10 Things You Didn’t Know About… Bench Accounting CEO Ian Crosby

Like, what makes the Bench Accounting co-founder and CEO laugh.

Credit: Adam Blasberg

Though he was a freshman at the Sauder School of Business at the tender age of 16, it hasnt always been smooth sailing for Ian Crosby. 

Take the first quarter of this year, when the Bench Accounting co-founder and CEO realized that something had to change. 

We missed our sales numbers by 40 percent and werent able to fundraise. So we had a double cash problem—not bringing in as much revenue as we thought, and no way to raise money from investors, says Crosby from his downtown Vancouver office. 

The solution came out of a management offsite on April 2, where Crosby and the rest of the online bookkeeping services executive team embarked on a new plan. Two weeks later, Crosby let go of 18 people in the hopes of redesigning the company from scratch on the revenue side.

It was a low point for Bench, which Crosby started in 2008. But it didnt last long. The plan seems to have worked: Bench is currently looking for about 200 staffers, including 150 bookkeepers. 

If youre job hunting, you might want to brush up on what the man behind the company is really like. Heres a handy list. 

Where did you go on your last vacation?

We spend a lot of time in Whistler. Our six-year-old daughter is a fearless skier, and we love seeing her get better every year. She’s already giving skiing advice to her dad, who is “too slow!” I still outski my two-year-old son, but I imagine that won’t last too much longer.

What’s your favourite spot in B.C.?

Tough question, there’s so much to choose from! We love Whistler, the Sunshine Coast, wine country, and of course Vancouver and everything it has to offer. We moved our family back here from NYC when Bench started taking off and have never regretted it.

What’s your most memorable recent podcast, film or book?

I’m going to cheat and choose a TV series. The Expanse is phenomenal. I love pulpy sci-fi, and the show delivers. It was on Syfy for three seasons and cancelled, but Amazon Prime Video bought the rights and is producing another two seasons, which makes me very happy.

Also, nothing makes me laugh like Rick and Morty.

Favourite restaurant?

In Vancouver, I really like AnnaLena. It’s on First Ave and that’s our—my wife and I’s—regular date night spot. Super delicious. A little fancy but not too fancy. Leaves us a little bit poorer but not too much poorer. And it’s in Kits, right close to where we live, so that’s perfect for us. When we leave the house for date night, there’s a timer to when the babysitter leaves, so proximity is paramount! 

What’s your morning routine?

First thing I do is look at my calendar to make sure I don’t have an early call with someone on the East Coast! I make an espresso with my espresso maker, scarf some food and get my butt out to work for 9. Unless I have an 8 a.m. call, in which case I’ll be on my patio with my headset on—it’s the one place that’s quiet at 8 a.m. in a house full of kids.


I have two—one is extreme fitness. Whether it’s martial arts or interval training, I really like intense exercise. I really try to push myself until I want to throw up and then I know I’ve had a good workout.

And on the other side, I really like video games. Very specifically, I really like strategy video games which are very difficult and make me maybe want to throw up too! You might see a theme of intensity in my life. You know, I always have a compulsion to turn things up to 11, for better or worse!

Favourite quote?

If it disagrees with experiment, it’s wrong. In that simple statement is the key to science. It doesn’t make any difference how beautiful your guess is, it doesn’t make any difference how smart you are, who made the guess, or what his name is. If it disagrees with experiment, it’s wrong. That’s all there is to it.” Richard Feynman

It’s how I think of our “Experiment Together” principle here at Bench. 

Best/worst advice ever received?

Best advice ever received? Give it dead-simple instant utility. That was from a TechStars mentor who was a consultant at IDEO. It inspired many of our early design decisions.

Worst advice was “there’s no way this thing is worth $200,000, you should absolutely take that acquisition offer.” They shouldn’t feel too bad, though; it was meant honestly.

Your worst job ever?

I don’t know—I have zero complaints. You know, there were jobs that I hated. They weren’t the worst job. They were just great learning experiences at what I don’t want to do. I’d say working in construction with my brother, I learned that I’ve got two left hands. It’s not the construction job that’s the worst—it’s me that’s the worst at construction, ha!

If you could be an animal what would it be?

There are a couple of good options. Like, there’s jellyfish that can live for thousands of years. I’d love to be able to just observe the human race for thousands of years from an outside perspective.

The downside of being a jellyfish is you have no central nervous system. You can’t really appreciate the observation—nor do you have eyes, haha!

But if I had to pick, I would probably pick the elephant. An elephant because they are highly intelligent animals with complex social structures, lots of empathy, they live rich lives, and they’re not carnivorous. So they don’t cause hurt to other animals but they’re also too big to mess with!