You've put together a great deck here, thanks for sharing it!

Can you give us a few rough details of what your initial customer acquisition strategy was? (Or even something a bit more current, although I realise that might not be information you'd like to share).

From what I can tell, Sifter is in a very, very competitive market, and I'd be fascinated to know how you gained customers - and potential customers' interest - when there are so many choices out there for them to choose from.

I answered this in a little more detail further down the page, but the short version is that I didn't really have a customer acquisition strategy. I just had a little overlap from my blogging and a product that I wanted to build. The rest was pretty basic. Do things and tell people. By talking about it, I was able to reach a fair amount of people who were interested and start from there.

In terms of a competitive market, I really just kind of went the opposite direction from the established options out there. The truth is that those other apps were and are great for some teams doing large complex software development projects, but there was a whole other group of smaller teams that didn't need all of the advanced features that those big players offered. I thought the world need something between a todo list and those options, so I tried to fill in the gap.

Very informative, thank you :)

You cited early advertising as a good idea, and that continued advertising was a bad idea. Can you talk a little bit about your paid advertising strategy?

Where did you advertise?

Are you willing to share your daily advertising burn?

Any insight as to why the first $5k in advertising was worth it, but everything after that wasn't?

"Spend" is a very misleading and even distracting metric. Before going to deep into this, it's worth noting that you should never rely on advertising as your sole source of traffic generation when bootstrapping. It gets expensive, and it generally doesn't generate immediate returns. Pay-per-click can be an exception, but that's also an expensive game to get into.

Unfortunately, much of our advertising experience isn't going to be relevant due to how long ago it was. We advertised primarily on FusionAds and Daring Fireball, which has increased from $2,500 to $8,500. We don't have a daily advertising burn, and we never really have as we just dabble in advertising from time-to-time.

I'd be willing to bet that advertising has at best contributed 10-15% to our growth. Given the amount that we've spent, that's a very high cost of acquisition. However, it did help generate some awareness. There's a whole lot of context with advertising. The first $5k was relatively more effective because Sifter was so new. It was great for generating awareness. However, after that initial awareness is generated, unless you're going to spend heavily (more than $10k a month)on a branding campaign any additional impression-based advertising to the same audience generally won't be as effective.

Very helpful, thank you.

You had some pretty specific time estimates (i.e. 8760 hours in the Obsessively worried about downtime slide). What were you using to track your time?

That wasn't time tracking. That was just the number of hours in a year. :) I was pretty bad and really worried about things almost non-stop. So it was a bit of an exaggeration--but not much.

Great deck! What business entity type (sole proprietorship, llc, ...) did you end up going with and has it changed over time?

It's an LLC, but for better or worse, that's not a decision that we put a lot of time into. So it's probably not a meaningful data point.

Have you personally had any problems with this setup? It sounds like for the scope of your company it would work well.

No problems yet. (Knock on wood.) We never had any ambition plans of raising money or going public, so we just wanted the simplest structure that wouldn't require extra costs or overhead. There might be tax implications, but that's more the realm of my business partner, so I'm not really qualified to offer any extensive advice there beyond the fact that you'd want to consult an accountant in addition to a lawyer when incorporating.

What did you use to measure and export your revenue so you could make the chart used in the presentation?

It was just a matter of running some SQL queries and putting it into iWork Numbers to generate the graphs.

Thanks for posting your lessons learned.