The Road To Becoming The 'All-In Solopreneur'

Imagine a world where you're the master of your own destiny, no bosses, no board meetings, just you and your entrepreneurial spirit. Welcome to the world of solopreneurship, a journey I, Chris Hanna, have embraced wholeheartedly and today, I'm sharing the highs, the lows, and the vital lessons I've picked up along the way. Starting from my humble beginnings flipping hockey cards as a kid, to creating a unique side hustle in high school, and even using poker to supplement my income - this episode is packed with anecdotes and insights that have shaped my journey.

Taking the leap from being a VP of Operations at a startup to becoming a full-time solopreneur is no small feat. It's a journey that's been laced with challenges, but also brimming with invaluable lessons. From my experiences in real estate and poker, to hiring over 500 individuals across different industries, every step has been instrumental in molding me into the solopreneur I am today. Expect to hear about the strategies that helped me navigate through rough waters and the reasons why I choose to focus on multiple business offerings instead of just one.

Lastly, I pull back the curtain on my All In Deep service, a cornucopia of business offerings designed to help fellow entrepreneurs achieve their goals. From a unique video batch creation process that allows me to churn out 40-50 videos in a day, to a tailored offering through another company, Hire4Me, aimed at helping business owners scale their operations, I've got a lot to share. So, if you're curious about my journey, eager to pick up some tips, or want to find out more about the services I offer, pull up a seat and tune in. This is one journey you won't want to miss!

For more information about Chris Hanna, visit https://chrishanna.ca

If you want to batch-record video content and have our team schedule them on social media, remember that one day of working with us will set you up for months of consistent content. Visit https://allincontent.ca today to get started. Let's go all in together.

Transcript

Speaker 1: 0:01

Welcome to the Chris Hannah Show, where the show we're talking about how to live life on your terms, how to bet on yourself and ultimately go all in. I am your host, chris Hannah, alright, so, as many of you know who listen to this show or follow me on social media, I call myself the all-in solopreneur, and some people out there might be wondering what the hell does that mean? What is it all about? And that's exactly what I'm covering in today's episode of the Chris Hannah Show. I'm talking about my journey of becoming the all-in solopreneur, my story, my motivations, the challenges that I faced, how I've either overcame them or I'm still working through them, some of the tips and tricks that I basically have on this whole journey that I've kind of gone through, and maybe that can help other aspiring solopreneurs who are out there who are maybe listening to this podcast as well. So again, welcome to the Chris Hannah Show and let's dive in and I'll share some of my story on this crazy journey.

Speaker 1: 1:01

So I have been somebody who has been entrepreneurial my entire life. It started when I was a kid. I would flip hockey cards or pogs, if you remember those, or I'd go to garage sales and see something and then try and resell it at our own garage sale or man the garage sale all day long. I was always somebody who was hustling and trying to make money. I didn't come from a family that had a lot of money, and I knew early on that I had to work and get a job if I wanted to buy anything, if I wanted to get new stuff, I had to do it on myself in a lot of ways, and so that's what I did early on as a kid, and then, when I moved into high school, one of the things that I created as a bit of a side hustle for a little bit is I recorded cassette tapes where I would summarize the core messages and themes of a textbook especially geography was the one that I started this on and I would sell it to the students who weren't really doing as well. 20 bucks a tape, and they'd get to listen to both sides of the tape and ultimately learn the key aspects of what was going to be covered throughout maybe tests or exams, or throughout the course of the year, because I'd summarize it all for them. I learned a lot during the process, and then my goal with them is that they could then go to sleep, listen to it and subliminally learn. I'm not saying I'm a con artist in any way, but the students that I did work with ended up having higher grades than what they were traditionally used to because I had studied so much. That obviously benefited me in some respects as well, and I got 99% that year in geography because it just absolutely just worked out really, really well. But I was always entrepreneurial.

