"should you wait until you've generated $1 million worth of revenue before starting to automate your business?

I disagree.  

I would start using automation early in a business, in particular an online business, selectively by:

  1. Automating email marketing efforts, i.e. - create autoresponders for people that have signed up for something from your site 

  2. Appointment scheduling of sales calls

I would still do the manual version of those, i.e. - send out a personalized or broadcast message, take an impromptu sales call.

Additionally, some examples of "semi-automation" that I use:

  1. Someone makes a purchase and I get a notification in Slack in real time.  Sometimes, I will make a personal thank you video and send it to the customer within minutes of the order being placed.

  2. Someone fills out an application and the contact is added to our email system along with their answers.  I have an automation that notifies me at 8AM the next morning, I review their application and reply back with a templated yes / maybe / no email that I modify before sending.

  3. Someone purchases a particular service of ours, they are put into an automation that notifies me on Monday at 8AM.  I open an SOP doc for purchasing a book on Amazon, filling out a gift card and shipping it to them.  I take the expected delivery date and update the contact's record.  That update kicks off an automation that sends them an email the day after they are expected to received the book.

  4. I have a sales call for a particular service that we provide, I have a list of questions that I ask. The answers get input to an online form.  When I submit, the form returns content for a price / time quote based on their answers.  This output is a proposal that I then copy / paste into an email.