Real Talk with REsimpli Podcast

In this episode of Real Talk with REsimpli, Chenay Jordan and Don Carlson sit down with Chip Ferguson, owner of Smooth Closing, to unpack how nearly a decade as a high-volume online poker player shaped the way he thinks about probability, emotional control, risk, data, and decision-making in real estate.
Chip shares how he went from doing virtually everything himself to building an 11-person operation that has closed around 250 deals since the beginning of 2023.
In this episode, we get into:
- How poker taught Chip to stay calm when outcomes don’t go his way- The mistakes he made on his first real estate investment- Why he waited nine years before making his first hire- How hitting the same 36-deal ceiling two years in a row forced him to change- Why your first hire should depend on what you’re actually bad at- Building trust and negotiating with motivated sellers- When Chip chooses to wholesale vs. wholetail a property- How his team tackles complicated title and ownership problems other investors may walk away from- Why he relies heavily on data instead of trying to predict the housing market- The new-build deal that taught him a painful lesson about market predictions- Why doing what you’re best at can be a bigger advantage than chasing every real estate strategy- The mindset behind Chip’s 8+ year streak of working out every single day
REsimpli is an intuitive, all-in-one real estate software built for real estate investors that require little to no customization, so you can have your CRM up and running in minutes. REsimpli empowers your business with real-time data, allowing you to close on more deals while worrying less. Benefit from Calling, Texting, List Stacking, Driving 4 Dollars, and more all built within REsimpli.
Get 50% off your first month. Sign up here - https://bit.ly/4ef8ddJ
Join our free Mastermind for Real Estate Wholesalers: https://www.facebook.com/groups/wholesalersmastermind/
Try out REsimpli free for the first 14 days and see if you like it! https://resimpli.com/action-yt/
Connect with like-minded investors and wholesalers across the US through our Facebook group and weekly calls for FREE:https://resimpli.com/join-mastermind/
Connect with REsimpli-fb- https://www.facebook.com/REsimpli/
ig- https://www.instagram.com/resimpli
in- https://www.linkedin.com/company/resimpli
tt- https://www.tiktok.com/@resimpli_official
yt- https://www.youtube.com/@REsimpli
Connect with Chip:
Instagram: https://www.instagram.com/thechipferguson/
Facebook: https://www.facebook.com/TheChipFerguson

In this episode of Real Talk with REsimpli, Chenay Jordan and Don Carlson sit down with Oklahoma real estate investor and developer Jay London to unpack nearly 30 years of lessons from flipping houses, home building, bankruptcy, rebuilding, and eventually transitioning into commercial development.
Jay shares the moment a single house flip changed the direction of his life, what going broke taught him about risk, and why one of his biggest regrets was selling nearly everything he built instead of keeping more income-producing assets.
We also dive into:
• Why diversification matters in every real estate cycle• The danger of chasing “shiny objects” and social media success• Why Jay believes investors should build wealth—not just chase big checks• How residential investors can begin moving into commercial real estate• Ground-up development, warehouses, multifamily, and small-bay flex space• How commercial properties are valued differently from residential real estate• The biggest risks of becoming overleveraged• Why mentorship can save investors from expensive mistakes• How to approach zoning, permitting, architects, engineers, attorneys, and development teams• Why you shouldn’t close on land before confirming what you can actually build• Why land development can be one of the slowest—but most lucrative—real estate strategies
REsimpli is an intuitive, all-in-one real estate software built for real estate investors that require little to no customization, so you can have your CRM up and running in minutes. REsimpli empowers your business with real-time data, allowing you to close on more deals while worrying less. Benefit from Calling, Texting, List Stacking, Driving 4 Dollars, and more all built within REsimpli.
Get 50% off your first month. Sign up here - https://bit.ly/4ef8ddJ
Join our free Mastermind for Real Estate Wholesalers: https://www.facebook.com/groups/wholesalersmastermind/
Try out REsimpli free for the first 14 days and see if you like it! https://resimpli.com/action-yt/
Connect with like-minded investors and wholesalers across the US through our Facebook group and weekly calls for FREE:https://resimpli.com/join-mastermind/
Connect with REsimpli-fb- https://www.facebook.com/REsimpli/
ig- https://www.instagram.com/resimpli
in- https://www.linkedin.com/company/resimpli
tt- https://www.tiktok.com/@resimpli_official
yt- https://www.youtube.com/@REsimpli
Connect with Jay:
Email: jaylondonhomes@gmail.com
Facebook: https://www.facebook.com/jaylondonoklahoma
LinkedIn: https://www.linkedin.com/in/jaylondonhomes/
Phone Number: 405.443.8608
#RealEstateInvesting #CommercialRealEstate #RealEstateDevelopment #HouseFlipping #RealEstateInvestor #LandDevelopment #REsimpli 

