The Ruby Freelancers Show 038 – Optimizing Pipelines

by woody2shoes on December 6, 2012


  • Eric Davis (  )
  • Evan Light (  )
  • Jim Gay ( )
  • Charles Max Wood (   )


01:11 – Optimizing your sales and marketing pipeline

  • Lead generation (marketing)
  • Lead conversion
  • Project delivery

08:54 – Follow ups

11:24 – Lead categories

  • Want to work right now
  • Trying to decide
  • Decide against you

12:26 – Closing a client (sales)

  • Not just going for wallets
  • Leads who take advantage/getting something for nothing
  • “Velvet Roping”

15:57 – Client fit

  • Qualifying

17:36 – Marketing

  • Mailing lists
  • Open-source contribution
  • Being active in communities

19:31 – Referrals

  • Where do they come from?

22:05 – Recruiters

  • Responding to recruiters
  • Dealing with recruiters

28:01 – Website traffic analyzation

31:41 – Newsletters

  • Listening vs reading
  • Getting newsletter subscribers
  • Autoresponders

47:09 – What should I do?

  • Where do you want people to wind up?
  • Make it easy for people to contact you/get them where you want them to go
  • Landing pages
  • Comments on blogs

53:31 – Your personal ideal pipeline


  • (Eric)
  • (Eric)
  • (Jim)
  • (Chuck)
  • (Chuck)
  • (Chuck)
  • (Jim)


EVAN: If someone takes a poker and makes it really hot and shoves it in your behind, that would be a branding problem.

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CHUCK: Hey everybody and welcome to episode 38 of the Ruby Freelancer Show! This week on our panel, we have Eric Davis.

ERIC: That’s me.

CHUCK: Evan Light.

EVAN: I wasn’t ready!

CHUCK: Jim Gay.

JIM: Hello from a standing desk.

CHUCK: And I’m Charles Max Wood from This week, we are going to be talking about Optimizing Your Sales and Marketing Pipeline. Sounds like a mouthful. So do we want to start with a definition? What is the–

JIM: Is this Ruby Rogues? Did we dial in the wrong place?

CHUCK: [laughs] Yeah I kind of felt like–


ERIC: Yeah, I would like a definition.

CHUCK: Well, my understanding (and you guys can and probably will correct me) that the sales pipeline or marketing pipeline is effectively the process that you put your prospects through basically from the moment that they encounter your website or market message all the way up until you convert them to a sale or to a client. Is that oversimplified or did I miss something?

EVAN: I would say “leads” not “prospects”.

CHUCK: Leads?

EVAN: Yeah.

ERIC: Yeah. It basically starts at leads. Like you know, this person might have come to your site like an anonymous visitor or maybe they heard of you or something that was like, “Oh, who’s Chuck?” and that’s kind of where they start that. And then it goes to… what is it… suspects? No, actually suspect is fair. Suspects are people that might be a good candidate for your business. Then its leads when they actually kind of contact you… there’s also prospects. It’s hard. It’s modelled and it is overly complex in like enterprise but for us, I think of it as like people that might wanna do business with you and its process of moving those people from they might wanna work with you, all the way to they do wanna work with you or they don’t wanna work with you.

JIM: I’m curious where you got those terms. Because I have like no rigor around how I do this.

EVAN: Various books. [laughs] I haven’t heard “suspects” before. That’s usually when the police pull you over and think you have drugs in the car.

JIM: Usually.

[overlapping talks]

CHUCK: If they keep coming back, then they are the usual suspects — otherwise they are just suspects.

EVAN: Keyser Söze.

CHUCK: [laughs]

EVAN: Someone who didn’t know expect—

CHUCK: That’s such a good movie. Anyway.

JIM: So what is the process then? I mean, like for example I have rarely gotten (at least as far as I know) leads from my site. It’s often there is a validator. I think  maybe people have gone there, they already know about me in some way but they have gone there and find my phone number. So I don’t really have on my site a contact form that I remember.

EVAN: So I’ve gotten leads from my site. I’ve gotten not many, but actually some jobs from leads from my site. I’ve gotten most of mine from referral. And I guess in trying to come up with some sort of definition still or high level process in a nutshell, for me it’s always reach back out to a lead as soon as possible — plain and simple. Get them on the phone. Email conversation might be adequate if you are … for me at least if I’m a little leery of the information provided by a lead, if they are like sketchy, then I might use email to keep them a little bit at arm’s length because I’m dubious and maybe I shouldn’t even bother. Well, no. Being dubious I think is worthwhile if you think that phone call is going to be a waste of your time — if you are sure these leads are not going to be worth it. And when I say that I am talking about leads where it sounds 99% sure that they just wanna get the equity for something. Then that’s probably not worth a phone call, just usually a follow up by email. But anything that sounds like it may be valuable at all, I try to get them on the phone as soon as I can.

JIM: So how do you qualify them in? I mean what sort of questions do you ask this potential client? “Do you pay on time?”

EVAN: No, well that’s a hard one to—


CHUCK: [laughs] “Yes of course I do!”

EVAN: For me, I guess I do a little bit of background checks. I guess I have a tendency to Google new clients or new leads that come my way. It’s also based on the quality of email itself. I will actually judge people by the content and the quality of language that they use — perhaps it’s fair, perhaps it’s not — but it’s something I consider a little. But in a nutshell, I got them based not he information that is available to me. If I just have a name and an email, then I reach back out and I will ask a few more questions via email before making a phone call because I wanna know a little bit more about them. And if they give me enough information, then I’ll go search in the net. If they haven’t, then I’ll try to collect a little also maybe I can search them on the net. And if they sound like they stand a reasonable chance, you know, greater than maybe 1% worth of being worth my time, then I try to get them on the phone. So most of the time, I try to get them on the phone.

CHUCK: I think it’s interesting that we start talking about the sales funnel and we more or less wound up skipping all the way to the end.

JIM: Halfway to the end — I’d agree.

EVAN: OK yeah because there is the, “How you get their attention in the first place?” But that’s … Well OK, we talked about that recently because for me it’s like talking in conferences — and we just did that one. But that’s just me. That’s not you guys necessarily.

