216 FS Automation

00:00 01:02:54
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02:14 - Why automate? Are there cases where you shouldn’t automate?

12:29 - Templates

15:26 - Figuring Out What to Automate and Delegate

26:17 - Creating Benefits; Not False Improvements with Automation

28:35 - Automation Wins

36:58 - Getting Started With Automation

48:30 - Chuck’s Eliminations

52:22 - Tools For Automation



CHUCK: It’s weird not having anyone to yell at.

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CHUCK: Hey everybody and welcome to episode 216 of The Freelancers’ Show. This week on our panel we have Philip Morgan.

PHILIP: Hello, hello.

CHUCK: Reuven Lerner.

REUVEN: Hi everyone.

CHUCK: I’m Charles Max Wood from DevChat.tv. And this we’re going to be talking about automation. So the rest of this episode will be completely automated.

PHILIP: [Chuckles] We’re just going to randomly cut and splice stuff from previous episodes.

CHUCK: There we go. Yeah, you get me saying enough words and then you just – yeah. “I am such an idiot”.


REUVEN: If [inaudible] machine learning, this is machine podcast.

CHUCK: That’s right. So this is something that I brought up because it’s something that I've been doing a lot of lately is just working on automating a lot of things that I’m doing. It’s interesting – I want to start with why because both of you sounded interested in discussing the topic and I’m curious what idea you have of automation and what it’ll get you before we get into some of the things that at least I’m doing.

PHILIP: I find automation incredibly sexy and easy to misapply, at least in my own business, or prematurely apply. It’s related to the idea of premature optimization. So I actually am both in favor and against automation and other forms of optimization just depending on the context. I’ll be glad to elaborate on that, but at least for me there's been a life cycle of initial enthusiasm about the idea of “let’s automate this, let’s automate this”.

And when I say this, it could be anything. It could be marketing, it could be client onboarding, it could be any number of things. And then there's actually doing it – doing the automation, and then there's a kind of assessment of whether it was worth it. And I find that not every time it was it worth it. Not every time did it deliver an improvement. And so I guess that’s where I’m coming from was respect to automation.

REUVEN: For me, I have some automation set up in the sense of my email courses, and I’m really happy with that, and like when someone buys my books. So I’m really happy with that, but I know that I’m just scratching the very very very tip of the iceberg scratching the surface there, that I could be doing more and could be doing it better and I could be – well, I mean automating that could basically be having my business run itself and not have me need to deal with it all the time for some of the more mundane tasks.

And yet, it’s not always obvious to me how to choose what to do – well, it’s not all. I should say it’s not always; it’s not all obvious to me how to choose what to automate, how to automate it, and what things maybe don’t deserve to be automated.

CHUCK: That’s interesting. Ok. It was interesting. One thing that got me started on this was I listened to an episode of the Eventual Millionaire by Jaime Tardy and she had Rory Vaden on and he has the book Procrastinate on Purpose, and in the book which I read for part of my Mastermind group, he talks a lot about the process of automating stuff, but the first thing to do is not automate. The first thing to do is actually to eliminate, which is kind of interesting. “What can I stop doing that I am doing that I shouldn’t be doing?” and that’s very educational for me, but then once I started looking at “ok, if I can’t eliminate it, then what can I automate? What should I be looking at making more automatic, more” – I don’t know what the right word is, but just make it so that I don’t have to think about it and it just happens.

PHILIP: I work with a lot of new business owners, people who are trying to move out of – they're just trying to level up. That’s part of what makes people interested in the idea of positioning and narrowing down, and also work with a lot of people who have ridden a wave of referrals and good luck and see the end of that phase of their business and ready to actually start marketing for real. And through that, I've developed a philosophy that you should not automate something that you could learn more from; or to put it another way, something where you're still in that steep part of the learning curve and it hasn’t really tapered off. That’s not a candidate in your business for automation.

So great example is you'll see a lot of blog posts that talk about automating client onboarding or automating qualifying leads – that kind of thing. And as the – like a new business owner, that sounds so sexy. I think what's sexy about it is the idea of having like a – so many leads coming in that you have to automate it. But we kind of get caught up in the idea – wrapped up in this idea that “yes, I need to automate that”. That was something that at least for me, that was very appealing. And I think you miss opportunities to learn what your market is really like and what your clients really need when you automate away things like conversations.

So Chuck, you were like “what do you automate, what don’t you automate”, and I think I would at least throw out there that if there's something that you could learn that has real value for your business, don’t automate it. And I think that’s also why that there's this common advice in the startup world to do things that don’t scale. I think it’s the same kind of idea that by doing those things manually, you will learn something that you would miss out on if you automated it.

CHUCK: I think that’s interesting that you went to that first because that is one of the things that I’m working on automating right now; not client onboarding, but podcast guest onboarding. And it’s interesting, and I actually had a conversation with Mandy and we discussed the pros and cons of automating it versus having her do it or having a person do it, and there are definite upsides and downsides, and it wasn’t 100% there's no value in having a person do it, and it wasn’t 100% let’s not automate this and save some effort on some of the more repeatable parts of it either.

And so it was really interesting to come into the middle of that where it’s yes, it helps the guest feel like there's somebody there they can reach out to, and is there a way we can automate it that gets people some of that, as well as how much value is there in having somebody get in an hold somebody’s hand and work through getting them on board and on and on and on, and how much of that can you really actually automate where you send them all the information they need, start the conversation online, maybe take a few more steps in it and have all of that completely automated and then set them up with the conversation if it needs to happen.

PHILIP: Right. And this is something I believe that changes as the business matures. As the business matures, maybe they do have that tidal wave of leads coming in, or in this case tidal wave of podcast guests and it just makes sense to automate it because that’s no longer a high-value activity that you're learning a lot from. So all I’m really arguing against is premature automation, but I think that’s one way to decide whether you're ready yet is are you still learning really valuable stuff from doing this process manually. If not, then it’s probably time to think about automating it. It sounds like that’s where you're at with the podcast guest onboarding.

