- Charging money is a whole new learning curve. Our free product was humming along. We launched a premium product and... "What?! It's not taking off?!" The

- Charging money is a whole new learning curve. Our free product was humming along. We launched a premium product and... "What?! It's not taking off?!" There's a lot to learn about where to put the "pay wall" with a freemium offering, how to get users to upgrade, how to optimize a public/brochureware site for paying conversion, etc. With content sites, I imagine there's a lot to learn about selling ads, remnant ad space, ad networks, etc. - Work on your public facing site a LOT. And measure it. In the early days, it's a constant salesperson for you. We all remark on how bad/confusing sites are, but lots of us treat the brochureware part of our business as a red-headed stepchild. After over a year of having a paid offering, we just redesigned our site and there was a 400%+ increase in conversion rate. Thinking about the revenue ramifications if we'd done that a year ago (or even 6 months ago) makes me wince. We were leaving lots of money on the table. - Don't pitch big VCs unless you want big money. They take LOTS of meetings to get to a yes/no and make very few investments. - Focus on relationships when fundraising. Almost every investor we got was through an introduction (social proof wins). - How fast your site/app is is REALLY important. - Focus on retention as a metric. The compound interest effect of retention (or return visits if you're a content site) are HUGE. Do the math. - Keep your burn low and don't underestimate how long it takes to get to profitability. We raised more than we wanted to and it turns out we needed it. - Marketing/sales wins. Almost always. The quality of your product is a multiplier on the success of your business. It's easier to build a great marketing engine on top of a great product than the inverse. VERY VERY few businesses launch a product and ride word of mouth to greatness. - PR isn't all that. Great for SEO and social proof, but it's NOT a substitute for a sales/marketing engine.