Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! In this episode, I’m joined by Caleb Christopher, founder of Creative TC, a consulting company built to make creative finance deals safe, legal, ethical, and clearly understood by everyone involved.

This is one of the most grounded and practical conversations I’ve had about creative finance. Caleb breaks down exactly when strategies like subject-to actually make sense, when they absolutely don’t, and why most investors misunderstand what these deals really are. We walk through real stories, real numbers, and real outcomes — not hype or shortcuts.

We also talk about why creative finance is fundamentally a long-term partnership, not a quick transaction, why most title companies struggle with these deals, and how proper documentation, disclosures, and expectation-setting protect both the investor and the seller. If you’ve ever been curious about creative finance but unsure where the ethical and legal lines are, this episode brings real clarity.

Episode Timeline

[0:00] – Introducing Caleb Christopher and why he built a business around creative finance.

[2:58] – What Creative TC does and why consulting is critical for complex deals.

[3:16] – Why most traditional title companies struggle with creative transactions.

[4:27] – Why Caleb chose creative finance over traditional investing models.

[5:10] – Why creative finance thrives on complexity and problem-solving.

[5:31] – Subject-to explained in plain English.

[6:13] – Why every real estate deal is technically “subject to” something.

[7:02] – How creative buy boxes differ from wholesaling and flipping.

[10:37] – Pre-foreclosure situations where creative finance truly helps.

[11:12] – Anchoring value: why catching up payments is real money.

[12:14] – How creative deals can actually improve seller credit.

[12:59] – A real subject-to case study with short-term negative cash flow and long-term upside.

[14:10] – Why win-win matters more than squeezing every dollar.

[15:56] – Why creative deals are partnerships, not transactions.

[21:21] – Managing seller expectations months or years after closing.

[22:02] – Why disclosures and documentation protect everyone.

[26:34] – Why title companies say “no” to what they don’t understand.

[27:20] – Caleb’s disciplined, accountable growth strategy.

[29:11] – Where AI fits into creative finance, consulting, and title work.

[33:01] – The future of AI agents, CRMs, and decision-based automation.

[36:42] – How to connect with Caleb and follow his transparent newsletter.

5 Key Takeaways

1. Creative finance only works after traditional options fail. Cash, MLS, and keeping the property must be ruled out first.
2. Story beats structure. Seller motivation and context matter more than formulas.
3. Creative deals are partnerships. Expect long-term communication and responsibility.
4. Documentation protects everyone. Ethical creative finance requires clarity and disclosures.
5. Technology should assist judgment, not replace it. AI enhances consulting, not accountability.

Links & Resources

• Creative TC – https://creativetc.io/about
• SmrtPhone – The only phone system built for real estate investors (5,000 free minutes)
• ThatRealEstateTechGuy.com – All episodes and exclusive tech discounts

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Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! In this episode, I’m joined by Benmont Locker, real estate operator, entrepreneur, and co-founder of RAMP REI, a consulting and training organization focused on helping investors build scalable, metrics-driven sales machines.

This conversation is less about shiny tools and more about the unsexy fundamentals that actually allow businesses to scale. Benmont shares how his team helped build and operate a 500+ deals-per-year real estate organization by systematizing intuition, enforcing accountability through data, and creating a culture where performance — not personalities — drives decisions.

Episode Timeline & Highlights

[0:00] – Introducing Benmont Locker and his background in operational startups and real estate.

[1:39] – Why this episode is really about entrepreneurship, not just technology.

[3:41] – Scaling to 50+ employees and hundreds of deals per year by systematizing fundamentals.

[5:07] – Why “anyone can start a business, but scaling one is the real skill.”

[6:27] – The leadership transformation required to move beyond intuition and brute force.

[7:46] – Turning one person’s experience and instincts into repeatable systems.

[9:06] – The role enterprise CRMs play in shortening feedback loops and enforcing truth.

[9:48] – Consolidating platforms to improve data integrity and decision-making.

[12:38] – Why metrics make hard leadership conversations objective, not personal.

[13:28] – How data enables autonomy, accountability, and better team leadership.

[15:22] – Why people hide in growing companies without visibility and metrics.

[16:09] – Avoiding data overload: only measure what you’re willing to act on.

[16:54] – The “six core metrics” rule and nested metric analysis.

[17:51] – Identifying whether problems are people, process, or strategy.

[18:58] – Board-level metrics vs. day-to-day operator metrics.

[23:08] – How metrics transformed company culture and peer accountability.

[25:19] – Real examples of accountability flowing upward — not just downward.

