Side Hustle Hero

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:

• https://cashflowdiary.com/
• https://www.instagram.com/cashflowdiary/

J's Short-Term Rental Blueprint Course

• https://cashflowdiary.com/blueprint/

Connect with Joan:

• https://www.instagram.com/joanposivy/
• https://www.facebook.com/posivy/
• https://www.joanposivy.com/

Be on the show!

• https://www.joanposivy.com/be-our-guest.html

Today's guest sees "oceans of opportunity" everywhere!

J Massey was all but "retired" at the age of 38, when one of his students asked what he knew about short-term rentals. While the answer at the time was, "not very much", he started looking into the model and was astounded at the opportunities. Today J runs a 34 unit short-term rental business, and runs a training company known as Cashflow Diary, helping others to get established and grow in the industry.

In this, Part 1 of 2 episodes with J, you'll hear;

• What's now driving the short term rental market,
• The multiple income sources you can set up to create earnings over and above the nightly rent,
• How you can establish a short term rental side hustle without even owning a property,
• And other income opportunities outside of the real estate space, but in the shared economy

J also shares his "super secret" of how he bought and sold over 200 properties each in 72 hours or less, earning him between $2000 and $26,000 " per property.

You're sure to have lightbulb moments, as you listen to my conversation with today's side hustle hero, J Massey.

What You'll Hear:

03:35 Needing to eat was a strong motivation

05:06 How we talk ourselves out of moving forward

06:50 How J bought and sold properties within 72 hours…200 times

10:28 J feels is the perfect time to get into real estate

11:10 Oceans of opportunity exist today

13:35 The way real estate is being used is changing

16:40 Set yourself up so that your income is no longer tied to your labour nor a clock

17:40 Earn money from idle assets that you already own

20:00 Keep "screening, safety, and security" in the forefront when renting out your assets

21:30 View your short-term rental (STR) properties as a "distribution" service to maximize revenue

26:00 Get into the STR business without owning the properties

28:09 Dealing with pushback from landlords when trying to lease properties

30:47 How to look at the new rules, regulations, ordinances concerning STR's

Connect with J Massey:

https://cashflowdiary.com/

https://www.instagram.com/cashflowdiary/

J's Short-Term Rental Blueprint Course

https://cashflowdiary.com/blueprint/

Connect with Joan:

• https://www.instagram.com/joanposivy/
• https://www.facebook.com/posivy/
• https://www.joanposivy.com/

Be on the show!

• https://www.joanposivy.com/be-our-guest.html

Are you that person in your friend group who likes to play matchmaker? Or maybe you know someone who does?

Today's guest, Siobhan Copland, is so good at it that she grew her side hustle into the London, UK-based, award-winning dating agency Cupid in the City.

Dive into today's episode for insights into what you can expect to earn as a matchmaker, where to find clients, and if you're looking for love, why dealing with a respected matchmaking service is such a completely different experience than swiping right or left on a dating app.

What You'll Hear:

02:11 Juggling 4 side hustles

04:43 Comedy shows led to speed dating

07:09 Being fired from full time work opened a door

08:10 Receiving the best advice - "don't go get another job"

10:40 Inspiration from the Millionaire Matchmaker show

12:55 Where Siobhan was finding clients

13:40 Leveraging comedy club guests

15:45 Expenses in running the business

16:25 Siobhan pays commissions (maybe a revenue source for you??)

17:36 Vetting clients

19:55 Where she looks for new clients and matches

21:49 Most Cupid in the City clients get matched within 6 introductions

23:12 Her fees are "mid-market" at 5,500 pounds to 10,000 pound sterling

24:15 Includes coaching to get client ready for dating

25:50 A day in the life of a matchmaker

28:13 Her biggest surprise!

30:28 Ten years to a 6-figure business

31:34 The most recent rewarding match. Wow!

36:32 As a matchmaker, you just can't take no

37:56 Siobhan's best tip for taking action

Closing Comments:

39:49 On being authentic

Connect with Siobhan:

• https://www.instagram.com/cupid_inthecity/
• https://www.cupidinthecity.com/

Connect with Joan:

• https://www.instagram.com/joanposivy/
• https://www.facebook.com/posivy/
• https://www.joanposivy.com/

Be on the show!

https://www.joanposivy.com/be-our-guest.html

Mike Montague got his first taste of working a side hustle at the age of 12, delivering flyers door to door. As he went through school, Mike got paid to build websites, perform as a DJ, and host an internet radio show.

