In this Business Blast Podcast episode, host Tyler Wagner interviews Damian Cummings, CEO of PeopleWave, Asia’s leading HR software firm. Cummings shares a personal narrative of early career setbacks, including a failed dot‑com startup that left him homeless and in debt, and how he rebuilt his life over 20+ years. He emphasizes that the primary driver of success in any organization is the quality of relationships—being likable, politically savvy, and building friendships with key stakeholders. He advises entrepreneurs to focus on sales, marketing, and building a strong network, especially via LinkedIn, and recommends leveraging other people’s capital to fund ventures. Cummings describes purpose‑driven work as the key to happiness, arguing that meaningful contribution outweighs monetary reward. He cites The Lean Startup as his most influential book, highlighting the principle that speed beats perfection and that breaking rules can accelerate learning. He shares his favorite quote, “Be kind, for everyone you meet is fighting a battle you know nothing about,” and provides his LinkedIn URL for listeners to connect.
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Welcome to the Business Blast Podcast. I'm your host, Tyler Wagner. This episode is brought to you by Authors Unite. Authors Unite provides you with the support you need to finish your book. Best part is, after you finish your book, they take care of the entire publishing and marketing process 100% for you. So, if you want to become a successful author, make sure to check out authorsunite.com. Now, let's jump into the episode.
Alright everyone, welcome back to another episode of the Business Blast Podcast. I'm your host Tyler Wagner and today I have Damian Cummings with us. He is the CEO of PeopleWave, Asia's leading HR software company. So welcome to the show, man.
Thank you very much. Great to have it. Great to be here. Thanks for having me on. Of course, man.
Grateful to have you here. So, so, Damien, the first question we ask on this show is what is the best story from your life that has an underlying valuable message?
I don't know if it's the best story, but I can tell you one from early in my life. So in my career, I've spent about 25 years, you know, building up a good career on the corporate side. I've had many good jobs. But if I go back, I mean, I actually had to start over about 2 or 3 times in my life. Uh, after my first job, I, I worked at McKinsey and Company, the management consulting firm, and I was the most junior person in that organization. So I realized pretty quickly I didn't want to be there. You know, I didn't want to be the guy making tea and coffee and delivering the mail. Uh, but yeah, so I jumped out and actually started doing, uh, with my girlfriend at the time and my flatmate, a web development business, which was great. And, you know, you know, young 20-something-year-old kind of going into business for the first time during the dot-com boom, got excited about it, but I had no resources resources or money. So we started everything on $2,000. It went reasonably well for a few years, ended up raising half a million dollars and becoming a big company. Well, at least where we were back in Australia in those days. But what happened is that, you know, with the dot-com boom came the dot-com bust. And, you know, it ended up that the company went under. I had a huge amount of personal debts. My grandparents who raised me died at the same time, and I was kind of left homeless. So all I had was really the connections I'd made, the experience I've had, a couple of bags to live on. And I think the key message for me is, well, life didn't end. It was pretty catastrophic at the time, but I picked myself up, moved on to the next thing, enjoyed some time out, and, you know, 20+ years later, I've had an amazing life and an amazing career. So I think the key message for me is, you know, even when the worst that happens, you've got to ask yourself, what is the worst that can happen? And if you're going to take a risk, there's actually not really that much of a downside. You always pick yourself up and there's always there's always a kind of a light at the end of the rainbow, a silver lining to every decision.
Wow, man. Dude, thank you for sharing that. The next one, Damien, is what is the most valuable piece of information we should know that's within your expertise or industry?
Got it. Well, you know, I do— I've done a lot of things, so my career has really been in this idea of digital transformation. And at the moment, I run a company called PeopleWave. Now, we're a HR software company that really looks at how do you actually make work fair. So I can tell you one really important piece for anyone looking at their career and where they want to go in their career. You know, most people look at things like how well you achieve goals or how good your skills are, what kind of education you have. But the reality is the number one determinant of success in any organization or for any individual is how good their relationships are. It's how likable you are what level of political acumen you are, breaking some of the rules, becoming friends with the boss or the boss's boss. And what I found is, you know, actually after researching how to make people very successful and looking at what drives performance, it's really about how you make friendships in the role, how you build those relationships, and fundamentally how likable you are. So if you're looking to get ahead, be a likable person, make friends.
Mm-hmm. And then it could tie in, but what's your best piece of overall business advice? So not necessarily industry specific.
Yeah, I mean, in any business it's about network. So what I found is that, again, being a startup entrepreneur, it's really about being very strongly sales and marketing focused. And the core part of that is build up an amazing network. So I would say to people, you know, get onto LinkedIn, build up personal networks, go out and become a thought leader because relationships are what drives business.
And if you could give your younger self one piece of advice, what would that be?
Good question. I've never had money and I never came from a family of money. So one piece of advice is other people have loads of money. Go use someone else's money to start your business and fund your dreams. A lot of people don't necessarily want to launch their business themselves, but they do have money to back someone who's got a really passion for an idea who wants to change the world. So do it on someone else's dime.
And then in your opinion, so kind of going a little bit down a different path, in your opinion, what is the key to happiness?
I wish I could bottle that one. I mean, if I really had a good answer for that, I think I'd be a much richer guy than I am today. You know, I think it's— for me, it's about being purpose-driven. Now, whether it be launching a business like what I've done with PeopleWave or whether it be something you do in your own personal hobby or passion, it's about being purpose-driven. I've worked in big organizations and I've worked at banks where I've kind of struggled to get out of bed in the morning, struggled to go in and do that big high-paying job because there was no purpose. I mean, I felt like a cog in a machine. I can tell you, if you're purpose-driven, if you know what you're doing contributes to a purpose that's going to not necessarily change the world, maybe it's going to change your town, or maybe it's even going to change your family. If you've got a purpose, that's the thing that's actually the key to happiness. If you're living that, money doesn't really matter.
And what is the best book that you've read, and what was the number one thing you learned from that?
I'd like to sound a hell of a lot smarter, but I don't read as much as I really want to. Look, in starting up my business, I found a lot of learnings out of Lean Startup, which really taught me to break a lot of rules. So, you know, again, I'm a bit of a cliché when it comes to entrepreneurs. So yeah, read Lean Startup, a lot of good lessons out of that. And I think what I learned there is, you know, break the rules, do things differently, do things cheap and quick. So I think What is it? Fast is the opposite of perfect. So just do things quickly, break the rules, learn as you go, and you're going to be more successful.
And what is your favorite quote and why?
Again, I'm going to be a stereotype here as well. I love this quote, which is: Be kind, for everyone you meet is fighting a battle you know nothing about.
Yes, man, I love that one. Well, listen, dude, thank you so much for coming on. The last one I have for you before we let you go is where can our audience best find you online?
Well, I love going on LinkedIn, so happy to connect with almost everybody there. So I'm on LinkedIn, so it's linkedin.com/in/DamianCummins.
Perfect. Thanks again for coming on, man.
My pleasure. Thanks very much.
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