[27:24] – The transition from operating companies to building RAMP REI.

[28:45] – Operationalizing sales to create predictable conversion.

[33:07] – Integrity, receipts, and why real operators make the best mentors.

[35:20] – Why fundamentals never change, regardless of technology.

[38:29] – Discipline over motivation and why execution beats inspiration.

[41:52] – How technology compresses timelines — but doesn’t eliminate the work.

[42:33] – How to connect with Benmont and learn more about RAMP REI.

5 Key Takeaways

1. Scaling is operational, not inspirational. Systems beat intuition past a certain size.
2. Metrics remove emotion. Truth enables better leadership, accountability, and culture.
3. Only measure what you’ll act on. Data without decisions creates paralysis.
4. Culture is built on performance clarity, not perks or slogans.
5. Real businesses are built on fundamentals, not hacks or shortcuts.

Links & Resources:

• RAMP REI – https://ramprei.com/
• SmrtPhone – https://www.smrtphone.io/
• ThatRealEstateTechGuy.com – All episodes and exclusive tech discounts

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Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! In this episode, I’m joined by David Richter, author of Profit First for Real Estate Investing and founder of Simple CFO Solutions. This is one of those conversations that every investor needs to hear — especially if you’re scaling and wondering why more deals aren’t translating into more money in the bank.

David and I dig into the fundamentals that never go out of style: cash flow, profit, and financial clarity. We talk about why revenue is vanity, profit is sanity, and cash is king — and how too many investors scale volume without fixing the leaks underneath. We also explore where technology helps financial clarity and where it creates analysis paralysis that actually slows growth.

If you’re doing deals but still feeling stressed, underpaid, or unsure where the money is going, this episode will help you reset your foundation and build a business that actually pays you.

Episode Timeline & Highlights

[0:00] – Introduction

[0:42] – Introducing David Richter and why profit matters more than deal volume.

[2:04] – Scaling to 25 deals a month while losing money — and the wake-up call that followed.

[4:03] – Why every business eventually comes down to profit, cash flow, and fundamentals.

[7:48] – Why outsourcing bookkeeping doesn’t replace owner financial responsibility.

[8:53] – The first step: implementing a cash management system before hiring help.

[10:25] – What business owners must understand, even with a CFO or finance team.

[11:25] – The three numbers every investor needs to know: make, spend, keep.

[17:00] – How small overruns multiply into major cash crises at scale.

[18:06] – Tech that helps: Profit First banking, automation, and expense management.

[22:15] – QuickBooks Online, dashboards, and choosing tools that support decisions.

[25:38] – Dashboards done right vs. dashboards that cause paralysis.

[26:23] – Only track numbers that lead to decisions.

[33:11] – Investors obsess over CRMs but avoid the numbers that create freedom.

[34:23] – Doing 300 deals a year and being no closer to financial freedom.

[36:09] – Financial literacy is a skill — not a personality trait.

[38:00] – How Simple CFO Solutions helps investors at different stages.

[40:09] – How financial clarity reduced stress and improved decision-making at scale.

5 Key Takeaways

1. More deals don’t equal more profit. Without systems, scale just magnifies financial problems.
2. Business owners must understand their numbers. Delegation doesn’t remove responsibility.
3. Cash management comes before accounting. Profit First gives owners control immediately.
4. Track only decision-driving metrics. More data isn’t better — better data is.
5. Financial clarity reduces stress. Knowing where money goes changes how you lead and scale.

Links & Resources

• Profit First for Real Estate Investing – https://join.simplecfo.com/book-a-discovery-call
• Simple CFO Solutions – simplecfo.com
• SmrtPhone – The only phone system built for real estate investors (5,000 free minutes).
• ThatRealEstateTechGuy.com – All episodes and exclusive tech discounts.

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Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! In this episode, I’m joined by Sam Wegert, serial entrepreneur and co-living operator who’s building one of the most interesting alternative housing models I’ve seen in real estate today.

Sam and I dive deep into co-living — a strategy that’s been common in Europe for years but is now emerging in the U.S. as a powerful solution to the affordable housing crisis and a highly profitable exit strategy for investors. We unpack why co-living is gaining acceptance where Airbnb is being restricted, how it creates long-term stability instead of short-term volatility, and why this model may outperform traditional rentals over the next decade.

We also explore Sam’s turnkey approach, how wholesalers and flippers can pre-sell deals into co-living buy boxes, and what investors should be thinking about as markets tighten and traditional exits get harder. This conversation is a masterclass in adapting to market shifts with creativity, data, and long-term thinking.

