Rising StarJoshua Waldman of Billy Offers a Third Accounting Option to Entrepreneurs

Do you enjoy managing cash flows? No? Joshua Waldman understands your pain. After rescuing the company from a financial meltdown, Joshua became the CEO of Billy, a provider of easy and intuitive accounting software for entrepreneurs. He shares an important lesson for running a software company, tells us why accounting software designed for business owners is important and offers a unique opportunity for a developer who specializes in Node.js.

Read more from Joshua below:

The problem it solves: Most small businesses fail in their first two years largely on account of not having cash flow. Let’s face it, most founders, or freelancers, are not MBAs, accountants or bookkeepers. They have a passion, or an idea or a skill and they sell it. So very often cash flow management is relegated to the “I’ll deal with it later” bucket and is handled in spreadsheets.

The spreadsheet session ends when either (1) tax time comes around and their accountant has a heart attack at how the books were managed and the founder gets a huge bill for hours spend sorting it out, or (2) that little spreadsheet grows and grows until it’s actually painful to track bills and invoices on it.

At that point, there are only two crappy choices. One is to hire a bookkeeper, and most small companies can’t afford a good one. The other option is to buy accounting software that requires accounting training to use, in which case, see option one.

How you are different than your competition: Most accounting software is written and designed for accountants, not business owners. Billy was engineered to make bookkeeping and tax time totally easy for the founder or freelancer without the need for outside resources. We found that most of our users want simple software, not more complicated features. We have “number-hating” freelancer designers who actually tell us they love logging into Billy. Go figure!

How you make money: We sell Billy in a monthly or annual subscription in three tiers. We also have onboarding services to help business owners get set up for the year so they don’t have to hire a bookkeeper.

The best thing about being an entrepreneur: Not having a boss (besides my wife), not having a soul-sucking corporate culture, freedom to make decisions, having a responsibility that extends beyond my cubicle, freedom to take a day off just because I want to. Shall I continue?

Your biggest success: I rescued Billy from a financial meltdown. When I came on board, our main funding source had suddenly stopped. There was no future for the company. So I approached the founder and said, “I believe in Billy. I think it’s a good product. Rather than let your last 2 years of investment go to waste, why don’t you put me in charge of it. Give me 3 months and don’t pay me. If I can’t save the company and dramatically improve our MRR, then I’m not the right guy for the job. If I do save it, make me the CEO.”

He said yes. In three months we had Billy launch on Appsumo, gained $40,000 in operating revenue and went from 100 to 4,000 users.

A failure story and what you learned: I’m not a technical founder. I don’t know what questions to ask developers. I don’t know the best processes for QC before a pull request. So, I hired a team of developers to separate our code from its base in Denmark. When it was all done, the team wasn’t ready to start developing new features for us because they didn’t have the right node.js resource. So, this added a 30-day delay to our roadmap and 30-days off of my capital runway. A technical founder would have asked about resources and thought beyond the current project in a specific way. Lesson: don’t try to run a software company without a technical co-founder.

What keeps you up at night: We had an interruption with a service a few weeks ago that lasted a lot longer than it should have. I couldn’t find a way to sufficiently motivate my developers to fix it faster and I knew my users were suffering. It was killing me to not be in more control of the development process and it was terrible knowing my users were having a hard time because of me.

The best entrepreneurial advice you have received: One of our advisors on the board told me once, “Whatever the customer asks, give it to them. The chaos you might have to deal with later isn’t worth the cost of fulfilling their request.”

We had a customer ask for a full refund, for the whole year, because we hadn’t rolled out a feature he’d requested soon enough for his liking. I didn’t want to do it. She advised me to do it. I think I avoided a social media crisis by following her advice (and for you smart alecs, don’t start asking for free stuff! I’m onto you).

What makes you a good entrepreneur: I don’t think I’m a very good employee. I think a good entrepreneur has trouble sitting on their hands when they see a problem. An employee has to follow protocol and process, or use bad software because that’s some deal some executive signed up for. This drives me nuts, especially when the process gets in the way of serving a customer or getting better results. If there’s a better way to do something, I’m gonna squirm.

The #1 book you would recommend for a budding entrepreneur: Running Lean (and it’s sequel, Scaling Lean)

A song that best describes your entrepreneurial journey: A labyrinth

Your favorite local business: Cacao. It’s happiness in a cup

What you wanted to be when you grew up: An astronaut, fireman and taxi driver all at the same time, what else?

Do you think Oregon is a good place to start a business? The lifestyle here can’t be beaten, but it’s been hard finding developers. Plenty of designers, writers and creatives, but not that many experienced coders.

Any other tidbits or fun facts to share? I run a ukulele group in Tigard: http://tigardukes.com Come join us!

Find out more: https://billyapp.com/

OEN members can get 20% off of Billy for life! https://billyapp.com/oen/

Billy is looking to hire a developer who specializes in Node.js. If you or someone you know is interested, find out more here: https://billyapp.com/were-hiring/

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