Ian Crosby is the co-founder and CEO of Bench, North America’s largest bookkeeping service. Recognizing that entrepreneurs go into business to pursue a passion, not to do administrative work, Ian saw the opportunity to improve lives for small business owners by making bookkeeping simple, effortless, and affordable.
Originally launched out of Techstars NYC in 2012, Bench has raised $53 million to date and is the fastest growing company in BC and the 4th fastest in Canada, according to the Deloitte Fast 50 list. Ian has received numerous awards for leadership and was recently named one of Canada’s Top 40-Under-40.
Again, I don’t see funerals is hard to see really there’s a lot of emotions there and there’s there to be experienced. But you know, there’s nothing wrong with them. Like we are human beings. We are born we live and we die and that’s just a fact reality for all of us. And you know where we’re going to trouble is when we pretend that. That’s not true that like what I’m doing now is going to exist forever is going to you know going to tell some Grand narrative what my life is. Other than that. I’m a human being with the finite lifespan and I’m really present to what I wanted to be doing with this time what I’m going to experience this moment and what it what is neat like, you know, I think I’m going to spend a lot more time in our society thinking about these questions because if you’re not profoundly related to like what is literally the thing that is happening right now how it like.
What is this thing of this a this phenomenon of Consciousness that I am right? It’s like I’m going to go pretend that I’m going to vomit on and and that like okay, here’s what I do I go have a career and I do some things there’s it’s like what’s it career? I don’t understand what that is is a made-up thing like, you know, like put yourself in a situation of. Examining someone’s life 2,000 years ago ancient Rome and like the stuff they would tell themselves. Oh, we’re going to make a you know an offering to Athena today and you’re like, well, that’s silly but I could get you know, they’re not really oh that’s not really reality. That’s what they used back then. Yeah, but that’s what we’re doing right now.
All of the time careers are us going to the temple of Athena and you know, people are gonna be like, why did people think that that was important right like what I mean? This is what do you want to don’t feel Limited in what you’re going to spend with your time. And like we have a lot of recurrent conversations with each other about this is the way the world is is the way your life is going to be and it’s just that it’s a conversation. Someone said it doesn’t make it true. Right and and so I just do a lot of exploration about what reality actually is because if you’re not actually related to what reality actually is, how can you change reality? You know, you’re just you’re operating on the level of. Narratives and stories that were telling each other and all that happens is the story changes but reality didn’t you know, and as an entrepreneur when I see that is as an opportunity for me to actually change the way that reality is not just the way that you’re talking about it like but why did you start this business, you know? There’s Justin why I started it and why I do it now and I think it’s probably the same for a lot of people write is I started it because idea for business. I never really run a business before and you know, I figured the only way I’m really going to learn is by jumping in with both feet, you know, and I saw this opportunity like I’ve been hired as a bookkeeper before when I was a student when I was a business student inside you stuck with me. You know, how am I your best option? You just hiring. You know, I’m 19 years old. I have no business experience and stuff has to get done is business critical for you. How am I your best option to place? You can go on the internet and like you can trust them, you know, I think my credit card in and perfect bookkeeping comes out the other side and there’s nothing you have to worry about. Like, how does it not exist? Everyone has this problem right?
How is everyone? Struggling trying to figure out how they’re going to do it and come off with a sort of one-off way. Like, you know, you think of Gmail and you’re like a to send and receive email I go to this website I sign up and I’ve got an email account and I’m not worrying about all the settings of the servers are all that kind of stuff because I don’t even mean extra how email works or to send an email and people just have that same experience with your business. They should just know how much money they’re making. You know or how much money they’re losing and as you know should be simple as opening up your phone and seeing oh, here’s my use my scorecard, right? And what did I not expect but I’m not seeing you know, what I did you differently right rather than even just oh God. Did I capture everything? You know? Oh, how am I even going to how do I know these numbers even right. Can I trust he’s like those are not fun questions to layer on top of I don’t know if I was doing well and I don’t know if the numbers of looking at tell me, you know, an accurate picture or not, you know, so that’s that’s really where it came from. I want people to feel like. They are master of their finances now that their finances are you know on top of that? You know what? I mean, right? Oh, I know what you mean finally managing my personal finances. Like I have auto pay for my SD g e– bill, you know, finally after all these years I know and now it’s my business. It’s like okay – coming in and I have the site thing on making money over there and Amazon and this and that. Can I use the have an accountant and I found them in the Yellow Pages and it was like really. I didn’t want to spend time with this guy. It was like it was like going to a dentist office and I’m supposed to bring like my my receipts and it was just you know, and they’re gonna tell you all the things you didn’t do right right. Have you been flossing? So Ben Chimes? I went to bench that Co and I I just look at appearance and field looks good.
