The first blog post for a company is usually a great time to write about who you are, your background, and how you can help the reader.
I decided to take a radically different approach. In fact, I'm breaking all kinds of rules. This post is far longer, more personal, and more vulnerable than anyone should post. I chose to do this as its a very authentic look at the kind of entrepreneur and coach I am. In the summer of 2020, during one of the most challenging periods of my life, I wrote an incredibly honest and excruciatingly painful post about my entrepreneurial journey. I’m including it here in its entirety in an effort to illustrate two things.
1. Entrepreneurship is insanely difficult. Pain and failure are part of the journey. You are not alone in the mistakes, setbacks, and failures. I know what it's like to walk the difficult path and put everything you have into your dream. My biggest mistake, however, is my second point.
2. Due to my own arrogance and ignorance, I took everything onto myself throughout my journey. I did it the hardest way and made so many avoidable mistakes. This meant the journey was so much more costly than it needed to be. It was only after I connected with an incredible executive coach that I got healthy and started to run my business instead of my business running me. I paid dearly and unnecessarily for the success I’ve attained.
Life is too short and hard to make all the mistakes yourself. There is a certain sense of hustle-porn associated with startups and entrepreneurship that mythologizes and idealizes the entrepreneurial journey. I’m choosing to be excruciatingly transparent because, unfortunately, I know chances are high you have seen failure, pain, and trials on this journey too and I want you to know you aren’t alone.
Spoiler: I’m in an incredibly healthy place now, and my life feels almost too good to be true. Read on, and I'll talk to you at the end of the post.
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My Entrepreneurial Journey
6/23/2020
I believed I was a stronger person than I turned out to be.
I’ve always had ample self-confidence, competence, and grit to get me through whatever threat I was pitted against. My parents immigrated to the US in 1989 with two suitcases, four kids, $50 to their name and a dream. I was the second eldest of what will eventually be seven kids. I was the “responsible” one. I helped take care of the younger siblings, stayed in school, did as I was told, and got into just the right amount of trouble. Immediately after turning 18, I moved out to be “my own man.” I worked multiple jobs while struggling through college. I punched way above my weight class and married a bright, creative, and angelic beauty named Maryana. I started working my way up the corporate ladder. With help from Dave Ramsey, we paid off all credit cards, student loans, and car payments. We were debt-free (aside from our mortgage) in 2010 and began to dabble in rental properties. I did all the things a conscientious adult does.
In the workplace, I was the youngest member of every team at every organization, without fail. I had a high school education, an impoverished upbringing, and no semblance of a social network to open doors for me, but I wasn’t deterred. With reckless abandon, I threw my focus, energy, hours, and youth into my career. I worked my ass off, nailed crucial interviews, and was promoted. Often. I was a Call Center Corporate Trainer before I could legally drink. I became the Director of Project Management at a Healthcare company at the age of 24. Starting consulting on my own by the age of 26. Started my first scalable business at 28.
That isn’t to say I had a comfortable life; On the contrary, I got knocked on my ass. A ton.
English was a new language, so I did poorly in school and was bullied severely. Kids did awful things, like kick me when I was at a urinal to see if I would pee on myself. I got fired from my first job in 2004, second in 2005, and got laid off during the 2009 downturn. My Dad got laid off, and I took on all of my parents' foreclosures and legal battles. I bought my parents a home on my credit and coordinated their move from Florida to Oklahoma. Countless catastrophic work failures, one of which culminated in an intense 187-hour frenzy over 2 weeks (my team actually slept in the data center). Due to my workaholism, I was separated from my wife in 2012 and almost divorced. After reconciling, we struggled to have kids. We miscarried our first child while traveling in Tennessee on a work trip. We miscarried our second unborn child while in Geneva, Switzerland, and were rushed to the hospital two days into our 14-day Europe vacation. That last one was particularly devastating.
Objectively, I didn’t have an easy life. But the challenges, setbacks, and punches hardly deterred me. As soon as I was knocked down, I got back up. I was exuberant, optimistic, and determined to let nothing stand in my way. My difficult and poor upbringing just drove me to internalize a mantra deep in my core. I was going to change my family legacy. I was going to be the reason my family doesn’t suffer and go without the way I did.
