My Journey Into Airbnb (Hosting, Co-hosting, Investing and Teaching!)

(00:00) I’ve been hosting on Airbnb or co-hosting or investing for the better part of a decade now I got started when I had absolutely no money in fact when I first got started I was in pretty crushing debt and now I built up to a portfolio of properties I own that generate consistent cash flow so that I never really need to work a consistent day job ever again in this video I’m going to share with you my entire journey start to finish exactly what strategies I used how I got here um and what I recommend for new people starting
(00:29) out so that you can learn from my process you can learn from my experience and if you’re interested in learning about in Greater detail any of these different strategies that I’ve learned and deployed throughout the years then I highly recommend you check out the links in the description down below most specifically B&B tribe it’s a really really great entry point it’s a community that we just launched not too long ago that is specifically for anyone a co-host a host an investor a vacation
(00:56) home owner uh or anyone that’s aspiring wanting to get started if you want to join a community of other like-minded folks who are successful and getting started and learning about Airbnb and short-term rentals and you want to get access to some incredible training that quite frankly other people out here charge lots more money than what we’re charging for in here and you want to get access to all kinds of different deals and perks and discounts expert interviews Community calls everything then check out B&B tribe it is really
(01:24) really affordable we try to make it as accessible as possible so that we could guarantee the highest amount of value possible for everyone inside so if you want to check that out we’ve also got additional trainings that are linked in the description down below that go into detail about some of the different strategies that I’ve used so you can check those out as well but let’s go ahead and dive right into it oh actually before I get started give this video a thumbs up if at any point you find it
(01:46) very valuable to you because it really does help me out with growing the channel I’ll start at the very beginning when I first got started with Airbnb it was right after a failed business venture shirt that left me about $30,000 in debt now I’ll touch on that briefly here it was basically a business where I was having watches manufactured and I was trying to then resell them basically drop ship them uh it’s not it was Drop Shipping wasn’t as popular back then so I didn’t really call it that but that’s
(02:16) essentially what I was doing and long story short I had no idea what I was doing made a whole bunch of mistakes and ended up in a lot of debt now at that point I kind of had a decision to make did I want to go and get some 9 to5 and start slowly chipping away at this debt or did I want to try my hand at starting a business again but if I Tried to start a business again it would have to be business that I could start without any money so that was a bit of a tall order because most businesses tend to take a little bit of money to get started and
(02:45) so I was left with this kind of conundrum but I was young and quite frankly I was a little bit foolish back then and so I really really wanted to be an entrepreneur I really wanted to run my own business and do my own thing and have all the freedom and lifestyle that was associated with that now I will will warrant that doesn’t necessarily play out exactly like that especially in the early days now I’m fortunate enough that I am in a place where I have a lot more freedom and lifestyle and financial Independence but back then starting a
(03:11) business was definitely not for the faint of heart when you’re first getting started so I decided that I was going to do it and I actually had a friend of mine who was working with another company over in Asia and they were basically helping investors from Asia to purchase properties over in North America and then capitalize on those as well as they could and so as part of that they were actually helping them to connect those Property Owners with short-term rental property managers so my buddy Sam was his name uh he
(03:38) basically was reaching out to these different property management companies he got talking to them and he started realizing well heck there’s some people that are not you know any smarter than us and they’re making really good money doing this they’re basically just hosting other people’s properties doing something called co-hosting or property management and they’re doing an exchange for a percentage of the overall Revenue so he thought well this is a business that we could start up so hey James why
(03:59) don’t you go back to Canada I was traveling around the country around the world I was actually over in Asia at the time and so he said why don’t you go back to Canada over the Christmas break see if you can get some Property Owners signed on board if not all good go back to your traveling go back to your backpacking that time I was backpacking to just kind of run away from all my financial problems not really something I would recommend to most people um but he said hey if you succeed great we can start this business up if it gets
