Robert DriscollRobert Driscoll is a high-end guy with down-to-earth approachability. As the founder and owner of Venture Out, Robert has offered unique small-group tours for gay & lesbian travelers for over a decade. I asked Robert to get personal about luxury travel, business ownership and catering to queers with money. Enjoy!

1. One money expert suggests that if you are going to spend your money in search of happiness, you’re better off buying experiences rather than things. Do you agree with this statement and how does travel support this view?
Well, I think if you’re in search of happiness, then you’ve got to go with whatever makes you happy, right? For some, that means acquiring things ” the right food processor, an awesome car, a fabulous hairdo. For others, it’s all about experiences. I guess I fall into the latter category.

What’s made me happy over the years are the experiences I’ve had interacting with a great variety of people and the incredible sights I’ve seen all over the world ” In connection with my business, it’s producing such experiences for the gay & lesbian travel audience that has also brought me a great deal of happiness ” and generated true gratitude.

2. What is your most significant memory about money?
It’s when I unintentionally parted with some ” actually, a whole lot of it. I was in Madrid taking a tour of the Prado Museum with some other gay tour operators when I realized I had left a staggering amount of Euros at the hotel I had just checked out of. My next stop was to be Italy where I was running a cooking vacation on the Amalfi Coast and where my Italian vendor insisted on being paid in cash for the 12-person tour group.

So I had put the money in the hotel room safe ” something I never use — so of course, I forgot all about it when I checked out. After a mad taxi ride through 95-degree Madrid heat back to the hotel, I was reunited with my money as no one had checked into that room yet. It was just a little too close for comfort.

3. What is your worst habit around finances?
Despite what I just recounted, my worst habit around finances is not carrying enough cash around with me!

Oh… And not charging enough for Venture Out’s trips! If people only knew how much time, effort, and frustration goes into pulling off a seamless, unique, innovative tour, they’d better understand the value of what they’re getting.

4. How did you earn your living before starting Venture Out? Ten years later, are you happier now?
I’m a several-time retread. Number cruncher on Wall Street; math teacher in Vermont; MBA from Berkeley; more corporate number crunching ” and then the inevitable professional crisis. I got into the travel business by fluke, really. I was unhappy in the corporate world, so I quit and went to learn Italian in Italy where I met an English couple who were starting up a bike tour company, and they asked me to help them market it in the States. One travel gig led to another until finally, tired of organizing trips for another tour company for Mr. and Mrs. Here and Mr. and Mrs. There, I started a gay travel company. And yes, I’m happier 10 years later.

5. With regards to Venture Out tours, which destination offers the best bang for your buck?
Well it sure ain’t Europe right now. With 1 Euro costing $1.40 today a trip through most of Europe can be staggeringly expensive. On the other hand, we’ve got this deluxe gay cruise up the Danube River in October which has turned out to be an exceptionally good value because our vendor, the riverboat company, is an American firm and quoted the charter to us in dollars. I imagine they’re the ones taking the hit because all their expenses are in Euros. So our guests get their accommodation, meals, sightseeing, and transportation all in one good-value package. Apart from that, Latin America is a good region to get decent bang for your buck. We’re doing tours to both Argentina and Peru this fall, and they’re selling well.

6. Your tours are billed as high-end so you probably interact with a lot of wealthy guests. Are rich people happier or just better fed?
Oh, why yes, they’re very happy ” and oh, no, those shorts don’t make you look fat at all…

Kidding aside, it’s true that we specialize in high-end gay tours, but are our guests “happier” than those who don’t have the means to do our types of trips? I don’t know if they are or not. But I do think the nature of our vacations is such that a natural self-selection happens, and most of the people who come our way are very comfortable with themselves, good-natured, and not easily perturbed.

7. If you only had $300 for a weekend get-a-way — where would you go and what would you do?
Living in San Francisco, one has a lot of nice options. I’d go to the Tassajara Zen Mountain Center in the Santa Lucia Mountains, east of Carmel Valley, and do not much of anything, really ” except eat delicious food, soak in the hot springs, go on a nature walk, read, nap, clear my head, recharge the batteries… you know, that sort of thing.

8. Is there a price attached to being a small business owner, especially in a line of work that is queer specific?
Uh… yeah, you could say that… For me, it’s a 60+ hour work week and the uncertainty (and resulting stress) of not knowing how the bank account is going to look from month to month. But I derive so much pleasure in working out terrific tour itineraries and introducing people to new places that it almost always seems worth the long hours.

And I also think there’s some social value in organizing gay travel — bringing gay tour groups to small towns all over the world. We show the world that, hey, we’re just people. We’re just like you ” well, sort of.

9. Which is more important: how much money you make, how you spend it, or where you live?
You can make $100,000 in New York City and it’s not going to go as far as $100,000 in Fargo. But then you’re in Fargo. I’m sure there are many great things about that part of the country, but being able to get up and go is easier when you’re near a transportation hub. Ultimately, though, I think it’s how you spend it that’s important, which is one of the reasons we have so many repeat clients and why we get so much business by word of mouth. Our travelers find they get value for their money, and two days into a trip in Spain they’re asking for a tour to Turkey, or Chile, or South Africa, or …

10. What was the best money lesson that you learned from your parents?
I think I learned from them that money shouldn’t be squandered. But I also learned, after observing their habits with money over the years, that life should be enjoyed, and it’s OK to spend money in the “right” ways. I watch my 94-year-old aunt, who has way more money than she’ll ever need now, continue to hoard it and not part with a penny.

Get out and enjoy life. Indeed, Venture Out!

More about Robert Driscoll
Robert Driscoll is the founder and owner of Venture Out ” a tour company that designs and operates unique, upscale, and fun escorted tours around the world for gay and lesbian travelers. Robert started the company in 1997 after quite a diverse professional history.

He spent several years as a manager with a variety of more mainstream tour operators before venturing into self-employment. His professional background also includes financial analysis work as well as writing and editing. Robert obtained his MBA from Berkeley and BS from the University of Vermont.

His hobbies include travel (of course), enjoying fine food and wine, keeping current with current events, working out, and relaxing when it’s possible. Robert lives in San Francisco and works, well… all over the world.

Read other Queercents interviews in the Ten Money Questions archive.