Speaker 1: 2:47

And then I get into university and I kind of stopped. I started focusing on just trying to do the school thing, and it wasn't until I learned how to play poker that I realized is that you can create additional income streams again, and gambling became that additional income stream and it became such a thing that has been a big part of my life now for the last 20 plus years, or whatever it's been that I find that gambling, and playing poker in particular, has been a way for me to supplement my income, and so there's a little bit of where, like the word all in, started entering into my world and then, over the course of the last 20 years, I, of course, I get a job in the car rental business, and some of you might have heard this story before and I'm crushing it in the car rental business. Four and a half years in, next thing, you know, I become branch manager of the year in southwestern Ontario and then two weeks later I'm fired. Taught me a lesson that there's no such thing as loyalty and that you can definitely, you know, be on top of the mountain one day and at the bottom the next. And I wasn't prepared for it, but it made me realize is that you have to protect yourself. And I wasn't in a position financially that I could really afford to have been fired. But it happened and it took me a long time to rebuild and reinvent myself.

Speaker 1: 4:19

And I started at the bottom of a company and I worked my way back up afterwards and as I built myself back up, I started to realize I'm like you know what, as much as I'm doing really well, I got to find a way to make some additional income. I got back into poker after having taken a break for a number of years. I started making a few thousand dollars extra a month doing it and that was really good. But I wanted something more, because it can't just be about gambling. But again, it was a big part of who I was and I started to remind myself that you know what, the best investment I could ever make is the one in myself. So I'm working away manager level, you know, in a company and I'm doing well from the job perspective, but I'm not happy and I'm not fulfilled. But that again, that investment, that ROI that you can get by really investing in yourself, can be huge. So I start to attend more events and conferences and I start to network with different people at these conferences, while still kind of related somewhat to the industry that I had been working in.

Speaker 1: 5:26

But my whole purpose of going to these events was to gather information, to the gather Intel, to understand ways to become better myself. And I would go to these events and I would see people up on stage, or I'd see them in a workshop in one of the side rooms and they would, you know, be doing their thing, and I'd say I think I could do that, I'd love to speak. When I was a kid, I used to be a public speaker and I used to be on stage all the time, or the kid who was the lead in all the plays in school. So I'm like I really would love to do that, like, if I get an opportunity to present. That be amazing. So I would go to these events with the goal of understanding how they're doing it, and I realized that almost every single person who is speaking at one of these events is considered an entrepreneur. They are somebody who gained experience somewhere and at some point they bet on themselves. They went all in and now one of their income streams is speaking no-transcript, and sometimes they do events where you're not getting paid but you're getting leads that come from it, or their whole thing is that they are just professional speakers. So I would get to go when I meet these people, I'd talk with these people, I'd understand what they're all about, and that got me really Excited and passionate about the idea of trying to chase and pursue this idea of speaking. So I'm in the corporate world and I'm going through this process of Attending conferences every few months as much as they possibly can, going to workshops, connecting with people, talking to them on LinkedIn.

Speaker 1: 7:05

I start to realize, well, if I want to do this, at some point I need to start to build my own personal brand, and that's when I started posting content. First, I built a website, though right, I built a website called that evolving management calm. It was gonna be focused on leadership coaching because, well, I'd been a leader for at that point, like 15 years or whatever it's been, across a variety of industries. I think I could do leadership coaching. So I'll just call myself a leadership coach. I'll have the website and Customers will come in. Well, of course, they don't come in. They don't come in because, well, you can't just build a website and think traffic's instantly gonna land on your site. It takes time. So, start building blog posts and I start doing some of these things are like little social media clips and posts and stuff like that, and I'm still getting working full-time but I'm trying to just promote evolving management, calm.

Speaker 1: 7:55

And Next thing, you know, okay, somebody sees some content and asks me am I interested in being a Speaker or a featured contributor at the time? And and I say yeah, absolutely. And pretending having that imposter syndrome but having that pretend kind of confidence that I can do this. And in next thing, you know, I start doing some side gigs and I start hosting webinars and I start being featured and I get on some lists of people to follow and, before you know it, I'm really starting to feel like this is becoming a reality. I'm starting to become the person that I ultimately wanted to be. So I start chasing and the thing I start chasing the most was speaking gigs started applying to speaking gigs.

