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Jan 31, 2023

Welcome to Part 2 of my conversation with real estate investor and founder of Cashflow Diary - J. Massey.

We open Part 2 of Make Money In The Sharing Economy with J’s perspective on ordinances and bylaws that dictate where short term rentals (STR’s) are allowed, where they’re not, and why he’s actually a fan of these rules.

J also reveals;

  • often overlooked segments of the population that need extended stay accommodation,
  • opportunities to rent out your house or condo for day use ; for example – to content creators,
  • other ways you can earn money in the shared economy,
  • the most common oversights and mistakes made by people entering the STR business,
  • and he walks us through the numbers of what it takes to net $1,000 and $2,000 per month from your STR

Like Part 1, this episode is ripe with light bulb moments to inspire your side hustle journey.


What You’ll Hear:

03:35 The ordinances are forcing you into a more profitable part of the business

04:20 All these groups in the “extended stay” category need places to stay

06:25 Government organizations can be a worthwhile source of guests

08:01 J walks us through the numbers to net $1000 and $2000 per month

09:37 Biggest expense is the lease (or mortgage), then labour-related issues

09:57 Start your projections with a revenue number being double what you’re paying for the lease

10:28 Worse case you should expect is a net income of 30% of revenues

11:35 “Tent pole” or “Compression” events coming to town drive up nightly rates

13:09 “Damage fee waiver” vs “security deposit”

14:18 Only 60% of J’s gross revenues are from the nightly rates, 40% are the “add-ons”

14:30 Other “add-on” ideas to receive revenue from guests

16:00 Opportunities in “day-use” property rentals

17:50 Expenses that are sometimes overlooked in budgets

18:06 You need to pay attention to “screening, safety, and security,” to avoid liability, a lot of problems, and increased labour costs

22:11 Where to look for your first short term rental property

25:15 Other rental opportunities from assets you now own

26:43 J’s best tip for taking action

27:52 Focus on being “prepared” rather than waiting to be “ready”

Wrap Up:

29:01 Fail fast, fail forward, fail frequently and start before you’re ready

29:25 A confidence-building mindset to adopt - What would I do differently next time? What went right?

Connect with J Massey:

J’s Short-Term Rental Blueprint Course

Connect with Joan:

Be on the show!