Rigs to Riches

Casey Gregersen
  • 5.0 (1)
  • Investing

From oilfields to financial freedom. Rigs to Riches is all about helping hardworking W2 earners—especially in oil & gas—build true wealth through strategic real estate investing. Follow along for real deals, creative financing, and the unfiltered journey from the rig to real estate riches.

  1. 2d ago

    EP35: Jason Medley — Lost Everything at 38, Built The Collective Genius

    At 38, Jason Medley lost his business, his marriage, and nearly his house in the 2008 crash. Today he's the founder of The Collective Genius, a real estate mastermind with 600+ members. He brought in a private equity partner, hired a CEO to replace himself, and now runs nothing day to day. Casey has been a Collective Genius member for four years. In this episode Jason talks about the letter he taped to his bathroom mirror and how he rebuilt with transactional funding. He also covers how he scaled CG from 8 guys in a room to a PE-backed company, and why he thinks the fastest path to passive income is a big active income. If you're a W-2 earner who wants out, or just more, this one is about mindset, discipline, and the right room. ABOUT JASON Jason Medley grew up in Louisville, Kentucky, raised by a single mom, and started his career as a retail mortgage broker in Florida. After the 2008 crash he co-founded iVisionary Financial, a transactional funding company for real estate investors. Around 2011 he founded The Collective Genius. Today he serves as chairman after a partial exit to private equity. CONNECT WITH JASON & THE COLLECTIVE GENIUS Instagram (Jason): https://www.instagram.com/jmedley1/ LinkedIn: https://www.linkedin.com/in/thecollectivegenius Website: https://thecollectivegenius.com Instagram (The Collective Genius): https://www.instagram.com/thecollectivegenius_/ Facebook: https://www.facebook.com/thecollectivegenius/ CHAPTERS 0:00 Rock bottom: "the last time I clean this pool" 0:33 Welcome to Rigs to Riches 1:20 Meet Jason Medley, founder of The Collective Genius 2:26 Raised by a single mom in Louisville, Kentucky 5:05 Mortgage broker in Florida, then the 2008 crash 7:02 Losing the business, the marriage, and the house 8:28 The letter on the bathroom mirror 13:00 Bet on yourself: he hit zero at 38 15:00 Rebuilding: mindset, short sales, and dry closings 16:59 Starting iVisionary Financial 18:16 The birth of The Collective Genius 19:37 Scaling from 25 members to 100 on his own 21:57 Pausing growth, then choosing to scale 22:38 Partnering with private equity and hiring a CEO 24:53 The partial exit: quarterback to coach to owner 26:57 Income vs. enterprise value and founder dependency 29:41 Why writing things down actually works 31:01 The annual legacy letter 33:02 Track everything: metrics, date night, family dinner 35:28 The five Fs: family, fun, finances, faith, fitness 37:57 Seasons of life: balance isn't always an option 39:24 Set non-negotiables with your spouse 40:38 The fastest path to passive income is a big active income 45:15 Productive paranoia and Shell's "chronic unease" 46:57 Advice for W-2 earners: find your room 49:00 Where to find Jason JOIN THE COMMUNITY Want to buy real estate while you keep your W-2? Join the free Revive community: https://www.facebook.com/share/g/1H1y1et7wC/ Listen on Apple: https://podcasts.apple.com/us/podcast/rigs-to-riches/id1895804626 Listen on Spotify: https://open.spotify.com/show/0ZQ4RDbEwBqC2uBn8OqR8r #RigsToRiches #RealEstateInvesting #CollectiveGenius #Mastermind #PassiveIncome

