225. A Message For Every Entrepreneur & Investor. How To Back Yourself And Not Live With Regret.
2 Jul 2025 · 13 min
Podcast episode (Ben Simpson & Bergs) built around a short external reel urging listeners to "bet on yourself" and "say yes" to time-limited opportunities. Hosts reflect through personal anecdotes (marriage, illness, starting/joining Collective Shift, near-ruin business moments) about choosing uncertainty over comfort, enduring short-term pain for long-term growth, doubling down during market bear phases, and the role of mentors/peer accountability. Practical takeaways: prefer the pain of discipline over regret, increase your surface area for luck, surround yourself with top-quartile people, audit your information diet, and explicitly write down and assess your worst fears before acting.
Chapters
Welcome back to another episode of the bennetbergs podcast. I'm Ben, your favorite high school dropout and founder of Collective Shift alongside Ms. Bergs, your favorite MBA and CEO of Collective Shift. We're here to bring you world class crypto research strategies and insights to help you crush this crypto bull market. Plus, get an exclusive behind the scenes look as we scale Australia's leading crypto research company. If you like the podcast, please share it around with a friend or family member. It's how we grow the podcast each and every week. Now we want to play a little reel for you guys. Listen to this. It's a reel from the Diary of the CEO podcast. We'll let the others play this one.
Now, what is the advice that you wish you'd gotten at my age that you didn't get?
The most important thing is probably keep betting on yourself and bet again. And roll the dice. And roll the dice. What happens as you get older is you realize that these opportunities were in front of you and you didn't jump for them. Long life can be understood as a series of opportunities that are put before you and they're time limited. So your philosophy in life should be to say yes to that opportunity. And yes, it's painful and yes, it's difficult and yes, you have to deal with your family and yes, you have to travel to some foreign place and so forth, get on the airplane and get it done.
Bergs, what do you think about this reel, mate? It hits home a little bit.
It's what everyone needs to hear to get off their asses and, and be like, yes, I am going to do the thing.
Roll the dice, keep betting on yourself, say yes, the opportunity. Yes, it's hard. Get on the plane.
All just this conjures up so many memories. I remember this would have been 2015, so we were commissioning Fiona Stanley, hospital opening a new hospital, mental. Just got married in like 2014.
Wife was pregnant and daughter was born in 2015. Plus doing my NBA. Yeah, I think I said they're doing my MBA as well. Dad was getting sick, like all this stuff was going on and I was like, yes, yes, yes. And I look back on that and I'm just like, you're mental. No wonder you got sick. That is ridiculous. But it is just one of the biggest step changes in my life where I said yes to all the things and the amount of growth was insane. Yes, it sucked. Yes, it hurt. Yes, it was uncomfortable. But saying yes to that just accelerated my entire life. There are so many learnings out of that few years is just absolutely incredible, man.
Yeah. I think you're back. All right. So you keep going. Keep going.
Yeah, yeah. No, and then, you know, even after that, like another one was like joining collective shift, jumping in, saying, yes, choosing uncertainty over unhappiness, and then just going, oh, this is great for a month. And then, holy, this plane is crashing. We gotta fucking put it back together. And at any point you can bail out, but you're like, no, I want to go through this experience. I want to have that grit. I want to learn. What do I need? What do I need to learn? Experience, resources. It is just betting on yourself that you will figure it out and you will be okay. And the reality is you figured out everything in your life. Everything is okay. If you didn't figure it out, you'd be dead. And you're not dead, you're fine. And so it's more just, am I willing to suffer and be uncomfortable and be in this pain and really work through this to see if there is a bit better outcome on the other side or am I just going to give up?
Yeah. And I think that when you are feeling uncomfortable and you're feeling.
Uncertain and it feels like, you know, you're scared about whatever you're doing, that that is the biggest growth area. And I think that's like that.
