On Escape Velocity, Necessary Ruckus, & Working At The Edge Of Reason: 6 Thoughts

It’s been 10 years since Behance / 99U were founded, 3 years since we were acquired by Adobe, 2 years since we started Adobe’s new mobile strategy, and 5 years since Making Ideas Happen was published and I started investing in early-stage companies. It went fast and it went slow. I remember surfing the sea of start-up anonymity, assembling a team that developed each other into who we needed to become, worrying about making payroll, bootstrapping, fundraising, negotiating, joining/navigating/changing a big company. And advising other entrepreneurs on the same. It’s a blur full of gems i’ll never forget. Here are a few (we’ll call it part 1)…

Reaching Escape Velocity Is All About Endurance & Optimization

The Brave Captains In The Sea Of Anonymity

I’m on a flight now back from Dublin, where I co-hosted the “Design Summit” stage with friend/former colleague Jeff Veen. Afterwards, I took a stroll around the start-up pavilion where literally thousands of start-ups have a 3 foot long space to engage anyone willing to hear their pitch. I felt the energy and the pain. When you’re putting everything on the line, your business becomes intertwined with identity and self-esteem. Nothing is more humbling than everyone passing by your 3 foot space — your future. Anonymity is both a blessing and a bitch: You can make mistakes and drastic changes to your product without disappointing anyone, but only because nobody cares. I remember it well. Breaking through anonymity is a game of endurance and optimization. Enduring mistakes and optimizing via postmortems, enduring sleepless nights to process the solutions, two steps forward and one step back.

The journey of entrepreneurship is one of “relative joy.” The best you can aspire for is many peaks and valleys but a positive slope.

This pretty much sums it up in my experience. Know that the roller-coaster is normal, and all you must do is aspire for a positive slope (in the mathematical sense).

Innovation Happens At The Edge Of Reason

Rational thinking keeps us where we’ve already been. Yet, even with this knowledge, we seek to employ and invest in people who are totally rational. The greatest products I see these days are made by teams willing to consider old problems in new, seemingly irrational ways. AirBnB was clearly an idea at the edge of reason, as most VC’s couldn’t even imagine opening up their homes to strangers. Both entrepreneurs and investors must build teams that increase the odds of working at the edge of reason. The solution in one word: Diversity (Diversity = different personalities, genders, backgrounds, educations, experiences, nationalities/ethnicities, etc… Diversity shouldn’t be a biological checkbox, it is more nuanced than that.). The best way to increase the odds that your team will see things you don’t is to assemble incredibly different incredible people.

This is a classic flaw of many VC firms and why I dislike “angel groups.” The worst investors and entrepreneurs are probably the most rational and reasonable — and likely to work with people most similar to themselves. Groups are liable to make us too rational, especially when the constituents are too similar. If your team trusts each other enough, you shouldn’t want or need consensus. Sure, you should seek consensus as a process, but don’t require it to proceed. Debate with smart people you respect is incredibly productive. You need to work with an eclectic mix of all-stars that are willing to be a little irrational and have conviction at the edge of reason.

If you avoid folks that are polarizing, you avoid bold outcomes.

In a related point to building a diverse team, you also must learn to tolerate some necessary ruckus. There are a number of people I have hired over the years whose references included some warnings. Never compromise on ethics or integrity. But, on the other hand, don’t aspire for a team of peacemakers. Great creative minds have their demons (conflict is an ingredient, it’s part of the package). Engineers ahead of their time are intolerant of engineers and business practices behind the times. And within a large company, leading change requires a willingness to defy the party line (being a little aggressive/impatient is a feature, not a bug).

A strong culture tolerates some necessary ruckus. Over time, you’ll learn that shaking things up keeps things going. As you’re building (or investing in) teams, don’t try to keep the chemistry too clean. Creating something from nothing is a contact sport. It’s messy for a reason.

Feeling entitled is always a losing strategy.

There’s no bigger red flag than a leader/entrepreneur that feels entitled. It causes you to stop hustling, and fools you into forgetting the crucial role that timing and external circumstances (and people) played in your success. Once you feel entitled, you stop mining the circumstantial. It causes others to resent you, and you start to complain rather than be inspired by problems. I’ve seen a few careers evolve into this, where one suddenly feels that a lot of work is “beneath” him or her. Feeling entitled is always a losing strategy. You stop winning once you believe you deserved what can only be the result of good luck and hard work.

Don’t feed greed.

This is a simple but important lesson. When you work with people that are always angling for more, you’ll learn that they are never satisfied. I respect employees and investors that negotiate to get what they deserve. You always should. But there are some people that aspire not for their fair share but for an endless share. Beware of people that will feed themselves extra at the expense of others getting what they deserve. These people are toxic, and they don’t value the collective health of the team. Most leaders are pleasers (and I admit, I love keeping people happy), but you can’t feed greed. Doing so always backfires.

The science of business is the things that scale, the art of business is the things that don’t.

Art is special because it doesn’t scale. Art inspires us in inexplicable ways, because it is real, unique, and personal. These same forces make a business special, but they don’t teach them in business school. And they defy conventional wisdom. Why would an eyewear manufacturer make limited edition stationary or make-a-snowman kits (Warby Parker)? Why would a fast-growing food chain engage local artisans for each store they open (sweetgreen)? Why does a massive tech company deliver kittens (Uber)? Why does a guy with millions of followers take time to personally respond (Gary Vaynerchuk)? One by one, each action is “unnecessary” and quantitatively immaterial (and arguably unwise). But collectively, it is all that distinguishes you from being a commodity. These are the gestures that build relationships between people and entities.

Design is the little things that make a big difference. In this sense, great entrepreneurs are designers. They compete against incumbents not with better prices or bigger marketing budgets, but with the art of business — the stuff that doesn’t intuitively scale. Don’t optimize the art out of your business. Seek and sustain the little things that make a big difference.

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