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Bootstrapping Your Way To Failure

“This has potential to be huge. I’m talking like the next Twitter huge! All I need is a good base of users and this thing will take off.”

As developers, it can be downright astounding how utterly illogical we can be when it comes to falling in love with our ideas. We’ve all been there, the Idea strikes us and our mind takes us on a fanciful journey. We envision users flocking to our new site because of how damn awesome it is. These early-adopters tell their friends, and those friends tell their friends. Before we know it, we can’t even monitor our swelling bank accounts because we’re too busy saving the world with The Zuck.

Sadly, the actual process looks more like this:

  • We get idea fever
  • We go into whirlwind mode, coding for weeks or even months
  • We “launch” to our audience of zero
  • We enter the trough of sorrow
  • We finally shut it down and chalk up another failed idea

Luckily, we didn’t quit our jobs during all of this. We did, however, miss out on nights with family and friends and all the other fun stuff that our Idea was supposed to get us more of. What happened?

Frameworks of Failure

The good news is that it isn’t entirely your fault. In most cases, you were infected with idea fever and were doomed from the start. Much like running a marathon with a parachute strapped to your back, you entered into a contest where there can be no winners. The business framework you were using was faulty. Here’s a few frameworks that bootstrappers should avoid:

Social - Look, it’s hard to see the success of Facebook, Twitter, Pinterest, and the rest of the social networking darlings. Of all the failing frameworks that we looked at, none are quite as alluring (and doomed for failure) as social ones. We’re not saying that it can’t be done, but the sheer number of early adopters needed to succeed in the social game are staggering. Not only that, the payday for social is years away. It’s hard to make money when you’re not selling anything.

Profit Un-motivated - It can be similarly tempting to create a product for the non-profit sector (didn’t patio11 sell over $8,000 worth of bingo card software in a month earlier this year?). Schools, charity organizations, and other non-profits are ripe with inefficiency. It can be tempting to look at certain populations with your developer hat on. Stop. Your developer hat comes later.

For now, put on your business hat. Most nonprofits are in a constant state of “fire extinguishment.” Their systems are broken and they’re most likely going to stay broken. Much like social, a bootstrapped startup in the field isn’t completely doomed for failure, but it is an uphill battle. Wouldn’t you rather play the game with the odds in your favor?

High Touch Sales - In the beginning (and possibly for many years), you’re going to be wearing lots of hats. This includes the sales hats. If this makes you cringe, you’re not alone. Somewhere in the heart of every developer is a small voice that screams, “I’m not in sales, dammit!” But the reality is that business doesn’t happen without sales. Which means that you are in sales, like it or not.

Dependent on the business that you’re bootstrapping, the amount of “touches” needed to convert a lead to a paying customer can run the gamut. If you’re selling a “high touch” product, you’re either going to require some hired help or make the day longer than 24 hours.

One-time Events - For anybody who has planned a wedding or any other type of large scale event, you know what a logistical nightmare it can be. At first glance, this may look like a promising business opportunity. Software could definitely help this situation out and people planning big events already have one hand in their wallets.

Before idea fever sets in, ask yourself this, “what is the likelihood of this audience needing my services month-after-month?” Not so good, right? Of course, if you’re looking at an audience that plans events for a living, then you may be onto something.

Optimizing for Success

So, now that we’ve laid out four business concepts that bootstrappers like yourself might want to avoid, you’re probably wondering, “what sort of business should I create?” Unfortunately, this question is a little bit more difficult to answer. The truth is, there is no magic formula for guaranteeing success. There are, however, things that you should be looking for when you’re analyzing your target market.

Solvable Problem - This one sounds like a no-brainer but you’d be surprised how many bootstrappers set out to tackle a problem that software simply can’t solve. If an organization is failing because of shitty management, a new app that optimizes their workflow isn’t going to do squat.

Independent - With all the recent news over Twitter locking down its API, it’s a wonder that so many devs are still building apps that are highly co-dependent. Build a technology foundation for your business that can stand on its own and you won’t wake up one morning to find one of your legs taken out from under you.

UDM Accessible - Take another look at your target market. Can you get in touch with the Ultimate Decision Maker (i.e.: the one who’s going to being paying)? If you can’t, you may be setting yourself up for a “no touch” sales process. And no touching, leads to no sales.


Plans are worthless, but planning is everything.

Dwight D. Eisenhower

There’s no easy path when it comes bootstrapping a successful software company. But there are nearly unlimited paths that are destined for failure. Before laying down a single line of code, be honest with yourself. If you’re using a Framework of Failure, all your other plans of world domination are useless.

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