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Ryan Battles Interview – DRAFT

1. For those unaware, what is Harpoon and what does it do?

At its core, Harpoon is a platform that helps freelancers, studios, and agencies set and hit a yearly financial goal for their businesses. We accomplish this with a mix of education combined with a killer app that handles everything from financial planning and budgeting, to time tracking and billing.

2. What’s the difference between Harpoon and other invoicing apps?

Many other invoicing apps track time, create invoices and collect online payments. We feel that is the minimum that any invoicing app has to do well. However, there is a lot that other invoicing apps don’t do well, which is helping you to set and reach goals.

Freelancers often run their businesses in a reactive state, instead of a proactive state. I’ve done both, and it wasn’t until I began getting serious about goal-setting and tracking that my freelance career took off.

3. What’s the number one mistake you hear of time and time again with Freelancers when it comes to invoicing?

Beginning freelancers are often too loose with their terms as a business, and can be taken advantage of by clients who either don’t pay, pay late, or allow scope-creep to kill the profitability of a project. There are even programs out there that offer a loan to the freelancer until the client pays.

While there are probably situations where this is a good idea, by and large with freelancers it isn’t. Instead of giving a micro-loan, we should be teaching freelancers to be strict with their down-payment policies, write better project scopes, and become smarter about their deliverables and payment terms. Once I learned how to do this well as a freelancer, the late payments from clients mostly became a non-issue.

4. What gave you the idea behind Harpoon?

As a new freelancer, I was on a roller coaster ride of emotions. When the large checks come in, you feel like self-employment is amazing. You might even become less aggressive with acquiring new clients for a short while. Conversely, when a dry period hits, you start to question whether you can even make it as a freelancer, and consider applying for a traditional job again.

Harpoon was born out of the desire to take the over-reaction and emotions out of the freelance ups and downs. By setting a specific goal, tracking your progress towards it, and visualizing where you are heading in the near future, decisions can be made in a logical fashion that maximizes your financial success. With Harpoon, I get that needed kick in the pants at times, and other times it gives me the peace of mind to take a vacation without making it a “working vacation.”

5. What has been your biggest struggle launching a SAAS product?

At first, running a SaaS business seems like the dream life: people just keep paying you money every month! However, each customer is paying you a relatively small amount, so a SaaS product can only sustain itself after you’ve grown a considerable customer base. So, in the meantime, you either need to ask for funding, deplete your savings, or maintain an income in another fashion.

For Harpoon, we’ve decided to bootstrap the product so we can always keep our customer’s interests first, instead of having to worry about pleasing investors. This means that growth is going to be much slower, and more energy is going to be needed to keep the business moving forward. Our biggest struggle has been finding ways to balance our energy as a group and maintain momentum during a slow, but steady, initial growth period. However, we have experienced a lot of wins and have celebrated new milestones together, so in a way, it feels like we’re just getting started even though we’ve been around over a year.

6. Where did you start out and how did it lead to Harpoon?

I started off teaching high school computer classes, with the side hobby of building and maintaining the school’s website. Eventually, I realized that I loved making websites, and decided to take on freelance web design/development jobs until I had a steady enough income to quit my teaching job.

Through the years of freelancing, I learned not only how to survive as a freelancer, but also how to thrive by running my business more professionally, and hitting my financial goals along the way. Being pro-active helped me to say no to projects that I wanted to say yes to, but there was no way I could fill my time with these types of projects and still attain the income that I had set out to achieve.

What Harpoon now does automatically for many freelancers, I had to do with spreadsheets and scraps of paper. It made sense to me and my business partner, Andy, that we needed to build a tool like Harpoon to not only help ourselves rely less on spreadsheets, but also to make it super-simple for other freelancers to use and leverage for their success.

7. What has been your main weapon you’ve used to get through this?

One of the indispensable tools in our business has been using Intercom for customer communication and analytics. We use this tool for our customer support, feature requests, and pre-sales support. Additionally, we leverage it in our onboarding flow, to engage new users automatically and dynamically.

Another useful feature with Intercom is the ability to send it custom data per user, so we can track which advertising campaigns lead to the most engaged users, or when a new mention on the web starts sending up new signups. With Intercom, we are measuring what is working well and which efforts aren’t producing results.

8. Where do you see the Freelance movement going in the next 20 years?

There is no doubt that freelancing is going to become more and more commonplace throughout the near future. Already we see a spike as the ability to work remotely has exploded. Through video conferencing, team-communication suites, and file-sharing apps, many workers can do their jobs without the need to be in an office.

As employers are embracing the work-from-home movement, many are also considering freelancers where they hadn’t before. And with tools like Harpoon, freelancers don’t need to worry so much about the business tasks that used to take up so much time and mental energy. Now things like turning time logs into invoices and sending out automatic payment reminders allow the freelancer to focus on what they do best.

9. What can we expect from Harpoon in the future?

The future is looking bright for Harpoon. As we continue to experience growth, we are committed to being there for both the existing freelance workforce and those who are new to self-employment. We have an internal roadmap of new features to add based off of customer feedback, and as always, we will be releasing new features on a regular basis.

10. What was the main skill you had to learn whilst creating Harpoon?

Harpoon was initially built in the nights and weekends when I wasn’t working on client projects. We didn’t have any users while we were building it, so we just had to work hard to create it in our free time. A skill that I had to learn relatively quickly is to not only achieve balance to prevent burn-out, but also to communicate effectively with my wife and business partners.

I learned that most disagreements and frustration arise out of unmet expectations. Effective communication with those you are close to in life keeps everyone on the same page, minimizing the misunderstandings. Oh, and I learned Laravel PHP development, but the former was a more valuable lesson 🙂