In this conversational interview, Evan Carmichael asks his guest, known as @SKellyCEO, to reflect on the advice they would give their younger entrepreneurial self. The guest emphasizes four core principles: (1) focus relentlessly on the audience’s and customers’ needs and locate where they can be reached; (2) surround yourself with teammates who share a bold, moon‑mission vision and who challenge you constructively; (3) adopt a fail‑fast, learn‑quick mindset to iterate toward a sustainable business; and (4) be a responsible risk‑taker, believing in your ideas sooner and with greater confidence. Evan adds his own insight about the power of early belief and confidence, noting that discovering and committing to belief earlier would have accelerated his own progress. The dialogue also addresses the common obstacle of family or close‑friend resistance, advising aspiring founders to stay true to their conviction while navigating external discouragement.
Chapters
Uh, next up is Chris. Knowing what you know today, what advice would you have given yourself when you were first starting? Different planning or other ideas?
Um, that's a great question, Chris. I think I would have, um, number one, you know, I would have absolutely— with my idea, I would have focused on what is the audience need, what is the customer need, what is and where do we find them? And then the other great advice I give myself is surround yourself with great people and people who challenge you, but people who are on the same moon mission as you are, the people with the same vision, the same ambition, the people who want to kind of literally fly to the moon. And if you do that, you're probably going to be hugely successful. And it might not be necessarily on your first venture, but you'll come across as you evolve your idea to success. And in the context of this and confidence, you know, be really happy if you do fail fast, learn quick, and build a great business.
This is a hard one for me because I'm so happy and grateful for where I am now that everything that led up to this moment has shaped who I am. And so if I change something in the past, would I still be here? That's the internal battle I have when I get asked this question. But I would probably, if I had to answer, would say just believe sooner and harder. Finding believe and going all in on it has had such a tremendous impact on my life and on my business. And it's been a newer phenomenon in my life. I mean, maybe 3, 4, or 5 years, something like that. If I discovered it sooner and went in on it faster and was bolder and had more confidence in it, that would probably be, you know, hopefully further ahead than where I am at now. But at the same time, I'm really grateful for my spot.
So I think I'd say, you know, be a responsible risk taker. I remember one job where I was working really early on in my career for a big, safe company, and I resigned to go to a crazy startup that did become a really successful company. But I went back for the weekend and told my mom and dad, they were alive at the time, and I said to my mum, you know, I'm going to go and do this. And she said, well, who's this company you're leaving? You know, I know the company you're with, but why would you go and work for a small startup? And she just said, you're absolutely crazy. You've got security, you've got a pension. You know, I was like 24 years old, and I was just thinking, you know, with the benefit of hindsight, I didn't take enough risks in my early career. But just, you'll get loads of people telling you the reasons why you shouldn't do stuff. But I think it comes back to your inner confidence and conviction to say, if that's what you believe in, then, you know, shoot for those stars and take more risks.
Yeah, it's an interesting question because a lot of people get that. They get— not necessarily the hate. It's not the people who are jealous, but it's the people who are still close to you, like your parents, your friends telling you not to go and do something. And for a lot of people that holds them back because they really respect and they love their mom and they want to make them proud and, you know, carry family traditions. How do you— what's your advice to people who want to pursue a path but their parents are blocking them?
That's a good question. And the other thing at the time, all my buddies thought I was crazy for doing it because I said, you know, I'm going to start up, I'll probably work 60, 70, 80 hours a week. And they said, well, we won't see you anymore. You won't be able to come down the pub for drinks and stuff. I said, well, you know, I'll still come in maybe, but I'll get here at 10 o'clock in the evening instead of 6 o'clock. I don't know. But we'll find a way to keep those relationships intact. So I think the key thing is, and I'll directly answer your question, Evan, the best piece of advice I had at that age of 24, 'cause I went and said, look, everybody thinks I'm crazy going and joining a startup. And this guy I'd worked with and knew, a sort of a mentor, He said to me, Stephen, what's the worst case that can happen? The worst case that can happen in a year is the startup folds or they fire you. And you know what? You could knock on the door of the company you've left and they'd welcome you back with open arms. And actually, you would have gained even more experience and great life experience from dealing with that failure and learning from that. You would have been a much, much better entrepreneur yourself. So, you know, when you look at it rationally and you sort of divorce yourself from the moment and then you say, well, what could really go wrong here? If it didn't work out, you can always go back to where you were. I think where you have to deal with this, Evan, is you have to be true to yourself. And it kind of comes back to the essence of where you get your confidence. No one here is living someone else's life. You only, you know, and this is, you know, it's not that profound, but we only get one shot. It's not a rehearsal and you've got to make the most of it. And the only thing that just flies past is, is time. And when you've got the energy and you're young and you can work flat out and you might not have responsibilities, it's a fantastic time to really pursue your passion and really follow your dreams. So I think the folks who are listening today, I think it's just a— it would be a time if you go home to your mom, your dad, even friends, and they say kind of the naysayers, don't do it. If you really believe in it, then, you know, absolutely have the conviction to go and do it. You've got to live your own life.