(04:25) successful enough I’ll actually come back over to North America from where I am over in Asia and we can grow this business together and if it doesn’t if it falls flat on its face if you’re not able to get any properties then hey all good we’ll just you know call it a loss and you can go back to your traveling so I thought well heck I’m already going back home for the holidays anyway why don’t I go and try my luck and what we decided to do at that point was we decided to basically uh just start
(04:51) pitching people on co-hosting and we also were going to combine in a bit of a little bit of rental Arbitrage so that came a little bit later so initially I started pitching people on this model of co-hosting of hey I will you know manage your property for you and in exchange for a percentage of the revenue and the very first client that I ever got signed on board with us was actually a connection that I had someone in my network and he basically his situation was that he had a condo right in downtown Toronto that he would come to
(05:20) during the week but on weekends he went out to his actual property his actual home uh north of the city and so on the weekends this property would sit vacant and he thought well heck if you guys can rent it for me on the weekends I’m happy to give you a percentage of the of the revenue and you can just take care of for me and hopefully it’ll pay off a lot of the the rent cost associated with having that property and so we were actually able to do that it rented out really really well and it was able to
(05:43) completely offset and cover his cost and we made some really great money doing that now on that time time Horizon there as well I also went and I actually in that time back I really hit the ground running reached out to probably 50 60 70 different Property Owners through whether it was Kijiji or direct through Airbnb back in the day or all these different things I tried everything and really really gave it a go I managed to line up meetings with I think about five or six or seven property owners and I managed to sign I think it was like four
(06:11) or five or six of them on under management so it actually went really really well um and the cool thing was I did it Without Really any track record any experience anything to show for it I just really understood what their challenges are what their pain points were and offered a really good solution and built a lot of trust with those Property Owners I was very transparent about the fact that I was just starting this up and that I was going to be a new business and you know they would just really need to trust me that I was going
(06:36) to do a great job now looking back I’m very very grateful that those Property Owners did trust me but I’m not sure that I would do the same if I were in their situation so it’s definitely better if you’re just getting started to learn and develop and now there’s so much knowledge out there that there just didn’t exist 10 years ago about how to do all this stuff how to be more efficient with it uh but obviously I’m very grateful that I was able to get started the way that I was now so that
(07:01) basically got me started into co-hosting but then because now I was running this business I said okay well it went well enough that I’ve got to stay here I’m not going to go back to my traveling around this is an actual legitimate business that’s going to be making us cash flow it’s going to help me to get out of debt going to be able to grow it said well I need to find a place in Toronto to live and if anyone knows anything about Toronto it’s not an overly inexpensive place to live it’s
(07:24) not very affordable right it’s pretty expensive and I again at that time this was really really early on right I hadn’t even been managing these properties yet I just got them signed on they weren’t launched and ready and going and so I still had all this debt so I thought okay how can I do this well naturally rental Arbitrage kind of house hacking type of strategy came to my mind I thought well hey I can go and rent a place that’s two or three bedrooms it’s really great because then when Sam moves
(07:50) back he can just move into the spare bedroom and in the meantime I’ll just rent the other bedrooms out on Airbnb and at the time again I don’t really recommend this I actually also in the living room put a pullout couch and just had a pullout couch listed on Airbnb as well as the other two bedrooms and then I slept in the one bedroom now that wasn’t ideal because it kind of turned the place into a hostel where new people that were checking in on Airbnb would go into the bedroom and they’ be like well
(08:17) who’s this random person sleeping on the couch in the living room so that wasn’t that great but it was back when you could kind of get away with that stuff on Airbnb and I charged less than what the hostiles were charging so it’s like the cheapest place to stay in town and I managed to make up it we were just so consistently booked that all three of those places running full capacity I fully covered all of my rent expense and then some I was actually able to pay for all my groceries as well with the money
(08:43) that came in from that so that was really really nice it allowed me to have a place in the city to stay so I could conveniently get to all my meetings with clients and everything else like that without having to pay an arm and a leg for rent so that was really cool and then Sam later on did actually come back to Toronto and help me grow the business and he just moved right in there we actually ended up with that landlord we picked up another property that he let us do uh co-hosting with and then that’s probably right around the time that we
