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

Closing

If you enjoyed this episode, please follow, rate, and review That Real Estate Tech Guy. Share it with an investor who wants to understand creative finance the right way — without shortcuts, hype, or ethical gray areas. More high-signal conversations are coming next.

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

Closing

If you enjoyed this episode, please follow, rate, and review That Real Estate Tech Guy. Share it with an investor who’s tired of plateaus and ready to build something scalable, durable, and real. More conversations with operators who’ve actually done the work are coming next.

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.

Closing

If you enjoyed this episode, please follow, rate, and review That Real Estate Tech Guy. Share it with an investor who’s scaling fast but still wondering where the money went. Strong fundamentals build real freedom — and more great conversations are coming next.