CHUCK: Yeah. I’m not saying we are in the wrong place, I just think it’s interesting that that’s where we wound up going first. So maybe that’s where you go in mind or some of us are thinking about things as far as just following up and being in that process. How frequently do you follow up? Because if we are talking about this part, let’s just go ahead and just talk about it. How frequently do you follow up and we did talk about what information you need to them, the point that you are talking to them in the phone and starting to get to the point where you can finalize the contract.

EVAN: OK. So first I’ll say I tend to follow up about once a week until I have some kind of stronger contact, but second I want to say that I would like to get to that part of the conversation that I guess I inadvertently jumped ahead of because this part I feel good with — the marketing through sales part. I guess we are starting to talk little bit more about sales at this point aren’t we?

ERIC: No, I mean—


EVAN: I want the part before this.

CHUCK: Right.

ERIC: I actually have processed documents for this and I’ll run through what they are called, and that kind of might give us some terms to hang on. So, basically there’s three parts; there’s lead generation, which is basically creating interest for my services and get people to contact me. Second one is lead conversion, which is where I work with a potential client to turn them into a client. And the third is project delivery, which is actually doing the work and delivering it.

So, lead generation is kind of what we call “marketing”. Lead conversion inside of that, there is like I have lead filtering. Like, can I help this person? You know, like what you were talking bout Evan the question just to see, “Are they reasonable?” “Is it going to be a good relationship?” I had a new client consultation system which is probably close to yours like getting them on the phone and talk to them and then I go to follow up. And then it’s basically at that point it’s a proposal or a contract and pitching the sale at that point. So that’s my process.

EVAN: That doesn’t sound all that dissimilar to what I do. I just don’t have a system per se.

CHUCK: I was going to ask, do you have a system for follow ups and all that stuff, Evan?

EVAN: I have a good memory for people, so I tend to know which. Well, I guess with people, it’s not usually a stress point for me to remember the open loops I have in terms of people who I owe contact to. So, I usually remember depending on a need that I’ve generated that I’ve yet to convert, periodically.

ERIC: So you have a system. It’s just ad hoc based in your memory and how your personality works then?

EVAN: Yeah it’s that. Ad hoc I don’t think is quite fair, but yes I have a system built around how I work.

ERIC: OK, not ad hoc but maybe like documents or whatever.

EVAN: Yeah.

CHUCK: OK. Eric, it sounds like you have a much more documented or refined system — something that you’ve worked on for a while. To do this?

ERIC: Sounds like it. I have rarely gotten through the whole thing. Like typically it is not like I started documenting the whole thing as I was working for lead and then he just wanted to jump ahead and start working together. So I just started to work with him instead of like, “No, wait we have to slow down.” So I have the first part, like the marketing and like filtering the leads, all that stuff pretty well documented because I go through that a lot. But follow up, kind of like Evan, every week or so, I kind of email them or call them. And it’s very ad hoc for me. I don’t really have any essential thing around it needed it. Mostly because I haven’t needed it.

EVAN: Not necessarily all that different than me except that maybe you keep more documentation.

CHUCK: I found it really hard to keep track of all of the folks that fall in to the category of leads at various stages. And so what I started doing is… I do all my email through Google apps and in my browser I have the Omnifocus plugin (whatever it is that), sends this page to the Omnifocus inbox. And so what I do is I put it into my to-dos is what I started doing. And then I just make sure that I clear my to-dos regularly. And if it sits there for more than a week, then it becomes a critical thing that I have to do the right way. And so, that way I am following up every few days to a week with those folks. But then it’s not regimented. They don’t hear from me every seventh days, it’s when I get around to further in the conversation and it’s no more than a week.

EVAN: So, Eric kind of said something here that got me thinking that I think I’m the one who often says that clients seem to come in two categories; there is the kind that are ready to go right now and then there are the kind that tend to be… So I guess technically I said “clients” I should say “leads”. They come in three categories then; the kind that want to go work now, the kind that’s trying to decide and then the kind that are going to decide against you or decide against you. Because the kind that ready to go, they wanna work with you right that second. And they skip your whole process, Eric and they skip mine too, basically. It’s, “OK where do we send him to go work in this project.” And occasionally I will get them back and go, “Whoa, whoa, whoa. Let’s hear about the stake first to make sure that I’m actually a fit at all.”


JIM: Yeah not that it’s a bad thing sometimes.

EVAN: Right. I mean if they just wanna pay me, well that’s great. I just wanna make sure that I’m the right person to take their money. Because, that’s something that matters to me and I know what matters to you guys too. But what I think for me the interesting/tricky part (I think this is probably true for all of us) is that undecided group — the kind where you got lead and it’s a matter of pulling them if look deeper in to your pipeline that you are trying to get closer to a conversion. I guess that’s sales.

JIM: Yeah. And I think you know, from my perspective, I always to try to do whatever I can to leave them with the impression that we’d be focused on their problems. So whatever conversation I have, I ask as much about what they do as I can and not say, “Well, I do this and I do that.” So making sure that the conversation is always back on their needs and then giving them suggestions like you know, “I would try looking at this,” or “If you run in to this problem I would do that or take a step back and think about it in different way.” And then they at least walk away from the conversation like, “OK this person was not only focused on my problem, but willing to offer assistance without trying to nickel-and-dime me.” And I think just leaving that impression that you are not just going for their wallets, you know or just wanna be heads down the code and left alone and you know, that type of thing, I think being genuinely helpful before you’ve even signed on the dotted line has been beneficial.

EVAN: Now I concur, but I’ve also had one lead who would take advantage of my tendency to do that where I had at least four prolonged conversations (at least I have more probably an hour each) where this guy was trying seemingly to get something for nothing, where he was trying to get advice without having to pay anything. And ultimately, I ended up referring him to someone else who did actually  do some work with a little bit here and there. But so what I’m trying to get at is while I completely agree with what you said Jim, there is this crazy line where you have to be sure that you are not giving away the whole house.

JIM: That’s true. I mean I think you probably won’t admit this but you probably made a mistake. You probably should have not had four conversations with him like that though without… You know after the first one, going to the second you should say, “Well, why don’t we have a planning session? Why don’t we start plotting out the path because we can talk about this so many times but I have to actually do the work.”

