Advertise on podcast: Boston Speaks Up

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.

Guest Nick Cicero is an analyst, entrepreneur and growth expert operating at the intersection of digital media and advertising. He made a name for himself in the 2010s when he founded Delmondo, a social video analytics company. Founded in 2014, Cicero quickly established Delmondo alongside established media measurement companies by introducing numerous industry firsts, including the first enterprise analytics solutions for Snapchat, Instagram Stories, and Facebook Live used by clients such as ABC News, the NFL, WWE, Fox, UEFA, Paramount and more. He and Delmondo also co-produced the first Snapchat Branded Long-Form Ad Series with Marriott Rewards. Raising only a single angel investment round, Cicero steered Delmondo into a profitable startup that garnered millions in revenue, hundreds of loyal customers; and set new industry standards culminating in its acquisition by Conviva in 2018. During his time building Delmondo, Cicero was also a cofounder of TVREV, an analyst business reporting on the convergence of TV and digital media. He partnered on TVREV with a who’s who list of media executives that all participated in Conviva’s angel investment round – Gary Vaynerchuk (VaynerMedia), Jesse Redniss (former WarnerMedia, current founder at Qonsent) and David Beck (current Brightcove COO) – who collectively operated as BRaVe Ventures. Cicero stayed on at Conviva for several years to lead Conviva’s social intelligence business in a VP of Strategy role. At Conviva, Cicero focused on extending their portfolio of measurement products that enable video publishers, sports teams, leagues, and streaming TV providers to get a 360-degree understanding of the viewer journey and grow viewership, engagement, and revenue. He departed Conviva in 2022 to pursue consulting opportunities and explore new entrepreneurial endeavors. He joined the ranks of consulting firm Value Creation Labs (VCL) in 2023, establishing himself in a GTM Lead role for VCL and its partners such as Vevo, Precise TV, PadSquad and T-Mobile. Cicero is a regular speaker at industry trade shows, and is an expert commenter on industry trends such as his analysis of the $5 billion Netflix-WWE deal featured in The Drum. He also has a passion for mentoring the next generation of media entrepreneurs. He’s an adjunct faculty member at his alma mater, the S.I. Newhouse School of Public Communications at Syracuse University, where he recently announced the formation of the inaugural Emerging Leaders Alumni Board of which he plays a lead role. We explore Cicero’s impact on the media innovation community, what he’s up to at VCL, and much more in this latest ‘Boston Speaks Up’ episode.

Guest Kristen Craft is the new Vice President & Business Partner Manager at Fidelity for Startups, one of the largest brokerage firms in the United States, headquartered here in Boston. She’s a major catalyst supporting Fidelity in its efforts to help fill the startup banking void in Boston. Craft is working closely with the team at Shoobx, a Cambridge-based fintech Fidelity acquired in January 2023. Shoobx helps companies with equity and board management, storing and sharing important business information, and bringing together startup leaders, lawyers, and investors in a single collaborative hub. Similar to her previous roles, Craft’s role at Fidelity entails her helping startups navigate the financial moments that matter most: fundraising, cap table management, access to investors; alongside all of the other financial expertise and services that Fidelity has long been known for. Craft is a proven entrepreneur with more than 15 years of experience in enterprise software and digital marketing. With a passion for entrepreneurship, she’s become well known around the Boston startup community for her passionate support of founders and VCs. In her role evangelizing the Boston-area startup community, Craft also recently supported the production of a 2024 AI report from Value Creation Labs – Boston Startups Put AI and Data to Work in Vertical Industries and Enterprises. Craft is also a previous guest of Boston Speaks Up, and folks can learn more about her previous career journey in the episode from 2022. Her past experience includes leadership roles at Animalz, Tettra, Ovia Health Wistia, and Transparent Language, as well as launching her own start-up, Brown Box Storage. In her return to the Boston Speaks Up show, she is eager to share best practices on go-to-market strategy, fundraising, and other vital aspects of the startup journey. Drawing from her decades of experience as a startup operator and angel investor, she's gathered a great deal of wisdom and is enthusiastic about making the startup journey smoother for others.

