Success Feels Like Failure When You’re Going Through It. A Solopreneur’s Origin Story.

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I remember overhearing a successful man say, “success feels like failure when you’re going through it”. Whether he knew it or not, that man was talking to me.

You see, I left the corporate world after the 2008 market crash, where like many, I lost half of my retirement savings. That loss made me rethink my life’s trajectory. I was shrinking my goals and dreams to fit my salary while I saved for my future in the wild market casino. It felt like sh*t. I would jump at the first opportunity to escape it.

A couple of years later my opportunity arrived. My close friend and I started a craft soda company to kick off my self-employment path. After 5 years we built the local brand, Alameda Point Craft Soda Co. However, for the company to take the next step, I had to take my salary off the books. So I left in 2015 to strike out independently. Hello world!

To my surprise, I quickly became a struggling brand and web design solopreneur. In over three years of freelancing, I failed through three business pivots and countless iterations in trying to find a product market fit. Yet I did not want to give up on my dream and return to my old miserable corporate existence.

I wanted to be able to support my wife and buy a home for us while serving people online. We would create a lifestyle of travel to make sense of not having children.

The thing is I was not making enough money, it was inconsistent, and I was dipping into our home savings regularly. Further compounding the problem, home rates had exploded in the San Francisco Bay Area. The timing couldn’t have been worse to buy a home.

I also realized that my service was a commodity and I was not making a real impact in people’s lives. That meant I was moving farther from my dream, not serving anybody, with every failure and passing day.

To make things worse, I felt terrible because my wife believed in me and I felt like I was letting her down in secret. I felt even worse about the situation because she trusted me to be “the man” in the relationship, but when I lost my partnership in the craft soda business we made a sacrifice to temporarily move into her mother’s house to save. Yet, I was depleting our home savings. The future was cloudy. I was scared. Worse yet, I felt like a failure as a husband.

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After a while my wife began to show signs of depression and hopelessness. My guilt began to grow louder than my fear. One day to make her happy, I planned a 3-week trip to San Miguel de Allende in Mexico. I wanted her to touch her future and feel hopeful again. I further dipped into our home savings. In my mind I was buying time and I would “figure it out” and make this consulting venture work and she would come around.

While on the trip she expressed her feelings of doubt and unhappiness. For the first time, our short three year marriage was starting to show cracks.

Emotionally charged, I rushed back to our Airbnb, jumped online and researched for growth hacks like a mad man. I ended up paying for a $2,000 online membership for ‘stock option puts’ hot tips. I was denied access for options trading at Ameritrade due to inexperience, rendering my subscription worthless. I lost that money in a blink before we even returned.

I’ll never forget the night we returned from the trip. We got home exhausted around 10 at night. We walked back into our reality at her mom’s house. She dropped her luggage at the foot of the front door. The house was cold and dark. She walked directly upstairs to our room. I quietly organized downstairs. I called for her and did not hear a peep. I immediately sensed dread. I started to hear the light hum of the refrigerator. With every breath, I felt the weight of the world on my shoulders compound.

I made my way upstairs. When I walked in I saw her in the darkness staring into space. It was dead quiet. I said, “honey are you okay?” No answer. I said “honey, things will get better”. Then she began to cry. I held her as she sobbed uncontrollably in between dry-heaving for what felt like hours.

The years of “being in transition” and disappointment finally broke her. While we had a big vision, our reality was that we were a freshly married couple living at moms. That night my tears didn’t matter.

It was one of the worst days of my life. It was clear I had to do something different. I felt like giving up and getting back to the “security” of a job with benefits.

However, a month later, a chance invitation changed everything!

I was invited to a financial workshop and I met some good people. They taught me the rules of money and how they applied to the most misunderstood of financial instruments: life insurance products.

The next day I brought my wife in and they shared with us how we can protect our money against market loss, future taxes, running out of money and getting sick. Wait! Isn’t life insurance all about the benefits after dying?

We learned about tax-free retirements, becoming our own bank, and personal private pensions that can be created with select insurance companies with a specific product structured properly. Life insurance had evolved into something sexy! Definitely not your grandpa’s “death insurance”. It was like the new life insurance that paid while you’re alive.

I remember the excitement vividly as if discovering a secret that everyone should know. During the meeting my wife and I would look at each other and we’d ask two often heard questions… “How come we never heard of this?” and “it sounds too good to be true!”

Yet, it was real and we were now informed.

The following week, we sat with our new financial planner friend and were able to leverage what was left of our home savings and our retirement accounts. Suddenly, our financial future was not just a pipe dream. We moved our money into the right vehicle.

These good people shared their crusade to help families and inspired me to look at serving people at a greater level.

One day while I was deep-diving into the world of no-risk financial products. I realized that there were specific policies that served the unique needs of solopreneurs.

Then it hit me like a ton of bricks!

I can share this with fellow solopreneurs!

I can help this overlooked market with risk-free financial plans so that they can have a clear map to their vision boards.

It quickly evolved to my core belief that solopreneurs should have the same financial access as wealthy executives; To offer the same access that banks and corporations enjoy in order to level the playing field.

My plan was to use my online marketing skills as a vehicle to reach self-employed professionals that are looking for a “benefits package”. One that fits them like a glove, one that they own and control — not an employer, not the government. But there was still a problem…

The organization I was with had a system that focused on my warm market and recruitment. My plan was to focus on solopreneurs. I would offer specific products customized to fit the unique needs of freelancers. I did not want to confuse them with partnership opportunities.

It became clear that I would lose the support of my leaders if I built my own online system focused on a specific market. I would be rendered “uncoachable”.

I was so frustrated and began to grow apart with the organization.

Which led me to research firms and agencies that would have access to the same products and would support my vision. In the end, I landed on the perfect organization that believed in my cause.

So that gave me the ability to focus on the market and delivery mechanism.

I soon discovered websites were dead and online sales funnels were the best way to deliver value to my market.

I’m currently building an online tool called the Financial Map Generator. Where a solopreneur can anonymously detail what freedom means to them, enter where they’re at financially, where they want to go and by when. Then out comes a no-risk financial map with protections and guarantees. If they move forward, a licensed financial planner works with them and the insurance companies to execute it.

I’m reminded of the wise words I heard years ago. At the time my failures felt like personal limitations. But how true it is that the path to success often feels like failure.

I went from being lost financially while navigating through solopreneur failures to discovering a new vehicle I can share while having a crystal path to our dream home. It was like setting GPS navigation instead of winging it at every stop light.

The new journey has started for me. My wife and I have personal private pensions, income protection plans and are set to open tax-free retirement plans. So that means our home savings is protected and can only go up, never down.

I am starting to make money and am making a difference in my fellow solopreneurs lives by connecting their vision for freedom to a sound financial map.

I wake up every morning with purpose. I am financially responsible and I feel good about that.

And best of all, my wife smiles more often.

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