CHUCK: Yeah, that’s basically where I've come down is – yeah, most of the conversation will later happen on the show or the conversation will happen because they have a question about something and it makes it very clear, or the automation makes it feel like there's a person on the other end that you just hit reply and email and then you – it’s like “ok, so I need to do this and not that”. But yeah, for the most part, podcast guest onboarding is – we've got it down to a science now. And so 90%, 99% of the people coming in, they're just going to do what we tell them and it’s all going to work.

PHILIP: It’s very easy that if you roll back though to launch a podcast a month ago and you're onboarding a bunch of guests, it’s very easy to imagine in your head how that process you think should go and then design an automated system around that, and then find that that’s not a good fit for how the process actually should go, and that’s really the value doing it manually is that you learn at the ground level how things really work.

REUVEN: Philip, it’s interesting you say this. I guess it’s a little meta, but I know that when Rob Walling was setting up Drip, I remember listening to the podcast for Startups For the Rest of Us, and I think it was on Drip that he said they did not automate credit cards right away. They wanted to know who’s going to pay what and how much, and so they did it manually; also because you need to choose what you're going to work on first. And he decided “actually, we can just call people and deal with it”. I think do it through Paypal. And only a little down the road did they actually automate the credit card usage.

And I thought that was actually very clever, in part because it forces you to talk to your clients, exactly what you're saying, find out what they're doing, how they're doing, and then make the system appropriate for them.

PHILIP: Yeah. I know we’re talking about two different things here; one, like client work, and then the other more of a business process that’s kind of an internal process. But in general, I think that in those early stages, you just can’t talk to your clients too much and automation can really be an excuse to not talk to your clients. You think you're doing it to make your business better, but it in reality I wonder if it doesn’t harm a business to misapply automation. I know it does. Bill Gates said it does.

Bill Gates said you automate a – I forget the exact wording, but automation applied to an efficient business process makes it better and automation applied to an ineffective business process actually makes it worse. The idea has been around for a while.

CHUCK: Yup. Yeah, but at the same time, I can see if you have a set of ways that you operate or something like that, then I could see for example that you do a call, you finalize the sale, you have a discussion about how the contract’s going to work, and then you automate certain things to go out to them where you had the conversation and just by way of a reminder, “these are the things we discussed today”, and it’s “hey look, this is how the contract works”, and so there are things that you’ve already had the conversation about, but then it’s a reminder, it’s a follow-up; it’s some of these other things that can actually enhance the conversation instead of hurt conversations.

So I can also see that a partial automation of the parts that make the conversation richer, better, or more – sink in better may pay off. In another cases, maybe you have to have a conversation three times in order for it to really work out – I don’t know.

PHILIP: That’s a good point. I think the first step towards automation is templates. That’s the first step from completely manual, custom every time, to getting closer to having some of the efficiencies of automation.


REUVEN: [Inaudible] about templates, but do you mean like email templates or just like a standardized plan of action that you use whenever you have a new client?

PHILIP: I think [crosstalk]. Right, I would call the second one a process, but yeah, just templates like back to Chuck’s example, a template for “here’s what you need to know before you're a guest on The Freelancers’ Show” or the client services example. “Here is a template that describes how we do our weekly meeting or daily stand up” or whatever, stuff like that.

And I think that happens naturally; I’m just calling it out that that’s probably the first baby step towards automation.

CHUCK: The other thing that I see is that if you're talking about a process, it’s like “what are the things that we do every time?” So for example, onboarding podcast guests, we get them on a calendar. And we email them a certain amount of time before the show and we email them with all of the co-hosts so that we can have a conversation about what we’re going to talk about and they can give us materials to review and things like that.

And so since these are all things that have to happen – we give them information to connect with me on Skype since I’m usually the one that brings them into the channel – all of those things are a standard set of instructions that all of them are going to have to have, and automating that to the next level where we maybe send them to Calendly or we send them to a form where they can give us more information about themself or we go look them up on Linkedin and have them send us a link to Linkedin, or whatever it is that we do during the process. We can automate a lot of that where it’s “oh hey, looks like we got you scheduled on the calendar. Here’s the next step. Give us your profile” or “here's the next step. Give us information about what we’re talking about”.

So if you have that step-by-step process to work through, then you can start looking at those things and saying “ok, well that step is easily automatable and it simplifies this process so we’re only communicating about the things that we have to communicate about instead of discussing calendars and discussing this and discussing that, discussing the other thing”.

And then I like to include some way of reaching out [inaudible]. For example, we usually record this show on Tuesdays at 11:30 AM Mountain time. And so if that doesn’t work for somebody, they have something going on every Tuesday at that time, then the Calendly system actually says “pick the date that’ll work for you, and then if none of these dates work for you, then email chuck@devchat.tv and we’ll figure something out”. And so gives people that way around if they need it.


CHUCK: But for most people, why wrangle over calendar dates? Just use Calendly. And then we can talk about what the show is about and have that conversation and make sure that we’re focused on putting on a great show instead of when it is.

REUVEN: So, just in hearing what you're saying, I think part of my problem in trying to figure out what to automate is that I have so few standardized processes in my work. With the training work which is the majority of it, it’s – I guess it’s standardized in the fact that I send emails. Clients call me, I say “oh sure, let’s do it”, and we put it on a calendar and we’re basically done, or I email, and in the case of some big companies, I email them a proposal and they say “ok, it’s done”. And I don’t see how I could automate that.

Although I’m thinking maybe students who participate in the class, I could automate how I deal with them instead of manually having the – find or remember their email messages and so forth – the specific date before the course starts. But in my consulting work, I have no standardized process other than talk to them on the phone, and maybe that’s the first thing I need to do – really figure out how do I want to work with people, because I’m seeing more and more as my time is pressed and rare and I’m sort of forcing clients to talk to me in certain ways at certain times. They're ok with that. If I say “I can meet with you on the following days the following times”, they're ok with that. So [inaudible] are automated process actually would be a good thing to do. Having a process would be good, and automating it would be even better.

CHUCK: Yeah. One other thing to keep in mind is if there is a conversation or a task or something that you do for every client or every project – and the way to think about this is let’s say that it takes you 5 minutes everyday, 5 minutes every workday – let’s say you work 5 days a week and you work 50 weeks a year, so that’s – I think it’s like 525 minutes or something over the course of the year. If you can set up an automation system and you spend 2 or 3 hours, so that’s 180 hours or 180 minutes setting something up to save you 525 over the course of the year, then it makes sense to do that.

