Side Hustle Hero

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

Have you ever thought about being SANTA as a seasonal side hustle? 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

Today's guest could not envision herself continuing to live and work full-time in Belgium. Instead, she's crafted a life in Cusco, Peru involving no less than 6 part-time hustles. The most lucrative one for Maya Lombarts is her role as a virtual assistant (VA). It's her #1 because in addition to excelling at it, she doubled down on an often overlooked, but potential goldmine of a source for clients. In this episode, Maya shares tips and tricks for challenging your assumptions of what you can and should charge clients, who to ask for advice, how to explore the potential business opportunities in your areas of passion, and of course, ways to get paid more as a VA. She might even inspire you to ask yourself, are you living exactly where you want to live? Be sure to catch the end of episode takeaways where I'll challenge you about the choices you've been making, how I became aware of unconscious, false beliefs guiding my decision-making, and how we can become open to expanded possibilities that lead to wiser choices. What You'll Hear: 02:48 No full-time job: A lifestyle choice? 06:40 From "I can't," to "how can I make this work" 06:50 "What if there is a way?" 07:15 Six distinct side hustles, including professional singer 09:33 Online memberships as an income source 11:27 Embracing diverse roles 11:55 Selling tours as a hustle and leveraging Couchsurfing 14:27 Most lucrative of the 6 hustles: VA 17:12 Typical hourly rates for a VA 18:35 Opting to get direct VA customers, less reliance on VA platforms 19:35 Strategy when marketing through the platforms 25:15 Maya's typical weekly "schedule" 28:15 A Peruvian perspective on committing to future social engagements 28:47 A mix of the cultures is best 29:35 Our way is just one way…not necessarily the only way or the best way 30:29 Cusco, Peru - altitude is 3,400 metres (11,155 feet) 34:01 Uncovering business opportunities in your areas of passion 40:33 How a recommendation can garner you better rates 40:46 Strategies for getting paid more as a VA 43:45 Maya's best tip for taking action Takeaways: 44:58 Shift from "I can't" to "How I Can!" 45:45 Uncovering a negative belief that was guiding decision-making 47:47 Doing things habitually "because that's just what we do" 49:11 Have a productive brainstorming session this week to pull back the "horse blinkers" Connect With Maya: https://mayalombarts.com/ https://www.instagram.com/mayalombarts/ 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