The Idea: Invoicing for Freelancers

(and why I think it will work)

As I mentioned in “What’s this all about?“, I’ve had the startup bug since I was 12 years old, as I watched my Dad struggle with and build a successful software startup. I’ve been coding for about that long as well. Since I began writing software professionally around the year 2000, I’ve had something going on the side (“nights and weekends”-style), dreaming of the day when I could quit my day job and go full-time. I didn’t want to become a billionaire or build an empire — I just wanted to make my own decisions, mistakes, and schedule.

For technical founders, building something is the fun and easy part, so we often start building way too early. Fight the urge to write code until you have clear validation first.

My Github account is full of half-baked or failed startup ideas. Some of them kept me going for months, but it turns out that building is the easy part. Launching, finding product-market fit, marketing, and getting people to pay for it? That’s the hard part.

The Embarrassing Part: My Ten Failures

As I share my progress, I’m going to share it all — even the embarrassing stuff. Here are a couple of examples of things I built that went nowhere.

  1. A dating app. In college (2001), I built a dating app just like every other CS student was probably doing. was in the news for being led my one guy in his bedroom, and I thought “Well, if he can do it, I can too!” It is so embarrassing to look back at, but here you go. The name? Let’s just say Ricky Martin was all the rage at the time and I was not very creative. To market it, I picked up a pack of blank index cards at Walmart and printed (on my cheap inkjet printer) little mini flyers. I stuck those in every apartment door and car window across campus. It even resulted in my first sale! I was so embarrassed that I only had one paying customer (at the time) that I actually refunded them without being asked to. Why it failed: I had no idea what I was doing and I basically gave up.
  2. A contact syncing web app. Back in the early 2000’s, you had to back your phone contacts up on your sim card to move them to a new phone. If you forgot, you lost them all and had to all start over (“new phone, who’s this?”). My thought was “Wouldn’t it be awesome if you could store all your contacts online and sync them between phones?”. It was (that’s exactly what Google and Apple do now). Why it failed: I failed to see how it was just a matter of time before phone software caught up, and a little guy like me wasn’t going to be the pioneer who made it happen.
  3. Case Tracking Software for Lawyers. As I was making my way through school, I worked as a paralegal and saw first-hand how awful case management software was. I knew I could build a better mousetrap. Why it failed: I had two young kids and the nights-and-weekends thing just wasn’t working for me. I fizzled out.
  4. Bug Tracking software. As someone who used bug tracking software every day and hated all its quirks, I thought I could build a better mousetrap. Surely it couldn’t be that hard to build, right? Why it failed: I spent several months building it and actually got several beta users before I realized just how complex it could get behind-the-scenes when it came to workflows and automation. I wasn’t passionate about bug tracking, so I fizzled out. It’s an established market though, and there’s still room for competition (just not by me).
  5. Boy Scout advancement tracking. As an Eagle Scout and Boy Scout leader, I knew how hard it could be to track the progress of all of your scouts over time. The existing software was old and built by people who had just hacked things together. Surely I could build something more intuitive, right? I actually succeeded in building it, and launched it after my beta testers said the loved it. Why it failed: I chickened out after a competitor threatened to sue and blasted me all over the online forums. I was bullied and didn’t have thick enough skin. It may have worked if I had stuck with it, but it was still a nights-and-weekends thing for me.
  6. A Field Service (i.e. Pool Service or Pest Control companies) app. Back when everyone was just starting to have smart phones with GPS and reliable data service, the time was ripe for companies to be able to manage their businesses completely (or at least mostly) on their phones, instead of back at the office. This time I even had a co-founder: a marketing/sales guy who wasn’t afraid to hustle and get out there in front of people. Why it failed: Work (my full-time job) got the best of me. After the initial prototype was launched, I ran out of steam. By that time, Jobber (a Venture-backed startup) seemed to come out of nowhere and dominated the market we were hoping to serve. I had to focus on my family and job, and my co-founder and I ended up simply drifting apart.
  7. Reusable Checklists. The stars seemed to align on this idea, and I was excited by how broad the use-cases could be. Coincidentally, I had just finished reading “The Checklist Manifesto” when I came across this post by @ev (co-founder of Twitter): “The Reusable Checklist“. Why it failed: I still think this is a fantastic idea, but I dug in and started building before I fully vetted my idea. When I finally looked into potential competitors, I found a few Indie founders that had built fantastic solutions to the same problem (inspired by the same book and post, even). I didn’t think I could differentiate myself enough.
  8. A “White Elephant Gift” idea website. This was almost a joke, really. I built it to learn Rails while I was playing around with the idea of Amazon Affiliate marketing. I set up a site (inspired by This Is Why I’m Broke, which curated a bunch of funny White Elephant gift ideas. The first year, without even trying (pure organic search results), I made a couple thousand dollars on affiliate fees from Amazon. The next year I was making hundreds per day. People would click on a link for funny socks from my website, end up buying a TV on Amazon, and I’d get a handsome affiliate fee for referring them there. It was so successful that I turned it into a multi-tenant/multi-site app that would let me eventually set up dozens of affiliate sites. Why it failed: I got shut down hard by Google. They took a manual action against me (de-listing it) because it seemed too spammy — just a link farm, in their eyes. I did my best to enhance it and make it more editorial and by adding significant unique content with each item, but Google wasn’t having it. They rejected my appeal and that was it. My traffic disappeared overnight.
  9. A web crawler that looked for and alerted you to broken links. This is a project I built for fun in order to learn about the AWS tech I was digging into. As I built it and tested it on a few different sites I owned, I realized just how useful it might be. It found dozens of links I had no idea were broken. Marketing could be automated easily as well: I could simply crawl sites and email the owners with “Hey, did you know these 30 links are broken? By the way, we can keep an eye on that for you”. Why it failed: Turns out this was a good idea, but not enough to pay for on its own. That’s why companies like SEMRush and Ahrefs have it built into their suite of tools. It turned out to be a good learning opportunity for me, but not a viable business (on it’s own). I didn’t really want to compete with those other SEO companies.
  10. A mailing list web app. Like Google Groups, but for businesses or non-profits. At this point I was starting to realize that I didn’t want to invent something totally new. After having consulted for a non-profit for years, I knew something better was sorely needed. There were established competitors out there (old and new), but it felt like there was still a niche I could fill. Why it failed: I changed my mind after I launched it and was immediately inundated with spammers using it for evil. I realized I didn’t want to deal with email and all of its quirks.