And so if there's some kind of automation where you can set up a continuous integration, or you can automate meeting schedules every week, or anything that you spend time communicating about over and over and over again, or any processes or explanations that you have to put together where you can put it up on a page on your website and then refer them to that and say “a lot of people asked me about this, here’s the answer”, or things like that, you immediately start to gain some of that time back because you spend a half hour writing it and it saves you 5 minutes a day or 20 minutes a week writing that email every week or something and the multiplication of that time really adds up.

REUVEN: Chuck, you just like – I think that was an extremely insightful useful comment because as you're saying, I’m thinking “ok, what is something that I spend 5 minutes on, 10 minutes on, 20 minutes on every day, week or month?” and I started thinking about all the stuff, all the stuff that I put together for reports for my accountant for instance, and all the services I use – first, it’s Paypal. If I get payments on Paypal – well, I do get payments on Paypal, so I need to go to the Paypal website, download the latest report and everything, I can write – I have actually some programming abilities. I can write a program to use. I’m sure Paypal has an API, download them and email them automatically. That will be really easy to do and it will save me probably a good 10 or 15 minutes a month, and that works out to an hour a year or more.

CHUCK: Well, the other end of automation is delegation, and the thing is let’s say that it takes you 2 – it would take you 2 hours or 3 hours to write that program and you can pay somebody 5 bucks an hour to go do that for you once a month, and it takes [crosstalk] 5 minutes. So what you're paying then is you're paying them 25 cents or 50 cents a shot to go in and do that. Now, multiplying that out against your time, it’s actually way more effective to just pay somebody to go through the process of pulling it out and emailing it to your account.

And so automation doesn’t actually have to be programmed or Zapier or some other system that automatically does the work for you; sometimes it’s just making sure that somebody understands how to do it and then getting it off your plate.

REUVEN: Right, right. Very true.

PHILIP: I am just now warming up to the idea of that. I've hired people before for various tasks and lower-value assistant level stuff, and it seems fine. I don’t love managing people, but I have now actually started to put together a text file in probably my most used piece of software [inaudible] to start to identify things that when I do them, I have some awareness of like “well, I don’t need to do this. I'm not adding any unique value by doing this. I’m just doing a thing that needs to be done”, and I’m starting to build that list. Maybe it’ll be 6 months or more before I actually do anything with that, but that’s part of getting ready for that because I know that if I was to have somebody work for me as an assistant in any capacity, what I would do if I didn’t plan for it is the wrong thing. I would just start delegating stuff that is top of mind rather than is it really well thought out way to somehow make things better.

I’m also, Chuck, reading that book Procrastinate on Purpose. I’m just about to the point in the book where I think I’m about to get the punchline about what this whole idea of multiplication is, so thanks for that recommendation.

CHUCK: Yeah. And I didn’t really explain anything that he doesn’t go into in the book. And that’s the really fascinating thing is it’s like you think about it as like “well, it only takes me 5 minutes to do it”, but 5 minutes and 5 minutes and 5 minutes and 5 minutes and 5 minutes over the course of however many days that is really adds up.

And the thing that really got me to get behind this wasn’t just “oh, I could save all this time and then I could do all these other things”, but it was “why am I doing this?” So you couple this with Start with Why by Simon Sinek, and you start going “ok, so what kind of difference can I make? Who can I reach? Who can I touch?” and yeah, that’s the unique value that you have is the parts that are uniquely me and those things that are important to me in the way that I interact with and impact other people, and by doing this kind of multiplication, I can get that much more done for the people that I’m trying to serve. It’s not just “oh well, I like more time to go play Pokemon Go”; it’s “I would really like to spend more time with my kids and have an impact on them”, or “I could put together another email course that helps people with a particular problem in programming or careers”. And that’s where the money is for me. That’s where the payoff is “oh, I can make a difference for these people that I have chosen to serve”.

PHILIP: I just want to tag on to what you said because – I’m not disagreeing at all. You were like not more time to play Pokemon Go, but I’m starting to realize – give a short story that explains why, but I think I undervalue or have historically undervalued RNR and I’m starting to see that kind of fraying around the edges that happens when you do that. But it would probably be good for me to play a little more Pokemon Go.

CHUCK: Gotta catch them all.

PHILIP: Very frequently we’ll record something for a client or for a mentoring student. And sometimes I’ll listen back to those things where it’s like my recorded voice – maybe I’ll do a screencast to explain something.

And so there's been a couple of times where I will just listen back and detach myself a little [inaudible] I’m like “wow, that dude sounds exhausted” and I’m like “well, that dude’s me”. I think something needs to change, and I’m starting to look at doing less and delegating more as a way to facilitate that.

REUVEN: It’s fascinating that you say that because I know I need to sleep more. And just literally today, I told you guys before we start recording that my kids were all away this week in the Scouts camp, and so for the first time in a long time, I – there are no kids around so I can actually do some work and then go to sleep at a more normal hour. And so I think this is the first in a long time I've gotten 6, 8 hours of sleep at night for several days in a stretch. And my sister called me earlier today; she said “what's going on? You sound so well rested”. And I haven’t told her what was going on, and so clearly, while I don’t perceive it, other – especially others who know me well, do.

PHILIP: Reuven, I’m sorry to – sorry to jump in here. I’m starting to think of that ability to be well-rested and sharp at least for my own business as a competitive advantage that I feel like I’m missing out on because I’m running myself too hard.

CHUCK: Yeah. One thing that I’ll put in is as you read the book, he starts out with eliminate, and then automate, and then delegate, and then it’s procrastinate, and it’s “what do I” – so it’s not [inaudible] list, but it doesn’t have to be done now. “If I don’t start it now, is it going to blow up my life or my business?” And if the answer is no, then put it off.

And so maybe the most important thing you can do for your business is rest. Maybe the most important thing you can do for your business is think deeply about where you want it to go. Maybe the most important thing you can do for your business is consider how it impacts the other areas of your life that you care about so that you are getting everything you want out of it so that you can continue to do what you do. It just –

PHILIP: Well said.

