This is an impromptu monologue from me, Zach Servideo, creator/host of Boston Speaks Up, founder of Value Creation Labs, and managing partner at Unicorn Studios. And here's what I'm riffing about on in this emergency podcast --> “Workplace survival in the 2020s basically means becoming an entrepreneur.” <-- That line has been echoing in my head for years now. Every month, every CoFlo coworking session, every client conversation, it gets louder.

Here's a summary of topics I'm riffing on in this episode:

1. The Portfolio Economy, in Plain English

Economists have a sterile term for what’s happening: the portfolio economy.

I just call it reality.

We are shifting from a world where most people had one job and one employer to a world where people build portfolios of income streams — projects, gigs, advisory roles, side businesses, creative experiments.

If you run the math, independent work has grown at roughly double-digit compound annual rates over the last decade, while traditional W-2 employment has been basically flat by comparison.

We are very quickly heading toward a world where well under half of the workforce is full-time W-2 — and a majority of people have at least one independent income stream.

So if you’re still betting your entire life on one company, one boss, one paycheck…

you’re playing last decade’s game with this decade’s stakes.

2. From “Climb the Ladder” to “Build the Web”

The old script was simple:

Go to school → get a job → climb the ladder at one company.

The new script looks nothing like that.

It’s more like: Build the web.

You start stacking: client projects, short-term contracts, fractional roles, creative experiments, advisory work, side businesses…into a portfolio of income streams that makes you more resilient and more free than any single employer ever could.

This isn’t just a “freelancer thing” anymore. The data shows that a third to nearly half of working adults are already operating this way — whether they use the word “entrepreneur” or not.

3. Where I’m Seeing It Up Close: CoFlo

One place I see this shift most clearly is through CoFlo, the pop-up coworking community we host around New England.

If you’ve never heard me talk about CoFlo before, here’s the quick version:

We host monthly pop-up coworking days — in places like Beverly, Portsmouth, Weymouth.

People roll in with their laptops, their coffee, their chaos.

And something subtle but powerful happens.

Yes, people show up to get work done. But they also show up with ideas.

In one room, you’ll see: remote workers, creatives, founders, people between jobs, people with jobs they clearly don’t want forever.

You can almost watch the old model and the new model collide in real time.

Over time, CoFlo has organically become a kind of low-pressure incubator: a place where people can bring half-baked ideas, get honest feedback, meet collaborators, and feel that little jolt of:

“Oh wait… maybe I actually can build something.”

4. UnicornOS: An Operating System for Humans in This Shift

I’m not saying any of this from an academic distance. I’m in it.

Together with my partners at Unicorn Studios and Value Creation Labs, I’ve been building what we’re calling UnicornOS — an operating system for humans in this new world of work.

CoFlo is one of the ways we’re seeing this in the wild: real humans, real experiments, real proof that people want to build portfolio lives — even if they don’t have the vocabulary for it yet.

5. A Personal Invitation

You can reach me directly at: zach at unicorn dot love

For the third year running, Boston Speaks Up took over the Startup Boston Week stage for a three-hour live podcast marathon.

This year, we dove into three big themes: raising capital the right way, modern venture studio models, and the evolving role of AI in product building.

In our final segment, we closed with a live version of our recurring AI Happy Hour, featuring Justin Bingham, Clay Unicorn and Marc Gigliotti. Beers in hand, we explored the promise and pitfalls of today’s AI tools.

Justin summed up the shift in a single arc:

“Three years ago, no one even knew what you meant by generative AI. Now we’re in full-blown agentic coding, where you can just say ‘I want this’ and something gets created.”

But both he and Clay stressed the limits:

“AI is like a team of brilliant junior developers. They can do incredible things, but you still need senior oversight.”

The group also mused on hackathons, with Justin noting how much more impactful they’ve become:

“The amount you can build in 24-48 hours now is almost hilarious. I’m surprised there isn’t a hackathon every week.”

We ended with a conversation about fundraising in the AI era — where the “napkin sketch” has been replaced by weekend prototypes, radically changing how founders show traction to investors.

For the third year running, Boston Speaks Up took over the Startup Boston Week stage for a three-hour live podcast marathon.

This year, we dove into three big themes: raising capital the right way, modern venture studio models, and the evolving role of AI in product building.

In this segment, I was joined by Clay McIlrath (aka Clay Unicorn), Marc Gigliotti, and Dylan Wilson for a deep dive into venture studios and new models of collaboration.