Rock bottom that I hit when the ex Business partnership went completely to. And I had that decision I had to make was whether I'm going to give up and go do something else or go all in on collective shift and try and figure it out. When everything was against me losing money, like members leaving, we're down 80%, you know, legal stuff was going. It was a shit show. And you know, naively probably at the time just went, it, I'm trying to figure it out was the. Was the reason I'm here today. And that was just a decision I made. And if I said no, none of this would have happened. Which is crazy to think about because I was so close to going this, I'm out.
Oh, mate. So many times. And you gotta. You gotta risk it for the biscuit. Right? And now I'm to the point where.
Like I. I use a couple of mental models and it's when I have a choice which will increase my surface area for luck, which one will result in more growth, which one is more painful. And nowadays I will choose the more painful option because I know there is an opportunity for growth. Yeah, the pain is only short term and it gives me more reason to not be comfortable to exercise that muscle, get uncomfortable and grow rather than just sitting on my fat ass and going, everything's okay, I don't have to move. I'm like, no, I'm going to start moving.
Yeah, that, that, that thing you said in the real about looking back on opportunities that you didn't take and life is just a, like a continuous, you know, opportunity wheel and looking back on the opportunities you didn't even know. And maybe you said no to that. That is scary for me. Like, that feels like big regret. Especially before I've got kids, before I've got a mortgage, before I've got like huge commitment. I've got this window where I really want to try and do as much as I can, say yes to as much as I can. Because down the line it's going to become far harder to do that. Right. And as you probably know, your, your priorities change. Right. Like, you know, your, your life right now is, is, you know, family, family oriented. It's family first, which it will be for me too.
Not to say you can't take up opportunities, but it becomes a lot harder. Right?
Yeah. And you need to think about any decision. Do I want the pain of discipline or do I want the pain of regret? And I'll always choose the pain of discipline. I used to choose the pain of regret where, you know, it'll be, don't take the job, don't go on the holiday, don't go on the plane, don't talk to the girl, don't call the girl, whatever it may be, because you're afraid, or don't do the course or don't go do this crazy physical thing, run a marathon, whatever it may be, and you lose out. And I'll always choose a pain of discipline over the pain of regret. And it's the same with going to the gym now. Like, I've been sick for a month or so and I'm suffering, but I want that discipline of getting back in rather than going back to the old body and old sickness that I have and having that pain of regret of what could have been that will destroy me. And it comes back to easy choices, hard life. Hard choices, easy life.
Yeah. Yeah. I, I, I look back at like the things that have given me, the opportunities that I've taken that are now paying off the most are the things that I looked the most stupid when first starting. And it was so hard to get over the, over the line. But the biggest ones were speaking in front of camera, doing content, speaking publicly, doing my TEDx talk, raising money for their business raise 1.5 million every three of those four things. Those biggest, like those four pillars that be the biggest impact for me personally if I go back and watch myself in any recordings when I first started, look like a fucking idiot and still do.
Mate.
You're right. Look at how far you've come and look at the way you speak on camera now and what you're talking about is am I willing to suck? I want to start a new thing. I'm going to be back in the package. Hey, but I've already got this job. I've been here five years, I'm top of the waza. I've got all this status. Am I willing to suck, be a beginner and start again for the potential of having something far better than I have now? Yeah, and we did that with Bennetbergs as well.
Yeah, it's the long term game. We were willing to play the long term game. We weren't chasing those quick wins. The reason why we're here and we out compete with everyone. And even with our best investments we had conviction, delayed gratification, which is very hard, has become our advantage, you know, and we held on. And again, even when like crypto in a bear market, whether you look at your investments as a personal investor or business, whatever, when others freeze, give up, go to the next thing, AI NFTs, whatever, you know, we doubled down and looked at those, you know, those uncertain points and saw the opportunity and double down even when it wasn't popular, even when everyone or stupid has paid off massively.
So yeah, yeah, it's, it really is about endurance. How much pain can you endure during those difficult times when everyone's telling you no, you're even telling yourself no. You've got your ego that's like, no, you, you're better than this. You don't need it. You've got that identity that tells you no, this is not who you are. You can't be that person, you've got that fear that says, oh, what if I fail? What if it doesn't work out and I lose the thing that I've got.