CHUCK: So it’s not just – I think it takes a holistic view. And it’s life in general as well. So yeah, if I don’t spend time with my son now, then is he going to wind up being – it’s kind of an extreme example, but is he going to wind up being a criminal because he didn’t have a role model because I was stuck in here podcasting? And so I can prioritize that. I can say “ok, well now this is the most important thing that I can do”. And it’s building a relationship with my son so that I feel good about life so when I come back up here tomorrow, things are good.

PHILIP: Yeah. Yeah. Well said.

CHUCK: So yeah. It really just comes down to this. And just working through this and figuring out “ok, what is the number one most important thing?” And if it’s something that you don’t personally have to be involved in, then maybe the number one most important thing is making sure you're not involved with it going forward.

And then the number one important – most important thing related to that a few weeks from now is checking in to make sure that the system is working or finding a way to improve that. But for right now, getting it off your plate and making time for marketing or making time for family or making time for whatever – sleep – is the next most important thing you can do.

REUVEN: Very true.

PHILIP: There's another – I feel like there's an opportunity for us to dive deeper into where the big wins might be with automation. I feel like before we get [inaudible] still on this contrary track, I think it’s easy to make false improvements with automations so –

CHUCK: Oh, it’s totally fair.

PHILIP: It’s easy to say “ok, I – my inbox is just killing me. It’s so cluttered. I’m going to take this notification and I’m going to pipe it over to Slack instead of email”. And to me all you’ve done is just taking the pile sand and move – split it in two pieces and – but you still have to pay attention to that piece that you split off and moved into Slack.

So I just – I noticed at least in my own life that technology makes it very easy to say “oh, this is going to make things so easier”, but all you’ve really done is created another little pile of distraction and [inaudible] loaded into something else. And now you're context switching and not really gaining any benefit in terms of the things we’re trying to actually accomplish here. So I’m curious if anybody else sees that and – but that’s really not a big deal; just something I wanted to mention.

CHUCK: That’s fair. You're not changing the amount of work that you're doing in the case that you're talking about. So the multiplication effect on your time doesn’t occur.

PHILIP: And I guess that’s really the point here is like how can you use automation to create some kind of significant benefit.

CHUCK: Well I think you do have to do that return on investment analysis. You have to look at it and say “ok, what is the payoff on this? What is the time savings or energy savings or whatever it is that you're measuring? What is the payoff on this?” It’s an investment, right? It’s like anything else that you're investing in – taking the time to automate stuff or delegate stuff or train somebody, it’s an investment for future time savings later on. And so just like if you're investing your money in the stock market or mutual funds or anything else, you want to take what information you have at your disposal and determine whether or not that’s an investment that’s going to pay or not.

REUVEN: Very interesting.

CHUCK: I’m should just recite the rest of the book to you guys.


REUVEN: Tonight’s show will be a dramatic reading.

PHILIP: [Chuckles] Well Chuck, what are then – I don’t know, say last year or last 6 months, whatever, some significant wins that automation has yielded for you or you expect it to?

CHUCK: One of the things that I pulled together was putting updates into Facebook. So I put together a Facebook page – I've had Facebook pages actually for a while, for DevChat.tv and for most of the shows, and I just never posted to them. And so I went in and I spent maybe an hour total getting things worked out and set up on Zapier to get those posted. And all of a sudden, I have people engaging with me or I’m engaging with the shows or the brand and saying “hey, why am I not seeing this on the DevChat.tv Facebook page?” or they come in and they start asking questions about some of the shows, or I get engagement from other places. And it was something that I just never remembered to do, and all of a sudden that’s working out to start having payoffs in other places.

Another area that has paid off is I’m using a system called unfollowers.com which works on Twitter. And basically what I’m doing with that – or one of the things that I’m doing with that is that it posts a message automatically to anybody who follows me, and it says “hey, are you a fan of the podcast, and have you heard about whatever conference is coming up in the Remote Conferences?” And I have gotten sales off of that because I’m letting people know. But the other thing is I've automated the creation and started several conversations on Twitter in the direct messages system. And so what I get from that is that I can then follow it up with “oh, how long have you been listening to The Freelancers’ Show, and which episodes have you liked, and where are you at in your career, and what can I help you with, and do you want to talk for 15 minutes on Skype and have you heard about some of the other things that I’m working on?” and I get some great stories from people and they make these personal connections, and it just works out really nicely.

One other area that I’ll briefly touch on – so I mentioned Zapier as a tool; zapier.com, and Zapier connects all kinds of stuff, which is really cool. Another tool that I’m using, and I've migrated the topics and guest suggestions over to Trello and to Gravity Forms on WordPress. And WordPress actually – so there's a plugin for Gravity Forms that allows you to connect Zapier to it. So if somebody submits a form on the website on DevChat.tv – so if you go to freelancersshow.com for example, you will see links. One is Suggest a Guest and the other one’s Suggest a Topic. And if you click on those, it takes you to a page with a form, you fill out the form, “please get this person on the show. I like hearing him talk about this stuff. Here’s their email address or Twitter or GitHub” or something – somewhere where we can reach out to him, and then the name of the person who requested it. And that goes into Trello.

And then recently, not so much on this show, but on Ruby Rogues and JavaScript Jabber in particular, we've had some of my co-hosts actually suggest 10 people that they wanted to get on the show, and then Mandy has actually just gone in and reached out to them. And so there was no “oh, Mandy please go talk to these people”. It was just she just did it. So she proactively took the next step and it went from an automation to a delegation, but the delegation was completely implicit.

And so as that work through, now I’m looking at it and I’m going “ok well, if somebody gets recommended, then what I’d like to do is I’d like to move the person over from suggest to either I know this person and I’d like to invite them to come on the show”. And so if I move it over to another column in Trello, I’m going to automate that so it sends them an email and says “hey, we’d like you to come on the show and talk about this thing, and then basically pick a time on Calendly, and then once they pick a time on Calendly, it’ll trigger another thing that goes through and says “great, we've got you on calendar for this date. Here’s how you connect to the call. Here are the guidelines we have for the call”, and then automate another set of emails like a week or two beforehand that says “hey, you're coming up in a week or two. We’re getting ready to talk to you. Here’s the topic that we discussed talking about, and can you send us some materials that you or others have put together that you’d like us to review before we talk”. And then that starts the email conversation.

