SlumDogg Millionaires

SlumDogg Millionaires

By Desiree Dogget and Kayla LambBusiness
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SlumDogg Millionaires episodes

  • Why People Beat Numbers in Real Estate | Matthew Teifke

    What if the fastest way to grow in real estate is to stop obsessing over the numbers?

    ๐ŸŽ™๏ธ Desiree Doggett and Kayla Lamb sit down with Matthew Teifke of TR3 to talk about relationships, partnerships, AI, and the lessons behind managing roughly $110 million in real estate including what Matthew learned after losing $4 million. Qc File Qc File

    For investors and landlords, this episode is about building long-term wealth without losing the human side of the business.

    ๐Ÿ‘ค Hosts & Guest

    Hosts: Desiree Doggett & Kayla Lamb

    Desiree is a Florida Realtorยฎ and property manager overseeing 350+ doors across the Suncoast. Kayla is a Sarasota-based sales agent and property manager with NextHome Excellence.

    Guest: Matthew Teifke

    Matthew Teifke is the founder of TR3 and says he has roughly $110 million under management. TR3 focuses on 100+ unit apartment communities in Austin and San Antonio.

    ๐Ÿ“Œ What Youโ€™ll Learn

    • Grow through relationships instead of numbers alone

    • Scale through trusted partnerships and mentorship

    • Use AI without replacing human connection

    • Improve property management through better communication

    • Think about real estate as a 30-50 year game

    • Separate self-worth from net worth

    • Create clearer boundaries between business and family

    Matthew repeatedly frames real estate as a people-driven business and a long-term process.

    โ“ Key Questions Answered

    Q: What does Matthew Teifke focus on in real estate?

    A: TR3 focuses on 100+ unit apartment communities in Austin and San Antonio.

    Q: What helped Matthew Teifke scale his real estate business?

    A: Relationships, adding value, and staying connected with people.

    Q: How did losing $4 million change his view of success?

    A: It taught him that personal worth should not be tied to net worth.

    Q: How does Matthew Teifke use AI in real estate?

    A: He uses AI to support outreach while keeping human relationships at the center.

    Q: How does Matthew Teifke balance business and family?

    A: He uses tighter communication and a 24-hour Sabbath to create boundaries.

    โฑ๏ธ Chapters

    (00:00) - Intro

    (00:14) - Meet Matthew Teifke

    (03:14) - Scaling Through Partnerships

    (05:12) - AI vs. Human Connection

    (07:26) - Matthewโ€™s Real Estate Journey

    (09:17) - The Reality of Long-Term Wealth

    (10:39) - Teaching Kids Work Ethic

    (12:59) - Losing $4 Million

    (14:59) - Real Estate Is About People

    (16:51) - Balancing Family & Business

    (19:03) - Faith, Purpose & Retirement

    (20:08) - The Key2Free & Giving Back

    (22:00) - Rebuilding After the $4M Loss

    (23:09) - Property Management & Recovery

    (24:14) - Freedom Over Money

    (26:00) - Closing Thoughtsย 

    ๐Ÿ‘‰ CONNECT WITH MATTHEW TEIFKE

    ๐ŸŒ Website โ†’ https://join.mattheweteifke.com

    ๐Ÿ“˜ Facebook โ†’ https://facebook.com/matthew.teifke

    ๐Ÿ”— LinkedIn โ†’ https://linkedin.com/in/matthew-teifke-90672438

    ๐Ÿ“ธ Instagram โ†’https://instagram.com/matthewteifke

    ๐Ÿ‘‰ FOLLOW SLUMDOGG MILLIONAIRES

    ๐ŸŒ Website โ†’ https://desireedoggett.sarasotahousehunt.com

    ๐Ÿ“˜ Facebook โ†’ https://facebook.com/people/SlumDogg-Millionaires

    ๐Ÿ“ธ Instagram โ†’ https://instagram.com/deztin8cion

    ๐Ÿ”— LinkedIn โ†’ https://linkedin.com/in/desiree-doggett-46776814

    ๐Ÿ“˜ Facebook โ†’ https://facebook.com/kaylaLovestoSell

    ๐Ÿ“ธ Instagram โ†’ https://instagram.com/kaylalamb1217

    ๐Ÿ”– Donโ€™t Forget to LIKE ๐Ÿ‘, SUBSCRIBE ๐Ÿ”” & COMMENT ๐Ÿ’ฌ Below!

    Would you rather grow a property management company organically or acquire an existing book of business? Why?