Speaker 1: 8:40

So this is late 2019. I started again making some extra money beyond the corporate world as Some coat, as a leadership coach, doing some stuff on the side as a career coach or kind of a career transition thing, building out some freelance content and Be having a speaker, picking up little gigs here and there. So I start figuring out 2020 is gonna be my year. 2020 is going to be the year where I'm gonna have a lot of speaking gigs and really be able to do this and truly Bet on myself because I've learned a lot. But now I'm ready. So I book five, six speaking gigs throughout the year. I think I'm ready to go.

Speaker 1: 9:20

January comes. The first event was supposed to be was April yeah, april of that year. And what happens? While the world shuts down, covid hits, all my speaking gigs gone. It was supposed to be the biggest year of my life. I thought at that point and and Covid hits, and it's instantly gone. Of course, the world's scary at that time, new information coming out every single day. I'm thinking that the world's coming to an end in some respects. So the safe play Is you just keep my head down, stop doing any of the side stuff. I didn't do a single side related gig For then, I would say, 10 months in 2020 and I just focused on work.

Speaker 1: 10:09

But I was still Unfulfilled, looking for something more. Well, what happens again? Get fired, lose my job. But this time around I wasn't as upset as I had previously been when it happened. This time around I was more relieved because I realized the safety net of another job was holding me back from truly going all in and Pursuing what I wanted. So who's my job Next day? Instantly start creating lots of content, because I really learned at this point how to batch, create content and Start putting myself out there. And I Instantly start getting some clients from a career coaching perspective, helping people navigate job loss, and I started picking up some some luck in little work, but nothing that's like really crazy. That's paying the bills. But I'm feeling really happy in the latter half of 2020 because I'm Doing things on my terms.

Speaker 1: 11:12

But then an opportunity kind of came about and the reason for this is like I had jumped on to LinkedIn and I thought, well, I'm not consistently pulling in the income that I need to pay for everything that I want to pay for and to live the life that I want to live. Let me just take a quick idea out here and let's just see you know what I can find on LinkedIn. So LinkedIn had a thing where they were doing a promo sale, saying, hey, you get the premium membership for a discounted rate or a free trial or whatever it was. So I signed up for that free trial and I go into the job section and it tells me that you can get a great match with a particular company. It was called Cash Flow Tribe and it was for their VP of operations role. I thought, oh, this is kind of interesting. I'm like a 98% match, according to LinkedIn, with this particular role. I've never been a VP before. The highest level I've ever been was manager. I tried to get the directory for it but I just never broke through that. I'm like I'm not qualified for a VP position. No chance in hell. The thing that was interesting is that it really read as an entrepreneurial type of company and, even though I thought maybe the company was not a real thing, I didn't think that a company called Cash Flow Tribe was real. I said this could be interesting.

Speaker 1: 12:37

But then at the bottom it said we ask you to submit a video. Submit a video explaining why you think you're a good fit and why you're interested in this position. I thought what's the worst that can happen? I will put together a video, I will submit it and they could like me. They could not like me, but at least I tried and put myself out there. And again, I'm not really looking for a full-time job, but I realize I probably need money to come in. So I thought we'll see how this goes, and so I put my video together. I start putting a little bit of basic graphics and animation. It was like I look back at it now because I still have a copy of the video that I submitted.

Speaker 1: 13:17

Like I don't know how this happened, but they ended up calling me and wanting to have an interview with me because the video itself, like it, was poorly lit. It just was not the level of quality that I've learned how to do now. But I put together this video and I go through the interview process and I start to realize I'm like, huh, I might have a legit shot at this. Like it's crazy to think, but I think I could have a legit shot, even though it's in an industry that I have zero experience in at this point it was real estate education. I might have a chance. So I go through a number of rounds of interviews and just before Christmas of 2020, before the Christmas period really coming in I get offered the position to join as the VP of operations, which, again, I still wasn't 100% sure what it was all about, and this was 100% remote company and I'm hoping, god forbid, this isn't like a scam of some sort, but that's what it is. So I joined January 4th, 2021.

