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Great questions, let’s take them one by one:

1. What was your background growing up? Were you always entrepreneurial? Schooling/work experience, how did they play a factor in where your career went and what you decided to do?

A) My mom once gave me a book on starting your own business way back in high school. At the time, I had no idea why she gave it to me and I stowed it away on a shelf only to be pulled out years later. She saw my entrepreneurial nature before anyone else did—including me. It was that inclination I suppose that took me to Business School’s but I left university in my fourth year to carve out my own path and take a more hands-on-approach to learning.

B) When we started FreshBooks I sought to find a network of people that could advise me on running and growing the business. We were a small team in the early days and we needed support and guidance along the way. I am forever indebted to our advisors and they have become our biggest champions and challengers along the way, their support and encouragement has helped us to do things differently, challenging convention, and ultimately lead change within our industry.

2 What did you spend the majority of your time doing in the early days with a small team? Interfacing with users, building out the product, recruiting, marketing, etc?

Talking to our customers is like breathing to us. It was certainly important in developing our service, branding the company, and understanding how we could most provide the most value. Today, the same rings true, though of course my purview has expanded. Today I focus on the three Ps. People, Product and Promotion, and am grateful to work alongside experts in these areas and everything else.

3 What, if anything, from your younger days prepared you to build your vision and run a company?

I’d love to tell you that I had the vision from day one of what FreshBooks could be. The truth is, I didn’t. What I did have was a gut instinct of what was right for me. I knew the kind of people I wanted to work with every day. I knew what kind of service we wanted to provide to our customers. Ten years later, these instincts have served me well and keeps us on a well-defined path with few distractions.

— Mike

This wasn’t my first company – before FreshBooks, I was running a web design agency and making about $200K/year. When I wrote the first version of FreshBooks, it was originally designed as an in-house tool. Soon after, we realized others could benefit from it, so we used the money from the design company to fund the project, even working out of my parents’ basement for the first 3 years to keep things going. Some might call it insanity, but to us it made sense.

Our agency had an expertise in Internet Marketing, so we started advertising online to get our fist users. There was no big launch, not even a beta – FreshBooks really grew organically out of our dedication to the idea that we could help a grossly underserved constituency we knew well – small business owners.

How we built our service – using language that made sense to small business owners who let’s face it are NOT accountants –with the value it brought of saving time, money and getting paid faster, was a powerful combination. We coupled this with personal customer service. Everyone worked the phones in the early days – real people connecting with our customers. It’s something that we still do today. All combined, our customers loved the experience and it was word of mouth that got us our first 100 customers.

Awesome, thanks! And good luck!

1) What was your background growing up? Were you always entrepreneurial? Schooling/Work experience, how did they play a factor in where your career went and what you decided to do?

2) What did you spend the majority of your time doing in the early days with a small team? Interfacing with users, building out the product, recruiting, marketing, etc?

3) What, if anything, from your younger days prepared you to build your vision and run a company?

These questions are great ones to ask. Looking forward to an answer!

Sorry just reread that you bootstrapped so ignore #2!

1) were you wide eyes entrepreneurs when you started or is this not your first rodeo?

2) bootstrapped or VC?

3) MVP launch or stealth till first polished beta?

4) how you get your first 100 customers?