In this episode of Real Talk with REsimpli, Don Carlson and Chenay Jordan sit down with Jacob Matlock, founder of Pillar Home Buyers, to discuss how he went from working as a refinery inspector to becoming a full-time real estate investor.
Jacob shares how extreme action, the right community and consistent execution helped him grow from complete beginner to 61 deals last year, with the business now tracking toward 80.
In this conversation, you’ll learn:
• Why Jacob left his six-figure job after only one year in real estate• How he grew by solving constraints in the right order: leads, processes and people• Why he is expanding beyond wholesaling into flips and rentals• The hiring mistakes that changed how he evaluates and manages employees• How his team approaches speed to lead, qualification and intentional follow-up• Why appointment set-to-attended rate is one of the most overlooked sales KPIs• How he uses AI to transcribe, score and analyze sales calls• Why genuine conversations and helping homeowners matter more than sales tactics
REsimpli is an intuitive, all-in-one real estate software built for real estate investors that require little to no customization, so you can have your CRM up and running in minutes. REsimpli empowers your business with real-time data, allowing you to close on more deals while worrying less. Benefit from Calling, Texting, List Stacking, Driving 4 Dollars, and more all built within REsimpli.
Get 50% off your first month. Sign up here - https://bit.ly/4ef8ddJ
Join our free Mastermind for Real Estate Wholesalers: https://www.facebook.com/groups/wholesalersmastermind/
Try out REsimpli free for the first 14 days and see if you like it! https://resimpli.com/action-yt/
Connect with like-minded investors and wholesalers across the US through our Facebook group and weekly calls for FREE:https://resimpli.com/join-mastermind/
Connect with REsimpli-fb- https://www.facebook.com/REsimpli/
ig- https://www.instagram.com/resimpli
in- https://www.linkedin.com/company/resimpli
tt- https://www.tiktok.com/@resimpli_official
yt- https://www.youtube.com/@REsimpli
Connect with Jacob:
- Email: jacobm@pillarhomebuyers.com
- Website: https://www.pillarhomebuyers.com/
- Instagram: https://www.instagram.com/jacobisamatlock/

In this episode of Real Talk with REsimpli, Don Carlson and Chenay Jordan sit down with Esteban Andrade, co-founder of Remote Latinos and founder of Hesel Media, to discuss real estate marketing, remote hiring, AI, leadership, and what it takes to build a business that can scale.
Esteban shares his journey from moving from Colombia to Canada as a teenager and learning English through video games to sleeping in his car, driving Uber, and eventually building successful companies that help entrepreneurs generate leads and hire high-performing remote professionals.
The conversation explores how real estate investors should choose between Google and Facebook advertising, why generic “cash offer” messaging is becoming less effective, and how targeting a seller’s specific situation can help investors stand out in competitive markets.
Esteban also explains why business owners should stop treating every remote hire as a general virtual assistant. Instead, investors should hire specialists for roles such as lead management, appointment setting, acquisitions, executive assistance, and client success—and give those professionals the AI tools they need to produce better results.
You’ll learn:
• When real estate investors should use Google Ads versus Facebook Ads• Why seller awareness affects lead quality and conversion time• How to create marketing offers that stand out from other investors• Why specialized remote professionals outperform generalist VAs• How AI can amplify employees instead of simply replacing them• The most in-demand remote roles for real estate investing businesses• How scorecards, KPIs, and performance improvement plans strengthen teams• Which leadership hires can unlock the next stage of business growth
REsimpli is an intuitive, all-in-one real estate software built for real estate investors that require little to no customization, so you can have your CRM up and running in minutes. REsimpli empowers your business with real-time data, allowing you to close on more deals while worrying less. Benefit from Calling, Texting, List Stacking, Driving 4 Dollars, and more all built within REsimpli.
Get 50% off your first month. Sign up here - https://bit.ly/4ef8ddJ
Join our free Mastermind for Real Estate Wholesalers: https://www.facebook.com/groups/wholesalersmastermind/
Try out REsimpli free for the first 14 days and see if you like it! https://resimpli.com/action-yt/
Connect with like-minded investors and wholesalers across the US through our Facebook group and weekly calls for FREE:https://resimpli.com/join-mastermind/
Connect with REsimpli-fb- https://www.facebook.com/REsimpli/
ig- https://www.instagram.com/resimpli
in- https://www.linkedin.com/company/resimpli
tt- https://www.tiktok.com/@resimpli_official
yt- https://www.youtube.com/@REsimpli
Connect with Esteban:
- Twitter: https://www.linkedin.com/in/estenick
- Instagram: https://www.instagram.com/estenick/
 

