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Season 2, Episode 6

Making Sales Less Painful Through Marketing

Episode Summary

Today we’ll be discussing sales and marketing and how to use marketing to improve the sales experience as a freelancer.

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  • Erik Dietrich
  • Meg Cumby
  • Marg Reffell
  • Reuven Lerner

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Episode Transcript

Reuven: Hi, everyone, and welcome to the Business of Freelancing podcast. Today we’ll be discussing sales, marketing, and how you can improve your chances at successful sales through marketing.

On today’s panel, we have Meg Cumby. 

Meg: Hello.

Reuven: Marg Reffell.

Marg: Hello.

Reuven: Erik Dietrich.

Erik: Hi, everybody.

Reuven:  I’m Ruben Lerner. So Erik, you recently published a blog post with the title Sales 101 for Freelance Devs — Avoiding the Pain You’re About to Experience. So tell us what pain you predict people will be experiencing? Set us up with how they can avoid that pain?

Erik: Sure. So it’s a long sequence of pains. I based this on my own experience, and just observing a lot of people, the people that write in to me with questions. It starts, like, there’s a sequence I can imagine happening in my mind, you decide to hang out your shingle and go out into business on your own.

One of the first things you do is this form of networking, where you go to everybody that and say, “Hey, I’m off on my own now. Can you enlist me if you need business or recommend me to your friends or whoever.” The post goes into, I won’t get into the weeds of it here. But the post goes into what you’re really doing there, which is creating this uncompensated affiliate strategy, where you’re enlisting people to go do affiliate sales for you, meaning, in theory, you’re giving them some kind of commission, but you’re really giving them nothing.

You’re just creating this uncompensated sales workforce, and you’re calling it networking. The pains come when number one, that’s not going to be super effective. People genuinely want to help you at first, but that peters out after a bit. Number two, those are going to be badly qualified leads meaning if like in my world, where it’s freelance application development, you’re going to have your aunt or something is going to recommend somebody who needs a computer specialist. 

It’s going to be somebody that wants you to come and fix something with their hard drive. It leads to a lot of friction and inefficiency in your sales pipeline. Then I  go through what it’s like to say, go to labor brokerage sites, like Toptal, or Fiverr, or Upwork, or whatever, and put yourself there. Then you’re in these sales conversations or sales processes, where you’re all competing to be the cheapest, and that’s not a lot of fun, either. So maybe you start doing warm or cold outreach, which everybody probably hates doing cold outreach. 

So it’s just all these different things that I walk through, what the typical journey includes, and how it goes poorly, and all that. Then I round out the post by basically saying, sales is, when you get down to it, it’s really like you could model it with a Kanban board and say, you’ve got leads, then you’ve got qualified leads, and then opportunities in closed like a business that you’ve won. 

In each of those steps, you can have a process and you can try to move people along in a way that makes sense for both of you. The best way to do that is to ensure that you’re having conversations only with people that will be a good fit for your business. So, the best way to make sales work, the best way to make sales painless, is to ensure that you’re bringing qualified leads to you, you’re helping prospects find you and self-select based on your ability to help them rather than you  doing a poll where you’re going out to the world and recruiting business for lack of a better word. 

So, as I understand that, that’s the genesis for the topic here. But that was the blog post is like, “Hey, I’m going to write all about sales, how it works, and then dot dot, dot, I’m going to later talk about marketing, which at the risk of tipping my hand is the strategy for bringing leads to you.”

Reuven: One of the things that really sticks out in the blog post is the number, the stark numbers that if you start doing lots of outreach, warm outreach, cold outreach, talking to people, that even from among those qualified leads, the number of people that you’re going to get who are really going to engage with you and really going to hire you is small.   

If I had known that back when I started, I would have been really surprised or upset. Now I recognize Okay, it’s a big world out there. But part of the post seems aimed at increasing your odds, improving the odds that given your effort, the maximum percentage of people you reach or that hear about you are going to be indeed be qualified leads and are more likely to reach you and then not waste your time. Best ROI, the way to summarize is like get a good ROI in your time investment.