In 2013, my brother, best friend, and I launched our first startup, Job Pact. Simply put, it was Match.com for job candidates and hiring managers. For the first 16 months, I worked full-time as a Project Manager during daylight hours and then on our startup evenings and weekends. I worked Monday through Sunday, averaging 65 to 70 hours a week. I dropped my hobbies, consumed every business book I could find, and slowly began to lose touch with close friends. I wasn’t blind to what was happening. In my mind, this was the cost of success.
In 2015, my dad was diagnosed with Stage 4 gastrointestinal cancer. The prognosis was dire. I firmly stepped into the family patriarch role. I handled his hospital visits and financial and legal affairs even while jumping full-time into my startup. Job Pact was struggling, but I was determined to make it a success. I *had* to make it successful so Dad would know the family was taken care of. It was my fuel.
Despite investing all ($50k) of our savings, an early licensing deal, and lots of positive “feedback,” Job Pact was losing steam. We had ignorantly chosen to build marketplace software, so we needed a massive amount of candidates in our system to entice hiring managers. We needed substantial job postings to bring in those candidates. Our bootstrapped startup stood no chance. In early 2016, we started pivoted to focus on our resume matching engine, which excelled at pairing resumes to relevant job postings. We licensed Job Pact to another struggling entrepreneur and put all our attention on testing the viability of this matching engine. We called it Hire360.
Silently but steadily, Dad’s cancer spread to other organs. Cancer, in all forms, is ruthless and relentless. Stomach cancer was no different. Eventually, my dad could no longer physically eat and started to wither away, slowly starving to death in front of his family and loved ones. As his body became more frail, I told myself I needed to become more steady, stable, and strong. I was going to be the rock for our family. Eventually, his body refused water and even ice chips. In a final stroke of cruelty, the dehydration took his mind. He became delirious and incoherent. He finally passed on March 1st, 2016. It was a relief, I told myself.
I didn’t have time for grief because I was the one handling every detail of the funeral. I wrote his obituary and officiated the service. I gave the necessary handshakes and hugs. I accepted condolences graciously. I eulogized the man who meant everything to me. Then I cremated him, and I went back to work. I didn’t take any time off aside from the funeral. I thrust myself into the startup with a feverish intensity. I needed to take my mind off of the loss; at least, that’s how I rationalized it.
By 2017, we started to receive overwhelmingly positive feedback on this second venture, Hire360. It was an incredible system that did proactive outbound recruiting for a hiring manager, and, more importantly, it worked. Almost. We were able to identify and proactively reach out to passive candidates quickly. But then Hire360 ran out of candidates. Employers jumped on our platform, successfully hired some of what they needed in 2-3 months, and then dropped back out. It was a constant revolving door of onboarding clients and then losing them. We needed a deep partnership with a big player like Monster, Dice, Careerbuilder. For that, we needed far more capital and influence.
We raised a small $130k friends and family round to keep us afloat while we raised money a series seed round or fixed the leaky customer bucket. All that money went into the product instead of our pockets. At this point, we had been bootstrapping for 3+ years and we were all under crippling financial strain. I had sunk in the last $30k of my savings over a year ago, and we were accumulating credit card debt rapidly. This is when I finally became aware I was fraying at the edges.
I developed debilitating insomnia. I would crash into bed around 11pm, my body completely exhausted, but my mind would ruminate with anxiety, worry, and shame. I had mid- and late-onset insomnia, which meant I woke up at about 1:00 am and couldn’t go back to sleep. I would lay for hours, spiraling into deep depression. I started to get out of bed at about 3:00 am, shower, head to the office, and work until I thought I couldn’t stay awake. At about 7:00 am, I got tired enough to attempt a few more hours of sleep. That brought a typical day’s sleep to 4 to 5 restless hours.
