“Team Mentality” — with Ian Crosby, Co-Founder & CEO Bench

Today, we’re speaking with Ian Crosby, Co-Founder & CEO of Bench Accounting. We discuss his time in the army, his most valuable lessons, and how Bench is revolutionizing the bookkeeping industry.

Today’s episode of Journey Map is brought to you by MindManager.

Journey Map listeners know that with the right map you can take your career anywhere you set your mind to. MindManager work management software puts your ideas, plans and projects on the path to success by transforming them into dynamic digital maps, charts, diagrams and more. Mind Managers flexible visual format makes it easy to capture, organize, understand and evolve critical business information and with powerful collaboration sharing features it’s the perfect tool for keeping remote teams aligned, on track and headed in the right direction.You can take a free thirty day no commitment trial today by visiting www.mindmanager.com/journeymap.

Welcome to Journey Map, the audio experience that deconstructs the career paths taken by some of the world’s most interesting people. Today’s guest graduated from the University of British Columbia in 2008 with a Bachelor of Commerce in Finance and Economics. He was an Infantry Soldier Reservist with the Seaforth Highlanders Regiment with the Canadian Armed Forces. He briefly worked as a Finance Supervisor at Threewave Software, before leaving to work as an Associate Consultant at Bain & Company. In 2012 he Co-Founded fintech company Bench, which would help land him on the Forbes 30 under 30 list. For those of you who don’t know Bench is the largest bookkeeping service in America for small businesses and entrepreneurs. They go beyond traditional bookkeeping as they strive to help entrepreneurs understand what they want to do and where they want to go.

Today’s episode of Journey Map is brought to you by MindManager. Journey Map listeners know that with the right map you can take your career anywhere you set your mind to. MindManager work management software puts your ideas, plans and projects on the path to success by transforming them into dynamic digital maps, charts, diagrams and more. Mind Managers flexible visual format makes it easy to capture, organize, understand and evolve critical business information and with powerful collaboration sharing features it’s the perfect tool for keeping remote teams aligned, on track and headed in the right direction.You can take a free thirty day no commitment trial today by visiting www.mindmanager.com/journeymap.

DH: Today’s guest is Ian Crosby, Co-Founder and CEO of Bench. Ian Welcome to Journey Map!

IC: Thanks for having me!

DH: So I actually don’t know where to start on this one, but I think a good place would be your time spent in the Canadian armed forces. Is that something that you were involved in from a young age, like did you do Cadets? What’s the story in how you got involved there?

IC: No not at all. When I was in twelfth grade I had a substitute math teacher and he brought in this army recruiting pamphlet or something and he was an ex-military guy. I have no idea why a substitute math teacher would bring an army recruiting pamphlet into a classroom, but he said “Hey I have an extra one of these, anybody want it?” and you know I’m just curious but I said okay I’ll take it. I looked through it and that’s when the wheels started turning in my head sort of but we’ll start turning my head. I’m 16 and I want to have really different experiences, I want every job that I ever have to teach me something. I was a very ambitious teenager, people would say I was pretty weird but I had a good time. I was thinking about how I can set up my life on the maximum possible trajectory? So I’m reading through just what it’s like and I was like huh well I think I would learn a lot more in the army then flipping burgers, so I think I’ll apply. I tell my parents that night, and my mom is mortified like “My baby can’t go into the army, what’s going to happen to him?” and you know my dad sort of calmed her down and explained to her that this was reserves they’re not sending him overseas or anything. For context this was during the war in Afghanistan and Iraq, that I wasn’t actually aware of but my mom was making immediate connections with. But for me it seemed like a great experience so I applied, and I got rejected because on my form I disclosed I had a peanut allergy. They apparently don’t want people with peanut allergies in the army. So I figured out to appeal the denial decision and you know I got a letter back saying well you know if you’re willing to subject yourself to the peanut eating test then we’ll be willing to let you in the army. So I call up the allergy doctor, buy some peanut butter, and go down to the allergy doctor where he watches me eat the peanut butter on a cracker. This is my very intense army recruitment story right? I must have felt sick for an entire day like I ate so much peanut butter, but I passed the test and they let me in. I just had to prove I wouldn’t die if I ate peanuts because you know the enemy has super peanut weapons or something. So yeah I passed that and appealed it and got in. That is my entire story you know once I put my mind to something it was like “Are you kidding me you’re going to let me join the army because of peanut allergy?” I will eat peanuts until you let me know the army. That’s really the entirety of the story of how I got into the army.

DH: Well two things on that, first of all this is the saddest I spend a lot of time painting a picture of myself to show how douchey I am but I spend a lot of time researching like military navy seals training and like all this kind of stuff and so this is the saddest military recruitment story I’ve heard of. Secondly I still have asthma, but I’m going to date myself a bit but when I was a kid it was an era where if you’re asthmatic you should not do anything remotely physical because it will kill you. I didn’t play winter sports, and would have to stay inside at recess if it was under -10 C, which I live in Ottawa Canada like that happens in April. So that definitely sucked, but I made really good friends with the school receptionist which has served me really well in life. So funny enough I would have loved to pursue a similar early career path but was basically told you know your asthma is going to hold you back from doing these things. Now of course many years later the irony is I have two young kids who have asthma and they’re like they need to be put into winter sports to help them overcome this.