    Produced by Icons of Real Estate: https://iconsofrealestate.com/

    #SlumdoggMillionaires #DesireeDoggett #SarasotaRealEstate #SuncoastRealEstate #FloridaInvesting #PropertyManagement #RealEstateInvesting #LongTermWealth #RealEstatePodcast #NextHome

    27 min
  • Panama Investing: Financing, Rentals & Residency | Steve Luther

    Could buying property abroad give investors more options than staying only in the U.S.?

    On Slumdogg Millionaires, Desiree Doggett and Kayla Lamb sit down with Steve Luther of Chord Real Estate and Chord International to discuss Panama real estate, financing, residency options, rentals, safety, and buying property abroad.

    Steve also shares how his own international investing journey led him to Panama and eventually to helping other Americans explore overseas real estate.

    ๐Ÿ‘ค Host / Guest

    Hosts: Desiree Doggett & Kayla Lamb

    Co-hosts of Slumdogg Millionaires, sharing practical real estate investing and property management strategies.

    Guest: Steve Luther

    Steve Luther has worked in real estate for about 24 years after previously working in IT. He founded Chord Real Estate and later built Chord International after researching and purchasing property abroad.

    ๐Ÿ’ก What Youโ€™ll Learn

    • How to evaluate Panama real estate before buying

    • Ways Americans can finance property abroad

    • How to vet agents, developers, and property managers

    • Which Panama areas fit investing or retirement

    • How short-term rentals can create income

    • Why visiting the market firsthand matters

    โ“ Key Questions Answered

    Q: Can you buy real estate in Panama for under $200,000?

    A: Yes. Steve says some properties are available below $200,000, depending on location and property type.

    Q: Can Americans finance property in Panama?

    A: Yes. Options include cash, a HELOC, or Panama-based financing.

    Q: Can buying Panama real estate help with residency?

    A: Panama offers residency pathways connected to qualifying real estate investments.

    Q: Is Panama safe for American investors and retirees?

    A: Steve says he has felt very safe there and recommends visiting firsthand.

    Q: What should you check before buying property overseas?

    A: Vet the market, agents, attorneys, developers, and property managers before buying.

    โฑ๏ธ Chapters

    (00:00) - Hook

    (00:35) - Meet Steve Luther

    (01:59) - Steveโ€™s COVID Survival Story

    (06:16) - Why Steve Chose Panama

    (08:52) - How Buying Property Abroad Works

    (10:46) - Panama Residency & Investor Visas

    (13:11) - Panama Property Prices

    (15:00) - Financing Panama Real Estate

    (17:33) - Where to Invest in Panama

    (21:14) - Investing Beyond Panama

    (23:45) - Safety When Investing Abroad

    (26:22) - Retirement & Global Property Plan

    (28:29) - Red Cross & Steveโ€™s Charity Askย 

    ๐Ÿ‘‰ CONNECT WITH STEVE LUTHER

    ๐ŸŒ Website โ†’ https://chordrealestate.com/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/scluther

    ๐Ÿ”— LinkedIn โ†’ https://www.linkedin.com/in/scluther/

    ๐Ÿ“ธ Instagram โ†’https://www.instagram.com/scluther

    ๐Ÿ‘‰ FOLLOW SLUMDOGG MILLIONAIRES

    ๐ŸŒ Website โ†’ https://desireedoggett.sarasotahousehunt.com/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/people/SlumDogg-Millionaires/61576754805249/

    ๐Ÿ“ธ Instagram โ†’ https://www.instagram.com/deztin8cion

    ๐Ÿ”— LinkedIn โ†’ https://www.linkedin.com/in/desiree-doggett-46776814/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/kaylaLovestoSell/

    ๐Ÿ“ธ Instagram โ†’ https://www.instagram.com/kaylalamb1217/

    ๐Ÿ”– Donโ€™t Forget to LIKE ๐Ÿ‘, SUBSCRIBE ๐Ÿ”” & COMMENT ๐Ÿ’ฌ Below!

    Would you rather grow a property management company organically or acquire an existing book of business? Why?

    Produced by Icons of Real Estate: https://iconsofrealestate.com/

    #SlumdoggMillionaires #DesireeDoggett #SarasotaRealEstate #SuncoastRealEstate #FloridaInvesting #PropertyManagement #RealEstateInvesting #LongTermWealth #RealEstatePodcast #NextHome

    33 min
  • The Hidden Risk of Buying a Property Management Portfolio | Marc Cunningham

    Can buying more doors actually make a property management company harder to grow?

    On Slumdogg Millionaires, Desiree Doggett and Kayla Lamb sit down with Marc Cunningham of Grace Property Management to discuss scaling a property management business, client attrition, acquisitions, organic growth, and exit planning.

