Regarding Edgecase

I mentioned this in my prior post, but I wanted to highlight it on its own. Not everyone yet understands how modern web development is done and how powerful technologies like Ruby on Rails and its associated ecosystem are. But one company that does is Edgecase. They’ve been our partner on VacationTrade for many months now and I couldn’t be more happy. If you’re looking to hire a team of people to help develop a web application the right way, you really should take a look at Edgecase. Thanks again guys.

A year (or more) in the life

December 23, 2009 at 9:45pm EST. That marks the official time when the project/company that has consumed my life for a year (really more) was finally open for business. Check it out at and get details about what it is we do at If you own a timeshare and have become frustrated with the experience of trying to exchange it through RCI or Interval International, we hope we can make your life better.

The site is in an alpha state right now. That means it basically works but it’s not hard to find bugs or opportunities for improvement. There’s a saying in the startup world – if you’re not embarrassed/worried by the first release of your product, you waited too long to release. I also like what Paul Graham had to say in his essay on what startups are really like:

It’s so important to launch fast that it may be better to think of your initial version not as a product, but as a trick for getting users to start talking to you.

Alright users – speak up!

The past year and change has really been a whirlwind. It actually all started in April of 2008 when Mike Blackwell and I decided we wanted to form a company together. We just needed to figure out what it was to do. I could not ask for a better person to go through my initial startup experience with than Mike. As the former CEO of ShareThis along with getting in on the ground floor of a prior startup that crashed and burned, Mike knew the ropes and was able to properly set my expectations and helped us to focus on the right things. He is also a great guy who has an integrity and perspective on life that I really admire.

Over the course of the past year, we’ve had several other folks come along and join the team in one way or another. Once we had settled on the right business idea (after many false starts), Bob Kington and LJ Freeman got involved as co-founders of the company in May of this year. In July, Sara Gibbons joined us and in November, Kevin Munc became employee #6. Gina Winkler also spent a fair amount of time on our project as did several other friends. And we could not have done this without the help of the guys at Edgecase, most especially Adam McCrea.

So, come and check us out and let us know what you think. Yes, I’m slightly embarrassed about the site’s flaws and shortcomings, but I guess that means we released in time. The next several months are going to be extremely busy (just as the past several have been) while we react to feedback and make improvements. I take it as a good sign that there’s a big part of me that wants to get started on those right now. But, it is Christmas time and rest and family time are also important. Have a Merry Christmas everyone and may your 2010 find you as excited by life’s opportunities as I am.

About Last Tweet

Earlier today, I tweeted that I couldn’t recommend Braintree as a payment processor. It was a tweet born of frustration and would probably have better been kept to myself. But now several folks have asked for an explanation, so I’ll try to do so in a way that is fair to Braintree.

There are several good reasons to like Braintree as a processor for your site:

  • They allow you to treat payment processing and merchant account handling (two separate things) as if they were one.
  • They relieve you of the requirement to hold sensitive data (i.e. credit card numbers) in your database, thereby making PCI compliance much less of a headache than it need be
  • They have a well documented and relatively simple API to develop to that is a piece of cake to integrate into a Rails app
  • They have some folks on staff who are Columbus Ruby Brigade alumni

So, after a brief survey and at the suggestion of colleagues, we decided to use Braintree for our site. We’re not yet live on that site, so I’ll keep details of it somewhat private at this point. But you can think of the site as one that uses a model similar to StubHub or Glyde (sexy UI by the way fellas) but in the travel/vacation industry. Watch this space over the next couple weeks for more details.

At any rate, we first contacted Braintree about 2 months ago and began a dialog about engaging their services. This included a discussion of our business model, anticipated transaction volumes, revenue projections, and the like. Given that we were not yet done with development, we did not submit a formal application with them at that time. Instead, we continued work on the items we knew Braintree wanted to see (e.g. clear communication about pricing, customer support contacts, terms of service, etc.) as well as the more core features of the site. During this time, Braintree allowed us to develop against their development gateway and occasionally asked us if we had any questions (we did not – it all appeared straight forward to us).

This week, the time came to actually begin the formal application process. Which is when we ran into problems. As mentioned above, one of the things Braintree does for its customers is handle the merchant account setup. It turns out that this was a more significant step than I thought. Once the underwriters saw our site, they declared it a high risk site and refused to underwrite the creation of the merchant account for us. It’s not clear why we were considered high risk when other sites with essentially identical business models in different industries are allowed to proceed. The message given to us is that our customer guarantee (which currently looks SHOCKINGLY like StubHub as we refine it for our specific case) was something they didn’t want to cover. But, they let us know, they’d be happy to work with us if we changed our business model in fundamental ways.

So, I was frustrated with Braintree for a few reasons:

  • The risk issue was not detected by them in a timely fashion.
  • Resolution of the issue was poorly handled. For example, we didn’t get a chance to talk directly to the underwriter to make sure they were clear on the model and risks (or lack thereof in our case)
  • The only suggested remediation was to fundamentally change our business model. I have to believe we could have perhaps explored intermediate options (e.g. holding some reserves in the merchant account) but Braintree did not make those available to us.
  • In the end, I just believe that Braintree didn’t necessarily do a good job at being an advocate for us in one of their core value propositions (i.e. setting up the merchant account)

Of course, we’re not without blame in this too. One of the great things about working in a startup is that you learn things at such an insane pace. Here are my lessons learned, hoping the future entrepreneurs might avoid some of the mistakes we’ve made:

  • Don’t under-estimate the merchant account creation process – especially in this economy with banks still being fairly risk averse
  • Always have a backup plan. We didn’t in this case, and now we’re scrambling to get another solution in place
  • Don’t let it get you down and tweet out of frustration. After all, a bad day at a startup is still better than most days in a big company.

So, I hope that didn’t come across as too whiny or unfair to Braintree. I definitely think they could have done better and hope they’ll do a better job with future customers. But I know too that most people who use them still think very highly of them. Sadly though, that won’t be with us.