Founder Diaries: Startup lessons from Wordfleet

Posted: March 16, 20226 min read

At DigitalOcean, we believe our community is bigger than us, and the ideas of entrepreneurs and builders of all kinds are essential for innovation and growth. That’s why we started the Founder Diaries series as a place for our innovative customers to share the lessons they’ve learned as they build their businesses.

WordFleet is a company dedicated to making WordPress hosting easier, faster, and more affordable using modern technologies. WordFleet partnered with DigitalOcean to help customers access the power of cloud services without the stress of maintaining backend infrastructure or the price tag of a full-service managed hosting solution.

We spoke with Founders Phillip Elm and Jared Taylor about their experience building a business from the ground up.

Q: What’s the story behind WordFleet?

Phillip: WordFleet was created to solve a problem that I and many other software engineers have experienced in our careers. We work with solutions like Docker and Kubernetes all day, seeing the best that modern technology has to offer. Then, when asked to install or manage a WordPress site for our company, we’re left with expensive managed hosts, or low-quality shared hosting that hasn’t really changed much since the early 2000s.

Realizing how out-of-date the WordPress hosting market was, I reached out to Jared, and we decided that there was a market for modern software dedicated to making WordPress faster and more cost-effective in the cloud.

Having worked with DigitalOcean’s partners program at a previous company, it was a natural choice to sign on as a partner. We then ventured to create a platform that handles everything from updates, backups, installations, imports, copies, restorations, and more.

We’ve been working on this for about four years now. For two years, I was working on this part-time and maintaining a full-time job. After that, I jumped on full time and we brought on some additional engineering talent. So overall, it was a four-year process from ideation to beta launch. We’re now publicly launched and working toward continued growth.

Q: What’s the biggest challenge you’ve faced as an early-stage startup and how did you overcome it?

Phillip: The biggest challenge for me was sticking with it. We decided to bootstrap the company with our own savings, and that made it an uphill battle in some cases. The more we put into it, and the closer we got to launch, the easier it became to stick with it. Bringing on some additional engineering talent helped a lot as well.

Jared: Phillip and I have both worked in startups previously. We know the startup journey and what it takes. So the concept wasn’t a struggle, but making the decision to fund this ourselves was a new challenge. We had to pick up a lot of hats that were initially unfamiliar to us.

Phillip: It’s worth mentioning too that being an early-stage startup in the midst of lockdowns was an extra challenge. It was very isolating and it had a noticeable impact on my mental health. Taking the time to rest and finding ways to avoid burnout were critical to us getting this far. I learned to make sure that in every decision, my mental health came first and my company second. WordFleet only benefited from that decision.

Q: What’s the one thing that you’re really proud of, and one thing that didn’t go as expected?

Phillip: For me, I think as a company I am most proud that we’ve launched. A lot of startups don’t get that far. Personally, I’m most proud of the stack that we have. Our design / technical debt is really low - lower than any company I’ve ever worked at - new or established. We took the time to spec it out and do it right. We could turn this company on a dime if we needed to.

The hardest part thus far has been all the work that goes into what happens after I hand the software to the marketing team and business owners. I’ve been on the engineering side for most of my career, and so a lot of the marketing bits are new to me. If I could go back in time, I’d tell myself to take a quick pause and learn how to market the product before it’s time to launch.

Jared: I would agree with that. If we had to do it again, we’d be laser-focused on who the customer is and what they want to prevent feature creep. We’ve learned valuable lessons from that the hard way. The launch of WordFleet is something I’m also very proud of. Coming from a business management and science background, I’m proud that I was able to get my Kubernetes certification as we built WordFleet.

Q: What would you say is your biggest barrier to growth?

Jared: We aren’t marketers. We have a great product that saves people time and money, but they don’t know it exists. While we are growing in this department, we are also looking to our partners as well as marketing agencies to help us get the word out. The customers we have so far love the product and we’re confident that once people see and experience the product, they’ll be on board for years to come.

Q: Do you have any advice for other entrepreneurs?

Phillip: If I could go back and give myself some advice, I would share four things. The first would be to figure out your funding before you do anything else. If you want investment, do the business plan early and start discussing with investors early. Set up your shareholder agreements and all those things so you know immediately what you expect from your partners. If you’re committed to bootstrapping, stick to it. Bootstrapping and seeking investors are both arduous paths that you shouldn’t take lightly. If you are going to start a business, have the savings to get you past the launch because your runway is everything.

Second, don’t become a yes person. We noticed early on that we were tempted to say yes to all the questions from potential investors, partners, and customers. Set your boundaries as a business and stick with them until you launch. Don’t make promises that are outside of that box. Decide what your business will do, set your limits, and decide how to sell those limits in a positive way.

Third, get the legalities sorted out. Know your market, including tax-wise. If you are in software, know how software licenses work. If you are in SaaS, learn the tax and privacy regulations of the areas you serve. Get to know a good legal firm and accountant. Do this early so you know the limits of what you can and cannot do in certain places.

Fourth, don’t look at launching your business as the end of the race. It’s just the beginning.

Jared: It’s not for the faint of heart. If you’re going to start a new business, the number one thing you need to have is people around you that you absolutely trust. We take that very seriously here. You have to have a team, partner, or group that you trust and also make sure that you build partnerships with companies that you trust.

Phillip: Agreed. Relationships are everything. What will make you or break you is who you partner with. Don’t do business alone, or with people you don’t trust.

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DigitalOcean supports all types of applications, from basic websites to complex Software as a Service solutions. From Droplet virtual machines to App Platform, our Platform as a Service offering, and Managed Kubernetes, we provide the tools you need to build and grow your applications. Hatch, our global startup program, can help you power your business with easy-to-use infrastructure and the support you need to get growing. To sign up for a DigitalOcean account, click here.


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