Five Essential Lessons I learned as a Founder
A lot of people daydream about being a founder. Quite often, when someone hears the word “startup,” they tend to think about massive IPOs and the lifestyles of excess that make the news.
So what really happens behind the scenes? What could you possibly gain from burning the midnight oil day in and day out just so you have a shot at breathing life into an idea when your odds of success are lower than getting struck by lightning?
I’m not going to pretend I have all the answers or purport to be the single source of truth. However, here are the top five things my experience has taught me as the founder of Docstur; a document automation SaaS company with a recent exit:
The startup journey is littered with failures like potholes on Highway 680. Avoiding %$^& ups is futile so the best course of action is to embrace setbacks by learning from them as quickly as possible. In other words, the goal here is to wash, rinse, but not repeat.
I came to this realization during my very first pitch to a VC, which took my advisor several weeks to schedule. I knew I had one shot to make a good impression so I rehearsed at least 100 times. On the day of the pitch, I walked into the conference room, engaged in formal pleasantries, and proceeded to connect my laptop to the television screen. Unfortunately, it had never occurred to me to ask about the tech set up. My laptop wasn’t compatible with wireless screencasting, and as a result, I spent ten precious minutes trying to connect and was forced to pitch on my 13-inch Chromebook. The conversations for funding didn’t advance past that initial meeting and the drive back home was the longest trip of my life.
When the next opportunity, Plug N Play, called and invited me to participate in their Enterprise 2.0 Selection Day, I knew what I needed to do beforehand. I scouted the venue prior to the event, confirmed that my presentation worked in the conference room, and requested feedback from the director on how to best present to over 150+ attendees. This time around, it was a success and led to a pilot opportunity!
As a Stanford and UCLA alumni, I’ve had the pleasure of meeting and working with some of the brightest minds. However, no matter how smart a person is, their ability to work through complex challenges is also impacted by how they handle their emotions and manage interpersonal relationships.
My emotional intelligence was put to the ultimate test while managing a team consisting of six data analysts, a machine learning developer, and marketing specialist. Each person had a role, task, and deadlines. Here, the challenge came in the form of working across different countries in different time zones from India, to Bulgaria, to Italy.
I vividly recall one experience where data analysts in India were tasked with classifying the 10,000+ contracts which would become a part of the initial corpus for Docstur’s machine learning algorithm. When I checked in with the team a week later, I discovered that the classifications were riddled with inaccuracies. Our release date now had to be pushed out another week because of this setback.
Despite being frustrated, I was forced to come to terms with the fact that I was the source of the problem; no one else was to blame but me. I was working with people in different countries with different backgrounds so why wouldn’t the results also be different than what I expected unless clear expectations were set?
I ended up spending fifteen hours revamping the documentation using examples of what to look out for as each contract is being reviewed. This approach helped improve how we clustered the data in addition to the accuracy rate for the anomaly algorithm (the driving force for Docstur’s machine learning functionality). In retrospect, I would have certainly derailed the entire development had I wagged a finger at the team for something I had direct control over.
The stress you experience as a founder can hit like a ton of bricks. Work has no boundaries and there is always something demanding your attention. Perhaps a potential customer asks for an in-person demo with very little notice or maybe you have to address an urgent SLA issue because it directly impacts core functionality that isn’t working. And yet, these challenges have an elevated level of complexity because you will inevitably deal with real people with real problems.
For example, I’ve had major development postponed due to a wedding and a meeting delayed for three weeks so a partner could visit a sick relative. These issues can also strike close to home. While working across multiple time zones my sleep schedule was thrown off to the point where I developed insomnia. The only remedy was to take a few days off from work even as it continued to pile up.
The net takeaway here is that embracing the uncomfortable and unexpected allows you to maintain equilibrium and gives you the strength to navigate the ups and downs you’re bound to face every day.
For the first couple years as a founder, every fight is your fight, which means you’ll have to seamlessly jump between the world of product management, finance, legal, sales, business development, and more. Some believe that the formula for success is the ability to multitask, but the real answer lies in one’s ability to become as proficient as possible in these various parts of your company.
Each area is like a different piece of body armor. You’ll need the entire suit of armor if you want to win the war. However, it doesn’t mean you have to start off being an expert across the board since the main objective is to establish a strong foundation.
For product management, it could mean understanding how to draft clear acceptance criteria because the removal of ambiguity makes it easier for the development team to build your product. On the legal side of the house, you’ll want to understand the different types of patents (provisional vs. non-provisional), at what point they should be considered, the costs associated with each, and how the terms and conditions generally vary between each stage of investment. Additionally, you’ll want to understand what goes into a cap table, the impact investment can have on equity dilution and ownership percentage.
It’s inevitable that you’ll stumble along the way no matter how prepared you are or think you are. However, gaining this foundation did mean that I was better equipped to make informed decisions by drawing from a robust knowledge base across various areas of my company.
Not everyone is built for the same type of race. Some people are great at short distances, while others can run a marathon in their sleep. I’m the former so I stick to the annual 5k Turkey Trot on Thanksgiving. No matter what type of runner you are it’s important for you to lock into your race, keep your eyes forward, and refrain from looking in other directions. Otherwise, you may start to over analyze and waste time.
On more than one occasion, I can recall being envious of companies receiving substantial funding despite lacking a product, market fit, and/or customers. The issues seemed to be endless, but at the end of the day, I had two options in front of me: 1) stay focused and do everything within my power to move the company’s agenda forward; or 2) allow challenges beyond my control to eat away at my limited time and bandwidth. I generally stuck with the first option knowing that even if I fell short of expectations, I wouldn’t have regrets about my level of commitment to the company.
So what does it all mean? At the end of the day, the startup journey is different for everyone. Some find success, some fund frustration; some find it rewarding, other’s find it too demanding and the list goes on. However, there is one irrefutable fact about this experience — no matter where your journey leads, you will certainly grow as a person and build relationships that will last a lifetime.
Five Essential Lessons I learned as a Founder
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