EVAN: No I’ll admit it. This was a couple of years ago when I was still newer at this and he sounded interesting at the time. where I would have probably would have velvet roped him sooner, (referring to a book by — I think it is.) I probably velvet roped him sooner because he was seemingly trying to get a lot for free. But for me it’s also, (we talked about this another conversations too) drawing some kind of boundary of how much do you give for free. And I have said before that it varies by degrees based on the potential scope of the project too. If it’s going to be a tiny project, you wanna invest a lot upfront winning the project. If it’s going to be a huge project, how much of your own time you want to risk closing it?

CHUCK: That makes sense. Unless there is something else that is critical to add to this, I want to move back a little bit to the marketing end of things where people are coming in to the funnel to begin with.

ERIC: Well, there is one thing I wanna add because Jim and I both kind of talked about like we kind of stayed focused on what the client needs or potential clients — what they are talking about. I’ve done that in the past and I still do that, but I also try to bring up what my business needs and that’s part of like, “Is my business a best fit for you?”

Like if a client is demanding an insane schedule, I can say like, “Look, I have my business, I cannot service you in that need.” So the big thing is I wanna make it clear to the client upfront that I run a business too. It’s not just you hiring a warm body that type of code. And I think kind of setting that right upfront in like the first call is kind of a good thing. I don’t worry about like, “You need to pay me,” or you know, “I get days off,” type of stuff but more in the high level in, “I’m a business it’s not just an employee or a warm body.”

CHUCK: Yeah.  It’s about the fit. I think that goes more or less without saying but yes I’m glad you clarified it because we do need to make sure that people recognize that. You know, you want to make sure that you fit their needs in all those ways and not just in your capability to write code.

EVAN: That’s a conversation I tend to have with them very early on. Qualifying myself with their project first requires that I know what their project is. And then once I do, and I know what their need is also something I ask about upfront. And I usually ask about their budget very early on too. I can very quickly figure out: One, is this something where they can afford me? Two, do I have the time for it? And then there is the question of, “Am I interested and do they want to work with me?” The, “Am I interested?” part is purely on my side really, but do they wanna work with me on their side?

CHUCK: Yeah. All right. Well let’s move in to the marketing area — getting people kind of in the door on the first place. Because I feel like marketing is sort of everything out to the point where you start talking to them and trying to make the sale. So once they become a lead, you are more or less in the sales land. I don’t know if that’s a demarcation for everybody, but for the sake of this conversation let’s just say that it’s there.

EVAN: I’ll buy it.

ERIC: I basically think of it as you know marketing is you converting anonymous people that you have no clue who they are into someone like name, email, a phone whatever. It’s the way for you to get in touch with them.

CHUCK: Yup. So what kinds of things do we do get people in the door in the first place?

JIM: From my experience, at least as far as development goes, I early on would get clients when I was doing a ton of Radiant development couple of years ago, I would get application on the mailing list. It was open source work and I was active on the mailing list, and I’d be helping people there, and I would take calls and say, “Hey, it’s someone from the Radiant mailing list.” And I would of course act like, “Oh yes I remember seeing your name.” Even though there’s like several hundred of people on there, I didn’t remember. I would get calls like that. So open source contributions have definitely helped, but it’s not just open source, its being active in the community. You may not contribute at all, but contribute to the conversation in the community and people will say, “OK, he knows what he is talking about. When we run in to problems he is on our shortlist of talking to people.”

CHUCK: Yeah.  I’ve gotten a little bit of work on open source learning management system that’s written by a company up here and it’s just because I’m on the mailing list. And it also helps that I know almost all of their development and support staff because I worked with them at the previous company. So that definitely works. I remember hearing Eric or Evan mention referrals. I think that’s another good way of doing it. Do you usually go and try and… I don’t wanna use the word “pump” but pump them, pump people you know for referrals? Or do you wait for them to sort of organically come up?

EVAN: I ask periodically. I go back to good clients and good former clients or even current clients and I’ll ask for referrals. But it’s not something I do often. Besides it’s not like I have had a huge — of clients to go ask, but I usually start with them and then occasionally ask other folks. Usually I just wait for referrals to come in because they often come in based on my having run DCamp or having spoken at a conference or occasionally some open source I’ve done.

CHUCK: Yeah. I’ve gotten referrals also from other clients. I’ve also gotten referrals from other developers who are on projects that need another dev and they think of me.

EVAN: Yeah. Gotten those too.

CHUCK: Do you ever get any anonymous ones from your websites? Any of you guys?

EVAN: One or two. One of my current clients.

ERIC: A lot I think this goes back to what Jim was saying. I did a lot in like the RedMine community for open source. So it got to a point where people would ask in the RedMine forums someone else in the community would recommend that potential client to me and so that potential client would come to me, but they would come to me through my website. So it’s like the first time I hear about it is through the website but it’s actually because of stuff I’ve built up in other areas.

CHUCK: So that is something that is interesting to me in the sense that optimizing your pipeline is that, how often do you know the circumstances under which you got the referral or somebody coming to your website.

EVAN: I try to find that out for each lead that I get whenever possible. I don’t always get an answer, but that’s why I say that I’m sure that some of them would come from conference speaking because sometimes it’s come back to someone heard me speak and that person mentioned me to someone who said they were looking for a contractor. The ones where it’s from DCamp I know the people already usually. When it’s from my website, they’ve often just told me that. But I don’t know about you guys, but at least I try to find out for myself.

JIM: You know, I haven’t. And it’s something that’s just so simple. I really should. And every time somebody contacts me to say, “How did you hear about me?” I’m on a project now that I got through a recruiter, so that can be good sometimes. It was a difficult negotiation process because the recruiters are looking for (most of the time anyway) employees. So you sort of have to battle that and it also changes the perspective on who you are. They think of you as an individual more than they think of you as a company. So if you are helping doing staff augmentation and you are a part of the team rather than them like a client who sees you as a vendor and then pay you to build the product or build  some features into a product, it’s just a different relationship. So it depends on what you wanna do, but recruiters are potentially a way to go as well.

EVAN: I’d like going on a tangent and ask you a little bit more about that because I have usually had miserable luck with recruiters. I gave them a whole lot of a chance. But how does that work out?

JIM: I think that that’s the key. It was a couple of years ago. I didn’t think much of it but I came across a comment somewhere, I have no idea where I don’t even remember what the comment was but essentially, the gist of it was, “Look, sales men and women and recruiters — people who do that type of stuff constantly on the phone all day are people too.” And—


EVAN: What?!

JIM: [laughs]

CHUCK: They just don’t have souls, Evan. That’s the difference.