Speaker 1: 14:24

So just after the Christmas break, into this VP of operations role and I learned that I could help, and I could help make a difference and implement some new tools, processes, technology, hire, the right people, and I learned a lot working for a small company that was really a couple of million dollar company per year, but a smaller company in terms of just the amount of people that were on it, at an accelerated rate. And I can tell you, during that time of those first few months, I think I experienced and learned more in the span of six months than I probably had learned in six years because I had grown at such a fast, quick rate, going through so many different experiences of really trying to be higher up on the chain in terms of being an executive at a startup and I called a startup because it had been around for a couple of years, but it was a smaller company that was really going through this huge growth cycle. In this real estate education space. A lot of the customers we had were entrepreneurs solopreneurs really, in fact where they were really just trying to build their own business through using real estate not just like investing in real estate, but actually turning it into an active or passive business, depending on their model that they chose. So, eventually, after six months, I get promoted to CEO, which was, again, mind boggling and crazy, and I thought it's probably happening way sooner than I kind of thought.

Speaker 1: 15:51

The challenge I had, though, is I was still very much interested in doing something by myself and had the desire still to do more, but I didn't pursue it because I kind of had an agreement that I would not pursue any of my stuff for a while while I was with the company, and so I just focused on the company, but again the same thing happened. I started to feel unfulfilled, looking for something more. So a year flashes by spending a lot of time with our customers Again, many of them entrepreneurs. I'm going to events, I'm seeing the success of other people, I'm seeing other people up on stage, and it gets me anxious again and thinking about the future and how. I don't want to live a life of regrets and I want to do what I want to do. And I started realizing I can have some success.

Speaker 1: 16:51

And then, during this same period, I started playing more online poker again and I made six figures playing poker and gambling online, after going to Las Vegas a little bit more again, as in the CEO of this company, and started winning tournaments there and realizing like the idea of going all in is something that's really appealing to me. And I started hearing people asking me a lot of questions about experiences and things that I've done. And I realized at one point that I've hired, led and promoted over 500 people throughout my career across a variety of industries and that's a lot of experiences that I've kind of pulled in. And people are asking me a lot of questions about hiring and training and onboarding. And so I create a company and I decided to call it hire for me, and I decided I'm going to do this as a side hustle in addition to my main company, with my end goal, though, to hopefully make it successful so that I can quit and go and leave on my own.

Speaker 1: 17:59

But I didn't push it hard. I got a customer here and there and stuff, and started doing some of the side stuff with it, but it never really felt like it was a true business because, again, I was doing it off the side of a desk and even if that, it wasn't really doing it to the level that I probably could or should have. So, eventually, I decided that I need to bet on myself. I need to go all in and truly become a solopreneur, and maybe one day, that solopreneur can hire other people and become the entrepreneur that's my. Distinction between the two is whether you have people or not, so I did that.

Speaker 1: 18:47

November 30th 2022 was my last day as CEO, and it was probably one of the hardest decisions to ever make was to leave the safety net of actual income that's coming in To completely bet on myself, and because I had been working so hard for so long and trying to implement a vision that maybe wasn't necessarily mine, it wasn't something that I saw long term. I took some time to give myself a bit of a break and then, when I eventually kind of went into full business mode, now it's just on me and I realized I am all in. There is nothing else. There's no one else but me, there's no other employees, there's no contractors, there's no consultants that I'm paying for, there's nothing. It is all on me. I am literally all in with all my chips. And so this ride that I've gone through now so far the time of this recording, seven months of it has been honestly insane. I'd say there's been some wild swings, there's been ups and there's been downs. I'd be honest and say that there's more downs than there's ups.

Speaker 1: 20:13

Some days where you're thinking that you're putting some content out there and you think it's going to resonate, it's going to pull in leads, and it doesn't. Or you create a webinar and I remember doing like six to eight weeks of webinars every single week and having no one show up, or maybe just a couple family members show up or support you, or having conversations with people about trying to sell products and it just doesn't work out. So, like the downs are there, but then eventually some wins start to happen where it's. You know, someone says I will buy your services. You know, you realize, okay, well, you've got that service, now you got to fulfill it, and then what do you got to do? Well, you got to invoice it, and then you're chasing people for payment and hoping that they pay you. And I've had some people who not pay me, which has been unfortunate too. So it's lessons that are learned.