I’d also like it to create a document in Google Docs where they can add that kind of stuff, we can get in, we can frame a lot of the conversation before we have the shows so we get an outline, and then that can actually be put in as show notes or be used as a resource for the show notes. And then email them like 3 days before and 1 day before, which is a quick reminder “if you haven’t added Chuck on Skype yet, please do it. Blah blah blah”. And so the whole process gets automated. And then at the end of it, it’s like “if you have any questions, just reply and let me know”.

And so they’ll all look like they were emailed from me. It’ll all get sent out through SendGrid, but that whole process can be worked through and I can write those emails so that they have a personal touch. I can set things up so that if I set up a certain field or have that parse the Trello body in a certain way, then I can put personal notes in there. So let’s say that’s it Ruby Rogues; we wanted to get James Edward Gray back on, granted all of this is hypothetical and stuff that I’m working on now, but let’s say we wanted to get James Edward Gray back on – he was on the show for a long time as a regular guest. So I could set that up, and so the first part is just any personal note that I want to say. So I’m like “hey, it’s been a long time since we talked”. I was out in Oklahoma where he lives for a while for a family vacation, but I really liked it there. “How’s your wife and kid?” all of that stuff, and I could put that in there as an opener formatted nicely and then it just slides it in there and then it says “I’m actually emailing you to see if you want to come on the show”, or “I’m actually emailing – this is a follow up to the last email” and so then it can just flow neatly and from the personal comments to the business of “hey, let’s get you on the show”.

And so I’m working on a lot of these steps so that I can have the personal touch, but I don’t have to figure out how to write that email every time, and I don’t have to copy and paste or do any of that other work. I just set it up so that I have a system that sends that out and still gives them that personal email. And then if they want to reply, the reply to email address is mine, so they just hit Reply, they email back “hey, the family is great, blah blah blah. Thanks for this. I got on Calendly and I signed up”. Does that make sense?


PHILIP: It does. And it sounds like a great example of automating stuff that there's nothing to learn there, there's no value add from having it being done the hard way manually.

CHUCK: And it allows me to personalize it to a certain extent without having to go through the whole process of “oh, what does that email say again?” or anything like that. It just – and if it’s somebody that I don’t have a personal relationship with that is an expert that is going to come on the show, then they just get the standard email. “Thank you for coming on. I really appreciate you taking the time. Here’s how we’re going to get you on the calendar. Again, thanks for coming on. Here’s how we’re going to communicate about what the show is about”.

REUVEN: Yeah. That sounds – how should I put this – it sounds like you really follow through the process. It’s clear you’ve thought this process really carefully, and there is a way for you to go from no process to process and from process to automation, and that’s really impressive.

CHUCK: Well, the thing is that –

REUVEN: And that’s good for everyone. It’s good for you and it’s good for the guest and it’s good for everyone.

CHUCK: Yeah. Well, the other thing is that this is something that we've been doing for 4 or 5 years, right? Since Ruby Rogues started 5 years and 2 something – 2 or 3 months ago. And so it’s something we've done over and over and over and over again so we know what the steps are. And so you're saying you’ve really thought through. Well, kind of, but we've done it so many times that the process is very well understood.

And the other thing is that if it’s something that you feel like you can’t get that time savings on and you feel like you understand the process enough to at least partially solve this problem, then partially solve the problem and then tweak it periodically when you think “oh, maybe it would work better if we do it that way”. It’s not a permanent thing. If I find something is left out of those instructions, then I’ll just add it in. But yeah, you're saying it’s well thought out, and I’m telling you we've done it over and over and over again and we very deeply understand the process here.

REUVEN: So what should people do if they're looking to automate – if they're looking to find these processes? I’m thinking now that one of the things I should do is keep better track of my time and see – so I could build an hourly – ha ha, Jonathan is not here this week [laughter] – keep better track of my time so that I’ll know what I’m spending time on because I can assure you that when I think I spend 5 or 10 minutes, I am actually spending 20 or 30 minutes on. And those things will add up even faster, and so those are better candidates. But if I can even put my finger on what those things are, it’s hard for me to know what to prioritize.

CHUCK: I think that’s actually a really really great way – place to start because I think you'll be surprised by “huh, I’m doing this like 6 times a day”. And you may say “ok, so I only need to check my email once a day instead of 6 times a day”, and so you eliminate it instead of automate it; or you may find “oh, there is this thing that I do 6 times a day, and I can have somebody else do that”, or “I could write a Ruby script in a half hour and that’s as much time as I spend in a day doing it. And so tomorrow I’ll just run the script”.

But yeah, I don’t know if you can know that without either already having a process in place for something that you’ve delegated and then work out a way to automate it, or by keeping track of what you're doing. And if you have other people working for you, you should probably have them do that too, like is there some part of their job that is boring or mundane or routine that they can do away with. Because the thing is that their time is your money too. And so if you can work things out so that you're saving them a time, you're saving them money or saving them effort, then they can also put that time toward the things that are important to you and they can make the right things to priorities for them instead of doing the stuff that they just wind up doing over and over and over again.

REUVEN: Mm-hm.

PHILIP: Observations – I think we operated under this mental model of like the business has two parts; it has the stuff that we like doing, which presumably creates value, and the annoying crap we don’t like doing, which really is an umbrella that covers a lot of things. I use to hate invoicing, for example, and that was under that umbrella of annoying crap that –

CHUCK: I bet you always like getting paid though.

PHILIP: I did [chuckles]. But in that simplified model, I think that model’s not quite accurate. I think that at least as I've matured – I hope matured in some way in my business – I've realized that I actually enjoy, even though I’m a big fan of focus in your marketing, in your value proposition, I’m actually a big fan of having some diversity in my day. So this idea that if I can just eliminate all that annoying crap, I would have more time to do the really important stuff. It doesn’t quite work that way because who can just sit down and do a thing for 8 hours? Maybe you can when you're in that flow state, but I think for most people that’s not the norm. And I don’t think it’s really necessarily because of the annoying crap; it’s just not – who can be in that flow state for 8 hours? You're going to get interruptions no matter what.

