The path of the entrepreneur is beset on all sides by the inequities of the selfish and the tyranny of evil men. Blessed is he who, in the name of profit, shepherds the user through the funnel, for he is truly his user’s keeper. And I will strike down upon thee with great vengeance and furious anger those who attempt to poison and destroy my brand. And you will know I am going to IPO when I lay my financials upon you.” — Startup L. Jackson, Aug 12, 2011

For nearly four years, the pseudonymous Twitter account @StartupLJackson has wisecracked its way to Internet stardom. Since being founded, the account has gone from pure parody to a voice of advice and reason within the tech ecosystem.

Over the years, people have tossed around a number of theories about SLJ’s identity, including such big names in the industry as Ben Horowitz, Dave McClure, Hunter Walk and Dustin Curtis.

But the man behind StartupLJackson was never a person with a visible, public profile, at least not at first. Part of the reason a semantic analysis of his tweets fails to identify him is because his personal Twitter account is decidedly unremarkable — to the point where after five years on the service he hasn’t even bothered to upload an avatar.

The truth is, few people would have cared who StartupLJackson was when he first started out. But over the years, just as his Twitter persona has grown to represent a trusted and respected figure in the startup ecosystem, his alter ego — the man behind the cartoonish avatar — has gone on to build one of the fastest-growing startups in recent memory.

This is the story of how one down-on-his-luck entrepreneur reinvented himself, first on Twitter and later in real life, and emerged as one of the most visible CEOs in the tech world.

“Turn On, Tune In, Drop Out, Start Up”

For the first year of StartupLJackson’s existence, his tweets were little more than a self-parody of startup life. His stream was filled with platitudes: “Never ascribe to wisdom that which can be adequately be explained by luck” and “Blessed is he who, in the name of profit, shepherds the user through the funnel, for he is truly his user’s keeper.”

But it also included tweets showing overall frustration with tech work.

Behind the sometimes bombastic nature of the account was an entrepreneur brooding. Earlier in 2011, the man behind StartupLJackson had been demoted from co-CEO of the company he had helped found years prior, as it pivoted and reincorporated with cash from his co-founder’s friends and family.

But as StartupLJackson wrote in February 2012, “Friends don’t let friends invest in their startups.”

That was prescient advice, as just a few months later, he found himself out of a job.

“Keep Calm And Startup On”

Just as he reinvented himself on Twitter, in the second half of 2012 StartupLJackson began the process of building something new. Taking a meager amount of savings, he started working on what would be the next pivot in his life and career.

He had an idea — to build the kind of platform for managing HR and benefits accounts that he wished he had during his previous two startups. While not a particularly adept coder, he had a nuanced understanding of the problem he wanted to solve. And that was enough to get started.

Years later, StartupLJackson would write:

The simple fact is that the majority of great software startups today (slightly dated) required no technical insight to start, and you can always hire experts to help you scale. The driver of these innovations is an uncommon understanding of what the customer (aka humans) wants or how to deliver an understood solution it in a better way.

That said, he knew he was at a disadvantage as a non-technical founder. Though he taught himself to code a bit, he would need some technical help, so he recruited one of his former engineers as co-founder and set about creating the first version of his product.

Team building, like sausage making, was “about manufacturing a perfect whole from imperfect parts,” he wrote at the time.

Hey, you’re not vested, and my funding’s sketchy. But I need a CTO, so call me maybe? — Startup L. Jackson

Around the same time, while StartupLJackson was apparently looking for some initial seed funding, he dropped 99 Startups, a riff on Jay-Z’s “99 Problems.”

With the opening verse “If you’re having funding problems I feel bad for you son / I got 99 problems but my pitch ain’t one,” the spoof lampooned the fundraising process.

The founders were accepted to Y Combinator as part of the Winter 2013 class, and early that year they launched the first version of their product, initially focusing on companies in California — and, more importantly, signing up some young tech companies to help them scale their human resources operations.

In those days, you can read some of StartupLJackson’s tweets as a personal affirmation of his choice to go back into the startup game. They’re almost likeStuart Smalley’s insistence that he’s good enough, smart enough, and doggoneit, people like him. Like that, but with a little more profanity.

But it wasn’t until after Demo Day, and after launching on stage as part of the TechCrunch Disrupt Startup Battlefield, that they realized just how in demand they were.

“Live Every Day Like It’s Demo Day”

In the run-up to Y Combinator Demo Day earlier this year, StartupLJackson had some advice for founders who would go through the feeding frenzy that occurs after presenting in front of a roomful of press and investors. He was able to do that in part because he had went through that process himself.

Following his own Demo Day two years earlier, the fledgling company fielded offers from a number of investors. The fundraising process was not without its hiccups, which StartupLJackson highlighted in a series of tweets over the next several months.

Despite only serving companies based in California and New York, his company racked up more than 100 clients by July, and ended up raising a modest $2.1 million in funding from a wide range of investors.

The team grew from a modest 12 to more than 20 by October. More importantly, the product was ready for mass-market adoption and the company expanded to serve all 50 states that month. With product-market fit and national expansion underway, it was time to go back out and raise more money.

“Lies, Damned Lies, And Business Plans”

The company was growing fast, with its customer base expanding from 100 companies using its platform to more than 500 in a period of months. But the road to raising its Series A may not have been as easy as you would expect. A couple of tweets from that time period highlight the process that was underway.

