Real Leaders

5 Questions That New CEOs Must Ask Themselves

Taking a startup from an idea on a napkin to a successful business takes perseverance and often a decade of full commitment. An absolute unwillingness to quit is much more than just a required ingredient in a complex success equation.

Simply making that deep, 10-year commitment to your life’s mission will create almost immediate effects. You transform into a magnet, drawing in money, talent, and business partnerships. Of course, you must also follow through, which takes grit.

Elon Musk said building a company is like “staring into the abyss and eating glass.” I wholeheartedly agree, but consider this — you don’t need any special innate skill to eat glass, you just have to be willing to do it. The likelihood of success is far higher than published stats seem to indicate, as long as you are truly committed. The journey can be painful but it may help to keep asking yourself the following five questions.

Are people joining me?

What I’ve learned in two decades of entrepreneurship, if you are a truly committed founder, you become a magnet for talent because your passion energizes the company, shapes its culture and lands investors. When I was very much in the ideation stage of Applied Semantics, I spent time on the phone brainstorming ideas and chatting about aspirations with close friends and a few relatives. One of those long phone calls was with a cousin, Ari Barkan, an engineer who grew up and lived on the East Coast. (Ari was one of the first employees at Network Solutions, which basically ran the internet back in the day.) Only a few weeks after that call, he called me, saying he was willing to drop everything and move to California to join me.

You must ask yourself: How much difficulty am I having in signing up initial employees or co-founders? Struggling to attract talent, in the beginning, is natural, but if problems persist, it may indicate that you are not as authentically committed as you need to be. If any potential candidates turn you down, make sure you are diligent about finding out the reasons why. It will help you better understand whether the issue is your core commitment or how you are communicating your vision.

Is my commitment real?  

A very common reason for company “failure” is that the founder simply decides to move on to their next chapter of life. As an investor, one key thing I look for is evidence that the company reflects the founder’s underlying personal mission and passion rather than just a way to collect a paycheck. I need to know that the founder is committed to fulfilling the mission regardless of obstacles that will inevitably present themselves.

Commitment must even transcend the financial exit. The most strategic (read: lucrative) acquisitions involve a corporate “bet” on a committed team that can continue to build upon a mission, leveraging new resources and networks.

When Google was looking to penetrate the huge future market for the “Digital Home,” they saw in Nest an incredibly passionate and capable team that dreamed big. Google didn’t acquire Nest just for its digital thermostat. Google saw in Nest an opportunity to invest in a winning team that could pursue an ambitious dream for the future home.

You must ask yourself: As a founder, is my commitment unwavering enough to build the company to last.  

Are my values strong?

Commitment works for attracting talent and investors, but you need to immediately and continuously demonstrate it. A 10-year commitment involves a huge number of meetings, interviews, documents, emails, conversations, presentations and more — roughly 100,000 tasks from start to finish.

Amazing things happen if you can apply consistent effort over a long period of time, but a single flub can really set you back. For example, being very disrespectful to a colleague at a company meeting perhaps because you let frustration get the best of you — that single moment can have profoundly bad consequences.

You also must ask yourself: Am I adhering to values inside and outside the office and living them consistently? It’s important that you do. Character wins over the long haul.

Have I avoided the shiny object syndrome?

Ten years is also a magical number when it comes to developing expertise. While some founders bring deep industry expertise, many successful founders put in the 10 years that it takes to become the expert in your field.  

Conversely, many competitors will not be able to match you over a 10-year commitment, so the field will thin out. Computer science instructor Randy Pausch’s famous last lecture discussed the obstacles that enable the eventual winner to demonstrate their commitment to achieving success — those obstacles stop the others from keeping up!

When I started out, I worried about a growing set of competitors. Some had more money than us, others had more PhDs and better marketing. But, they all eventually seemed to be less relevant and threatening. One had very strong technology but couldn’t find product/market fit because they didn’t focus on any specific use cases. Some went through early acqui-hires. And one just spent too fast and ran out of money. A few years later, we found ourselves still standing, alone and in position to leverage years of expertise, data and technology. We were positioned to dominate a massive new market in contextual advertising.

You must ask yourself: Have I avoided the “shiny object syndrome” in the past 10 years?  Being a committed founder means occasionally saying “no” to things in the short term that take you too far from your original plan.

A process of 100,000 tasks

Some statistical analyses have concluded that startup success is exceedingly rare. For example, only .06 percent of startups reach unicorn status. At the same time, any data scientist knows that stats can be manipulated to fit your headline. The truth is for the small subset of founders who commit and follow through on the 10-year process — the chances of success are significantly higher.

Personally, I have dedicated myself twice now, over 20 years to two companies: Applied Semantics and Factual. Each has required over 100,000 small tasks that I’ve given my best efforts, each an opportunity to demonstrate my ongoing commitment. It hasn’t been easy, but both have been incredible journeys filled with learning, shared achievements and fun.

Building a company is very much about the journey, continually committing to making each step count and not getting fixated on the eventual destination. Are you ready to commit?


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