This is an interview-style post with Tim Chaves, CEO and Founder of ZipBooks.

Hey Tim. What’s your background and what do you do?

I’m the founder and CEO of ZipBooks, which is accounting software optimized for small business owners (rather than accountants).

Ever since high school, I knew entrepreneurship was for me.  Though I briefly explored going to law school, I started my first venture in college and haven’t looked back since!

Tell us about your early days as a business owner. What was your first venture?

My first venture was a company called iWrap – we made invisible, protective covers for devices like iPhones.  I started it with a friend my junior year of college.  It was a great learning experience more than anything. It gave me a taste for both the misery and euphoria that often accompany entrepreneurial journeys. 

I learned how important team is. Those early days, I often thought of myself as a “superman” who could handle just about everything.  Boy was I wrong!  No matter how diverse your skill set is (and mine wasn’t), there is simply too much to do in a new venture to try to conquer with just one or two people (service businesses are the exception)

After working on it for a few years, we sold it to a larger competitor and then it was time for me to figure out what to do next!

You gave school a second chance by enrolling in Harvard’s MBA Program. Can you say formal education helped you with your current projects?

Absolutely.  After selling iWrap and a brief stint with another small business I founded (a design and development agency), I applied and was accepted at Harvard Business School in 2013.

I found my experience there invaluable. Not only did I strengthen my foundation of business fundamentals, I also met key contacts from both a fundraising and future team perspective.

When it came to raising venture capital for the first time, I believe that my MBA was invaluable in getting the credibility to get in the door and be taken seriously right away. 

As a mentor of mine has said, “your degree will open doors – but you still have to walk through them.” 

That’s exactly what I’ve found.

Google offered you a full-time position as a product manager. How did you know this wasn’t for you?

I got to intern at Google between my two years of MBA, and loved it.  When the full-time offer came in, it was definitely something I took seriously, since it was a chance to work at a company I truly admired and knew I’d enjoy.

I actually created a very detailed spreadsheet with weighted scores for every path I considered taking.

I went through several versions tweaking weights and scores, but when the idea for ZipBooks came around, I threw the whole spreadsheet out. I couldn’t not work on my idea; that organic inclination to do it was key to knowing I was on the right path.

How did you come up with the idea for ZipBooks?  What’s the main problem it solves?

zipbooks startup accounting software

I saw firsthand the state of small business accounting as a small business owner.  It was frustratingly old school, and the predominant products in the space were made for accountants.  I felt like we could get some big UX wins early on just by thinking about it as a small business owner would.

I also felt that accounting data was so rich that by applying some analysis (and even artificial intelligence), we could help small business owners drive better decisions and grow their businesses more effectively.  It’s been exciting to see that thesis come to fruition as we’ve built it out.

How did you get the word out about your new startup?

We did the normal things: launched on Product Hunt, asked bloggers to write about us, etc.  But we were also pretty scrappy. We found organizations of business owners that we felt were relevant for our product, and figured out ways to get email blasts out to them.  That kind of thing accounted for a lot of our early growth, and spurred early word-of-mouth.

What are the challenges of growing a company?

There are so many!

Putting together the right team is incredibly difficult.  Excellent people always have many great opportunities, so finding them and getting them onto your team requires a huge amount of work.

Finding product-market fit is also a challenge.  In our case, we knew people needed accounting software, but differentiating while staying true to the core need has been a line we’re always trying to balance.

You started outsourcing early on. How did you find the right people to get on your team?

Outsourcing is really a less-risky way to hire.  It’s often short-term by definition.  When you don’t have accurate cash projections, it can be scary to hire people as full-time employees. 

For remote and contract workers, we’ve used a “funnel” approach. Try lots of different people with smaller projects, and they sort themselves into groups of capability and commitment.  From there, you can choose to ramp up your work with them or even bring them on full time.

What are your plans for ZipBooks in the near future?

We’re very happy with where our accounting product is right now, and will be turning more focus on how to help small business owners manage and grow their businesses effectively. 

Accounting software has always looked to the past. We’re trying to help it be forward-thinking, and become a real advisor in helping business owners take the right next step.

What’s your advice for small business owners who aren’t sure how to go about bookkeeping?

Try ZipBooks! 😉  Seriously though, the products you’ve tried in the past have probably made it too hard.  We’ve simplified things significantly and our approach makes bookkeeping much easier.

If you’re at the point, though, where it’s most profitable for you to focus on your business, rather than spending time on it each month, we also offer an online bookkeeping service as a way to take it all off your hands.

What should aspiring entrepreneurs work on first when starting a business?

They should know that there’s truly a market for their product.  There’s been a lot written about product-market fit, and it’s really incredibly important. 

When you hit it, things will stop feeling so much like you’re pushing a boulder up the hill, and more like that boulder starts to roll on its own (even if it’s slowly at first). 

Get that feeling that there’s really “something there,” (as opposed to the feeling of “forcing it”) is when you know it’s time to invest more.

Who inspired you along the journey?

I read a lot.  Back in the early days, I loved anything put out by Tim Ferriss, and the E-Myth by Michael Gerber was an early entrepreneurial inspiration (work on your business, not in your business!). 

I’ve also had several professors from both undergrad and grad school that inspired me as entrepreneurs and as people (Srikant Datar and Noam Wasserman at HBS in particular).

After being an entrepreneur for many years, I’ve felt sort of organically drawn to expand my competence to other subjects. I’ve been on a physics kick recently: Astrophysics for People in a Hurry by Neil DeGrasse Tyson and The Fabric of the Cosmos by Brian Greene both blew my mind!  Even though I love what I do, it’s been fun and even reinvigorating to reach outside my comfort zone and learn new things!


Hope you enjoyed my interview with Tim Chaves from ZipBooks. Head to and try their simple accounting software for free!