“Sally’s. Easiest question you’ll ask me all day.” Like most other natives of southern Connecticut, Jay Acunzo had very serious opinions on the only acceptable pizzeria to frequent, as evidenced by his instantaneous response.

He also wasn’t impressed by my own favorite West Haven haunt, Zuppardi’s. “We’re comparing platinum to gold here. It’s all good pizza, but if you have a choice, you might as well go platinum.”


If you happen to have been living under a marketing rock for the past few years, Jay is an award-winning podcaster, keynote speaker, and a veteran content marketer and creator.

However, a debate on the merits of different New Haven style pies was not exactly what I had prepared for while on the Amtrak to New York that morning, on my way to interview the creator and host of the podcast Unthinkable and the founder of podcast incubator Unthinkable Media.

What I HAD done in preparation was listen to some of my favorite Unthinkable episodes from Jay to find out what it was about his work that keeps me and countless others coming back for more. Top picks like “Dumb Ways to Die” – a look at how a public safety campaign became a viral phenomenon – and “The Man Bun” – which kicks off with a blacksmithing demo – smacked nothing of a so-called “marketing podcast.”


Investigating this question brought me back to pizza. People adore New Haven pizza, and aren’t afraid to tell you everything about it – why the style of pizza is allegedly superior to all others, which pizza purveyor should be your choice when visiting Connecticut, what topping combinations are best, and so on.

Jay’s statement on pizza was bold, full of passion, and inspired an immediate emotional response from me. Which is what plays out episode after episode on Unthinkable and other podcasts he creates – telling stories you get invested in, make you care, and are actually worth listening to.

What Jay’s doing in his podcast and in his broader work is both different and authentically him – magnetic, real, and just a little bit quirky. He seems to be one of those lucky few who have found a way to create a career that sparks excitement and passion in him every day.

It’s because of both my enjoyment of his podcast, as well as my personal quest to find more meaning in my own work, I felt compelled to hop on a train and talk to Jay face to face to find out how he got to where he is today.

The humble podcaster

“Is this what you expected?” he asks, motioning to the cramped barely-a-second-bedroom home office inside his New York City Apartment. I answer before I have a chance to really think it through.

“No… I mean, I’m not sure what I expected, but I guess I did expect something a bit more substantial.”

He grinned. It was clear that this was an obvious point of pride for Jay. Turns out you don’t really need much to launch a podcast empire. His home office was classic New York City – a tiny room with one window letting in some light. A small desk supported just two screens and a modest microphone setup – that was about it.

Anyone could put this set up together, it seemed. And that’s really Jay’s point. He explained, “You don’t need a lot of flashiness or a professional studio to have a podcast people want to listen to.”


Jay launched Unthinkable in 2016 as a standalone podcast. What started as a side project while he worked at NextView Ventures has turned into a full-time job and spawned a standalone company that is a self-described podcast incubation and education organization. Today, his original podcast has received hundreds of thousands of downloads and his company has six shows it’s working with (and growing).


“Do you think you’re lucky?”

Jay pauses, collecting his thoughts. He is very thoughtful about the words he chooses. “Luck is how far open the door already is for you. Hard work is how you shoulder the rest of the way through the door.” Jay is also great at coming up with colorful turns of phrase.

“Of course, I am incredibly lucky. There was a .001% chance of being born when I was born, as a white male in America, with supportive parents that are still together. That is the state of my life. I know it’s not a level playing field. My job is to make sure that I cash in on my good fortune, and let other people know that this is a path they can explore too.”

Before he was Jay, he was Jason, growing up in an Italian family “with lots of noise and food.” Jay describes himself as the family comedian, the one who always wanted to be in front of the camera. “Looks like I found a way to make a living off of that!”

His childhood dream was to be an “animal seller.” Turns out he really meant a pet store owner, evidencing his still extant love for animals. “I grew up with a cat a dog, lizards, tree frogs, newts… loved animals.”

As if on cue, Nocci, his beloved three-year-old beagle, starts howling at the door of the home office, seeking attention. Jay did warn me that his pup would likely try to make this interview all about him. Good news – I love dogs.