Clay described the shift from “coin-operated” agencies to a hub-and-spoke product studio model:

“A lot of agencies just fulfill the work. They do a disservice to innovation. We wanted to build something consultative, startup-minded — a true venture studio.”

Marc stressed outcomes over analysis:

“Get to an outcome, get to an experiment, fail fast. If it doesn’t work, figure out why and follow the data.”

And Dylan spoke to the power of design in an AI age:

“AI can generate outputs, but it all starts to look the same. Brand and design are what unlock a founder’s unique point of view.”

The three of them showcased a studio model where senior operators, fractional contributors, and AI-powered workflows accelerate both client work and new venture creation.

For the third year running, Boston Speaks Up took over the Startup Boston Week stage for a three-hour live podcast marathon.

This year, we dove into three big themes: raising capital the right way, modern venture studio models, and the evolving role of AI in product building.

We kicked things off with Steve Walsh (Hands On Angel, Pitch Lift) and Rob Hughes (Koo Capital, HelpBnk, Pitch Lift). Their chemistry was obvious — friends who often collaborate, they riffed on when founders should pursue dilutive (equity) versus non-dilutive (debt) capital.

Steve was blunt about the importance of networks over checks:

“The most valuable thing I will ever bring a startup is my network. The money is the least valuable thing.”

Rob broke down how Koo Capital plays matchmaker between growth-stage companies and private credit funds, often structuring deals from $500K to $600M. His reminder was clear:

“Equity is about opportunity. Debt is about risk. Equity investors ask how much they’ll make; debt providers ask if you can pay it back.”

Together, they painted a picture of complementary capital strategies — and why founders should think beyond the binary of VC or nothing.

Guest Diana DiZoglio has played a pivotal role in public service throughout her career, serving as an advocate, legislator, and now, Auditor of the Commonwealth of Massachusetts. In her role, DiZoglio is committed to increasing transparency and accountability in state government, ensuring that all residents receive equitable treatment, regardless of their background, financial status, or zip code. Her work as Auditor underscores her dedication to fostering a fair and inclusive government for all.

Being born and raised in Methuen, MA, Auditor DiZoglio is a product of Massachusetts public schools. After graduating from Methuen High School, DiZoglio attended Middlesex Community College before earning a financial scholarship to Wellesley College. Her career in public service began as an aide in the State Legislature and as Chief of Staff for the Professional Fire Fighters of Massachusetts. After years of working with local nonprofits and community organizations, she successfully ran for public office in 2012, serving three terms as State Representative for the 14th Essex District. In 2018, she was elected State Senator for the 1st Essex District, where she served two terms.

DiZoglio's decade-long service on Beacon Hill has equipped her with the fortitude to collaborate with elected officials, labor organizations, community advocates, and residents across the Commonwealth. Her humble beginnings and extensive experience in nonprofits and labor have enabled her to build strong relationships with a diverse array of people, amplifying their voices in government.

Throughout her career, DiZoglio has remained driven by a profound commitment to equity and public service. In a recent CommonWealth Beacon article, DiZoglio stated, “These are gaps in the system that we can help to identify. We can raise that to legislators. We can let them know about where these challenges exist for the purposes of improving the system and helping the Legislature to work better for those it’s meant to serve.” Through her work as Auditor, she is dedicated to creating a more inclusive and accountable government for all.

Prior to recording this episode, Auditor DiZoglio embarked (and completed) a 141-mile walk across Massachusetts to raise awareness for ballot Question 1, which would give the state auditor the authority to audit the Legislature. In August, DiZoglio told The Boston Globe, “Government is not supposed to operate the way the Massachusetts Legislature is operating right now.” If passed, the state auditor would be given the express authorization to audit the Massachusetts Legislature. In this episode, we’ll discuss her journey to this point, her walk across the Commonwealth, and take a deep dive into the importance of Question 1.

Yvonne Hao, Secretary of the Executive Office of Economic Development for Massachusetts, joins the Boston Speaks Up podcast live on stage at Startup Boston Week 2024.

Hack.Diversity CEO Michelle De La Isla joins the Boston Speaks Up podcast live on stage at Startup Boston Week 2024.

In this special episode of "Boston Speaks Up," host Zach Servideo, founder of Value Creation Labs and a former doorman at the iconic Pour House, teams up with Lee Stabert from "Explain Boston to Me" to explore the ever-changing landscape of Boston’s dive bar culture. This conversation takes listeners deep into the heart of the city, reflecting on how these gritty, beloved spaces have managed to survive—and even thrive—amid Boston’s ongoing transformation.

