Tripit and every other VC-backed company is in a completely different business than indie devs making apps. The product that companies like Tripit are selling, right from the beginning, is the company itself, not some free or cheap app. The app is just a marketing vehicle to increase the price of the company.
The amazing thing is that PG himself has been clearly saying this for years. And we still refuse to accept it!
Blindly copying VC-funded startups' surface tactics is the second leading cause of indie developer homelessness.
If you are in the business of business, you've got to sell. Successful entrepreneurs, whether VC-funded or bootstrapped, know how to sell.
If you are funded, it would be stupid to try and do anything that doesn't increase the valuation of your company. The best founders know how to weave a compelling story, and are always selling their company. Always.
The most successful bootstrapped entrepreneurs are always selling their product. Notice how patio11 does not miss an opportunity to somehow weave in a mention of one of his products, while still coming across as the most helpful guy ever (because he is). And when he's blogging about SEO and other useful stuff for other entrepreneurs? He's selling his consultancy services.
If you're not selling, it's not a business. It's a hobby.
ABC: Always be closing.