San Francisco: Pretty, Pricey

The steep hills of San Francisco aren’t just challenging for parking, they are synonymous for the steep climb start-up companies are facing in a place that’s perfect for surfing and riding bicycles and, as we have learned, for growing a business. Fellow entrepreneurs, venture capitalists, industry analysts, social events, conferences, it all happens in this neighborhood. However, there are many competitors in the race for funds, so you have to run fast to get there first. And while you do that as a frugal startup artist, you’ll be spending some bucks.

Rents are outrageous. $3,000 for a two-bedroom apartment in a decent area of the city is the norm. Service providers like PR agencies are plenty, but most of them aren’t looking for cash-strapped clients. If you have budget, you’re OK, but if your prescribed monthly burn rate for the entire operation is $10,000, you better get used to the thought of raising more cash or sending out press releases yourself.

Clocks are ticking faster, too. Not just those of the old-fashioned parking meters, where a quarter of an hour seems to have only 12 minutes, but also the clock that determines the cycle of cool new business models. You have to be alert and proactive or you look old in a hurry. The fact that your site offers social networking hardly getting you attention, because a lot of others are doing it, too. Here, a good idea never lives underground for long. And once others see the merit, they take it, they shake it, they spin it and tweak it to make it into the next big thing. Invigorating and challenging.

Luckily, there are escapes. At the bar of the posh St. Regis Hotel, next door to the Museum of Modern Art, we connected with David Silverman, a colleague from the early days of electronic commerce at Intershop, who now is with Aggregate Knowledge, a company that connects consumers to hot products, interesting content and cool items. Joining us was Michelle Gildersleeve, who also worked at Intershop and now is with a small outfit called Oracle;-)

For some exercise we climbed the steps from Levis Plaza, the home of the original 501 to the urban oasis of Telegraph Hill and descended down the west side into North Beach http://www.sfnorthbeach.org/index.html, San Francisco’s Little Italy, right next to Chinatown. It’s a Bohemian and touristy part of the City, which at one point or another served as a hangout for Marilyn Monroe and Joe Di Maggio, and of course, the titan of the Beat Generation, Jack Kerouac.

It was here that Kerouac got inspired for his seminal novel On the Road, which he wrote in 1951, in only three weeks, typing it out on a 120-foot scroll. Caffé Trieste, City Lights Books and the colorful corner of Grant and Green–not just a tribute to the famous jazz guitarist–are a few other places you should keep on your short list next time you visit.

As for us, we will be back soon.