Behind The Scenes: My Conviction in The Investments I Make
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.
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
I 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?
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
By 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
I 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?
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
This 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.
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.
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:
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)
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!
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…?
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 Arc
This 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).
What’s All This Hype About? (Features)
Okay, here’s 3 things (though there are many more) that are the bedrock of what will make Arc operating system for the future of the internet.
1. Spaces & Profiles
Arc has this special thing called “Spaces”. Once you begin using this feature, along with the built-in organization philosophy, you’ll never be able to go back to accessing the internet the old way again.
When you are in one of your spaces, you are in a focused environment, void of all the distractions across the 20+ other tabs you probably have open.
You might make a space for marketing (content creation), entertainment, projects you are working on, reconciling the company books, or anything in-between.
But wait! Some of those are personal things, while others are for work! I hate mixing the two!
So this is where Spaces have a second layer to them called “Profiles”. Take that entertainment space, pin your YouTube, Twitter, Netflix, and simply set that space to “Personal”. Log into your accounts once, and just like that, you’re in a totally personal environment.
What about those other spaces?
Set the Marketing space to your “Work” profile and log into all of your work accounts. Now when you are in the “Marketing” space, you’re fully siloed in your work environment. This means your search history, logins, and extensions are all tied to your profile and thus, your space. Oh, and even those little “favorited” icons at the top. Accessing your email across all your work spaces? Go ahead and favorite it, now it’ll be in the same spot for each work Space you visit!
Now set a fun color/theme to give each space a nice visual cue when swiping between them, and find yourself getting engulfed into what you’re working on. All your open tabs stay right where you left them, in the specific space you visited them in. Accidentally visit a few work sites in your personal space? Simply select them and right-click → move to one of your work Spaces! 👌
Arc can now keep you focused, organized, and no longer context switching, the #1 killer of productivity.
2. Folders & Grouped Tabs (Split View)
Okay, Spaces are super cool! But how do I organize them?
With folders of course!
And sub-folders, and sub-folders, and more sub-folders.
This rabbit hole goes deep! 🕳️🐇
Have you gone too crazy with folders? No fret! Right-click the parent folder and turn it into its own standalone Space!
Now you’re getting the hang of it! Go deep with folders and horizontal with spaces. Expand in all directions!
Have any websites that you’re regularly jumping between or open in two separate windows? Take for example this blog post that I’m writing. The editor is in markdown, and that is rendered in the actual page. Cool, lets create a split tab view that has the hidden blog preview URL in one half and the editor in the other:
And this is what it looks like when you’re in one of the “split views”:
Build it once, pin the tab group split, and easily reset the tab group back to the original group if you ever accidentally navigate away. It’s like a “reset” button built right in.
3. Powerful Navigation & Built-In Apps
Arc is built atop Chromium (the open-source foundation of Chrome), which means all of the extensions you use and love in Chrome, work out of the box with Arc.
But that’s not all!
The team at Arc has built in some thoughtful widgets right into the browser itself. Play music in one tab and then jump somewhere else? An audio control widget pops right up in the bottom left corner so you never wonder where that audio is coming from again.
Watching YouTube in a tab but then leave the tab to look something up real quick? No problem! A floating video widget pops up and follows you everywhere you go. It’s all of these tiny thoughtful experiences baked right into the browser, that makes it feel more like an intelligent operating system, built specifically for how we all actually use the internet.
Oh! And keyboard shortcuts. Shortcut all the things! You can set anything to be any shortcut combo you’d like (if you’d like). Do you ever find yourself copy/pasting the current URL you’re in?
And just like that, you can paste it anywhere. No more clicking into the URL bar, selecting all, copy. I know it sounds minor, but it’s these micro actions that I didn’t even realize I was using dozens of times a day, that makes navigating the internet feel kludgy. Leveraging this simple shortcut, it now feels like the internet is actually built for sharing again.
Why Does This Really Matter?
Okay, you sound pretty excited about this browser and it has some cool features… but at the end of the day, it’s still just a browser, no? How much more useful could it really be?
Oh boy, am I glad you asked!
Arc Multiplayer Vision
Browsers, everyone’s portal to the internet, are notoriously single-player. You have your bookmarks, your search history, your logins, your extensions…
But what about me??
Most things in life are more enjoyable with others, so why not also have the thing that we all use day-in-and-day-out also take advantage of this fact?
Arc In Business (Internal Team)
I’m someone that has been slightly obsessed with documentation. Not what most companies try to do and fail, but creating a shared brain for your company. One that is actually helpful, and allows for building repeatable processes. Documentation that is built with saving your team time as the sole purpose. Not just documenting for the sake of it.
Documentation done well should save you and your team time. It’s IP for your business.
Well, we have stellar team collaboration tools like Slite, Notion, and Loom to write and store said documentation… But how about accessing it when and where you need to? That’s where these tools fall apart and aren’t accessed as much as they should be.
Reconciling your books? Jump into your “Admin” space, and open up your “Reconciling” folder:
And just like that, all your useful documentation is already pinned, organized, and open.
Now this is great, for me… But now imagine being able to build this once, and share it across my entire team. My CPA even. What if my CPA just had a shared “reconciling” space for each of his clients. Imagine the collaboration efficiencies.
Every business process can now be a space/folder structure, and shared with your team. Most companies are using dozens of different apps, for different things. Multiplayer Arc will finally rope in all of them. Allowing the right app/document to meet you, right when you need to access it — created once, and disseminated across the entire team.
Arc In Business (External Customers)
Since we are creating sometimes complex business processes and automation/integrations for customers, a big part of what we do is create shared training documentation for our customers.
The sheer amount of time that goes into creating this though, that at times feels like it is rarely ever even referenced by the customer, is insane.
If we could bake in our shared documentation and training videos right within our customer’s work environment (Arc), it would actually get used. The sheer amount of time and money saved (for us and our customers). The reduction in support tickets, while supplying an even better customer experience. Not to mention the efficiencies gained from our customers onboarding new employees.
I can actually finally envision a scalable and organized company, can you?
Arc In Schools
Professors are currently strapped to using outdated software like Blackboard, for sharing assignments, updates, reading materials, and messages.
What if that was made 10x better and more engaging with Arc multiplayer Spaces?
Imagine the virality that would come from your professor using Arc to share assignments with your class, adding in supplemental reading material and referenced videos in the same way everyone currently accesses information.
Group projects could take advantage of a shared Space with your team, collaborative notes, flexible easels, and more.
Could Arc be the browser for education as well?
While getting schools and professors onboard might be tough, you actually just need the students to get onboard. Something that is already beginning to happen…
So If You Ask Me The Question Again…
“How do you have conviction?”
You can see now that I just easily wrote 4,400+ words about a browser.
While that might seem like a lot, it’s only just some of the thoughts that have come from thinking about a fascinating problem I have experienced for over a decade.
So now I’ll answer your question by asking you the same question:
What is a problem that you’ve been thinking about in the back of your mind for a while?
And, if you found a company that was doing a kick-ass job at solving this problem, would you have the conviction to invest?
I think I already know the answer
If you made it here, all I can say is thank you. I appreciate you. Oh, and here’s a special invite link that allows you to skip the waitlist (which will work for the first 10,000 people) 🔥