A Critical Attribute for Every Successful Founder

I’m sure we’ve all heard the term “blind spot” before. Whether in business or your personal life, it’s usually a jarring experience when someone refers to one of your own blind spots. Typically, the term comes up when you’re struggling with something and a “coach” or friend points out that it’s a blind spot for you.

The term has many names such as unconscious bias, weakness, fault, oversight, etc. But the optimistic and most useful way to look at it, in my opinion, is to label it self-awareness or a lack thereof. When I think about a personal blind spot of mine, it’s usually in a negative fashion as a personal fault. If I think of self-awareness and not having it in a particular area of my personal or business life, it’s a skill or attribute I can learn or improve upon.

Self-awareness is the single greatest attribute any successful founder can bring to the table.

Self-awareness is absolutely critical for any successful entrepreneur. I’m normally pretty adept at it in my work and personal life, but sometimes I fail. And when I fail, it’s an epic fail. The concept of Sage was one of those times where I really just couldn’t let go of a thought. The thought was “I can do this myself”. How did that thought manifest itself in my own founder’s experience, you ask?

Determining What is Realistic

The idea for Sage came to me about 7 years ago. I was in the midst of tax season, struggling with procrastination doing my 2014 income taxes. It was the first year I’d gotten stock as part of my work compensation and I was completely confused as to how to account for it in my return. Turbo Tax was telling me one thing, but the way I was reading the tax law, it was completely different. Turns out the tax law was right and Turbo Tax was wrong. I wouldn’t discover this until several months down the line when I was paying and accruing penalties. Why hadn’t I gone to a CPA to get help?

The reason was I thought I could figure it out myself. The way this manifested was me looking around for the answers when I had time, browsing Yelp to try to find a local CPA that I could make an appointment with, going to H&R Block with not enough information for the tax preparer to help me, etc. I didn’t realize I was incapable of solving this problem with my current resources — a general lack of self-awareness.

The story has a happy ending, however, because out of this smoldering pile of ashes arose the concept of an advice platform where I, as a person in need, could go somewhere with my “simple” stock question and get a knowledgeable CPA to answer the question for a small fee. Heck, I’d even take the answer from a layperson with the requisite experience filing her own taxes. I worked through many brainstorming nights, honing the idea, figuring out some of the gotchas, doing a cursory assessment of competitors, etc. At the end of the day, I had a good plan for what I wanted to build.

Self-awareness Fails Me Again

Here is where my founder journey came to a grinding halt. Why? The answer is a conglomeration of things but boils down to hubris, a very strong technical background in computers and computer science, a love of technology, an overestimation of my free time, a lack of organization, an inability to prioritize life responsibilities…I could go on. But really, it all boiled down to the fact I wasn’t practicing self-awareness, assessing what I was good at, what I could personally accomplish given my limited resources of time and knowledge, and where I might need help.

I managed to convince myself that I could code up an MVP and launch the platform myself. At the time, I was thinking mobile was the way to go. This meant learning Swift, understanding things like model view controllers, etc. etc. I won’t go into much detail, but my efforts included things like attending WWDC on my own dime ($1500 ticket), buying several books on coding in Swift, several fits and starts on creating the app, a few attempts at modeling everything out in a simple wireframe builder and ultimately, back burning the entire thing as life, marriage and kids crept into my open free time.

I’m sure all of us go through things like this at varying times in our lives. The real trick is spotting it quickly, figuring out how to fill your own deficiencies in time, knowledge or relationships with complementary pieces, and doing so as quickly as possible. When The Lean Startup, or Nail it then Scale it talk about iterating quickly, failing fast, or pivoting, they shouldn’t just mean your app concepts. It’s also, even more importantly, necessary to do this in your mindset, your way of thinking, and your flexibility in finding another solution when you aren’t able to do it yourself.

Next up, I’ll discuss the conglomeration of events that got me from floundering inaction to being on the precipice of a full heavyweight MVP launch in a matter of three months. After spinning my wheels for the better part of seven years, things come together to get Sage off the ground.

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