🤔
As the years followed, I thought about this question a lot.
2015–2017 - Oh Shit, Wait?
2015–2017 - Oh Shit, Wait?For anybody who doesn’t know what a Chromebook is, it’s a laptop that is centered entirely around Google Services (Chrome, Drive, Gmail, Docs, Sheets, etc.).
In explaining to clients why Chromebooks (ChromeOS) was a great path forward, I got back no shortage of concerns:
“But what about Microsoft Word and all of the other software that I use?
They couldn’t really argue with that. And by convincing clients to deploy Chromebooks across their organization, I gained more and more conviction that all of their work could be done in the browser.
Because I was recommending Chromebooks to everyone else, I started reflecting on my own workflows too.
On two fronts in-fact:
Personal: Working on two separate computers that didn’t at all speak to one another was causing a lot of frustration. Having to re-login to everything, setup and configure every installed application twice, development environments, etc. I was maintaining two totally siloed Windows computers and it was becoming painful to keep everything in-sync (PC & Laptop).
Work: At this point I was managing dozens of computers for clients and I was constantly wondering how I could do more of that remotely and in a more efficient way. Windows and MacOS machines at the time were a pain to setup and manage at scale, and nearly impossible to remotely. Even with expensive RMM (Remote Monitoring & Management) software. It was such a pain.
I also started realizing that 99% of my daily usage was actually inside of Google Chrome:
🤯
October 30, 2017 - I Made The Switch
October 30, 2017 - I Made The SwitchBy recommending clients to deploy Chromebooks across their organization, I gained conviction in the simplicity and scalability that they were looking for.
Google released the Pixelbook, a premium Chromebook. It was my time to put my money where my mouth was.
Show Don’t Tell
Show Don’t TellI decided to use a Pixelbook (Chromebook) for 100% of my working day.
I’ll be the first to say it… It was a difficult experience. Not for the reason you’d think though! It wasn’t because the computer wasn’t capable – I got all of my work done without problem, it was great. The tough part was actually others. Every single person that I crossed paths with from that point forward was wondering only one thing… Why?
It’s super exhausting holding an opinion that nearly everyone opposes.
“Wait… What?? Why aren’t you just on MacOS or even Windows? Aren’t you literally just using a glorified Chrome browser?”
The answer is “Yes, but…” (let’s just say this gave me a lot of practice in refining my “why” over the years to come).
People saw it as just a Chrome browser, but what I saw was the future of the internet.
That with it, all computers in the future will just need to be portals – slabs of glass, that with a simple login will transform into your perfectly configured workspace, leaving you right where you last left off.
All of this possible from anywhere. There will be no more “forgetting your laptop at home” or “I’ll have to show you later”. You’ll be able to feel at home with the ability to work and play from anywhere at any time on anyone’s device. That to me, was the future vision of ChromeOS.
Eventually I even wiped my Windows Ultrabook to install CloudReady (an installable version of ChromeOS) and recorded a comparison video between it and the Pixelbook because I wanted to show people that they too could get access to this experience all without even purchasing a new computer. This software would be the way that every computer in the world could eventually to get access to the above vision. I was down the rabbit hole and all-in at this point.
Something Was Missing…
For this vision to come true though, Chrome was still missing some things. Tab management and bookmarks hadn’t evolved since the creation of the browser (over a decade ago).
Take for example your browser right now. Are you using bookmarks? If so, are they even organized and useful? Or are they actually a total mess like most people? Ever accidentally close a window with all your tabs open, jumping between different browser windows to attempt to segment your work? It’s all hectic and a complete mess.
So I got to searching and installed pretty much every single tab/bookmark manager on the market. Used Toby personally for 6 months and even deployed it to a few of our clients to try and bring the “portal vision” of Chromebooks to life.
Adoption of these tools was tough though as it required a lot of setup and training along with a major shift in habit. I understood why there was pushback, and that’s where I ultimately settled on building a custom dashboard management system for clients to use. Simply replacing their typical Chrome homepage and new tab page with a custom page we created, essentially building their companies’ standardized “portal to the internet”:
(This screenshot is that page for one of our customers – 43North)
It was a decent solution for the time. Definitely not my ideal vision imagined, but our clients enjoyed it enough. Not to mention, it was incredibly easy to deploy across the company, little to no training required, because it was just a webpage with links to the pages they needed to access.
(Crazy enough, some of our legacy clients are still using it to this day) 🤷♂️
August 8, 2018 - Could This Be The Vision?
August 8, 2018 - Could This Be The Vision?In my never-ending search to find my “portal to the internet Chrome experience”, I stumbled upon a totally re-imagined Chrome extension and tab management experience called Workona:
(As you can see, each workspace has unique tabs that you can easily jump between to keep your work segmented)
It was ChromeOS + Workona that enabled me to finally experience a glimpse into what I had always hoped for the “portal” vision to be, it mostly checked the boxes:
- A better way to build out workspaces and processes for personal and business usage
- Deeper integration with the existing web apps we love and use today
- Sharable workspaces, build out your sales process and share the created workspace with your sales team
- Accessible from any system (if you logged into a Chromebook, it would auto-install the extension and just like that, you’re where you left off)
The following year was me just giving tons of feedback, having a couple of my clients implement it so that they could be guinea pigs for a wider rollout. From there, I’d collect feedback from them, pass it along to Workona, and then rinse and repeat.
September 10, 2019 - The Offer That Changed My Life
September 10, 2019 - The Offer That Changed My LifeThis email was incredibly unexpected and changed the course and direction of my entire life. At the time of this email, I was growing my business out of my bedroom in Buffalo New York, and absolutely loving what I was doing.
