Investor Insights, Venture Building, AI Prototypes: Boston Speaks Up Live at Startup Boston Week

For the third year running, Boston Speaks Up took over the Startup Boston Week stage for a three-hour live podcast marathon. What started as an experiment has become one of my favorite traditions — a chance to bring candid conversations with founders, investors, and builders straight to a live audience.

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.

Episode 107: Steve Walsh + Rob Hughes: The Funding Funnel

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.

Episode 108: Clay Unicorn + Marc Gigliotti + Dylan Wilson: Rethinking Venture Studios

Next up, 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.

Episode 109: AI Happy Hour with Clay, Marc + Justin Bingham

We closed with a live version of our recurring AI Happy Hour, featuring Clay, Marc and Justin Bingham. 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.

Wrapping Up

Three hours flew by. From capital strategy to venture studio models to AI prototyping, the conversations underscored why Boston remains such a dynamic hub for innovation.

Thanks to everyone who joined live, and to Suffolk University for hosting the Startup Boston Week stage. You can listen to the full live sessions on Spotify, Apple Podcasts, SoundCloud, Google Play, Stitcher and just about anywhere you enjoy listening to podcasts.

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You can follow BSU on Twitter, TikTok and Instagram (@BostonSpeaksUp), and recommend BSU guests by contacting team@valuecreationlabs.co.