This week, on Everybody Needs a Nudge, Dan & Keith sit down with Steve “Sleepy” Brandt: Dan’s cousin, lifelong athlete, and now an entrepreneur on a mission to make communities more insurable.

Steve opens up about his journey from a hockey-loving kid in Hanover to failing out of college, then returning to UMass Boston and graduating decades later, eventually going from dropout to keynote speaker. Along the way, he built a career in corporate sales, met his wife Natalie, raised two sons, and most recently pivoted to a career as Chief Development Officer and Founding Board Member of InnSure.

We also dive into:

The wild sayings kids use today (ever heard “6, 7”?)

Lessons from survival mode & entrepreneurship

Why it’s important to strive for the standard regardless of the situation

…plus some classic dad jokes 😂

Tune in now and get nudged!

In this nostalgic and laughter-filled episode, Dan and Keith sit down with Kirk Douglas—no, not the actor, but a local legend with a life story as dynamic as his name. Raised in Abington, Kirk shares his journey from playing every sport imaginable to becoming a standout lacrosse player. From getting banned from soccer for life to being transformed by Coach McCabe at Bridgton Academy, Kirk’s path is full of surprising turns, lasting friendships, and lessons learned.

Kirk reflects on the importance of community, the value of following your gut, and how he met his wife Judy in true rom-com fashion—on the train. Now living in Marshfield and vacationing in Vermont with their two kids, Kirk is a tattooed outdoorsman who spends his time hiking, biking, and playing men’s league hockey.

The guys also dive into dad jokes, the Hoover Dam, and Dan’s sentimental goodbye to his Jeep. It’s an episode packed with heart, humor, and a few nudges in the right direction.

In this episode of Everybody Needs a Nudge, hosts Dan and Keith catch up with the Crowd Lending crew and drop some exciting news — the podcast has officially gone international! From DJ Nudgey Nudge spinning tracks to gym comebacks and everyday pet peeves, the boys cover it all. They dive into the spectacle of an NBA game, reflect on this day in history, and keep the laughs coming with their signature dad jokes. Tune in for laughs, insight, and a little bit of everything in between!

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