These were not just ideas I had — these were all things I built and launched! I have dozens more half-baked projects as well.

Back in 2013, I was even naรฏve enough to think that any software engineer could strike it rich, if they’d just built something. That article even hit the top of Hacker News twice (once when I submitted it, and once when someone re-submitted it later). Wow was I naรฏve. Like I said, building is the easy part.

As I look back, one theme I see is that I either: 1) built something because it was fun and exciting without properly vetting it first, or 2) didn’t have the tenacity to stick with a good idea (usually because I couldn’t dedicate enough time and energy to it).

So what’s different this time?

I began freelancing in 2005 to supplement my full-time income. My first clients were former clients of my employer who needed small updates here and there and didn’t want to go through a full-blown agency. I responded quickly and obsessed over their happiness, and in turn, they referred me to other clients. Before long, I had a nice side-gig that I would continue with for the next 10 years. I never went full-time doing consulting work, because I had a young family and preferred a steady paycheck, but the extra $1,000 here and there was a lifesaver.

The thing I despised doing each month was sending out invoices. I owed my clients more than an email with a total they owed, so invoices were a necessary evil, but they also meant spending time doing something I wasn’t specifically being paid for: creating and sending out invoices. Getting paid was fun, but putting together invoices sucked.

There were (and are) invoicing web apps out there to make this easier, and I often used them. The problem was that while they made my invoices look good, the apps were either way too complicated and overwhelming (meant for larger teams/agencies), or way too clunky (thrown together by people who didn’t think the experience through). In the end, I just wanted something that would make creating and sending out invoices quick and easy. I wanted in and out.

The other problem with sending out invoices is that you never know if your check is on it’s way or not. More than once, I would be waiting for a large check that hadn’t come in 6 weeks or more, and I would awkwardly reach out and ask if they had sent payment yet, only to find out they never received the invoice. Email “read receipts” didn’t always work, and it was always awkward to follow up. I wanted something that would automate the follow-up and payment part.

Finally, back then there was no easy way to get paid online. There was my personal Paypal account, but that felt too amateur. Stripe didn’t yet exist. I would have easily sacrificed the 3% fee to get paid instantly.

All of these problems have now been solved by my future competitors. Isn’t that great?

(No sarcasm here — it’s awesome!) Now that they’ve done the hard part of figuring out what customers want from an invoicing solution, I can focus on what differentiates me from them and carve out my own little niche.

