Equity or Bust Podcast

Equity or Bust
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Every side of a Boston real estate deal — decoded LP investing | Tax strategy | Development

Episodes

  1. Aug 20

    No Guest, No Script: The Business Behind the Build — Equity or Bust Ep. 6

    No guest. No script. Just the two of us. Episode 6 is different: Young and Leo (with Jeff, the civil engineer joining the team) drop the format and talk about what actually running a construction and real estate business feels like — the mindset, the war stories, the clients, and the stuff that usually ends up on the cutting-room floor. It's the most unfiltered episode we've done. Less a lesson, more a look behind the curtain — with a few real takeaways along the way. WHAT'S INSIDE • Why a decade in business quietly rewires how you handle a crisis • The difference between "work" and work you actually enjoy • Field war stories: the "quick" job that ate the whole day, and the fence that "grew into a tree" • When a simple update turns into a $350K remodel • "Updating" vs. "remodeling" a bathroom — why moving the toilet changes everything • How the team actually uses AI to save hours (and exactly where it still fails) • The honest advice on breaking into real estate and construction ABOUT THE SHOW Equity or Bust is the Boston podcast for busy professionals: doctors, engineers, and high earners who would rather build real estate equity than manage properties full time. Hosted by Young (real estate) and Leo (general contractor), we sit down with the operators, lenders, builders, and attorneys who actually do the work in Greater Boston — and, once in a while, just talk shop ourselves. New episodes every other Thursday. Follow: Instagram @equityorbust Listen on Spotify, Apple Podcasts, and YouTube. Disclaimer: This episode is for entertainment and educational purposes only and is not investment, tax, or legal advice. Always consult your own licensed professionals before making decisions. #BostonRealEstate #RealEstateInvesting #Entrepreneurship #Construction #RealEstateLife

  2. Aug 6

    How to Protect Your Real Estate — LLCs, Liens & Asset Protection | Equity or Bust Ep. 5

    The deal is only as safe as the paperwork behind it. In Episode 5 of Equity or Bust, Young and Leo sit down with Jon Spino — a Boston "Super Lawyer" and Boston Magazine top attorney specializing in estate planning, trusts, business law, and real estate. Jon has papered countless deals, and he breaks down the legal machinery most investors ignore until it's too late: LLCs, liens, due diligence, and the wildest things he's seen at the closing table. If you own property in your own name — or you're about to — this one is essential. WHAT YOU'LL LEARN • Why serious investors hold property in an LLC — and the "gold standard" of one LLC per project • How long to keep an LLC open after you sell • The due-diligence checklist before you buy: environmental (21A), title, zoning, and realistic timelines • Why the most painful deals are often the most profitable • How a hidden lien can blow up a closing — and how the IRS can stop a sale • Mechanics liens, unlicensed-contractor disasters, and the worst workmanship they've ever seen • What Massachusetts' new ADU rules mean for quietly adding a unit • How the market has shifted — and why online lenders wrecked so many deals • The strangest clauses ever written into a purchase & sale • Cash for keys: the real art of getting a tenant to leave • The one habit that saves deals: build your team on the acquisition side ABOUT THE GUEST Jon Spino — attorney at Sassoon Cymrot Law, recognized as a Super Lawyer and a Boston Magazine top lawyer in estate planning, trusts, business law, and real estate. Learn more at sassooncymrot.com. ABOUT THE SHOW Equity or Bust is the Boston podcast for busy professionals — doctors, engineers, and high earners who would rather build real estate equity than manage properties full time. We sit down with the operators, lenders, builders, and attorneys who actually do the work in Greater Boston. New episodes every other Thursday. Follow: Instagram @equityorbust Listen on Spotify, Apple Podcasts, and YouTube. Disclaimer: This episode is for educational purposes only and is not legal, tax, or investment advice. Always consult your own licensed professionals before making decisions. #RealEstateLaw #BostonRealEstate #RealEstateInvesting #AssetProtection #PassiveIncome

    How to Protect Your Real Estate — LLCs, Liens & Asset Protection | Equity or Bust Ep. 5

  3. Jul 16

    How to Turn Distressed Hotels Into Apartments — Alex Cartwright | Equity or Bust Ep. 4

    Buy a hotel. Sell apartments. Crank the value. In Episode 4 of Equity or Bust, Young and Leo sit down with Alex Cartwright — economist, former tenured professor, and founder & CEO of Hotel Shift, a national platform that buys distressed hotels and converts them into workforce and attainable housing. Alex breaks down one of the most overlooked value-add plays in real estate: the arbitrage between what a tired hotel sells for and what the same building is worth as multifamily. If you want to understand how real estate value is actually created — and why this niche prints in the least affordable cities — this one is a full playbook. WHAT YOU'LL LEARN • Why hotels trade at higher cap rates than apartments — and how that gap becomes an arbitrage • How a conversion creates "naturally occurring" affordable housing with no formal rent restriction • The two kinds of distressed hotels — big flags vs. "Bob's roadside hotel" — and where to find them • Turning banquet halls and racquetball courts into co-working, dog washes, golf sims, and pickleball • The two biggest infrastructure killers: parking ratios and electrical capacity • A full deal breakdown: a 310-unit Denver hotel bought at ~$29K a unit, converted, and refinanced with HUD for a near "infinite return" • The AMI math behind affordable housing — and the NIMBYism operators quietly face • How an economist and former professor scaled into this niche ABOUT THE GUEST Alex Cartwright — economist, former tenured professor, and founder & CEO of Hotel Shift. Learn more at hotelshift.capital or connect with Alex on LinkedIn. ABOUT THE SHOW Equity or Bust is the Boston podcast for busy professionals — doctors, engineers, and high earners who would rather build real estate equity than manage properties full time. We sit down with the operators, lenders, and builders who actually do the work. New episodes every other Thursday. Follow: Instagram @equityorbust Listen on Spotify, Apple Podcasts, and YouTube. Disclaimer: This episode is for educational purposes only and is not investment, tax, or legal advice. Always consult your own licensed professionals before making investment decisions. #RealEstateInvesting #Multifamily #ValueAdd #HotelConversion #PassiveIncome

