In this interview, Evan Carmichael asks Stephen Kelly (Speaker B) to share wisdom on turning the biggest risks into rewards. Kelly recounts a personal story about his father’s illness, which forced his family to find work and sparked his entrepreneurial drive. He argues that the greatest risk is losing a job or income, but the real danger lies in not betting on yourself. Carmichael expands on this, emphasizing that the biggest risk is inaction—letting fear stop you from pursuing an idea. Both stress that starting a business doesn’t require quitting a day job or mortgaging a house; instead, they advocate side‑hustles, part‑time market testing, and building cash flow before going full‑time. The conversation frames risk as a catalyst for growth, encourages optimism, and warns against the regret of never acting on an idea.
Long time viewer, Rishi Kaap TV. Do you guys have any wisdom principles about how to take the greatest risk and turn them into rewards?
Yeah, maybe I'll go first, Evan. I think, um, the greatest risk— and this is sometimes actually in life, you know, I, I've been shocked when there's, um, either personal tragedy in my— I talked about my dad's business before. This is when I was growing up as a kid, you know, my dad got sick and the reality of that is he couldn't run the business. But because of that, we never realized it at the time, but from that adversity, that was a great opportunity for us as kids to just go out and get jobs and start businesses. And that was a catalyst for my entrepreneurial spirit. And I know guys who have been fired and girls who have been fired and that's been the trigger point for them starting their own business, and they've never looked back. So I think, um, you know, Rishi, in terms of the question, you've got to really look at, um, the biggest risk is, you know, ultimately if you get fired, isn't it? If you've got no job, no income, you've got a mortgage, you've got a family, um, that's when you're really exposed. But it's, it's, it's the spirit of positivity and optimism to know that you, you've got so much to give back and you've got so much energy and passion to think of a gap in the market, think of a product or service that's going to be kind of a world beater and just go out there and create it.
Yeah, I love it. I mean, I think it relates to the quotes that you started off as well, that the greatest risk is not betting on yourself. Like, the greatest risk is, you know, putting your hands— putting your future into somebody else's hands and thinking you're going to be at that same job for the next 40 years. It's, you know, it's not going to happen anymore. And so it's not risky as much anymore to bet on yourself. It's never been easier to start a company. And you don't have to go in full-time at the start. You know, learn the market, do it part-time, get your side hustle on. You don't have to cash in your retirement savings and, you know, mortgage the house to the max because that also shortens your runway because then you only have like 2 months to make this work. And often it takes a lot longer. Where if you can still have whatever is making you money and then on the side start your business, get it growing, get some cash flow coming in, and then once you have it to the point where you can quit, you're not making tons of money, but you have enough to pay the internet and feed yourself and the family, then now, you know, when you go full-time on your business, you're able to spend a lot more time, obviously, and continue to grow. So, um, I don't know that you have to go out and take massive risks But the greatest risk of all is not, not doing anything. It's like I have this idea and then you never act on it because you think it's too scary. And then, you know, you're 90 looking back on your life and that's the greatest risk of all because you regret that you didn't take any action.
Yeah. And I think what you say there is so true. So, you know, if you're going to start a new, new biz, Rishi, then how do you do it in a way where you're not betting the whole of your life? On it. And, you know, we've just done some research with millennials to say there's very different kind of segments of millennials out there with different needs, and there's some, um, very kind of different motivations around them. But one common theme is that most of them expect to be running and starting more than one business through their life. And actually, in Nigeria— we did this over 16 countries in in Nigeria, it's amazing. They reckon they'll be running 5 businesses and starting 5 new businesses in their life, which is tremendous. And then I kind of think it comes back to culture, Evan. And I've always run companies where words I use like treat the company's money as if it's your own. And I love your concept of bootstrapping a business. And I used to, you know, when I've started businesses or funded businesses, I'd say it's really great to almost run it on fumes for a while. And then kind of build momentum, test drive stuff. When you know stuff works for customers, either product or services, then you scale it up. But you shouldn't kind of— I hate this concept. I really honestly hate this concept where you go raise loads of money, have flash offices, go flying around the world in business class and just waste money and lose the essence of why you started the business or connection with the customers. Whereas it's much better to have that culture where you're a street fighter. You're out there, you're grappling and scrapping, and you're really focused on delivering for your customers and really making a difference. But to Evan's point, you know, every step of the journey, you're kind of just thinking about what's the next risk? What's the next risk? How do I reduce that risk? How do I reduce my exposure? But you still keep that essence of a bootstrap business. And even as you grow your business, I've got a little case study of a really good company out in Vancouver, actually. Peekaboo Beans, started by Tracy Costa back in, I think, 2006. And she was, her passion was actually just amazing playwear for kids and clothes. And she started a brand, sold it direct. And then she saw the cataclysmic change in terms of buying habits between Main Street and the web. And she kind of moved her whole business, took a big business bet, so changed the whole distribution channel of all her clothing boutiques in Vancouver and went direct. But wow, she's never looked back. And what, 70% year-on-year growth? I think she employs over 700 salespeople, scalable model in, and they've got 25 employees up in Richmond at the headquarters. But more importantly, she's kept the ethos of treat the company's money as if it's your own. Remember those kind of really exciting days when we started the business. Bring that energy into your business that you had on day one when you used to take people down the bar on a Friday night, or you got a keg of beer into the parking lot and stuff like that. Those, those are the things that first of all people remember, and secondly, it keeps you true to your original values.