My niche will be an under-served part of the market: freelancers who need a quick and simple way to send out invoices and get paid online. The “big money” is in teams and agencies. I may get there some day… but in the mean time freelancers like me are still left with the same problems I had 10 years ago: overly-complex apps (“All I need to do is send out a simple invoice, dang it!”) and clunky/outdated software that is confusing and overwhelming to get started on.

So what’s different this time? Three things:

  1. I’m entering an established and fairly mature market. Product-market fit (in general) has already been solved. This gives me a clear idea of what the minimum features I need to build in order to launch are. The inspiration for going in this direction was inspired heavily by “How to find startup ideas that make money“.
  2. I’m finally able to work on this full-time! The difference this makes in terms of how quickly I can move and launch is incredible. I didn’t just suddenly quit my day job. I dug in and did my research to make sure I wasn’t making a huge mistake, spoke with as many freelancers as I could, and hacked together a prototype to get a feel for how complex it would be to build.
  3. I’m passionate [enough] about this idea to iterate on it for a long time. It’s not that I’m passionate about invoices (I’m not that weird), but I am passionate about the customer experience and helping freelancers get paid faster. I’m not going for a “minimum viable product” here — I’m aiming for “minimum loveable product”.

There are so many clear ways I can serve my customer-base and come to dominate my niche (“simple invoicing for freelancers”). I won’t focus on teams or agencies until/unless I really need to.

Based on my research over the 20 most obvious competitors (using the term loosely, because some are awful), freelancers are a seriously under-served market. Some competitors throw the words “and freelancers” in their taglines, but they don’t mean it. The funded (Angel or Venture-Backed) companies can’t afford to focus only on freelancers — they need agencies and teams for that expansion seat revenue. The Bootstrappers all try too hard to sound bigger than they are (corporate). My angle is that I’m a freelancer helping other freelancers. Although my goal is to make money (obviously), my goal is to help freelancers in every way I craved when I was in their shoes.

How I vetted my idea

This is a topic all on its own and one I want to cover in more depth in my next post. I’ll include specific steps I took (that you can too, even if you’ve already started). It’s not earth-shattering, but for someone like me who wants to build something to replace their normal income (and not necessarily build an empire), it makes sense! Follow me on Twitter and I’ll drop a link there when it goes out!

Risks I will need to overcome

I have one shot at this (full-time), and I’ve failed enough times to realize that success isn’t guaranteed. These are the risks I will need to be aware of and deal with.

  1. Price sensitivity: Most invoicing solutions out there are priced very low. It’s almost a race to the bottom. $7 or $9 a month per user is common. At that price, I’d need 1,400+ monthly subscribers to stay full-time. That’s very likely more than I can get in a year. I either need to make my solution more valuable (be the “must-have” freelancer option at a higher price), attract less price-sensitive/”high-end” freelancers in general, or find a way to attract a lot of clients very quickly.
  2. Marketing costs and time: One of the hardest parts of starting out in an established market is that competitors have already figured out what works and are pouring time and money into it. While I have the advantage of being able to move much faster, they have deeper pockets. Marketing is hard because so many approaches take time to even know if they’re working.
  3. Freelancers aren’t targeted for a good reason: There could be a very good reason that freelancers aren’t specifically targeted that I’m simply missing. Maybe they’re just not willing to pay for invoicing software. Maybe they’re too transient (not enough full-time freelancers). Maybe something else. In this case, I will need to adjust and find a way to compete against the team or agency-centric apps out there.
  4. I only have a year of runway: This is my most concerning risk, because marketing and SaaS growth takes time. There is no such thing as “If you build something awesome, people will suddenly find it and pay you for it”. My goal is to launch something by August 1, 2021, so that I can spend the rest of the year on marketing and responding to feedback… which leads me to my last risk:
  5. I’m starting from zero with my marketing. I don’t have an established audience or “early access” list. While I have vetted my idea with as many freelancers as I know, they’re not guaranteed to sign up and they wouldn’t be enough even if they did. I’m going to need to find a way to get in front of as many eyeballs as I can, quickly.

I feel like the odds are stacked against me, but I’ve seen enough people succeed that I know it’s possible. I know I’m capable, and I know there is a market need out there (that people are already paying for).

Wish me luck!

Oh hi there ๐Ÿ‘‹ Itโ€™s nice to meet you.

Sign up to receive periodic updates about things I learn that may help you too!

Spam sucks. I promise not to abuse your trust.

If you found this article interesting, please share the love!

2 comments on “The Idea: Invoicing for Freelancers”

Leave a Reply

Your email address will not be published.