  2. 2d ago

    EP34: Kyle Moore — Advanced Tax Strategies Beyond Your CPA

    A business owner sells his company for $4.2 million and is staring at a tax bill of roughly $1 million. Kyle Moore of Strategic Associates explains how his firm legally wiped that bill out, and why most high earners never hear about strategies like this from their CPA. Casey and Kyle met at a golf mastermind in Austin. In this episode Kyle walks through the five buckets his firm works in: bonus depreciation on private property (not real estate), tax credits, Section 179 equipment, business creation with a master series LLC, and leveraged charitable donations. He explains the difference between tax mitigation and tax evasion and why his team works alongside your CPA instead of replacing them. He also runs real numbers, including a $600K W2 couple in Texas who could put $26K back in their pocket with one year-end move, and a 16-year tax deferral that works a lot like a 1031 exchange. ABOUT KYLE MOORE Kyle Moore is a senior consultant at Strategic Associates, an advanced tax mitigation and consulting firm based in Logan, Utah. The firm works with entrepreneurs, business owners, high-income W2 earners, doctors, lawyers and ranchers. Before joining the firm in 2025, Kyle earned his MBA, consulted with executives at global companies, and co-founded a life insurance and Medicare agency that grew to about 95 agents nationwide before he exited. Family, God and football come first. CONNECT WITH KYLE Book a call with Strategic Associates: https://www.strategicag.net/begin-booking-fb Website: https://www.strategicag.net Learn more: search "Roger Roundy Strategic Associates" on YouTube for short overview videos from their CEO CHAPTERS 00:00 - Cold open: wiping out a $1M tax bill 00:29 - Show intro 01:22 - Meeting Kyle at a golf mastermind 02:34 - Kyle's background: Logan, Utah and an MBA 03:21 - Corporate consulting and 180 nights a year on the road 04:20 - Selling life insurance door-to-door in Wyoming 05:11 - Building a 95-agent agency and exiting in 2025 07:30 - What Strategic Associates does 09:35 - Where a tax strategist fits next to your CPA 11:09 - Tax mitigation vs. tax evasion: the five strategy buckets 12:01 - Bonus depreciation on mini homes for disaster relief 13:46 - Box House units: what you're actually buying 14:36 - Section 179: equipment paid down with reward points 17:18 - Track record and doing your own due diligence 18:10 - Leveraged charitable donations: 1:5 on your dollar 20:33 - Example: $500K income in California 21:25 - The 16-year tax deferral strategy 23:13 - Real example: $4.2M business sale, $1M tax bill 25:11 - What happens when the 16 years are up 26:00 - Funding the strategy with margin loans or an IRA 26:49 - Hypothetical: $600K W2 couple in Texas 29:34 - The same couple using a Box House 30:05 - Done-for-you setup: LLCs, EINs and tax filing 30:55 - Why overpaying taxes isn't patriotic 31:22 - Casey's takeaways 31:44 - Year-end deadlines and how to connect with Kyle 33:14 - Casey's wrap-up This episode is for education only and is not tax, legal or financial advice. Talk to your own CPA and advisors before acting on any strategy. Join the free Revive real estate community: https://www.facebook.com/share/g/1H1y1et7wC/ Subscribe for weekly episodes on building real estate wealth around a demanding career. #RigsToRiches #TaxStrategy #TaxMitigation #BonusDepreciation #W2Income #HighIncomeEarners #CaseyGregersen #RealEstateInvesting #KyleMoore #StrategicAssociates