The episode dives into some fascinating themes, from the history of Boston's dive bars as community hubs to their role in the face of gentrification. Servideo and Stabert discuss the unique vibe of these establishments, reminiscing about their own experiences and the colorful characters that frequent these spots. They also explore the cultural and economic pressures that threaten the existence of these cherished institutions and speculate on what the future holds for Boston’s dive bar scene.

Listeners can expect a lively discussion filled with personal anecdotes, insightful commentary, and a genuine love for Boston’s hidden gems. This episode is a must-listen for anyone interested in the intersection of culture, history, and community in one of America’s most dynamic cities.

And as a bonus, don’t miss out on the chance to see "Boston Speaks Up" live on stage at Startup Boston Week. Catch Zach Servideo in action on the live podcast stage on September 10th, where he’ll bring more of these engaging conversations to a live audience.

Guest Mike Farber has played many roles throughout his career, serving as a brand builder, mentor, advisor, partner, and now, co-founder. In his latest career move, Farber has the world’s best interests in mind by co-founding GreenStory, an agency focused entirely on elevating the stories of organizations addressing the climate crisis. Farber is also an advisor at Greentown Labs, the country’s biggest climate tech accelerator based in Somerville, Massachusetts.

Before launching GreenStory, Farber began his career at Schwartz Communications, where he launched scores of companies, guided four clients through successful IPOs and helped many others become acquired. His experience spanned across multiple types of technologies, ranging from consumer to enterprise software to clean energy (which he has always magnetized towards).

Farber helped lead the growth of Schwartz’s San Francisco office in the late 1990s, before moving back to Boston in 1999. At Schwartz, he worked alongside peers who became the founders of LaunchSquad, which was the next stop on Farber’s journey. In 2010, he joined LaunchSquad as a partner where he founded LaunchSquad’s Boston office and helped high-growth companies tell their stories to the world.

Following LaunchSquad, Farber took a sabbatical, de-accelerated, spent time with family and friends, guest lectured at Middlebury College and ideated on the next innovative step he might take. During that time, he wrote on LinkedIn, “One through line I keep re-visiting – as governments become increasingly dysfunctional, businesses and NGOs must take a bigger role in driving positive change. I’m not exactly sure what that means for my next step, but… I’ll be working that out.”

In this episode, we explore how Farber worked it all out, why he believes every part of the economy is changing for the better because of climate, how Massachusetts rocks in climate, the legacy he wants to leave on this planet, and so much more.

Guest Kyle Wallack is an artist-entrepreneur and the founder of Refined Graffiti, and you can learn more about his work at his digital gallery The KW Gallery. After graduating from Endicott College in Beverly, MA, he lived in New York City for several years where his career took off before recently relocating to the Tampa Bay, Florida area. Wallack, inspired by the likes of Banksy and Basquiat among others, has now done work for global phenoms Missy Elliot and Cardi B. His work has inspired millions across the world.

Before becoming the esteemed American contemporary artist we know today, Wallack’s journey was struck with hardship. In 2018, and at just 23 years old, Wallack was diagnosed with cancer of the parotid gland, which required intensive surgery to remove the cancer from his face. After a successful surgery leaving him with more than 600 stitches, Wallack was walking to his apartment when he stumbled across an easel. Wallack of course picked it up, brought it back to his apartment, and the rest was history.

Due to the nature of his surgery, Wallack was informed by his doctors that the blue light produced by phones and TVs were extremely harmful to his health. With no access to electronics for more than a year, and a newfound easel and paint, Wallack’s journey as an artist began. Once Wallack picked up his newly found paintbrush and graffiti can, he never put them down. Painting became Wallack’s outlet, and as a wide-eyed, young, 23 year-old trying to figure it all out, painting allowed him to produce positively during this time of adversity.

Before Wallack had his surgery, he had never dabbled in art in an international way. Afterwards, everywhere he looked inspired him to create. Fast forward to the present day, Wallack has now dedicated his full-time career to being an artist. Through years of repetition, hard work, and grinding, Wallack is now represented by Quidley & Co, a well-respected, full-service gallery that has been representing artists for 30+ years.

In this episode, we explore Wallack’s impact that transcends the graffiti and traditional fine art communities, how he perseveres through all the hardships life throws at him, what he’s creating now, and what he wants his legacy to be.