garrettdimon

I would say that deciding not to outsource anything is a mistake. We regularly turn to great people to help with some JavaScript features or systems administration. We've even had some folks help with Rails work a couple of times.

Thus far, without being able to hire full-time, outsourcing that stuff was the best decision that I've made yet. It enabled us to launch some features that might have otherwise taken me forever to get around to building.

I couldn't agree more. It was initially my biggest fear, and some of my experiences had begun to make me feel that way. However, as time has gone, I've realized that it's really not that bad. The only catch is that the option of going on a vacation to a remote location without internet and cell phone access is out of the question if you don't have a backup person.

I used to think that adding a second full-time person was the solution for alleviating pain, but now I see it as the way for all of the work to simply be more fun because there's somebody else to help accomplish more.

That could probably be a post by itself. The way we've evolved to add additional layers of automation and support, adding an FAQ, and other related improvements have definitely helped. However, when you're building an app by yourself, everything takes time, and it's not quite so easy to make time to perfect a support system overnight. So, in our case, it's simply just evolved as we've grown.

That was one of the points of the article. At first, that fear dominated my life. As time has gone on, and a few things went wrong here and there, I've learned it's not quite that bad.

Also, we have a very different view on customer service. I strive to respond to all customers immediately. We could reply within a day, but going above and beyond for customers is important to me. The support requests in the middle of the night aren't even a problem. It's just part of the gig.

I may be a little late to the party on this, but it's definitely possible. There are times where regular hours are impossible, but for the most part, it's definitely possible. I agree wholeheartedly with everything Amy has said about their experience with Freckle.

In the four years since quitting my day job to freelance and build my app, I've gotten engaged, married, gone on a honeymoon, got a dog, gone to Europe for a week, and had our first child. I also regularly go on vacation and go snowboarding. I've been full-time on Sifter for about half of that time. So I was part-time for about two years, and that was hard work balancing the two, but it wasn't that bad. I just split time between freelancing and building the company. It was stressful at times, but well worth it.

In my case these days, as a solo founder, it's a bit involved. I work every day, but for the most part, I still only work 40 hours per week. I work from home and see my wife and daughter all of the time and find time to go to the gym every single day. I take breaks and spend time with them whenever I want, and I just work whenever it fits into the family schedule. The only catch is that it's very hard to stop thinking about work in my downtime, but I think that has as much to do with me and being passionate about work as it does being a business owner.

It hasn't been a cakewalk by any means, but it's entirely possible. I've got a slide deck that covers some of the personal side of things if you're interested. (http://bootstrapping.sifterapp.com)

I believe the point is less about revenue being a guarantee that it won't happen and more about the fact that a lack of profit makes it increasingly likely that the product will eventually be shuttered because free isn't a sustainable model.

I can't find the information, but my understanding is that this approach isn't good from an accessibility standpoint because a screenreader still interprets the icons as their corresponding character and reads that character. As a result, instead of ignoring a checkmark icon, it would try to pronounce it as a single letter.

UPDATE: Further digging seems to validate that most modern screen readers do ignore pseudo elements. So, there's no doubt that this solution is promising. However, as with anything, your user agent baseline should be considered before using it. Saying that everyone should be using this right now probably isn't a reliable blanket recommendation.

I'm a solo founder and have been working on Sifter (http://sifterapp.com) for going on 4 years now. It's been live for about 3 of those years, and I've been full-time for a little over a year. My salary is about 80% of what I was making working full-time elsewhere, maybe a little lower when you factor in health insurance, but the work is exponentially more fulfilling. I do my best to share my thoughts on the ups and downs on my blog. (http://garrettdimon.com)

I technically have what some people might consider a co-founder, but he's more of an investor/advisor as I've been the only person that's involved day-to-day.

I also created a presentation recently that summarized what the experience has been like and what we've done right or wrong for our situation. (http://bootstrapping.sifterapp.com)

Finally, I'd also recommend Maciej Ceglowski of Pinboard as a good source. He discusses a little bit of his experience on the Pinboard blog. (http://blog.pinboard.in/)

I hear you, but that's way outside of the scope of this post. Every single bullet point here could almost be a post in and of itself. The logic is pretty straightforward. With subscription apps, the likelihood of seeing money from that customer next month is pretty high. With a native app, the likelihood of seeing money from that customer next month is almost zero.

