The Habits That Drive 80+ Sales a Year with Rich Jenkins - The Long Game - Ep. #105

Eight years, 60 units, and 80+ homes a year. Here's what the market actually looks like from the inside. In this episode of The Long Game Podcast, Ryan sits down with Rich Jenkins, a top real estate agent in Central Massachusetts selling over 80 homes per year and a real estate investor with 60 units across Worcester County, to talk about what the market looks like heading into fall 2026, how buyers and investors are winning right now, and what separates the agents and advisors who build long-term clients from the ones who close a deal and disappear. Ryan and Rich also dig into the investor side of the conversation: how Rich thinks about cash flow versus what most newer investors call cash flow, why his underwriting is more conservative than most banks, and how first-hand experience owning 60 units makes him a fundamentally different advisor for his investor clients than someone who's never been through an eviction, a bad prepay, or a tenant who hasn't paid since November. What You'll Learn: Why joining a team was the highest-leverage move Rich made when he started, and what most new agents get wrong by trying to figure it out alone How Rich protects his lead generation time from 9 to noon, five days a week, and why that consistency is the unsexy thing that actually moves the needle What the Worcester County market looks like heading into fall 2026: more inventory, more buyer leverage, and sellers who still haven't let go of 2021 Why Rich starts every investor conversation with "what's your goal?" instead of "how much money do you have?", and why that question changes everything What cash flow actually means when you account for vacancies, capital improvements, water, sewer, and the boiler that's going to go eventually Why a $10,000 seller credit put toward a rate buydown is almost always worth more than a $10,000 price reduction, and how Rich walks clients through that math What Rich's best clients say about him that he wishes every client knew from day one Why Rich says his job doesn't really start until after closing, and what that looks like in practice If you're buying, selling, or investing in Central Massachusetts and want to understand what an experienced agent and investor brings to the table that most people never even think to ask for, this episode gives you a clear and direct picture of what that actually looks like. Interested in connecting? GUESTS Rich Jenkins REALTOR, Jim Black Group  [email protected] | richjenkins.jimblacksellshomes.com  Instagram: @richjenkinsrealtor HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 [email protected] | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in MA, CT, FL, NC, NH, PA, RI, ME, TN, VT Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Market Shift Overview 00:10 Meet Rich Jenkins 01:59 From Hospitality to Real Estate 03:35 Service Skills That Transfer 05:17 Early Career Lessons 06:07 Why Joining a Team Wins 08:40 Time Blocking Lead Gen 12:52 Building Personal Systems 14:06 Scaling as an Investor 19:07 Investor Advice and Goals 21:11 Investor vs Homebuyer Mindset 23:23 Making Deals Work Today 25:35 Real Cash Flow Explained 27:03 Build the Right Team 27:51 Market Shift Since COVID 29:33 Will Home Prices Drop 30:56 Appraisals vs Purchase Prices 31:41 Hot Price Points and Competition 32:44 Creative Loan Programs Today 36:00 Winter Outlook and Deal Hunting 39:09 Motivated Buyers and Reeducation 40:56 Credits vs Price Cuts 43:32 What Makes a Great Agent 49:18 Closing Questions and Wrap Up