On this episode, the guys are joined by zoning attorney Matt Kiefer to discuss how zoning began, why the current system feels broken, and what reforms might look like. He explains that zoning originated about 100 years ago to bring order to rapidly industrializing cities and protect homeowners, but over time it has become layered with complex rules that often slow development and limit housing. The discussion highlights how detailed regulations and the variance process can empower existing residents to block projects, creating barriers to new housing even in cities that need it. Kiefer suggests shifting toward a more flexible “impact review” model—where projects are evaluated based on their actual effects and mitigation plans—so neighbors can have a voice without having a veto that halts development.

** Edits **

- At minute 9:56 Matt states "The Boston Zoning Code is 4,000 words of text for a city of 700,000 people." The correct language is 4,000 pages.

- At minute 40:27 The Mayor appoints 3 not 4 zoning commissioners at large.

- At minute 40:56 Any resident or property owner can submit a citizen petition—not ten registered voters.

This episode features Nick and Samantha Riccio of Eagle Hill Homes sharing their accidental journey from house hacking and DIY renovations into building a full-scale design-build and development business. They discuss how early hands-on work, social media visibility, and shifting market needs shaped their pivot from pure investing into client-focused construction and larger development projects. The conversation also dives into partnership dynamics, hiring and scaling a team, navigating risk, and balancing client work with long-term goals like growing a rental portfolio. Throughout, Nick and Sam reflect on resilience, perspective, and how unexpected challenges—including major personal ones—reshaped both their business philosophy and approach to life.

On this episode, the guys dive into the realities of running and growing a modern real estate brokerage, especially from a developer’s perspective. They unpack vertical integration, boutique vs. corporate brokerages, and why technology has leveled the playing field while mentorship, networks, and real-world experience still matter most. The conversation also explores new construction sales strategies—from pre-sales timing to thoughtful design decisions—and how brokers can add real value beyond just marketing. Along the way, the crew shares candid hot takes, war stories, and practical insights on what actually helps properties sell in today’s market. 

On this episode, the guys start off with a real-world scam story involving Alibaba, setting the stage for a broader conversation about risk, trust, and sourcing materials in real estate development. Where it does and doesn’t make sense to chase savings—covering everything from furniture and light fixtures to windows, cabinetry, and door hardware—while highlighting common pitfalls around codes, inspections, and false brand premiums. They debate loyalty to brands versus buying direct, arguing that many “high-end” finishes come from the same factories as cheaper alternatives. The episode wraps with hard-earned lessons on trades: never race to the bottom on labor, prioritize specialists, and spend money where people interact with a building every day. 

On this episode, the guys break down the “capital stack” in real estate development, explaining how different layers of financing—senior debt, mezzanine debt, private lending, and equity—fit together to fund a project. The hosts emphasize that bank debt is typically the cheapest and largest portion, but also the hardest to secure without experience, which is why many beginners rely on private lenders or creative structures like seller financing. They discuss the value of debt brokers, who can source better terms and navigate shifting lender appetites across markets. Throughout the conversation, they highlight key loan terms, risk considerations, and practical lessons learned from their own development projects.

On this episode, the guys discuss a wide range of topics using a “low-key hot takes” approach. The hosts debate topics like why pocket doors, overused recessed lighting, excessive LED strips, and traditional hardwood flooring are overrated, while defending practical alternatives such as engineered flooring, Hardie siding, bidet toilets, and thoughtful lighting design. They also touch on construction best practices, window installation myths, energy efficiency metrics like HERS ratings, and the realities of modern building codes. The conversation wraps with forward-looking takes on robotics, home technology, and how changing standards are reshaping housing and everyday living.

Garrett Hogan of OnPoint Companies returns to discuss recent Boston-area projects, including a unique Brookline property he renovated, sold, and then re-renovated as the new owner’s general contractor. Garrett shares insights on market timing, investment strategy, and balancing risk versus vision, along with lessons learned from affordable housing units, permitting, and all-electric multifamily development in Jamaica Plain. The conversation also covers the end of his long-term business partnership, the realities of real estate collaborations, and his side venture distributing innovative building envelope products like Thermal Buck and Thermal Tight.

The guys reflect on the transition from corporate careers to entrepreneurship in real estate, emphasizing the value of keeping a W-2 job as a financial safety net while building experience. They share personal stories around “house hacking,” early rental strategies, and creative ways to generate income before going all in. The conversation highlights the importance of mentors, strong local networks, and quality relationships over flashy online gurus. Ultimately, the episode underscores a give-and-take mindset—learn from those ahead of you, grow steadily, and send the elevator back down for others coming up behind you.

In this episode, the guys break down the many ways real estate deals actually get sourced, debating which strategies are underrated, overrated, or appropriately valued. They share real-world experiences with MLS deals, off-market opportunities, direct mail, auctions, wholesalers, and personal outreach, emphasizing persistence and relationship-building over gimmicks. The discussion highlights how credibility, follow-through, and human connection often matter more than automation or flashy marketing tactics.

In this episode, the guys are joined by Chris Guimond, founder and CEO of Modern Mill, about Acre—an innovative, wood-alternative building material made from upcycled rice husks. Chris explains how the product is manufactured, why it offers a sustainable solution to deforestation, and how it compares to traditional hardwoods in durability, ease of installation, and maintenance. The conversation also explores Modern Mill’s rapid growth, partnerships with major brands, and the broader entrepreneurial journey behind scaling a U.S.-based manufacturing company. The episode closes with insights into future applications of Acre and how builders and architects can integrate the material into both exterior and interior projects.