Keeping churn low has way too many potential variables. The quality of the product, the benefits or usefulness, the cost, customer support, and dozens of other things all ultimately play a role. Even the type of product could affect churn. Is it something that people only need occasionally or something that they'd use daily?

I honestly couldn't tell you how our churn manages to stay so low. If I had to guess, I'd say that it's focusing on making a high quality product and taking extremely good care of customers. We've never had someone tell us that they were canceling because of the quality of the product or support.

FusionAds, Daring Fireball RSS sponsorhip, RailsCasts, Dribbble, and a variety of other spots. In terms of ROI, we weren't really measuring things in that great of detail. We just used Google Analytics to understand the quality of the traffic.

The rates and returns were all over the board. The only consistent factor was that once Sifter became more well known, the advertising was significantly less effective at generating advertising. So, it's great for finding new traffic and getting the word out, but once that's done, we'd have throw a lot of money at it to see significant results.

We chose it simply because it was just an area that I'm oddly fascinated by. Our main channel for new customers these days is word-of-mouth referrals.

As far as the biggest lessons, they're all in the slide deck. :)

We haven't really done much with freelancers. Some of the design work and a little bit of development was outsourced to friends that we already had relationships with. These days we have a sys admin and bookkeeper on retainer so they help a little bit every month, but for the most part, we keep all of the work in house.

I don't really have any tips or advice beyond making sure that you meet people and build the relationships long before you need them. Then, you have people that you trust that you can turn to when you're ready.

Those are definitely all very good points. Everyone's situation is so different, I'm always hesitate to give any advice as a "prescription" and more of "here's what we did and why we did it so you can decide for yourself".

I'm definitely aware of how easily the new services enable you to entirely avoid the PCI issues. Personally, I'd say that their cut is probably well worth it relative to the time and effort that it takes to build it from scratch. However, that's driven in large part because I'd much rather invest time in the product than worry about the billing details. It's not that it's all that difficult, it's just that it's not the core of what makes Sifter unique.

With regards to promotions and stuff, I'm not a big fan of that. I'm a strong believer in keeping things simple and people either like it enough to pay for it or they don't. I feel that promotions might attract people for the wrong reasons. The more complex the pricing is, the more painful it is to deal with, and it can quickly become a distraction from simply crafting a better product.

Of course, plenty of companies have had great success with promotions, but it's not for us. To each their own, right? Either way, I hope the info helps. Best of luck which ever way ends up working out for you.

I don't think that we've added anything that we should have omitted, but I definitely think we added them before we probably should have.

Keep in mind that it really all depends on your goals, and my goals aren't to create a huge app that generates millions but to build something that's pleasant to use and supports me to the point that I can continue to work on it.

That said, I think that we probably should have invested in improving and polishing our existing features before adding source control and email integration. However, I'm sure those have generated a handful new customers that otherwise probably wouldn't have used Sifter. I think they fall into the categories of things that people need when they're evaluating software but that in reality they really don't end up using.

Really, there's so many variables that it's hard to contribute any level of success or failure to one decision. I'm really pretty happy with everything that we have or haven't done to this point. It's just a bit disappointing to pour effort into a feature and find out that it's only being used 2-3% of the time.

Cash flow is definitely a big part of it. With daily billing, we never see any huge fluctuations in our account. In my opinion, a slow and steady stream of income is much better than big pop once a month.

We went with Rackspace's Cloud Servers. We're using their load balancers with a couple of app servers, a background processing/search indexing server, and 2 database servers for a master/slave setup.

The main reason that I don't personally believe it's a good idea is that it's not a core part of Sifter. We use Braintree and process everything via ActiveMerchant, but we've been using Braintree so long that we're actually on their old API.

Obviously, since we built it in house, I don't have any hands on experience with the other options that are out there now, but from what I've seen with other applications, I can't see any reason not to use the other providers.

The downside to not building your own system is that you may lose some control over things like invoice formatting or other parts of the user experience.

