{"id":21110,"date":"2026-07-28T02:03:55","date_gmt":"2026-07-28T02:03:55","guid":{"rendered":"https:\/\/imsfund.com\/?p=21110"},"modified":"2026-07-28T02:03:55","modified_gmt":"2026-07-28T02:03:55","slug":"deal-diary-9-years-39-doors-and-20k-a-month-in-cash-flow-heres-how-jefferson-simmons-built-his-portfolio","status":"publish","type":"post","link":"https:\/\/imsfund.com\/index.php\/2026\/07\/28\/deal-diary-9-years-39-doors-and-20k-a-month-in-cash-flow-heres-how-jefferson-simmons-built-his-portfolio\/","title":{"rendered":"Deal Diary: 9 Years, 39 Doors, and $20K a Month in Cash Flow\u2014Here&#8217;s How Jefferson Simmons Built His Portfolio"},"content":{"rendered":"<p> <br \/>\n<\/p>\n<div id=\"post-content\" :class=\"{ 'hidden': $store.proContent.showFullPrompt() }\">\n                            <!-- Table of contents: mobile --><\/p>\n<section class=\"px-4 relative border border-slate-200 mobile-toc lg:hidden\" x-data=\"{open:false}\">\n                    <button x-on:click=\"open = !open\" class=\"flex items-center gap-4 my-2 border-none w-full\"><br \/>\n                        <svg xmlns=\"http:\/\/www.w3.org\/2000\/svg\" class=\"h-6 w-6\" fill=\"none\" viewbox=\"0 0 24 24\" stroke=\"currentColor\" stroke-width=\"2\"><path stroke-linecap=\"round\" stroke-linejoin=\"round\" d=\"M4 8h16M4 16h16\"\/><\/svg><\/p>\n<p class=\"font-semibold text-slate-800 text-base m-0 js-toc-ignore\">In This Article<\/p>\n<p>                    <\/button><\/p>\n<\/section>\n<table>\n<thead>\n<tr>\n<th>\n<p style=\"text-align: left;\">Name<\/p>\n<\/th>\n<th style=\"text-align: left;\">Jefferson Simmons<\/th>\n<\/tr>\n<\/thead>\n<tbody>\n<tr>\n<td><span style=\"font-weight: 400;\">Location<\/span><\/td>\n<td><span style=\"font-weight: 400;\">Manhattan, Kansas<\/span><\/td>\n<\/tr>\n<tr>\n<td><span style=\"font-weight: 400;\">Occupation<\/span><\/td>\n<td><span style=\"font-weight: 400;\">Full-time real estate investor (former underwriter, Realtor, and university fundraiser)<\/span><\/td>\n<\/tr>\n<tr>\n<td><span style=\"font-weight: 400;\">Assets<\/span><\/td>\n<td><span style=\"font-weight: 400;\">17 properties, 39 doors, $20,000\/month in cash flow<\/span><\/td>\n<\/tr>\n<tr>\n<td><span style=\"font-weight: 400;\">Investment strategy<\/span><\/td>\n<td><span style=\"font-weight: 400;\">Single-family and small multifamily buy-and-hold, BRRRR-style renovation, creative seller, and private financing<\/span><\/td>\n<\/tr>\n<tr>\n<td style=\"text-align: left;\"><span style=\"font-weight: 400;\">Financing<\/span><\/td>\n<td>\n<p style=\"text-align: left;\"><span style=\"font-weight: 400;\">Parental co-sign, family JV equity, private money line of credit, seller financing<\/span><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><em><span data-preserver-spaces=\"true\">Jefferson Simmons was 20 years old and about to be homeless. His entire fraternity house was getting renovated, and every rental in town wanted nothing to do with a group of college guys.\u00a0<\/span><\/em><\/p>\n<p><em><span data-preserver-spaces=\"true\">On a whim, he flipped a Zillow toggle from rent to buy and found a mismarketed three-bedroom house that was actually a 2,700-square-foot property with three extra rooms in the basement.<\/span><\/em> <em><span data-preserver-spaces=\"true\">He pitched his parents <\/span><span data-preserver-spaces=\"true\">to co-sign<\/span><span data-preserver-spaces=\"true\">, negotiated the seller down <\/span><span data-preserver-spaces=\"true\">seven<\/span><span data-preserver-spaces=\"true\"> rounds to $178,000, and moved his fraternity brothers into the basement.<\/span><span data-preserver-spaces=\"true\">\u00a0<\/span><\/em><\/p>\n<p><em><span data-preserver-spaces=\"true\">Nine years later, he\u2019s walked away from law school, built partnerships with an uncle and a private investor, and grown that first accidental deal into 17 properties and 39 doors.<\/span><\/em><span data-preserver-spaces=\"true\">\u00a0<\/span><\/p>\n<p><em><span data-preserver-spaces=\"true\">Here\u2019s how he built it.<\/span><\/em><\/p>\n<h2><span data-preserver-spaces=\"true\">You were a sophomore in college, with no income and no credit. How did you actually get that first house?