  3. 4d ago

    EP33: Mat Sorensen — Self-Directed IRAs: Invest Your Retirement in Real Estate

    There's $49 trillion sitting in US retirement accounts, and most of it is stuck in stocks, bonds and mutual funds. Mat Sorensen, attorney, founder of Directed IRA and author of The Self-Directed IRA Handbook, explains how to put those dollars to work in real estate, private lending and other private assets, tax-deferred or tax-free. In this episode Mat and Casey cover what a self-directed IRA actually is and why Fidelity or Schwab won't let you buy the duplex down the street, the three steps to set one up, and the few things your IRA can't own. Mat shares how some clients have grown Roth IRAs from zero to hundreds of millions, and his own "base hit" strategy: private loans at 12% plus two points, twice a year. He breaks down why a 10% return taxed at the top bracket is really about 6%, the ways to fund these accounts (solo 401k, backdoor Roth, HSAs, rollovers), the prohibited transaction rules that trip people up, and why he's watching distressed commercial office right now. ABOUT MAT SORENSEN Mat Sorensen is the founder and CEO of Directed IRA & Directed Trust Company, an attorney and partner at KKOS Lawyers, and author of The Self-Directed IRA Handbook (60,000+ copies sold). He co-hosts the Directed IRA Podcast and the Main Street Business Podcast with Mark J. Kohler, hosts the Self-Directed IRA Summit and the Alternative Asset Investor Summit, and has been featured in the Wall Street Journal, Forbes and Bloomberg. CONNECT WITH MAT Directed IRA (book a free call): https://directedira.com YouTube: https://www.youtube.com/@MatSorensen Website: https://matsorensen.com Book: The Self-Directed IRA Handbook Alternative Asset Investor Summit, Oct 22-23, 2026, Costa Mesa, CA: https://altassetsummit.com CHAPTERS 00:00 - Cold open: growing a Roth account with no cap 00:46 - Show intro 01:16 - Welcoming Mat Sorensen 03:01 - Mat's background (and being a YouTuber dad) 04:18 - How one client question pulled a tax lawyer into self-directed IRAs 05:38 - Starting Directed IRA 07:28 - $49 trillion sitting in US retirement accounts 08:19 - What a self-directed IRA is and why Fidelity won't do it 10:10 - What your IRA can't buy: life insurance, collectibles, S corps 11:16 - Wild IRA investments: cattle and a pro soccer team 13:20 - The three steps to set up a self-directed IRA 15:03 - How much paperwork it really takes 16:20 - Who self-directing is not for 17:10 - Why it fits high-income W2 earners and business owners 18:38 - Home-run Roth IRAs: from zero to hundreds of millions 20:00 - Mat's base-hit strategy: private lending at 12% plus 2 points 21:05 - Why 10% taxable is really 6% after tax 23:29 - Solo 401k, backdoor Roth, HSAs and other ways to fund 25:43 - $19T in IRAs vs $14T in 401ks: putting old accounts to work 28:47 - Biggest mistake: prohibited transaction rules 31:04 - Lesson two: understanding asset cycles 34:19 - Don't bail at the worst time 35:46 - Advice for busy professionals: get engaged and educated 38:55 - Where the opportunity is now: distressed commercial office 41:29 - Being a vulture in distressed real estate 43:34 - Get around people already doing what you want to do 44:52 - The Alternative Asset Investor Summit 46:37 - Where to find Mat and Directed IRA 47:53 - Casey's wrap-up Join the free Revive real estate community: https://www.facebook.com/share/g/1H1y1et7wC/ Subscribe for weekly episodes on building real estate wealth around a demanding career. #RigsToRiches #SelfDirectedIRA #RothIRA #RetirementInvesting #PrivateLending #Solo401k #CaseyGregersen #RealEstateInvesting #MatSorensen #DirectedIRA

  4. 4d ago

    EP32: Jerry Norton — 10 Kids, 21 Years in Real Estate & a Business Built Around Life