I had pivoted away from the traditional MSP IT services, and over to SaaS integration, automation, and business process design. I was growing and playing with software every day in my free time, and the business was generating over $150k per year – as the founder and sole employee, I was happy and comfortable. It was the type of lifestyle business that one might hope to one day have, and after 9 years of grinding, I had finally made it here.
Comfortable
This is not a word I use lightly.
In-fact, it’s a word that actually broke me.
(I’m getting emotional even as I write this – I can’t overstate how much this single word has had an outsized impact on my life).
I’ve had plenty of job offers from software companies that I’ve absolutely adored over the years, but I’ve always ultimately declined through simply reflecting on one of my cornerstone realizations:
I already get to work with all of the software that I love every day, while continuing to discover new ones to add to that list. If I could describe my dream job, it would be playing with new features, beta testing cutting-edge new software, giving product feedback, all while bending and breaking what is possible through integration.
I already had my dream job in many ways.
But this opportunity felt different. For the first time in my life, the word “comfortable” was staring at me directly in the face and it absolutely tore me apart.
- Head to Silicon Valley and dive deep into the unknown?
- Stay in the comfort that is my bedroom in Buffalo?
This is what played through my head day-in and day-out for weeks. I was a mess.
I finally decided to take the leap. Based on what? My new life cornerstone:
If you’re comfortable, you’re not growing.
So I chose to dive into the tech capital of the world, as an early team member of one of the most crazy talented teams that I had ever met, on a product that I had been obsessed with and using daily for a year. Working alongside them on a vision that I had been daydreaming about solving, and in a way, trying to solve in the micro for myself and clients my entire career.
I told all of my family and friends that I was leaving, and spent the next month working on delegating my one-person business so that I could take a backseat in it, to experience the energy of a proper startup.
Complexities
Some unforeseen complexities came up which resulted in it not making sense for me to join the team.
I stayed at my company as a huge supporter of Workona, but the comfortability damage was done. I was now seeking discomfort – so I kept the 1-way plane ticket, with a new destination in mind:
San Francisco
With no reason to be there other than discomfort, I:
- grew personally in 2 months more than I had the prior 2 years combined
- met my now co-founder and wife
- made my first angel investment which jumpstarted my angel investing career (and the reason why you’re reading this post right now)
(Now these are all stories for a different day as it’s not directly related to what I’m trying to get across with this article.)
April 3rd, 2022 - Enter The Browser Company (Arc)
April 3rd, 2022 - Enter The Browser Company (Arc)I had been hearing about a browser that was in the works on Twitter by a company aptly named “The Browser Company”. Now I’ll admit, I was incredibly skeptical because I had tried “the browser-based solution”, with companies like Shift amongst others over the years. And while they are always cool out of the gate, I continually found myself going back to Chrome after that “new product productivity boost dopamine” quickly wore off.
(Keep in mind, I was also still using ChromeOS as my daily driver, and just left my Windows PC at home, so I couldn’t even use these browser-based solutions anyway – point being: they’ve never been good enough to make me actually miss my Windows PC).
That said, I gave them the benefit of the doubt, requested access, and waited for a while to get in. 🤞
June 21, 2022 - You’re In!
June 21, 2022 - You’re In!Success! Wait… One little problem, I don’t have a MacBook 😅
Stole my wife’s MacBook Air and installed it to play around a bit.
Beautiful onboarding and a level of refinement and purpose that I rarely see in a product. Especially not for a product that is still some level of “private beta”. Thoughtful tab management, tab grouping through folders, oh, and workspaces (spaces) — I’ll get to this later… All I can say is wow… I’m impressed.
Okay, this once little problem has officially turned into a big problem. I have no actual way to use Arc daily, so how am I supposed to give it an actual shot?
Not to mention, my wife was officially jealous when she saw me using Arc on her computer. Which of course led to me asking the team for access on her behalf so I could live vicariously through her (and make her day of course!) 😁
(Arc requires a whitelisted email address to access and save your spaces, so we couldn’t just share my invite unfortunately).
July 15, 2022 - Did I Really Just Do That…?
July 15, 2022 - Did I Really Just Do That…?I did the unthinkable… and preordered an M2 MacBook Air.
I’d be lying if I didn’t admit that Arc was a factor in that decision. I mean… it’s one of the few things that I knew I’d never be able to get on my Chromebook. Arc on ChromeOS just isn’t possible since ChromeOS is Chrome… So at this point, I clearly had no other choice.
July 25, 2022 - The Day I Installed
July 25, 2022 - The Day I InstalledThis was my fist ever Mac, and with it in hand, would you believe that the first thing I did was install and setup Arc (I mean, if you’re this far in the article, that point is probably relatively obvious…)
Now when I go back to my Chromebook in the off-chance, I now feel like it is missing something. The platform that I thought would be the operating system of the future (ChromeOS) was now missing my synced spaces, pinned bookmarks, folders, and more (will explain these features in the next section). I could no longer “pick up where I last left off”. That said, what I can do now is jump on my wife’s computer and be thrown right into where I left off, all with Arc.
The portal to my workspace is now accessible in more locations. On any computer (well MacOS for now, but Windows is being worked on and is coming). Point being: I now see the vision of the portal, but now with less friction. Instead of changing someone’s foundational operating system, there is now an operating system masked as a simple browser that can be installed with just a click, just like any other app. This eliminates the largest friction-point that comes with ChromeOS (purchasing a new laptop & learning a new OS).












