It’s been eight months since Spreedly announced we were pivoting. Originally a digital subscription offering competing against the likes of Chargify and Recurly we decided instead to focus on being an online payment platform. We wanted to create a Braintree or Stripe like experience for companies that need to work across payment gateways.

We worried about using the term “pivot”. Was it just short hand for “delaying the inevitable”? Certainly we got that look more than once from friends and family, customers’ and potential investors. Yet more than a year after we made the decision, and 8 months after going public with it, we’re pleased with our progress. We’ve passed 125 customers, raised nearly $1 million and are processing nearly $100 million per year on the platform. To be sure we could still fail for a whole host of reasons. Yet we can’t blame the pivot. We’re well past that point.

It’s safe to say that the adoption of digital wallets has been slower than most people thought. The reasons are several. Perhaps the most important reason is that credit cards work really well, no matter what you might feel about their associated fees. Put simply, setting up a wallet for the sake of setting up a wallet doesn’t feel all that compelling to many users when credit cards are easy to use.

All that changed when I recently used Uber for the first time. Firstly, I had to create a digital wallet if you will. For the service to work the way it’s designed you need to store a card on file. Here’s what’s different though. I quickly realized once I went through this step that I’d never have to use a card again - at least with Uber. Setting up a wallet usually means switching out one way to pay with another way to pay. Setting up a wallet with Uber means never again worrying about...

It goes without saying that you need optimism by the bucketload to create and maintain a startup. Having a discussion around failure almost seems redundant given the nature of the undertaking. It’s a constant heavy cloud looming just behind your shoulder that’ll suck you in if you turn around. (Perhaps that’s why it often weighs particularly heavy at night when your head is on the pillow; there’s no where for that cloud to hide.)

Most startups get up everyday and plow ahead with that always constant presence of failure simply accepted as part of the job. The downside to this approach is that it can hamper critical, nuanced thinking. Many failed startups are simply that; good teams trying all they can but having a critical foundational flaw that makes success impossible. However, many failed startups could have succeeded if they’d done more critical thinking along the way.

One...

Startup founders and angel investors are always trying to determine how to effectively measure traction. You need to find the right metrics and you need to try and weigh the significance of each metric. It can be difficult to do - after all you’re going a lot by “gut instinct” early on. Also, it’s easy for one metric to leap ahead of others for a period of time which might be a blip or might be the long term lesson for your business.

Yet you need some metrics to measure and gauge progress. Firstly, you’ll want to answer the most basic question of all; is this a business worth pursuing? You’ll also want to gauge progress and feed that back into timing decisions around investments (employees, marketing, raising).

I saw a tweet go by in my feed the other day (I can’t remember the source but I think it was around the Mixpanel event). It talked about how important highly passionate early...