    Jerry Norton got started flipping and wholesaling houses in Metro Detroit 21 years ago, accidentally became a teacher when he filled in for a paid speaker at a meetup, and built an online real estate education business from there. He also has 10 kids. In this episode Jerry and Casey get into selling before you build the infrastructure, treating failure like a batting average, and a costly historic-district renovation mistake. Then they go deep on family: investing attention in your kids while they're young, designing a business around your life instead of the other way around, the "arrival fallacy," taking a whole summer unplugged, W2 golden handcuffs, and why Jerry and his wife don't pay for college or leave an inheritance. Jerry Norton is a real estate investor and educator who has flipped and wholesaled houses for 21 years and teaches investors through his online education business. CHAPTERS 00:00 - Cold open: inheritance policy teaser 01:29 - Intro & meeting Jerry Norton 02:10 - Jerry's start flipping and wholesaling houses 03:37 - Accidentally selling a flipping course at a meetup 04:21 - How the education business took off 05:04 - Teaching for a real estate education company 06:39 - Getting flown out to teach for the company 08:03 - Company closing and going out on his own 08:42 - Building an online education business 10:17 - Delegating business to stay active in deals 11:43 - Lesson: sell before you build the infrastructure 13:11 - Handling failure like a batting average 14:39 - Costly historic-district renovation mistake 16:52 - Raising 10 kids while building the business 17:37 - Compartmentalizing vs. balancing family and work 19:59 - Investing attention in kids while they're young 22:10 - Designing a business around life, not life around business 23:57 - The 'arrival fallacy' (a Russell Brunson lesson) 24:49 - Taking an unplugged summer at the lake house 27:25 - W2 golden handcuffs and his father-in-law's regret 30:30 - No college funding, no inheritance philosophy 33:14 - Finding and buying a lake house in Flathead Valley 35:50 - Manifesting the lake house through a written vision 37:29 - Systems, house managers, and home-life infrastructure 42:34 - Current move to a Tennessee farm raising animals 44:00 - Wanting more time freedom for adult kids ahead Join the free Revive real estate community: https://www.facebook.com/share/g/1H1y1et7wC/ Subscribe for weekly episodes on building real estate wealth around a demanding career. #RigsToRiches #JerryNorton #RealEstateInvesting #CaseyGregersen #Wholesaling #FixAndFlip #Entrepreneurship #FamilyFirst #LifestyleBusiness #FinancialFreedom

  5. 4d ago

    EP31: Bella Linchenko — The Airbnb Design Playbook Behind a $120K/Year Cabin

    Bella Linchenko and her husband bought their first property, a ski-resort cabin, at 25, lived in it first to lock in a 2.75% rate, and renovated and designed it themselves. It now does about $120,000 a year, and that design playbook became her business. In this episode Bella and Casey get into the design choices that make a short-term rental outperform its market, designing for your guest avatar, and whether STRs still work in saturated markets. Bella breaks down realistic furnishing budgets, where to spend on high-touch vs low-touch items, Wayfair vs higher-end furniture, and how to choose a designer. They also cover how full-service design pairs with cost segregation and bonus depreciation (often about 35% of the project back), pacing projects around real estate professional status, finding contractors in a new market, and using AI to compare bids. Bella Linchenko is a Salt Lake City-based short-term rental investor and interior designer, founder of Let's Go Design Co., and also runs a mural painting business. CHAPTERS 00:00 - Cold open 01:37 - Welcome back & guest intro: meeting Bella through masterminds 02:18 - Bella's background: fine arts design degree to Airbnb investing 03:01 - Buying the first ski resort property with her husband 04:26 - The ski cabin 'home run': 2.75% rate and the numbers 05:23 - Property cash flow: revenue, costs, and renovation budget 06:03 - Sweat equity, quitting jobs, and going full-time into real estate 06:41 - Design choices that make the ski property perform so well 08:07 - Designing around guest avatars and amenity priorities 09:28 - Hitting ceilings: Airbnb algorithm, reviews, and ROI limits 10:44 - Is short-term rental still a good investment in saturated markets 12:09 - Underrated markets: 2-hour radius towns and Joshua Tree example 12:54 - Mountain town seasonality, regulations, and permit limits 14:22 - Joshua Tree spec-build case study: $1.5M amenity-rich properties 15:05 - Bigger vs smaller properties: which drives more ROI 17:23 - Setting a realistic design/furnishing budget per square foot 19:41 - Wayfair vs higher-end furniture and renovation cost tiers 21:05 - High-touch vs low-touch items: where to spend more on furniture 21:49 - Furniture durability and lifespan for short-term rentals 23:15 - Design service levels: virtual, white-glove, and hybrid models 26:16 - Cost segregation, bonus depreciation, and tax benefits of full-service design 27:37 - Hybrid client types: investor-minded DIYers vs W2 hands-off owners 29:41 - How to choose the right interior designer for your rental 31:49 - Niche vs timeless design and matching style to owner's goals 32:30 - Explaining bonus depreciation savings (~35% back) to the audience 33:50 - Scaling design studio operations and seasonal demand timing 35:12 - Building virtual assistant teams and managing supply chain delays 35:56 - Running two businesses: interior design vs mural painting 36:41 - Pacing one big project per year around real estate professional status 37:26 - Finding reliable contractors in new markets via network and Facebook groups 39:26 - Using AI to standardize contractor bids for apples-to-apples comparison 40:09 - Where to find Bella: Instagram and Let's Go Design Co website Join the free Revive real estate community: https://www.facebook.com/share/g/1H1y1et7wC/ Subscribe for weekly episodes on building real estate wealth around a demanding career. #RigsToRiches #AirbnbDesign #ShortTermRental #InteriorDesign #CostSegregation #CaseyGregersen #RealEstateInvesting #BonusDepreciation #AirbnbHost #STRInvesting