Episode Timeline & Highlights

[0:00] – Introducing Sam Wegert and his entrepreneurial background.

[1:17] – What co-living is and why it’s common globally but still new in the U.S.

[4:15] – Why co-living can be one of the highest cash-flowing asset classes today.

[6:25] – The math behind affordability: why studio apartments don’t work for most workers.

[8:14] – Renting by the room: creating a brand-new price point in housing.

[9:26] – Who co-living serves: young professionals, remote workers, and older adults.

[11:36] – Loneliness, community, and why co-living solves more than just housing costs.

[17:36] – How consistent, long-term tenants outperform short-term rental volatility.

[19:01] – Turning co-living into a new exit strategy for wholesalers and flippers.

[22:08] – How Sam tests demand in new markets before buying property.

[23:41] – Location rules: commute distance, no HOAs, and neighborhood fit.

[33:06] – Technology stack: smart locks, cameras, management systems, and safety.

[35:14] – The co-living buy box: size, bathrooms, parking, and layout.

[42:18] – How to learn more and attend Sam’s free co-living challenge.

5 Key Takeaways

1. Co-living solves a real problem. It addresses affordability, isolation, and housing demand without government subsidies.
2. Needed beats wanted. Co-living provides stability that short-term rentals can’t match in uncertain markets.
3. Exit strategies are evolving. Wholesalers and flippers can pre-sell into co-living buy boxes for premium exits.
4. Design matters. Layout, parking, and neighborhood fit determine long-term success.
5. Systems win. Technology and management processes make co-living scalable and repeatable.

Links & Resources

• Free Co-Living Challenge – Learn Sam’s model at ScaleYourRealEstate.com
• Connect with Sam Wegert – Instagram: @SamWegert
• SmrtPhone – Get 5,000 free minutes with the only phone system built for real estate investors.
• ThatRealEstateTechGuy.com – All episodes, resources, and exclusive tech discounts.

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Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! Today, I’m thrilled to sit down with Trevor Mauch, founder and CEO of Carrot, one of the most influential lead-generation platforms in real estate. If you’re an investor, agent, or home-services pro, you’ve almost certainly used (or competed against) a Carrot site.

This episode goes far beyond lead gen. Trevor walks through how inbound marketing has evolved, how AI is reshaping online search, and why consistency beats speed every time. But where he really shines is in breaking down how to scale a business intentionally — from your first deal to seven figures. He shares his Entrepreneur Freedom Formula, the “pain lines” every business hits, and the identity shifts required to break through each revenue ceiling.

Episode Timeline & Highlights

[0:00] – Introducing Trevor Mauch and Carrot’s role in powering high-performing investor and agent websites.

[1:03] – Carrot’s growth, acquisition of InvestorFuse, and launch of Carrot CRM.

[1:57] – Why inbound leads produce the highest motivation, best margins, and fastest conversions.

[3:37] – How AI search is shifting consumer behavior — and what investors must adapt to.

[6:29] – The importance of marketing diversification once an investor begins scaling.

[8:25] – The power of integrated data: knowing which leads become deals and why.

[9:50] – How Carrot’s dataset fuels smarter AI, smarter targeting, and smarter follow-up.

[10:55] – Why tracking touchpoints per channel allows investors to spend more intelligently.

[13:57] – The future: humans handle the highest-value conversations; AI handles the rest.

[15:53] – The transformative impact of AI on staffing, hiring, and skill development.

[17:35] – Why resisting AI is the modern equivalent of resisting the internet in the ’90s.

[24:29] – The two journeys: start-up vs scale-up — and why each demands different thinking.

[26:09] – Trevor’s Entrepreneur Freedom Formula and why every cycle takes 2–4 years.

[27:32] – Purpose → Consistent Profits → Time & Energy → Renewed Vision.

[33:55] – When to begin evergreen marketing: SEO, credibility, content.

[34:46] – When to add your first CRM — and why you shouldn’t do it too early.

[36:17] – The 300k–1M phase: delegation, VA support, dialing in marketing, mastering your market.

[37:23] – The identity shift from performer to builder required to break seven figures.

5 Key Takeaways

1. Inbound is the foundation, but combining inbound + outbound produces true scale.
2. Unique data layered on AI is where the biggest wins will come — not AI alone.
3. Hyper-human content wins online as search shifts to reward authenticity over automation.
4. Every business hits “pain lines.” Breaking through requires a mindset shift and new systems.
5. What gets you to $750k won’t get you to $1M. You must transition from performer to builder.