IC: Of course.

DH: Anyway I digress. So I feel for your story and that’s pretty amazing I wanted to start there for a reason. Okay so what are some of the things that you learned in the military beyond the obvious stuff like I’m sure that you’re pretty good about being on time, working hard and all that kind of stuff. But beyond the obvious stuff, what are some things that you learned in the military that you can help attribute to some of the pretty wild success that you’ve had since then?

IC: Yeah I think the one thing I really took with me was the concept of a team, which is really what boot camp is meant to drill in. In the beginning we were all just trying individually, but you know you’re in a platoon of 40 people divided into 4 sections of 10 people and you know you’re really tight with people in your section. At the beginning we’re these 10 guys in the section and we’re all really focused on ourselves and shining my boots and being ready for my inspection. They would punish us anytime anyone in the section messed up. In the beginning people would get pissed off at each other like “How did you screw that up and get us all in trouble?” and this is happening five or ten times a day over the smallest little things. In the morning you have to lay out your toiletries on a towel exactly 3 centimeters apart and everyone has to do it exactly the same way, if anyone is off by a millimeter like they bring in a ruler, but if anyone was off by a millimeter the entire section has to do pushups or some kind of you know punishment. After about a week we start realizing, you know it really doesn’t matter who screws up, or if they’re dumb, or if it’s their fault. This entire concept of fault disappeared and it was just how do we have the team succeed so we don’t have to do push ups? Then by the end of the first month there was no thought about whether this guy screwed up what an idiot or anything like that, it was if you see your buddy struggling you just go help him. Where does the team need to go? What’s happening? Just being aware and you know getting people there. We were self organizing, we were going to have one person who measures all the stuff so we have standardization across toiletries, and we organized ourselves that way. That was kind of the whole point of the training was “Are you guys going to self organize in order to succeed?Or are you guys going to sit there and complain about the one person who failed this time?” it’s going to be someone if you don’t is going to be someone if you don’t coordinate right. Realizing that that’s a team phenomenon it’s not an individual phenomenon. I have this one memory close to the end of boot camp where they were running some exercises and a buddy drops his helmet and doesn’t notice, and the guy right behind him just picks it up off the ground and attaches it to the back of his bag without saying anything it’s just like automatic no one says anything, it’s just like yeah of course you see someone drop their helmet you pick it up and help them out and you get the squad where it needs to go. Whereas before that at the beginning it would be “Haha you dropped your helmet” or “Hey I picked up your helmet aren’t you going to thank me for reattaching it?” or something like that.

DH: Yeah you know it’s so funny right before you said that last piece that’s actually what I was going to comment on, that it’s one thing to see someone drop the helmet and not pick the it up which is one kind of offence but to pick it up reattach it only to get the acknowledgement of doing it. As someone who is pretty like that I’ll admit I think that’s a worse offense gthan just not picking it up in the first place.

IC: Think about the psychology with that. Inorder to do that one’s attention would have to be on oneself. If I were to pick something up just to get appreciation my attention is just on what can I do to get appreciation and your attention is not on what we are trying to accomplish here, what is the purpose of this team? But when everyone’s attention is on what’s the purpose of this team, people aren’t thinking about themselves. You almost have an out of body experience where you’re not you, you’re the team. I’m not Ian, I’m a member of the team and just operating that way. No need for self acknowledgement, the focus is on the mission. I really took that with me. This is just a group of 17 and 18 year olds running around the forest with guns, but it was a really formative experience in my life though and I’m really glad I did it.

DH: I want to ask this question because it’s really funny the number of people who we interview on Journey Map whose career timeline looks similar to yours in respect to they worked as a consultant and I don’t mean like on their own independent consultant I mean like they worked as a consultant at like a big name consulting firm in your case Bain &Co, and then immediately after their career timeline goes into startup.My inference is that when you are working as a consultant you’re exposed to so many different companies business models, markets, economic environments etc. that you have a wider scope to decide what kind of company you would create if you were to do that. Do you feel like that is what happened in the creation of Bench or is it a different story?

IC: No not really, I mean I didn’t get the idea for my company from any of the clients that I’d seen. The people who I work with on a day-to-day basis are clients who are CEOs or Senior Executives and realizing these are just people? and very often they’re not special people they’re normal people. Then I was like I can totally do this, this person doesn’t have anything I don’t have. So I think that’s part of it and then this whole idea of a career ladder kind of falls away as just a fiction, it’s like I could spend fifty years climbing this ladder and be where this person is, but I don’t like this person’s life this person isn’t happy. Why the h*** would I want to do that you know? So just jumping into whatever I wanted to do I mean I knew at about age 10 that I wanted to start a business, and I realized doing anything more at this point is not going to teach me more about how to start a business, so I’m better off to just jump in the deep end and see what happens. So that’s what I did.