    Marc shares lessons from growing a family business to roughly 1,500 residential doors and explains why sustainable growth is about more than simply adding more clients.

    ๐ŸŽค Host & Guest

    Hosts: Desiree Doggett & Kayla Lamb

    Desiree is a Florida Realtorยฎ and property manager overseeing 350+ doors across the Suncoast. Kayla is co-host of Slumdogg Millionaires.

    Guest: Marc Cunningham

    Marc Cunningham is with Grace Property Management, a family business founded in 1978 that grew to roughly 1,500 residential doors.

    ๐Ÿ”‘ What Youโ€™ll Learn

    • Account for client attrition before buying a property management portfolio.

    • Balance acquisitions with organic growth.

    • Structure acquisitions around retained revenue.

    • Put investor interests ahead of management revenue.

    • Plan for an eventual business exit.

    โ“ Key Questions Answere

    Q: How much attrition can happen after a property management acquisition?A: Marc says even a strong acquisition may lose roughly 20% of clients in the first year.

    Q: How can buyers reduce acquisition risk?A: Marc describes paying the seller 50% of actual monthly portfolio income for two years, tying the payout to retained revenue.

    Q: Why is organic growth still important?A: Acquisitions can accelerate growth, but a sustainable property management business still needs a reliable way to win new clients.

    Focus on sustainable growth, retained clients, and the right opportunitiesโ€”not just more doors.

    โฑ๏ธ Chapters

    (00:00) - Cold Open: Business Exit Strategy

    (00:28) - Meet Marc Cunningham

    (01:55) - Marcโ€™s Real Estate Journey

    (03:04) - Buying His First Rental

    (04:37) - Joining Grace Property Management

    (06:07) - Selling Grace Property Management

    (08:08) - Following the Opportunity

    (10:52) - When Investors Should Sell

    (12:02) - Putting Investors First

    (14:11) - Buying a PM Book of Business

    (15:57) - Buying Growth vs. Organic Growth

    (17:18) - Structuring PM Acquisitions

    (19:31) - Lump-Sum Buyout Option

    (21:02) - Planning a Business Exit

    (22:08) - Identity Beyond the Business

    (23:26) - Fear-Based Exit Decisions

    (24:28) - 1031 Exchange & Vacation Homes

    (26:27) - Florida vs. Colorado Rentals

    (28:11) - Charity & Closingย 

    ๐Ÿ‘‰ CONNECT WITH MARC CUNNINGHAM

    ๐ŸŒ Website โ†’ https://www.pmbuild.com/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/marc.cunningham.39/

    ๐Ÿ”— LinkedIn โ†’ https://www.linkedin.com/in/marc-cunningham-0110108/

    ๐Ÿ‘‰ FOLLOW SLUMDOGG MILLIONAIRES

    ๐ŸŒ Website โ†’ https://desireedoggett.sarasotahousehunt.com/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/people/SlumDogg-Millionaires/61576754805249/

    ๐Ÿ“ธ Instagram โ†’ https://www.instagram.com/deztin8cion

    ๐Ÿ”— LinkedIn โ†’ https://www.linkedin.com/in/desiree-doggett-46776814/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/kaylaLovestoSell/

    ๐Ÿ“ธ Instagram โ†’ https://www.instagram.com/kaylalamb1217/

    โญ Produced by Icons of Real Estate - https://iconsofrealestate.com/

    ๐Ÿ”– Donโ€™t Forget to LIKE ๐Ÿ‘, SUBSCRIBE ๐Ÿ”” & COMMENT ๐Ÿ’ฌ Below!

    What would change in your real estate business if you could step away for three months? Comment below!

    Produced by Icons of Real Estate: https://iconsofrealestate.com/

    #SlumdoggMillionaires #DesireeDoggett #SarasotaRealEstate #SuncoastRealEstate #FloridaInvesting #PropertyManagement #RealEstateInvesting #LongTermWealth #RealEstatePodcast #NextHome

    31 min
  • Why Property Management Growth Breaks | James Davis

    What happens when a property management company grows faster than its operations can handle?

    On Slumdogg Millionaires, Desiree Doggett and Kayla Lamb talk with James Davis of Awarded about the people, systems, KPIs, and operational challenges behind property management growth.

    James shares how he went from accidental landlord to C-suite leadership, government-contract RFP work, and consulting. He also explains why weak operations can become a bottleneck, where AI can save time, and why more sales do not fix broken systems.