(09:09) found some property owners that weren’t super open to the idea of co-hosting because they had other investors that they had purchased the property with and they really needed a solid like consistent monthly income in order to go and show the investors that they you know were deserving of their confidence so they said well no we we won’t do co-hosting with you but if you want to rent the properties from us and then flip them on to Airbnb you’re welcome to do that this is our first time trying this strategy out we decided to do that
(09:36) and it actually ended up working out really really well now again I don’t recommend this strategy because we actually looking back got very very lucky with that deal this is a property that we expected would bring in3 or $4,000 a month and so we ended up paying I think it was like 28 or $3,000 a month in rent and so it really wasn’t going to pencil out to be that good but lo and behold just because of the uniqueness of that property and where it was located it was a combination of things that we didn’t really think about early on that
(10:06) just ended up working out in our favor we ended up averaging I think about6 or $7,000 a month with that property so it was a total Cash Cow for us and we started doing that we went okay great let’s just keep doing this it’s making us so much money doing this and we went and we picked up more properties using rental Arbitrage but then obviously not all of them went that well now it’s not that they lost money we actually were fortunate enough that they all made money but the problem was now we were
(10:31) spending all of our cash to get that next property to rent it to furnish it pay the security deposit all that stuff and it was a lot more volatile there’s a lot more up and down there was a risk of losing money and we knew that if the landlord told us that we they wouldn’t renew our lease or didn’t want us to keep renting the property or if the city passed any regulation anything like that then suddenly we would be kind of high and dry we’d be at a loss because now we’d been investing all this cash to
(10:58) grow the business but we wouldn’t having to show for it if things took a turn for the worst or if it didn’t get booked things like that so based on that we decided to stop growing the rental Arbitrage side unless we found like real unicorn properties that were an absolute knock out of the park and we only ever ended up finding one more of those that went really really really well uh because they are few and far in between and hard to find we focused fully on the co-hosting model we just grew the co-hosting model actually grew it to the
(11:27) point where we had at the at the peak of it about 35 properties that we were managing it was doing really well the business was Cash flowing really well um and then we were still doing like this kind of rent hacking thing where we had people staying with us sleeping on our couches I actually met a really really close now kind of like longtime friend through doing that so that was really cool but it got to be a lot it was a lot of work and at that time actually that same friend I just mentioned he stayed on one of our couches um and he was
(11:53) actually one of the guys sleeping on the couch when we were like just you know just renting out the cheapest place to stay and he he opened my eyes to this idea of the whole like online education space I had never really been exposed to online business or online education but he was from New Zealand and he told me about this guy named Sam who had this like training program to teach people how to run online Consulting businesses and so I thought okay well then I can I can probably have some knowledge here that I’ve gained through
(12:20) doing all of this and my very first foray into it was I decided to launch this course called how to live rent free and the goal was that I was going to teach people how to live rent free doing the same kind of kind of house hacking that I had done that completely flopped no one really cared enough to buy that and the people that wanted to live rent free those were people that didn’t really have money to pay for coaching things like that so that didn’t work out and then I decided that I was going to try to teach property management
(12:46) companies how to install the right systems into their business to be able to grow and run operations well because that’s there’s a fair bit to it um and I also you know had learned quite a bit I came from a bit from a business background of studying and actually running a kind of franchise style business it was highly systemized so we had actually done a pretty good job of setting up all the business systems and so I started just dialing out to property management companies cold calling and no one really wanted to
(13:12) invest the money into working with me until I spoke with this are you a brand new or experienced Airbnb host co-host or investor who wants to host as successfully as profitably and with as much fun as possible if so then I would love to invite you to check out BNB tribe Linked In the description down below this video it’s our exclusive Community for Airbnb hosts investors and co-hosts from all over the world where I share some of my best trainings that go into detail on every single aspect of Airbnb hosting from A to Z we’ve got