EVAN: Oh! OK OK. Thank you, Chuck. I feel better now.

ERIC: Well the thing is I’m married to one so I kind of know they are people.


CHUCK: You just kind of know?

EVAN: Are you sure?

ERIC: Fairly positive.

CHUCK: He’s married to one and he can only kind of know that they are human.

ERIC: If you wanna get on a tangent and—

[overlapping talks]

EVAN: So you are telling me that Eric’s child is half human, like Spock?

CHUCK: No. It’s not human and half kind of human.

EVAN: [laughs]

JIM: Anyway. So I started just changing the way I responded to people like even if I got a telemarketing calls at home, still I would say, “No I’m not interested.” And I wouldn’t, you know, yell at them even though sometimes you feel like that. Usually I’d tell people, “Good luck. I’m not interested.” “No I’m not interested.” and have to repeat it. But recruiters, sometimes I would just respond to people I have gotten potential projects and projects just writing back to them and said, “No you wrote to me in all caps. You really don’t need to do that…


Why don’t you try approaching it this way.” And it just sort of the conversation where you’re a person who they start to realize this isn’t like everyone who wants to shut them out. And I think a lot of recruiters don’t realize, (when times are good anyway) how developers see them. Like I’m one of the organizers of Arlington Ruby and we’ve had people come there as well as DC RUG in the area and we’ve had recruiter show up and like, “Hey, can I come and say something?” “Sure, we’ll give you time.” And we had one recruiter come and say, “I’m hiring for so and so. I got to talk to you about our projects. We are doing xyz. I’m going to leave my business—


EVAN: I felt that you are finished, but I’m going to ask a question here, when you got to negotiating the… in terms of money, are they paying you? And if they are not, how did they make money because that’s what they are looking to do when they try to find you a gig.

JIM: Sure. Well, I see that as a collaboration right? They are trying to fill position and I can help them do that. So I think having that conversation is fine. I say, “Look, you make money off of this so how can we figure out the best way to do some deal with a client.” The way it worked out for me is I didn’t have to really worry about it but the client was paying a flat fee to get somebody in. So—


ERIC: Sometimes it’s flat fee, sometimes its percentage.

CHUCK: Yeah. I’m going to jump in here because I got a job that I did, what  10-15 hours a week contracting through a recruiter.

EVAN: You’re kidding.

CHUCK: No I’m not kidding. When I got contract in, maybe 6 months ago or something, anyway the way that it worked out was that I would forward him a copy of my invoices, and then he would invoice the client for whatever percentage he was supposed to get paid.


CHUCK: And so, that’s the way that worked out. And he kind of specialized in Ruby on Rails and you can probably figure out who it is just by that if you know many of the Rails recruiter folks.

EVAN: I know enough of them, yeah.

CHUCK: But yeah that worked out pretty well. But you are right, most of the time they are trying to fill position. And so what I found they usually do with me is they are trying to bring me in because, “Hey you got a referral fee if we place somebody that you refer to us.” And the other thing is I usually don’t blow them off and yell at them unless I can’t understand them because they are from India or something and I’m just like, “OK I can’t understand you, I’m sorry. We can’t talk anymore because doesn’t help.” But usually I just tell them, “Look I’m only interested in contract positions. I’m willing to travel for the first week or so with the project, but after that I’m going to be working from home. And if you can make that work, then call me back.” And of course they never do. They take me to lunch sometimes but that’s about it.

EVAN: In fairness, I said I don’t give a crazy chance like they are not human but I do actually. It’s just that being as remote as I am, it usually doesn’t get very far. Its only when their government contracting recruiters that I tell them that I would sooner eat a bullet and work for the government. And then I had a few really interesting conversations after I send them that email. And I do quite literally tell them that email.

CHUCK: Yeah. So if we are talking about optimizing the sales pipeline or the marketing pipeline, I’m wondering do you guys ever analyse the traffic coming to your website.

ERIC: Yeah. A little too much I think but yeah.

EVAN: Not enough. Personal site not the business site.

CHUCK: So, what do you look for, Evan or Eric?

EVAN: [laughs]

ERIC: Yeah whoever is talking. [laughs] I guess this is the reason I built a Sinatra app that basically reads a JSON file that I make by hand that attracts visitors to my site the amount of people who have opened a newsletter (because I use newsletters for marketing), so if people open a newsletter for this month, people who have contacted me people, the people who I actually talk to and figured out that yes this is a potential client, and then the people that I close on and also the people that I don’t close on for whatever reason. And so it’s all metric based and percentage of this much needs to go down in the funnel and all that. I guess I’m over analysing it a lot, but yeah.

CHUCK: Do you ever look at where the traffic is coming from or Google keywords or any of that? Use any analytics tools for that?

ERIC: A little. I mean I’m using Google Analytics like everyone else in the world. If there is a spike, I will see what the spike is about like Hacker News sent a whole bunch of people in a day. I might look at keywords but then I mostly use my blog. My blog is 7 years old, maybe longer. And I don’t know how many hundreds of posts on there so I get regular steady traffic. It might not actually be potential leads, but I get enough traffic that looking at keywords and all that stuff, there is too much volume of data for me. And most of the time, like I said it’s like the numbers here is like maybe 1% will contact me. And so you know, if I dig in to the analytics on kind of the front-end but like x many thousand people visiting, I would get stuck there. I prefer to optimize it to people that do talk to me; getting those people to either close or not. That’s a better number for me to optimize.

CHUCK: Yeah. I was just thinking because it seems like the things that you want to do are basically increase the number of people coming in your website and then increase the number of people who are going to your contact page and entering information. And if you look at the analytics, sometimes you can figure out, OK these are the things that people keep coming and looking for, and these seemed to be the articles that more people are coming from to go to my contact page to whatever and then try and figure out what the difference is and do some, you know, write some other post like those or see if you can figure out what the x factor is for getting people in.

ERIC: Yeah. I mean I guess that’s kind of pick topics based on what I’m looking for, like I’m doing a lot to test and stuff for this client and so I might write a couple of articles on high level testing kind of targeted at my potential clients try to pick up another client like this one, but I don’t really analyse it as more gut feel and also what I feel like writing about.

CHUCK: Yeah.