    ๐Ÿ’ก What Youโ€™ll Learn

    • Why people are often the biggest PM challenge

    • How weak operations limit growth

    • Which KPIs property managers should track

    • Where AI can reduce repetitive work

    • How to handle difficult property takeovers

    • Why staffing issues should be addressed early

    ๐Ÿ”Ž Key Questions Answered

    Q: What is the biggest challenge in property management?A: James says it is often people not necessarily bad employees, but good people whose role or performance no longer aligns with the companyโ€™s vision.

    Q: How can AI help property managers?A: AI can handle simple, repetitive work and give teams more time for higher-value tasks.

    Q: Why canโ€™t strong sales fix weak operations?A: More leads create more pressure when the systems behind the business cannot support growth.

    Q: What KPIs should property management companies track?A: James highlights leasing, on-site, and regional performance, including showings, prospects, guest cards, and consistent review of key numbers.

    Q: What should a PM company fix before adding more doors?A: Identify operational blockers, align the team, track the right KPIs, and strengthen systems before adding more volume.

    ๐ŸŽ„ Thanks For Giving Trees

    This episode also highlights Thanks For Giving Trees, a cause close to the Slumdogg Millionaires community.

    What started as a way to help local families bring home a Christmas tree has grown into a larger holiday tradition centered on generosity, community, and support.

    ๐ŸŒ Website: https://thanksforgivingtrees.com/

    ๐Ÿ“˜ Facebook: https://www.facebook.com/ThanksForGivingTrees2021

    ๐Ÿ“ธ Instagram: @thanksforgivingtrees

    โฑ๏ธ Chapters

    (00:00) - Intro

    (00:36) - Meet James Davis

    (00:56) - Government Contracting

    (02:03) - Accidental Landlord

    (03:05) - Government RFPs

    (05:32) - Growing Pains

    (06:40) - Consulting Challenges(

    07:26) - The People Problem

    (08:38) - KPIs That Matter

    (09:24) - AI in Property Management

    (11:43) - Property Takeover Chaos

    (14:50) - Sales vs. Operations

    (19:05) - Advice for Managers

    (23:51) - Thanks For Giving Trees

    (26:14) - Closing

    ๐Ÿ‘‰ Connect with James Davis

    ๐ŸŒ Website: https://awardedrfp.com/

    ๐Ÿ“ธ Instagram: https://www.instagram.com/awardedrfp

    ๐Ÿ”— LinkedIn: https://www.linkedin.com/in/davisjamesmichael/

    ๐Ÿ“˜ Facebook: https://www.facebook.com/profile.php?id=61584529914145

    ๐Ÿ‘‰ Follow Slumdogg Millionaires

    ๐ŸŒ Website: https://desireedoggett.sarasotahousehunt.com/

    ๐Ÿ“˜ Facebook: https://www.facebook.com/people/SlumDogg-Millionaires/61576754805249/

    ๐Ÿ“ธ Instagram: https://www.instagram.com/deztin8cion

    ๐Ÿ”— LinkedIn: https://www.linkedin.com/in/desiree-doggett-46776814/

    โญ Produced by Icons of Real Estatehttps://iconsofrealestate.com/

    #SlumdoggMillionaires #PropertyManagement #RealEstateInvesting #JamesDavis #DesireeDoggett

    27 min
  • Real Estate Investing Is a Long Game | John Casmon

    Would one bad real estate deal make you quit or change how you invest?

    Florida Realtorยฎ Desiree Doggett manages 350+ doors across the Suncoast and brings 13+ years of local experience. On Slumdogg Millionaires, Desiree and co-host Kayla Lamb join John Casmon to discuss house hacking, a $25,000 contractor loss, and investing through setbacks.

    Learn how to strengthen your rental property strategy through clearer tenant boundaries, contractor checks, and lessons from difficult deals.

    ๐ŸŽ™๏ธ Hosts & Guest

    Hosts: Desiree Doggett and Kayla LambGuest: John Casmon

    John spent 15 years in advertising and marketing and began investing through house hacking. John later moved into larger multifamily deals and says he has completed over $150 million in real estate with other investors.

    ๐Ÿ’ก What Youโ€™ll Learn

    • Build landlord experience through John Casmonโ€™s house hacking approach: live in one unit and rent another.

    • Keep tenant requests manageable by setting communication boundaries when living on-site.

    • Prepare for larger multifamily deals through mentorship and relationships with experienced investors.

    • Strengthen payment checks with Johnโ€™s lesson on obtaining subcontractor lien waivers before releasing funds.

    • Improve contractor vetting by following up on background-check concerns, even with a referral.

