--- title: Stepping Over Pennies For Dollars - Ryan Dossey description: 26-year-old, Indianapolis real estate investor, Ryan Dossey joins Matt to discuss his $9M RE portfolio, call center, and more. Tune in now! image: https://learn.upright.us/hubfs/ryan.png --- [![Upright Real Estate Investment](https://learn.upright.us/hs-fs/hubfs/Upright_RGB_PrimaryLogo-2.png?width=175&height=42&name=Upright_RGB_PrimaryLogo-2.png "Upright Real Estate Investment")](https://upright.us/) [![Return Home >](https://no-cache.hubspot.com/cta/default/2129804/90add894-e0b2-4f0c-bc22-7c5b348dd1d7.png)](https://cta-redirect.hubspot.com/cta/redirect/2129804/90add894-e0b2-4f0c-bc22-7c5b348dd1d7) [Back to the Blog](https://learn.upright.us/real-estate-investing-unscripted-podcast) # Stepping Over Pennies For Dollars - Ryan Dossey July 30, 2020 | By [Upright](https://learn.upright.us/real-estate-investing-unscripted-podcast/author/upright) Sign up and get updates sent directly to your inbox. **Subscribe to Real Estate Investing Unscripted on [Apple Podcasts](https://itunes.apple.com/us/podcast/real-estate-investing-unscripted/id1411541971), [Google Podcasts](https://podcasts.google.com/search/fund%20that%20flip), [Stitcher](https://www.stitcher.com/podcast/fund-that-flip/real-estate-investing-unscripted), or [Spotify](https://open.spotify.com/show/5IH5wU6bzcwtBks57XNI9P).** ![Indianapolis real estate zen master, Ryan Dossey joins Matt to discuss his real estate journey. Ryan has built a $9M real estate empire, has a real estate investor specific direct mail and call center, and runs one of the country's top real estate networks, all at the age of 26.](https://learn.upright.us/hs-fs/hubfs/circle-cropped%20(4).png?width=186&name=circle-cropped%20(4).png) On this episode of Real Estate Investing Unscripted, Indianapolis real estate zen master [Ryan Dossey](https://ryandossey.com/) joins Matt to discuss his real estate journey. Ryan has built a $9M real estate empire, has a real estate investor specific direct mail and call center, and runs one of the country's top real estate networks, all at the age of 26. Ryan's real estate career started while he was still grinding in car warranty sales simply to pay the bills. Despite making good money, Ryan knew this was not what he was meant to do. After using platforms like [Bigger Pockets](https://www.biggerpockets.com/) to learn more about real estate, he began wholesaling and then quit his job, confident that he could find success in real estate investing. He then started [Call Porter](https://www.callporter.com/) in 2015, a U.S. based, live-answering service. Ryan also discusses how the COVID-19 pandemic has impacted his business and shares best practices for real estate investors in uncertain times. Matt and Ryan close their conversation by discussing the challenges with [insurance and real estate - click here to read our blog article on the subject!](https://learn.upright.us/real-estate-investing-blog/insurance). Tune in below: **Subscribe to Real Estate Investing Unscripted on [Apple Podcasts](https://itunes.apple.com/us/podcast/real-estate-investing-unscripted/id1411541971), [Google Play](https://play.google.com/music/m/Iertxcaxr37vopllog4fbmrexxy?t=Real_Estate_Investing_Unscripted), [Stitcher](https://www.stitcher.com/podcast/fund-that-flip/real-estate-investing-unscripted), or [Spotify](https://open.spotify.com/show/5IH5wU6bzcwtBks57XNI9P)** - - - ### Start Transforming Your Investment Property Now [![Apply Now](https://no-cache.hubspot.com/cta/default/2129804/3420ff91-259d-4238-ae5b-bda78b01cff5.png)](https://cta-redirect.hubspot.com/cta/redirect/2129804/3420ff91-259d-4238-ae5b-bda78b01cff5) ### Looking for an alternative to stocks? Real estate investing can earn up to 12% annual returns on pre-vetted, low LTV, real estate-secured loans. Fund That Flip offers industry-leading visibility into each project, enabling investors to be highly selective in the loans they choose to fund. 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