Now that's a big one. Like I still struggle with that like that limiting, limiting beliefs thing and the people you surround yourself with limiting those beliefs of what you're actually capable of. And that's a big one, you know, and even I feel that like now the, where we're at in the business and where, you know, I want to, I want to get to personally, business, whatever. There's not that many people you have to surround yourself with those people. Otherwise like where you get to, you become comfortable and you don't know that that's even possible, you know. And that's why I think surrounding yourself with the right people is so important as well.
If you want to be, let's just say the top quartile, you need to surround yourself with top quartile people your whole life. You haven't. They're people that are just, you know, average like you. They just do the things that you do, you do the things that they do and you need to see a different way in life and you need to bust through all those other people speaking in your head and those self limiting beliefs that you think are you talking to yourself when it's really someone else getting rid of those going and doing the things, accelerating, accelerating and getting into that quartile you want to be in.
So true. And that biggest, that one of the big. My biggest fear points is. Yeah like thinking about me getting older and looking back and saying no to that opportunity.
That is in reflection very obvious that I should have done it. But I didn't because I was scared, worried, didn't want to do it. Especially at my age when I feel as though I can still take that risk and I don't have ultimately that much to lose because I know I've got time to rebuild it different if you're a different stage of life. But yeah, you know, I want to make sure I'm not getting comfortable and not trialing those new things because there's going to come a point where you can't do those things anymore. Like just life doesn't allow it.
Yeah. You could do everything you want in your life but you have to decide when like you're not going to go Snowboarding in your 70s, you should do it in your 20s. Right. Like and this is it and this is where mentors and coaches come into it, where they, they can help and even psychologists can help you mediate your thoughts, understand what you're thinking and give you a different perspective so you can understand the situation better and make a better decision.
Yeah, it's about, on and you've done.
A lot of that.
Yeah, yeah, yeah. It's a, it's a, the, the advisor piece and surrounding myself like in EO or like meeting cool people, reaching out like Nathan from Founder who have become buddies with, you know, catching up with him for dinner. Like these people that have done cool things and are doing amazing things and seeing how they are also everyday people and how they've done it what their lives are like. It's just like, it's so inspiring.
Yeah. You have to unlearn and unthink and think in a different way. Because otherwise, if you think like everyone else, you're going to be like everyone, which is totally fine. But if you want something different.
Yeah.
You will have to think differently.
And even auditing, like, your content that you listen, you know, that you're consuming, like, that's a big one.
What are you putting in your head?
Yeah, dude, huge.
That's exactly right. Like, who are you surrounding yourself with? What are your. What are your habits? What are you listening to? What are you shoving into your head every day? And that will frame up the way that you think. This is why marketing works. This is why you buy things and you don't know why. This is why you have brand association.
Say yes, get on the plane. I love it.
Say yes, get on the plane and don't be afraid. Even like eo, one of the biggest things is like, the coaching and mentoring and peer group is nice, but the biggest thing is accountability. You have to be like, what is the thing that sucks? This sucks. I'm committing to doing it. I'm coming back to you next month and if I, if I haven't done it, I know I'm going to get a huge belting over my head and it gives you that strength and accountability to go and do the thing and progress and move forward to where you want to go.
So true. Say yes, get on the plane. I love it. Surrounding people. Don't regret it.
Get on the rocket ship. Let's go.
Thank you, everyone. I hope you enjoyed that and you can take that into your own life. Entrepreneurial, discovery, you know, investment career, whatever you're looking at. I think that's just a great little. A little clip to remind.
It's a reminder to get after it.
Keep betting on yourself. I love that.
You're not going to die, you're not going to lose heaps. Write down the worst thing that can happen. Write down your worst fears, look at it, see if you can accept it, see if you can mitigate it and then get after it.
Let's go. Get after it, folks. Hope you enjoy the episode. Share around with a friend or family member if you enjoyed it and we'll see you on the next one.
Thanks, champions.