Erik: Yeah, absolutely. Writing about this was modeled on some sales work that we’ve been doing with Hit Subscribe, we experimented with some cold outreach to well-qualified prospects. We basically identified companies who could definitively use our help, and that we thought would be well qualified. Even in those scenarios, when you’re doing cold outreach, the conversion rate on that is atrocious. 

If you’re listening, and you’re doing cold outreach, you’d be lucky to get 1% on a sales call, lucky, that’s a great… When doing cold outreach, you start celebrating, whether, somebody writes back and just tells you to get lost, and you’re like, “Hey, and they responded, that’s a win.”


So, we’ve learned a lot about, the poor odds, and what tips those odds in your favor. For instance, if you’re doing cold outreach to a well-qualified prospect that you could help, and they’re having a bad week, or they’re just not thinking about that right now, it’s over, you’re done. So, yeah, absolutely. When I say we’ve run an experiment with cold outreach, that’s not really normally the way that we acquire business.  

When you’re doing cold outreach, and your qualifying prospects, that has a bad conversion percentage, but even warm outreach, or even honestly, inbound prospects can have pretty bad conversion percentages. So you think of sales is like this funnel, where each step, some percentage of people will move on to the next step? There’s four steps there.  

If you do enough of it, you can start to quantify what your percentage of conversions in each step is, and then start to tune that. So, for me prospect generation, and bringing in prospects is really about, it’s almost like you’re reverse engineering, the sales call, like, what would make for the easiest possible sales call? Somebody coming to you and saying, “I badly need your help right now.” Then so how do you create that situation?

Meg: What you said, It’s exactly, even if you were reaching out to people that you’d be a great fit with the chances of you reaching out exactly when they need you, is so darn small. To just reaching out, and say like, I’ve been on the receiving end of a couple of cold pitches, and ones that were trying not to look like cold pitch, look like they were trying to start a relationship, but they jumped to the “Well, if you’re looking to work together.” After two interactions or something like that, I’m like, “Oh, just puts the… Oh, so you’re not looking to connect and actually figure it out. You’re just looking to get to the next step of the sale, which makes me not trust that you’ve got my best interests at heart.”

They might have my best interest there. But it’s just that it’s never… The likelihood of finding that match is so damn small when you’re doing the cold outreach, as opposed to if I find you through something you’ve written or marketing, and I’m sure we’re going to talk more about this, and then reach out to you, well, then it’s the other way around.

Erik: So, I don’t know what it is maybe other people are experiencing this with the economic downturn, the pandemic, but I don’t I get 10 pitches a day through LinkedIn. It’s like, so saturated. So even if somebody really could help me, it’s so overwhelming that I don’t respond to it. I was just thinking what you were saying with the idea of like, “Oh, I want to start a conversation.”

Now, if I get somebody send me a connection request or I accept it or something, and the first thing they do is like, “So, what’s going on with your business?” I almost find that worse than somebody who just sends me a pitch because I know, you’re going to waste my time and then make a pitch instead of just making a pitch.

Meg: Exactly.


Meg: The ones that wrap it up. I’d love to see how we could partner together. They seem like they might be a fit for my services.

Reuven: Oh, my God.

Erik: Oh, the reversal.

Meg: They make it look like they’re going to hire me. I’m like, “Oh, yeah, sure.” Then like, “Oh, no.” That’s you’re looking to sell to me, I get you. Okay, I’m glad I got on a half-hour with a call with you and just like, no.


Erik: For anyone listening, this is the kind of thing you’re up against with cold outreach. Warm outreach is a different thing because that by definition is people so they’re going to be polite, but that style of going out to get business labor brokerages outreach, some of the things you might do advertising like these can be, they’re pretty frictional. 

So you can get more people into your sales pipeline with these strategies, or at least get them on your Kanban board or whatever. But the rate at which good things happen later on in the process like conversions and that being a good customer is a lot lower than if you have business that’s coming to you and saying, “I need your help.”

That not only is a lot less work for you, but it tease up a strong negotiating position. What will tend to be a more productive relationship than if you’ve answered some RFP and one by quoting a lower rate than five other people and establishing yourself as the cheapest, who really needs the business. That usually doesn’t kick things off to as promising and start. So there is a strong motivation to get business to come to you. Now, if only it were that simple, I recognize that it isn’t.

