Lessons Learned: Going From a $50k First Flip Loss to Doing 70 More

by | Nov 8, 2026 | Investing in the US, Podcast, Real Estate, Real Estate Investing | 0 comments

Eli Stoner bought his first investment property in 2022, before he’d even left school. He funded it with private money, did the construction himself with college friends, and lost about $50,000. He kept going. Four years later he’s flipped around 70 homes across Central Indiana. He’s also a licensed realtor and a former wholesaler.

Sarah and Ryan met Eli by chance. He was the Zillow agent assigned to them while they were browsing Indy’s Lockerbie Square neighbourhood. In this episode he breaks down how he sources deals, why he scaled back after a rough year, and what Canadians should know about investing in Indianapolis.

In this episode:

  • Eli’s story, from Columbus, Ohio to the University of Indianapolis, and the $50K loss on deal #1 (08:20)
  • His lean team: one VA, a part-time bookkeeper and a business partner (10:30)
  • His daily outreach system: 20 “as-is” agents and 10 wholesalers a day into a CRM (11:00)
  • How to add value to wholesalers when you’re not the highest bidder (12:55)
  • Why he chose flipping: high active income first, then long-term holds (18:10)
  • The scaling mistake: trying to double volume and buying the wrong deals (19:30)
  • Hidden rehab costs: interest, insurance, utilities, dumpsters and a 10% contingency (22:15)
  • Why builder-grade gray no longer sells, and how he uses AI design sheets with contractors (25:30)
  • His read on the Indy market: days on market, pending sales and the areas he avoids for flips (29:45)
  • Two exit strategies on every deal, and why he caps resale around $450K (30:55)
  • What to do when a flip sits: restage, re-shoot, and treat every showing like a lead (33:50)
  • Why he got his real estate license (35:55)
  • Why invest in Indy: a $280K–$300K median price, jobs, events and people moving in (41:30)
  • His advice for getting started: stop overanalyzing and take action (43:20)

This episode has been brought to you in part by:

Ryan Carson, Carson Law – https://www.carsonlaw.ca/ or email ryan@carsonlaw.ca

Matt Pickering, National Bank matthew.pickering@nbc.ca

Connect with Eli:

Website: https://livindyrealty.com/agent/eli-stoner

Email: elistoner@livindyrealty.com

Instagram: http://www.instagram.com/eli_stoner/

LinkedIn: https://www.linkedin.com/in/eli-stoner-2846a325a/

 

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