<\/span><\/h2>\n<p><span data-preserver-spaces=\"true\">I\u2019d saved money since high school from selling firewood and doing livestock projects, and I got a full academic scholarship right before graduation, so I had a nest egg but no income a bank would lend against.\u00a0<\/span><\/p>\n<p><span data-preserver-spaces=\"true\">I went home and pitched my parents using an Excel spreadsheet and<\/span><span data-preserver-spaces=\"true\">\u00a0<\/span><span data-preserver-spaces=\"true\">a full 10-year pro forma showing rent increases, and they agreed to co-sign.<\/span> <span data-preserver-spaces=\"true\">I negotiated the seller down from their asking price to $178,000 over seven rounds of back-and-forth, partly because I knew from the listing agent that the family was highly motivated to sell,<\/span><span data-preserver-spaces=\"true\">\u00a0and partly because I genuinely had no more room to go higher.<\/span><span data-preserver-spaces=\"true\">\u00a0<\/span><\/p>\n<p><span data-preserver-spaces=\"true\">My mortgage payment has stayed the same the whole time, about $1,300 a month, including taxes and insurance. I rented it the first year for $1,600, and it\u2019s currently leased through 2027 at $3,100 per month.<\/span><\/p>\n<div class=\"justify-center \" x-data=\"{ IabAdad_block_: popAd(['r720x90'], '1') }\" :class=\"IabAdad_block_.linkURL ? 'flex pt-8' : 'hidden'\">\n    <a x-show=\"https:\/\/www.biggerpockets.com\/blog\/IabAdad_block_.linkURL\" :href=\"https:\/\/www.biggerpockets.com\/blog\/IabAdad_block_.linkURL\" x-on:click=\"adClicked('https:\/\/www.biggerpockets.com\/blog\/deal-diary-jefferson-simmons', IabAdad_block_.sponsor, IabAdad_block_.title, IabAdad_block_.id, 'blockAdClicked', 'blockAd', 'postContent')\" target=\"_blank\" x-init=\"adLoaded('https:\/\/www.biggerpockets.com\/blog\/deal-diary-jefferson-simmons', IabAdad_block_.sponsor, IabAdad_block_.title, IabAdad_block_.id, 'postContent')\" x-intersect:enter.once=\"adViewed('https:\/\/www.biggerpockets.com\/blog\/deal-diary-jefferson-simmons', IabAdad_block_.sponsor, IabAdad_block_.title, IabAdad_block_.id, 'blockAdViewed', 'blockAd', 'postContent')\"><\/p>\n<div class=\" hidden sm:block\">\n        <img class=\"m-0\" :src=\"https:\/\/www.biggerpockets.com\/blog\/IabAdad_block_.r720x90\" :alt=\"IabAdad_block_.r720x90Alt\" loading=\"lazy\" fetchpriority=\"low\"\/>\n      <\/div>\n<div class=\"block sm:hidden\">\n          <img class=\"m-0\" :src=\"https:\/\/www.biggerpockets.com\/blog\/IabAdad_block_.r320x50\" :alt=\"IabAdad_block_.r320x50Alt\" loading=\"lazy\" fetchpriority=\"low\"\/>\n        <\/div>\n<p>          <\/a>\n  <\/div>\n<h2><span data-preserver-spaces=\"true\">Your second deal was a foreclosure auction property you bought with your uncle. How did that partnership actually work?<\/span><\/h2>\n<p><span data-preserver-spaces=\"true\">I saw a duplex next door to my first house heading to a bank foreclosure auction, and I had zero money to buy it myself. My uncle, who\u2019d built a portfolio of his own and was a big mentor to me, agreed to fund it as a money partner.\u00a0<\/span><\/p>\n<p><span data-preserver-spaces=\"true\">We could only look through the windows before the auction since we couldn\u2019t access the interior, so we did our underwriting from the driveway over coffee, and he told me we could afford up to $140,000 after repairs. Then he left the country on a trip and told me he\u2019d be completely unreachable, so I was the one bidding live from my laptop.\u00a0<\/span><\/p>\n<p><span data-preserver-spaces=\"true\">I got it to $100,000, and even though it didn\u2019t technically meet the bank\u2019s reserve, they wanted it off their books and took the offer anyway.<\/span><\/p>\n<h2><span data-preserver-spaces=\"true\">You walked away from law school after one semester to go all-in on real estate. What made you pull the trigger?<\/span><\/h2>\n<p><span data-preserver-spaces=\"true\">I sat in my first law school class, and they described the bell curve of graduates, meaning that where you rank determines your salary. I realized I wasn\u2019t going to be at the top of that curve, and I\u2019d be leaving school with over $100,000 in student loan debt for the privilege.