Marg: Mm-hmm. It’s super interesting because I never have done cold outreach. So all my business has come from referrals and referrals are warm and very hot if not just warm, because they’re coming for people who have already worked with. If I were to start, ideally, if I already have warm referrals, I wouldn’t need to start reaching out to cold referrals unless I was completely switching demographics. 

But if I were to start, and for anyone out there trying, going, and reaching out to people in a cold outreach situation, is there a flow that you’ve seen, that works a little bit better than others? I know, we’ve mentioned like, what not to do, like, don’t monopolize people’s time, and then just switch it on. Also not don’t come out of the gate with a pitch. So where’s the happy medium of respecting their time, but also not going in and asking for the sale right away?

Erik: In my opinion, so just full disclosure, cold outreach, whether it’s through Hit Subscribe, that was an experiment we were running that I don’t think proved to be worth our time, we do much better with inbound business. So we’re shifting focus on that, it was just something we were trying. Whether it’s even through my management consulting over the years and freelancing I never… I was the same, it was all referral word of mouth, inbound. 

So I don’t personally have a great sense of what works and what didn’t, we did document what got better open rates. The thing that we found was at least open rates or people responding in some way that wasn’t, get lost, it was like, “Oh, I appreciate this. But no thanks.” It was always when we were doing something like leading with some value. So for instance, recently, GitHub changed their official terminology for any of you out there in software development from Master repo, I forget what they’re using now. But we…

Meg: Main, I think.

Erik: Main? So what we did was, we built an internal utility, that we already have something that goes and checks for outdated content in various forms. We added something to it to go check for these terms that were being deprecated. Then we send pieces of outreach to say, “Hey, this is something we do for our clients, but we’re testing now, we’re running it on prospect sites, by the way, you have a bunch of pages here that all have this term, Master on them, you might want to switch. Then this is what we do, who we are, etc.”

That got a pretty positive response. So, number one, if I were going to give advice and be lead with value as much as you can, and number two, don’t be disingenuous about what you’re doing. So like, if I were writing pieces of outreach, I’d say, “Listen, I would love to have your business, my goal here is to grow our business. But here’s the thing we found so,  you’re welcome to it and the results if you want to get on a sales call, and all that great, if not, I understand.”

So those would be my pieces of advice is try to add value in every communication somehow or another. Don’t try to pretend you’re not trying to sell them, you’re not doing this cold outreach because it’s fun.

Reuven: I can tell you I tried this about many years ago, I tried doing cold outreach. It was an abysmal failure, absolutely, completely terrible, and turned me off to ever trying again, till about a year and a half ago, when I said, “You know what, I’ll try it.” I was working with a coach on these sorts of things. He was like, “Yeah, this looks great. This looks great.”  I just sent it. Again, and again, I was using the lead navigator on LinkedIn to find the right people, and basically, nothing, nothing at all.  

What I heard was basically what Erik confirmed on his article, and you guys speaking now as well, which is, you need to follow up tons of times, you need to send lots of mail, it becomes a huge time sink to make it effective. At some point I just threw my hand and said, forget it. I actually recently decided maybe I’d play with it again just see if I could tweak it a little more and use the advice that I’ve heard here and there. 

I actually started listening a little bit to the Cold Email Outreach podcast, which is about this. I keep thinking all right, like are their suggestions really that different from what I was doing? Maybe, maybe not. It seems like super, super subtle tweaking, combined with lots of time, lots of email, lots of follow up. I have decided to give it a shot, but I would not be surprised if, within a few weeks of trying it, I just give up because it is so time and energy-intensive.

Erik: Then you start to… I remember talking about this in the post, you start to… Believe it or not, somebody’s listening out there, you start to understand the spammers that send… With the wild card placeholders left in place, like, dear prospects or whatever. You start to understand that, because you spend countless hours crafting these messages and saying, like, “I’m not going to be like a spammer, I’m going to send this personalized message.”