So that’s an observation [inaudible] perhaps of not much – but here's the bigger observation is I think the thing that creates value is often not what we think it is. And I think that takes time and introspection and experience to discover what that is. I remember a long time ago hearing that McDonald’s corporation is not a fastfood business; it is a real estate business. And I always thought that was just one of those urban myth type thing [inaudible]. While we’re talking here, I found some articles that actually back that up. They make a lot of their revenue from leasing or renting real estate to their franchisees. So to me, that’s an interesting example. And I think in your case Chuck, maybe it looks like your business is a podcasting business, but when I heard you talking, I got the sense that at least a part of it is a relationship business.

CHUCK: Oh, very much. Very much.

PHILIP: That’s what – if you invest your time in building those relationships, that might be one of the top one or two or three things you could do, whereas if you invest the same amount of time in – I don’t know – getting better audio quality, not that there's anything wrong with the audio quality, would that produce the same benefit in the same amount of time? Probably not.

So I think part of it is just understanding what really produces value so that you can prioritize, not just based on how much time things take, but how much value they add to the business. And I don’t think there's any framework for universally knowing what that is across all businesses. It really is just a question of having a bit of experience and trying different things and paying attention over time.

CHUCK: Yeah, definitely. But then there's even a step further into the rabbit hole that is “what am I doing that builds those relationships?” And we can get into the 80/20 rule. What is the 20% of what I’m doing that accounts for 80% of that relationship growth? And then cut the other 80% not because it’s not valuable, but because it’s not as valuable. And so the others stuff becomes the priority that you work on.

PHILIP: I know. And when I've first moved across that, I guess in Tim Ferriss’ is 4 Hour Workweek book, I was like “ah, that makes so much sense” that yes, and actually doing that analysis is way harder than anybody makes it seem. And I think that’s the – that’s part of maturing as a business is learning how to do those things. I don’t know any way to – that some book you can read that teaches you how to do that. I think it’s a little bit of learning your market, learning yourself, and just experience over time.

CHUCK: Yeah. But at the same time, if you think critically about it, the other thing is that – and what I mean by think critically about it is “ok, what would I need to know in order to make that decision or make that call?” Decide what that is.

PHILIP: Can you more about that?

CHUCK: For example, I have a whole bunch of information that I have gathered about the downloads. I know where people are at, I have statistics on who’s downloading the podcast and where they're from, similar with the website traffic. But then it’s like “ok, so who am I reaching, and what does that tell me?” Well, it tells me where they are, but that doesn’t tell me who they are.

And so it’s like “ok, well where do I get that information?” and this is something else that I've actually delegated and I’m just rounding out now, but then it’s like “ok, so what information do I need?” Well, I want demographic information about the people listening to the shows. “How old are you? How much money do you make? How big is the company you work for?” – that kind of thing. “Which shows do you listen to? What episodes have you liked? What are your interests? How can we – what topics can we cover that are going to make a difference?” and on and on and on.

And what that does is then I get this picture of the people who are listening to the show, and that helps me. Maybe the big thing on my list is getting better sponsors, or maybe the big thing on my list is getting better guests, or maybe the – so it’s like “ok, this relationship I have with my audience is best served by getting more relevant sponsors or our guests are top notch or they're high enough notch to where the big payoff is getting sponsors that are more relevant that solve their problems; or maybe it’s the other way around. Maybe the big payoff would be getting these high profile guests or growing the audience so we can get the high profile guests or whatever. And so I can look at that demographic data and I can say “ok, well then I need to be in the places where people of this demographic are”. And so I can start finding options and automating my way into that.

So maybe it’s “ok well, most of our listeners are between 20 and 30, so I’m not going to go on Facebook anymore; I’m going to go on Snapchat” or maybe I’m going to do this or that, and so I can automate things. I can put it into my schedule. I can take the steps to start working my way down the line and build those systems so that they pay off; or maybe I figure out “you know what, Facebook pages aren’t the way to go, or tweeting on Twitter is not the way to engage with these people”. And so I can eliminate those and focus on making the RSS feeds better or I can start another show that hits that demographic where they live or whatever, but all within the context of stuff that I’m already doing or already good at and I can double down on those areas that really pay off.

And the other part of this, I think, is just gut feel. So as I talk to more people, I talk to podcast listeners, I talk to the people around me, I talk to other podcasters in the space, I get a feeling for where the industry is. And I think it’s a mistake to discount your gut feel unless you have data that directly contradicts it. And even then you really need to think through it. And so again, so maybe instead of – or in addition to collecting all these information, I collect all the information, I digest it, and then I go do personal retreat like we talked to Sherry Walling about a few months ago, and I really think through it and process through it, and I think that’s just as important as well just figuring out and taking the time to get the space to figure out what it means to me, what it means to the business and how that gets me to where I want to be.

PHILIP: Yeah. And having the margin, the free time, to do that kind of deep thinking certainly could be enabled by automating some of these crappy stuff you don’t enjoy [inaudible].

CHUCK: Yup. And maybe it frees up time for me to do that in the morning for an hour, or maybe it frees up time for me to take a weekend off or whatever works for me; and same for you, whatever works for you. So maybe an hour in the morning is what you need, or maybe it’s not. Maybe it is something else. But again, what it does is it allows you to make that time the priority when it needs to be taken.

I've been thinking a lot about this lately [chuckles], but you can tell –

REUVEN: Yeah, no; very impressive.

PHILIP: That’s awesome. Yeah.

REUVEN: I just have lots of ideas now for where I should even start on this path, and as I said like putting together some of these processes, but I’m sure that once I see the patterns, then it’s going to be hard to stop me from automating things.

PHILIP: Watch out. Zapier pro plan, here we come.

CHUCK: I have one of them.

PHILIP: Me too.

REUVEN: I actually signed up for it because I needed it for a few things too. Although people told me for a long time that I should use Zapier. I was like “yeah, yeah, yeah. How much could it really do for me?” And I tried it and said “oh wow, this is very impressive”. So I know also there, I come to more to scratch the services of what I could do.