Speaker 1: 21:01

There's times where you're going to figure out all the regulatory compliance stuff behind the scenes, in the background, which, I'll admit, that is one of my weaknesses I am. I am not a detail oriented person, but I am someone who comes up with ideas. And so I started to have this realization that's like, yeah, I'm kind of all in, I'd be in the sole ofpreneur and yeah, I focused initially on hire for me because I thought that was the need. There's going to be a lot of people who are going to need hiring and training support, and while people were kind of interested in some had given me verbal commitments, most people did not move forward with it for whatever reason, or they ghosted me, and because of that, I started to see that maybe that's not the right business to focus on while I have a plethora of content around it. That's not the primary thing. That is my focus at this point. So then I'm like, well, I'm the all in guy.

Speaker 1: 21:56

What's the product? Well, the product maybe is the consulting that I love to do, which was one of the main reasons why I really truly decided to strike out on my own is because I love working with business owners, consulting with them to help them develop a plan, a process, implement new technology, bring on the right people to help them grow. So I called it my all in deep dive, where I'd spend two days with business owners, really focusing in on their business and finding ways to help them evolve it, to take it to the next level. And I started selling some of these all in deep dives and, you know, starting to see the success of it and people implementing ideas and actually starting to take the ball and run with it. And it was quite amazing to have that feeling like, oh, there is some success here, I can turn into something. But then, with some of the work that I was doing, I realized, well, I'm also really really good at batch, creating videos.

Speaker 1: 23:00

In January of 2023, I recorded 143 videos for myself for social media. In one day. My goal was 50. And as soon as I hit 50, I said can I hit 60, 70, 80, 90, 100? And I stopped at 143 because I found a way to do something. And when I find a way to do something that I absolutely love, I can continue to push and push and push and go all in. And that's what I did.

Speaker 1: 23:30

So I started to realize, well, this system that I have here can be valuable for other people. It can actually give them time back. Because isn't it, at the end of the day, that's exactly what I'm trying to do? Whether I'm creating content, whether I'm coaching people, whether I'm consulting with them, whether I'm hiring for them, really the essence of any business offering that I have is to give business owners time back. And so, since I had that realization, I started actually doing video creation, content for people and for businesses. I started to really appreciate the fact that my service is about time, and that's what really every business is truly all about in some way or form. It's about saving time for people, giving them time back. That's what I'm all in on. I'm all in on creating these one person businesses that give people time back In time. I would like to make them be two person, three person, five, 10, 100 person businesses.

Speaker 1: 24:38

But it's all on me right now because I'm learning, I'm growing, I'm making mistakes, I am going through ups and downs and some of those downs really suck. It feels like you're getting punched in the goddamn face, but it is something that you have to go through. I have to go through these challenges and so I'm happy to have become the all in guy, the all in solar printer. I've tried to be, you know, focused on supplementing my income with gambling, but it just it hasn't worked this year compared to other years, and I think that's a cyclical thing. Sometimes you're going to have great years and sometimes you're not. So now it's just focusing hardcore on the business more than anything else is not focused on trying to supplement with with poker, because it's probably the universe's way of saying hey, chris, let's throw this challenge at you. How can you do it with a business? Can you grow multiple businesses?

Speaker 1: 25:34

Now, some things that people have asked me recently are a question I guess that people have asked me recently is why are you focusing on multiple? Why aren't you just focusing truly all in on just one thing? Well, I think it's because I'm maybe multi skilled and I have multiple interests and my energy level changes. I love the idea of hiring people, but it also takes a toll on you, so to sit there and turn it on and off as I see fit is valuable. The consulting thing also can take a lot of energy from me. Batch creating video content with entrepreneurs and sitting down for even a few hours to shoot 20, 30 videos is intensive. So I like to ebb and flow and I like to have options, because I can't just do one thing. So I'm the all in guy but I'm all in on multiple things that I really, truly love, because that was the whole purpose of becoming an entrepreneur is to be fulfilled. I've mentioned the word fulfillment a lot through this podcast, other podcast videos content everything I've created.