Links & Resources

• Carrot / Carrot CRM – High-performing websites + CRM for investors and agents.
• Entrepreneur Freedom Formula – Download Trevor’s framework at TrevorMauch.com/freedom.
• SmrtPhone – Claim 5,000 free minutes, the phone system built for real estate investors.
• ThatRealEstateTechGuy.com – Explore every episode + exclusive tech discounts.

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Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! This week I’m joined by Chris Prefontaine, founder of Smart Real Estate Coach, who brings more than 34 years of real estate experience and one of the clearest perspectives on creative financing you’ll find.

Chris explains why creative financing isn’t just an “advanced strategy” — it’s actually one of the best ways for new investors to start. No banks, no big down payments, and no personal guarantees. We dig into how creative deals produce multiple paydays, why they work in any market cycle, and how his team mentors beginners through hands-on deal support across 80+ markets.

We also dive into mindset, focus, and the importance of mentorship — plus the role technology now plays in scaling training, reviewing seller calls, and eliminating the busywork that slows new investors down.

Episode Timeline & Highlights

[0:00] – Introducing Chris and why Jordan’s recording on the road.

[1:04] – How the 2008 crash led Chris to rebuild his business around creative financing.

[2:04] – What creative financing is and why it eliminates bank dependence.

[3:22] – Why creative deals are ideal for beginners, not just veterans.

[4:13] – The flaw with starting in wholesaling or fix-and-flip.

[5:11] – Creative strategies that thrive in any market condition.

[6:15] – How Chris’s program takes true beginners from zero to real deals.

[10:34] – The business rules he built after the crash — and still follows.

[12:00] – The three steps every investor needs: niche, mentor, focus.

[13:22] – Why shiny-object syndrome derails investors.

[14:21] – The problem with constantly chasing new leads.

[17:55] – How tiny skill improvements compound into real performance.

[18:42] – Deals aren’t the hard part — mindset and habits are.

[20:26] – How AI is transforming student coaching and call review.

[21:57] – Why modern tech has simplified what once required multiple systems.

[22:52] – How AI call scoring and coaching will reshape acquisitions.

[24:02] – Chris’s biggest tech mistake: adopting unproven systems too early.

[24:44] – Tech advice for beginners: research and follow your mentor’s stack.

[25:08] – Three essential tools for new investors: phone, task system, communication tool.

[26:25] – Avoiding “creative avoidance” inside your CRM.

[27:39] – Why listening to live seller calls builds confidence and skill.

[28:42] – Chris’s free books and YouTube deal breakdowns.

[29:32] – How to get his books completely free.

5 Key Takeaways

1. Creative financing works everywhere and avoids traditional lending hurdles.
2. Choose the niche that matches you, not the one that’s loudest online.
3. Mentorship collapses your learning curve and keeps you accountable.
4. Three years of focus beats constant pivots.
5. Use tech to simplify, not distract — task tools, communication platforms, and AI call review matter.

Links & Resources

• Smart Real Estate Coach – https://smartrealestatecoach.com/
• Free Books – Visit WickedSmartBooks.com/jordan for Chris’s free books.
• SmrtPhone – Claim 5,000 free minutes, the phone system built for investors.
• ThatRealEstateTechGuy.com – All episodes + exclusive tech discounts.

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Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! Today I’m joined by my friend Steve Trang, founder of Objection Proof AI, host of Real Estate Disruptors, and one of the most respected sales trainers in the real estate investing world.

In this episode, Steve and I dive deep into the intersection of real-world sales fundamentals and artificial intelligence. Steve has trained thousands of salespeople and consulted with nine-figure companies — and now he’s building AI tools that reinforce the exact sales skills he’s taught for years. We cover everything from empathy and active listening to call scoring, role-playing bots, and the future of voice agents that can qualify leads, schedule appointments, and eventually help close deals.

Episode Timeline & Highlights

[0:00] – Introducing Steve Trang and his evolution from top sales trainer to AI innovator.

[1:03] – Why Steve built Objection Proof AI and what problems it solves for sales leaders.

[2:55] – How the AI now handles call reviews, training, follow-up, and appointment setting.

[3:47] – Steve’s background: thousands trained, hundreds coached, and deep experience in real-world selling.

[7:56] – The real definition of empathy and how it translates into AI behavior.

[9:01] – Why robots can be better sales trainers than charismatic “natural” closers.

[11:58] – The classic sales mistake: offering solutions before understanding the problem.