Over time, Jay realized he was interested in the more creative side of things, and it wasn’t until high school that he decided what he wanted to pursue – sports journalism.

When doing everything “right” isn’t enough

Jay studied English in college, was the newspaper’s sports editor and even scored an internship at ESPN, where he was offered a full-time PR and communications gig. “It’s the mothership of sports.” And it seemed to be everything he’d been working towards.

Then 2008 happened, and suddenly, he was told the job no longer existed.

“I did all the right things. I got the A+. I was president of the clubs. I was THAT student. And I graduated and suddenly had nothing lined up. My mind was not prepared for that scenario.”

A story familiar to many fellow millennials, Jay moved home to figure out what to do with his life. He started looking around for all kinds of jobs, applying for roles in PR, marketing, and journalism.

In a twist of fate that Jay still is confused about, he found his way into Google, totally by chance. “I got a job at Google by filling out an online form. Which flew in the face of everything I thought I knew about the tech industry and networking. I don’t know how the heck it happened.”

Google was seeking out what they called “mental athletes” at the time – people who pursued their passions. “They were changing all the time, building the future, so it was less about specific skills and more about people with passion.” Jay’s standing hypothesis was that his college sports pedigree and the ESPN brand name were dead giveaways that he was someone pursuing a hard-fought path.

“In every room, there was like a former Olympic kayaker, a sous chef from a Michelin star restaurant… everyone was deep into seemingly non-applicable things. They just wanted people that pursue a passion, come hell or high water, not necessarily fitting into a specific mold.”

Giving up someone else’s dream job, and stumbling onto a path

“Google was where I had the worst job in my career.” As he describes it the job itself – a digital media strategist consulting with brands on search, display, YouTube, and mobile campaigns

– was awful, but the wrapper was great. “Soul-crushingly boring, no creative work at all… but access to some of the smartest people in tech, a generally great company for employees. I even met my wife there on my first day.”

Jay was very clear that Google was not some awful terrible place — it just didn’t work for him. And it caused a bit of a career crisis for him.

“This was the best company to work for on the planet, and I didn’t want to work there. I wondered, what’s wrong with me? We’re trained to find the right answer, the right best practice. But turns out what matters isn’t doing what’s supposed to be done, but doing what’s right for you.”

This idea lit me up, as someone with my own nontraditional career path. I noted the previous expectation of your career humming along to the tune of work, work, work, gold watch, die.

“I love that.” Jay said enthusiastically. “Now you’ve got me on my soapbox! You get one life, you might as well use it as best you can. Find a way to like what you’re doing now, not later.”

The tipping point at Google happened for Jay when he was showing his roommates a funny YouTube video.

“I was like ‘Guys, you have to check out this video!’ And I hyped it. And we were around the kitchen table around a laptop, leaning in with anticipation. I went to the link and hit play… and a pre-roll ad popped up!

“I was so pissed. This was before the skip button, and it was like air had been let out of the room.

“And I had this thought in my mind which was, ‘Damn it Eric!’ – Eric being my colleague at Google who had convinced this advertiser to start a YouTube campaign. And I realized, I have the same job at Google as Eric. That means that thousands or even millions of people are out there right now, cursing the person responsible for a terrible experience in their day. And they didn’t know it, but that person is me.”

“That’s when I made the decision that it wasn’t what I wanted to do.”

Leaning into the creator role.

Jay took full advantage of the networking opportunities provided through Google. “I realized I didn’t know a single human being in the business world outside of the company. So I started going to events and meeting people.”

Slowly, he expanded his network until he found an opportunity at CampusLive, which later became Dailybreak where he worked as an account executive selling to build brands. “I also had the opportunity to help create content for clients.”

Jay never really was a writer at Google, but his side projects (allstarblog.com and crankyyankeefan.com, still up if you want to check them out) gave him the experience needed. “Side projects are the story of my career,” he said.

It turned out to be a smart move, as when layoffs hit the sales team, Jay was asked to step up as a full-time content creator. That was a pivotal moment for Jay. “It’s when I went from no potential path to this general idea of creating content.”