When my wife told me that we were pregnant with our second child, I collapsed and wept. Bitterly. I couldn’t imagine one more thing on my plate. I couldn’t imagine adding a beautiful but needy soul into a world that seemed to be closing in around me. Or how I would function with even less sleep than I was already getting. It was one of the rare moments I allowed myself to indulge and just feel sorry for myself; I ugly cried. After an hour or two, I was done. I didn’t actually process it, opting instead to cram these additional worries into the same room I kept all my other anguish, dread, and humiliation. I composed myself the best I could and went back to work.
Raising investment is a full-time endeavor and requires total energy, concentration, and focus. Yet, I was the only revenue generator for our fragile startup. When I let off the gas pedal, we all felt it instantly. I split my non-existent energy the best I could and juggled pitching investors, courting prospects, supporting clients, and attempts at being a present father to my son, Lincoln. I did them all poorly. In an act of desperation, I made more cold calls than I had ever had in my life, topping over 2,000 cold calls in December of 2017. It bought us some time, but I was perilously past burnout. We were a zombie startup. We were obviously dead but kept shambling on. My second startup was officially a failure.
My only solace was a group of founders who met every other week to discuss entrepreneurial life's trials, tribulations, and tragedies. We sympathized with the defeats and celebrated the victories over beers and foosball. One of those founders, Chase Curtiss, connected us to someone who was looking for some development work. We landed that project through Chase’s heavy endorsement and God's grace. The contract brought in $54,000 and saved us. It was a sliver of hope. We spent 7 frenetic weeks building and blew away expectations, which enabled us to land more projects. We had inadvertently become a software development firm. In April of 2018, 360 Labs was born.
Though we weren’t successful at launching our own companies, we had learned so many hard lessons and we were incredibly adept at building software. We began hiring to keep up with demand. I was still mired in paralyzing anxiety, depression, and insomnia, but we had a glimmer of hope. I brought in project after project. My technical cofounders knocked out project after project. In 6 months of operations, we brought in $486,070 of revenue.
Our largest client began to hint at his interest in acquiring our company to “join the family,” as he put it. He owned dozens of companies and was interested in us running one of his SaaS companies, which his best friend wanted to exit. In November of 2018, he made an offer we couldn’t refuse. It would give us the financial security and stability we went so long without. We accepted and moved our families up to Minneapolis where I stepped into the CEO role of a 20-year-old startup hemorrhaging money with a flagship software plagued with outages, downtime, and catastrophic failures.
The software had catastrophic downages 5-6 times a month. I took every call, complaint, horrible conversation, and piece of blame. In the first few weeks of my takeover, our largest client, responsible for 80% of our revenue, said he wanted off our platform. He had had a relationship with the previous CEO but not with me and was utterly done with our shitty software. I panicked, wined, dined, begged, cajoled, and promised anything and everything, which eventually bought me a one-year contract extension. I leapt into swift action. I sold off legacy products, replaced 80% of the staff, shut down remote offices, pandered to our clients, and spent long, long nights working with the team to stabilize the platform. I shielded the team at the expense of the last shred of mental health I had.
To everyone publicly, I was a success. I was 33 years old, running a multi-million dollar technology company with almost 50 employees and contractors. I looked and acted the part. But inwardly, I deeply resented any thought of people thinking I’ve “made it.” The truth was my insomnia was at a fever pitch. I was on tons of medications and antidepressants. I was drinking an alarming amount every day. I worked an immense amount of hours and accumulated all manners of abusive beliefs and thought patterns. I struggled with dark thoughts of death and suicide. My theory on life was this: Life is fucking hard. You have to fight through setbacks, misfortune, and shit, and in return, you get pockets of joy and happiness.
My saving grace was that I was finally financially stable enough to hire an executive coach. She very quickly became my lifeline and counselor. Months in, I confided that I’d been having really dark thoughts, thoughts of death. She uncompromisingly pushed me to tell others in my life about my struggles. When I finally told my wife, I prettied it up a lot. I told her there were times I would welcome getting hit by a bus, but I’d never kill myself. I’d never do that to my family. She wasn’t convinced and in her infinite wisdom, she asked me if I thought that everyone who killed themselves did it sober. That stopped me cold. I couldn’t fool myself anymore. I finally woke up to just how broken I was. I needed help.