Today his full time work is with an international sales training organization, and working remotely allows him time to grow his side hustle which this year is earning him about $50,000 through his company, Playful Humans. A good chunk of that revenue is by performing as a game show host.

Mike gets to meet people, play games and make money doing it. How cool is that?

In this episode, you'll hear about why his current employer got very interested in a book he wrote - it could be an a-ha moment for you, why multiple sources of income are a must, and other ways to get paid that could have a greater payoff than a one-time payment.

You'll also hear what Mike charges and how he prices his gigs.

And remember to stay tuned for the end of episode takeaway where I'll teach you a game I designed for my "Winning the Money Game" seminar. It'll get your creative juices flowing thinking about ways to double your money.

What You'll Hear:

03:42 Writing a book about LinkedIn led to more job opportunities at work

04:11 How Mike's hustles morphed into Playful Humans

05:41 First side hustle at age of 12

10:16 The gift of being trained in sales when you're young

10:47 Having to put down the wrong answers to pass the test

11:15 How Mike got to be a Game Show Host!

12:40 Being paid to play

15:34 Playful Humans podcast

17:33 Pre-show prep

18:30 What's YOUR answer to this "Survey Says" game question?

20:09 Jeopardy! a great way to review content

21:28 First podcast sponsor, an affiliate link

22:00 Revenue from affiliate links add up over the years

22:55 Don't have all revenue coming from one source

24:18 Pricing events with the "PIA Factor" LOL

25:55 What Mike charges for game show hosting

26:44 The value of getting in front of audiences, even if you're not being paid

28:23 Alternatives to getting paid money

30:12 Don't underestimate the value of practice

33:00 Getting fired live on stage in front of 5,000 people

36:08 The way to get good at sales calls…is to get through the bad ones

36:43 You have to be fully present for this work

37:40 Doing what you want to do vs. what you think other people want

38:40 The 2 really hard buttons to push: Record and Publish

39:12 Get into a positive spiral

Key Takeaways:

39:41 Paying with money is not the only way

40:00 How I got 2 kayaks for free

40:43 Doubling $1,000 in 90 days

41:52 Apply it in my "Winning the Money Game" seminar

42:35 What to do when you think, "I don't know" or "I can't"

Connect with Mike:

• https://playfulhumans.com/
• https://podcast.playfulhumans.com/
• Sandler Podcast, https://howtosucceed.libsyn.com/

Connect with Joan:

• Instagram

https://www.instagram.com/joanposivy/

• Facebook

https://www.facebook.com/posivy/

• Joan's Main Site

https://www.joanposivy.com/

• Email

Be on the show!

• Be Our Guest

https://www.joanposivy.com/be-our-guest.html

Imagine being a private investigator as a side hustle!

As owner of Pink Lady Investigations, Lisa Phillips has worked on infidelity and child custody cases, background checks, landlord and tenant disputes, and criminal defense cases.

She's built a solid reputation with attorneys as an ace process server because of her ability to get the job done.

In today's episode, you'll gain valuable insights into the world of private investigation.

You'll hear about what a day in the life of a PI is like, how much you can expect to earn, the differences in fees between investigative work and process serving, how to become a PI, and what makes for the best investigators. Plus, Lisa shares a creative and low-cost strategy she used to get her company's name on local TV, which could be useful for your side hustle too!

What You'll Hear:

02:19 Why Lisa ended up becoming a private investigator

03:30 Getting the attention of a local TV station

05:25 Local PI's object to Lisa's entry into the market

06:55 An alternative path to becoming a PI

09:10 Some webinar attendees became trainees

10:00 Dressing to get the job done

11:25 Some databases PI use can't be accessed by public

13:11 Be aware of the footprint you're leaving online

14:22 A day in the life of a PI

15:50 The "fake princess" investigation

17:24 Requirements to become a PI

19:26 Here's who makes the best PI's

21:40 Examples of typical clients

23:20 The final eviction (process) serve

24:43 What you can expect to earn as a PI

25:30 Flat rate for process serves, hourly for investigative

25:50 Lisa's rate is $95 and she pays contractors $40-$50/hour

27:00 Networking is huge in this industry

28:50 No, I won't give you your old sweetheart's contact info

30:48 Lisa's best tip to take action

31:44 Tell me I can't do something? Challenge accepted

Connect with Lisa:

pinkladyinvestigations.com

Connect with Joan:

• Instagram

https://www.instagram.com/joanposivy/

• Facebook

https://www.facebook.com/posivy/

• Joan's Main Site

https://www.joanposivy.com/

• Email

Be on the show!

