Evan Schneyer of Outlaw: “Good = Love — Fear”

I’ve always been frustrated with seemingly contradictory advice from founders and VCs alike when it comes to fundraising. Some say, “Raise as little as you can” — meaning, stay scrappy, bootstrap, retain control. Others say, “Raise as much as you can” — meaning focus on hyper growth and basically fake it ‘till you make it. Dan and I have […]

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I’ve always been frustrated with seemingly contradictory advice from founders and VCs alike when it comes to fundraising. Some say, “Raise as little as you can” — meaning, stay scrappy, bootstrap, retain control. Others say, “Raise as much as you can” — meaning focus on hyper growth and basically fake it ‘till you make it. Dan and I have always leaned strongly toward the former approach, but still this contradiction irked me until one of our seed investors, Kevin Mahaffey, said, “Raise as much as you can, but spend as little as you can.


As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Evan Schneyer.

Evan Schneyer is the CEO and Co-Founder of Outlaw, a cloud-based contract platform that enables teams to generate, negotiate, track and manage contracts in a first-of-its-kind authoring environment. He’s a builder of products and teams, having started multiple successful companies over the last decade, including travel inspiration service Wanderfly (acquired by TripAdvisor). An ex-Googler, he believes that ideas are cheap and execution is everything. He loves coffee, video games, cats and Brooklyn.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I’m a serial entrepreneur — this is my 5th business, and 2nd venture-backed tech startup. As a founder, you constantly find yourself dealing with contracts… everything from fundraising to hiring to service agreements with customers — and generally in that order too :-). Fortunately, my dad is a retired General Counsel, so I grew up around this stuff and was already fairly well-versed, but something surprising happened as I gained experience with contracts: the more adept and comfortable I got with legalese and with the overall deal process, the more frustrated I became, because the more opportunities I saw for improvement. These frustrations coalesced into our “founding moment” in the summer of 2016 when my co-founder Dan Dalzotto and I really delved into the problem space together. Dan has done a lot of freelance design work in his career, so these frustrations resonated deeply with him as well, especially regarding the stress the recipient experiences from receiving indecipherable contracts.

Both Dan and I are as honest and forthright as they come, and that’s how we aim to do deals of every sort, but sending or receiving a wall of fine print via DocuSign introduces a ton of friction, polarization and suspicion, even in the best of circumstances. So we knew from the start that improving the end-to-end user experience of a deal — for all parties involved, including recipients — would be transformative in terms of reaching an agreement.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

Outlaw is an end-to-end, cloud-based platform that eliminates contract chaos to reach agreement faster. When used to the full extent, we replace the entire, manual, Microsoft Word/email / PDF / DocuSign flow. We power the wholething, from 1-click template-driven contract generation to real-time collaborative redlining & issue resolution, all the way through eSigning and even into lifecycle management & reporting.

Of course, that doesn’t mean customers must adopt the whole platform all at once if they’re not ready — in fact, several of our customers actually get a ton of value just from Draft, our dynamic templating engine. But for those who are ready for a seamless and fully cloud-based contracting experience, throwing Word out the window is very disruptive — in a good way.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Branding and product naming are incredibly important, and when your venture is still just a fledgling idea, it’s easy to get attached to a name that you then quickly outgrow. Fortunately, I had learned this the hard way on prior projects, so when Dan and I were just starting to design and prototype early versions of what would later become Outlaw, we decided we needed a working title that was suitably ridiculous to avoid any risk of this attachment. We chose Deal Master Pro 5000, or DMP5K (pronounced “dumpsk”) for short! Fast-forward a few years, and we recently just crossed 5,000 commits (!) in our codebase, so we’re still getting mileage out of our silly pre-incorporation name.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

Every startup accrues a Board of Advisors along the way — people who are available for intermittent mentorship in a particular area of expertise in exchange for a small piece of vesting equity. While it’s tempting to try for big recognizable industry names for these roles, the problem with these types of advisors is that 1) they’re frequently very short on time, and 2) you frequently don’t have any prior relationship with these folks, which really limits the engagement and value you can get from them.

We’ve taken the polar opposite approach — our advisors are people whom I’ve known for ages, love and trust unequivocally, and so I’m able to tap them on a weekly (sometimes daily) basis for genuine mentorship. Two of our advisors, Christy Liu and Jorge Trujillo, are my former co-founders from my first startup, and Christy is also my SO/partner of nearly 20 years. So while she’s technically our Marketing Advisor, really she’s my go-to sounding board for just about everything, including (especially) those dangerous existential founder questions like “Why are we even doing xyz?” I honestly don’t know whether I would have even started DMP5K — er, Outlaw — without Christy.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

I love this question — indeed, sweeping change is not always good! I think a good starting point here is to look at the potential disruption holistically, including everyone, everywhere, who stands to be affected, not just one group of primary beneficiaries. One of the most harmful concepts in modern economics is that of externalities — effects that are considered to be outside the scope of a given system. In theory, externalities can be positive or negative, but in practice, whoever is creating the disruption has every incentive to take full credit for all of its far-reaching positive effects, while disavowing any responsibility for the negative results and attempting to classify them as externalities.

