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Featured Member: Freelance Planning App Harpoon

When Ryan Battles went solo, he realized just how little business planning many freelancers engaged in. His solution was an almost overnight success.
Editor, Anne Miller
September 25, 2017

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Ryan Battles’ entrepreneurial inspiration started with two tiny, screaming babies.

Battles quit his job as a private school teacher when he and his wife had twins. When the babies slept, Battles taught himself web development, did projects for places like Google, and had another realization—freelancers can be terrible business planners.

Harpoon is Battles’ attempt to address that problem. The web-based subscription platform tracks money, but also keys into business planning questions that help freelancers turn projects into a steady business. Launched in 2015, Harpoon has already generated press in Tech.co and the San Francisco Chronicle, and attracted a growing client base.

1. Why did you start your business?

As a freelancer, I experienced a cycle of feast and famine when it came to income. I didn't really have a plan. After about a year, I decided I needed to track my income against a goal for the year. I did this using a spreadsheet, and realized that there was an opportunity to build an app that automated much of the math and graphs. Harpoon shows freelancers how they are tracking against their goals, shows expected upcoming revenue and breaks down many other aspects of running a business. 

We help answer questions like:


  • I've had a good month, how does that change my goals for the rest of the year?
  • How many days can I safely take off for vacation and still hit my goals?
  • What would my income be if all of my clients paid their invoices today?

2. What business hurdles have you overcome?

The biggest hurdle for me and my two partners was figuring out how to build and market this self-funded company while maintaining other sources of income. Besides communicating clear expectations and commitments to each other and the company, we have also begun hiring other freelancers to help out with development and content marketing. This has freed us up to focus on the most important aspects of the business, like reaching new customer groups, providing product direction, customer communication and pursuing partnership opportunities.

3. What's your most memorable business moment?

Before we launched, I reached out to some journalists who had covered products like Harpoon in the past, to see if they would be interested in hearing about our new offering to the growing freelance market. I wasn’t sure what to expect, but I had never been behind a company before that made headlines. The day we launched Harpoon we had write-ups in national publications. I’ll never forget that feeling, knowing that we were no longer working on a side project as freelancers, but that we had a viable business the world was talking about.

I realized Harpoon was going to scale when we started receiving overwhelmingly positive feedback from customers that weren’t already our circles. Once strangers were tweeting out how much they loved the tool, and customer support messages came in stating that our new users had been searching for a tool like this for a long time, we knew we had something.

4. What are your tips for designing an app?

As a freelancer, I usually only had a handful of clients trying to contact me during any given week. When you own an app, you have hundreds or thousands of customers clamoring for your time. Because so many people find the design and user experience intuitive, our support requests are quite small compared to the size of our user-base. I would encourage any business owner looking to design an app to not skimp on the user experience design. Shortcuts you take in this area may turn into customer support issues down the road.

5. What are three things you couldn’t live without?

The three things I couldn’t live without as a business owner are:

  1. My Mastermind Group. Every other week I meet with three other entrepreneurs who are also running a SaaS (software as a service) company, and we share our wins and losses, as well as goals for the next two weeks. At each meeting a couple of us are on the “hot seat,” where we deep-dive into a current business problem we are experiencing. The feedback and suggestions from this group have been motivational and effective in helping me grow as a business owner.
  2. Notepad App. I’ve tried many productivity tools over the years, and the best for me is the lowest-tech option out there. I simply keep a plain-text document that lists out a general outline of each day of the week. Rarely does each day go exactly as scheduled, but I have found that starting with a plan is an essential strategy for getting the right things done.
  3. Conferences. Every year I attend at least one conference that inspires me as an entrepreneur (this year it was MicroConf in Las Vegas). The networking opportunities are unparalleled and open up doors for conversations and partnerships that can be game-changers for your business.

A version of this article was originally published on May 10, 2016.

Photo: Amanda Raines, courtesy of Ryan Battles
Editor, Anne Miller