• Be Our Guest

https://www.joanposivy.com/be-our-guest.html

Today we're seeing a much greater degree of diversity in Santas so it's opening the door to many who in the past wouldn't have considered it an option.

If you check out today's episode artwork, you'll see a photo of our guest Santa. Underneath that yak hair beard is Melissa Rickard. Yes, this Santa is female, but you'd never know it.

In addition to her full-time work as a surgical director for a retina practice, Melissa has been donning the red suit and sharing her ho ho ho's for 28 years!

In this episode of Side Hustle Hero, you'll hear about what income range you can expect - some of her friends make upwards of $40,000 a year as Santa - what you're looking at for start up costs, and where to turn for gigs.

Be sure to catch the end of episode takeaway where I'll give you a little nudge to get you thinking about why volunteering should be one aspect of your life, if it's not already.

What You'll Hear:

02:12 HOHOHO

04:00 28 years of being Santa

05:01 How Melissa came to be Santa…and why she continues

08:55 Number of gigs per year

09:28 "Live" emails 4 hours a night

10:15 President of local Lion's Club

10:33 Sources of work

11:45 Hourly rate

16:25 Hiresanta.com and Mitch Allen

14:48 Professional Santa groups and associations

18:05 Santa's start up costs

19:25 Earnings

20:31 Hasn't yet been busted by a kid

22:23 The power of touch

23:29 Yak hair beards

24:17 Why Melissa continues to be Santa year after year

27:04 Melissa's best tip for taking action

Takeaways:

28:50 Check out a Lion's club

30:00 The power of giving

30:16 Is Rotary for you?

31:05 The emotional compensation is off the charts

31:08 What organization would be the best fit for you?

Connect with Santa Melissa:

https://www.kringleandco.net/

Check out these international service organizations:

https://www.rotary.org/

https://www.lionsclubs.org/

Connect with Joan:

• Instagram

https://www.instagram.com/joanposivy/

• Facebook

https://www.facebook.com/posivy/

• Joan's Main Site

https://www.joanposivy.com/

• Email

Be on the show!

• Be Our Guest

https://www.joanposivy.com/be-our-guest.html

You can get paid for being a sports superfan? What???

Today's guest Patrick, a.k.a. Crazy P will tell you about that world. But it's clearly not the money that drives this passionate, positivity-exuding superfan.

On the surface, it looks like Crazy P's role is to energize fans at games. That's a big part of the job, but you'll discover that there's much more to it.

You'll also hear what's involved in being a sports superfan, what gameday looks like, and his other income sources that are offshoots of this side hustle that can serve as idea generators for you.

But above and beyond those things, he reminds us what's important in life. Spreading love and good vibes is what Patrick is all about.

What You'll Hear:

01:52 The role of a "Super Fan"

03:39 His relationship with the fans

06:35 The power of the chants

08:56 NHL Vancouver Canucks playoff moment

10:25 Inspiration from "Crazy George" & pitching the CFL's BC Lions

12:40 "Game day" routine

16:02 This is hard work!

17:22 Getting to work the Olympics

19:17 Learning chants from the Sweden and Finland teams

20:40 Working a BC Lions game and a Vancouver Canucks game AT THE SAME TIME!

23:41 What Superfans can earn

25:50 Get paid to create personalized videos for your fans…makes a great gift

28:42 It's about way more than the sport

29:21 The power of a personal moment

31:35 The "Crazy P Experience"

35:25 Brainstorming future game day experiences

38:02 High fiving the mirror for morning inspiration

38:50 Don't wait for the perfect time

40:11 Show your appreciation to the fans and players

40:24 A key to successful living

40:49 How you got to where you are at this moment in your life

41:00 The consequences of focusing on the negatives…and what to do instead

41:41 thewaysuccessworks.com

For a deeper dive into understanding what's showing up in your life:

https://courses.joanposivy.com/p/turn-your-thoughts-into-wanted-things

Connecting with Crazy P

• https://crazyp44.ca/
• https://www.instagram.com/crazyp44/
• https://memmo.me/ca/en/profile/crazy-p

Connect with Joan:

• Instagram

https://www.instagram.com/joanposivy/

• Facebook

https://www.facebook.com/posivy/

• Joan's Main Site

https://www.joanposivy.com/

Be on the show!