    • Rebuild confidence after a setback by reviewing your process and adjusting the next decision.

    โ“ Key Questions Answered

    Q: Do I need 20% down to start house hacking?A: John Casmon says his own purchase required 3.5% down, leaving roughly $50,000 available for improvements. That was Johnโ€™s experience, not a financing requirement for every buyer.

    Q: What does financial independence mean to John Casmon?A: John defines financial independence through three Cs: circle, community, and causes. His goals include greater family involvement and more charitable work.

    ๐Ÿ”— Keep Learning

    Follow Slumdogg Millionaires for real-world lessons you can bring to your next rental deal.

    ๐ŸŽ™๏ธ Multifamily Insights Podcast

    ๐Ÿ“˜ 7 Questions Before Investing in Apartments

    ๐Ÿ’ง Support Surge for Water

    โฑ๏ธ Chapters

    (00:00) - Hook : The $25,000 Contractor Nightmare

    (00:35) - Introduction: Meet John Casmon

    (01:22) - Why John Casmon Built a Real Estate Plan B

    (02:31) - From House Hacking to Multifamily Investing

    (04:24) - House Hacking and Tenant Boundaries

    (07:47) - Launching a Restoration Business

    (09:25) - A $25,000 Contractor Problem in Cincinnati

    (13:38) - Investing Setbacks and an Employerโ€™s Bankruptcy

    (14:52) - Staying Invested After a Bad Deal

    (17:32) - Contractor Vetting and Lien Waivers

    (20:30) - Financial Independence and the Three Cs

    (21:45) - Supporting Surge for Water

    (25:15) - Multifamily Insights and Apartment Investing Resources

    (26:01) - Closing Thoughts and Outroย 

    ๐Ÿ‘‰ CONNECT WITH JOHN CASMON

    ๐ŸŒ Website โ†’https://casmoncapital.com/about/

    ๐Ÿ“˜ Facebook โ†’https://www.facebook.com/jcasmon21/

    ๐Ÿ“ธ Instagram โ†’https://www.instagram.com/jcasmon/

    ๐Ÿ”— LinkedIn โ†’https://www.linkedin.com/in/multifamily-apartments-john-casmon

    ๐Ÿ‘‰ FOLLOW SLUMDOGG MILLIONAIRES

    ๐ŸŒ Website โ†’ https://desireedoggett.sarasotahousehunt.com/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/people/SlumDogg-Millionaires/61576754805249/

    ๐Ÿ“ธ Instagram โ†’ https://www.instagram.com/deztin8cion

    ๐Ÿ”— LinkedIn โ†’ https://www.linkedin.com/in/desiree-doggett-46776814/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/kaylaLovestoSell/

    ๐Ÿ“ธ Instagram โ†’ https://www.instagram.com/kaylalamb1217/

    โญ Produced by Icons of Real Estate - https://iconsofrealestate.com/

    ๐Ÿ”– Donโ€™t Forget to LIKE ๐Ÿ‘, SUBSCRIBE ๐Ÿ”” & COMMENT ๐Ÿ’ฌ Below!

    What would change in your real estate business if you could step away for three months? Comment below!

    Like and subscribe for more Sarasota and Suncoast Florida real estate conversations.

    Produced by Icons of Real Estate: https://iconsofrealestate.com/

    #SlumdoggMillionaires #DesireeDoggett #SarasotaRealEstate #SuncoastRealEstate #FloridaInvesting #PropertyManagement #RealEstateInvesting #LongTermWealth #RealEstatePodcast #NextHome

    27 min
  • Building a Real Estate Business That Works Without You | Bill Douglas

    โ€ผ๏ธ Can your real estate business grow when you are forced to step away? Bill Douglas shares how an unexpected injury changed his approach to delegation, systems, and business growth.

    ๐Ÿก On the Slumdogg Millionaires podcast, Desiree Doggett and Kayla Lamb speak with Bill Douglas about AI, commercial real estate technology, building data, property management, and the importance of human connection with tenants.

    ๐Ÿ“ˆ After a skiing crash left Bill Douglas with 13 broken bones and kept him away from work for three months, his business grew 25% in one quarter. Learn how better systems and smarter decisions can help build long-term wealth.

    ๐ŸŽง HOSTED BY: Desiree Doggett and Kayla Lamb | Slumdogg Millionaires

    ๐Ÿ‘ค GUEST: Bill Douglas

    Bill Douglas shares practical insights into real estate technology, property management, business delegation, and work-life balance.

