The Road to $40 Million at Squared Away
Michelle recently shared how we passed $40m in all-time revenue at Squared Away. Check out her post on X. I wanted to share a few thoughts on how we got here, lessons learned, all of our financials, and my personal journey to get here.
To think we started this company because of one phone call in 2016 is unbelievable. We had decided to let our team work remotely and our VCs were still telling us we need to offer free lunch to our team to compete with hiring out of Twitter, Facebook, and the other tech giants. I decided to do something different and I wrote this blog post "Let's get real about perks..." about giving people time back instead of expensive perks that don't help make people more productive.
I’ll never forget that moment.
I asked michelle “I wanna give every employee a personal assistant instead of free lunch, a perk to give people time back. do you know more military spouses and can we offer personal assistants as a perk to our entire company?” She said “there’s 300,000 military spouses in the US and we have the highest unemployment rate in the country. 30%+! I could have you 10 assistants tomorrow.”
And Squared Away was born.
An incredible mission, a wonderful business. It’s surreal to cross $40m in revenue, pay over $26m to military families, 1000s of customers and over 400 team members. It’s been so amazing to watch Michelle (who started as my assistant) turn into a bad ass CEO, grow this into such a great company, and be so open and vulnerable about how the business is going. Check out her post about our mission, revenue, operating metrics, net income, everything. This has been one of the most rewarding companies to be a part of and watching michelle lead and grow and be a great business partner has been one of the coolest things to see in my career. Since there’s over 300,000 military spouses, our work is just beginning.
But for me, it started even before this.
I read '4 hour workweek' in 2009 and Tim Ferriss said to hire Virtual Assistants overseas to do most of our work. Email, research, calendar, etc. It seemed crazy but I was curious. I started to explore it.
People thought this was the dumbest thing they'd ever heard. Our ego likes to tell us that "only we could do this job." Turns out for most things, this isn't true at all. Our ego and need to feel valuable drives us to do a bunch of things that someone else could do better, faster, and much cheaper.
I spend most of my time these days thinking about this quote from Kevin Kelley, founder of Wired:
I have a practice of giving away my ideas to the internet because if I'm supposed to do only things that I can do then if someone on the internet can do them then it wasn't meant for me to do
It's one of those quotes that sounds crazy, but it reminds me of how the world works today and how to find the thing only I can do. People always try to protect their ideas, I literally do the opposite. It's only led to better conversations, better ideas, better relationships, and better focus for me.
It's this idea of outsourcing that led me to Zirtual in 2014, which was an American based platform to hire a virtual assistant. That’s how I met Michelle. She worked as my assistant for 3 years before we ever started Squared away. Then overnight Zirtual blew up from bad management and financial planning. Michelle and I didn't need Zirtual to keep working together, so that's what we did. We kept working together and then started Squared Away on the side.
Here’s something most people think is crazy: we started Squared Away before we ever met in person. We worked together for 3 years and only met on Zoom.
In 2014, people thought this was the dumbest thing on earth. People mocked me all the time. I've always found it weird to mock something you've never tried. Sure, it sounded weird but the time it was saving me was insane.
When we started Squared away, we knew there was a branding problem. We also knew the military spouse community was special. So we changed everything. I remembered something Ron Johnson (inventor of the Apple Store) said once at a company all hands we had:
In business, be the best or be the cheapest, never get stuck in the middle.
We weren't going to be cheaper than the Philippines, but we could be the best. So that's what we did, we leveled up everything.
We never said Virtual Assistant (VA), we called our team Chief Executive Assistants. We leveled up the brand so they were proud to work here and people were proud to hire them. We built a training program that was rigorous and challenging. (Only 7% of people make it through training, that's a harder acceptance rate than Harvard!) We built a culture around being the most proactive people on earth. We think about problems before you know you have a problem. We priced premium. We offered the best assistant service you could offer. We changed the perception of remote work to just be work.
Find the best, have the best training, brand the best, and price like we are the best. What we discovered is that at $40/hr, this was still insanely affordable for everything we could do. No one complained about price. The single biggest problem we have, even til today, is not how much we cost - it's getting people to actually give away things that they think only they can do. It's quite literally a forever battle against the ego in all of us.
The best part is working with wonderful military spouses, who are some of the most honest, hard-working, dedicated, and kind people on the planet. Who know how to manage and wrangle chaos.
Once we let this go, everything changes. More time, less stress, more peace.
It wasn't all our decisions, any good business is really about the market. We had insane market winds at our back. By 2018, almost every local service had been brought online. Someone remotely could hire a babysitter, deliver groceries, clean your house, book all your reservations, flights, respond to email, hire an Uber, almost everything.
As almost all local services came online, remote assistants had in-person superpowers they could do from anywhere.
Then there’s luck. For us, weirdly, that was Covid. They say luck is when preparation meets opportunity. What Covid taught the world was what we already knew because we’d been working like this for a decade. Work is global, work is virtual, relationships and trust can be built online as well as offline.
It's a secret we knew, that most people didn't believe. This single sentence is what I look for in finding great opportunities. What's a secret I know that most people don't believe. Better yet, most people think is a joke. That's where the gold lies.
We couldn’t have predicted that, but I’d be lying if I said we didn’t benefit from it. Weirdly, it changed everyone’s view of work and we were lucky to already be operating how the world would now learn to work.
Something else I think about a lot: This company started as a side project for my VC-backed startup, Assist—and it’s outlived it and will probably be much bigger.
You never know how things will play out, keep building and solve your own problems I guess.
The best part of building this company has been watching Michelle grow as a leader and being obsessed with our mission.
Being a founder & CEO is one of the hardest things in the world. It’s lonely, everyone mocks you for the first few years while they have a job at a company their parents know the name of. Not to mention self doubt is screaming at you.
But nothing beats fighting through it and doing something you deeply believe in.
I deeply wanted to give people their time back, give employees the same perks as the execs, and quit wasting money on dumb office perks since half our company was remote — while Michelle wanted to help solve the military spouse unemployment crisis and create remote work that had purpose.
This was before anyone believed remote work was actually a real way to work. It’s not everyday when two deep beliefs align so well to create something truly magic. Forever grateful to all of our team, customers, and Michelle.
To close out, one thing we've done since the beginning is be open about everything. Michelle shared all of our financials in her latest post and it's cool to be able to share those here and help others to learn from it.
- Numbers as of September 2024:
- We now have over 400 assistants and 1000s of customers.
- We passed $41m in total revenue
- We have paid over $26m to military spouses and their families
- ARR: $13.5m (projected. Doing over $1m MRR is wild!)
- Net income $3.4m (projected) Growing over 50% YoY
- No investors, entirely bootstrapped, very profitable (33% gross profit margins)
But, as anyone in business knows, only the paranoid survive. Back to work. Kudos to Michelle and the entire team, couldn't have done it without each of you.
So much more to do. Over 300,000 military spouses to employ. Onward.
I want to say thanks to my assistant Caroline who truly makes my life better every single day. I don't actually know how I would function without her.
If you want to make your life better, get your time back, be more productive, and have a little more peace... Check out https://www.gosquaredaway.com/ or email michelle@gosquaredaway.com and say hi.