Teaching Freelancers to Build a Better Business with Erin Flynn

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Erin Flynn is a freelancer and educator based in Colorado. In this episode, we talk about how she found her way into the product space, all the twists and turns of freelancing, and how she creates courses and keeps her sales funnel on point.

Show Notes


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Hey, everybody. Welcome to another episode of How I Built It, the podcast that asks “How did you build that?” Today, my guest is Erin E. Flynn. Erin, how are you today?

Erin Flynn: I’m good. How are you?

Joe Casabona: I’m wonderful. Now I assumed that I could pronounce your name right but it’s been an obsession of mine lately ’cause I always forget to ask, that is correct?

Erin Flynn: That is correct. But actually, I am going to make this simpler for everybody in the very near future because I finally shelled out the money to buy erinflynn.com.

Joe Casabona: Nice.

Erin Flynn: You know, a nice like $1000 investment but I’m like, this is just so worthwhile because that is very confusing. So I am Erin E. Flynn, I’m also just Erin Flynn in the very near future.

Joe Casabona: Awesome, very cool. I have pined after casabona.com for years and this lady owns it and she hasn’t updated her site in like forever but she likes her email address so, like every 18 months and like “Can I have it, please! Like you can keep your email.” So if you are listening, miss, miss Casabona, please! This is a play. [laughing background] 

So I heard about you first on Rethink.fm with my good friend, Jackie D’Elia. You were talking about all of the wonderful freelancing resources that you have and I thought this would be a great show to have you on as well. So why don’t you take a little bit of time and tell us a little bit about who you are, and then the product that we’re going to be talking about today.

Erin Flynn: Yeah, so I’m a web designer and developer and I’ve been making websites for ages since 1999 was when I, you know, started with like my Sailor Moon fan sites, things like that. I didn’t make my…I started like kind of like roughly freelancing like on this side. Probably 2001, 2002 I’ve made like a website here and there but I didn’t officially like do this as a business until 2012. And it was a huge learning curve to go from I’m just going to make a website you know, for random people when I feel like it to actually running a business and trying to pay bills every month. That was a huge learning curve in my first year and was actually horrible. And so thankfully my been boyfriend and now husband supported me but along the way I think I made probably every mistake you could make and learned a lot from it. And so now I’m trying to help other people avoid those mistakes by teaching them and I still do web design and development. I’m very choosy about those now which is great that I get to be. But now actually my primary focus is helping other web designers and developers and some freelancers in general, get their business stuff in order because it’s so important and it’s just, it’s a shock to how much there is to do and where to start. So that’s my primary focus now.

Joe Casabona: That’s fantastic, and it sounds like we started freelancing around the same time. I was like a sophomore in high school, and it was like 2002 and you know, I had no idea what I was doing. My church just needed a website and I was like yeah I guess like “Will you pay me?” and you know, even as I went through college and did it full time a little bit after college, there were no great resources. So when you started putting these resources together, I guess around 2013, 14, 15…

Erin Flynn: My first product for freelancers and like web designers developers was in late 2014 when I made my email templates.

Joe Casabona: Gotcha, so at that point, there were a couple of resources. Did you do any research to see what was already out there or what did that look like?

Erin Flynn: It was not very formal. In fact, this was not like a business plan to start going into products then at all at that point. but what I saw was I actually, I majored in communication in college and so I feel like I’m pretty strong in that area and I would always be like giving advice on OK, you’ve got this bad client, well let’s look and see what happened like were the communication problems are happening. Here is what you can say to address this issue and you know fix it and move on. So that was kind of I just threw together a bunch of like email scripts that I had written for people and made it a product. And I wrote a couple more but to flash it out and now that I put it up for sale I sold like a couple of 100 copies. I was like “Wow! This is so insane! What have I been doing wrong?” And I didn’t, so the research was really just from other people like in Facebook groups or on Twitter and seeing they were struggling with something and I would write a template for that and then just kind of started a collection. And then from there, once I realized this was something that people really had an interest in because I sold a couple 100 copies, I said well how can I make this better, what other problems are people having, how can I make this something that’s really really useful. So on the second edition, I think I added almost I think we have 84 difference-like options for what you can like say in a reply that not 84 scenarios but different options for replies. And that was much more research like what are people having issues of what are/is the actual problem in the client communication? How can you kind of start that communication? Set like setting it up for success like how can you help avoid this from happening in the first place. And you know, go through to different levels of responding before it’s, I hate you, I want you. [laughing background] yeah.

