- Three Interesting Things (in the Boston Startup space)
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- Three Interesting Things (in the Boston Startup Space)
Three Interesting Things (in the Boston Startup Space)
Nathan Therrien
April 21, 2025
I’m Nathan Therrien, founder of Business Insurance & Benefits Services of MA, the go-to resource for #startups on all things insurance.
I spend a lot of time discussing insurance and employee benefits for startups, but there are other things people would rather hear about. So, I started a newsletter—a quick read covering five things and a few more that are a little more interesting than insurance.
This week, we have some cool startup events, including a Techstars alumni and applicant mixer. We also have some newsworthy articles, including one about a fuel startup gaining a $25 M+ grant, and a wildcard podcast with Chris Madden, founder of Stump.
Events:
Learn What’s New with Techstars at the Boston Alumni & Applicant Mixer
Tuesday, April 22, 5:30-7:30 pm
Techstars is rolling out new investment terms with increased capital, higher founder ownership, and stronger early-stage support, with Rho sponsoring the event. Whether you're already part of the Techstars #Boston network or prepping an application, meet the team, swap insights with alumni, and hear what this new deal means for your next steps.
Explore the Future of AI with Founders, Investors, and Experts
Thursday, April 24, 5:00-8:00 pm
Microsoft New England Research & Development Center – 1 Memorial Dr, Cambridge, MA 02142
Get a front row seat to the next wave of #AI at the AI Startup Showcase hosted by Boston New Technology (BNT). The evening features a Town Hall with investors, operators, and experts unpacking trends in generative models, ethics, and scaling #startups. Stick around for live demos from six early-stage teams building in NLP, computer vision, and more with pizza and plenty of networking.
Thursday, April 24, 5:30-7:30 pm
The VC Village Happy Hour is back, featuring a mix of early-stage VCs, angels, LPs, and Fund of Funds investors gathering to swap deal flow and insights over drinks. Expect candid conversations about the wild world of investing in #startups. Sponsored by Leader Bank and Baker Tilly US.
Pitch Live, Get Feedback, and Level Up at Batter Up!
Thursday, April 24, 6:00-9:00 pm
Boston, MA
Join #founders as they pitch live to a panel of investors from Hustle Fund’s Angel Squad at Batter Up Boston. This in-person event offers real-time feedback, networking, and insights into the fundraising process. Presented by Hustle Fund, with support from Nelson Mullins and Fidelity Private Shares, it's a night of startup growth and community.
Fireside Chat on AI, Fintech, and Go-To-Market Strategy with Katy Nelson from a16z
Friday, April 25, 3:00-4:00 pm
Boylston Hall – Cambridge, MA 02138
Harvard WiE is hosting a fireside chat with Katy Nelson, Partner at Andreessen Horowitz and Go to Market lead for fintech, enterprise, and American Dynamism. With nearly 20 years of experience, Katy will dive into how AI is reshaping go-to-market strategies and helping #startups scale in regulated industries. A great chance to hear insights from one of the top GTM minds and meet other founders, operators, and future #entrepreneurs.
Walk Newbury with Startup Founders, Investors, and Operators
Monday, April 28, 5:00-6:00 pm
Boston, MA
Walk #17 brings together #startup founders, operators, and investors for a casual loop from Newbury Street to the Esplanade, ending with drinks. Hosted by Mass Technology Leadership Council, it’s a relaxed way to swap ideas and catch up with others in the community.
Explore AI-Powered Healthcare with Visionary Leaders
Wednesday, April 30, 5:30-8:00 pm
Boston, MA
Get inspired by digital health breakthroughs at Health2Tech in #Boston, featuring Dr. Amir Lahav, founder and CEO of SkyMedAI. Hear his talk on “Vision 2030” and dive into the future of human-AI collaboration in healthcare. Hosted in partnership with C10 Labs, this evening brings together healthcare innovators and tech leaders for networking and fresh ideas.
Explore Agentic AI and Meet the Minds Behind the Movement
Wednesday, April 30, 6:00-8:30 pm
Microsoft New England Research and Development Center – 1 Memorial Dr, Cambridge, MA
The #Boston Generative AI Meetup returns with a spotlight on agentic AI and real-world implementation. Hear from Gregory Raiz of FoundersEdge, Dan Slagen of Tomorrow.io, and James Garfield of EnFi, Inc as they unpack how agentic systems are reshaping automation and decision-making. Stick around for networking, tech talks, and conversations that dive deep into the future of #AI.
Thursday, May 1, 9:30-11:30 am
Cambridge, MA
CIC (Cambridge Innovation Center)’s Social Impact Cohort is spotlighting high-potential #startups led by historically underserved entrepreneurs. This curated investor meetup by Startup Boston is all about targeted networking, matching funders with founders in Pre-Seed to Series A stages. If you're aligned on impact and innovation, this is an opportunity to discover the next big thing.
Pitch Night with AI Startups and Global Investors
Wednesday, May 28, 5:30-8:30 pm
Microsoft New England Research & Development Center – 1 Memorial Dr, Cambridge, MA
Watch 10 top AI startups compete at the Datamellon AI Ignite Pitch Battle in #Boston. This event brings together developers, investors, and #founders for fast-paced pitches, live demos, and networking. With a $100k prize on the line and support from AWS, it’s a big night for innovation in the AI space.
Articles:
Judge Says Google Abused Power in Ad Tech Market
A federal judge ruled that Google illegally monopolized digital advertising technology, siding with the U.S. Department of Justice. The decision could lead to the forced breakup of parts of Google's ad business, signaling a major shift in how regulators tackle tech giants' dominance in online markets.
Rippling Wants Answers in Deel Espionage Saga
Rippling is asking a London judge to force UK fintech giant Revolut to name who paid off the alleged corporate spy caught at Deel. The legal twist adds a new layer to the battle between two of the fastest-growing HRtech startups, raising questions about how far competition in the startup world can go.
Mass. Grants $25 M+ to Fuel Startup Growth
The Healey-Driscoll administration just awarded over $25 million to support 13 organizations accelerating #startup and tech commercialization efforts across Massachusetts. The funding backs programs focused on regional entrepreneurship, advanced manufacturing, and climatetech, underscoring the state’s commitment to building out its innovation economy.
Wild Card:
🚨 Founder Spotlight 🚨 Founder Spotlight 🚨
Stump is on a mission to Democratize Democracy!! Check out how #founder Chris Madden is going to improve local government (boy do we need it). In the most recent episode of my Pop-Up Podcast, Stump founder Chris Madden joined me to talk about his startup journey.
In the clip, Chris gives a two-minute elevator pitch on the mission to improve local government through Stump.
This 2nd clip has the entire interview with Chris
Thanks for spending five minutes with me!
If you’d like to spend more time with me, check out Nate’s Pop-Up Podcast, follow my company, Business Insurance & Benefits Services of MA, on LinkedIn, or reach out through my website for help with all things insurance and benefits for startups.