• Be Our Guest

https://www.joanposivy.com/be-our-guest.html

There's a good chance you have way more talent, skill, and experience than you give yourself credit for. To help draw those out, today's guest Sandra Booker has questions for you!

A plea from her 13-year-old daughter motivated Sandra to put her talent and skills to work to raise some needed cash. Her full-time job wasn't bringing in enough. So, Sandra embarked on an entrepreneurial journey by becoming a part time virtual assistant (VA). As that scaled, it was time to quit her 9-5 and make being a VA her full-time business. Realizing that a lot of the services she was providing were more big-picture and strategic in nature, Sandra shifted to being a Business Manager for multiple companies, and a trainer to aspiring VA's.

Regardless of your industry of focus, Sandra has tips, tricks, and inspirations to help you do what you do…better.

You'll hear several highly effective tips on finding clients, strategies for delegating like a pro (a must-have skill when scaling), and short cuts and hacks she teaches aspiring VA's that we can all use in our side hustles.

Be sure to catch the end of episode takeaway where I steer you in the direction of using some of the ideas you'll hear today, not only in your business life, but maybe surprisingly, your personal life too.

What You'll Hear:

02:54 The motivation to start a side hustle

07:52 Listing her gig in the wrong category worked out very well!

09:43 Think about what your client is looking for…and be there

11:42 Turning her gigs into a real business

12:37 from $25, to $45, to $50/hr for VA services

13:45 The decision to scale - a win/win with clients

14:45 Sandra's best delegation secrets

15:49 Take the time to hire, don't wait until the last minute

16:30 Check in with them to confirm your assumptions about their ability

18:15 Delegate the outcome or record your screen to share your process

19:50 Switching from VA to OBM

21:50 Working herself out of the job….is the goal!

22:38 Treat your client's business as your own - be in it with them

24:17 Difference between VA and OBM

25:40 What you can expect to earn as a VA

26:50 Where to look for clients - including co-working spaces

30:59 Where to start first if you want to be a VA (this applies to many side hustles!)

33:05 You likely have more transferable skills and talents than you realize

36:00 Don't inadvertently "assign a task" when you're pitching a client

38:17 Gain clarity on what is really stopping you - is it a real issue, or a fear?

40:01 Switch from "I can't" to "how I can"

Featured Takeaway:

41:45 Using the "recording your screen share" in your personal life

42:29 Let me know how you're applying this idea

Connect with Sandra:

• www.anyoldtask.ca
• https://www.instagram.com/anyoldtask/
• Sidekick COO Podcast https://anyoldtask.ca/podcast/

Connect with Joan:

• Instagram

https://www.instagram.com/joanposivy/

• Facebook

https://www.facebook.com/posivy/

• Joan's Main Site

https://www.joanposivy.com/

Be on the show!

• Be Our Guest

https://www.joanposivy.com/be-our-guest.html

It's Anna Cook's success with her travel blog, her love of travel and promoting local businesses that have positioned her so well for her latest venture - SimplyNCgoods, a subscription box service. In today's episode, you'll hear how the idea came to her, and the steps she took from the seed of an idea through to shipping that first box on launch day.

You'll also hear tips from this self-described "productivity hack nerd," and insights on how she's monetized her travel blog with 5 income streams.

She reveals her most unexpected surprise after the launch, what aspect of the box business she now needs to be laser focused on, and many invaluable resources she's found in her journey to launch day.

Be sure to catch the end of episode takeaway where I will suggest an often overlooked but invaluable source of ideas and insights to catapult your side hustle into greater profitability.

What You'll Hear:

03:08 Determining what is your most productive time of the day

04:50 Pomodoro method for getting important tasks done

06:25 Training your brain to know when it's time for "deep work"

07:38 Plan your side hustle work week!

