Guest Lily Lyman is a General Partner at Underscore VC, a leading Boston venture capital firm known for its Underscore Core Community of proven business builders helping each other succeed. She is also a Board Director for the New England Venture Capital Association, MIT Sandbox Funding Board, and is a leader of the Boston All Raise chapter.

Lyman has a background as a founder, investor, and operator. She came to Underscore VC from Facebook, where she worked in product strategy focused on the international growth of core products including Facebook, Instagram, WhatsApp, and Messenger.
 
Prior to Facebook, Lyman held a variety of strategy, operational, and entrepreneurial roles. Through it all, she has gained a truly global perspective, having lived and worked in more than 75 countries. 

At Underscore VC, Lyman leads investments on Future of Work, AI/ML, Insuretech, Commerce, and more. With experience that spans the globe, she spends her time identifying investment opportunities and guiding startups that will define new digital categories, reshape industries, and change the world. 

On this episode of Boston Speaks Up, we chat with Lyman about her lessons from the past, her bets today and her predictions for the future.

085: Underscore VC's Lily Lyman

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

Entrepreneur or Bust: Zach Servideo Riffs on Workplace Survival

Guest Kiel Servideo is a former Hollywood assistant who’s always found comfort with a pen and a notebook. He moved out to Los Angeles a year after graduating from Boston University where he hustled various temp agency jobs before landing full-time gigs with Hollywood titans such as Jerry Bruckheimer and Shawn Levy. While living in LA, Servideo wrote his first novel -- The Preposterous Dreams of Tucker Adams -- a fiction documenting a modern tale of the pursuit of Manifest Destiny. 

In the Fall of 2019, Servideo and his wife left their life in Los Angeles and each accepted jobs abroad teaching English to grade schoolers in Seville, Spain. Half way through the school year, a global pandemic changed everything. Servideo spent much of 2020 in lockdown with his wife, utilizing Airbnb to see more of Spain while remaining in isolation. 

Servideo is now living in a 300 year old farm house in Umbria, Italy, and he and his wife are working for DTC nail services startup Olive & June. 

As Servideo continues to life hack the pandemic, he’s discovering authors, reading, writing and reflecting on the divisive politics in America from Europe. We’re grateful to begin 2021 catching up with Servideo for all to hear.

056: Author & Former Hollywood Assistant Kiel Servideo

Leaders, entrepreneurs, creators, innovators and artists from all over the globe join Boston Speaks Up to share their stories of inspiration. Recommend a guest: team@valuecreationlabs.co. Learn more and sign up for the newsletter: www.valuecreationlabs.co.

Entrepreneur or Bust: Zach Servideo Riffs on Workplace Survival

Boston Speaks Up

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