“I felt like I had been running underwater and someone had drained the pool. I felt like I could finally sprint in my career.”

Content as a career path wasn’t as common at the time, but when he did find others in the same world, he wanted to create a network of creators. The result was his co-founding the organization Boston Content, which he ran for four years, now 2,000+ members strong.

“Creators used to be this sidecar in marketing… and now they ARE marketing.”

Getting beyond best practice and to true storytelling

Jay moved into a role leading the content team at Hubspot, but he struggled with the intense focus on lead generation. “It was all about more and more names in the database, not necessarily the RIGHT names. Every month was a grind.”

“As marketers, we’re too fixated on what works in general – that’s what best practices are – instead of what works for an individual or team. So it becomes commodity work.”

It was his next opportunity at NextView Ventures, where he was vice president of content and community, that he credits as the next real pivot. There, he had the chance to experiment and ultimately fell in love with podcasting as a storytelling medium with the launch of their show, Traction.

“Being able to tell emotional, fun, interesting stories really breathed new life into B2B content. Turns out, if you ultimately want a lot of customers, you need leads, you need subscribers, AND you need loyal readers or listeners. But that all starts with creating something worth listening to or consuming in some way, growing an audience versus just immediately delivering a result.”

Unlocking the side hustle

“What do you love about podcasting?” I asked him.

Jay paused – he’s clearly thought about this before. “It’s intimacy that scales. I love making other people feel something, real emotion, and see that come back to me.”

“It’s like when you ask, what makes Nonnie’s cooking so good? It’s made with love. It’s cheesy, but true. Content to me is the same – it isn’t this hollow container, it’s what’s inside the container.”

While working full-time at NextView, Jay toyed with his next side project – a personal podcast. For three months, Bourboun in Porter Square, in Cambridge, Massachusetts. He sat in the same seat every morning, ordered the same drink (iced latte with skim, if you’re curious) and created a show.

“It never felt like a grind because I was so excited.” It was what he called the theme of his career: a nose for excitement.


As if on cue, Nocci nuzzles me. The idea of working from home, on a passion project, cuddling a dog… it seemed like an incredible dream that was at the same time terrifying.

“It’s all about taking the next step, not some giant leap. I mitigated the risk, going from full time to part time at NextView, and I found other ways to get revenue in the door [through speaking engagements] before I actually made the leap to full-time podcaster and speaker.”

The planner in me was relieved to hear that he didn’t immediately dive headfirst into his side project as a full-time gig.

“Turns out you just physically can’t go from zero to 60. You have to hit every single number along the way, and that’s the part no one talks about. The middle is boring and messy to talk about, but it’s where careers are made.”

Doing what comes naturally

A popular podcast, a business that’s growing, and even a book project in the works (more on that in a moment…) – it made me wonder what made Jay so successful.

“Exceptional work happens when you find and follow what makes you an exception. We’re taught to mimic success, but you need to be willing to do something different in your work. For me, I think it’s my willingness to get incredibly emotional in the stories I tell about business. And it seems to be resonating.”

Which brings me to his latest side project: writing a book (Break the Wheel: Stories & Ideas for Being Better Than Best Practices is expected to be out in the fall of 2018). I asked Jay to talk about that experience so far.

“While writing a book is a lot like writing everything else, all those crises you experience as a writer definitely get worse, so I’m certainly working new out some new creative muscles.”

Jay seems to be staying true to his notion of doing what comes easily and naturally, while also constantly building towards more. Going from account manager to content creator to podcaster and public speaker wasn’t necessarily a plan, but every step was built on the one before it.

“You have to just make stuff and see what happens, and not rely on best practices or expectations.”

Perhaps that’s really all it comes down to — fearlessly creating, both in marketing and in your career, in a way that is authentic to you, not beholden to any expectations, and certainly not to any best practices.

Jay does what comes naturally to him – telling emotional stories about real people, real work lives – and it’s working. Shouldn’t we all be able to do a bit of the same?