Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! This week’s episode is a deep, practical dive into private money, and I’m joined by Jay Conner, one of the most respected educators in the space and someone who has raised millions of dollars for real estate deals without ever chasing banks or hard money lenders.

Jay breaks down private money in a way that removes the mystery, fear, and emotion that stops most investors from ever using it. We talk through when investors should start raising private money (hint: much earlier than most think), how to structure deals so lenders are protected, and why the math — not motivation — determines whether a deal works.

Episode Timeline & Highlights

[0:00] – Introducing Jay Conner and why private money changed everything for his business.

[1:40] – Why this episode focuses more on real estate fundamentals than pure tech.

[2:34] – Jay’s early years relying solely on banks — and the 2009 shift to private money.

[3:45] – Raising over $2M in less than 90 days without pitching deals.

[5:08] – When investors should start using private money (even beginners).

[7:27] – Thinking of private money as a personal line of credit.

[8:04] – Why lenders want their money deployed and are waiting for your call.

[8:33] – Why private money works best for fix-and-flip and asset-backed deals.

[9:25] – Walking through a real flip example using private money.

[12:06] – Jay’s maximum allowable offer formula explained step by step.

[13:34] – Why math removes emotion from offers.

[14:39] – Adjusting formulas based on market price points.

[16:13] – Leveraging past success and partnerships when you’re new.

[18:29] – Why private money is asset-backed and protects lenders.

[21:31] – Why the SEC doesn’t regulate single-asset private money deals.

[22:59] – Jay’s Private Money Academy and how beginners get started.

[24:10] – Monthly coaching, deal reviews, and live Q&A for members.

[24:59] – Jay’s bestselling book Where to Get the Money explained.

[25:27] – Two free tickets to Jay’s live private money conference.

[27:00] – Where AI fits — and doesn’t fit — in deal analysis and underwriting.

[36:55] – Why consistency beats charisma every time.

[38:25] – How to claim Jay’s free resources and connect with him.

5 Key Takeaways

1. Raise the money before you need it. Private money works best when there’s no desperation.
2. Math beats emotion. If the numbers work, the deal works — period.
3. Private money is asset-backed. Lenders are protected by the property, not your promises.
4. Beginners can raise private money. Past success, partnerships, and integrity matter more than deal count.
5. AI supports experience — it doesn’t replace it. Use technology with guardrails, not blind trust.

Links & Resources

• Private Money Academy – First month free at jayconner.com/trial
• Free Book: Where to Get the Money – Autographed copy + 2 conference tickets: jayconner.com/book
• 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 my good friend Nick Lamagna, host of the A Game Podcast and one of the most eclectic, disciplined, and grounded investors I know. This conversation goes far beyond real estate and turns into a deep dive on performance, mindset, and what actually separates people who last from those who burn out.

Nick shares his unconventional journey into real estate, how an early setback forced him into remote investing long before it was popular, and why fundamentals always matter more than hype. We talk about building buy boxes through action, learning markets by doing deals, and why chasing “shiny” strategies is usually the fastest way to stall out.

Episode Timeline

[0:00] – Introducing Nick Lamagna and his background as a high performer across multiple disciplines.

[1:52] – Why principles of success are universal — and why most people don’t apply them.

[2:37] – Nick’s early move into remote investing out of necessity, not trend-following.

[3:58] – Starting in competitive markets with no money or credit and being forced to adapt.

[5:17] – Discovering that the entire country can be your buy box.

[6:05] – Why cheap properties often come with expensive problems.

[7:12] – The danger of buying “cash flow on paper” without performance reality.

[8:44] – Finding the balance between affordability, stability, and appreciation.

[14:05] – Why surrounding areas benefit when people get priced out of cities.

[15:10] – Sticking to sensible parameters instead of chasing shiny wins.

[16:15] – Building buy boxes by throwing a wide net and learning through offers.

[17:45] – Training agents and teams by giving real feedback through reps.

[19:01] – Why confidence comes from action, not theory.

