Don’t pity Jonathan Kaplan. Yes, he had to watch as Pure Digital Technologies, the company he founded and sold to Cisco, was dismantled earlier this year. And the Flip cam — the revolutionary, low-price HD video camera he pioneered — ceased production. But that just left him more time to pursue his real dream: a chain of grilled cheese restaurants.

Kaplan approached the grilled cheese sandwich the same way he approached his tech ventures — securing capital and working with engineers to create the perfect machine for toasting the bread and melting the cheese. He opened his first Melt restaurant in San Francisco in late August and has plans to open 500 more. His theory — and he might have a point here — is that people are looking for comfort food these days.

My approach to grilled cheese has been quite different, although there are times when I think I might benefit from securing cash from a venture capitalist to fund my cheese purchases (my favorite cheddar hovers at around $30 a pound). But ever since I read about Jonathan Kaplan’s new restaurant concept, I’ve been obsessing about new ways to approach the grilled cheese sandwich.

So this weekend, I decided it was time for the Great Grilled Cheese Experiments. I picked out a nice loaf of sourdough and a few different cheeses and sat down to plot out my sandwiches.

I decided to try three different sandwich combinations. The first sandwich was the simplest, and a variation on one of my favorite recent sandwich discoveries: thinly sliced radish paired with fresh mozzarella. While this is refreshing and delicious served cold on a baguette, it ended up a little bit soggy and lacking in flavor when grilled on sourdough.

My second entry in the Great Grilled Cheese Experiment was a simple aged Gouda and Dijon with sliced dill pickles. This one rated high with my sandwich testers. Gouda melts nicely, and the creamy nuttiness of the cheese worked well against the pungent dill. The pickles (I went with McClure's garlic dill slices) held their crispness nicely too.

The clear winner of the night, though, was an eggplant, tomato and pesto grilled cheese with mozzarella. This was a surprise for me. First of all, my testers were both avowed eggplant avoiders. And frankly, I expected one of the more simple sandwiches to win. But this sandwich was far and away the most delicious of the bunch.

The eggplant was a gift from an AnnArbor.com coworker, passed along from a family member with a very productive garden. I wasn’t sure whether my best bet was to roast it or fry it, so I tried both. The roasted eggplant came out much better than the fried eggplant, both in flavor and texture.

The next decision I faced was about the cheese. Fresh mozzarella or a brick of part-skim mozzarella? Having already whiffed on the radish and fresh mozzarella, I went with part-skim brick, since it’s lower in moisture and less likely to make the sandwich soggy. I sliced up one of my last red tomatoes from the garden, sprinkled on some grated Parmesan, and finished it off with some basil pesto.

I worried that I had made the sandwich too complicated; that it would fall apart when we tried to eat it. But this thing was heaven, and it really wasn’t that messy.

This sandwich is a far cry from the grilled cheese sandwiches I used to make in the toaster oven — the ones with processed American cheese slices and hothouse tomatoes. There’s still a place in my heart for those. But for now, I’m having a lot of fun creating crazy new grilled cheese concepts. Maybe I should see if Jonathan Kaplan wants to share the number of his favorite venture capitalist …

Grilled Mozzarella, Eggplant, Tomato and Pesto Sandwich

• 1 medium eggplant, stemmed and sliced lengthwise in 1/4-inch slices
• 4 slices sourdough or similarly dense bread
• Butter or margarine
• 4 teaspoons basil pesto
• 2 teaspoons grated Parmesan
• 4 ounces part-skim mozzarella, sliced (or more, if you like your sandwiches cheesier)
• 2 small or 1 large tomato, sliced in 1/4-inch slices

Arrange the eggplant slices on a cookie sheet, salt and pepper them lightly, and put them in under the broiler, on low, for about 5-10 minutes, or until they have just started to brown. Remove them from the oven and set aside.

Lightly butter four slices of bread. Place them on a plate or cutting board, butter side down. Slather the other side of the bread with pesto; one tablespoon per slice.

Layer two of the slices with enough cheese to cover the bread, followed by two slices of eggplant (trying not to overlap the eggplant slices), a teaspoon of grated Parmesan, tomato slices, and more mozzarella. Top each with the remaining slices of bread, pesto side down.

Set a medium skillet over medium heat. Place one sandwich on the skillet, and cover with a lid. After about two minutes, or when the bread has just started to brown, carefully flip with a large spatula. You might want to guide the top of the sandwich with your other hand as you flip.

Replace the lid and cook for another two minutes, or until the bread has started to lightly brown. Remove the sandwich from the skillet, slice it in half or quarters, and serve immediately.

Makes 4 grilled cheese sandwiches.

What is your favorite grilled cheese combo? Do you butter the bread or brown the butter in the pan? Share your grilled cheese tips and stories in the comment section below!

Jessica Webster leads the Food & Grocery section for AnnArbor.com. You can reach her at JessicaWebster@AnnArbor.com.