EVAN: I basically do the same thing. That is that I end up my marketing at least when it comes to blogging is working based on things I feel like writing about, [chuckles] so I don’t give it as much thought. It’s more what I wanna share with the community and maybe some of it comes back as marketing, but it’s not really intended as that.

CHUCK: I could see that but at the same time, it does pay off because you are writing about stuff that you care about.

EVAN: Right. It’s all form of marketing relevant to what I do for a living and I care about it.

CHUCK: And so people if they come in and they care about the same things you care about, then they are going to find those articles and eventually contact you for one reason or another. So I wanna move on other topic just because I’m curious about it and Eric was the one who bring this one up — newsletters.

EVAN: I should have one. [chuckles]

JIM: Yeah. I do not have one for potential client work. I have for years thought about doing one and  I just never put it together, sadly I thought I would be better off had I done that. But from a book, it wasn’t really until recently that I realized I needed to keep people engaged when they buy Clean Ruby or they sign up for the mailing list, I just have content that I send out to them and I’m still in the process of building that content as I write the book. But just keeping people engaged with helpful information or reminding them who you are I think will be a very good thing. You know, especially if clients hire you to either build products or to help their teams get better on what they are doing, you just write content related to that and help them in their process and they will remember when they need help or whatever it is, they will give you another call.

CHUCK: Yeah. In fact, my mastermind group they got on my case about that because I was talking to them about some online training that I was trying to get sold and I was like, “Well I mentioned it on the podcast but I didn’t have very many people sign up,” and they were all over, “Look you got to have a newsletter because if they are listening to the podcast, they are probably siting in their car and they are not in the position to look it up and go sign up.”

ERIC: It’s like a mode switch.

CHUCK: Yeah. but if it you put it in a newsletter, then they are sitting at their computer, they are checking their email or you know, maybe even siting in the doctor’s office and they maybe on their phone or whatever device they listen the show on, the difference is that there is a link there and all they have to do is click it and sign up. And so I can raise awareness on the podcast, but the rubber really meets the road in the newsletter.

JIM: Yeah. And they are not likely to go for anything until they’ve heard about it a few times. You know, it’s pretty unlikely and they say like, have a need right then and there. “Oh my god, this solves my problem” to sign up and buy. But if you are reminding them that it exists, like even people who have bought my book, they were like… I’ve seen people say, “Yeah I’ve been meaning to get around to that,” or “I’m going to buy it for Christmas break so that I can read it then,” or something like that.

EVAN:  So how do you get people on your newsletter? And let me add a related question; that is for those people who don’t really wanna be on it, do you feel bad for sending them emails even if you make it easy to subscribe?

ERIC: Well, when someone signs up to get in your newsletter, then they are going to wanna hear from you. And from what I understand is when people unsubscribe is because they might not be interested in what you are writing about anymore or maybe they got on it and was expecting something different. And for the most part, in almost any case that I’ve seen personally, they weren’t my target market customer. Like there wasn’t a right fit there they might have gone on it like expecting me to talk about Perl or whatever but I’m talking about Ruby. So I don’t know, like I’ve never really had problems with that. And you know, it’s not a requirement too, like you are not saying you have to get on my newsletter in order to find my stuff.

EVAN: So I guess more specifically, you guys so it’s just you and Chuck who have the newsletter, I gathered that both of you guys are explicitly asking people to sign up  and that’s the only way you get them to the newsletter. You don’t just add people automatically somehow.

ERIC: Oh yeah. You can’t.

JIM: Yeah. Definitely not.

ERIC: I think that’s illegal or — spam or whatever it is.

EVAN: Because for being illegal, I still get a lot of it.

CHUCK: Yeah, I mean…


JIM: My Viagra sales are going very well.


EVAN: Glad to hear it Jim!

ERIC: Mine dipped a bit last month.

[overlapping talks]

CHUCK: Yeah the spam is one thing, but as far as the actual newsletter mailing list, I mean you are usually a service like MailChimp or AWeber. I use Aweber. I happen to like it a lot that. The cool thing about them is that you, by default, have a double opt-in. So even if they put their name on your list, they still have you opt-in the list in order to get it.

EVAN: Oh cool. OK.

CHUCK: And so—


EVAN: Can you link that service? I didn’t hear what you mentioned.

CHUCK: Yeah I’ll put an affiliate link in to the show notes.

EVAN: OK. So you make lots of money off of it.

CHUCK: I don’t make a lot of money off of it.

EVAN: [laughs]

CHUCK: But I do appreciate what money I can get from it. Anyway, it’s nice. So you have the double opt-in just built in and it works out well. So if they are not expecting it and they don’t read the email, then it will look like spam and they are just done. You know, they just ignore the email; they don’t get signed up for the list. If they do see it coming, either because they have signed up for your website or because you’ve told them that its coming or they just look at it and go, “Oh, this is a list I wanna be a part of,” then there you go. I’ll put a link and opt-in.

ERIC: It’s all based in your content. Like for my main blog one, basically I ask people to opt-in and what I do is I send them either, “Hey I just wrote a new blog post in my blog,” which has some information but here is some other stuff that I didn’t wanna actually make public on the blog. So it’s like bonuses content. Or I’ve had a couple of posts in the past that everyone loved, but they are from a year back so the new blog readers won’t see them. So I want to say, “Hey, if you haven’t seen this, here’s a post I did. A lot of people liked it.” And basically, “Here’s the great content that I have.” “Here’s the great things I have that are free. If you haven’t seen it, check it out.”

And so I use that and then another list I have I actually have kind of via email train people on how to do refactoring in Ruby. And so, it’s I don’t know, 8 or 9 emails that kind of step through different parts. And basically it’s like I’m kind of pitching my book like, “Hey, if you wanna learn more buy my book.” But it’s also you can just get those emails and learn how to do stuff and go off and do it on your own. So the content is the big thing about like is this a spam or does someone actually wants this content?

CHUCK: Yeah. I forgot to mention the auto responders and that is definitely a powerful way to go. Sometimes it’s also a good way get people to sign up. “Sign up and you will get these nine emails about this.” But yeah, there is the payoff too of they sign up and they get content right away. And you make that connection and you can solidify it without really having to do anything because you already written those emails.