Joe Casabona: Yeah. Oh man, the worst email I ever got, I think it was like well she would start off all of her emails like as a blah blah major in college and I’m like, “Yeah, I know. I too actually” just like she said “Can you send me a copy of the contract?” and I’m like “Great.” She’s like checking for this and that so I’ve been on the, you know, I think a lot of freelancers they’ve been on the side of the coin where everything goes South that I just like to mix up two settings there, it’s fine. But what would you say, is that in your research what would you say you found is the most common difficulty with client communications?

Erin Flynn: Honestly, I think it comes from expectations in the first place. It’s the designers, we know what we’re doing, and we know what we’re building, we’ve probably done this you know at least like 100 times already, it’s not new to us. And so things that are common sense like how long is it going to take, what’s the next step, what do you need from the client tends to not get communicated. And so when you have… and this actually happened to me a couple of times before I realized where this problem was. I would tell clients I need to have content first which we want to have, and I would say that like in there in the initial email but I never really made that clear, like I need all of the content, I need a final copy, I need final images, and I need everything like good to go approved. and so you know, come time for me to make the website and there [Inaudible 08:12.0] changes like I don’t like how that, you know, like looks,  I want to change this paragraph, and then I’m redoing work and so that was all a problem with expectations and communicating clearly what I actually needed from the client. and it made them really frustrated and it made me really frustrated. and that’s just one example but I mean that happens all the time, you fail to set expectations of when you’re available or you start answering emails within five minutes of them sending them and then they think that you’re always going to do that including hump Sunday mornings. So all of those expectations are really really the biggest issue. 

Joe Casabona: Gotcha, that’s such a great point. And then that’s something that you know, I’ve tried to preach to people I know as well as, especially the email thing like I used to set a hard rule like don’t respond for at least half an hour like it, like don’t make it seem like you’re always at your computer cause you might not be. And so yes, that’s really fantastic, make sure to set expectations.

Erin Flynn: One of those email things, this is a trick ’cause my brain won’t let me not respond to things sometimes. If you get a streak for Gmail you can set it to send like an hour later which is what I almost always do so I will, it will come in and I’m like, “Oh my God! I have to respond to this” ’cause I just, I get anxiety over my inbox. But it won’t send until an hour later if I know I don’t wanna hear from that client again that day ’cause I need to focus on other things, I’ll send it at 5:00 PM.

Joe Casabona: Oh, that’s fantastic.

Erin Flynn: And that’s like the last email of the day and it goes out then and it’s like I responded, they’re still getting a response very quickly. It’s totally reasonable but it takes that pressure off and you’re not chatting in your email.

Joe Casabona: Yeah, that’s awesome. So I use a new end which is like a paid for Mac App but it’s got like this snooze functionality and I will graciously use that so I’ll snooze an email for “All right, I’ll deal with this later” but that think I like your way better ’cause you get to respond and it’s like off of your plate. Cool. S being a freelancer, I know it can get really hard, you work from home, you’re often in a silo but I also found that like being part of a mastermind group or bouncing ideas off of other people helps a lot. Do you talk to anybody about business advice and direction or anything like that?

Erin Flynn: Yes. So I highly recommend everybody get into a mastermind. And I really actually enjoy it. I’m into masterminds and I really enjoy being in one that is a little bit more web design and development focus and the other is not. So it’s great to have outside opinions because when you’re with just other web designers and developers, you can go really in-depth into industry problems which are fantastic but you can’t see, and they can’t see the issues that regular people who visit your website or trying to buy your services can see. So having somebody who’s you know, a copywriter or business coach, or just it’s a completely different industry in a mastermind with you is fantastic. 

