Kyle Wegg went from South Side Chicago and cannabis farms in Northern California to Bitcoin-funded BRRRRs, out-of-state partnerships, and industrial outdoor storage deals.

In this episode, he shares the wins, the losses (including a failed Thailand project), and the lessons that shaped how he invests today.

00:00 Intro 

01:22 Kyle’s Early Life & Hustle

06:35 Personal Development & Mindset

11:51 Bitcoin + Creative Financing

18:42 Scaling with Out-of-State Partners

30:46 Building Credibility with Partners

33:45 Investing Overseas (Thailand)

35:42 What Went Wrong in Thailand

36:04 Coming Back to the US & Using Bitcoin

45:25 Industrial Outdoor Storage (IOS) 101

57:43 Kyle’s Advice for New Investors

59:17 Kyle’s Mortgage & Funding Business

n this episode, Chris Thompson shares his 19-year journey from new agent to owning 28 rental properties.

We talk through his first deals, how he survived the 2008 market, what makes a true investor-friendly agent, and the creative finance strategies he uses today.

If you’re an agent looking to build long-term wealth, this one hits home.

00:00 Intro

04:44 Lessons Learned from His Dad

10:38 First Deal on the Courthouse Steps

15:07 Living Through the 2008 Crash

21:50 Scaling from Agent to Investor

29:01 Creative Finance & Subject-To

35:03 What Makes an Investor-Friendly Agent

36:55 Understanding the Buy Box

37:28 Working With Seasoned Investors

38:29 When Creative Deals Actually Make Sense

40:14 Relationships Over Transactions

41:34 How Chris Educates Sellers

44:59 Property Management Essentials

47:17 How to Vet a Property Manager

53:57 Balancing Business & Family

55:28 Advice for New Investors

59:11 Why Community Matters

01:05:18 Chris’s Coaching & Contact Info

We’re back with a full Q&A episode! From how we got started in real estate to scaling with HELOCs, DSCR loans, and private money — we’re answering the questions you’ve been asking. Perfect for agents, first-time investors, and anyone ready to turn knowledge into action.

00:00 Intro

01:25 How Ana Got Started in Real Estate

04:22 How She Scaled Her Rental Portfolio Fast

08:19 Nico’s First Steps Into Real Estate Investing

12:41 Biggest Lessons & Advice for New Investors

19:26 Should Investors Get a Real Estate License?

23:22 Why Most Agents Don’t Invest Themselves

30:04 Making Low Offers (The Smart Way)

30:17 Interest Rates & What’s Next for the Market

33:56 Creative Ways to Afford Property Today

36:40 Investor Loan Types Explained Simply

41:43 How Cash-Out Refinancing Really Works

44:44 Top Tax Write-Offs for Agents & Investors

48:28 Best News Sources for Market Updates

51:43 How to Find Clients as a New Agent

55:42 Our Future Goals & Investment Plans

01:00:07 Final Thoughts

Told she’d “never buy a house,” Rhiannon spent 20 years proving that wrong. Pivoting from reality TV to out-of-state rentals and BRRRRs in Syracuse. Nico and Anna dig into her first 2% deal, why she chose mid-term rentals, how a ride-or-die agent changed everything, and the community that sped up her learning curve. Practical, transparent tips for new and scaling investors.

Chapters
00:00 Intro
01:01 Meet Rhiannon (TV → REI)
02:19 Why real estate, why now
07:48 First deal in Syracuse (2-unit)
15:33 Mid-term rentals (travel nurses)
22:07 BRRRR: buy → rehab → rent → refi → repeat
25:54 Creative financing 101
26:41 Building the bench (contractors, PMs)
28:36 Finding a go-getter agent
32:35 Scaling with discipline (numbers first)
44:31 Community as a cheat code
46:25 Parting advice for beginners