In this episode of Real Talk with REsimpli, Don Carlson and Chenay Jordan sit down with Tom Krol, founder of Coaching Inc. and the entrepreneur behind Wholesaling Inc., to discuss real estate investing, coaching, relationships, wealth, and what it takes to build a successful business without sacrificing the rest of your life.
Tom shares how he went from being broke and getting fired from seven jobs to completing 100 real estate deals in his first 18 months. He explains why having a mentor, eliminating distractions, and taking massive imperfect action helped him break through when others remained stuck in preparation mode.
The conversation also explores why relationships are often the biggest drivers of business growth, how to distinguish success from wealth, and why an entrepreneur’s ability to handle pressure can determine how far they go.
Tom also shares practical lessons for choosing the right coach, helping students overcome doubt and disappointment, building a coaching business around one clear offer, and creating a community where people feel recognized and supported.
You’ll learn:
- How Tom completed 100 real estate deals in 18 months- Why preparation can become a form of procrastination- The three biggest reasons real estate students fail- How mentors and relationships accelerate business growth- Why handling pressure is critical for entrepreneurs- What to look for when choosing a real estate coach- How coaches can build value, volume, and community- Why making money and keeping money require different skills- How in-person events can help grow a coaching business- The books Tom believes every entrepreneur should read
REsimpli is an intuitive, all-in-one real estate software built for real estate investors that require little to no customization, so you can have your CRM up and running in minutes. REsimpli empowers your business with real-time data, allowing you to close on more deals while worrying less. Benefit from Calling, Texting, List Stacking, Driving 4 Dollars, and more all built within REsimpli.
Get 50% off your first month. Sign up here - https://bit.ly/4ef8ddJ
Join our free Mastermind for Real Estate Wholesalers: https://www.facebook.com/groups/wholesalersmastermind/
Try out REsimpli free for the first 14 days and see if you like it! https://resimpli.com/action-yt/
Connect with like-minded investors and wholesalers across the US through our Facebook group and weekly calls for FREE:https://resimpli.com/join-mastermind/
Connect with REsimpli-fb- https://www.facebook.com/REsimpli/
ig- https://www.instagram.com/resimpli
in- https://www.linkedin.com/company/resimpli
tt- https://www.tiktok.com/@resimpli_official
yt- https://www.youtube.com/@REsimpli
Connect with Tom: 
Find a current member or real estate coach in the group and ask them for an introduction to Coachin Inc.

In this episode of Real Talk with REsimpli, Don Carlson and Chenay Jordan sit down with Jason Pritchard, founder and CEO of Pinnacle Home Buyers, to talk about building a real estate business that lasts.
After spending 15 years in corporate America, Jason left the security of a paycheck to pursue real estate full time. Since then, he has led the acquisition of more than 500 properties across California’s Central Valley through wholesaling, fix and flips, rentals, creative finance, and large-scale land development.
Jason shares what it really takes to move from owner-operator to business owner, why systems and leadership matter more than just doing more deals, and how investors can build teams, raise private capital, and stay consistent in a challenging market.
You’ll learn:
- How Jason went from corporate sales to real estate investing- Why his first deal took nearly a year to close- How he built a rental portfolio by reinvesting profits- Why your first hire should align with your strengths and weaknesses- What investors should know before scaling their team- Why direct mail still works in today’s market- How speed to lead impacts real estate acquisitions- The biggest mistakes investors make when raising private capital- Why building a business is different from simply buying houses
REsimpli is an intuitive, all-in-one real estate software built for real estate investors that require little to no customization, so you can have your CRM up and running in minutes. REsimpli empowers your business with real-time data, allowing you to close on more deals while worrying less. Benefit from Calling, Texting, List Stacking, Driving 4 Dollars, and more all built within REsimpli.
Get 50% off your first month. Sign up here - https://bit.ly/4ef8ddJ
Join our free Mastermind for Real Estate Wholesalers: https://www.facebook.com/groups/wholesalersmastermind/
Try out REsimpli free for the first 14 days and see if you like it! https://resimpli.com/action-yt/
Connect with like-minded investors and wholesalers across the US through our Facebook group and weekly calls for FREE:https://resimpli.com/join-mastermind/
Connect with REsimpli-fb- https://www.facebook.com/REsimpli/
ig- https://www.instagram.com/resimpli
in- https://www.linkedin.com/company/resimpli
tt- https://www.tiktok.com/@resimpli_official
yt- https://www.youtube.com/@REsimpli
Connect with Jason: 
Email: jason@pinnaclehomebuyers.com
Website: www.pinnaclehomebuyers.com
Instagram: https://www.instagram.com/jasonpritchard/