And I also highly recommend going to conferences and conventions and getting out there and seeing people in real life who get it because that is the most amazing and fun thing you can possibly do.

Joe Casabona: Yes, that’s awesome. Like plus one for the conferences ’cause I’ve made a lot of my friends today from going to conferences. Remembering how to interact with people in real life, now we’ve had this conversation on Twitter but I’d love to bring it to the podcast. Do you, you know, we both work from home, do you go to a coworking space at all or anything like that?

Erin Flynn: There are no coworking spaces. I used to live in Denver and there are a ton of guns and I have some friends in Denver who post photos where their coworking and I get so jealous when fortunately the closest one for me is like, think 2 hours away and that’s just not ever happening.

Joe Casabona: Yeah, that’s rough. Man that’s, I was spoiled when I was living in Scranton. I lived like down the street from my coworking space so I could like walk there if I wanted to.

Erin Flynn: That’s nice.

Joe Casabona: Yeah, so this one, the one where I am now is like 20 minutes away which is I mean not two hours away but it’s still like I wanna, I don’t know, it’s like I have a lot of meetings today that’s the hardest thing for me is if I have a lot of meetings, I don’t wanna go out to a coworking space. Cool. So we’re about halfway through. Great, this is perfect! Let’s get to the title question, so how did you build it? And I don’t think we’ve really defined it at this point, you know, we talked a little bit about your email templates and your product’s but you have a membership site, is that right?

Erin Flynn: I do. I have a brand new membership site that is still in the early stages of getting everything added. But I have incorporated that all, a lot of the things that I had created before into the membership so it’s really exciting to get that going.

Joe Casabona: Awesome. So before we started recording you’re telling me a little bit about how you’re moving platforms. Can you tell us a little bit about how you initially built this site and then kind of the decisions and process of transferring everything over?

Erin Flynn: Yes. So I originally, actually I originally started on Teachable as a minimum viable product. Getting that going and just seeing if anybody would buy, I immediately spent so much in fees to Teachable that it made more sense for me to move to Rainmaker which I adore as a platform. and I know some people find it very restrictive and for personal sites like it’s like a web designer, developer you might. But for hosting like a big signature course, it’s awesome, like a startup camp if you’re familiar with that is on there and that was a lot of my inspiration when I was looking at how to build my site. But my issue was that, well it was fantastic, for my signature course ‘Creative Compass’ it did not work well for the workshops. I mean it worked fine but there are a lot of steps with any WordPress type LMS or membership to add things. You have to do download protection, you have to upload the files that you have to like manually put them into the page, the right member groups, it was a lot. And like I said, a signature course that you build once, was the perfect platform but for adding something every single month, I was like, I want something where literally my husband can go in. He could upload a file, edit, and Done, he just hits publish and it’s done. And so that’s why we’re actually moving back to Teachable because I don’t want my business to be so reliant on me, hitting that publish button and I don’t want to have to hire another basically developer to be able to do that. So this is not knocking the Rainmaker platform at all. I guess that I love it and I think it’s fantastic for big signature courses. But for what I wanted to do adding content basically constantly I just wanted something super easy and teachable. After doing a ton of research as to why Teachable is reasonably priced, it makes it easy for people to still buy individual products if they hate the subscription option because some people do. And so it just made, it does lack a lot of things that I would like to eventually have a membership. There are no forums, you know, there’s not really like page protection, it’s really just the courses. So it is lacking in a lot of things that way but I feel like again for a minimal viable product membership site, it’s a really good place to start. And you know, a year from now, we’ll see where we are and maybe I will find some other platform whatever is cool then.

Joe Casabona: Yeah, absolutely. And so you have your signature course which maybe you can explain a little bit about and then you have these workshops which serve I guess like a different purpose, is that right?