  6. 4d ago

    EP30: Jace Graham — 1,300 Deals, Mineral Funds & Powering AI Data Centers

    Jace Graham started as a landman in 2002, played football at Cornell, and later left his family's oil company, pulling equity out of his house to raise capital for mineral funds. Along the way he did 12,000 quarter-acre land lots and close to 1,300 wholesale and fix-and-flip deals in Dallas with his wife. In this episode Jace and Casey get into how Rising Phoenix runs minerals, real estate and capital raising side by side, how he reverse-wholesales minerals to private equity and hedge funds, and what non-op and PDP assets actually are. Jace explains how AI is cutting reserve-report underwriting from a week to 30 minutes, how he models mineral fund returns if oil drops to $35-$40, what happened to distributions in the last downturn, and the behind-the-meter natural gas project he's building to power AI data centers in the Barnett Shale. Jace Graham is the founder of Rising Phoenix, a Texas company spanning oil and gas minerals and mineral funds, real estate wholesaling and fix-and-flip, seller financing, and capital raising. CONNECT WITH JACE Rising Phoenix Resources: https://www.rising-phoenix.com CHAPTERS 00:00 - Cold open: AI is accelerating oil & gas underwriting speed 01:34 - Intro: Welcome back to Rigs to Riches 02:14 - Jace's background: Cornell, landman work, and early career in Dallas 03:00 - Running title in Colorado, then joining the family oil company 03:47 - Founding Rising Phoenix in 2016 and overview of current business lines 05:09 - Leaving the family company and raising capital for mineral funds 06:44 - Pivoting into real estate wholesaling and fix-and-flip in Dallas 08:10 - Scaling the real estate team and running parallel business lines 09:36 - Marketing differences: real estate direct mail vs. mineral side outreach 10:21 - Cold calling teams in South Africa and lead qualification process 12:30 - In-house underwriting engine for mineral valuation 13:20 - Reverse wholesaling minerals to private equity and hedge funds 15:19 - Buy box strategy, tax write-offs, and non-op investing explained 16:54 - What non-operated (non-op) oil and gas interests actually are 17:40 - PDP (proved developed producing) assets and mineral fund structure 19:59 - Underwriting risk: evaluating rock quality and reserve categories (1P/2P/3P) 22:10 - How AI is speeding up petroleum engineering and reserve analysis 24:38 - Biggest AI opportunity: fast underwriting and finding motivated sellers 27:06 - Example: evaluating a niche play like the Barnett Shale 29:18 - Reverse wholesaling minerals using courthouse deed records 31:21 - Advice for beginners wanting to get into mineral buying 35:41 - Why minerals are an attractive, passive alternative investment 37:11 - Mineral fund return targets and cash flow mechanics 39:29 - Modeling returns if oil prices drop to $40 or $35 a barrel 41:17 - Surviving the Shell-era oil price downturn and fund distribution drops 43:26 - Mineral fund exits compared to multifamily real estate exits 45:31 - Rising Phoenix fund offerings: debt fund, income fund, growth fund 47:40 - Real estate mastermind club and minimum investment amounts 48:21 - Reflecting on Rising Phoenix's pivot from real estate back to oil and gas 49:48 - The AI data center / behind-the-meter natural gas generator project 51:55 - Closing thoughts and where to find Jace and Rising Phoenix Join the free Revive real estate community: https://www.facebook.com/share/g/1H1y1et7wC/ Subscribe for weekly episodes on building real estate wealth around a demanding career. #RigsToRiches #OilAndGasInvesting #MineralRights #CaseyGregersen #RealEstateInvesting #Wholesaling #CapitalRaising #AIDataCenters #NaturalGas #PassiveIncome