Looks comfortable and it’s big. I mean I was Googling it and you guys are getting funded I think over 30 million dollar. I mean, it’s a it’s exciting right now for you, huh? Yeah. Yeah, I mean. we’re now like six years into it and. Yeah, it’s like we’re finally really hitting our stride and able to really get across like hey, this is what’s important in this can really make a big difference for you and you know sort of hitting a critical mass of entrepreneurs and Justice idea. You know, this is idea of you should look up someone in the Yellow Pages and that’s like that’s going to count is right versus we’ve got people who are going to help you. We’re service, right? We’ve got people here that are going to help you. He just looks and feels very different very different idea of what this could be. Right, like it’s reimagined for 2019. Like we’ve all got all this technology in front of us, right all this data on your business lives in Banks and lives in you know, you’re all the services you’re using and you know, what if someone really just were thoughtful about how can we use all that information and put it together in a way that’s right for you and you’re not worrying about it and just use it to give you the most power that they possibly can and use mobile. Use modern technology like having it on your phone and just having online in real-time and having you know, like chatting with the person’s of the were you the service is like feels like I message right it doesn’t feel like you know 1998. Yeah, like and it’s just feel natural right like like if you were to hire someone in your business and like how would you be chatting with that person? There’s you know, like. Just being real with each other and using modern technology or however you’re going to chat right and not kind of this like, oh, here’s what he has to be. Sorry. This is just you know, like we all put up we all know it’s bad, but we all put up with it and sorry got to get your taxes done. So it’s kind of going to feel we’re like nah, the human race can do a little better than that, you know in 2019. Yeah, right and in terms of that resonates with a lot of people. Do you feel you were thrown into this quickly? I mean a lot of people, you know, it’s up and down and they tread water and they try and they keep failing and they try and they blink of an eye there 68. And it’s like oh my gosh. I wish one thing would have worked and it seems like you’re young guy and things are working for you.
What do you contribute that to just a good need that filled a good a good solution or is it your management style is just my charismatic Rockstar personality. No, it’s I just. I learned a lot of important lessons. I went out and got some great mentors and learned, you know, what really makes a difference and what this thing could be and you know. What I learned that really works is if you want to build something that’s going to affect a lot of people as going to have a lot of employees cultures the most important tool your disposal. And that you know a lot of people they start their business and they get some people in there like. What’s this culture? Why are people this way? They shouldn’t be doing it this way, right? It’s like cultures that they happening to them right rather than what kind of culture you’re going to create their. We’re just going to be very opinionated about know this is the culture. I know you might have done it that way another place. But this is the Bench way and you might not be the best possible way. Maybe there’s a better way out there, but this is our way and and you know, if you’re not doing it is something right or wrong about it, but it isn’t that true and really. I think everyone do it that way. So we have you know our culture like when we started out like what I thought culture was was when we started out with me and my best friend from high school my best friend from college and culture meant that we like hanging out with you. Yeah, you’ve made it with our Social Circle, which I hope for maybe three or five or eight people that works. But then we have a lot of disagreements about how things were actually going to go here. Right? It turned out that you know our ability to entertain each other, you know at Friday night viewers was not actually the same thing is what’s going to make a difference for many people. It was wearing off. Yeah, and and so.