    How to Turn Distressed Hotels Into Apartments — Alex Cartwright | Equity or Bust Ep. 4

  4. Jul 2

    How Real Estate Money Actually Gets Raised — Jillian Sidoti ($4B+) | Equity or Bust Ep. 3

    Capital is everywhere. Trust is the deal. In Episode 3 of Equity or Bust, Young and Leo sit down with Jillian Sidoti — a securities attorney who has helped entrepreneurs raise more than $4 billion. Jillian breaks down how real estate money actually gets raised: how to find your true investor, how to design an offer people say yes to, the compliance mistakes that sink first-timers, and the red flags she watches for as an investor herself. If you are a busy professional who wants to invest in — or raise capital for — real estate without the hype, this one is a masterclass. WHAT YOU'LL LEARN • Why "always be in capital-raising mode" is the only right answer to "when do I start?" • Your investor is not a dollar sign: how to find your real avatar (why "50 Cent is an accredited investor" misses the point) • Why the numbers are almost irrelevant — and what actually closes an investor • The 2% offer that filled a raise, and the lesson about calibrating trust to your avatar • The compliance mistakes that put you on the wrong side of securities law • The first step to raising $10M: the capital stack, bridge loans, and rolling closes • The webinar funnel that educates instead of hard-selling • Two red flags every LP should watch for — including the $400K "skin in the game" sleight of hand ABOUT THE GUEST Jillian Sidoti — securities attorney and capital-raising strategist. Learn more: findmoreinvestors.com ABOUT THE SHOW Equity or Bust is the Boston podcast for busy professionals — doctors, engineers, and high earners who would rather build real estate equity than manage properties full time. We sit down with the operators, lenders, and builders who actually do the work in Greater Boston. New episodes every other Thursday. Follow: Instagram @equityorbust Listen on Spotify, Apple Podcasts, and YouTube. Disclaimer: This episode is for educational purposes only and is not legal, tax, or investment advice. Always consult your own licensed professionals before making investment decisions. #RealEstateInvesting #CapitalRaising #PassiveIncome #BostonRealEstate #Syndication

    How Real Estate Money Actually Gets Raised — Jillian Sidoti ($4B+) | Equity or Bust Ep. 3

  5. Jun 18

    From Buying the Lot to Selling the Unit: What Boston Development Actually Looks Like | Leo on Zoning, Abutters & the $200K Surprise

    Boston development deals look identical on the pitch deck. They diverge fast under real underwriting. In Episode 2, we sit down with the operator who actually builds in Southie and Cambridge to decode what happens between buying a Boston site and selling your first unit — a timeline most aspiring developers underestimate by an order of magnitude. From a full year of ISD rejections, neighborhood meetings, and ZBA hearings before a single shovel hits the ground, to the $200,000 electric transformer vault nobody warned you about — this is development from the builder's clipboard, not the pitch deck. Plus: the story of how redrawing a building's front setback turned a hostile abutter into the project's biggest advocate at the ZBA hearing. Good operators move the building. Bad ones move the neighbor. Topics covered: The real Boston development timeline (zoning, ISD, ZBA) Why diversified unit mix clears in months and monoculture takes years The 4 questions that separate operators from wholesalers Eversource's all-electric mandate and hidden infrastructure costs How to work with abutters and neighborhood politics Follow us on Instagram: @equityorbust New episodes every other Thursday.

    From Buying the Lot to Selling the Unit: What Boston Development Actually Looks Like | Leo on Zoning, Abutters & the $200K Surprise

  6. Jun 4

    One of the largest hard money lenders in Boston has a secret. He doesn't borrow a dollar himself.

    Boston's largest hard money lender has fifteen years of underwriting behind him — and a counterintuitive rule: "Where do I get the money?" is the wrong first question. Capital is everywhere. Great deals are rare. In this debut episode, Hussein breaks down what he actually looks for before wiring capital, why most passive investors ask the wrong questions, and how hard money lending works from the lender's side of the table. Whether you're a physician, engineer, or professional exploring your first passive real estate position, this conversation gives you the operator's lens before you ever sign a PPM. Topics covered: Hard money lending in Greater Boston Deal underwriting from the lender's perspective Why capital isn't the bottleneck — deal quality is What LPs should ask before wiring money Follow us on Instagram: @equityorbust New episodes every other Thursday.

    One of the largest hard money lenders in Boston has a secret. He doesn't borrow a dollar himself.
  • 6 Episodes

About

Every side of a Boston real estate deal — decoded LP investing | Tax strategy | Development

Information

  • Creator
    Equity or Bust
  • Years Active
    2026
  • Episodes
    6
  • Rating
    Clean
  • Copyright
    © Equity or Bust
  • Show Website
    Equity or Bust Podcast