We weren't all that successful, but we had a lot of fun and I learned a tremendous amount at a very early age. Thomas Young: That's awesome. Yeah, it's crazy how sometimes you just stumble into a world that you never expected to be a part of. For example, that was me with the self-directed space right out of college. And it was, I needed a job and a job offer came up and I had known nothing about solo k s or self-directed IRAs or any interest in retirement.
And once I got into the world and started learning about it and started realizing the power of self-directed accounts and retirement, just in general how important it is, I drank the Kool-Aid and it's become a big part of my life at this point, obviously with Rocket Dollar. Sometimes, it's, you just got to take the opportunities as they pop up. Brooke Borden: Yes. And then shortly after that, after working about five years in Southern California, after I graduated, I was pretty much flying back and forth between LA and New York quite a bit, almost every week because most of our clients were in New York.
And I remember going home and telling my wife at the time, I'm like, "Look, I'm really tired of spending all this time on airplanes. Why don't we just move to New York? And in a short time, I found myself working on Wall Street. It seems to be a recurring theme in my career, I also had a very lazy boss there and he had hired me to create a mergers and acquisitions department. But we never ended up hiring the next person after me, which was supposed to be the head of corporate finance, which in Wall Street investment banking is the guy that goes out and finds IPOs and does the underwritings of IPOs.
Because we never got around to hiring that person, the job fell to me.
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It was a very good learning opportunity. I learned a lot about how the IPO process works, setting up the documents from the underwriter's side, doing the book-running part of it, filling up the syndicate. So, it was all a very good experience. Thomas Young: You were just a year older than I am right around the same time. That's awesome. And not only did it take you to New York, but you've lived all over the world. Tell us when your world-traveling started, and I mean you've lived in some pretty cool places. During that time, I worked on Wall Street as I had said, the first job that landed me there.
And then I actually had my startup for a while. It was one of those things where it was a great idea and really bad timing. We launched the company at the end of And we're up and running and ready to launch, and all of our software worked and the whole website, and got our broker-dealer license in March of , which of course was when the NASDAQ-. Brooke Borden March 8th, when the Nasdaq crashed the end of the internet 1. So, we pulled the plug on that startup.
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Brooke Borden: Yes, we did. And actually, for a lot of my angel investors, it was their best internet deal because they got 82 cents of the dollar back when we shuttered the company because we didn't spend very much of their money. Thomas Young: Yeah. Just a little aside on startups, how did you decide to pull the plug with that much money still in the bank?
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I mean, what caused it and how did you know that it was a good idea instead of weathering on the way so many startups seem to? Brooke Borden: Well, the business model was pretty much doing accredited only investor matchmaking for angels and startups. Now, you have a lot of people in the market doing that. Here we are, what, 28 years later, it's become a more established model. But back then, the SEC was still very strict around these must be accredited investors.
Everything must be done through a broker-dealer. There weren't any of these unlicensed platforms out there. It just became very apparent to us that the exits to those deals were gone. People couldn't see that if they invested in a deal that A, they would get the next round of financing. And then even if that company was wildly successful, there was no longer an IPO exit available for them.
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Because I don't know if any of y'all remember, but the severity of that stock market crash was very severe. Thomas Young: Yeah, I don't remember it. I was But no, that's cool. You had your startup experience, and then what did you do after the startup? Brooke Borden: Shortly after the startup, two partners, friends of mine in New York, we went around and we figured, "Hey, the valuations are down, multiples are down, let's go see if we can buy a company, a regular operating company. And we finally just gave up on that after about a year and a half. We just couldn't ever get over that last threshold to get the entire deal done.
And yeah, it was a good time to leave New York for us. We had been there seven years. We were getting kind of tired of living in Manhattan. Manhattan is the kind of place you either love it or leave it.
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And after seven years, the love was, it was extreme like. It wasn't love. So, it was a good time to leave New York. And like I said, that company also had a broker dealer. So, we did a lot of syndicated capital raises. We raised almost a billion dollars for hospitality and real estate projects in the Midwest through that entity. And most of those investors were clients of the accounting firm that we were catering to as well as building an independent broker dealer distribution network.
I did that for five years. And then it's kind of interesting. I got an unsolicited phone call one day from a recruiter asking me if I'd be interested in a very high level and a high profile position in of all places, Saudi Arabia. I thought it was a joke. I didn't really take it very seriously, but the recruiter finally convinced me that it was for real and put me in touch with the vice chairman of the bank there in Saudi Arabia.
One thing led to another. And after a series of negotiations, I found myself in Riyadh, Saudi Arabia.
Thomas Young: It seems like the theme in your career has been opportunities and just being flexible and being open and then just deciding what the best path for you is and then going from there. Brooke Borden: Well, I've not really done it in a conscious way, but I've developed a set of generic skills that each on their own, it's not really impressive.
But when you look at it and say, "Oh, well, this guy can do this thing, this thing, this thing, and this thing," pretty soon you're like, "Wow, that guy can do a lot of different things. Thomas Young: Yeah, I think that's a similar theme in my career in that, we talk about the 10, hour rule and being deep specialists, but it seems like being a competent generalist opens up a lot of doors for you because then you don't get pigeonholed in any one thing.
At least for me it's worked out nicely, and I think for you as well. Brooke Borden: No, it certainly has. The most interesting thing about my foray into the Middle East was not only being exposed to a very interesting culture and meeting some really wonderful people, but my second stop in the Middle East was with a large financial institution in Bahrain. Banks in the Middle East have a different view of private equity. Brooke Borden: They don't have the same capital rules locally that we have here in the US.
So, a lot of them actively participate in their private equity deals that they promote. When I landed at Shamil Bank in Bahrain, a good one third of that bank's balance sheet was tied up in private equity assets that they had invested in themselves. Brooke Borden: Which was fine because it was , when they had made all these investments. However, my timing seems to always be really good because my first day of work was August 8th, which was the day that Lehman Brothers blew up.
Suddenly we went from having a mindset that we're going to go out and continue to do these great innovative and fun deals to now we have to defend the bank's balance sheet against our auditors and write downs because our capital ratios aren't looking so good if you start looking at the true value of some of the assets that they had. Thomas Young: Wow, that's interesting.
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