Turn renovation spend into luxury travel. Jaina shares how she’s secured $200k in 0% APR business credit, converts expenses into assets, and redeems points for premium trips. Learn bank-relationship tactics, when 3% fees make sense, best cards by investor type, charge vs credit cards, the Player Two spouse strategy, and how VAs can run 95% of ops. Plus, details on her Travel Hacker Accelerator.00:00 Intro02:00 CA to IN: 10-door playbook08:30 VAs that run the backend11:17 Paying contractors by card15:32 When the 3% fee is worth it18:07 Points value: 60k Chase vs 100k Hilton24:32 Hitting limits and what to do26:31 Best cards for realtors, flippers, STRs28:34 Charge vs credit cards30:54 In-branch approvals and bank relationships36:06 Player Two spouse strategy38:47 Free webinar and course

Follow Jaina- https://www.instagram.com/jaina_anne/

In this episode of the Agent to Investor podcast, we share Nico’s guest appearance on Ricky Ricardo’s show. Nico walks through his journey from agent to investor, covering the challenges of starting during the pandemic, finding off-market deals, and leveraging his construction background through family ties.

At its core, this episode is about navigating the agent2investor transition with clarity, community, and a focus on long-term financial freedom.

Timestamps:
00:00 Intro
01:22 Nico’s Start in Real Estate
02:01 Transitioning to Investing
06:09 Making Competitive Offers
09:28 Balancing Agent vs. Investor
21:26 Setting Expectations with Sellers
25:09 Nico’s First Investment Property
28:12 Learning Landlording & Scaling
29:44 Networking & Meetups
35:15 Flip & Rental Case Study
41:00 Foreclosures & Bankruptcies
48:52 Personal Interests & Goals
50:43 Closing Thoughts

Connor Schwartz, a real estate agent and investor from Syracuse, New York. Connor shares his inspiring journey from studying construction management to becoming a successful real estate investor.

Learn about the power of persistence, the importance of mentorship, and how to navigate tenant-friendly markets.

Connor also discusses the booming opportunities in the Syracuse market with the upcoming Micron technology plant, expected to bring significant growth and development to the area.

This episode is packed with valuable insights for both new and seasoned investors. Don't miss out!

Chapters:

00:00 Introduction 

01:23 Connor's Journey into Real Estate

05:27 Finding a Mentor

13:28 First Real Estate Deal

15:09 Tenant Management and Screening

22:44 Tenant Screening Success Stories

23:32 Safeguarding with Flexible Leases

25:18 Scaling Through Partnerships

29:19 Navigating the Syracuse Real Estate Market

36:28 The Impact of Micron Technology on Syracuse

40:16 Personal Insights and Future Plans

In this episode we have Brian Anleu, Brian dive into the world of real estate and local policy in Montgomery County, Maryland. Brian, with his unique background working for the county government, reveals the surprising and often unseen forces shaping the housing market.

They discuss everything from the struggle of first-time homebuyers to the surprising "lock-in effect" of low interest rates, and how 40% of a new building's cost is tied directly to regulation and permitting.

This is a deep and insightful conversation on why it's so difficult to build and buy homes today, and what can be done to fix it.

We sit down with Kentucky investor & civil engineer Joel Sizemore to break down simple plays that work right now: door-knocking for off-market deals, the 30% discount rule, turning an unfinished basement into 2 beds / 2 baths, and using 30+ day mid-term rentals near hospitals to boost cash flow—no STR permit needed.

Joel also shares his “cash offer → quick refi” approach with a local credit union, and how he closes without an agent (lawyer + title combo).

Timestamps:

00:00 Intro

01:23 Joel’s start

03:26 First deal + challenges

06:04 Engineer edge

11:18 Reno + house hack

17:36 Mid-term rentals

19:46 Next property

20:56 Legal & contracts

22:23 Door-knocking

22:52 No-agent route

25:31 Creative financing

28:38 Local market picks

32:42 Community & accountability

34:49 Final takeaways

Connect with Joel- https://www.instagram.com/joelsizemoreky/

If this helped, like & subscribe and comment what we should cover next.