Startup Sitdown – Ian Crosby (10Sheet)

Ian Crosby is the CEO of fellow TechStars company 10Sheet. His startup is completely revolutionizing the book keeping experience, especially for small businesses, by moving it online and onto a beautifully designed interface. Ian and his co-founders Adam, Pavel and Jordan just moved from Canada to NY for TechStars (Pavel moved from Siberia). They are a magnetic team and the pride of Canada.

What is 10Sheet?

The idea is that right now, a lot of small business just have a bookkeeper that they send all of their book keeping stuff to – receipts, bank statements, invoices – then the bookkeeper sends back financial statements, so your income statement or balance sheet. We want to provide the same experience but do it in a much more automated and streamlined way. We do it in a much more pleasant way and we’re able to do it way cheaper – like 10 – 20 percent of the cost because we’ve got a lot of automation and smart things we’ve done with the process. So again, the user gets a way better experience at a fraction of the cost.

Where did the idea come from?

Well when I was at University, I was paying my way through school as a bookkeeper, and I realized that it was just a horribly inefficient process, and something that a lot of small businesses just don’t want to spend time on. Its just really frustrating and they need a solution. After getting exposure to that problem, its just something I really wanted to solve for small businesses. Because If I was ever going to an entrepreneur, that’s one thing I didn’t want to deal with, so why not just wipe that off the face of the planet. Then the next time I start a company thats one thing checked off the list that I don’t have to worry about.

What is your personal history with entrepreneurship?

I’ve always done little things on the side. Even just being a freelancer, hiring myself as a tutor. I had one traditional job, which was working at my dad’s law firm, which I just hated, and realized that I have issues working for somebody else. I was in the army for a few years, and I learned a lot. I felt like if I was going to work for somebody else, I better be learning a ton. Otherwise it’s just not worth my time for a paycheck. I worked for Bain & Company much for the same reason: I wanted to be an entrepreneur, but had no idea how do to it, so I just had to get the business world, figure out how it works, and then I could strike out on my own. I needed to learn how to scale the things I had done on the side and turn them into a business.

I learned a lot about business at Bain. If somebody’s only interaction with larger businesses is walking to the corner store and seeing stuff on the shelf, it doesn’t occur to them how inefficient and screwed up business processes are. When you actually work with companies, you realize that there are a lot of messed up things that could be fixed.

What are the biggest challenges you’re facing?

Our biggest challenges are figuring out user experience. Bookkeeping is something people really don’t want to deal with, but at the same time they really care about certain parts of it, like accuracy and security. They don’t care about how it gets done, but need it to be perfect, so we need to strike a good balance in terms of how much we communicate to them.

What are some big differences with building a company in Canada?

Well we get a ton of government help. The government realizes that the U.S. is way ahead in terms of startups and they are just throwing tons of financial incentives at startups. We had the option to take $500k in funding. We just did a little presentation for the government and they were like “yup, that’s great, here’s a convertible note if you want it.” They have actually set it up pretty intelligently where they have a board of VC’s deciding who gets the money, but its all government funded. There is also the program where if you are doing original stuff, stuff that you couldn’t just buy off the shelf, the government will fund a big portion of your developer salaries. It’s really awesome because it totally de-risks all that R & D.

What is your relationship with your co-founders like?

We are super tight actually, we are all living together in New York right now, which we probably couldn’t do if we were close friends. I met Jordan in University and we just instantly clicked. We would talk about startups all the time. We were the two guys that didn’t just look at the paths set out for us and just accept investment banking, accounting etc. Adam, our creative director, and I have known each other for like 20 years. We had fallen out of touch, and then we got back together and it turned out that he had designed the “To-do” app that I used.

What is the best part of running a startup?

The best part is also the worst part. It’s the fact that there is unlimited freedom. There is unlimited freedom to screw up, but also unlimited freedom to succeed. Sometimes there is a ton of pressure because of that freedom – you go to bed at night and you can’t stop thinking about the five things you’re worried about. At the same time, you sit back and say “wow, I got this far? it’s so awesome I’m even thinking about these problems.” As you get higher and higher stakes, and you get funded, there is a lot more on the line than just my time, like somebody else’s money. If this company goes down now, I’m disappointing a lot more people than just myself.


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