Erin Flynn: Yes, so my signature course ‘Creative Compass’ is basically if you’re new to creating your web design business or you build it and it’s not going very well, it takes you through everything from structuring your business around the life that you want to live. So that’s actually where we start. We start with figuring out where you want, what you want your life to be, and then everything is built around that. And then it takes you through pricing, it takes you through some marketing and networking with people and helps you write your business plan that you could actually follow because you thought everything out. So that’s my big signature course that I will likely keep on Rainmaker because it’s perfect for that.

And then the workshops are short actionable things that you can typically do in an afternoon or a weekend so I have an intro packet. So what that is, is basically if somebody comes to your website and I said “I want to work with this web designer” they can either email you and then you send them the intro packet or other people make it a download like a download this and get the information. And it basically walks through all of the things that you need to set for expectations. This is approximately how long a website is going to take, these are the office hours I work, this is when you can expect, you know, to hear from me during the week, things like that. It helps you get all of those things set up.

And then I have other workshops too but the workshops are like short actionable things that you can do to immediately improve your business without having to go through a six-week course. 

Joe Casabona: That’s awesome. It sounds like a really great resource. And we’ve talked a little bit about you know, the transformations you’ve gone through. But with moving platforms what would you say is like the biggest challenge in that?

Erin Flynn: You know the biggest challenge for me is feeling like I have to justify being obnoxious to my audience. Because like I said we started on Teachable and then we moved to Rainmaker and now six months later I’m moving all of the workshop stuff off of Rainmaker and it’s just, it’s a hassle for everybody. It’s like one more thing people have to add to their To-Do List so I feel bad about it. I feel you know, like I’m very annoying like “Hey, thanks for moving. By the way, go back and you know sign up for this now” And so that is a hassle. But the other thing that is frustrating is people who don’t understand the difference between the two platforms ’cause I’ve already got a couple of emails from people transferring and they say “I don’t understand where am I supposed to log in?” And so I wasn’t clear enough about them being like two separate things and we need to, so I had to go back and do some clarification and so that’s really kinda frustrating.

And the other thing I guess, the third and final thing that’s frustrating about it is when you have so like I have everybody like tagged in Convertkit but not everybody originally made the move from Teachable to Rainmaker and now I’m trying to move them back but I set up my courses separately. And so if they weren’t tagged as being a student from Rainmaker then they’re not getting the email so I’ve had a couple of people message me and say “Oh, somebody said we’re moving” I’m like “Oh my God!” I have to go back and do it. So if you’re going to move platforms, you really think through all of the steps and what you’re going to do, you know, about simplifying those moves and maybe even write up some email templates so you could just shoot them off ’cause now I’m just sending like copy-pasting to everybody who asked the same questions.

Joe Casabona: Gotcha. Man, that’s wild. And so that made me think of a very interesting question, right? You’re a freelancer but it sounds like you’ve got a few tools to help you automate a couple of things like you specifically mentioned Convertkit. What are some of like the must-have tools or the must, you’re like top five things that help you run your business?

Erin Flynn: ConvertKit is definitely one of them. I adore Convertkit and a lot of people have asked me how to use that as a web designer/developer and I mentioned the intro packets before. So if you have somebody fill out your contacts page, you can immediately send them your intro packet like as you know, either through a Convertkit trigger Gravity Forms trigger or something like that. But then you can also automate follow-up emails to get them to book that initial call for you or to fill out the information that you need. And so you know, just a short email series that says “Hey, look at this person I worked with, they have had great results from working with me. You can book your console call here.” Do things like that and I mean that makes it so worthwhile. And of course, you can do automation with other email platforms too but ConvertKit is so easy to use that I highly highly recommend that. And that’s just a little example of how I would use that as a designer to funnel clients to actually booking with you once they’ve made that initial contact without having to do that much follow-up on your part which is a great time saver. 

And then other things, it really kind of depends on your business obviously, you know, like Photoshop and illustrator, whether we like them or not. And then I’m a big fan of Studiopress for themes. I really love doing Genesis child themes. I think that’s a really great option for developers. I like doing the child themes because I know that Genesis is always going to be updated, it’s a good solid framework and I don’t have to worry about that. I just have to worry about you know, the pretty and the additional functions and a child theme. So as a developer I don’t even touch themes like better not Genesis like, “Oh, it’s not a Genesis site, sorry.” so I’m a little snobby there but I love it.