You know many years later and this is not like and then I realized it was like it was her personal journey and had lots of you know, upsetting things happen that I had to figure out how the heck did that happen and like why do people treat each other that way and. Put in a lot of personal development got mentors got coaching and put together a culture that’s defined by principles not by just default Behavior or what? I’m comfortable with right so we have five principles and I called the principles not values because it’s it’s like their tools that. We use they’re not right or wrong. So the first principle is default open, which is that everyone at bench has the right to see all event is information. As long as it’s not private employee information are Private Client information. Everything is open and everybody. There’s no like can I share this information? It’s like wait, you’re not allowed to not share it like I was a default not open already, right like and you know what? I. What I’ve seen before that before you had that was I would say hey, there’s no reason not to share this up. Hey guys, it’s all share this stuff. Right and some people just wouldn’t and they have lots of excuses for why they wouldn’t and some people would want to do it for like, oh, well, I control this information then yeah, you know, I get an advantage and other people would just feel like well, I’m just not comfortable with scary sharing stuff. So I’m just not going to you or I will someday, you know, I will share it when it’s perfect and. Right like you go off in a corner and you can come back once everything’s perfect. And then, you know people set up set themselves up for really very stressful time because they’re creating like an external picture that’s very different from what’s actually going on inside, you know, and whenever when we’re just when that never happens because everyone who sees what’s going on right as it’s going on so like every day like so I’ll give you an example. Every year basis bookkeeping great every month benches bookkeeping you use been yours. We actually got off the bench for ours and I’m like I need to get back to it because like we begin this thing where they’re like, oh we’re going to use any birth to baby Buddy’s enterprise software and right notice all participating more and I’m like.
This isn’t better. They just convinced us that you know, you’re big so you have to do the thing. Like we could build a thing. That’s actually like there’s so much stuff. We lost doing off of bench. I want to go back to it. Anyway, I don’t want to see the vendor because they’ll probably sue me for defamation of knowledge. Yeah, but. You know, we publish our internal financial statements to everyone in the company the same time like I don’t get our p&l before our bookkeepers do like everyone gets to find fish station same time as it’s like it’s not like I’m going to get the financial statements and we were like, oh, I gotta shake the reality of how people are going to perceive this. Right? Right? No. Everyone’s a grown-up here. Here’s what happened. Hey, this was less than I expected. This is one respected. Yeah, how do we figure that out together? I don’t have to be the one who like shapes reality for you. Right – we’re all just figuring out what it means and what reality is and then people can take actions. You know, they don’t depend on me Bill don’t have to go through me to understand what’s going on and get an access to sort of what would be a good action for them to take right? So we set these principles we have five of them and it just enables us to really. Just of does the team and share this Vision that we’re going to bring a million people Master their finances and that’s what it’s really about. Right? It’s not like for us the vision isn’t okay. Here’s a nice story and the culture is we all say that we agree with his. Right, but we don’t really we don’t really believe in it, but you’re supposed to say right and that’s how I kind of when I worked at companies before that’s how I interpreted division is like what’s a nice marketing line that we should all kind of pay lip service to versus like no actually K. Let’s get real for a second. Okay. What is the life that we’re living right now? Yeah, we want to do with that. Like we’re on a rock hurtling through space at 67,000 miles per hour. That’s what’s actually real. Right, that’s more real than anything else that we’re talking about right now. My name is Ian. And your name is Phil like only because we all agreed it was going to be that way.