The other aspect that's a big consideration is PCI compliance. We don't store any payment information on our servers, but it does pass through our servers which means we have to have the minimum amount of PCI compliance. By offloading it to another provider, you're almost entirely free of any significant PCI compliance.

Now that it's done, it's kind of nice having full control over every detail of how we handle credit cards. However, I wouldn't do it again now that there are so many other options out there.

Because the two smallest plans, while having high turnover, have also ultimately generated 65% of our revenue. So at this point, they're still a very important part of our customer base.

As far as only offering one plan, it simply doesn't make sense for us. Our costs go up based on the amount of usage, so it makes sense for the price to go up for customers who use more resources.

Our billing runs daily and charges each customer once every 30 days based on when they originally signed up for a paying account.

So each night, we bill about 1/30th of our customers. It's not exactly 1/30th because some days have more customers and some have fewer.

I'll give it some thought, but I've always failed miserably at trying to do that. I'm thinking it's easier/more efficient for everyone if focus on answering questions.

It's a feature within Sifter. Here's a few blog posts that go over the details.

http://journal.sifterapp.com/blog/2007/08/bug-issue-tracking...

http://journal.sifterapp.com/blog/2007/08/tracker-status-com...

http://journal.sifterapp.com/blog/2011/07/resolved-vs-closed...

Gotcha. I passed it along. I'm sure they'll get it sorted soon. If you'd really like it now, shoot me an email, and I'll send it along. garrett at nextupdate dot com.

The fraud was someone that was using us to validate stolen credit cards. They ran about 100 test transactions before we could lock it down. It took a while because we didn't want to detrimentally affect our customers just to stop it. So, it cost us some money in transaction fees, but beyond that, it wasn't a big deal.

As far as the transitions, it was partially cost and having extra cash and partially just being ready for it based on growing traffic or new functionality. It was never the same set of motivations. Fortunately, we never grew so fast that we didn't have time to scale with the growth. So, it was a combination of "things are slowing down a bit" and "we have the money to take the next step" and "we ought to have a better hosting environment".

Every day. In my mind, it will never be good enough. I've found that the philosophy that has worked best for me is that if you're not embarrassed, you've waited to long to launch. (I believe Matt Mullenweg said that, but I've heard it so many places now, I'm not 100% sure.)

I'll followup with the SpeakerDeck folks. I expect they'll have it working soon. I think they got slammed a bit more than they expected, but they're throwing more resources at it now.

I generally worry a lot less these days. There are other people involved now as well, including a sys admin on retainer, and it's been a huge change. I'm probably more neurotic about it than most people, and definitely more neurotic than I needed to be.

The reality is that Sifter almost never goes down, and when it does, it's usually something outside of our control and gets resolved fairly quickly by our host. Now that we're in a higher availability environment, that's helping a lot too.

The outlook is pretty great now. It was definitely hard at the beginning, but most of that was self-imposed. Now that I recognize how rarely Sifter does go down or have performance issues, I know that I don't need to worry as much. It was a difficult lesson to learn though.

Slides obviously miss a lot of context if you didn't attend the presentation, so I'd love to chat with folks or answer questions if anybody has them.

Thanks for the recommendation. Unfortunately, we've been with Braintree so long that we're on their original platform, and the gem only works with the new platform.

The migration to get on the new platform wasn't worth it for us right now. It definitely looks nicer, though, and I'm a little envious of those that signed up later and get to use it.

We use Braintree's vault, and we use ActiveMerchant to access it. We wrote all of the recurring/billing/invoicing logic ourselves. Beyond the initial implementation, we've done one sweeping overhaul of the logic to make some improvements and simplify things after learning a lot from the first pass.

We built it in late 2008, and either the companies that handled recurring stuff didn't exist when we were building it, or we weren't aware of the ones that did. Otherwise, it's unlikely that we would have gone down this route. However, now that we have it, it is pretty nice to have control over every detail of how it works.

When we made the enhancements, we briefly considered switching to a provider for handling it, but given our existing infrastructure, it was actually easier for us to improve our own instead of migrating to another provider.

For me, this approach is far more impressive than any story about a founder giving up years of his or her life to flip the company for a huge payout.

What you've described is what I aspire to once we have children. Working from home. Flexibility to spend time with family. Thanks for sharing.