(13:47) Advanced Training playbooks that will help you to use more advanced strategies to take things to the next level and make more money and have more fun hosting co-hosting or investing on Airbnb you’re also going to get access to an incredible community and over $2500 worth of deals perks discounts bonuses that I’ve negotiated with other vendors in the short-term rental industry so if you want access to all of that and a whole bunch more check out the link in the description down below for B&B tribe and I would love to see
(14:16) you on the inside uh this lady named Alicia and Alicia was actually my very first ever actual coaching client for property management and she ended up being a nurse she wasn’t even running a property management company she was just a nurse nurse that really wanted to run a property management company so that she could have more flexible hours more time to spend with her family and really just have more financial and and kind of location and time Independence and freedom and so that was this kind of light bulb aha moment for me where I
(14:43) didn’t need to go and work with established companies and help them to systemize and things like that I could help people that were wanting to get started with this business at the time I thought well heck there’s probably only a handful of people that would even be interested in this kind of thing but lo and behold it was actually something that people were really really interested in and we got really great results with clients too like Alicia within I think about 6 or eight weeks of working with me had her first few
(15:05) clients on under management and to this day to my knowledge she’s still running that same business over in uh in British Columbia and doing really well she’s still active member in our community she’s still chiming in she’s still running that business really effectively so that was really really cool and that was kind of a light bulb moment for me from there things sort of started to snowball where now suddenly I you know had this property management company I had this education company and I wanted
(15:30) to put more time into the education company because coaching has always kind of been this passion of mine we started to get a lot of traction there and I just enjoy it a lot when the property management business was kind of up and running and relatively systemized we didn’t want to grow it too much further uh because always the goal to make it more of a lifestyle business I just got a little bit bored of it I I really enjoyed the challenge of starting a new business and I still do to this day it’s why I love coaching it’s why I love
(15:55) mentoring people is because I love all the challenges that come along with doing something of brand new for the first time and so I get to kind of constantly relive that experience by coaching people like yourselves and so I wanted to do that so I decided to sell my share in the property management company to another person who ended up then partnering with Sam and continued to run the company and then I focused more so on the education side of things and my first kind of big real blast off with the education side of things was
(16:21) when I got involved with a Blog called learn BNB and the the then owner of the blog Simon who is now a business partner of mine uh really great guy he had this blog all about Airbnb and hosting and when we promoted my educational training programs to that company to their kind of email list or subscriber base Their audience it ended up doing really really well so that’s why I decided to purchase a portion of that business and I got into that into the online education space even deeper we launched another
(16:49) program after that teaching just hosts that wanted to host their own place How To Succeed really well and then did that for a few years and that went really well and really really enjoyed it and all that still running to this day and that’s what then got me into investing for a while I had seen this opportunity to just buy the properties right just and seemed like a pretty natural Next Step but I didn’t really know how to actually get started I didn’t have the expertise and the experience of how to
(17:13) buy real estate it was a little bit of a daunting task to me I didn’t know the whole process anything like that so I learned that process and was able to get started actually investing in a property and so I went into that first deal with an investing partner that went quite well the property did really well it was cool because I knew what to look for and what to avoid with a short-term rental property and so that went really really well and then naturally I started just kind of adding that to my portfolio of
(17:37) things I could teach people because once I had done it once I had learned the ins and outs I went with this investing partner and we launched a coaching program teaching people how to invest in short-term rental properties and then I started taking over more of that on my own and took over the coaching side of it more just myself so now I just run that coaching program I bought another property for myself and kind of continued to expand my own investing and grow the portfolio that way and that kind of brought me to relatively
(18:01) recently so as of recently in the last little while here we launched something brand new that I’m actually really really excited about it’s called B&B tribe because up until that point everything that I had done had been kind of siloed right we worked with host and we work with co-host property managers and we worked with investors but they were all separate they were all kind of siloed off into their own different things and I thought to myself well hey there’s a whole bunch of value in putting a community together that’s just