In this episode of Real Talk with REsimpli, hosts Chenay Jordan and Don Carlson sit down with Joe Evangelisti, high-performance coach, real estate investor, entrepreneur, Navy Seabee veteran, and founder of Legacy Builder.
Joe shares how his background in construction and the military shaped the way he solves problems, leads teams, and helps entrepreneurs build businesses that create freedom instead of stress. From flipping houses during the 2008 crash to owning a brokerage, building teams, coaching business owners, and investing in commercial real estate, Joe breaks down what it really takes to scale without becoming the bottleneck.
This conversation dives into leadership, systems, accountability, time freedom, legacy, and the five bottlenecks that stop entrepreneurs from growing.
You’ll learn:
- How Joe went from Navy Seabee to real estate investor and business coach- Why growth does not solve business problems, it exposes them- How to stop being the bottleneck in your business- The five bottlenecks that keep entrepreneurs stuck- Why consistency and accountability matter more than complicated tools- How to create more freedom while still growing your business- Why legacy is about impact, values, and leadership, not just money
REsimpli is an intuitive, all-in-one real estate software built for real estate investors that require little to no customization, so you can have your CRM up and running in minutes. REsimpli empowers your business with real-time data, allowing you to close on more deals while worrying less. Benefit from Calling, Texting, List Stacking, Driving 4 Dollars, and more all built within REsimpli.
Get 50% off your first month. Sign up here - https://bit.ly/4ef8ddJ
Join our free Mastermind for Real Estate Wholesalers: https://www.facebook.com/groups/wholesalersmastermind/
Try out REsimpli free for the first 14 days and see if you like it! https://resimpli.com/action-yt/
Connect with like-minded investors and wholesalers across the US through our Facebook group and weekly calls for FREE:https://resimpli.com/join-mastermind/
Connect with REsimpli-fb- https://www.facebook.com/REsimpli/
ig- https://www.instagram.com/resimpli
in- https://www.linkedin.com/company/resimpli
tt- https://www.tiktok.com/@resimpli_official
yt- https://www.youtube.com/@REsimpli
Connect with Joe:
Email: joseph.evangelisti@gmail.com
Website: https://legacybuilder.coach
LinkedIn: https://www.linkedin.com/in/jevangelisti

In this episode of Real Talk with REsimpli, Don Carlson and Chenay Jordan sit down with Bree Hartman, founder of Storage House Group and Self-Storage School, to talk about how real estate investors can break into self-storage without needing millions of dollars or a commercial real estate background.
Bree shares how an accidental rental property, a desire for more time freedom, and a focus on one overlooked asset class led her to acquire more than $8 million in self-storage assets. She breaks down why self-storage can be such a powerful business model, how investors can find off-market mom-and-pop facilities, and why creative finance and seller financing can open doors that traditional investing strategies often miss.
This conversation also dives into practical acquisition strategies investors can use right away, including how to use Google Maps to find unsophisticated storage owners, what to look for in a potential deal, how to start conversations with owners, and how AI is changing operations, customer service, and call handling in the storage industry.
You’ll learn:
- How Bree went from an accidental rental to self-storage investing- Why self-storage offers fewer headaches than traditional rentals- How to find off-market mom-and-pop storage facilities- What makes seller financing powerful in self-storage deals- How small operational improvements can increase facility value- Why reviews, websites, and Google Maps can reveal hidden opportunities- How AI is helping storage owners reduce expenses and improve operations- Why self-storage can help investors build both financial freedom and time freedom
REsimpli is an intuitive, all-in-one real estate software built for real estate investors that require little to no customization, so you can have your CRM up and running in minutes. REsimpli empowers your business with real-time data, allowing you to close on more deals while worrying less. Benefit from Calling, Texting, List Stacking, Driving 4 Dollars, and more all built within REsimpli.
Get 50% off your first month. Sign up here - https://bit.ly/4ef8ddJ
Join our free Mastermind for Real Estate Wholesalers: https://www.facebook.com/groups/wholesalersmastermind/
Try out REsimpli free for the first 14 days and see if you like it! https://resimpli.com/action-yt/
Connect with like-minded investors and wholesalers across the US through our Facebook group and weekly calls for FREE:https://resimpli.com/join-mastermind/
Connect with REsimpli-
fb- https://www.facebook.com/REsimpli/
ig- https://www.instagram.com/resimpli
in- https://www.linkedin.com/company/resimpli
tt- https://www.tiktok.com/@resimpli_official
yt- https://www.youtube.com/@REsimpli
Connect with Bree:
Email: bree@selfstorageschool.com
Website: https://www.selfstorageschool.com/