Speaker 1: 26:42

My goal for this year was to truly live on my terms, and if I want to live in my terms, that means I need to be able to do what I want when I want, how I want, with who I want, and therefore, if I have options, I can do that. It doesn't have to just be the one thing and that's it. I look back to my career where I was feeling most unfulfilled. There was a point in my career where I was so miserable. But I went to an event and somebody who I was talking to was a speaker at the event introduced themselves and explained what they did and I had thought of them only in one context. But this person said they're an author, they're a coach, they're a consultant, they're a speaker. And I was like, wait a second, you're all these things. And he said, yeah, I'm more than just one job title. And that's when it clicked for me.

Speaker 1: 27:32

I am more than just one job title to, and my job title that I had at the time doesn't define who I am, what I do or what I'm going to do moving forward. It's got to be about things that I truly love and want to do, and so I'm going to choose, just like playing poker, when I go all in and when I fold. That's part of my story. Now, there might be things that I've said here during this podcast episode here where you want to learn more about again my journey and go more specific, or some key lessons learned, and trust me, I will be sharing more, because there is tons of lessons that I have learned throughout this process. But you know, if you want to learn anything specific, just send me a message, connect with me LinkedIn, facebook, instagram, wherever it is, connect with me, happy to chat and share more about it as well.

Speaker 1: 28:28

But the journey is not easy. In fact, it is incredibly hard. It is stressful. There are many nights where I just think about what's the next step, what am I going to do? Some months are good, some months are bad. Some months you feel really excited. In the other months you're scared about what's going to happen in the future. In the day, though, I'm more fulfilled now than I've ever been. Yes, I'm a little scattered, sometimes being pulled in multiple directions, but it's the kind of life that I want and I choose for right now, and who knows what happens in the future, but at least it's on my terms and that's really truly what it's all about.

Speaker 1: 29:10

So, again, if you are listening to this and worried about taking the next step and jumping into the unknown, becoming an entrepreneur, solopreneur, and you want help, you want support, happy to connect. I do a lot of coaching in this space as well, where I will coach other fellow entrepreneurs or I'll go into full consulting mode with them and go, as part of the all-in deep dive that I have, that we can really unpack what's going on in your business to help make it better and to ultimately move forward. So if you want any of that, you can always visit chrishanaca and schedule also a call with me. It's totally free to schedule a call and connect and we'll just see if there's a fit there or worst case scenario. After 30 minutes of meeting at least, you hopefully got a couple ideas that you can move forward with to run on your own if you so choose to as well. All right, so whatever you do, remember just go all in.

Speaker 1: 30:03

Thanks for listening to the Chris Hanna Show. They would mean the world to me if you could like share and subscribe to this. Wherever you listen to your podcasts. Feel free to share this on social media and tag myself. I'm on LinkedIn, twitter, instagram, facebook, tiktok.

Speaker 1: 30:21

If you're looking for support in some of the businesses that I run, again I am the All In Soul of Praner.

Speaker 1: 30:27

I'm betting on myself and I'm going all in with creating one person businesses that help entrepreneurs gain time back and stop being overwhelmed.

Speaker 1: 30:37

I offer support in a variety of areas that some of my businesses include a video batch creation process, where I've mastered my process of how to create 143 videos in one day for myself.

Speaker 1: 30:49

I now do this for clients averaging potentially between 40 and 50 videos per session that we create in one single day. I also have a company called Hire For Me, where I literally hire four business owners who don't want to be the chief everyone officer, who want to drop the hats that they're carrying and they want to ultimately grow and scale and they don't want to hire until I do it for them. As part of my offering, I also have consulting services called my All In Deep Dive, where I literally go all in together with you as the business owner. You find quick wins, long term strategic opportunities to take your business to the next level. As part of my deep dive service, I also offer leadership coaching, career coaching and content creation, strategy coaching and development to help people really take it to the next level. You want that one on one in person or virtual support. If you want help in your business, visit chrishannaca today.