ERIC: Yeah and I mean the background part of why I’m using more and more newsletter stuff is you have a better connection with people. I mean it’s not anonymous people. Now that you can actually when you contact them it’s in their inbox set to reply back. And I’ve sent out emails to my newsletter saying, “Hey, I don’t know what to write about. What do you want me to write about?” And would get 30-40 ideas that I go and write. you know, this is stuff that people actually wanna hear. And so I call it a tighter feedback loop than just putting something on your blog and kind of hoping that someone comments.

CHUCK: And it’s really easy for people to fire back a response because you set the reply to address and you just say, “Hey this is what I want.” And you know, it’s not this big long conversation. They just take two seconds and give you reply. So I really, really like it. I mean all in all it’s a terrific way to go. And you know, once you have somebody in there then it’s easy to (like we said before) engage with them again and again. And it’s just another way of doing that as opposed to having them subscribe to your blog’s RSS feed or listen to your podcast or whatever. If they are not committed to those things an email, newsletter is a low impact way of still keeping in touch.

ERIC: Yeah and to kind of cycle this back to like the optimization stuff, I haven’t done this idea yet, like I started on it and then got busy with a new client, but I’m getting to the point where if someone wants to work with me and they are not ready to go and they are kind of like, “Hmm, I’m not sure yet,” I’m basically going to sending them my newsletter and say, “Look, you are not ready. Check out some of the stuff I do. See some work I do. When you are ready you can contact me back.”

And so basically use my newsletter as a follow up system for them and to kind of build up their trust in me. And so it’s kind of that keeping in touch. Show that I know what I’m doing, show that I’m expert, but it’s not something I have to do all the time. And then if they are ready or not, or if they are like, “Oh, I don’t wanna work with Eric. He is not going to be able to help,” they can unsubscribe. Or if they are ready, they can reply to me and we can start the whole like let’s start project for next week type thing.

EVAN: That’s one last thing you have to keep track of.

ERIC: Yeah. This other idea I’m not quite sure if I’m going to do it, but I’ve even considered that I won’t work with a client unless they’ve subscribed to my newsletter and have seen the free stuff that I have out there. You know, if they are willing to give me x dollars, then I wanna make sure that they are taking advantage of the stuff that I’ve already given away.

[overlapping talks]

EVAN: I’ve heard of one or two crazy that does something like that that you have to have some kind of relationship with them already before they’ll even consider working with you. I think maybe was just one and unfortunately, I can’t remember so this is all completely anecdotal. Sorry.

JIM: Cool story bro.

EVAN: Thanks man.

CHUCK: Sometimes it’s funny because sometimes the relationship they have with you is totally one sided. Like you have no idea who they are, but they have been consuming your content for weeks and so.

EVAN: [crosstalk] –content. [laughs]

CHUCK: So then when they come to you, they feel like they already know who you are. And that can be the relationship that makes the difference.

ERIC: Right. And it’s just building up that trust between you and them. And you know, you don’t have to learn a little bit about them because its being one sided, but that’s something you can kind of do. Typically, it’s easier for freelancers to research an established business than it is for a business to research a freelancer just based on the information.

CHUCK: Mh-hmm.

JIM: So I’m curious like if you are going to do auto responders, you know, you say to somebody, “You got to sign up here before we go forward.” What do you have prepared? Especially if you have clients who hire you for different reasons? Like someone hires you to build a product for them, they might be thinking in terms of product. Another people hire you to help them be more agile and manage the team better and then think about those things. So you know, as far as content goes, how do you juggle that?

ERIC: Magic. [chuckles] I mean I had this problem. I’m not very focused. I have tech A.D.D or tech nerd A.D.D (that’s the proper term)  but for me, I’m trying to like define like this is the ideal clients that I work with and so I’m going to try to write stuff, make things for them and it might not actually apply to every other one of the clients that I have. So in your case Jim I know you do dev but you also do design, I think we talked about this a little bit. You know yeah you could structure your site and your content around, “I can do A and B and C and D,” but you might get a stronger response to say “I do A,” and the people who want B, C and D still might be motivated to contact you about other stuff. And so its the—


JIM: Well sure.

EVAN: The focused offering will make it easier I guess for making people more willing to actually read what you have to say, rather than when you have to say a lot and they feel like they have to read all of it.

[overlapping talks]

CHUCK: And you could conceivably set up landing pages for the different areas that you cover and then have separate newsletters for each one.

ERIC: Exactly. And like for me, because I have products in different areas, but I have let’s say about 11 different mailing lists. I have like my general Ruby Rails one, I have one for a couple of refactoring, I have a couple of HR products, a couple for writing eBooks. And so the whole point is, depending on what someone’s interested in and where they came in from, they are going to get different messages, different content and that’s going to funnel into however I want. I did a webinar about RedMine a while ago. In that webinar, I gave them different things and they get in my normal list but eventually, they kind of merged into one and if they are interested about RedMine, they will contact me.

EVAN: How often are you writing on these mailing lists? I mean these newsletters.

ERIC: I was trying to do up to a month, like two emails a month. The way its set up, like what Chuck is talking about auto-responders, so it’s not actually like it’s a — newsletter. I’m basically adding stuff on the end of a stack or whatever. And so people who just sign up are getting the very beginning.

ERIC: Right.

ERIC: So you know I think they have like 14-day delay on most of it but it’s the kind of thing though if you spend a week and write or ten emails and load it up. If you send them out once a month, that’s ten months of stuff done and you won’t have to touch it again.

CHUCK: Yeah one other thing that I’m doing or I’m going to start doing with the different shows that I do is I’m going to have a mailing list for each one. I’m going do what I’ve seen some other people do and that is basically the newsletter isn’t like this big structured thing. 90% of it will already be done because it’s like you know, here is a thanks for our sponsors, here is a product or something that I want you to see, here is an episode that’s a year more old that I think you will enjoy. And then I’ll just have a, “Hey here’s what we talked about in the latest episode. Be ready to see it,” and maybe give them a sneak peek on some of the picks or something. But all of the stuff, except for the, “Hey, here is what we talked about in the last episode,” will be done and all I have to do is write a few paragraphs saying, “Hey, here is what we talked about. Here are the parts that I liked. Here’s the one I’m excited for you to have,” and then just send it out.

ERIC: Yeah. And the other podcast I’m in, we were trying to do that so like you know, when the new episodes is out, it’s not just an RSS feed that pops up in iTunes but you get an email of kind of a summary of what it is or things like bonus things or whatever. And I have actually taken like I’ve read so many blogs, find an amazing blog post. I take maybe a paragraph about why I think it’s amazing or kind of an additional idea and make that an email. So I would say, “Hey I read this post. Go read it now. When you are done, come back to this email and read kind of a slant on it or a variant of it.” You don’t have to write all of your content, especially like in old school sharing style like before social networks came around.