PHILIP: There's a whole other domain of automation that we could talk about from the marketing perspective. I almost feel like that’s a whole separate show because you got to – we've got to consider things like why are you automating it and will it be effective at building trust, and it’s almost more of a blended approach, probably deserves a more nuance separate discussion.

CHUCK: Yeah. There's a terrific book – I’m trying to remember – I think it’s Perry Marshall. It’s 80/20 marketing.

PHILIP: Yup. That’s the one.

CHUCK: And it is awesome. 80-20 Sales on Marketing by Perry Martial. Yup. That’s definitely another one that I recommend to people just from the standpoint of “ok, what should I keep doing? What should I quit doing? What's paying off here?” and he really does dig into that “look, there is some things in that 80% that are working for you, but there are things in the 20% that if you double down on them are going to work much better for you”. And he explains that and explains how to identify some of it, and it’s a tremendous book.

PHILIP: I’m curious, Chuck, at what you have eliminated. We didn’t really talk about that, but I think that if you can share a few things, that would might be interesting.

CHUCK: So one of the things that I've eliminated some of, not all of, is a lot of the email stuff. So I let off lot of email stuff slide. If I have time to answer it, then I will, but I time-box that. So I've eliminated checking my email more than once or maybe twice a day; same with Twitter, same with Facebook.

I’m working on finding other things I can eliminate. I have some things that definitely take up time in my life that I am debating whether or not to eliminate; things outside of the work, for example. So I've got some extra things that I do for Cub Scouts, and so I’m considering “ok, is this worth it to get some time back?” I’m on the school board for my kids’ school, so I've thought about eliminating some of that.

Just some of the other things that I do just for outreach, I've looked at it and it’s like “ok well, that’s not paying off”, so I quit doing it. But at the same time, I’m also trying to figure out “do I want to add things?” So it seems like people respond well to certain emails that I send out so I want to do more of that. And so it’s like “ok, how do I fit these things in and how do I move the other things out?” and I find that I've been forced to eliminate things over the years. And I don’t have any great examples of that, but I know that there are some things that I just wind up not doing because I don’t have time. And I think that comes down to procrastinate, so I just indefinitely procrastinate them.

But it’s really tricky. And the other thing is it’s like it’s not just time savings, but money savings and other areas where it’s like “hey, can I get this done for half the price or a quarter of the price, and what's the trade-off and is it worth it?” So there are tricky decisions to be made like that too. But yeah, I wish I had better examples of eliminating stuff. That’s one thing I’m not as good at.

REUVEN: Yeah. [Chuckles] I dream of the day when I can start to eliminate things because I just keep doing more and more and I keep thinking “well, how much time would this really take? And how much would that really take?” and then [inaudible] before really resonates with me which is everything takes some time, and so it’s eating away at the time that I could be doing other things.

CHUCK: Yeah. And the real trick there for me that I found is that I look at my list of things, and I've actually started making a list for the day and a list for the week. So this week, I had 7 things on my whiteboard, and those are the things that I’m getting done this week. And so I make each of those things the priority when I feel like I’m in the right frame of mind and the right – I have the time to do it. And then I just – if I don’t get it done, then I just move a little further down the week and move other stuff off the week so that I can get those things done. And I think by that process, I’m not necessarily deliberately eliminating things, but the other things just aren’t even close on the priority list and so they get – they don’t even make it on the list, and so they get eliminated just by virtue of the fact that it’s “ok, this morning I’m working on Rails clips videos, and this afternoon I’m working on the automation for onboarding people, and tomorrow I’m working on sponsorships”. And if you're not on one of those – the lists for one of those things, then you better be pretty darn important to be able to pre-empt it as the priority.

REUVEN: Right.

CHUCK: And so not having made a deliberate decision on very many things to eliminate them, they're just not making it onto the list and so they're getting procrastinated – or they're getting eliminated by default. But they may come up later. I don’t know.

But that’s the other thing I’m finding is that if I put it on a calendar and commit to that commitment, then things tend to work out pretty well.

PHILIP: Yeah. I would agree with that.

CHUCK: Alright, well I think there's more to say here. I’ll probably reach out to Rory Vaden and see if we can get him on the show. We just talked about the book straight out, but yeah – is there anything else either of you want to add before we go to picks?

REUVEN: We really mention [inaudible] beyond the scope, but shall we just mention some tools people use for automation? We mentioned Zapier, and I think all three of us use Drip as well.


REUVEN: Are there any other tools people should be looking at, considering?

CHUCK: There are a bunch of tools out there for WordPress if you're using WordPress. There are editorial calendars; you can actually schedule the release of blog posts and podcast episodes, in my case. There are plugins for all kinds of other things that allow you to schedule things and make things happen on particular timelines that relate to that. So I’m not going to go into all of them, but if you're on WordPress, there's a whole class of things that you can plugin there.

I mentioned Gravity Forms, so that plugins to Zapier, and that works out. The other thing is if something has an API, you can probably find a system that will connect to it and automate to it, so that’s just another thing to keep in mind.

PHILIP: I was trying to think about that question, Reuven, from the perspective of what are the automation tools I would take on to a desert island if I was limited to 2 or 3.

REUVEN: And a really good connectivity despite being on a desert island.

PHILIP: Yes, right. [Chuckles] Satellite with no latency or – anyway.

CHUCK: That would be a GPS in Skype, right? “Here I am. Come get me”.

PHILIP: [Chuckles] Yeah, exactly. A helicopter.

Certainly, Drip. Probably Calendly; Calendly for sure. If you just work in a cave and you talk to people like twice a week, the value of Calendly is not going to be there for you. But if you're like me and you're interacting with a lot of people, Calendly for sure.

CHUCK: Or like me where you're scheduling 5 podcast guests potentially every week.

PHILIP: Right. Yes. And I guess probably Zapier just because it’s such a robust general purpose automation tool, but for sure those. [Crosstalk] Calendly and Drip.

