He Got Laid Off at 9am on a Monday - With a Baby on the Way. Then Became One of the World's Best Content Marketers
If you’re nervous about your job right now, maybe even holding your breath every time you see a surprise calendar invite… you'll love this story
Hey 👋 I’m Andrew. Welcome to Delivering Value - the newsletter and podcast where I share stories from SaaS leaders about the toughest moments of their careers, and explore how they turned them into success stories. You get the lessons - without the scars.
Three weeks after his honeymoon, John Bonini opened a calendar invite.
A Monday morning “Catch-up,” at 9:00 am from his new boss. It was scheduled late on Friday afternoon, and he’d spent most of the weekend thinking about it. He clicked the Zoom link and was greeted not by one smiling face, but three: his boss, the head of marketing, and the head of HR.
He knew exactly what it was.
“I’ve heard people call it a firing squad,” he told me. “That’s what it felt like.”
He didn’t say much in the meeting. But inside, he was seething. His wife was pregnant. He’d just bought a new car. They had one child already at home, with another on the way. And the timing of it all (first of the month, before the next pay period) sent a message loud and clear.
This was business.
But what John did next is the part I can’t stop thinking about.
Because I know a lot of people who would’ve spent the next month licking their wounds. John got up the very next day and started booking calls. Because that moment, as painful as it was, didn’t break him.
It lit a fire.
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John grew up with two obsessions: hoops and writing.
He can still hit 90% of his free throws (there’s a video below for proof).
But it was the other passion, writing, that ended up shaping his career.
In middle school, he won the superlative “Most Likely to Become a Published Author.” At the time, he hated it. “You want to win funniest or best-looking, not that,” he laughed.
But writing was the thread he kept following.
Through journalism school. Into a content role at a HubSpot partner agency. His very first blog post got picked up by HubSpot and blew up. Pamela Vaughan emailed him. Dan Tyre DMed him. People at HubSpot were saying: this is good. You should keep going. Way before he was leading growth at Litmus or marketing at Databox, John’s writing was already turning heads.
One post, on the value of social media got syndicated by the Wall Street Journal.
A throwaway line about monetizing Lady Gaga’s Twitter following made it to Rolling Stone, CBS, even local morning radio. “I was afraid Gaga was going to sue me,” he laughed.
But the real inflection point didn’t come from viral success.
It came on a Monday morning, when everything changed.
This is where it ends? After everything?”
The layoff came at Litmus, a company that helps marketers test and send better emails.
They’d bootstrapped to $15M ARR before taking on $49M in private equity. John joined as Head of Growth. No one mentioned the pending fundraise during the hiring process. But once the deal closed, the culture shifted almost immediately.
A new CEO.
New VP of marketing.
New bosses (who were ghosting meetings).
Startup energy, replaced by corporate playbooks and politics.
Slowly, John saw the writing on the wall.
He told his wife something felt off. Talked it through with his mother-in-law, too.
“They were both kind of like, ‘Yeah, I see what you're saying, but I think you're just being paranoid.’”
Still, he couldn’t shake the feeling.
Then one Friday, at 5:30pm, a surprise invite popped-up on his calendar:
“Catch-up”
It was scheduled for the following Monday at 9am with his boss. He knew what that meant. And when he opened the Zoom and saw three faces, not one, it was confirmed. Three weeks after his honeymoon, with a baby on the way, a brand-new car payment, and zero warning.
He stared into the screen, stunned.
“You give everything to a company, and this is how they treat you,” he said. “And for the record, they were great about it. They said all the right things and treated me with respect on the way out. But that didn’t make it easier. I was angry”.
But John didn’t wallow. He got to work.
Tuesday morning, he was already back in motion.
“Monday, I needed some time to blow off steam. But Tuesday morning I was reaching out to my network,” he shared.
“Part of it was a middle finger, I was like, no. I’m not gonna sit here and mope. I’m gonna get hired before my first severance check even hits.”
That mindset shaped his next move.
Three opportunities emerged after Litmus: a hot company with $150M in funding, another buzzy startup, and Databox - a tiny analytics platform doing just $30K MRR at the time. John chose Databox.
Why? Because Pete Caputa was their CEO.
The same Pete who built HubSpot’s partner program from zero to $100M+. “If I’m going to follow anyone into something that early,” John said, “I trusted Pete.”
(Reader side note: I worked on the first version of that partner program at HubSpot in 2012. Pete won the Founders Award that year, which is essentially employee of the year. So I understood.)
The risk paid off and over the next six years, John built the content and growth functions from the ground up, scaling the company from 30k MRR to millions in ARR. In the process, he got the experience he wanted: hiring teams, navigating messy growth stages, and learning the zero-to-one phase most marketers never see up close.
But in the background, something else was quietly taking off.
His side hustle was starting to look like something more.
In 2020, John launched a Patreon called Some Good Content.
He broke down how to write, package, and promote content that actually stood out. He figured a few dozen people might join. Hundreds did. Sponsorships followed. Then coaching. Then consulting.
His content wasn’t just resonating as a writer. It was working because he was a great teacher.
Pete saw it too.
One day he asked, “Have you thought about going full-time as a solopreneur?” This wasn’t like last time. This wasn’t a layoff. It was a choice. And that made it scarier. Because once again, John’s wife was pregnant. And once again, everything felt on the line.
“I’m not super risk-tolerant,” John admitted.
“We’ve got five kids on one income. My wife stays home. So if this doesn’t work, there’s no parachute.” But this time, he wasn’t starting from scratch. He’d been building in public for years. His newsletter had sponsors. His writing had a following. Clients were already knocking, he just wasn’t ready to say yes to them.
So he simplified the decision.
Give it a few months. Try to match his old salary. Then see what happens. He said yes to Pete, and Databox became his first consulting client.
Within a week, new ones followed.
The details were different, but the feeling was familiar.
Years earlier, John woke-up to a layoff.
Suddenly, he had no boss. No meetings. Just a pregnant wife, a new car payment, and a pit in his stomach.
Now, waking up after leaving Databox, the circumstances had changed - but the details were strangely similar. No formalized agenda. No one telling him what to do. But a quiet pressure to make it work.
“I got my first client that first week,” he said. “And suddenly I was like - oh. Maybe I can do this.”
What followed was the solopreneur glow-up.
He started saying yes to projects that lit him up. Helping brands develop content IP that actually stood out. He turned the playbooks he used at Databox into a service companies wanted to buy.
His consultancy is appropriately called, Content Brands.
When I asked him what he’s proudest of, it wasn’t the revenue or the logos. It was what his kids are learning by watching him.
“My dad ran a business for 40 years,” he said. “People would call him for anything - how to fix a tire, how to set up a retirement account. He just knew stuff.”
“I want to be that for my kids too.”
“I want them to know: Dad does hard things. We can too.”
So if you’re nervous about your job right now - maybe even holding your breath every time a calendar invite lands in your inbox...
Remember John.
He got fired on a Monday, at 9 am, with a baby on the way. Now he coaches the world’s best content teams.
Not because he never fell. But because he got up the next day and said:
Let’s go.
Catch John’s entire story on YouTube
Listen on Spotify
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