CHUCK: Yeah. I subscribed to one newsletter that is effectively it comes out like every week or two and he is basically, “Hey here’s what I did. Here’s what I was thinking about. (And it’s no more than like 5 or 6 paragraphs) Thanks.” And you know the guy’s name, “Justin” and you know, basically his credentials. And so, it’s really just a convenient way of him keeping in touch with all of the folks that he’s interacted with.

JIM: So I think something good to cover would be, “What should I do?” For like people listening and especially when I hear interesting things that people are doing with their businesses, I’m at a point now where I need to optimize my sales pipeline or I need to improve it, what are some things that I should do to figure out how I get to a better step, you know, tomorrow?

CHUCK: So one thing that I recommend to people is that, figure out where you want people to wind up. And to wind up as a client is not an answer — because it’s too vague.

ERIC: Also you need to have a high volume to get one client too.

CHUCK: Right. So basically, what it comes down to is, OK let’s say that the place you want them to wind up is on your website, on your contact page. And I highly recommend that you not just have a contact page but that you make that easy to figure out how to get a hold of you on the website. But let’s just say that that’s where you want them to go. So you want them to wind up on that contact page or to call you on the phone off of the website. So you have that focus, you want them there. So then what you do is you say, “OK what’s the next level up?” Well, from the contact page, it makes it really easy for people to get to the contact page if I put a link to it on other places on my webpage, my blog or on my website or on my podcast site or however on the landing pages. So then you do that.

And this is just an example. I mean, if you want them to contact you in another way, or go some other way then that’s what you get. So then, you move up from there. Well how do I get that? Well you put it on Twitter and you put it on Reddit. You figure out what people are looking for that content. And then you can start to analyze it and say, “OK, it seems like most of the people who come in to this kind of article are the ones that are making it all the way through.” You can set up landing pages and see what you can do there. But you kind of have to build this strategy and it really depends on who your target audience is as to how you build it from, “I want them on my contact page,” all the way up to, “They are going to find my content or find my website or find somebody who knows me off and on the other end.” Because it may turn out that you’re handing out a business card at a conference or things like that—


JIM: Yeah I think that’s—


CHUCK: So you have to know who you want to find, how to find them and then where you want them to end up and then connect the dots.

JIM: I think that’s really good insight. One of the other things that came to mind as we are talking about you know, figuring out where you want them to go is I’ve heard a bit about this in a blog post about selling my book, where I was shocked to find that even though I was running this blog post and for years I’ve been running blog post that are relevant to people but they just lurk out there and read them. I added an email sign up form. Like, “Hey if you want to find out more, sign up here,” and then I write a book about this. And I couldn’t believe that people are actually signing up because I would not get many comments on my blog post.

So I thought maybe people came and then they just disappeared, but people were far more willing to just say, “All right. I’ll just toss my email in the hat. Just send me your stuff and I can always unsubscribe.” And I thought it would be easier to comment and to engage, but sometimes people just don’t wanna do that. Just send me your email. And so I actually need to do this myself, just make business for them. So if I’m writing about you know, things that are relevant to my clients that maybe are not technical, that are not related specifically to my book newsletter, just sign up here then I’ll send new content.

CHUCK: Yeah. People aren’t going to contact you either until they’ve had repeated exposure. Almost all of the clients that I’ve had, it’s either been a referral from somebody that they trust or it’s been, “Hey I watched a whole bunch of your videos or listened to a whole bunch of your shows and then decided to call you up.” And so, again if it comes down to that contact page, you put it in your newsletter, you put it in your videos; you put it in your podcast or whatever, as appropriate obviously. But yeah, you maximize the exposure and then you maximize their exposure too. You know, you make it easy for them to get to that place.

ERIC: The other thing about is kind of gradual (like you are saying Jim) like for tech people posting the comments is not a big deal. I mean we all have these accounts, we have open ID or whatever, it’s just a textbox. But for general people like that’s they are writing something on the public Internet. That’s actually a fear that people have. So signing up for email its, they are not writing anything, they are just putting their name in there. They are going to get into the list.

And then the next step if they actually reply to your, email that’s still private conversation; they don’t have to worry about, in five years this conversation being public. And I don’t get very comments on my blog, but yeah I get tons of replies whenever I send down email. And then on Twitter, I get tons of replies on there. And I think it’s just the commitment factor. And it’s like I don’t know if I necessarily want to commit to writing a comment and having every who sees this page will see my comment.

CHUCK: Yeah. And it’s interesting because when we do a lot of the stuff, we’re thinking from the perspective of, “Oh, what would I do?” But ultimately, if we are trying to provide a service to business people who can’t quote themselves their own website in Rails, I mean they are completely different demographic than we have to be able to cater to that — and I think that’s a lot of what Eric is saying. And so, you have to be aware of that. You have to be aware of the steps that they are willing to take to get there and not necessarily the steps that you would like them to take or you think that would be convenient for them to take.

ERIC: Yeah. I know Evan you do a lot of start-up stuff. So in general, start up or start up audience is going to be more sophisticated. They will probably be more likely to leave more comments or talk about on Hacker News, but for me if I’m targeting the HR audience, it’s like there is not going to be very much public discussion at all.

EVAN: Yeah, very different users.

CHUCK: Yup. All right well I think we’ve actually gone almost a full hour talking about this and we need to get into the picks. But I wanna make sure that we’ve covered everything. Are there any other aspects or anything that we want to talk about before we jump over to picks?

ERIC: There is one thing I wanna do because this is optimization and its marketing optimization so it can be scary. If you don’t do anything at all, start with (kind of what you were saying earlier Chuck), figure out what you want people to do. Like figure out your ideal pipeline, like the steps you wanna take. And to get started, focus on one of them, probably one of the earlier parts of the steps and figure out what you can do to optimize that one. Because basically, as just some development, as you optimize one method call, it’s going to make the overall thing get better and get faster. And so pay something small, start small and try to be programmatic about it and try to say like, “OK I’m going to work on this stage, improve it by 10% and then I might come and work on different stage.” And you just iterate over that and eventually you get to a point where like, “Yeah, I’m happy with my marketing now.”