Joe Casabona: Yeah, and I mean you got to, you know, you got to, you wouldn’t ask like a corporate lawyer to do, you know wills or something like that, right? You know, you want them to stick to their specialty, so.

Erin Flynn: And you wouldn’t take your Tesla to a Toyota dealer.

Joe Casabona: Exactly, right. That’s like maybe a much better analogy, so.

Erin Flynn: And we both have Teslas right?

Joe Casabona: Yeah definitely, a wish, one of us makes wishes. He does, so.

Erin Flynn: So, I don’t even mind one.

Joe Casabona: Yeah, right, exactly. So awesome. So we’re coming up on time and I’ve got two questions for you. One is what are your plans for the future?

Erin Flynn:  OK, so what I really want to do is, this is gonna be a long answer, so I want to keep doing like the design and the development but I wanted to do that with the team because right now I’m referring people to a copywriter and then I’m referring to marketing strategists. And so I’m getting my agency up and running and we’ve done a couple of projects so far. But I really wanna take that to the next level and make it a really good streamlined process ’cause we’re still working those kinks out. So I wanna do that and I wanna do a few, I don’t want to do a ton. I don’t want to be like you know, doing a million websites per year. But I wanted some really great websites, you know maybe do five per year that is just awesome with this agency where we can really make a difference in somebody’s business.

And then I want to have more courses, obviously. So if the membership I’m trying to release content every single month for that. So I want to have more courses and more resources for web designers and developers and kind of have like a central hub where people can go and they can get the information they need to run their business. Not necessarily how to do coding or design but how to do that business portion specifically to web design and development because that’s general business advice everywhere, it’s not necessarily applicable to web design and development like you don’t need a 10,000 member or subscriber email list. You just need maybe ten really good clients per year or five if you charge enough.

Joe Casabona: Right, right.

Erin Flynn: And you’re done. So there are, you know, things specific to our industry, and I want to get that hub together and bring in some more people to help contribute to that and have a really really great resource of our designers and developers.

Joe Casabona: Yeah, that sounds fantastic. Good luck! I hope for all of that and more for you. And I wanna ask you my favorite question ask which is, do you have any trade secrets for us?

Erin Flynn: I don’t know that I have secrets because I blab everything that I learned to everybody like “Hey, did you know about this thing? Let me tell you about it for way longer than you wanna listen.” But I think the biggest thing is to listen to your audience. Whatever it is that you’re doing, listen to them on what they’re saying and that doesn’t necessarily mean you even have to go ask them questions all the time. Just pay attention. If you…I want to work with fashion bloggers, for example, make a Twitter list of fashion bloggers, follow it and pay attention to what they’re saying, see what they’re struggling with their websites or trying to, you know increase how much money they’re making, see what their problems are so you can address them. And kind of that eavesdropping is actually sometimes more helpful than directly asking because there, they are not filtering what they’re saying. They don’t have to put like this vague thing into words. I just kind of vented your frustration that you can then fix for them. So really pay attention to what the people you want to serve are saying so that you can be that person to fix the problem.

Joe Casabona: That’s fantastic. So it goes to you know, kind of understanding your niche and having domain knowledge of what they’re going through. That’s fantastic. sS listen to your audience. As soon as you said that, I thought of the rocks in the song, ‘Listen to Your Heart’ so that’s gonna be stuck in my head. Hope it stocks in everybody else’s head now too.

Erin Flynn: You’re welcome!

Joe Casabona: Erin E. Flynn, soon to be Erin Flynn, thank you very much for joining me today. I really appreciate it.

Erin Flynn: Thank you. I’ve had a lot of fun.

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Thanks so much for listening, and thanks to our great guests and fantastic sponsors. If you liked the show, please rate it and subscribe on iTunes in Google Play or whatever your podcast app choices. If you have any questions, be sure to reach out at how built.it.

And finally, till next week, get out there and build something.


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