One referenced what StartupLJackson called the “Series Sprout,” or the “formal name for that awkward round between your seed and A that sounds less like you fucked up than calling it a bridge.” Another, riffing on a classic Beastie Boys sample, reads “Shit, if it’s gonna be that kind of party round, I’m gonna stick my term sheet in the mashed potatoes.”

A few months after national launch, however, his company raised $15 million from Andreessen Horowitz. On the day the funding was announced, StartupLJackson tweeted, “Fundraising is an exercise in restraint. You must not get high on your own supply, while selling *great* shit to unsuspecting white people.”

(Previously, StartupLJackson tweeted that Marc Andreessen “answers all cold emails.”)

Now well-funded and looking at a huge market opportunity ahead of it, StartupLJackson’s company was poised to go through a period of hypergrowth rarely seen among startups just a year old.

“Execution Is The Only Moat”

From a business standpoint, 2014 went by in a bit of a blur. The company grew from a couple dozen to more than 500 employees over the course of the year. It raised another round of funding — this time a $66.5 million round from Andreessen Horowitz and Institutional Venture Partners. And it hired a big-time COO with multiple exits under his belt.

At the same time, it faced some serious strategic decisions. StartupLJackson hinted that the company had been approached with at least one acquisition offer but had declined it in the early part of the year.

“First they ignore you, then they ridicule you, then they try to make you illegal, then they try to buy you, then you IPO” reads one tweet, while another states, “You either sell a hero or you stay independent long enough to see yourself become the company doing layoffs.”

The future is already here — it’s just not legal everywhere yet. — Startup L. Jackson

Like many other fast-growing startups, the company faced regulatory challenges for the first time. The Utah Insurance Department threatened to shut down its service in the state for its practice of giving away its HR management tools while collecting commissions on insurance customers booked through its platform.

That came in direct opposition to its entire business model, which StartupLJackson more or less described in this tweet: “The most formidable new entrants figure out how to give away whatever that incumbents are selling, and then sell something incumbents can’t.”

Regulation, he argued, “attempts to prevent bad things that happened from happening again,” but wasn’t “optimized to make good things happen in the future.”

“Extra Clips For Extra Shit”

As StartupLJackson’s company matured, so did his tweets. While running a company focused on HR tools for SMBs, through his Twitter account he commented on a wide variety of topics.

StartupLJackson had an opinion on everything from Bitcoin — which led more than a few people to believe he was Chris Dixon or another cryptocurrency enthusiast — to social apps to marketplace startups to the tension between founders and the investors who fund them.

Worried about somebody stealing your amazing idea? Get traction. That shit can’t be stolen. — Startup L. Jackson

On that front, he continued to gain invaluable experience as he sought a new round of funding that would be in the hundreds of millions and value his company in the billions of dollars.

In late January, StartupLJackson alluded to an exchange with a VC who wanted in early just to get ahead of others seeing the deal. In February, he referred to the “obligatory five year revenue forecast slide” as “uniporn.”

While behind the scenes he was in the process of locking down what Biggie would call “extra clips for extra shit,” in an extended Tweetstorm, he appeared wary of the cultural impact such news would have for employees at the company:

One of the biggest cultural mistakes companies make is treating fundraising like success. It’s easy to do after 2–3 years of ramen & sweat. That $20M check comes in and employees think “we’ve made it.” Founders feel validated. Mom is finally proud. The party to celebrate the round is the thing that really kills you though. It tells the company fundraising is a KPI. Celebrate 1M users, $10M in revenue, whatever your KPIs are. Discussing fundraising is only useful for press/recruiting, a necessary evil. Remember, any idiot can cash a check and many have big check books. Keeping a team focused & executing, that’s fucking hard.

That wouldn’t stop his company from closing a $500 million round of financing valuing it at $4.5 billion. On May 1 he celebrated by saying “every team should have a song for when the round closes and the money hits the bank” and suggested that song should be Bone Thugs-N-Harmony’s “First Of The Month.”

Quoting Seinfeld two days after the round was announced, StartupLJackson explained, “People don’t turn down money, it’s what separates us from the animals.”

“Forgiveness > Permission”

When I first heard that StartupLJackson was Zenefits CEO Parker Conrad, I was a bit taken aback. “You mean the guy on Twitter who is still an egg?” I thought.

Then I went back and looked through StartupLJackson’s tweets and saw just how closely so many of them tied back to significant moments in Conrad’s entrepreneurial journey and the growth of Zenefits as a company.

It was like a Keyser Soze moment — the clues were there in front of us all along, and the guy behind StartupLJackson was just hiding in plain sight.

The fascinating thing for me is not that we now know who StartupLJackson is — I’m not doxing him for the sake of doxing him. What’s interesting is how closely StartupLJackson’s rise as a public figure mirrors Conrad’s own rise to startup superstardom.

If the true identity of StartupLJackson had been revealed two years ago, most people in the tech community would have shrugged their shoulders and asked, “Who?”

Even a year ago, unveiling Conrad as the voice behind Twitter’s most badass of parody accounts would be interesting, but not world-changing.

But now?

StartupLJackson is no longer just some random Twitter user who happens to work in tech. He’s the founder of one of the fastest-growing SaaS businesses ever, whose company is now worth $4.5 billion.

All the while, he was able to tell us what he really thinks, in part because he was speaking through the voice of a cartoon avatar.

I’m not sure what will happen to StartupLJackson now, whether he will continue to maintain the account or not. Even if he disappears, it’s been fascinating to see how he was able to re-invent himself, first on Twitter and later as one of the more successful new founders out there.