Rigs to Riches

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

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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

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.

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#RigsToRiches #TaxStrategy #TaxMitigation #BonusDepreciation #W2Income #HighIncomeEarners #CaseyGregersen #RealEstateInvesting #KyleMoore #StrategicAssociates

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

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#RigsToRiches #SelfDirectedIRA #RothIRA #RetirementInvesting #PrivateLending #Solo401k #CaseyGregersen #RealEstateInvesting #MatSorensen #DirectedIRA

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

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#RigsToRiches #JerryNorton #RealEstateInvesting #CaseyGregersen #Wholesaling #FixAndFlip #Entrepreneurship #FamilyFirst #LifestyleBusiness #FinancialFreedom

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

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#RigsToRiches #AirbnbDesign #ShortTermRental #InteriorDesign #CostSegregation #CaseyGregersen #RealEstateInvesting #BonusDepreciation #AirbnbHost #STRInvesting

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

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#RigsToRiches #OilAndGasInvesting #MineralRights #CaseyGregersen #RealEstateInvesting #Wholesaling #CapitalRaising #AIDataCenters #NaturalGas #PassiveIncome

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

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#RigsToRiches #ShortTermRental #AirbnbArbitrage #CostSegregation #BonusDepreciation #CaseyGregersen #RealEstateInvesting #STRTaxLoophole #PrivateMoney #RealEstateDevelopment

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

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#RigsToRiches #DSCRLoan #RealEstateInvesting #CaseyGregersen #NoteInvesting #PrivateMoneyLending #FixAndFlip #RentalProperties #CreativeFinance #RealEstateFinancing

If you know how to play the financing game, the banks work with you instead of against you. Justin Barber went from 12 years as a cardiac and ER nurse — then a hospital system director — to private money lending and now brokering DSCR and fix-and-flip debt for investors nationwide. In this episode he opens the underwriting black box: what DSCR lenders actually check, why they never care about your tax returns, the leverage available right now (up to 90% purchase + 100% of rehab), how the BRRRR math works with a 6-12 month seasoning window, and the paperwork mistakes that quietly kill loans.

Casey and Justin also get into 5-year fixed vs 30-year fixed on small multifamily, why cash flow isn't the only reason to buy, and how AI can pre-check your entity docs before an underwriter does.

Justin Barber is a former ICU/ER nurse turned real estate investor and lender. He runs private lending and DSCR brokerage at Rising Tide Lending, working with Casey's turnkey buyers and investors on DSCR and bridge terms. Get a quote: https://risingtidelending.com

CHAPTERS

00:00 - Cold open: you could be jobless and still get a DSCR loan

00:35 - Rigs to Riches intro

01:24 - Meet Justin Barber: nurse, investor, underwriter

02:26 - 12 years in nursing to hospital system director

03:35 - Why he wanted out and into real estate

04:24 - Studying wealthy people: the two common denominators

04:48 - Starting in private money lending

05:25 - The 3 realms of lending: private, institutional, DSCR/hard money

07:13 - Warehouse lines explained: whose money is it really?

08:25 - Why clear underwriting principles matter to the bank behind the bank

10:45 - Broker vs direct lender: shopping many lenders at once

12:46 - What a DSCR loan is and when to use it

13:23 - Credit pulls, no tax returns, no DTI, liquidity requirements

14:16 - How the ratio is calculated (taxes, insurance, HOA)

14:36 - Above 1.0 vs below 1.0 and what lenders allow

15:54 - Credit score tiers and lender appetite

17:17 - Current leverage: up to 90% purchase, 100% of rehab

17:46 - Pricing: ~12% annualized and points

19:21 - No-money-down scenarios and who they fit

20:08 - Best play today: BRRRR and avoiding the big down payment

21:47 - Forced appreciation, not handouts

23:14 - Seasoning: appraised value vs purchase price, 6-12 months

25:05 - Refi math on a 70-cents-on-the-dollar deal

25:40 - 5-year fixed vs 30-year fixed and interest-only options

27:07 - Casey's take: is a 5-year fixed too risky?

30:14 - Why cheap-ish debt still beats sitting out

30:34 - Case study: $500K fourplex with equity on day one

31:28 - Tax benefits and the real risk investors ignore

32:37 - The application process start to finish

33:14 - Why the broker reviews your docs before underwriting

34:32 - Entity docs, operating agreements, and credit sponsors

35:35 - The hack that keeps underwriting from rejecting you

36:01 - Appraisal, credit, and document review

37:08 - What happens when a loan has to be unsubmitted

39:52 - Get your ducks in a row: what to prepare now

40:12 - Operating agreements even when your state doesn't require one

41:18 - Using AI to pre-check your loan documents

42:59 - The standard document request list

44:25 - LLC vs personal name for title and liability

45:21 - Where to get a DSCR quote

45:45 - Justin's closing thought: patience, faith, and showing up

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Alex Pardo told a room full of investors his best deal was the one where he lost $51,000. Here is why — and how self-storage finally gave him the freedom that 12 years of flipping never did.

Guest: Alex Pardo, host of Flip Empire and founder of Storage Wins. He spent over a decade wholesaling and flipping in South Florida before shifting entirely into self-storage. He is now a part owner of four facilities (soon five), all run remotely with no employees.

Rigs to Riches is the show for high-earning W-2 professionals — especially in oil, gas and energy — who want to turn a big paycheck into real assets, real cash flow and real tax efficiency. Host Casey Gregersen went from the oilfield to a multi-million-dollar real estate portfolio, and every week he sits down with operators, investors, lenders and tax strategists who have done it.

EPISODE CHAPTERS

00:00 "I lost $51,000 — best deal I ever did"

01:20 Welcome to Rigs to Riches

02:30 GE finance program and learning what he didn't want

04:00 Backpacking Europe with the books that changed everything

04:40 Kinko's, 400 letters, and a first pre-foreclosure deal

06:00 Build the asset while you're still climbing

06:40 Nov 2005 mailer → Jan 2006 closing

07:30 13 deals year one — and the transactional trap

09:00 Twelve years of flips and wholesaling to the breaking point

10:30 Why self-storage: minimal capex, a real business

12:00 Recession resistance: people store in booms and busts

13:30 Four facilities, no employees, all run remotely

15:00 The mistake: wrong market, high crime, bad demographics

16:30 Cap rates in plain English (bought 6.8, selling 5.6)

18:00 Forcing value: why every dollar of NOI multiplies

18:40 The three-prong management system

21:00 Financing: small community banks, 25–30% down

21:50 90% seller financing and an 85% SBA loan

22:30 Private money at 10–12% and double-digit cash-on-cash

24:00 The short-term debt story every investor should hear

25:30 Take the longest term you can get

27:00 Storage Wins: first facility in 3–9 months

28:30 "What is the cost of inaction?"

30:00 The wrong first question a coaching prospect can ask

31:30 The 2007 luxury flip and a $102K loss

33:00 How a mentor saved him $51K

34:30 Masterminds vs one-on-one coaching

36:00 Family: 13 years married, girl dad, faith first

37:30 Letting what matters outside money drive decisions

39:00 "Holy moments" beat lavish trips

40:00 Take action

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