  7. 4d ago

    EP29: Rafa Loza — 167 Airbnb Units to $1.85M Builds & the STR Tax Play

    Rafa Loza started with one two-bedroom Airbnb arbitrage unit, had 16 units in 9 months, and peaked at around 167 short-term rental locations, including entire 30-unit apartment complexes he converted unit by unit. Then COVID-era city bans shut locations down, and he pivoted into building. In this episode Rafa and Casey get into how he funded his early growth with credit cards and a $10K loan from a friend, what a city short-term rental ban lawsuit taught him, and how a Joshua Tree builder partnership led to a home that sold for $1.85M. Rafa breaks down how he raises private money at a 16% return, then walks through the short-term rental tax strategy for W2 earners: material participation, the 100-hour rule, cost segregation and bonus depreciation, why so many CPAs get it wrong, and how to document hours so it holds up. Rafa Loza is a short-term rental operator and developer who builds amenity-rich vacation homes and boutique hotel projects, funded with private money. CONNECT WITH RAFA Instagram: https://www.instagram.com/itsrafaloza/ The AI B&N Blueprint (Skool community): https://www.skool.com/the-airbnb-blueprint-rafaloza/about Invest with Rafa: https://aurumcoastcapital.com CHAPTERS 00:00 - Cold open: depreciation recapture tax strategy teaser 00:33 - Show intro: Rigs to Riches podcast format 01:17 - Welcoming Rafa Loza and catching up 02:02 - Rafa's background: starting short-term rental arbitrage 03:19 - Scaling into boutique hotels and development 04:02 - First deal numbers and early scaling timeline 05:31 - Hiring first help and building automation systems 06:13 - Raising capital via credit cards and friends 06:46 - Taking over 30-unit apartment complexes for arbitrage 08:03 - Peak of 160+ locations and COVID-era shutdowns 09:58 - City short-term rental ban, lawsuit, and pivot decision 11:16 - Clarifying the arbitrage vs ownership model 11:57 - Operations: furnishing, designers, and listing optimization 13:48 - Leadership lessons after team problems and turnover 15:36 - Apartment complex conversion process in detail 16:16 - Partnering with a builder in Joshua Tree 17:29 - Why product/market mattered more than location 19:33 - Selling a built home for $1.85M and reinvesting 21:21 - Discovering the short-term rental tax loophole strategy 22:41 - How the investor fund and 16% return structure works 23:27 - Walking through the $200K investment and depreciation example 26:16 - Addressing risk: market depreciation and recapture 27:29 - Material participation and the 100-hour qualification rule 28:45 - Why most CPAs get this wrong 30:08 - Counting hours: travel, contractors, and documentation 32:13 - Setting up the Airbnb account and listing automations 33:01 - Timing risk: closing late in the year and red flags 34:21 - Recommended six-month management period to avoid audit risk 35:43 - Clarifying depreciation carryover against W2 income year to year 37:00 - Doing this every year and staying audit-proof 38:20 - Current pipeline: 8 investors queued through 2027 40:11 - Passive loss rules and real estate professional status mix-up 41:28 - Future plans: scaling boutique hotel development 42:08 - Treehouse compound concept and land requirements 43:24 - Asheville market lessons and labor challenges 44:43 - Best current development markets: Texas, Arizona, SoCal 45:21 - Closing thoughts: freedom, documentation, and finding Rafa Join the free Revive real estate community: https://www.facebook.com/share/g/1H1y1et7wC/ Subscribe for weekly episodes on building real estate wealth around a demanding career. #RigsToRiches #ShortTermRental #AirbnbArbitrage #CostSegregation #BonusDepreciation #CaseyGregersen #RealEstateInvesting #STRTaxLoophole #PrivateMoney #RealEstateDevelopment

