1001: Getting out of the Military and into Real Estate – Shelby Osborne

November 15, 2021

Are you considering a career change? Today’s guest, Shelby Osborne, decided to get out of the military and into real estate. Since making the switch, Shelby’s found more freedom, made more money, and has had the chance to help other veterans achieve their homeownership goals. Listen and learn about getting started in real estate as an agent and as an investor. Catch Shelby’s can’t-miss tips on winning clients, closing real estate deals, and more.

Listen to today’s show and learn:

  • About Shelby Osborne [0:51]
  • The book that shaped Shelby’s business [1:51]
  • North Carolina’s real estate markets [3:02]
  • Why Shelby got into real estate [3:53]
  • Shelby’s first investment property [6:44]
  • Transitioning out of the military and into real estate [7:59]
  • Shelby’s first year working exclusively with buyers [8:38]
  • Shelby’s real estate team [12:39]
  • How to determine what sellers really want [15:34]
  • Where Shelby finds real estate deals [20:14]
  • A marketing system for off-market homes like the MLS [21:08]
  • Shelby’s sales stats [22:38]
  • How Shelby closed 48 deals her first year in real estate [24:20]
  • Pitching to people eligible for VA loans [28:08]
  • David Greene’s BRRRR real estate investment strategy [31:36]
  • Advice on starting a real estate team [35:28]
  • How to host a real estate meetup [40:56]
  • Ways to monetize meetup leads [43:27]
  • The power of real estate investing [45:30]
  • Shelby’s predictions on the real estate market [46:19]
  • About Pillar Consulting [48:10]
  • Why there is no easy button in real estate [49:37]
  • Where to learn more about Shelby [52:35]

Shelby Osborne

Shelby graduated from the University of South Carolina in 2012, served in the Army for 6 years and got out as a Captain in the beginning of 2018 to dive into Real Estate full time as both a broker & investor in Fayetteville, NC.

Following her first year as a broker, Shelby was recognized as the Keller Williams Rookie of the Year for the “Carolinas Region” (all of North & South Carolina) and began to expand, creating her own team of real estate professionals. Five Pillars Realty Group became official in 2019 and expanded to Charlotte, NC in 2020. Both Fayetteville & Charlotte offices specialize in helping military and investors nationwide meet their goals. “Pints & Properties,” their Real Estate Investors meetup, is booming & continuing to grow rapidly.

Meanwhile, Shelby was relentless in growing her rental property portfolio. Since purchasing her first intentional rental property in November 2017, she now owns 74 units, acquired using several different strategies and comprised of a little bit of everything: single-families, residential multi-family, commercial multi-family and short-term rentals… plus a bit of airbnb arbitrage.

Between CEO duties and continuing to invest, Shelby operates “Pillars Consulting” – a company designed to transform Real Estate Brokers into their full potential — and “Life & Lens Photography” — a company designed to showcase Multi-Family Syndication projects and help investors raise private capital.

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-Aaron Amuchastegui

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