    ๐ŸŽ™ WHAT YOUโ€™LL LEARN:

    โœ”๏ธ Building systems that keep a business running without the owner

    โœ”๏ธ Using AI and building data to improve property decisions

    โœ”๏ธ Understanding which jobs still require human skills and judgment

    โœ”๏ธ Identifying inefficiencies in security, HVAC, parking, and access systems

    โœ”๏ธ Recognizing when long work hours indicate a system problem

    โœ”๏ธ Reducing fear around real estate investing through better information

    โ“ KEY QUESTIONS ANSWERED:

    Q: How can AI improve commercial real estate and property management?

    A: AI and building data can help operators analyze security, HVAC, parking, and access systems to identify inefficiencies and make better decisions.

    Q: What happened when Bill Douglas stepped away from his business?

    A: After his skiing accident, Bill Douglas was away from work for three months, while the business grew 25% in one quarter.

    Q: Which jobs are least likely to be replaced by AI?

    A: Bill Douglas explains that skilled trades, building engineers, and human-facing roles require hands-on knowledge, judgment, and human interaction.

    โฑ๏ธ CHAPTERS:

    (00:00) Intro

    (00:25) Entering Real Estate Tech

    (02:53) AI in Commercial Real Estate

    (07:16) Jobs AI Cannot Replace

    (09:03) Property Management Technology

    (10:36) Using Building Data

    (13:06) Technology for New Developments

    (14:55) Near-Death Experience and Life Change

    (17:15) Delegation and 25% Growth

    (20:20) Working Less, Helping Others

    (21:33) Helping Veterans Find Careers

    (27:04) Removing Fear from Investing

    ๐Ÿ‘‰๐Ÿป CONNECT WITH BILL DOUGLAS

    Website: https://www.opticwise.com/

    LinkedIn: https://www.linkedin.com/in/billdouglas/

    ๐Ÿ‘‰๐Ÿป FOLLOW SLUMDOGG MILLIONAIRES

    Website: https://desireedoggett.sarasotahousehunt.com/

    Facebook: https://www.facebook.com/people/SlumDogg-Millionaires/61576754805249/

    Instagram: https://www.instagram.com/deztin8cion

    LinkedIn: https://www.linkedin.com/in/desiree-doggett-46776814/

    Kaylaโ€™s Facebook: https://www.facebook.com/kaylaLovestoSell/

    Kaylaโ€™s Instagram: https://www.instagram.com/kaylalamb1217/

    Can your real estate business operate without you? Share your thoughts and follow Slumdogg Millionaires for more real estate investing and property management conversations.

    ๐Ÿ’Ž Produced by Icons of Real Estate: https://iconsofrealestate.com/

    #SlumdoggMillionaires #DesireeDoggett #KaylaLamb #BillDouglas #SarasotaRealEstate #SuncoastRealEstate #FloridaInvesting #PropertyManagement #RealEstateInvesting #LongTermWealth #RealEstatePodcast #NextHome

    29 min
  • AI Maintenance Automation & PropTech Growth with Shayna Guigliano

    ๐ŸŽ™ What you'll learn:

    • The early days of scaling Appfolio from $30M to $800M ARR.

    • Why moving from legacy systems to all-in-one software changes business scaling.

    • How Vindoru's custom AI acts as an employee rather than standard software.

    • Managing 24/7 maintenance triage and text-based troubleshooting with ResiRoo.

    • Balancing AI efficiency with human empathy during critical property emergencies.

    • The importance of supporting anti-human trafficking initiatives like AIM.

    ๐ŸŽง HOSTED BY: The Slumdogg Millionaires Teamย 

    ๐Ÿ‘ค GUEST: Shayna Guiglianoย 

    Shayna Guigliano is a PropTech Executive and Head of Sales at Vendoroo, an AI platform transforming property maintenance operations. With extensive experience scaling sales organizations in vertical SaaS, she previously served as a sales leader at AppFolio, driving significant revenue growth. She introduces AI automation to traditional property management, helping owners streamline workflows and eliminate maintenance bottlenecks.

    ๐Ÿ‘‰๐Ÿป CONNECT WITH SHAYNA GUIGLIANO

    • Website: https://vendoroo.ai/

    • Facebook: https://www.facebook.com/vendorooai/

    • LinkedIn: https://www.linkedin.com/in/shayna-guigliano-6363534/

    ๐Ÿ‘‰๐Ÿป CONNECT WITH SLUMDOG MILLIONAIRES

    • Website: https://desireedoggett.sarasotahousehunt.com/ย 

    • Instagram: https://www.instagram.com/slumdoggmillionaires/ย 

    • Facebook: https://www.facebook.com/people/SlumDogg-Millionaires/61576754805249/ย 

    • LinkedIn: https://www.linkedin.com/in/desiree-doggett-46776814/?isSelfProfile=false

    28 min
  • Mastering Real Estate and Personalities with Kevin Weishaar

    The Slumdogg Millionaires team sits down with multifamily real estate expert Kevin Weishaar to discuss his 20-year journey in the industry.

