Trent Lapinski


Confessions of a San Francisco Millennial Startup CEO

Trigger warning: This editorial expresses opinions, and emotions. It is a counter perspective to all the fluff pieces you commonly read on startup tech culture, and tells the story of an entrepreneur who believes in creating a better future for everyone, and not just the wealthy elite. If some people read this and come away thinking I am just some privileged Millennial whining about how no one invested in my startup, those people are missing the point entirely.

When I first wrote this a year ago, I couldn’t bring myself to hit publish. At the time I originally wrote this I had just watched the lost Steve Jobs interview, and Jobs told this story about how when he was 12 he looked up the CEO of HP in the phonebook, called him, and asked for spare parts. The CEO of HP spoke with him for about 20-minutes, and gave Jobs a summer job at HP.

When I hear of stories like this I sometimes think I’m living in the wrong era. I imagine if I tried to cold call the CEO of a major corporation in the US today it would likely result in the FBI showing up at my door asking me how I got their number, and accusations of being a hacker. There would be no 20-minute conversation, no job offer. I would likely be treated with suspicion, or worse. The fact that Jobs could call up whoever he wanted and actually speak to them as a human being and ask for help is a luxury I have not experienced as a Millennial.

Selling my startup felt like waking up from a coma.

When you’re working 16-hour days it is hard to pay attention to wealth inequality, politics, and what is happening in the world. Hell, I wasn’t even paying attention to my own health when I was running my startup, which is still around 50% of what it was when I first started my company in 2011. Apparently, all those antibiotics and antidepressants I took to keep me going wiped out my gut flora, messed up my brain chemistry, and lead to systemic infections that have seriously compromised my health. Factor in my TMJ headaches from clenching my jaw in my sleep, kidney stones, chronic neck pain from a car accident and looking at a computer all day, and my clearly burnt out immune system it is a testament to human will that I’m even still alive.

Unlike other San Francisco startup CEOs today, I was actually born in San Francisco a mere 10-minute walk from where I live now. I grew up in the North Bay, and this is my actual home. I am not some transplant who recently became a Giants fan because it was trendy, and who goes home to wherever they came from for Thanksgiving and Christmas. I spend the holidays here, with my family. Meanwhile, I’ve probably watched every 49ers game for the past 20-years, even during the dark years. Hell, I actually remember when the Giants and 49ers shared the same stadium when it was actually in San Francisco. I was also here for all the joy and sorrow that was the dot com bubble.

My Dad is a Baby Boomer hippy from Brooklyn who resettled in the Bay Area after driving his Volkswagen van across the country looking for the perfect place to live. After settling in Marin County, he eventually became a producer and director in the music industry. I grew up backstage running around the Bill Graham Civic Center with bands like Green Day and Metallica, as well as the Paul Masson Mountain Winery with the likes of Ray Charles, Bonnie Raitt, Carlos Santana, and B.B. King. Despite being brought up around some of the most brilliant musicians in the world, my personal story started with a different set of circumstances.

Back in the 80’s a company known as Apple Computers, use to sponsor some of my Dad’s shows. They even donated a brand new Macintosh SE that my Dad decided to put in his home office. After first using a Macintosh SE I became enamored with technology. I learned to read and write from Reader Rabbit, and created pixel art in Kid Pix while other kids were busy using crayons I explored the Oregon Trial, and did my best to find Carmen San Diego.

My Mac taught me that the world is palpable, and that everything in this world was created by someone else. We literally live in a universe where anyone can manifest their thoughts, ideas, and desires into reality. Much like my heroes, I grew up to be an entrepreneur, started my own startup, and bootstrapped it to over $1 million dollars in revenue, then sold it for a “successful” exit.

After selling my company, I finally started reading the news and books again, writing, and studying all the things I missed out on when I was working 60–80 hours a week. I also reconnected with old friends, some of which were born here as well, only to find out many of them are now slaves to the companies I grew up admiring, under paid, in debt, broke, sick, or going homeless. In a weird way, every friend I reconnected with felt like a punch to the gut. While I was happy to reconnect, it was alarming to face the reality of what my generation is going through.

All the empty promises for a bright future for my generation have gone unanswered, and I feel like I’ve just awoken into a Neal Stephenson science fiction novel of reality where I pay $3,708.82 a month for rent for a 1-bedroom apartment so my girlfriend and I can have a dog. We now live in a world where an entire generation of Millennials are forced to spend all of their money on inflated rent, bills, taxes, fees, debt, loans, penalties, and what little money they have left goes into over-priced insufficient health care, poisonous food, contaminated water, and big pharma drugs that are making us all sick, stupid, and fat.

Our country is now a surveillance police state, and our civil liberties have been traded for a false sense of security. Meanwhile, everyone I know and love is a slave to a casino financial system that has robbed my entire generation of our youth, health, ability to own a home, and start families of our own. To make matters worse, everyone is trapped in echo chambers, and divided by the mainstream media and social media due to identity politics because the technology that was supposed to set us free has instead been weaponized against all of us.

I am pretty sure running a startup tried to kill me, and waking up from the comatose reality of my startup broke my heart.

