Founder of Small Potatoes, which I started in my underwear as a Freelancer / Stay-At-Home-Dad that has evolved to supporting over 500 customers. I'm passionately interested in helping you do the same.
Another idea is to repurpose your old content into fresh, new content. If you've got a series of related, older posts, consider putting those into some sort of downloadable pdf (in exchange for email ) that your readers can take with them and then link to the old posts in that PDF.
If you're creating a 'how-to' guide and using older posts as some of the content, make sure to link directly to those posts in the PDF. Head over to http://blog.hubspot.com/ for awesome examples of this in production.
Assuming you're running WordPress, you should explore the plugin called Insights from Vladimir Prelovac ( http://www.prelovac.com/vladimir/wordpress-plugins/insights ) to help you connect with older content and media, as well as SEO Smart Links ( http://www.prelovac.com/vladimir/wordpress-plugins/seo-smart-links ) to help you automatically interlink older posts.
A third option is to fire up Adwords and build a campaign around your old posts. If you're doing this, then ensure that you're funneling those paid-for clicks from Google > Old Posts > call to action to New Post / Subscriber. Capturing new visitors and showing them your great archived posts, then pushing them to new ones has been quite effective for our customers and encouraging engagement.
You're not the only one confused., though I'm certainly interested to learn some more. If you're interested we can jump on a complimentary 30 minute call to see if we can clarify things a bit for you.
There is so much more to this than simply looking at implementation and cost. Honestly, any number of recurring providers are going to be fairly straight-forward for a quality developer to implement with your service. Many of them will also likely be easy enough that you can implement without a developer using third party API tools like Zapier.
My Disclaimer
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I run a recurring business. Every customer pays monthly. We have one trial available, and the rest are basically monthly payments. We run Stripe to actually process the payments and deposit into our bank account, and we use Chargify to handle the recurring side of things.
Stripe can handle recurring on its own, but it's not as robust ( out of the box that is ) as Chargify - and I like the reporting and maintenance piece Chargify provides.
We have 500ish customers and plans ranging from $150/mo - $2500/mo.
What to Consider
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1) You need to understand what you need
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If you simply need a way to process credit cards online as a recurring setup, then yes, Stripe can handle that. You set it up yourself ( or hire a developer ) and just connect it to your bank account. Create your product and really that's it.
If you require more functionality like HTML / PDF statements for customers, customer portal and account management, automated Dunning process for collections and your accounts receivables ( when customer cards expire, they reach their credit limits, their bank declines charges, etc.. ), refund processing, chargeback support, upgrades / downgrades, proration, etc.., you're going to be looking at some more advanced ( and expensive ) solutions.
2) You need to understand what you get
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One of the most important things to consider is data portability. You're a startup, and it's likely you're not going to be with the first solution you choose for the long-haul. Right now, you're going for what fits the business and what you can affordably scale as you need to. Eventually you may want to move to another provider.
There are currently no regulatory requirements for payment processors to provide you with your data. What this means is that in 3 years when you want to switch, you many not be able to access your customer data and port that over to your new solution.
Imagine the nightmare you are going to have when you've got 300 customers that you have to ask to re-join your services because you don't have their credit card numbers anymore. I went through it with just 45 customers and it was a terrible experience on both ends.
PayPal is notorious for making this difficult, as is Authorize.net - they are probably the worst offenders. So read through the agreements and terms and make sure you can take your data with you whenever you need it.
3) What are the fees associated?
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You're going to be dinged multiple times - by the merchant account, by the payment gateway, and by the recurring system.
If you just used Stripe, you will be charged ~ $.66 per transaction each month with your current pricing. Not bad, but it needs to be priced into your services and planned for. If you add some subscription software like Chargify, you'll be charged monthly per customer count rather than per transaction, starting at $65/mo.
So Customer 1 costs you $65.66 per month to process their card using Stripe and Chargify. So the pricing is certainly a big factor.
4) Is this self hosted or not?
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Are you going to host the payment forms, or outsource that to your gateway / processor. Stripe is wonderful because you dictate the experience and customers don't have to leave your site in order to process their payments.
However, this also means you need a secure domain or payment page with a SSL certificate. These range from $10/yr to thousands ( you likely only need the $10 cert for now.. ).
In order to have a certificate you also need a dedicated IP address. That will cost you monthly as well ( shouldn't be more than $10/mo for that ), so now our Customer 1 costs you about $77 this month in just processing their card.
If you decide to use the processor hosted page you won't need SSL or the IP address, and this works like PayPal does - customer clicks to buy and is redirected to payment page.
5) Understand the Support and Uptime
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The last thing you need are payment processing problems. Whichever provider you look at, ask them for their uptime history and understand what type of support you get.
Some processors provide 24x7 support, but only for priority customers. Some provide general email / ticket support, so you just wait in line.
Put yourself in your customer's shoes and ask what you'd do if there were a payment problem ( billed multiple times, not billed at all, not sure if you're billed.. ) and then figure out how you'd resolve those issues from your provider side. Ensure your gateway / processor support aligns with your own.
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I hope this helps you a bit. Here are some links to get you started:
Stripe - https://stripe.com/
Chargify - https://chargify.com/
Braintree - https://www.braintreepayments.com/
Recurly - https://recurly.com/
PCI Compliancy - https://www.pcisecuritystandards.org/
If you have any other questions or want some clarification on something, feel free to request a complimentary call.
Head over to wixia.com and watch some of their videos and resources. They have some really great ideas around this.
I'm not expert in this particular field, but I am an expert consumer, and if mentaltherapy is just so much easier to digest - and spell - than psychotao. You've got too much selling to do just to tell me what the site is about.
Mentaltherapy is quite clear.
I started providing email services for my web design customers when I started to build our small agency. We wanted to test the idea of providing those services to our current customers, and at that time I really didn't understand how to code HTML emails, nor did I have the resources to outsource this work as a full campaign or services offering.
I wanted custom templates but couldn't customize the ones from the mailchimps of the world, so I went looking for software that was more or less drag and drop.
I've tried almost everything (on Mac) an found that Direct Mail is the best. DM allows you to easily create HTML emails without touching code. You can test across browsers as well as devices, and they have their own mail server that you can use for delivery / tracking.
Also included are customizable signup forms for your website that will populate your lists & custom DNS options for more branded setups.
DM also comes pre-loaded with lots of templates to get you started & they've provided great support in my experience.
We started using their complete package (software and delivery), then move onto our own setup with SendGrid. We still use DM from time to time, and even for seasoned developers it will be a great tool for your belt.
Check out Direct Mail here: http://directmailmac.com/
I'd be happy to jump on a call and help you to define a best solution for your group at no charge.