Live From Startup Boston Week 2026: It’s Setting the Bar

This year marked the 10th annual Startup Boston Week hosted by absolute superstar Stephanie Roulic, who somehow always manages to make bringing thousands of attendees together for 100+ free sessions, panels, and networking events look effortless. People from all industries and stages of the startup journey — from idea to IPO — gathered for five days of connection, learning, collaboration, and inspiration from local founders.

Needless to say, we jumped at the opportunity to bring the official Workbar podcast Setting the Bar to the stage at Boston University for a live show. So, ICYMI, we’ve recapped some of the highlights for you.

Before we get started… Are you more of an auditory/visual learner? We totally get it. Sometimes you just wanna pop in your headphones and get in the zone. Feel free to jump straight to the full recordings if that’s more your thing. You can stream both live shows on YouTube, Spotify, Apple — or you can always tune in directly on the Workbar website.

Okay, now that we’ve gotten that out of the way. 😉

A little background on Setting the Bar for any newbies to the pod: It’s a podcast series that takes you BTS of Boston's thriving business scene, exploring the stories, challenges, and triumphs of local entrepreneurs. Hosted by The Carpool CEO herself, Sarah Travers, and content marketing pro Maddie Powers, the podcast features a mix of insightful interviews with business trailblazers and in-depth profiles of some of Workbar's most successful clients.

Part 1 |Guy Pistone and Logan Reilly of Valere 

What does it really take to build and scale a business in the age of AI? In this live episode, Sarah and Maddie sit down with Guy Pistone, Co-Founder and CEO of Valere, and Logan Reilly, Director of Service at Valere, to explore how AI is changing the way startups grow, operate, and build teams.

From whether smaller teams can actually accomplish more with AI to the importance of human connection, the conversation dives into what it means to scale smarter, cut through the AI hype (cough, vibe coding, cough), navigate the ethical responsibilities that come with building AI (we're looking at you, Anthropic 👀), and explore what makes Boston the best in the biz when it comes to all things technology and innovation.

Part 2 |Madi Beumee of Live Like Mad

From career pivots to platonic meet-cutes, this one's all about putting yourself out there, especially as a woman. But don't worry, guys — there's plenty in this one for you, too! Sarah and Maddie sit down with Madi Beumee, content creator and founder of Live Like Mad, to chat about making intentional connections as a Boston transplant, cultivating the work/life blend we love here at Workbar, and turning a passion for exploring the city into a thriving business.

The conversation touches on embracing vulnerability both online and IRL, Madi's concept of celebrating "one big thing" (because not every milestone involves a wedding or a baby! 🤯), and how to use social media to your advantage while staying true to your values. Plus, they get into why quality matters more than quantity when it comes to followers, and the power of finding your people in a new city.

Big thanks to entire Startup Boston crew of volunteers for another incredible week of inspiring ideas and engaging activities. Until next year! 👋

In the meantime, keep the conversation going by subscribing to Setting the Bar on your podcast platform of choice for more inspiring conversations from Boston's business community.