Agent2Investor Podcast

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 & Hustle06:35 Personal Development & Mindset11:51 Bitcoin + Creative Financing18:42 Scaling with Out-of-State Partners30:46 Building Credibility with Partners33:45 Investing Overseas (Thailand)35:42 What Went Wrong in Thailand36:04 Coming Back to the US & Using Bitcoin45:25 Industrial Outdoor Storage (IOS) 10157:43 Kyle’s Advice for New Investors59:17 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 Intro04:44 Lessons Learned from His Dad10:38 First Deal on the Courthouse Steps15:07 Living Through the 2008 Crash21:50 Scaling from Agent to Investor29:01 Creative Finance & Subject-To35:03 What Makes an Investor-Friendly Agent36:55 Understanding the Buy Box37:28 Working With Seasoned Investors38:29 When Creative Deals Actually Make Sense40:14 Relationships Over Transactions41:34 How Chris Educates Sellers44:59 Property Management Essentials47:17 How to Vet a Property Manager53:57 Balancing Business & Family55:28 Advice for New Investors59:11 Why Community Matters01:05:18 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 Intro01:25 How Ana Got Started in Real Estate04:22 How She Scaled Her Rental Portfolio Fast08:19 Nico’s First Steps Into Real Estate Investing12:41 Biggest Lessons & Advice for New Investors19:26 Should Investors Get a Real Estate License?23:22 Why Most Agents Don’t Invest Themselves30:04 Making Low Offers (The Smart Way)30:17 Interest Rates & What’s Next for the Market33:56 Creative Ways to Afford Property Today36:40 Investor Loan Types Explained Simply41:43 How Cash-Out Refinancing Really Works44:44 Top Tax Write-Offs for Agents & Investors48:28 Best News Sources for Market Updates51:43 How to Find Clients as a New Agent55:42 Our Future Goals & Investment Plans01:00:07 Final Thoughts

Learn the entire first-time buyer journey - from pre-approval to keys, plus myths (you don’t need 20% down), offer tactics, inspections/appraisals, grants, house hacking, and six pro tips to avoid costly mistakes.00:00 Intro01:21 First-Time Buyer Stories & Tips03:09 Why Own vs Rent05:05 Affordability: Facts & Myths11:01 Home-Buying Steps (Start to Close)19:50 Don’t Add Debt Before Closing20:19 Appraisals: What They Do21:53 Who Pays: Inspections & Appraisal22:40 Final Walkthrough + Closing Disclosure26:33 Quick Recap: The Steps27:48 Pro Tips for First-Time Buyers28:12 Prep Right: Savings + Credit31:30 Set Realistic Expectations33:01 First-Time Buyer Programs (Grants)34:36 Why Your Inspection Matters36:48 Bonus Tips & Wrap-Up

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.Chapters00:00 Intro01:01 Meet Rhiannon (TV → REI)02:19 Why real estate, why now07:48 First deal in Syracuse (2-unit)15:33 Mid-term rentals (travel nurses)22:07 BRRRR: buy → rehab → rent → refi → repeat25:54 Creative financing 10126:41 Building the bench (contractors, PMs)28:36 Finding a go-getter agent32:35 Scaling with discipline (numbers first)44:31 Community as a cheat code46:25 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 courseFollow 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 Intro01:22 Nico’s Start in Real Estate02:01 Transitioning to Investing06:09 Making Competitive Offers09:28 Balancing Agent vs. Investor21:26 Setting Expectations with Sellers25:09 Nico’s First Investment Property28:12 Learning Landlording & Scaling29:44 Networking & Meetups35:15 Flip & Rental Case Study41:00 Foreclosures & Bankruptcies48:52 Personal Interests & Goals50:43 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 Estate05:27 Finding a Mentor13:28 First Real Estate Deal15:09 Tenant Management and Screening22:44 Tenant Screening Success Stories23:32 Safeguarding with Flexible Leases25:18 Scaling Through Partnerships29:19 Navigating the Syracuse Real Estate Market36:28 The Impact of Micron Technology on Syracuse40:16 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.

In this engaging discussion, Joel Sizemore, a Kentucky investor and civil engineer, shares his insights on building wealth through real estate. He reveals his strategies for finding off-market deals through door-knocking and highlights his 30% discount rule on property purchases. Joel shares the benefits of converting basements into rental units and leveraging mid-term rentals near hospitals for extra cash flow. He discusses his unique approach to financing and closing deals without an agent, offering practical tips for aspiring investors.