Entrepreneurial Success Depends On Optimism--And Perfectionism

The following guest post was written by Millie Tadewaldt, co-founder and CEO of CakeStyle, an online personal styling company. In her previous incarnations, she taught herself to code, studied law at Harvard, was a management consultant at BCG, and helped create the Foundry at Sandbox Industries.

I recently gave a new CakeStyle team member two projects: first, create a slide for an investor deck demonstrating our strengths in managing inventory for our business; and second, create a slide for our company meeting explaining how we should improve our inventory management function. The result: confusion.

As an attorney by training (and a natural-born debater), it hadn’t occurred to me that learning to “debate” your own startup can be an acquired skill.  A necessary skill, to be sure, but something that doesn’t come easily for everyone.

Lawyers generally have very little control over which “side” they will end up on, so they have to be prepared to advocate for their client either way.  In law school, we are taught how to see the strengths of both sides of an argument, and even practice arguing both sides.  This has been the most useful skill I transferred from my legal education to my life as an entrepreneur.

There are two lenses that a good entrepreneur needs to learn to use interchangeably, and he/she also needs to learn which lens to use for which audience.  And, as I will explain, I mean “lens” in the sense of true, honest perspective, not in the sense of a slimy defense lawyer trying to get his clearly-guilty client acquitted.

Perfectionism: This is your daily working lens, used to help you motivate your team, receive guidance from your board and mentors, and define your own to-do list.  This is what keeps you up at night.  Startups are all about incremental improvements, and striving for “perfection,” though rarely achieving it.  A good entrepreneur is a perpetual critic.  She sees where improvements can be made (pretty much everywhere!), devises strategies to improve, and then isolates and prioritizes the most impactful ones. In CakeStyle’s case, this means determining how we can improve inventory management by increasing turn, more quickly identifying which SKUs are “dogs” and liquidating them in season, reducing damaged inventory rates and improving our buying function.

Optimism: This is the lens of the pitch, often used for interviews with press, recruiting new employees, getting the team (and yourself) pumped up, and pitching investors. This is what wakes you up in the morning, why you’re always excited about your business, why it’s special, why your customers love you, and how the data proves it.  For CakeStyle, this means showcasing how our inventory management metrics beat retail and ecommerce benchmarks, how strong our team is, and our ability to profitably sell or liquidate literally everything we buy.

Even if seeing both sides at the same time doesn’t come naturally to you, practice looking through each of your lenses and communicating with appropriate measures of perfectionism and optimism depending on your audience.

And, to be clear, the truth must exist in both of these lenses.  You should always be honest with the press, your team, your investors, your board and yourself.  A good entrepreneur should be optimistic and energized about her business (when optimism is warranted), but also able to clearly see where improvements should be made next.  And improvements are always warranted.

By: Millie Tadewaldt

Source: Forbes