A clothing store that accepted tire returns is now a 127-year restaurant empire.

Will Silverstein is the 5th-generation owner of Servedwell Hospitality, the New Bedford-based group behind Black Whale, Candela, Sail Loft, Not Your Average Joe's, and National Club. We cover the Silverstein family's philosophy of hospitality over service, how Not Your Average Joe's scaled to 28 locations across six states before his father sold the franchise side, and Will's decision to leave New York City fine dining and return home during COVID. We also get into employee retention, doubling down on bad guest experiences to build loyalty, DoorDash's 30% commission reality, and where Servedwell is eyeing expansion next.

If you run a business that lives and dies on client experience, this one is for you.

Servedwell Hospitality: https://www.servedwellhospitality.com/

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Chapters:

00:00 - How a 127-year family business stays relevant today

09:12 - Why chain restaurants are dying and what replaced them

17:44 - How to build a restaurant concept around a space

26:50 - Why Servedwell is slowing down before expanding

32:09 - What DoorDash actually costs restaurant owners

We're turning the mics over to the next generation. This week, we’re joined by our boys Liam Miles, Austin Snell, and Owen Snell for one of the most chaotic and entertaining episodes we've ever recorded! The kids answer the tough questions: What do your dads actually do all day? What makes them mad? What animal are they most like? Then we get into Liam's sports card hustle and even rip a few packs. Whether you're a mortgage professional, a card collector, or just interested in hearing Owen talk about Super Mario - this one's for you.

Follow @liamssportscards on Instagram: https://www.instagram.com/liamssportscards/

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Mortgage Daddies on Instagram: https://www.instagram.com/mortgagedaddies/

Mortgage Daddies on Tiktok: https://www.tiktok.com/@mortgagedaddies?lang=en

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Chapters:

0:00 – Welcome to Mortgage Daddies

01:45 – Mario Talk with Owen Snell

05:44 – What’s It Like to be the Son of a Mortgage Daddy?

14:36 – Favorite Person at Milestone (Besides Dad)

17:14 – Rapid Fire Questions with the Kids

30:21 – Liam's Sports Cards

35:07 – Live Card Break

51:55 – Sign Off

This week, we’re joined by Scott Crook, a veteran sales leader from Salesforce. Scott’s here to discuss the parallels between our industries - elite tech sales and the high-volume mortgage business. Scott tells us about the wild pace of the tech industry and the path he took on his rise to corporate sales success. We’re talking about real life too: parenting, the importance of grit and work ethic, and a little regularly-scheduled youth sports talk too. Enjoy!

Milestone Mortgage Solutions: https://milestonemortgagesolutions.com/

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Mortgage Daddies on Instagram: https://www.instagram.com/mortgagedaddies/

Mortgage Daddies on Tiktok: https://www.tiktok.com/@mortgagedaddies?lang=en

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Chapters:

00:00 Welcome to Mortgage Daddies

04:50 The Grind is Never Enough

10:15 Working for a Gigantic Company and Scott’s Sales Background

15:55 Dad Life

18:25 On Demanding Careers

25:30 Personal Life and Goals

34:45 Youth Sports

This week, we’re joined by Milestone’s very own Rob Serpa: a powerhouse loan officer who quadrupled his annual volume to over $28 million in just two years. Rob highlights the power of a competitive mindset and why every top producer needs to "wake up poor." We’re also talking Mission 22, a non-profit dedicated to ending veteran suicide that Rob supported by donating from every single one of his 2025 closings. This one’s a must-watch if you want to learn to scale production while maintaining discipline and authenticity.

Visit Mission 22 at https://mission22.org/

Milestone Mortgage Solutions: https://milestonemortgagesolutions.com/

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2025 is officially in the books, and it was a banner year at Milestone Mortgage Solutions! We’re recapping our awesome year and setting a new goal: $1.1 billion in 2026. This episode is us pulling back the curtain on how we scale our mortgage brokerage. We also move beyond the numbers to talk about the philosophy that drives our success: Doing the right thing when no one is looking. We believe character is what ultimately builds a billion-dollar company - and you certainly can’t overlook it.

Milestone Mortgage Solutions: https://milestonemortgagesolutions.com/

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This week, we’ve got a true OG of the Milestone family: Patrick Walsh of Whaling City Title & Closing. If you’re in the real estate industry and think business ends at 5:00 PM, Patrick’s here for a reality check! Whaling City Title & Closing is one of the strongest title companies in Massachusetts, built by being available when others weren't - no days off.

Whether you’re a loan officer, a realtor, or a homebuyer, you’ll learn why the "quarterback" of your closing is the most important person in the room.

Whaling City Title & Closing: https://www.facebook.com/walshtitleandclosing/

Milestone Mortgage Solutions: https://milestonemortgagesolutions.com/

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In this unplugged episode, we’re stepping away from interest rates and loan guidelines to discuss the personal side of being high-producing mortgage professionals: the balancing act of family, health, and parenting. As high-producing mortgage brokers, the 24/7 grind is real, but as dads and husbands, the home-base is what matters most.

Milestone Mortgage Solutions: https://milestonemortgagesolutions.com/

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Mortgage Daddies on Tiktok: https://www.tiktok.com/@mortgagedaddies?lang=en

Thinking about getting into the mortgage business? Vernon and Craig are here with the inside scoop on what it actually takes to become a top-producing loan officer. We’re moving past the fancy cars and nice clothes to talk about the reality of the industry. Whether you’re a 20-year veteran or just starting out, this episode is packed with everything you need to hear if you want to be in the 1%.

Milestone Mortgage Solutions: https://milestonemortgagesolutions.com/

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Follow us:

Mortgage Daddies on Facebook: https://www.facebook.com/mortgagedaddies/

Mortgage Daddies on Instagram: https://www.instagram.com/mortgagedaddies/

Mortgage Daddies on Tiktok: https://www.tiktok.com/@mortgagedaddies?lang=en