08:21 Determining what "moving the needle" is for your business

10:10 How Anna started monetizing her travel blog (it's at $30,000 per year)

12:30 5 income streams from the travel blog, Stuck On The Go

14:04 Where she placed her focus to grow the income

14:21 Working with tourism boards - writing articles and selling photos

15:19 Writing SEO articles

15:43 Integrating product sales

17:16 The most lucrative 2 sources of income from the travel blog

18:06 Reason for avoiding selling her photos through stock photo platforms

19:09 The idea and motivation for the subscription box business

20:46 Consider paying local merchants with cash

22:40 The journey from idea to shipping the first box

23:20 Choosing and learning from a marketplace/platform specifically for subscription box entrepreneur

26:22 Partnering with another business to grow the email list

27:20 Using software that'll choose the cheapest shipping options each time

29:33 Anna discovers she priced the boxes too low!

31:06 Creative additions for the boxes

31:26 Working on adding value without increasing costs

33:35 SimplyNCgoods

34:35 Creating added value for the subscription box businesses

36:20 Biggest surprise after launch

39:25 Progress over perfection!

39:40 Reverse engineer your goals for the fastest progress

Takeaways:

41:00 Someone likely has your solution

41:37 Reach out to someone in your industry

42:17 Be open to looking for answers outside of your industry too!

42:53 A four-letter word to use when you get a "no."

Reach out to Anna:

• https://www.stuckonthego.com/
• https://simplyncgoods.cratejoy.com/
• https://www.instagram.com/stuckonthego/

Connect with Joan:

• Instagram

https://www.instagram.com/joanposivy/

• Facebook

https://www.facebook.com/posivy/

• Joan's Main Site

https://www.joanposivy.com/

Be on the show!

• Be Our Guest

https://www.joanposivy.com/be-our-guest.html

Today's guest has proven her ability to start and grow 2 side hustles while holding down a very full time corporate job. Eventually she sold one of her businesses, but being the adventurous entrepreneur and top-notch marketer, she then started looking for yet another income source and instead of starting another, Krystal Covington decided to buy an already established online business…one that she could grow by applying her areas of expertise.

Have you ever thought about buying an existing business, rather than starting from scratch?

It's an interesting idea and one that I'll explore in today's end of episode takeaway.

But before that, you'll discover a lot of tips and ideas to apply to your side hustle because we'll hear how Krystal landed in a new city and launched and grew what would become a 6-figure business known as the Women of Denver, why she lost a lot of money in her lace front wigs venture, what's caused her marketing agency to flourish, and a lot of words of wisdom sprinkled throughout this episode.

What You'll Hear:

02:38 Two side hustles and a full-time job

04:05 Charging "time and a half" for the first gigs

04:25 A women's group born out of necessity

05:30 Interviews, events, a blog, meetings, and networking morphed into Women of Denver

08:25 Her bedroom becomes a recording studio

09:02 Outgrowing the coffee shop as a meeting place

11:24 Two memberships tiers $35/$150 month

15:50 Time to leave the full-time job

18:56 The 4 keys to influence - people want to give you money

20:16 In the first year building the women's group, posted on FB every day

22:40 Using links to increase your SEO

25:00 Should you niche? Maybe not.

27:20 Where to post

28:04 Commenting on others social media posts is what's working for her

29:35 Posting on it's own is a lot less effective today

30:00 What to be aware of when posting on TikTok

31:17 Searching for a profitable business

34:50 Where Krystal discovered businesses for sale

36:15 A business loss that really scared her

39:03 Sources of free coaching and business guidance

40:50 The "automation" of her skin care business

43:19 Listen to people who have done it!

Takeaways:

44:08 Thinking about buying a business? Do your due diligence!

44:50 Maybe someone wants to "pass the reins" to you

45:32 Why I knowingly paid $100,000 more for a business than it was worth at the time

46:18 Why the business Krystal bought is a great fit for her

46:35 Did I mention the need for due diligence?

How to find Krystal:

https://www.krystalcovington.com/

https://www.instagram.com/krystalgolead/

Connect with Joan:

• Instagram

https://www.instagram.com/joanposivy/

• Facebook

https://www.facebook.com/posivy/

• Joan's Main Site

https://www.joanposivy.com/

Be on the show!

• Be Our Guest

https://www.joanposivy.com/be-our-guest.html