Caught in the Quicksand Part 6: Failure is Not Permanent

Sad Endings & New Beginnings

After finally finding a place to call home, and hoping to catch a few moments of peace from my bad luck, I received some more bad news. [If you missed Part 1, Part 2, Part 3, Part 4, or Part 5] My cousin was found dead in his driveway after a suspected “vaping incident.” While we weren’t particularly close, we had texted a few weeks earlier about a trip he was planning to Vegas. I was very close to my aunt, and this devastated her. She had just lost her husband in 2013. My uncle was one of the nicest men you would ever meet and a fantastic human being. I wanted to be a support to my aunt, but I was emotionally depleted and my life was too complicated to take the time to be there for her the way I wanted to be. Having a second loss in the family added to the trauma I was trying to process. Any loss, big or small, added to the crushing weight on my shoulders.

The new job I had just started was off to a rocky start. The pandemic was raging, so me and about 10 others were onboarding through a digital process. This took a lot of time. Additionally, there was no business model for my role, meaning no definitive process, either sales or legal. Most of my time was spent in multiple meetings — recurring weeklys, one-on-ones, or new hire intros. Eventually, I was given the freedom to start selling the product, which was what I was hired to do, but my frustration mounted as my boss set a slow pace for progress.  He always wanted to have a meeting before we moved forward with anything. Instead of removing roadblocks, which is what he explained was his job, he created roadblocks. A lot of precious time was wasted. 

When my boss wasn’t creating roadblocks, others were created by the lack of clear definitions and scope for the role I was to play. Sales and legal processes were not clearly developed. So, I had to do as any startup founder would do and push forward and generate sales. Thirty percent of my salary was commission-based, so I needed to be selling. Overall, I was enjoying what I was doing. Having a paycheck and insurance brought a sense of security. Finally, a sense of calm was settling into my life.  

All Dogs Go to Heaven

One morning in October, I got up and went downstairs to feed breakfast to the dogs. Millie was by my side ready to eat, but Mozy hadn’t come down yet. This was very strange. Mozy was a dog that enjoyed his food and would gobble it down in 30 seconds. I didn’t think much of it at first, but it continued for several more days. By the third day, I grew concerned, so I took him to see the vet. 

After an examination and some x-rays, the veterinarian said there was a mass on Mozy’s spleen, but there was nothing that was urgent. He told me to consider surgery as an option to help Mozy. The quote for the surgery was $800 or, alternatively, for the same cost we could do a CT scan to determine exactly what the mass was. 

I had some options to consider but chose to take my time making the decision since nothing was urgently needed. The doc had given me some meds, which seemed to be helping Mozy, and his regular eating habits resumed.  So, I decided to take the vacation I had been planning since my first paycheck. I hadn’t had a break in four years — it was overdue. I had hired an amazing dog-sitter who I trusted would take good care of Mozy while I was gone. 

Hawaii should have provided me with some much-needed recovery time, but, on my second morning on the island, my dog-sitter called to let me know that Mozy took a turn for the worse and appeared to be very sick. It seemed surgery was urgently needed! I jumped on the next plane and rushed home, having only spent 36 hours in Hawaii. I spent the night with my little buddy, and in the morning, I took him to the vet for emergency surgery. I think Millie and I spent an hour or so saying “goodbye” to Mozy before the vet carried him in for the procedure.

Millie and Me Saying Goodbye to Mozy
Millie and Me Saying Goodbye to Mozy

Less than 20 minutes later, the doctor called me. His voice was steady as he said, “I’m sorry to have to tell you, but Mozy has liver cancer, and it has spread throughout his entire liver.”  

My heart sank. I listened numbly as the doctor continued with his news. “I’ve never seen anything like it before. The kindest thing to do for Mozy would be to not wake him up.” 

I was not ready for that recommendation. The silence on the other end of the phone was deafening, as the vet waited for my reply. I felt helpless. What else could I do? After what felt like deafening minutes of silence, I reluctantly said, “Ok.” 

That simple response was the end of my little buddy’s life. I had never felt loss like this before — Mozy was truly my best friend. We had spent almost every day together for the last seven years . . . and now he was gone. It took about nine months for me to work through the brain fog that comes with grief to record my feelings about losing him. I finally was able to put my thoughts on paper. My reflection on my best friend is in this post on my blog. Writing about Mozy brought some comfort to my broken heart.  Not many understand the depth of love we can develop for our pets. 

The loss of my beloved Mozy was extremely painful, and that pain was compounded when the vet tried to charge me the full price for a surgery that was never completed. The vet had only just begun the surgery, and then he decided he couldn’t do anything. He stopped there. The “surgery” lasted only minutes and required very little skill. However, he sent me a bill for the full cost of the surgery, $300 for a box with Mozy’s ashes, and several other charges as well. I fought with the vet for six months until we finally settled on the bill being 60% of the original charges. 

Egos & Exits

For a time, work was going well at Xero. Thankfully, four months into my job, I was moved out from under my first boss who micromanaged everything I did. This created the opportunity I needed to be successful there. My new manager had the same goal as I did — sales! During my onboarding process and the first few months of working, I kept track of the process and noted any inefficiencies. I analyzed the structure of the business and found what I thought was an excellent improvement to the business model. A co-worker heard my ideas and was so impressed that he put me in touch with the president of the company. Unfortunately, my boss’s boss’s boss didn’t take kindly to the new idea. It may have been ego, embarrassment, or just plain competitiveness, but instead of investigating the viability of the opportunity, he simply fired me without asking any questions first. Working at Xero reminded me why I didn’t want a corporate job to begin with, but when you need money, you have to make sacrifices. 