Barbara Fortier is the CEO of the Girl Scouts of Eastern Massachusetts (GSEMA) where she has over 25 years of experience in the nonprofit sector. Before assuming this role, she served as Chief Operations Officer at GSEMA for an impressive 17 years. Fortier's influence extends beyond her impressive tenure at GSEMA. She is a specialist in volunteer management, fundraising, and female empowerment, making her a sought-after expert in her field. As the CEO of the largest girl-serving organization in Massachusetts and the 10th largest Girl Scout council in the nation, Fortier's mission is to create girls of courage, confidence, and character who contribute positively to the world. Her impact isn't limited to her professional role; it resonates within the Greater Boston community. Fortier is deeply passionate about spreading leadership opportunities to women of all ages and backgrounds. Her commitment to female empowerment shines through every facet of her career and personal life. Fortier recently penned an op-ed in the Boston Business Journal about how Girl Scouts addresses the youth mental health crisis. We explore this topic and much more in this latest ‘Boston Speaks Up’ episode.

Guest Alice Pomponio is the Managing Director at BrightEdge, the venture capital and impact investment arm of the American Cancer Society, where her work is making waves in the fight against cancer. With a passion for economic and health equity, she has built a strong track record of bringing groundbreaking ideas to life, developing cutting-edge technologies, shaping markets, and creating value within these ecosystems. Pomponio's journey through the biopharma industry has tracked alongside many of the industry’s defining moments, earning her the playful title of the ‘Forrest Gump’ of biotech. Through the many ups and downs of the economic cycle, Pomponio has persevered as many professionals would, but for her this is much more than a career path. For Pomponio, this mission is deeply personal. Having lost her mother to cancer and witnessed her family's 14 battles against seven different types of cancer, she is committed to the fight against this deadly disease, all while making health equity a central focus of her work. In her current role as Managing Director at BrightEdge, Pomponio spearheads efforts to fuel the fight against cancer through impact venture capital and patient-centric innovation. BrightEdge was founded by the American Cancer Society in 2019, and is a beacon of hope for the fight against cancer. Pomponio's work at BrightEdge is a testament to the idea that philanthropy can ‘supercharge’ donations. By investing in healthcare startups that blend financial growth with cancer-fighting innovations, Pomponio and her team ensure that every dollar donated has the potential to multiply through the investment process. This not only accelerates the development of life-saving technologies but also supports startups that might otherwise struggle to secure seed funding. On top of her work at BrightEdge, Pomponio is also Vice President of Innovation and Impact Investing at the American Cancer Society, and also serves as faculty at the Massachusetts Institute of Technology, further contributing to the advancement of healthcare and innovation. Pomponio's commitment to her mission is further exemplified by her roles as Board Observer at healthcare-focused companies such as Naveris and Vincere Health. It was an honor to sit down with Pomponio and discuss her inspiring journey and groundbreaking work at BrightEdge, and most importantly, her unwavering dedication to the fight against cancer and health equity.

Senofer Mendoza is the Founder and General Partner at Mendoza Ventures, a woman-owned and the first Latinx-founded VC fund on the east coast. In the ever-evolving landscape of venture capital, Mendoza stands as an innovation economy trailblazer and an advocate for diversity and inclusion. Mendoza has a creative background having previously worked as an interior designer for Parker Torres Design. During her stint at the design house, Mendoza was able to work on some exciting projects, most notable would be her design work for Boston’s beloved Fairmont Copley Plaza. Although Mendoza took pride in her creative abilities, she quickly realized to reach her full potential she needed to take fuel from her passion of bringing equity to women in VC and underrepresented founders around the world. Through Mendoza Ventures, she and her team focus on investments in fintech, AI, and cybersecurity, with diversity playing an important role in their investment decisions – about 90% of their portfolio consists of startups led by immigrants, people of color, and women. Since its founding seven years ago, Mendoza Ventures has raised two funds and had two successful exits. Bank of America Corp. is an anchor investor for the new $100 million fund managed by Mendoza Ventures, announced in January 2023. Mendoza's outstanding contributions have been alluring attention from the Boston community, and beyond. In 2022, Axios Magazine recognized her as one of the five most influential people in Boston. Shortly after, the LA Times honored her firm as a DEI visionary as one of California’s most prominent game-changers and thought leaders in the business world today. Currently, she sits on the NACIE, the National Advisory Committee for Innovation and Entrepreneurship. Mendoza's remarkable journey, from an advocate for diversity to the founder of the groundbreaking Mendoza Ventures, exemplifies her unwavering commitment to driving positive change in the VC landscape. As an influential figure and pioneer, she continues to pave the way for underrepresented voices in entrepreneurship. We were fortunate to sit down with Senofer at Startup Boston Week to discuss her career journey and her vision for a more equitable future for the startup community.