About me

Side hustle investor turned full-time operator.

I grew up in New York, played golf for Hofstra University, and worked enterprise technology sales — until real estate gave me the option to walk away. These days I split time between Raleigh, Florida, and Long Island.

Jonathan Farber

The path so far

  1. Ages 21–25

    House hacking

    Started by living in and renting out my own places — learning the fundamentals of real estate with the training wheels on.

  2. Corporate years

    Enterprise tech sales by day, deals by night

    Built the portfolio as a side hustle: traditional rentals, then short-term rentals and Airbnb arbitrage, using creative acquisition and financing strategies.

  3. Age 27

    Financial freedom

    Rental income covered my life. I left the corporate job to go all-in on real estate, podcasting, and helping others follow the same path.

  4. Today

    Systems, team & sharing the playbook

    I've trained 5+ virtual assistants who run the day-to-day, host The Scaling Made Simple Podcast, and run 7 Day Bookkeeper so hosts and small business owners get clean books without the headache.

The best of what I've learned is free

Start with the blog — Airbnb investing step by step, hiring virtual assistants, and the tools that run my business.