At this point, I had suffered loss after loss. There wasn’t an aspect of my life that had been left unscathed during this eight-year tsunami. Wave after wave knocked me onto my ass repeatedly. The key to my buoyancy during this storm was focusing on my health: exercise, healthy eating, yoga, meditation, and therapy. These are the things that gave me the resilience I needed to keep moving forward and to heal.

Ryan 2.0

Professionally, I’m on a better path. An important behavioral shift that has helped me move forward is being intentional about what things I put on my plate and saying “no” to opportunities that were not worth investing my time, energy, or resources into. I was too focused on being valuable to and helping others, that I really didn’t have the energy to take care of myself. When flying on an airplane, there is a good reason we are instructed to first put on our own oxygen masks before assisting others. 

After living on the edge of a dollar for so long, I was able to shed the constant worry of how I would pay rent or feed my dogs (thanks Reed). Meeting my basic needs was a constant challenge, and there were many times I would put off paying for things because I just couldn’t afford them. But finally, after seven years, one of my very first angel investments matured and returned 7x. This exit allowed me to stop looking for a “real” job; instead, I have used that energy to start my own VC firm. After my experience trying to work for/with other VCs, it made so much sense to start my own and do it my way.  On August 19, I announced 4F Ventures and an $8M fund focused on investing in traditionally overlooked founders of eCommerce and FinTech startups! I’m excited to be able to invest in startups again, and it feels great to do my part in creating more opportunities for overlooked founders.

Introducing 4F Ventures
Introducing 4F Ventures

I have been able to find my footing, and my life is much better today. But, it has been years since I have felt this type of calm. That is how life with depression works. There are multiple highs and lows and they come at varying intervals, speeds, and intensities. One day you’ll be celebrating your greatest career success, and the next day you will be literally homeless and penniless, especially in the career I’ve chosen. Your emotions will bounce from event to event with you — sometimes from one extreme to another. From the happiness of breathing in the fresh tropical air on a Hawaiian mountaintop, to smelling the stark antiseptic odor of the clinic as you cuddle your precious dog while he passes away. The key is to know that the ride will continue; the path will roll out in front of you, but you need to have the strength and resilience to take that next step.

Personally, I’m on a better path here too. My health continues to be good despite the pandemic, and I’m getting back to the gym which has forced me to start eating better – I didn’t break my diet, but I haven’t been eating the most healthy plant-based foods (burgers and such). I am also making sure to have balance in all the aspects of my life.I have some vacations planned to offset the hard work I am doing now in my career. I’m excited to start living the life I earned by enduring some of the worst catastrophes anyone could experience. One disaster would have destroyed some, but I had to endure and claw my way through multiple setbacks with no intervals of respite in between. From the pinnacle of my career success of building a successful company, I tumbled down a steep cliff of multiple setbacks that left me completely breathless. I have worked hard to achieve the life I am now enjoying.

When people read these stories, they often ask: “How?” As in, “How did you survive?” Reflecting on all my challenges, I have four hard-learned lessons I want to share.

Lesson #1

Suicide is never the answer. Period. I know first-hand how dark life can get. The pain can be so intense that death seems like a welcome reprieve. But, suicide is a permanent answer to a temporary situation. There is always a new day. There is always a new opportunity. There are effective ways to address the emotional and physical pain that come from depression and other debilitating life experiences. Suicide only hurts people who love you. It is selfish. While you think you will move on and find peace, what really happens is that your loved ones have to deal with the consequences and the heartbreak of your loss. Don’t ever do that to people you love.

Lesson #2

I’m sorry. I want to apologize to anyone who I was an asshole to while going through the trials of the past eight years. Because I kept getting hit with wave after wave of problems, I put up walls to protect myself and to protect others from me. I know it was hard to talk to me. I know it was hard to hear me recite tragedy after tragedy. But, believe me, I didn’t enjoy living through it. I will try to do better to let people in, but trusting people again will take some time. 

Lesson #3

Speak up sooner. It is natural to withdraw from people when life is hard. We see it in nature. Animals and insects will curl into little balls to protect their fleshy, exposed, vulnerable parts. It is human nature to do the same. What I know now is that I should have reached out for help, but I was too embarrassed. I couldn’t get myself to ask the same people that looked up to me for help. After carrying this baggage for so long, I want to put it down and leave it behind. And, if sharing my story can help anyone else who is going through their own crucible, that would make me happy.

Lesson #4

Take care of yourself. I neglected my health for almost too long, and had I not made a change when I did . . . well, it saved my life. It’s never too late to do this. I thought at 35, I was stuck looking and feeling like I did then, but I was wrong. Take the time to take care of yourself. If you don’t take care of yourself, you won’t be around to take care of anyone else. 

I also wanted to share a Checklist for Coping With Depression:

  1. Focus on what you can control. 
  2. Self-care is imperative when you are battling depression and continual setbacks
  3. While your mind is struggling, you can counteract it by strengthening your body
  4. Never give up! 
  5. Always take care of your health. Health is wealth!

If you’re struggling and need someone to talk to, my email and DMs are open for this.

[Part 7 – Follow-up]