    Property management can often feel like glorified babysitting, bringing intense interpersonal conflicts and completely unexpected situations right to your door.

    In this episode, Kevin reveals how mastering behavioral strategies like the DISC assessment can completely transform how you deal with difficult tenants and build powerful teams. Listen in for actionable investment advice, tips on surviving market chaos, and some hilarious horror stories from the frontlines of real estate.

    ๐ŸŽง Listen to the full episode of Slumdogg Millionaires now.

    ๐ŸŽ™ What you'll learn:

    • How to apply behavioral science to property management.

    • Ways to de-escalate conflicts using the DISC personality assessment.

    • The importance of staying cool and collected in a thankless job.

    • Real-world real estate horror stories (including naked tenants and ferrets).

    • Why holding onto investments during market chaos pays off.

    • Why you should always manage your own portfolio to some degree.

    • How to give back effectively to local charities like Seattle Children's Hospital.

    ๐ŸŽง HOSTED BY: Desiree and Kayla's

    ๐Ÿ‘ค GUEST: Kevin Weishaar

    Kevin A. Weishaar is an executive operations leader, multifamily housing expert, and the founder of Weishaar Strategic Partners. Based in Bellevue, Washington, he specializes in optimizing the intersection of people, systems, and execution for companies navigating rapid growth. He is a Certified Behavioral Consultant who utilizes advanced behavioral analysis and DISC to build trust and high-performing leadership teams.

    โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-โ€”-

    ๐Ÿ‘‰๐Ÿป CONNECT WITH KEVIN Weishaar

    โ€ข Website: https://www.kevinaweishaar.com/

    โ€ข Instagram: https://www.instagram.com/Weishaarpartners/

    โ€ข Facebook: https://www.facebook.com/people/Weishaar-Strategic-Partners/61578022707967/

    โ€ข LinkedIn: https://www.linkedin.com/in/kevinweishaar/

    ๐Ÿ‘‰๐Ÿป CONNECT WITH Desiree and Kayla's โ€“ SLUMDOGG MILLIONAIRES

    โ€ขย  Apple: https://podcasts.apple.com/us/podcast/slumdogg-millionaires/id1802165393ย 

    โ€ข Spotify: https://open.spotify.com/show/0newS9rGO0ipRZrXqgel33ย 

    Donโ€™t forget to LIKE ๐Ÿ‘ SUBSCRIBE ๐Ÿ”” COMMENT ๐Ÿ’ฌ below!

    18 min
  • Mastering Mentorship and Commercial Real Estate

    What if true wealth is about building assets so you can fund your passions indefinitely?

    When building a long-term commercial real estate portfolio, success requires more than just capital; it demands the right mix of logic, emotion, and solid relationships. Ray Hightower unpacks his journey from running a tech company to managing over $41 million in commercial real estate assets, revealing how strategic teamwork accelerates growth. Beyond the numbers, this conversation delves into the human element of business. Discover why paying an intern who offered to work for free led to profound professional lessons, and learn how aiming with logic while firing with emotion can help you punch through any wall. Finally, the episode challenges the traditional concept of retirement. Instead of stepping away completely, learn how accumulating cash-flowing assets can fund community service, faith-based initiatives, and youth development for years to come.

    ๐ŸŽง Hosted by: Desiree Dogget, Kayla Lamb

    ๐ŸŽค Featuring: Ray Hightower

    Ray Hightower is a Commercial Real Estate Syndicator and the Managing Partner of ROIClear, specializing in value-add multifamily and commercial properties in Arizona. A former technology company founder, he leverages his tech background to offer data-driven real estate syndications focused on capital preservation and consistent investor returns.

    ๐Ÿ’ก What Youโ€™ll Learn in This Episode:

    โœ” Transitioning successfully from the technology industry into commercial real estate.

    โœ” Building a reliable pipeline for talent through community organizations.

    โœ” Fostering win-win negotiations that create long-term business momentum.

    โœ” Balancing logical decision-making with the emotional fuel needed to punch through obstacles.

    โœ” Structuring passive income to redefine traditional retirement.

    โœ” Creating a powerful ripple effect through active mentorship.

