Launching a Start-Up at 40

Launching a Start-Up at 40

Sean: Hey, guys. Welcome back to the show. Sean here, your boy. Hope you’ve been well. And today we do have a special guest for you. His name is Dave Liu. And he has done a ton of things and he has been launching a ton of stuff. He wrote his book, launched his next company. And we are so privileged to learn and hear from him today. Hey, Dave, thanks so much for being in the show.

David: Thanks, Sean. Thanks for having me on today.

Sean: Dave, one of the first things that we’d love to know about you because a lot of listeners are startup entrepreneurs or they want to get their feet wet and start their own businesses. How did you do it? Where did you start? And can you share that journey with us?

David: Yeah, absolutely. So I actually started my career as a corporate guy. I was working at a major U.S. investment bank for almost 25 years. I rose from the entry-level to the executive level, and I was able to break through the bamboo ceiling. As you may be aware, a lot of U.S. companies have quite a lot of attrition among Asians from the junior level to the senior level. And that’s why the term ‘bamboo ceiling’ was created. Because when you look at the data, actually, Asian-Americans are the ethnic group that’s least likely to be promoted in America.

David: And so I started my career really as a corporate person, rising the ranks. And I was able to crack through the bamboo ceiling to become a managing director and co-head of a major investment bank running all of the Internet and digital media activities of that bank. And then I actually retired from that career in my early forties, and that was when I decided I wanted to become an entrepreneur. So I spent a lot of time thinking about the kinds of companies that I wanted to create. And during my forties, I actually created multiple companies. I started a company in asset management. I started a company in merchant banking. I started a company in media. And I started a technology company. And all of those companies, I started from scratch, from essentially an idea to a full-fledged enterprise.

David: And so to answer your question, really, I think that a big part of my desire and ability to start a company, came from actually almost two decades of training and working with many entrepreneurs. When I was a banker, I like to joke that I was always the bridesmaid and never the bride. But what that meant was, you know, I went to a lot of weddings. I was able to work with lots of entrepreneurs to see how they started their companies, how they sold their companies, how they raise capital, how they ultimately took their companies public. And so by having almost two decades of experience, seeing how other people were able to fulfill their dreams of creating companies, I think I was able to take the best of what I’d seen from other people, and also learn from other people’s mistakes to springboard and create my own businesses relatively successfully.

Sean: That’s an awesome story and saying that you did all of this when you were 40. I was assuming that you’re somewhere early forties, am I correct?

David: I’m actually going to be 50 this year, but I think the Asian blood, you know, helps.

Sean: Yeah, yeah, that helped for sure. And speaking of retirement, you mentioned earlier that you retired from the banking life or from your job as managing director. I’m wondering now what pushed you to retire? Is it the pursuit of starting up your own thing or is it just you wanted to take a break from whatever it is that you were working on?

David: I think it was a combination of several things, but I think if I had to really summarize it, it was one – I wanted to see if I could be an entrepreneur, to see if I actually had the capabilities to start my own business and fulfill what for many people view as the ultimate dream, right? To start your own business and be your own boss. And then second, it was really more related to actually spending time with my family. So when I was first working in investment banking, I was working 80 to 120 hours a week for almost 25 years. And that’s kind of the life you lead when you join a high-powered Wall Street firm. The business is highly competitive, and so you kind of need to leave it all out on the field – to use a sports analogy.

David: And so for most of my career, I obviously was – didn’t have a family, I didn’t have children. And for me, it was really all about making sure that I maximized my career potential and also saved as much money as I could. But when I turned 40, that was when I had my second child. I had my first boy and he was around three years old by then. And what I realized was that I was slowly becoming that cliche, that father, who’s never at home, who’s always on an airplane, pitching clients, working on deals. And I frankly didn’t want that for myself or for my family.

David: So a big part of the reason why I decided to start to exit, from my firm in my early forties was because I wanted to make sure that I was there for my two children. And so it ultimately took a little longer than I wanted to. I finally was able to leave the business and retire from the business at 43. So it took a full three years after I told my boss that I was planning on leaving. But I’m really glad that I did it because fast forward many years later, I have a very close relationship with my boys and I spent a lot of time with them and in fact, for them, they don’t remember a time when I wasn’t at home, where I wasn’t taking them to school or being there for breakfast and dinner and helping them with homework.