So a good litmus test is simply to look at the number and severity of these so-called externalities associated with a disruptive change. If there’s a company (or industry or country) saying, “What? That thing way over there?? That’s not our problem!” — that’s a very bad sign. For instance, Facebook’s stated mission is to “bring the world closer together” — and, sure, there are countless examples of that happening. But, there’s also a global crisis of isolation and depression that comes from everyone spending hours daily looking through a curated, filtered lens of all their friends living their best lives. That mental health crisis is not an externality of social media — it’s a direct effect of disrupting community IRL.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

I’ve always been frustrated with seemingly contradictory advice from founders and VCs alike when it comes to fundraising. Some say, “Raise as little as you can” — meaning, stay scrappy, bootstrap, retain control. Others say, “Raise as much as you can” — meaning focus on hyper-growth and basically fake it ‘till you make it. Dan and I have always leaned strongly toward the former approach, but still this contradiction irked me until one of our seed investors, Kevin Mahaffey, said, “Raise as much as you can, but spend as little as you can.”

Kevin’s advice not only resolves the apparent contradiction between these two approaches, but it’s also very sound advice for any business, not just startups, to think of your cash in hand as a reserve, not just a runway. On that note, this reminds me of another tip I try to practice and would like to pass along: only take fundraising advice when it comes alongside a check! 😉

Lead generation is one of the most important aspects of any business. Can you share some of the strategies you use to generate good, qualified leads?

Well, it helps a lot that Dan is a unicorn designer, so everything we put out into the wild looks gorgeous — from the product itself to sales decks to marketing collateral. But co-founder flattery aside, in SaaS, it’s all about reviews.

Our best leads have always come from savvy prospects who do their research on the contract management software category on review sites like G2 Crowd and Capterra, and our reputation on both is stellar. To get great reviews, you need happy customers, and to get happy customers, you need to do two things in tandem. First, focus on the user and all else will follow. Second, and very related, learn to love the problem, not your solution. Together, these mantras mean 1) putting a healthy customer feedback loop in place in order to constantly gather information about what’s working and what’s not, and 2) maintaining a culture of humility, in order to constantly acknowledge and learn from your mistakes. In other words, the key to great leads is a great agile product development process: never stop iterating.

We are sure you aren’t done. How are you going to shake things up next?

Ha! I do have a bunch of silly projects in the internet entertainment space I want to create someday, but they’re all pretty small and they can wait — humor is timeless. As far as genuine big ideas, I’m 100% focused on Outlaw for the foreseeable future. I think it takes this degree of total commitment in order to succeed at real disruption, and it’s also a great feeling to go all-in on something I believe in so strongly, and not just be looking around for the next hot tech trend.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

I love HIBT. Many of these stories run the course of founders’ entire lives, or at least several decades. There’s so much pressure on tech startups to achieve an impossible rate of hypergrowth, that it’s hard (but important!) to remember that creating real value on a large scale takes time! More generally, I just find so many of these stories so inspiring in terms of founders’ grit and ingenuity. Some of my favorites are Spanx, Vice and Burton.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I try to never miss an opportunity to promote the sage wisdom from Bill & Ted’s Excellent Adventure:

“Be excellent to each other. And… party on, dudes!”

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Actually, this follows well from the prior quote. It’s my long-standing belief that love and fear are diametrically opposing forces, at every level — from individuals to families to organizations to entire cultures and countries. It’s not zero-sum by any means — it’s certainly possible to have more love than fear — but I believe that fear directly detracts from love, much in the same way that expenses detract from revenue on a P&L. So if we’re thinking about maximizing good in the world, it’s simple algebra:

Good = Love — Fear

So there are two ways to do that: increase love, or decrease fear.

Increasing love in the world is too abstract and too daunting — it’s hard to know where to start. But decreasing fear can actually be very concrete and even measurable right from the start. Whether we’re talking at a personal level with things like therapy and meditation, a local level with things that foster (IRL) community, or an even greater scope such as non-profits who aim to increase acceptance and understanding between historically hostile groups — there are literally a million different places to start.

There’s also never been a more important time for such an endeavor. Especially in the midst of a global pandemic and widespread political and civil unrest, there is so much fear everywhere we look today; it’s truly overwhelming at times.So I guess that’s the best I’ve got in the way of movement starters: if you’re looking to make the world a better place, start by focusing on ways to decrease fear.

Actually, go bigger than that: disrupt fear.

How can our readers follow you online?

For any business users who share these same frustrations around contract chaos (which is to say, everyone), Outlaw can help! Take a look at our platform and feel free to request a demo.

To follow Outlaw’s disruption journey, you can follow us on LinkedIn, Twitter or Facebook.

As for me personally, I avoid most forms of social media (see reasoning above), but I’m still bullish on long-form content, so you can check out some of my intermittent musings on Medium.

This was very inspiring. Thank you so much for joining us!

It was my pleasure. Thank you for having me!

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