The universe has no opinion on that map. Right when we find ourselves in the actual Universe the reality of our circumstances. Like let’s get right into that. And then how do we actually want to change things? How do we actually want to make that look different with our time? And that’s what we that’s what we spend. Our time on is if people are having real feelings those feelings actually exist of frustration and powerlessness and like on an MRI. You can see that emotion like, all right. Mrs. Pulcher. We kind of like we pretend like emotions are real like they’re kind of made up or something and that these are like strategy is real or something. And our business is a real and like no we got a backwards man businesses are not real. We just made them up. They’re kind of like Stories We Tell ourselves to make sense of her own behavior. But like there’s no example of it in the physical Universe you can’t like. Find physically where is the business right? If you go looking for it, you’ll find people you’ll see words on screens words on screens are real the screens are real, you know, like and the people are real like I can see those physically and emotions are real emotions are actually there in our brains. They’re like reactions and Electro chemical phenomenon that exists in the physical Universe businesses are not yeah, so we’re like, I want to change things. It’s I just want to change the way that people. He’ll and I want people to feel a lot more possibly but what’s possible for them in their life, you know, and then we’re going to make up this business thing and it’s a game with a purpose of coordinating all our activities to make that reality happen in you know, when we talk about it that way it gives people a real power because it’s like, oh, there’s no like right or wrong way to do this business thing that business thing is like we should create whatever is actually. Going to make a difference for people right there making a difference for people is is the part we care about not the like in you know, like has to have a certain CEO Persona or say the words the right way and that’s a right venue business that if he doesn’t pitch it and that’s a bad way to do business or Ripley totally arbitrary, right? It’s like whatever works and what we’re committed to is like it works. It actually got the thing done and and and life is actually better for people so it. It’s just very free. God you’re an awesome guy. I could sit here listening what number one I love the background that you have in the back Industrial. I love how passionate you are man. Thank you.
Yes, there is. No stopping you right now. I mean you built yourself a great company and I am excited to use it to help me. If you can start a business by first saying I am going to hire people that Inspire other people around them and I am going to fill a need. To help people and help businesses. You’re done investors like that your shareholders like that. Yeah customers like that. You’re living a dream right now, but it’s not always easy. So when it’s down here in the Gully in the Deep, how do you it’s not always easy or not always smiling right now. How do you how do you deal with it? Yeah, so the first thing is realizing that and you know, I had this Moment by the way, so I was if I have a walk-in closet in a little walk-in closets, you know, start looking massive walk-in closets like, you know to shoulder likes right now 200 pairs of shooting. Yeah exactly. Now, I felt like ten pairs of pants cumulative. So it’s not like a massive, you know long pause or anything but a my closet I had this moment where I’m like, I don’t know if I could do this like, I don’t know if this is gonna work like oh God like what’s. I’m like Oh my calendar. Like how are you do all these things and like this is so overwhelming and I just trained myself.
Like I’ve done a lot of coaching a lot of personal development that in that moment. I recognize that what’s happening doesn’t actually exist outside in the real world is it really just is in my head like there’s nothing about this isn’t going to work. That exists in my closet or in my office or like, you know in another person or any were physically is just this is this is just a conversation. I’m having with myself. That’s all that’s actually happening and like recognizing that and then going civil way. Do I want to be right now? You know what? I don’t want my life to go today, you know, and then Anna ground myself in a few things that I know to be true. I know to be true there is some permutation of reality where this works. You know and maybe I haven’t created that for myself today. Maybe I didn’t do not make maybe I made a decision that is actually not compatible with this thing working. Okay, cool. So maybe I should just find that thing and identify and fix it right like and find a permutation of reality where it’s going to work. Because there’s some permutation where it’s going to work with some permutation where people get their finances done and they feel powerful right? Like I can very visually see like yeah, that’s that’s not like how would you how would you do that? It’s like how we’re doing that for 7,000 people already right and and you know and like rapidly growing and people making the decisions and there’s some places where oh, yeah, there’s things that we’re not in in defying and they’re not really working and how about I just create a definition. Workability and then I just identify what’s working. And what’s not working.
