Steve "Sleepy" Brandt

Steve "Sleepy" Brandt

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!

Kirk Douglas

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.

Crowd Lending Catch Up

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! Donate to Madison's Marathon run here! --> https://donate.heroesendurance.org/donations/new?fundraiser=9cbeb851819aefa294d1

Michael Burns

In this episode, Dan and Keith sit down with Michael Burns, a lifelong athlete and Belmont native with a passion for sports and coaching. Michael shares his journey from backyard whiffle ball to Belmont Hill, then on to Trinity College—his dream school—and eventually into a career in sports marketing. After realizing finance wasn’t for him, Michael pivoted back to his passion, earning a degree in sports management from UMass and landing roles with NESN and the Bruins. For the last 18 years, he’s thrived in the industry at Hill Holliday. Now a husband, father of three daughters, and a dedicated coach, Michael reflects on how his upbringing, community, and competitive mindset shaped his life. The guys also chat about country club scuffles, marathon bandits, and mindset versus talent, with a special shout-out to Keith’s episode-winning dad jokes. Tune in now!

Anh Kieu

This week, Dan & Keith sit down with Anh Kieu; Loan Processor, cat mom, and all-around powerhouse. Anh shares her incredible journey from Vietnam to Quincy, MA—learning English on the fly, navigating a new culture, and building a career in finance. We cover everything from mortgage tips to cat backpacks, plus: ✔️ How many exclamation points are too many?!✔️ Hard money vs. conventional loans✔️ Perseverance, teamwork, and knowing your role✔️ Dad jokes, duh. Tune in for laughs, inspiration, and a reminder that sometimes, we all need a little nudge.