Don’t forget, there’s a blog post for each episode too!
Great episode from start to finish, but I have to admit that my favorite part is where @RosemaryOrchard tells Dr. Drang that he shows up higher than John Lennon in a Duck Duck Go search for “and now it’s all this.” You can’t automate entertainment like that.
Since I listened to this episode, I’ve been meaning to come back here to just add a note that, although these automations for invoicing and follow-up etc are all really impressive and useful, and obviously do exactly what is needed (no more, no less), it sounds like they were all set up some time ago and the capabilities of existing software solutions may have seriously improved since then.
Obviously “if it’s not broken, don’t fix it”, but I would suggest to anyone looking to set up similar systems to investigate the options that are already available them in terms of accounting software.
I’m an accountant in Australia so my experience is mostly limited to software packages that we have available here, but I’m fairly certain that some of these–Xero comes to mind–are available in the US and possibly other places as well. And I’m sure there are equivalent products available around the world as Australia are rarely the first to have anything! 
Many of the software packages I work with have automation capabilities, though until I listened to this episode I had never really framed them in those terms in my own mind. For example, all of the following are common:
- Automatic import and categorisation or matching of bank transactions based on rules you set up or invoices/bills you already have in your accounting system. (These are usually subject to approval so it just speeds up that data entry.)
- Automatic (or semi-automatic) bank reconciliation based on the above.
- Sending automatic invoice reminders (including the ability to see if customers have seen the invoices, to allow them to pay online and automatically account for the payment)
- Setting up repeating invoices or other transactions
- Bulk sending of invoices
- Assigning expenses to a customer when you enter the expense and then prompting you to charge them onto the customer when you invoice them
- Batch payments for bills/payroll
Of course most of these are online now too, which has the advantage of the accountant having always-current access to your file. (One less thing to do every quarter/year/however often.)
Something like Xero also has a huge number of third-party integrations (I’m fairly certain it connects to Zapier, for example) which, although I haven’t had much experience with them, open up even more possibilities for automation (as well as other things).
But basically the point I wanted to make is that if you run your own business, these tools are worth a) looking into if you’re doing everything manually or struggling with a cobbled-together system of some kind and b) getting set up correctly and then exploring to see what possibilities for automation you might be able to open up just by using the tools they already give you, and not having to build your own solution. Of course, that’s always a possibility too if you find that they don’t quite serve your needs.