DH: Yeah it’s funny in 2015 our company came pretty close to bankruptcy, I’m trying to say that publicly. I remember a partner at the firm after we made it through saying “Congratulations boys you’ve just given yourself a very expensive MBA”.

IC: Accurate

DH: I was like yeah it took about as long as completing an MBA to get out of that situation and cost about 30x more, but yeah sure sounds good. Okay so switching gears to Bench, you guys had some phenomenal success I think I had noted that one year I forget which year but you were the fastest growing company in the province of British Columbia, and the fourth fastest growing company in Canada in terms of Deloitte’s Fastest Growing Companies List. What has the journey been like from 2012 to today? I’ve been in business long enough to know that those awards and designations come with an inverted reality which is much less glamorous and much more terrifying. I’d love to hear your take on the story.

IC: What would you most like to hear?

DH: While you were building Bench can you name the moment you really realized that you had made it or that you were on the right path? Can you also name a time where you really felt like this is the end?

IC: I remember the point we crossed a million dollars in revenue and looking at our finance statements and going “Oh we made $84,000 in revenue last month” and that was like four to five months after launching. Before launch I was thinking if we could just get to a million in revenue this will be a real business and I’ll feel so much better because I still didn’t know if this thing was going to be successful, I didn’t know if I was a real entrepreneur or if I was just faking it like what am I doing? But once I get to a million in revenue I’ll know this is real and once I get to a million in revenue and I remember thinking this feels worse than not having revenue. Like now I have a burn rate, you know I have employees, and now there’s something at stake right? Whereas I feeled before I’d think oh that was a nice little experiment I learned a lot, but now if I fail I’m letting down thirty people and it just seemed like there were many more problems than wins. The stress let me put it this way, I just didn’t know how to deal with the feelings I was having. I had a lot of dread, and I didn’t know how to not have dread. What actions will cause me to not dread anymore? Is it more revenue? Like what the heck do I have to do to not have this fear? There were multiple points where I’d look at the business model and we were making 20% margins and we had all these fixed costs and I was like how are we ever going to make this work? It wasn’t like we were going out of business tomorrow but it just seemed like half the time I was putting one foot in front of the other but when I looked up all I saw was a dead end. It was like I have this theory that if we get our margins up to 60 % and that’s where we have our margins about now. But no ones ever done it before in bookkeeping, no one’s ever automated before. A lot of people have talked about automating but it doesn’t actually lead to cost reduction because you simplify one part of the process and you make the other part of the process more complex, so it’s just like playing whack a mole. There’s just a lot of dread and feeling like there was a dead end probably until two years ago, so the first six years. That was also when I was getting all the awards, which felt really weird I was like “Thank you I’ve created a very effective money losing organization”.

DH: Yeah, that’s why I was asking the question in 2013 our company was named the second fastest growing company in Ottawa behind only Shopify. We were the only company on the top 10 that had no external funding, and I remember feeling this odd mix of success but also knowing it was the greatest possible imposter syndrome that could exist. Because nearly two years later we almost went bankrupt because no services company should be the second fastest growing anything ever, especially in the land of tech companies. So if you were to rate your emotional state on a scale of 1–10 today when it comes to the business, you said it was only two years ago you were trying to get out of this place if dread. If you were to rate your emotional state on a scale of 1–10 today where is that at? Obviously it’s a unique time in the world with everything going on as well, but that aside where are you at today?

IC: I’d say a seven. It’s disorienting to suddenly find myself in this world, I mean all of us finding ourselves in this world. Everything has changed so fast, but I feel like I have agency over my life and that we have options. The company’s not just trying to survive now, we’re envisioning what can we build that would be great? Let’s go build that thing because we have a solid and stable business and I feel like I’ve really found a level of comfort and leadership in how to do it. The other thing that happened early on was that it was a very manually intensive process so we hired a lot of people really fast. So very quickly I found myself as the CEO of a 200 person company at age 26 and not really knowing how to relate to people, how to lead people, and what people needed. Suddenly people are writing Glassdoor reviews about how I’m a monster and the worst person ever, I’m like what? I like you, what is happening? Now I feel like I’ve been able to create that sense of team at Bench now. In general I would say I feel pretty good and that allows us to be there for other people who are really struggling. One thing we did at Bench when we saw this all happening we realized let’s be the best resource for small businesses to navigate this, and spun up a bunch of content around paycheque protection programs, EIDL, all the programs that all these business owners need and what they can do to stay afloat. Now if you google paycheque protection program we’re the number one hit on google. Our blog traffic has gone up 10x in the last month, we’re connecting small businesses both our clients and businesses that aren’t our clients with banks to actually get the loans, because it’s so hard and actually navigate people in the right direction and not charging for it just doing it for free. Because we know in the long run having people’s backs is really the best business model so it feels good, it feels solid, and it allows us to be available for other people who need it.

DH: Well thank you for all that you’re doing for small business, I’m assuming around the world at this point. On that note we’re both out of time and I hear the screams of a child who probably wants some attention which is the new normal that we are all living in. So thank you so much for taking the time to join us today. I really enjoyed the conversation, and I hope we can do this again in a few years and see where the journey has led to.

IC: Absolutely great to connect!