Financial Freedom with Real Estate Investing

‘Don’t worry about everything you don’t know today.’

Josh Sterling’s advice for aspiring real estate investors? Jump in head first and take massive action. In fact, if Josh could go back and offer some advice to his 17-year-old self, he would recommend skipping college and getting on the fast track to multifamily as soon as possible!

But Josh didn’t know that then, and he pursued a degree in aeronautical science from Embry-Riddle University. He got a job as a commercial airline pilot and had worked his way up to captain when the recession hit, and his hard work was rewarded with a demotion and a pay cut. Josh decided then and there that he needed a side hustle that he could control, and he landed on real estate. Josh was eventually able to quit his job and pursue real estate full-time, growing his portfolio to a cool 250 units.

Josh has also grown his business, building out his own property management team. Today he walks us through his first deals in the single-family space, discussing the challenges of managing 25 properties and how that struggle inspired his shift to multifamily. Josh offers his insight around building relationships with a few good brokers, describing how he has scaled to 250 units with the help of just two realtors. He explains his approach to multifamily syndication, sharing how multifamily allowed him to quit his job, go to work on his own terms, and have lunch with his 18-month old daughter any time he wants. Listen in for Josh’s advice about establishing credibility—with or without a track record—and getting on the fast track to multifamily.

Key Takeaways

What inspired Josh to pursue real estate

  • Working as airline pilot
  • Demotion with pay cut in 2008
  • Looking for something could control

Josh’s first deal in September 2009

  • $40K single-family in southeast Michigan
  • Buy and hold strategy

Why Josh made the shift to multi-family

  • Owned 25 single-family rentals by 2012
  • Needed help with management
  • Multifamily necessary to scale business

Josh’s first multifamily deal

  • Colleague introduced to commercial broker
  • Approached with 24-unit off-market deal
  • Couldn’t get numbers to work, deal fell apart
  • Seller reached out twelve months later
  • Bought under land contract for $515K at 6%
  • Upgraded units, occupancy rose from 42% to 100%
  • Cash out refi after 14 months (valuation at $800K)

Josh’s next multifamily deal

  • Same broker approached with 53-unit deal
  • Used capital from refi of 24-unit property

Josh’s approach to raising money

  • Share enthusiasm for real estate with family, friends
  • Leverage portfolio for credibility

Josh’s first experience with syndication

  • $1.3M building under contract
  • Needed to raise $300K to close
  • Put out sample deal package
  • Fully subscribed in 24 hours

How quitting his day job changed Josh’s life

  • Left in May of 2016 (owned 140 units)
  • Work on own terms to grow business
  • Aggressively looking for deals
  • Fly to play golf, see concerts

What Josh would tell his 17-year-old self

  • Skip college, buying first home
  • Pursue multifamily right away
  • View regular job as means to end

How to fast track a career as a real estate investor

  • Get educated quickly
  • Build relationships with brokers
  • Don’t worry about bank financing
  • Demonstrate credibility to raise equity

What Josh is excited about right now

  • Building own property management team
  • Building self out of day-to-day operations
  • Focus on networking, maintaining broker relationships

Josh’s advice for aspiring real estate investors

  • Take massive action
  • Build reputation, relationships

Connect with Josh


Epic Property Management



Freddie Mac Small Balance Loan

Entrepreneurs’ Organization

Michael’s Coaching Programs

Free eBook: The Secret to Raising Money to Buy Your First Apartment Building

Review the Podcast on iTunes

Direct download: MB_091-The_Fast_Track_to_Multifamily__With_Josh_Sterling.mp3
Category:Commercial Real Estate -- posted at: 12:20pm EST