Later in the Steve Jobs interview, Jobs went on about how he had the support of many people throughout the early days of Apple. Despite the fact that Steve Jobs was an emotionally volatile drug-using hippy, he had the support of many people who were older and wiser guiding him for most of his career.

Had the Greatest Generation and Silent Generation never supported Steve Jobs, even from the age of 12, Apple as we know it today wouldn’t exist.

I’m a Millennial poster boy for what success is supposed to look like in Silicon Valley today, and I am here to tell you something is seriously not right. In today’s Silicon Valley, bootstrapping to over $1 million dollars in revenue apparently isn’t good enough.

We weren’t a unicorn, we were an actual business.

I had a small, distributed, and diversified part-time team of up to 18 people from around the world working with me, but it just wasn’t enough. We grew too fast. I did everything in my power working 16-hour days and endless nights, but we just didn’t have the cashflow to hire the team full-time and make the new hires we needed. The overhead just kept increasing as my company grew without the resources the company desperately needed to grow with it. Meanwhile, the very systems and societal structures that were supposed to help us did everything in their power to make sure we did not succeed.

Just 15-years ago, my startup would have been an investor’s wildest dream: a marketable brand, hundreds of thousands of users, tens of thousands of customers, a million unique visitors to our website per year, and a solid team. All an investor would need to do is bring the team on full-time to develop new products, turn the business into a market place, and ramp up marketing to get a return on investment. Everything was in place to do this.

Maybe I was talking to the wrong people? I even publicly announced I was looking for an investor on our company blog, and e-mailed over 100,000 people including dozens of multi-millionaires and Angel investors, and only one offered to help me and I eventually never heard back from them.

I weighed my options, tried to pivot, and failed.

Although I barely survived my “successful” exit, I have no belief I deserved any kind of special treatment. I am simply writing this to express my frustration and to educate future entrepreneurs of my mistakes, and the reality of the systems we live in.

I have sacrificed relationships, severely messed up my health and sanity to run a startup, but it was to no avail.

My intention for writing this editorial is to tell the story every “successful” startup founder wishes they could shout from the top of Mount Tamalpais, but cannot out of fear, or because they signed a non-disclosure agreement preventing them from doing so. I wrote this because I believe we need to create a better system, and a better future for everyone. I am sick of all these digital lines in the sand, and pretending that current startup culture is something to be proud of, because the reality is it is not. The system is rigged just like everything else our parents generation got their hands on.

At 30-years old, I am already exhausted fighting for numbers on a computer screen with no other meaning or value. If it were up to me, I would spend all of my time helping others, and creating real value for actual people. Working like a slave only to spend all your money on rent, taxes, insuficient health care, and fees to be able to live in the city you were born in is bullshit.

I’m upset that my generation has been robbed of the opportunity to create our own destiny, and even the “privileged” can no longer get ahead unless someone wealthy gives them money. That is the reality of America and Silicon Valley today, and it just doesn’t seem very American to me.

A few winners at the Casino is not change, opportunity, equality, or even a sustainable system for the future. Entrepreneurship in America is in serious jeopardy as long as our economy is rigged to benefit a very small minority and punish everyone else. Real, revenue-driven businesses cannot survive in current economic conditions without millions of dollars sitting in the bank. A new generation of American hackers and problem-solvers will never have a chance if wealth inequality and cost-of-living inflation are not addressed now.

Ever since I sold my startup a year ago, people keep congratulating me.

Everyone keeps telling me that I’ve “leveled up” and accomplished something amazing. However, unlike a video game, there was no new car or home to settle down in upon “leveling up.” Hell, I can barely even afford Obama Care (which is half the coverage at nearly double the price of my previous plan), and even with dual income between my girlfriend and I, all of our money goes to inflated rent and organic food that doesn’t make us sick.

Between my companies revenue and my exit, I’ve managed well over $1.6 million dollars in the past 7-years. Unfortunately, none of it was ever really “mine.” Not because I squandered it, or because I was irresponsible, but because I played by the rules, created jobs, and did the right thing. I paid my team as close to a living wage as possible, paid myself very little, paid a ton of money in taxes, loans, credit cards, lawyers, accountants, insurance, and invested whatever was left over in new products and services to grow the company. If I went back in time and could do it all over again, of course I would do things differently knowing what I know now but I cannot so all I can do now is focus on the future, and learn from my mistakes.

The fact of the matter is running a business today requires an unreasonable amount of cash flow to cover fees, taxes, and regulatory bullshit that prevents most people from owning or running their own business. The laws are so convoluted that I’ve literally had liens taken out against my company randomly by both the states of California and Washington (which I didn’t even do business in), for benefit payments based on estimates these states literally just made up.

When you don’t pay these made up estimates they just steal the money straight from your business checking account, and there is nothing you can do about it. The system is completely rigged to prevent anyone from being able to successfully run a startup or small business. Even if you can afford lawyers and accountants, the IRS and state tax boards are so antiquated they are impossible to deal with and still rely on fax machines.