(18:28) everyone it’s the co-host it’s the host it’s the investors it’s the vacation home owners and we can all learn together and I wanted to put together some kind of basic boot camp training so we developed this program called B&B boot camp that’s a part of B&B tribe everyone that joins gets access to it and just goes through kind of Airbnb crash course 101 everything you need to know to succeed it talks about how to acquire properties through investing how to acquire properties through co-hosting
(18:51) how to acquire Properties by converting existing space or existing properties you already have how to set them up how to launch them how to price them how to be profitable to manage everything all the ins and outs but then the other cool thing is that as I got more into this space over the years I started to realize there’s so many different elements to it there’s tax benefits that you can leverage there’s legal structuring you want to be aware of there’s AI that you can use now for things like guest communication or
(19:16) increasing your returns making more money there’s other strategies like direct bookings that you can leverage you can do email marketing to get leads um there’s all kinds of different strategies you can deploy to you know basically just do a better job of Hosting make more money make it more profitable make it a lot more fun make it a lot easier more hands-off and so we put together these things called Advanced Training playbooks that would teach people all the ins and outs of all that kind of stuff as well and then the
(19:39) really cool thing that I’m most excited about is this community of hosts and co-hosts and investors and vacation home owners all working together and learning from one another so that for me is personally one of the most exciting uh components of all of this is that we can all work together all collaborate all learn from one another all get to hang out together and just really build a community of people that are kind of unified by being in this short-term rental space and also being interested in and kind of excited about lifestyle
(20:08) Independence lifestyle Freedom what’s really cool for me is that now with the educational company and the the the properties I own I can travel like I didn’t have to experience winter in Canada this year I was able to go down to Texas and spend some time down there I’m able to travel to Asia to Europe and just kind of really be where I want I can be fully location independent which for me is really really awesome to be able to live life that way especially while I’m young uh when I get to spend
(20:33) time with family with friends and really have a really nice lifestyle that actually isn’t just me working all the time I get to enjoy it so that’s really fun for me and I like being part of a community and building a community of people that are similar minded along that same vein uh and also I I really do believe in building long-term wealth building Financial Freedom because that is such an important piece of all this so being a part of a community that’s really interested in that and has crossed over in loving Airbnb and
(20:59) shorter rentals it’s just been really really cool for me so all that stuff by the way is linked down in the description down below but that’s really been my journey so far nowadays I have my own properties that I own um and I’ve got all the educational side of things I’ve also written the book air beam be for dummies I forgot to mention that that was kind of a along that that path of getting in uh and working with Simon with learn BNB and it’s been really really cool I’ve learned so much over
(21:22) the last decade about business about life about lifestyle about finances about short-term is about you know everything um and it’s just been really really cool to be able to share that with all you guys here whether it’s on the YouTube channel or whether you are in BMB tribe or whether you’ve worked with me in coaching we’ve worked with over a thousand different students all over the world now just been a really really incredible experience I’m very grateful to have the opportunity to do
(21:45) this so I hope that’s been a interesting to you maybe you don’t even care about any of this uh but I’m sure if you’re at this point in the video then you probably are interested to some level uh about the kind of Journey that I’ve been on so far so hopefully that was interesting for you hopefully it sparked something for you uh and as always if you have any questions comments thoughts anything you want to know more about just let me know in the comment section down below if you did like this video
(22:07) give it a thumbs up just hit the like button it really helps me uh with growing this Channel and getting these videos in front more people and helping out more people like your awesome selves right here uh if you want to stay up to date with this channel WE Post two new videos every single week so just hit the Subscribe button there you can turn on the notifications as well if you want to be alerted when we post new videos so you can be the first ones to check those out um all that being said I hope you enjoyed this video and I’ll see you over
(22:29) in the next [Music] [Music] [Music] one