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