CHUCK: Yeah. One thing I wanna point out though is that it’s very hard to optimize something if you are not measuring it. So, if you know what the next step is, for example if it’s from reading a post on my blog to signing up for my newsletter, measure that. Measure how many visitors you are getting and measure how many of those are signing up for your newsletter. And then play with it; tweak it. See if you move it up higher on the page or change the colors or put an image behind it or whatever, but figure out these different changes and see what works to make that better. If you are not measuring that, you won’t know it. Anyway, let’s do the picks. Eric, what are your picks?

ERIC: OK. So I have one pick and then I’ll add one based on this discussion. So one pick that I have used actually today and the past couple of weeks is BrowserStack, basically lets you run multiple browsers and in OSes in a browser. It’s great for basically testing IE stuff and what version of IE do you want. IE 6, 7, 8 that sort of idea. It’s paid service. It’s pretty inexpensive. I think you can go like half now are free. But like just today I loaded up IE8 and IE9 for a client and run our Jasmine test just to see like is stuff really broken or is it just partially broken. And it’s a great service if you want to mess with having Windows VMs or Windows licensing or even having hardware around. So I recommend it. It’s been really nice for me.

And then my second pick based on this conversation is this called PipelineDeals. This is a simple one. I basically track context. So in this point, I guess considered leads, I’ll track if they have projects for me, I’ll track what the stages are or where they heard of me from — all that stuff. And it has some nice reports and actually sends up stuff every Monday — actually every day and also every Monday — so I can keep track of who I should follow up with this week. So it’s PipelineDeals and I’ll put the link in the show notes.

CHUCK: Cool. Evan, what are your picks?

EVAN: I got nothing.

CHUCK: Jim, what are your picks?

JIM: Terrible, terrible Evan. I have one pick because I couldn’t think of any picks. And that is


ERIC: What does that do?

EVAN: Are you saying this is that better than mine?

JIM: [laughs] It’s better than Evan’s because I actually gave you something.

EVAN: It plays this. [sad trombone sound]

CHUCK: I just clicked play too. You guys couldn’t hear it but it went on to the recorder.

EVAN: Oh. Yeah we are having really good picks today.

JIM: I don’t know about you guys.

CHUCK: Yeah. Well I’ve got a couple of picks. I’m pretty sure I’ve picked some of these before, but I’m just going to share them again because they are relevant to this. The first on is I like it better than Google analytics. It’s easier for me to read, it gives me all the information I want, it’s basically in real time and it will actually tell you how many people are on your website at a given time and things like that.

EVAN: Actually, Google Analytics as it turns out does that. I didn’t quite make this a pick, but I brought a Nexus 7 lately to use as a book reader because now it’s better than the Kindle Fire and it cost about the same. And the Analytics app on there actually does give the number of people at your site around at any given time.

JIM: Yeah Google added that recently. GetClicky had it for a couple of years.

CHUCK: Yeah. I like GetClicky so I recommend them. Another one that I’m going to pick (and I’ve already mentioned them) is Aweber. So if you are looking to create a newsletter, they have a whole bunch of templates and stuff that you can use or you can just put your own HTML in there and that works too. So, I like their stuff. It works pretty well. And my last pick is something that I figured out I can do with my iPhone…


EVAN: Make phone calls?

CHUCK: (I got an iPhone 5 by the way.) No it’s the… It does do phone calls actually. [laughs] Sorry my brain totally just skipped over that and then came back to it.

JIM: Phone calls, there’s an app for that.

CHUCK: Anyway, Omnifocus on the iPhone.

EVAN: Yes.

CHUCK: It has this little feature that you can turn on that when you create a reminder with Siri. [overlapping talk] I love it.

EVAN: I mentioned that one several episodes ago. So, you are welcome. That’s basically what I’ve been using Siri for more than anything else is I create reminders and they go in Omnifocus. I do it when I’m driving.

CHUCK: Yeah. I do that too. And it’s funny because I’ve had this thing for like two weeks and I’m addicted to Siri and Omnifocus. [laughs]

EVAN: I don’t know if Siri actually work with the–

CHUCK: Yeah, sometimes it’s really hard to get it figure out what you are talking about, but most of the time, its close enough and so I just let it suck in to Omnifocus and if it bugs me when I’m looking at the my to-dos later I’ll fix it.

EVAN: Right. So I will look at my reminder and go, “OK this is Siri misunderstanding when I said ‘bra’.”

CHUCK: Yeah.

EVAN: Which is most of the time. It’s really pretty bad.

CHUCK: It is bad. But it’s so handy.


JIM: I realized I have a pick.

CHUCK: You have a pick?

JIM: I have a pick I forgot about it. Have any of you seen the POP App? Its and it’s for designing interactive—


EVAN: Oh, yeah, yeah, yeah. I know about this one.

JIM: Really cool app. You basically just sketch out a screen like for doing iPhone click throughs or something like that and take a picture of it with the app, and you can set areas to be clickable and then you can take a picture of the next screen. So you can just literally sketch something out. You don’t have to do go to a computer. I know people like Balsamiq and things like that—


EVAN: –your application via drawings.

JIM: Yeah. So you can write it down wherever you are. When you get back where you can grab your phone and actually make it clickable. So really cool app.

[overlapping talks]

EVAN: I remember which … so you have basically no reason not to try it.

JIM: Yeah, it’s free and then I think that they’ll have like a sync in service so you can store some of the app (I don’t know what they call them) projects or something and then if you want more…


EVAN: That’s really how they expect to make money off of it? OK.

[overlapping talks]

JIM: It’s pretty cool.

EVAN: Yeah. Apparently I haven’t looked at the website. I’ve just read a little bit about it somewhere else but it’s got some really nice demos of it.

CHUCK: Cool.

EVAN: That’s a good pick.

CHUCK: All right well, you interrupted me, but I was done.


JIM: I sense its coming.

CHUCK: You could feel a disturbance in the force, huh?

JIM: [laughs] Exactly.

EVAN: No. The Star Wars quotes are all mine.

CHUCK: [laughs]

EVAN: Right.

CHUCK: All right. Well, we’ll wrap this up and we’ll catch you all next week. Thanks for listening. Here is the sad trombone to send us away.

[sad trombone sound]

[end of podcast]

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