    Charity Mention

    Ray Hightower mentioned supporting Boy Scouts of America in this episode. You can learn more about them via https://www.scouting.org/

    Connect with Ray Hightower:

    ๐ŸŒ Website โ†’ https://roiclear.com/

    ๐ŸŒ Website โ†’ https://rayhightower.com/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/RayHightower

    ๐Ÿ“ธ Instagram โ†’ https://www.instagram.com/RayHightower

    ๐ŸŽง Follow Desiree Dogget and Kayla Lamb:

    ๐ŸŒ Website โ†’ https://desireedoggett.sarasotahousehunt.com/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/people/SlumDogg-Millionaires/61576754805249/

    ๐Ÿ“ธ Instagram โ†’ https://www.instagram.com/deztin8cion

    ๐Ÿ”— LinkedIn โ†’ https://www.linkedin.com/in/desiree-doggett-46776814/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/kaylaLovestoSell/

    ๐Ÿ“ธ Instagram โ†’ https://www.instagram.com/kaylalamb1217/

    โญ Produced by Icons of Real Estate - https://iconsofrealestate.com/

    ๐Ÿ”– Donโ€™t Forget to LIKE ๐Ÿ‘, SUBSCRIBE ๐Ÿ”” & COMMENT ๐Ÿ’ฌ Below!

    #CommercialRealEstate #Mentorship #PassiveIncome #BusinessGrowth #WealthBuilding #SlumDoggMillionaires #ROI #RealEstateInvesting #Leadership #AssetManagement #DesireeDogget #KaylaLamb #RayHightower

    32 min
  • Breaking the Accredited Investor Barrier with Mor Milo

    What if you could invest in a 400-unit multifamily deal for just $100?

    Real estate syndication has traditionally been reserved for accredited investors, but Mor Milo is working to change that with Rally. In this episode, he breaks down the complexities of SEC regulations, explains the future of digital real estate crowdfunding, and shares why the industry is ripe for disruption.

    ๐ŸŽง Hosted by: Desiree Doggett

    ๐ŸŽค Featuring: Mor Milo

    Mor Milo is the CEO and founder of Rally, a digital marketplace connecting real estate sponsors with everyday investors. With a decade of entrepreneurial experience, Mor is on a mission to democratize real estate investing and eliminate the barriers of traditional syndication.

    ๐Ÿ’ก What Youโ€™ll Learn in This Episode:

    โœ” Accessing high-quality private real estate markets with minimal initial capital

    โœ” Navigating the complexities of Regulation D and Regulation A offerings

    โœ” Transitioning from traditional real estate syndication to digital crowdfunding platforms

    โœ” Identifying the limits of accredited investor pools to expand your capital raise

    โœ” Preparing legacy real estate businesses for blockchain and tokenization integration

    โœ” Exploring round-up micro-investments to seamlessly build a real estate portfolio

    Charities

    Mor Milo mentioned supporting Fish for Life in this episode. You can learn more about them via https://www.fishforlife.org/

    Connect with Mor:

    ๐Ÿ’ผ LinkedIn โ†’ https://www.linkedin.com/in/mormilo/

    ๐Ÿ“ธ Instagram โ†’ https://www.instagram.com/mor_milo/

    ๐ŸŽง Follow Desiree:

    ๐ŸŒ Website โ†’ https://desireedoggett.sarasotahousehunt.com/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/people/SlumDogg-Millionaires/61576754805249/

    ๐Ÿ“ธ Instagram โ†’ https://www.instagram.com/deztin8cion

    ๐Ÿ’ผ LinkedIn โ†’ https://www.linkedin.com/in/desiree-doggett-46776814/

    ๐Ÿ“˜ Facebook โ†’ https://www.facebook.com/kaylaLovestoSell/

    ๐Ÿ“ธ Instagram โ†’ https://www.instagram.com/kaylalamb1217/

    โญ Produced by Icons of Real Estate - https://iconsofrealestate.com/

    ๐Ÿ”– Donโ€™t Forget to LIKE ๐Ÿ‘, SUBSCRIBE ๐Ÿ”” & COMMENT ๐Ÿ’ฌ Below!

    #RealEstateInvesting #PropTech #Crowdfunding #PassiveIncome #Syndication #SECRegulations #AccreditedInvestor #WealthBuilding #DesireeDoggett #MorMilo


    32 min

About SlumDogg Millionaires

From the publisher's feed

Slumdogg Millionaires is your go-to podcast for all things real estate, property management, and financial freedom! Hosted by Desiree Doggett and Kayla Lamb, each episode is packed with insider tips,โ€ฆ