About 8 years ago, a Merrill Lynch broker emailed me and asked if I had anyone managing my money.

The company I worked for, TheStreet.com, had just gone public and I had a slug of stock that I needed to park somewhere. Our lead underwriter, Goldman Sachs, generously offered to handle our personal accounts. All I needed was another, um, several million dollars to meet its $10 million minimum balance requirement.

As I pondered not having the gazillions to join the cool cats, the email arrived from Tim. Fairly bold, I thought, emailing me about my money. No other broker or adviser emailed or contacted me during that time. Their calls didn't come until several months later, by which time I had already made my decision to work with Tim.

At first blush, this seems like an insane way to choose a financial adviser, right? As an expert on the markets, you'd think I'd be able to hack this on my own. So why use a broker from a big shop as opposed to doing it all myself?

Well, there are a few reasons:

1) I like to do a lot of different things (sing, swim, travel), including work, and that makes me pretty busy. Thus, I don't have the time to do the amount of homework I think is required to do it all myself.

2) I want someone who will talk strategy with me, helping me avoid idiotic mistakes.

3) I want easy access to a wide range of investment products. I find it easier to make one phone call as opposed to cobbling together a lot of different entities that serve specific investment niches.

I reckon that if I retired, I would do it all myself. But retirement is some ways off.

So how did Tim convince me to work with him?

Tim and I bantered back-and-forth a bit after his initial note. In the exchange, I explained that I couldn't sell my stock for some period of time, that workplace rules prevented me from owning any other stocks and that I didn't have much savings on top of that to toss into the market. Another challenge: I worked in New York while he worked in Chicago.

He offered to talk about it over dinner. So he got on a plane the very next day, we dined and I chose him as my broker.

Why? Many reasons, all of which you should consider too when evaluating anyone who wants to help you watch your money.

Trust Tim had emailed me before, commenting on stories I had written. In other words, our first interactions weren't all about my own money. If a financial adviser or broker jumps right to asking for your money, put a hand on your wallet.

Geography While it may seem odd to park money in Chicago while working in New York, I didn't think so. Most people are comfortable with their roots. I grew up in Minnesota. Chicago is at the heart of the Great Midwest, and I still consider myself a Midwesterner even after two decades in New York. Learning that Tim and his colleagues were all solid Midwesterners helped build my comfort level.

Responsiveness Tim didn't say "I'll call you tomorrow." He said: "Let's have dinner tomorrow" and flew right out to New York. It doesn't require a grand gesture like jetting around though. It can be as simple as "I'll come to a place near you" or some other indication that the adviser knows that you're the paying customer and deserve proper care and attention.

Brand Biff's Brokerage may offer lower rates, but who the heck is Biff? When handling your money, a brand helps build trust. That doesn't mean that big brands are perfect. Big brokerage firms have all kinds of problems. But you have better odds of getting your problem solved by a brand that banks on trust than trying to solve matters when Biff bolts to the Bahamas.

Flexibility Many advisers want to do things their way. That may work for them, but does it work for you? It's important to probe on this issue upfront. For instance, I told Tim I didn't have plans to do anything with my money for at least a couple of years. His response: "That's up to you."

Track record Tim's group had a strong track record and a wide ranging collection of clients that included small companies as well as individuals. He had many long-term relationships.

I'm still with Tim to this day, and I've been pleased with the service and attention I've received from him and his colleagues.

So was I smart? Or just lucky that I didn't get taken?

-- Dave Kansas