Right? And you know, it wasn’t working that moment was. and you know, I can see what your triggers me is. I had not. Built up my calendar to work that day like I could see that there wasn’t like what I would say my counter lacks Integrity. It was like it wasn’t going to work. It wasn’t workability. I did not have book enough time. There’s any any prepare for and I booked over my preparation time and I was like, oh, I’m just going to. Go and like I could feel that in the back of my head. I knew that there were some things they that we’re going to work and that there’s gonna be stressful and that because I had unresolved it kind of built up and built up and built up into a I can’t do this what’s going to happen. Right? And so I walked out of that closet I said, you know, okay, here’s what you do. I’m going to make my day work today. And I just did that I canceled some meetings every race my schedule. I’m not like my skate. My calendars not happening to me. I don’t even have to get into bed in the morning. If I don’t want to you know, like I could just stay in bed. All day is how but I regain like give up this narrative that like something’s happening to me or that I have to do something and just give back to what do you want to create the universe today? That’s really all that matters is the only question that really matters, right if I’m having some other conversation nothing wrong with it. It’s just not the conversation that I want to choose for myself. And just ground myself in that in like. getting getting something solid right that I know to be true that I wanted I want to act from and it took a long training right early earlier years of bench. There was a lot of you know, I go through like a month of. I don’t do this anymore. I can’t do this. This sucks is horrible, like running a business is hard. It’s hard so hard so I wouldn’t wait. Hold on a second. Wait, what’s hard about it like understand there’s things that need to happen. And then if I don’t make the decisions that work than business won’t work and maybe you’ll run out of money. But what’s hard I’m like look for the hardware is the heart is it like having you know, sometimes I have to have a conversation with someone. Is it going to work out? We’re not gonna be able to work together anymore because it just doesn’t work. Is that hard? What’s hard about it that you know, they’re going to have emotions. Yes, you have emotions, you know, there should be a lot of emotions in my life. This is actually, you know, I don’t enjoy having that conversation. It’s not hard like I know how to have that conversation. I know the words that are going to walk in and you know, we’re going to have. You know some emotions are going to happen and I walk out and then recruit a lot of workability in my business and I actually need to have that conversation over Frank has to work right? It’s not hard.
It’s like what’s hard is like this table? That might be my laptop sitting on that’s hard right? I can feel that funeral is hard. Experian death and heartache and running a business and I have people that I myself will complain a lot that it’s so hard not getting a paycheck or consistent one, right?
I’m an entrepreneur and so difficult blah blah blah. This is easy. This is fun. We got to make it fun. You have to find your passion and I’m like one praise. My mom just texted me this morning. Make it a great day. Because you have to you have to physically this know like just do it. Make it a great day. Just make it no matter what no matter the downs and the lows and the travesty. Oh boy. You just have to have that mindset. I again, I don’t keep you know, this is hard to see really there’s a lot of emotions there and there’s there to be experienced. But you know, there’s nothing wrong with them. Like we are human beings we are born we live and we die and that’s just a fact reality for all of us. And you know, what we’re going to trouble is when we pretend that that’s not true that like what I’m doing now is going to exist forever is going to you know going to tell some Grand narrative what my life is. Other than that, I’m a human being with the finite lifespan and I’m really present too. What I wanted to be doing with this time what I’m going to experience this moment and what it what is neat like, you know, I think I’m going to spend a lot more time in our society thinking about these questions because if you’re not profoundly related to like what is literally the thing that is happening right now how it like what is this? Speaking of this is this phenomenon of Consciousness that I am right? It’s like I’m going to go pretend that I’m going to vomit on and and that like, okay, here’s what I do I go have a career and I do some things there’s it’s like what’s it career? I don’t understand what that is is a made-up thing like, you know, like put yourself in a situation of. Examining someone’s life 2,000 years ago major Crowe and like the stuff they would tell themselves. Oh, we’re going to make a you know an offering to Athena today and you’re like, well, that’s silly but I could get you know, they’re not really oh that’s not really reality. But that’s what they used back then. Yeah, but that’s what we’re doing right now. All of the time careers are us going to the temple of Athena and you know, people are gonna be like, why did people think that that was important right like what I mean? 21 I don’t feel Limited in what you’re going to spend with your time in like we have a lot of recurring conversations with each other about this is the way the world is the way your life’s going to be and it’s just that it’s a conversation. Someone said it doesn’t make it true. Right and and so I just do a lot of exploration about what reality actually is because if you’re not actually related to what reality actually is, how can you change reality?
You know, you’re just you’re operating on the level of. Narratives and stories that were telling each other and all that happens is the story changes but reality didn’t you know, and as an entrepreneur what I see that is as an opportunity for me to actually change the way that reality is not just the way you are talking about it.
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