Fear, Anxiety, & Imposter Syndrome from Starting a New Company

Acknowledging my own fear, anxiety, and doubt. Hopefully providing a guide to overcome it.

My second Year Of The Opposite is dedicated to Building and Creating.  This newsletter/ podcast that you are reading or listening to is one such creation. Last week I launched another. I launched a new startup this past Friday with my good friend Chris Strandt. I’m filled with excitement about it. Today I want to share an often unspoken aspect of starting a business: fear, anxiety, and imposter syndrome. 

MyVilla is not my first startup and by many measures I’m in a safer position to start this company than any of my previous business ventures.  I have the support of my wife, the partnership of my close friend, a modest level of financial security, and a relatively decent social standing.  But nonetheless, sometimes the fear I feel about starting this company can be almost crippling.  

Each day is a pendulum swing between exhilarating highs and near-debilitating lows of fear and anxiety. Every time we achieve a fresh breakthrough, entice another prospective customer, or earn the backing of a respected advisor who wishes to invest, the satisfaction is beyond comparison. The opportunity to share these victories with my friend Chris and my wife Laken brings a profound sense of joy that words struggle to encapsulate.

However, there's this lurking apprehension and a recurring anxiety and fear. It frequently slips in when I settle into bed at the end of the night, or jolts me awake from slumber. My thoughts spiral, racing against the silence. The worry consistently focuses on a few themes. 

A significant part of my financial resources are pledged to this venture, potentially investing or wagering between $400k to $1m of my personal resources. To some, this amount may seem staggeringly vast, yet to several of my peers, it appears a pittance. For me, it's a substantial portion of my liquid assets. 

Of course I’ve tried to make this a logical bet and I’ve run several financial models. I've strived to protect my financial security, weighing the risks against the potential for substantial gain and doing my best to protect and minimize my downside exposure.  After all, risk is the price of reward.

Amplifying my financial concern is the fact that my friend, demonstrating an extraordinary and humbling belief in me and my idea, is sharing this risk with me. He and his family are staking a considerable portion of their resources  to help build this company by my side. They stand at the precipice, prepared to share the hardship, ready to take the leap with me. They are staring into the abyss chewing glass, and ready to jump off the cliff with me in hopes that we can assemble the airplane before we crash into the ground.   The process of starting companies seems to be full of colorful metaphors that imperfectly describe the experience in dramatic ways.  

Having people invest in MyVilla generates a feeling that is unusual for me but it’s not new. Only once before have I accepted financial investment to start one of my businesses. It was a generous $10,000 loan from my supportive and trusting parents to establish my first business, a media production company. The company failed almost instantly, yet I managed to repay the loan in full and ahead of schedule. Still, the echo of that experience haunts me, a ghost from my past that refuses to fade. I have so much scar tissue from that experience that I made it a rule to never accept or solicit outside investment into one of my businesses again. 

But now that rule is being challenged. I’ve been incredibly fortunate to have several friends and mentors that are so excited about MyVilla that they are urging me to allow them to invest in the company. This is a position that I have only been in once before and it went badly. I haven’t yet decided if I will accept their generous offers to invest. The duty, responsibility and pressure that I feel to be a good steward of their money and show them a good return is a weight that I’m unfamiliar with shouldering.  Losing my own money is one thing.  But losing someone else's money seems an unimaginable and terrifying thought.

Then Imposter Syndrome sets in. Imposter syndrome is where I doubt my accomplishments and harbor a persistent fear of being exposed as a "fraud." Launching a startup is like constantly charting unknown territories. Each day ushers in a new task, a novel challenge that I've never encountered before. There's no roadmap, no step-by-step manual to follow; it's all about learning on the fly and adapting swiftly. But with this pioneering spirit often comes the shadow of imposter syndrome, whispering doubts and questioning my legitimacy. 

There is another recurrent fear, one that I'm more embarrassed to confess that is born from the shadows of my ego - the part of me that's sensitive to status and pride. What will the whispers say if I fail? It’s only been a mere 3 days since I launched the business, but of course there are several people eager to poke holes in my plan and tell me that my plan is unwise. What if the naysayers are right? What if I'm incapable of pulling this off? Will they all mock me? Will they ever vest their trust in me again? Can I shake off the social stigma associated with failure? Will my other businesses suffer because of my failure in this venture? 

In my heart of hearts, I recognize that these concerns are trivial, yet this understanding doesn't stop the fears from seeping into my thoughts. I must be honest with myself and acknowledge their presence. I'm aware that the pursuit of status is a zero-sum game. I know that if I play stupid games, I only win stupid prizes. Yet, this knowledge doesn't seem to silence the insidious whispers in my mind.

So, what quiets these negative voices? The solution is very simple. But that doesn’t mean it’s easy. The solution is working hard everyday. Rising each morning and starting my exercise. Eating healthy. Focusing my energy on tackling meaningful problems each day. Writing in my journal. Being an attentive father and husband. Each night, making a prioritized list of the 5 most important tasks to achieve tomorrow and the next morning working through that list diligently. Then doing it all over again every single day. These actions almost always silence the negative voices and extinguish the anxiety and fear. 

Because, for me, fear and anxiety are often just anticipatory worries about future decisions or actions that I know I should undertake but have yet to confront. If I maintain my momentum - every day, every hour, every minute - the fear and anxiety become overshadowed by the deep satisfaction of incremental achievements. Worry never solves a single problem today. But it can sap my energy and stifle my progress.  

In my experience, if I procrastinate when faced with intricate or challenging decisions, it tends to amplify my worries rather than alleviate them.  Usually, I would be better off if I made a decision quickly, even if it was the wrong decision, than I would be if I kept delaying the decision in search of the “right” decision. Usually the swiftness of reaching a decision is more important than the absolute accuracy of the decision itself. 

This post was hard to write.  I’ve tried to be vulnerable and honest about my fears and anxiety about launching MyVilla.  But I’m very happy to report that my joy is about 90% of my day and the fear is a measly 10%. I wrote this post because I wanted to be honest about the fear of starting a company that is seldom discussed openly.  As a “leader” I naturally want to exude confidence and self assuredness.  But there is a fear that is ever present in every entrepreneur that I have met if you can get them to open up to you and share their inner monologue. 

I want to be careful not to overlook or deny this truth. I am better served when I identify what soothes my inner fear and determine actionable steps to silence the negative voices. It's often easy to pinpoint what will silence them. The next step is committing myself to undertake the necessary actions every day to amplify joy and mute the criticism from the cheap seats, even if those jeers are originating from within my own mind.

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