To make matters worse, there is no way to market a business online anymore without a significant advertising budget. In the early days of the Internet, if you provided value to anyone searching for something relative, people would just organically show up and you could generate free traffic from links, blogs, and social media.

However, in the past several years, every major search engine and social media site has pulled the plug and now forces you to pay to even reach your own network, let alone new customers or fans. Many people are even shadow banned (unable to reach their audience) once they become too popular. The Internet is now mostly a walled pay-to-play garden, and it is nearly impossible for startups to generate business without tens of thousands of dollars to spend on advertising and marketing automation for traffic that use to be free.

The technology that promised to connect us all has actually driven us all apart.

Although Steve Jobs had his own fair share of trouble, especially in his late 20’s when he left Apple, he still had the support of Ross Perot to the tune of $20 million dollars to start NeXT. Years later when NeXT was acquired by Apple, the technology they developed became the foundation for Mac OS X. Once again, the older generation came to his rescue and supported Steve Jobs, and the world benefited.

Now don’t get me wrong here, I’m not comparing myself to Steve Jobs accomplishments, it is not even close. I’m merely using Jobs story to make a point, and keep your attention. I am also comparing the entrepreneurial situations we’ve both faced at similar times in our lives, as well as the circumstances from the past compared to the present. Every time Steve Jobs needed help, someone older and wiser stepped in to help him.

This used to be the way of the world. However, my experience was not so kind. My parents tried their best to help me, but neither of them had the resources or the connections I needed to grow my business. Not a single banker, investor, wealthy friend, or potential mentor gave me the time or resources I needed to succeed. I had to do everything myself until it nearly killed me.

I did everything in my power to find anyone to help even just guide me, but no one outside my immediate family and team even really tried. I was denied from every incubator, and dismissed by nearly everyone I approached for help. In the end, I sold my company not necessarily because I wanted to, but because my health wouldn’t let me keep doing what I was doing anymore. An exit was my only escape, not something I’m necessarily proud of. It felt more like giving up more so than a measurement of success.

Please understand, I don’t blame the Baby Boomers or even my wealthy friends for not investing in my company. It is what it is, I’m actually happier not running a company on my own. Had someone actually invested in me back then it probably would have escalated my stress and health problems even further.

Yet here I am back on my laptop hacking away yet again trying to raise money for a secure cloud computing automation startup that has the potential to disrupt the entire open source and enterprise software as a service industry. My intention is to continue to help other startups and enterprise companies automate their software as a service businesses. It’s the only project I could find that aligned with my values, and that has forced me to learn an entirely new and exciting industry.

I don’t quit, I just pivot.

Despite my upbringing, I actually tested out of high school, and eventually dropped out of college because I couldn’t justify going into debt when I was fully capable of teaching myself, and decided to instead learn from experience working with other entrepreneurs. I created my own path in life, and nothing was ever handed to me to start my company. I had to fight for every dollar I’ve ever earned, and everything I accomplished was from behind a computer, meaning few people even knew my identity until much later. So please spare me the political identity bullshit, very few people were even aware of my sex, gender, or skin color. The fact of the matter is I am just a person like any other, and I accomplished something impossible and although society tells me I succeeded it really doesn’t feel like that. I’m back to living pay check to pay check just like everyone else my age because that’s how the system is designed.

Now don’t get me wrong, I had plenty of luxuries and privileges as a result of owning and running my own company. I was able to write off phone bills, Internet, and all kinds of luxuries including the office space in my apartment for 3 years. While I personally pocketed very little, I was incredibly well off given my low salary because I still had access to cash and credit when necessary for unexpected expenses. I also had all of my basic needs met such as health care. The problem is, these things shouldn’t be a luxury. Health care should be a right in this country.

The truth is money didn’t really make me happy when I had it. Sure, it opened doors to a rigged economy that otherwise would have stayed closed, but if anything it made life more stressful and superficial. Now that I don’t have as much money again it is simply delaying me from doing anything important in life like getting married, starting a family, and treating my health issues. In other words, if you’re a Millennial, you either have to work 60–80 hours a week and never get to spend time with the people you care about to be able to afford a family you will not get to see, or be broke and unable to afford a family of your own. I believe we can do better.

What’s even worse, is every dollar my team and I earned made us complicit to a society, rigged economy, and political establishment that ultimately failed my company, our team, my health, and that continues to fail an entire Millennial generation. It will only continue to get worse. If I can make over $1.6 million dollars and still not be able to afford a home, have a voice, and start a family then I am proof that our economy is so rigged, no one in my generation even has a chance to do things honestly. It feels like the only way to get ahead in this country today is to cheat, lie, and steal your way to the top, or sell a product that harms other people or the planet.

Sure I could have screwed over my employees and walked away with most of the money, but that just isn’t the kind of person I am, nor should I be.

Am I really being congratulated for this?

I didn’t level up, I woke up.

Unlike the world Steve Jobs grew up in, no one was there to listen when I called. So the next time someone you know gets acquired, don’t congratulate them, ask them if they’re okay. I sure as hell wasn’t.

No wonder Steve Jobs died of cancer.

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