CHUCK: One of the thing I’ll put out there is Google Docs just because if you can write up a process that somebody else can follow, you're halfway there to automation, and sure your automation to that point is somebody else is going to do this, but eventually you can figure out how to make the more time consuming and repeatable parts do themselves in a lot of cases. So yeah, just a word processor and the ability to show the documents. You can do that over Evernote or whatever as well. And then you can actually go in to Upwork and delegate things off to people that way.

And I’m also – one other thing that I find is Dropbox. That’s where I put all of the episodes so Mandy can edit them. That’s where I put videos for my video editor guy to edit them for the remote conferences and stuff. And yeah, a lot of that process is manual, but the fact that all I have to do is drag in over to another folder on my computer, and then once it synched up, tell Dropbox not to sync it to my computer anymore is super easy and super valuable.

Any others that you want to cover before we go to picks?

REUVEN: That was great.

CHUCK: There are also plugins for Gmail. I’ll mention that as well that I use. I use Boomerang and a few others that do stuff for me.

PHILIP: Yes. Streak CRM, which I think has been mentioned on this show before as a really nice Gmail plugin for not automating per se, but just tracking and managing information.

CHUCK: Yeah. A lot of CRMs actually have built in automation for a lot of things. And Drip does as well with the workflows and the tagging and all the stuff there too.

Alright, well let’s go ahead and get to some picks. Philip, do you have some picks for us?

PHILIP: I have a few picks this week. One tool I was saving for the picks is a tool for managing processes like procedures, standard operating procedures. It’s called Process Street, and it’s not like Trello, but it is like Trello in that it’s a SaaS, it’s web-based. I've used it before when I was doing more process-oriented work, and it’s kind of awesome. It lets you create these processes which are really just like a checklist, but if you have a team, you can create template processes that you then instantiate an instance for someone, assign it to them, and they go through and check things off and it’s more robust than just a checklist. It’s like you can include screenshots and descriptions of stuff. So it’s really aimed at people managing a team of other people who need to adhere to a set of processes. And it was kind of early days for that app when I first used it, but it’s still there. They still appear to be developing it, and so forth. And so it’s worth a look if you deal with a lot of SOPs and a team.

Second pick, I’ll just read that quote from Bill Gates. I think it’s pretty good and still accurate today. The quote is this: "The first rule of any technology used in a business is that automation applied to an efficient operation will magnify the efficiency. The second is that automation applied to an inefficient operation will magnify the inefficiency." So I guess I’m cherry picking here, but to me that points out that you need to do stuff the hard way manually at first, figure out what you want to automate and how you want to automate it before you start throwing automation at it.

I’ll throw in a link also to that Motley Fool article about how McDonald’s is – ha ha, surprise – actually a real estate business, not a hamburger business. And I’ll throw in a link to that 80/20 Sales and Marketing Book. I actually read a summary of it, so I haven’t read the whole book, but I found on Kindle, for like 4 bucks, you can get a summary of it. So if you're a [inaudible] for time because you're – you need to automate something that you haven’t figured out how to do it yet, you can read the summary instead of the full 300-page book and maybe that’ll get you started. So those are my picks for this week.

CHUCK: It is so good. Just go read it.

PHILIP: The whole case. That’s worth the whole thing – I wouldn’t know. I just read the summary, but [chuckles].

CHUCK: Ok. Reuven, what are your picks?

REUVEN: Ok. So I've got two picks. One of them is something that I've only started exploring very recently. It’s a site and also a podcast from this duo; they call themselves The Membership Guys. And they talk about membership websites and how to set them up and how did people pay for them. So I’m still just – I seem to be using this phrase a lot this episode – I’m still scratching the surface of it and learning about it, but it seems very interesting to look at, and they have a bunch of free things people can look at, a Facebook group, and they do webinars.

And actually in having a sign up for the webinar in the last few days, I saw that that was aactually highly automated and it gave me all sorts of ideas of the connection between signing up for that and what we discussed today. If you can automate webinars, then you can have this whole sequence kick in. I’m sure that I will get an email on a very regular basis over the next few days suggesting that I buy all sorts of things from them. And I of course having total resistance to brainwashing and marketing will go ahead and buy it anyway.

The other thing is I actually just started a Facebook group in the last day for people interested in doing technical training. So I'm starting to – as people, regular listeners know, I do a lot of training and I've started moving into helping others do training as well and learn about it. So the first step in my trying to help people learn both how to improve their teaching and how to learn about the business of training is to start this Facebook group. So I’ll put the group in the show notes, and I welcome anyone who has either lots of experience or no experience or somewhere in the middle and who wants to share ideas with others doing training as well.

CHUCK: It’s funny that you mentioned the membership site thing because I had lunch right before this show, and I went and had lunch with Blair Williams who is the developer of the MemberPress plugin for WordPress.


CHUCK: And we had a great conversation. This is the second time I've had lunch with him. He lives like 20 minutes from me. And yeah, it’s a terrific plugin. I’m using it on DevChat.tv and I’m really really liking it. So I’m going to pick MemberPress.

The other pick that I have – and this is another bit of just stuff that’s been working out – is Slack. So I use Slack to automate a lot of stuff. I also use it to get alert and things like that. The thing that I fixed up today that I figured out was that it has a Google Hangouts plugin; so you install the plugin on Slack and then you do /hangout, and it creates the hangout and then hosts the link to the hangout back to Slack so that other people can join it. And I had that call today with the developer who is helping me do the recording for Rails clips. And he’s actually worked out a whole bunch of automation so that he winds up doing a lot of work and saving me a lot of work in the process so that as I do voice over on him typing and things like that, I know what to say and I know where it goes and I can hand all of that off to an editor who can then give me a rough cut and then we can iterate from there on what goes on. And so the whole process of getting something that’s actually workable and viewable and happy is pretty darn slick. So I’m going to pick Slack as another bit of automation. You can do plugins that go the other way; instead of doing notifications, you send them commands and they set stuff up for you like the Hangouts one.

So anyway, those are my picks. And just yeah, thanks everyone for listening. One other thing I do want to shout out is we do have a Facebook page. So if you want to go like the show, just do a search for Freelancers’ Show. You should be able to find it. And we’ll put a link to it in the show notes. And yeah, we’ll wrap up the show and we’ll catch you all next week.

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