I went on a 30-day sabbatical focused on processing the grief and trauma of the previous 6 years. During 6 year period, I lost my father and both remaining grandparents, had two kids, developed crippling insomnia, anxiety and depression, alienated myself from all of my non-work friends, failed two back-to-back companies, ruined the friendship with my best friend and cofounder, sold a company, lost my brother as a cofounder, starting drinking an alarming amount, forgot how to have fun, fantasized about my death, and contorted my life philosophy into one of pain and misery.
I believed I was a stronger person than I turned out to be.
That’s not an admission of weakness. It's an admission of ignorance.
Here’s the tragic thing. I worked with an incredible team, came home to a loving wife and family, and had a genuine connection with other incredible founders, and yet I never shared my inner-most thoughts. I never shared what was really happening inside my head. I was afraid to tell people how bad things really were. None of the reasons make sense now, but they felt natural to me then. I didn’t want to jeopardize my sterling reputation. I was terrified they’d force me to quit. And I’m not a quitter. So I kept it in.
I should have asked for help a thousand different times. But I didn’t.
I thought I could handle it on my own. But I couldn’t.
I thought I was indestructible. But I wasn't.
We aren’t meant to tackle all of this on our own. I was never meant to shoulder all those burdens on my own. There’s no way we can go through life without constant support. Without relying on those who love you. Without properly grieving. Without acknowledging the loss along the way.
There is no such thing as a self-made man or woman. That’s a myth. It’s a tempting but nefarious lie. You weren’t meant to do this on your own. I’m writing this with this new realization.
With the help of those around me, I am far stronger than I ever realized I could be.
…….
I’d feel remiss if I didn’t also stop and say something here.
If you or someone you know is going through anything close to what I described above. Please, for everything holy, reach out to me. Reach out to someone. Talk to a counselor. If you have no clue where to find one, let me know, and I’ll connect you.
Also, please check out The Entrepreneur’s Guide to Keeping Your Sh*t Together: How to Run Your Business Without Letting it Run You by Dr. Sherry Walling. You’ll thank me.
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I wrote and posted this blog post publicly while on that 30-day sabbatical, and shortly after, my business partner and majority owner decided to sell the company. Candidly, he read this and was immediately (reasonably) concerned for me. I had fixed enough of the company's significant issues, so we navigated it to be acquired by the same customer who wanted to bail when I took over. It’s now 4 years since I wrote that blog post and as I reread it, I’m blown away by how dire things were then and how far I’ve come now. Since that time, I took a lot of time off, traveled, helped my friends with their ventures, and started to consult and coach others on the startup path. More importantly, I’ve prioritized genuine connection with other founders, coaches, and mentors. This support structure is why I’m in the healthiest spot I’ve ever been.
My journey is the reason why coaching and consulting isn’t just a paycheck. Entrepreneurship isn’t just a career path for those gifted enough, rebellious enough, or stupid enough. It's an opportunity to make an impact on your community, your people, or literally the world. To have life on your terms. To live a life that most only dream of. To change your family legacy.
The drive I see in my fellow entrepreneurs lights a fire in me like nothing else does. Working alongside entrepreneurs and helping them identify and break through their own barriers speaks to my very soul. Because of that, I wouldn’t trade my brutal journey for anything in the world. Since then, I’ve coached and consulted with literally hundreds of entrepreneurs, helping them turn trials into triumphs.
Listen. If you don’t have a coach, I want to make a direct ask of you. Connect with me or a qualified coach. The journey is too arduous to do alone, and you get no bonus points for doing it the hardest way (trust me). Take the initiative and risk to reach out to someone who’s walked that path you want to walk. Tell them you admire their journey and ask them to mentor you. I can attest to the night & day experience of having a sherpa guide you on the path.
So here’s the deal. If you’re in a venture that has stalled, you’re uncertain where to go from here, or you have limited runway to make/break your idea, product, or service, reach out to me. I commit to giving you an immediately constructive consultation where we identify challenges and start workshopping solutions on the very first call. Try me.
Thanks for reading and I genuinely hope to talk to you soon.
-Alex
