Q&A with an Outlaw

In his recently released and hopefully soon-to-be-widely-influential book Angel, expert investor Jason Calacanis instructs novice angel investors to ask founders the following four questions in pitch meetings. As a founder, I thought these simple questions were immensely helpful in clarifying my vision for my current startup, so figured I’d publish my own answers here for whomever cares.

1. What are you working on?

I’m working on Outlaw, a SaaS platform that reinvents the end-to-end contract process, from legal template authoring to document generation to negotiation to signing. Outlaw includes a “term sheet” or “cover letter” layer on every contract, which massively improves the user experience for both sides and ultimately helps people close deals faster in plain English.

2. Why are you doing this?

I’ve dealt regularly with contracts of various types for almost 15 years now, and the process infuriates me every single time. With my accumulated experience, and being the son of a corporate lawyer, I’m reasonably comfortable with contract negotiation, but I still find it maddening and utterly absurd.

Think about it: we’ve all accepted it as standard practice that in order for two people/organizations to actually move forward with a business relationship, the final step in our negotiation involves being forced to switch out of English (where our dialog began) and into a different dialect! Legalese is an esoteric and verbose language in which likely only one side, at best, is halfway conversant, at most. If either of us has questions, we’re both forced to engage extremely costly linguists who are fully fluent in this obscure tongue. These translators also typically assume that the other side has nothing but nefarious intentions and therefore counsel us to proceed with great caution. We then wonder why so many deals explode, even though both sides embarked on the process with legitimately good will.

I know that the happiest and most productive working relationships are founded on mutual trust and understanding, not hidden loopholes and gotchas. So I’m working on Outlaw to demonstrate that truth.

3. Why now?

I’ll unpack this into two parts: 1) Why now for me and 2) why now for the market.

Outlaw’s timing is right for me because I’ve been thinking and talking about this problem for a long time, I’ve fully recharged mentally, emotionally and financially from my first startup (Wanderfly), and I’m ready to jump in again and give this my all. It’s also the right timing for me because solving this problem entails bringing an unprecedented degree of seamlessness to the user experience of a contract negotiation for both parties. While this “solve the entire problem for everyone involved” mentality has always been my approach to building software, a number of key services and frameworks have become widespread just in the last few years which have dramatically reduced the cost and time of development for this type of product. To put it more succinctly (but also more technically): React, Webpack, Firebase and Node have made creating Outlaw an absolute joy, whereas even just 5 years ago, it would have been much more of a slog.

Outlaw’s timing is right for the market because a combination of economic, cultural and technological factors have led to an ongoing explosion in the number of new startups and SMBs. Everyone is starting companies these days, and every one of these companies needs to work with with partners, customers, employees, vendors and investors. Every one of those relationships needs a contract, and every one of the people generating, sending, negotiating and signing these contracts feels the Kafkaesque pain of the process.

The truth is, our contract process has barely evolved at all in the last 100 years. DocuSign helps a little, but come on people — we can do much better.

So it’s no wonder that when I tell people what I’m working on, the most common response is, “Oh my God — THANK YOU!”

4. What’s your unfair advantage?

(Sorry for the lack of humility here, but this question is kinda begging for a dose of startup founder delusions of grandeur, so, here it goes.)

First off, my co-founder Dan Dalzotto and I are uncommonly good and scary fast at product development. The two of us alone designed and built the first version of Outlaw, in its entirety, faster than a bigger company can even get a single product feature like “mobile signing” into its dev roadmap for next year (yes, Outlaw includes mobile signing, duh). This combination of agility and quality does set us apart from incumbents, but it’s also arguably cost of entry for startups these days, so this is only one piece of the story.

Our real unfair advantage, the thing which can’t be copied and which sets us apart from incumbents and other upstarts alike, is that we see the world differently.

We recognize that the true goal of a contract is not a paper Agreement (capital ‘A’) which will get filed away after signing and never looked at again. The true goal is an agreement (lowercase ‘a’) — a lasting state of mutual intent to work together.

Outlaw may look, on its surface, like a breath of fresh air and a revolutionary step forward in contract drafting, term sheet generation and structured document modeling. And from technical and design perspectives we’ve had a blast tackling all of these mini-challenges. But really, Outlaw is about helping our customers get to yes and stay there.

Dan and I understand that winning in this space means focusing on the end-to-end user experience of agreement, or more colloquially as we say on a daily basis, making deals! In this light, we see that we don’t need to make the process delightful for our customers, because closing a deal is an inherently delightful experience. We just need to prevent the contract process from destroying the delight that’s naturally present in dealmaking.

We called our product and company Outlaw because we think the maverick, “challenger” brand image will resonate in the startup/SMB market, especially in the staid legal contract space. And we picked up the domain name GetOutlaw.com because it’s an accepted convention in startups to prepend your obviously unavailable single-word-domain with a call-to-action until you have the cash to drop on a 6-letter dot-com.

But GetOutlaw isn’t just a CTA to use our product and fix your painful deal process. It’s also an imperative to this industry, for ourselves and on behalf of our customers:

Get [the fuck] out, law! We’re trying to close deals. We’re sick of looking up words like “pursuant” and we just want to get on with doing the work.