[17:15] – Pattern visibility: how AI finally reveals true agent performance.

[19:19] – Using call reviews and feedback loops to help agents improve faster.

[23:20] – Role-playing bots as a training tool AND a hiring filter.

[27:55] – The gold mine in your CRM: reactivating old leads with AI.

[29:12] – Why outsourced call centers kill deals and how AI solves consistency.

[33:37] – The future of AI underwriting and real-time offer parameters.

[38:30] – Why AI will outperform low-level staff, not A-players.

[40:02] – Building companies made up only of top performers.

[47:33] – How to try Objection Proof AI and test the role-play or voice agent demos.

5 Key Takeaways

1. Empathy is the core sales skill — not emotion, but demonstrating true understanding. That’s what builds trust and closes deals.
2. AI amplifies real sales training, not scripts. It reinforces the exact skills top reps use.
3. Call scoring at scale changes everything. AI uncovers performance patterns no manager could ever catch manually.
4. Voice agents solve massive inefficiencies, from missed calls to dead follow-up sequences to reactivating CRM gold.
5. AI doesn’t replace A-players — it replaces C-players, allowing teams to run leaner, sharper, and more profitably.

Links & Resources

• Objection Proof AI – Upload a call or transcript for a free AI call analysis.
• Role-Play Bot Demo – Text ROLEPLAY to 33777.
• AI Appointment Setter Demo – Text CASH to 33777.
• SmartPhone – The only phone system built for real estate investors. Claim 5,000 free minutes.
• ThatRealEstateTechGuy.com – Explore all episodes and exclusive tech discounts.

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Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! Today, I’m joined by Andrew Lucas, a full-time investor, educator, and co-founder of the Deal Finders Club in Columbia, South Carolina. Andrew’s story is one that so many investors can relate to: starting with a few rentals, making the classic early mistakes, and finally deciding to treat real estate like a real business.

In this conversation, Andrew breaks down how he scaled from a handful of rentals to over 100 units, built his own property management company, launched a thriving meetup community, and now helps new investors skip the painful mistakes he made early on. We dive into his philosophy around systems, mentorship, the realities of property management, what separates hobbyists from professionals, and how technology should support — not distract — your investing journey.

Episode Timeline & Highlights

[0:00] – Introducing Andrew Lucas and his journey from accidental investor to owning 100+ rentals.

[1:45] – How Andrew and his wife became full-time investors and built multiple income streams.

[3:00] – The reality of property management and why Andrew eventually built his own PM company.

[4:06] – Lessons from the hospitality industry and how “being too nice” killed early profitability.

[5:07] – The turning point: painting rentals while 7–8 months pregnant and deciding to do things right.

[10:11] – How one lawsuit opened Andrew’s eyes to the responsibilities of being a landlord.

[11:34] – How good property managers preserve asset value and enforce necessary boundaries.

[17:13] – Helping beginners avoid mistakes and providing guardrails as they build their business.

[18:44] – The transformation from dreamer to operator: when investing becomes a real business.

[20:18] – Why it only takes three flips a year to look like a professional investor to lenders.

[22:04] – Understanding the power of repeatable systems to scale beyond your day job.

[25:22] – The essential beginner tech stack: good data, a reliable phone system, and a simple CRM.

[28:44] – Why missed follow-ups cost more deals than bad marketing ever will.

[30:54] – Data quality: how bad lists waste money, kill ROI, and break your entire sales process.

[34:12] – Data paralysis vs. action: why investors must focus on outliers, not vanity metrics.

[35:00] – How to connect with Andrew and join the Deal Finders Club community.

5 Key Takeaways

1. Treat real estate like a business. Early mistakes come from poor systems, unclear boundaries, and inconsistent processes.
2. Most investors shouldn’t self-manage. Property management is process-heavy and legally risky without the right expertise.
3. Community accelerates success. Meetups, mentors, and peers help investors skip years of trial and error.
4. Start simple with tech. Only buy tools when your current process breaks — not because they look cool.
5. Good data drives the whole machine. Clean lists, solid follow-up, and reliable communication systems generate consistent revenue.

Links & Resources:

• Andrew’s Tech-Enabled Phone Number – Text him at (803) 216-5750
• ThatRealEstateTechGuy.com – Listen to all episodes and secure exclusive tech discounts.

Closing

If you enjoyed this episode, please follow, rate, and review That Real Estate Tech Guy wherever you listen. Share it with someone who’s ready to build a real real estate business — not just dabble in it. Stay tuned for more practical conversations with the people shaping today’s investor tech landscape.