[21:19] – The danger of “one-strategy-only” thinking for newer investors.

[23:08] – Fundamentals never change, regardless of market cycles.

[29:27] – “Have bad days, not bad deals” — addressing issues immediately.

[31:02] – Using video, accountability, and systems to manage properties remotely.

[33:44] – Discipline over ego: lessons from jiu-jitsu, boxing, and business.

[36:05] – Why effort is the real secret behind “effortless” success.

[38:49] – Technology improves visibility, but discipline must come from the operator.

[42:22] – Nick’s podcast, community, and why he focuses on high performers across industries.

[45:39] – How to connect with Nick and collaborate on future deals.

5 Key Takeaways

1. Fundamentals always win. Markets, tools, and strategies change — principles don’t.
2. Remote investing works when systems replace proximity. Visibility beats geography.
3. Cheap deals often hide expensive problems. Performance matters more than price.
4. Technology is an equalizer, not a substitute for discipline. Tools only work if enforced.
5. High performers share the same habits across every field. Effort creates “effortless.”

Links & Resources

• The A Game Podcast – High performers across real estate, sports, and business
• NickLamagna.com – Podcast links, socials, and resources
• 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! This episode is a fun one, and honestly, it goes a little off the rails in the best possible way. I’m joined by Kenner French, author, AI expert, and founder of Vast Solutions Group, and the conversation quickly turns into a full-on deep dive into what it actually means to become an AI-first entrepreneur.

Kenner is the author of the Amazon bestselling book Modern Millionaires AI, and he’s been working with artificial intelligence since long before it was cool. In this episode, we talk about how AI isn’t just about automation or shiny tools — it’s a mindset shift. One that changes how you think, create, build, and scale businesses. From tax strategy and asset protection to product design, voice technology, and AI agents, Kenner shares why AI will fundamentally reshape entrepreneurship over the next decade.

Episode Timeline & Highlights

[0:00] – Introducing Kenner French and why this episode goes deep fast.

[1:15] – Kenner’s background as an AI expert, author, and longtime entrepreneur.

[1:50] – Modern Millionaires AI and the core idea: make millions, save millions, protect millions.

[2:22] – Why AI can help with financial growth, tax savings, and asset protection.

[4:14] – Why most people misunderstand what AI is actually good at.

[5:03] – The “AI-first” mindset and the moment everything clicks.

[6:01] – Using AI as a thinking partner, not just an automation tool.

[9:06] – The danger of companies pretending to be AI-first without actually changing.

[10:11] – Why AI today is the worst it will ever be — and why that matters.

[11:09] – How AI accelerates product design, prototyping, and decision-making.

[12:00] – “Vibe coding” explained and why ideas now matter more than syntax.

[13:06] – Live examples of building apps and tools by talking to AI.

[14:32] – Why infrastructure, scale, and compliance still matter.

[18:31] – Why humans + AI together reduce error rates better than either alone.

[19:28] – AI’s role in lowering costs and increasing access to services.

[21:01] – Why slow-moving industries like tax and accounting are being forced to adapt.

[22:35] – Open-source AI, consulting models, and the future of SaaS.

[36:05] – The future of work, universal income, and societal shifts.

[38:22] – AI, quantum computing, and the scale of change ahead.

[42:22] – Final thoughts on entrepreneurship, mindset, and Modern Millionaires AI.

5 Key Takeaways

1. AI-first is a mindset, not a toolset. It changes how you think, not just how you automate.
2. AI enhances humans — it doesn’t replace them. The real power comes from collaboration.
3. Ideas now matter more than execution speed. AI compresses build times dramatically.
4. Context and memory are everything. AI agents that remember outperform scripts every time.
5. Early adopters will build massive moats. Waiting to “see how it plays out” is the riskiest move.

Links & Resources:

• Modern Millionaires AI – https://a.co/d/6I98SqK
• Vast Solutions Group – https://vastsolutionsgroup.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 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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