A Series: Learning From My Epic Failures (Part 3)

Growth mindset Resilience Respect


Key Point: Timing is everything. And sometimes things happen that can best be explained as plain, bad luck. Epic Failures No. 1 and No. 2 outlined in my last couple blogs, ironically played into No. 3. When I was with the Fortune 50 Company, (US WEST), I met lots of brilliant Telcom engineers and business people. A few of them I really respected started a voice over the internet startup, and they asked me to join the team. This was essentially Skype (before Skype), circa late 90’s, and the “dot.com” world was on fire. I was being recruited by all kinds of startups, and company valuations were crazy high. Stock options/payouts and buyouts/IPOs, were the news of the day. It was a modern day gold rush, and many of the so called .coms were proven to be .cons. They were being hyped with little or no profit performance. Still, the bubble seemed unstoppable, and we believed our new company (AuraServ) was better and different than a lot of the other hype out there.

AuraServ seemed like a no lose deal. Great technology, an excellent value proposition, superb management team, funded by one of Silicon Valley’s premiere VCs, etc. I then was the COO of a technology company (epic No. 2), and had earned a ton of stock options. However, I was in my early 50’s, our girls both in private U.S. universities, Garrett still in high school. Probably not the best personal time to take a big risk. On the other hand, my due diligence determined (along with the assessment of many others I got advice from) that this was a sure bet. And, if I was going to be part of a tech startup, it seemed like now or never? The plan:  I would sell my options upon leaving my current company (a little back up nest egg). Then, with this new voice internet powerhouse, I would experience building a super company with great purpose and potentially make a financial home run, too.

Then it happened: The .com market bubble burst almost overnight and severely discounted and penalized most technology stocks, including the company I left. My stock options were now ALL under water and I had to exercise them within a time frame that was unfavorable (no nest egg and a BIG ouch). And, if you are old enough to remember that time, almost all investment capital immediately dried up. Even though AuraServ was getting customers and meeting revenue commitments, we could not get our next round of funding. Uh oh! We ran out of cash, and out of business. Over 100 employees now without work. Disappointed people I deeply cared for who believed in me. Our family investment, gone! Holy %#!*!  It took me two months without a pay check to ensure every person working for me that wanted to have a job, found one. Now, I had to recover personally. It was a miserable time for me. 

The good news with a supportive wife and family, a little good luck, personal perseverance, and hard work, I bounced back and became the CEO of another company. While the AuraServ outcome was disappointing, I was proud of the results we achieved and learned a lot about myself. I recognize how much I am a blessed and fortunate man with way more than anyone could ask for.

Personal Leadership Moves:

  1. Sometimes all the due diligence and analysis are impacted by events totally out of one’s control. Be mentally prepared that this could happen at any time. Know your risk tolerance. How much are you willing to lose? How resilient are you if the worst happens? Well run organizations intentionally manage risk. We need our personal risk plan too. Do you have yours? By the way, the flip side of risk is opportunity.
  2. The essence of purposeful living involves progressing on things that the market or other commercial endeavors cannot take away from us. Love, purpose, family, adventure, learning… Everything material goes away in time. While we all know that, sometimes we get to practice experiencing it before we die. And I believe we become better for it.
  3. Please read Dan Pink’s new book, “When,”which puts more science behind the issue of timing. 

Grateful and Resilient in Personal Leadership,


One Millennial View: In Tony Robbins’ new book “Unshakable,” (which is primarily about financial wealth), he emphasizes the importance of “real wealth” extending to being emotionally, psychologically and spiritually sound, too. Other wise words I’ve heard recently pertaining to when things get tough: “Tend your garden. No one can take that away from you.” Certainly something to keep in mind when you’re in the grind. 

– Garrett

Edited and published by Garrett Rubis