In this episode of Real Talk with REsimpli, Don Carlson and Chenay Jordan sit down with Quinn Edwards, co-founder of AI for CRE Collective, to talk about how artificial intelligence is changing the real estate industry.
Quinn shares his journey from working at CBRE on more than $500M in transactions to building a real estate development company, and ultimately pivoting into AI education for commercial real estate professionals. He breaks down the AI tools he actually uses, including Claude, ChatGPT, Manus, Perplexity, Prophetic, Algoma, and Pillar, and explains how real estate investors, brokers, wholesalers, flippers, and CRE professionals can use AI to save time, improve workflows, and make better decisions.
The conversation also covers the biggest mistakes real estate professionals make with AI, why prompting matters, how to use the RCTF framework, and why AI should be treated as a tool, not a magic pill.
Plus, Quinn shares stories from training Muay Thai in Thailand, preparing for Ironman races, and why entrepreneurs can learn a lot from endurance athletes.
In this episode, we cover:
- Quinn’s path from CBRE to AI for CRE - Why he pivoted from real estate development into AI-The best AI tools for real estate professionals- How to use Claude, ChatGPT, Manus, and Perplexity- The biggest AI mistakes investors are making- How to prompt AI more effectively- Why fundamentals still matter in real estate- Lessons from endurance training, Muay Thai, and entrepreneurship
REsimpli is an intuitive, all-in-one real estate software built for real estate investors that require little to no customization, so you can have your CRM up and running in minutes. REsimpli empowers your business with real-time data, allowing you to close on more deals while worrying less. Benefit from Calling, Texting, List Stacking, Driving 4 Dollars, and more all built within REsimpli.
Get 50% off your first month. Sign up here - https://bit.ly/4ef8ddJ
Join our free Mastermind for Real Estate Wholesalers: https://www.facebook.com/groups/wholesalersmastermind/
Try out REsimpli free for the first 14 days and see if you like it! https://resimpli.com/action-yt/
Connect with like-minded investors and wholesalers across the US through our Facebook group and weekly calls for FREE:https://resimpli.com/join-mastermind/
Connect with REsimpli-fb- https://www.facebook.com/REsimpli/
ig- https://www.instagram.com/resimpli
in- https://www.linkedin.com/company/resimpli
tt- https://www.tiktok.com/@resimpli_official
yt- https://www.youtube.com/@REsimpli
Connect with Quinn -
Instagram: https://www.instagram.com/aiforcre/
TikTok: https://www.tiktok.com/@aiforcrecollective 
Skool: https://www.skool.com/ai-for-cre-collective/about

In this episode of Real Talk with REsimpli, hosts Chenay Jordan and Don Carlson sit down with Jenn and Joe Del Fave, the husband-and-wife team behind Creative Finance Playbook.
Jenn and Joe share how they went from traditional jobs and early real estate struggles to building a multi-million-dollar portfolio using creative finance, seller financing, subject-to deals, and rent-to-own strategies — without relying on banks, massive down payments, or perfect credit.
They break down how they find motivated sellers, structure creative deals, turn good houses into profitable opportunities, and use rent-to-own buyers to generate upfront income, monthly cash flow, and backend profits. They also get real about working together as spouses, building systems, learning from mentorship, and staying disciplined through changing market cycles.
REsimpli is an intuitive, all-in-one real estate software built for real estate investors that require little to no customization, so you can have your CRM up and running in minutes. REsimpli empowers your business with real-time data, allowing you to close on more deals while worrying less. Benefit from Calling, Texting, List Stacking, Driving 4 Dollars, and more all built within REsimpli.
Get 50% off your first month. Sign up here - https://bit.ly/4ef8ddJ
Join our free Mastermind for Real Estate Wholesalers: https://www.facebook.com/groups/wholesalersmastermind/
Try out REsimpli free for the first 14 days and see if you like it! https://resimpli.com/action-yt/
Connect with like-minded investors and wholesalers across the US through our Facebook group and weekly calls for FREE:https://resimpli.com/join-mastermind/
Connect with REsimpli-fb- https://www.facebook.com/REsimpli/
ig- https://www.instagram.com/resimpli
in- https://www.linkedin.com/company/resimpli
tt- https://www.tiktok.com/@resimpli_official
yt- https://www.youtube.com/@REsimpli
Connect with Jenn and Joe:
Website: https://creativefinanceplaybook.com/