\u00a0<\/span><\/p>\n<p><span data-preserver-spaces=\"true\">I\u2019d already closed two real estate deals by that point and had real proof of concept, so I decided I\u2019d rather take on another mortgage that pays me back than debt that doesn\u2019t. I left after one semester, worked as an insurance underwriter making $42,000 a year, got my real estate license on the side, and kept buying single-family homes for years while working two jobs.<\/span><\/p>\n<h2><span data-preserver-spaces=\"true\">You\u2019ve done some creative financing since then, including turning a house sale into a line of credit. Walk us through that deal.<\/span><\/h2>\n<p><span data-preserver-spaces=\"true\">I was working as an agent for a cash-buyer client during an insane seller\u2019s market where every listing was already pending within hours. He was getting frustrated that we couldn\u2019t move fast enough on anything.\u00a0<\/span><\/p>\n<p><span data-preserver-spaces=\"true\">Around the same time, tenants in a house I owned asked to break their lease early to buy their forever home, and I let them out of it. That left me with a vacant house I knew fit exactly what my client wanted.\u00a0<\/span><\/p>\n<aside class=\"my-10 xl:my-4\">\n<p class=\"font-bold mt-0 mb-4 text-xl text-slate capitalize\">You might also like<\/p>\n<\/aside>\n<p><span data-preserver-spaces=\"true\">Over dinner, I gave him two options: I\u2019d sell it to him for $25,000 more than I paid, or I\u2019d sell it to him at my exact cost if he\u2019d write me a $200,000 private line of credit instead. He laughed, looked at the house with his wife over FaceTime, and agreed to the line of credit.\u00a0<\/span><\/p>\n<p><span data-preserver-spaces=\"true\">Three months later, I used it to buy a $171,000 house, and he wired the full balance the day of closing with no appraisal and no bank fees. I pay him 7.25% interest, which beats his T-bill returns and costs me less than a bank would. We\u2019ve since done several more deals together and become genuine friends.<\/span><\/p>\n<h2><span data-preserver-spaces=\"true\">What does your portfolio look like today, and what\u2019s actually driving your growth now?<\/span><\/h2>\n<p><span data-preserver-spaces=\"true\">I\u2019m at 17 properties, 39 doors total, and I own all of them outright except for a minority stake in a 15-unit I hold with a few partners. <\/span><span data-preserver-spaces=\"true\">Altogether<\/span><span data-preserver-spaces=\"true\">, that\u2019s about $20,000 a month in cash flow.\u00a0<\/span><\/p>\n<p><span data-preserver-spaces=\"true\">A big unlock along the way was sweat equity: I helped my uncle renovate a 12-unit he bought in 2019, doing new kitchens, floors, and paint myself, in exchange for a 10% stake, which let me build <\/span><a class=\"editor-rtfLink\" href=\"https:\/\/www.biggerpockets.com\/blog\/what-is-home-equity\" target=\"_blank\" rel=\"noopener\"><span data-preserver-spaces=\"true\">equity<\/span><\/a><span data-preserver-spaces=\"true\"> without putting up much of my own cash. I also stopped thinking I could only buy one house a year by saving for the next down payment, since that mindset was actually limiting how fast I could scale.\u00a0<\/span><\/p>\n<p><span data-preserver-spaces=\"true\">Between the family partnership, the private line of credit, and just getting comfortable asking people directly for capital, that\u2019s what let me go from one deal a year to where I am now.<\/span><\/p>\n<\/p><\/div>\n<p><br \/>\n<br \/><a href=\"https:\/\/www.biggerpockets.com\/blog\/deal-diary-jefferson-simmons\" target=\"_blank\" rel=\"noopener\">Source link <\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>In This Article Name Jefferson Simmons Location Manhattan, Kansas Occupation Full-time real estate investor (former underwriter, Realtor, and university fundraiser) Assets 17 properties, 39 doors, $20,000\/month in cash flow Investment strategy Single-family and small multifamily buy-and-hold, BRRRR-style renovation, creative seller, and private financing Financing Parental co-sign, family JV equity, private money line of credit, seller [&hellip;]<\/p>\n","protected":false},"author":5,"featured_media":21111,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"default","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","ast-disable-related-posts":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center 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