  8. 4d ago

    EP28: Bob McIntosh — Lost $40K on His First Flip, Now Funds Small DSCR Loans

    Bob McIntosh bought his first duplex in 2008, lost $40,000 on his first flip in 2009 with his parents' money, and kept going anyway. He has since flipped more houses than he can count, built a 31-door rental portfolio, spent 4,500+ hours teaching on stage, and now runs a marketing agency and a debt fund with his partners. In this episode Bob and Casey get into what the 2008-2009 crash taught him, why upside-down houses that still cash flowed were the missed opportunity of that decade, and why real estate held for 5 to 7 years tends to work itself out. Bob explains how his fund makes DSCR loans on properties under $100K-$150K that most lenders won't touch, how selling notes lets smaller investors take first position, and why a $10-20K roof on a $60K house changes the underwriting. They also cover using AI as the mentor he never had, why AI should add to a team rather than replace it, and how variable-rate debt sank multifamily syndicators. Bob McIntosh is a real estate investor, lender, and co-founder of 3 Degrees Consulting, a marketing agency. He is also a partner in a debt fund focused on small-balance DSCR loans. Book a call with Bob: https://go3dc.com/bobmcintosh CHAPTERS 00:00 - Cold open: what today's knowledge would have been worth back then 00:47 - Rigs to Riches intro 01:32 - Meet Bob McIntosh 02:17 - First duplex in Lockport, NY for $110K 03:02 - 4,500+ hours on stage, a marketing agency, and a fund 04:32 - Why he turned to flipping to raise capital fast 05:17 - First flip in 2009: a $40,000 loss 06:02 - Turning it around: flips and a 31-door portfolio 07:33 - Lessons from the 2008-2009 crash 09:04 - Upside-down houses that still cash flowed 10:35 - Banks selling 150 homes at 68 cents on the dollar 11:21 - Stay in the game: give real estate 5 to 7 years 12:07 - Starting today: AI as the mentor he never had 13:37 - Beating fear by playing out the worst case 15:08 - AI enhances people, it doesn't replace them 16:39 - Helping $10-30M companies adopt AI 18:10 - What Bob is focused on now 18:55 - The fund: DSCR loans on properties under $150K 19:41 - Why small-balance DSCR loans are hard to get 21:13 - Letting investors with under $100K take first position 21:58 - Selling notes at a spread: originate at 14%, sell at 12% 23:28 - How W2 earners should think about note investing 24:15 - Single-note risk vs a pooled fund 25:00 - Underwriting a note yourself: operator, market, economics 25:45 - Cheap houses, same repair costs: the $10-20K roof problem 28:04 - Building trust and transparency into loan products 28:49 - Where he sees opportunity: motivated sellers and creative finance 29:34 - Multifamily: finding deals without getting burned 30:20 - Why failed syndications all had variable-rate debt 31:05 - Buy, stabilize, then refinance with the bank 31:51 - Where to find Bob 32:36 - Closing thoughts Join the free Revive real estate community: https://www.facebook.com/share/g/1H1y1et7wC/ Subscribe for weekly episodes on building real estate wealth around a demanding career. #RigsToRiches #DSCRLoan #RealEstateInvesting #CaseyGregersen #NoteInvesting #PrivateMoneyLending #FixAndFlip #RentalProperties #CreativeFinance #RealEstateFinancing

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From oilfields to financial freedom. Rigs to Riches is all about helping hardworking W2 earners—especially in oil & gas—build true wealth through strategic real estate investing. Follow along for real deals, creative financing, and the unfiltered journey from the rig to real estate riches.

Information

  • Creator
    Casey Gregersen
  • Years Active
    2026
  • Episodes
    35
  • Rating
    Clean
  • Copyright
    © Casey Gregersen
  • Show Website
    Rigs to Riches