David: And don’t get me wrong, I’m sure that I gave up a lot from a career standpoint, but I really felt like I left my business in investment banking on top. I really felt that I left kind of like the peak of my potential there. And it’s been incredibly fulfilling to not only become more of a real father, but also to explore my entrepreneurial side, which I mentioned earlier, and investigate whether or not, you know, I could be an entrepreneur and whether or not I could create companies from scratch. So I’m super happy with the decision I made. It was a tough one. In fact, when I told my boss and other colleagues that I was leaving, a lot of them thought I was crazy. I had actually developed a really strong franchise and the year I told my boss I was leaving was one of my highest revenue years, one of my highest compensation years ever. And they frankly thought that you know, maybe I had been hit over the head with a baseball bat or something, but I have no regrets. And I’m really glad that I made the decision.

Sean: Got it. Wow. That was a heck of a journey, for sure. And but one thing that stands out to me is – how did you know that it was time for you to tell your boss that it’s time to resign? And I know you mentioned that it took three years for you to turn over everything and for you to make sure that you’re leaving on a good note, what hinted you that it’s high time to do this now and then on the third year, what made you realize that? Okay, you can’t wait any longer – you just have to do this?

David: Yes. So I would say that it was actually in the running you know, I was planning to do this for quite some time. And one of the things that I advocate to young people in their career, which I practiced, was observation and really studying the path ahead of you and determining whether that’s a path that you want. As I mentioned earlier, you know, I wrote a book and I have a chapter in my book where I talk about this notion, of mapping the salt mine when you first join an organization. And it always surprised me how many people join a company, start a career, and don’t really spend a lot of time understanding what their boss does or even their bosses boss does. And the reason why that is really shocking to me, is that if you’re going to invest years, maybe potentially tens of years of your life in a company, don’t you want to know where the career ends up? Like, don’t you want to know what you’re fighting for?

David: And so for me, when I first started in investment banking, I would always try to study the level above me and the two levels above me so that I would get a good sense of whether or not this was something I really wanted for my career, for my life. And what I noticed in my kind of early thirties was that there were a lot of people that had achieved incredible success on Wall Street, becoming masters of the universe, managing directors, making millions and millions of dollars, and becoming people that were highly respected in the corporate world. But I saw that many of them had very challenging personal lives. They had strange relationships with their loved ones. They had become the cliché where they had children that didn’t really know them and they had a lot of money, don’t get me wrong. But many of them weren’t really that happy.

David: And so in my early thirties I started to plan out my own path and my career, and I decided that what I was going to do was I was going to squirrel away enough money so that by the time I hit 40, I would have the option to walk away or have the option to spend more time with my family if I wanted. And so my thirties were really all about maximizing my earnings potential and salting away as much savings as I could so that by the time I turned 40, I would be able to say, you know, this is not for me anymore and I want to do something else.

David: And so when I did turn 40, I finally hit the number that I was seeking in my bank account. I finally hit that hurdle rate that I needed to be able to walk away. And at that point, there were really no excuses for myself. It was like, okay, you got to that number. You saved enough money. You live a modest lifestyle. If you’re going to stick around and potentially become that cliche, who is not around for their kids. Then you have nobody to blame but yourself. So at that point, I decided, you know what, I think it’s really time for me to pursue something else in the second half of my life. And family is going to come, number one, and then entrepreneurship is going to come number two.

David: But it ultimately did take a while to leave because one of the things that I preach to everyone in corporate America and any corporation is – don’t leave on bad terms, particularly if you’ve been with a company that’s kind of treated you well and you’ve been there a long time. At that point, I’d been at the company for over 20 years and I didn’t want to leave them in a situation where they felt that I had abandoned them and so I agreed to stay on for as long as they needed me. I helped hire my replacement. I helped transition and ultimately did take a full three years before I could exit stage right.

David: It took a full three years before we could find a replacement and I felt that the franchise was in good hands. But I have no regrets. I was able to leave on my own terms as well as leave on good terms with the firm. And I think that bears dividends throughout your career. And so I always advocate to people, if you’re going to leave your company, try to leave on good terms because the world is a very small place and you never know when your past will cross again with the people that you worked with. And you never know when you’ll need a good recommendation or suggestion on something – related to your career down the road.

Sean: 100% true. I 100% agree. And my gosh, if we end the podcast here, that was so valuable. That was so valuable for me. So many people end up in the rat race for money and lose their personal life. And you are – you, sir, are the picture of how to end that? I love it. I love what we’re talking about.