You spend hours and hours sending hundreds of these and you never hear back. Then you’re like, “This isn’t really worthwhile.” Unless they were to somehow really automate it and just be able to blast out thousands of them in five minutes. Then you’re thinking, “Oh, man, what did I just send?”


Reuven: You have invented spam.


Meg: Yeah.

Erik: The path of spam don’t send.


Meg: Not only is it super time-intensive, but I’m having flashbacks to my first summer job in college of being a telemarketer. Just the feeling of rejection, day after day, after day. Out of 160 pickups, I was expected to make 6 sales, so being told no 160 times a day [laughs].

Reuven: Oh my God, Oh my God.

Meg: So, I would be doing the same with a business that I actually care about as opposed to something like a telephone company [laughs].

Erik: Here’s a depressing thing, too. Hopefully, this doesn’t apply to those of you listening. But if you’re a freelancer, and you’re getting to the point of doing cold outreach, a lot of times you’re not doing that from a good place, like you’re back into a corner, and you’re doing that because you’re just not having lead gen success in other places.  

In a sense, that’s almost the worst time to be doing it because you’re desperate, and that’s what puts you there. It’s not a great strategy, it’s a number of strategy. If you send out 1000 pieces, you’ll probably get a piece of business, but probably not less than 1000. So they’re really speak to what I was trying to leave off within the post, which is, there is a lot of pain in these types of approaches. 

If you’re bringing leads to you, if leads are seeking you out, it’s so much better, not just from a time perspective, but you’re going to have better sales calls and all that but a morale perspective, too. It’s not this depressing. I can’t even imagine being a telemarketer, that’s got to be a real-life experience for you just hearing no all day, every day, and probably hostility, right? Were people angry all the time?

Meg: Oh, terribly. I’m really nice on the phone. But they still didn’t like me [laughs].


Reuven: I spent two hours on the phone in college doing fundraising for Hillel for the Jewish group with alumni, and that turned me off to doing that thing forever. It was very, very rough. Again, these were alumni who liked us, who remember us, and still no one wants to get these sorts of calls. I’ll add, by the way, Erik, in the article you’d mentioned, going through middlemen. I don’t think it’s necessarily, it might not be a career expanding strategy, it might not be the best way to go forever. 

But a place like Toptal, I definitely know of people who have worked with them for a while. It’s basically like working for an agency, where they more or less provide you with steady work, you’re never going to get rich off of it. You’re never going to have your own independent branding based on it. But it’s not a bad way to go. I can tell you also, I actually spoke to Toptal a few years ago, and I interviewed with them just to see what it was like.

Their interview process was weird and brutal. I did not make it through there. They asked me all sorts of things about super tiny algorithmic stuff that I don’t care about. But I do know people who have been pretty happy working that way. I don’t see it as my career move. I don’t think it’s what most people who become freelancers want to do eventually. But it’s not a bad thing to have in your back pocket when times get slow to have someone putting out feelers for you.

Erik: Yeah, that’s fair. I don’t remember exactly what I was going into. In the post, I talked about a recruitment model and those types of brokerage sites and using that as your sales funnel. The thing that I would say there is if you’re looking to create and grow a business, you’re essentially outsourcing your whole sales process.  

The nice thing about that is you give it to them, and it’s low effort. They’re just bring people who are interested in you, and then you answer an RFP. The tough thing about that is, well, I would say it’s multifaceted, but it’s going to make your sales calls different, they’re more like job interviews than sales calls. So, when you win that business, you’re usually going to get negotiated down on rate, the brokerage sites taking a cut, and then that client is probably going to view you as a staff augmentation rather than a partner. 

So it comes with all those downsides, but it’s better than not being able to pay the rent. So yeah, that’s true, and it does bring you potential warm business.

Marg: That brings up a good point, with those sites, too. I wonder if we were to think about what the top four to five ways of getting clients are. If we could, for the audience, and this might change person to person, but rank them, like, ideally, these are your best kind, and then something that I imagine would be close to like cold calls would be close to the bottom. 

Yeah, so if I was to take my first shot at ranking them, I would think that like direct referrals from people that you’ve worked with, directly, and then removed referrals. So people that have maybe don’t know, anyone that’s worked for you directly, but are aware of your reputation. Then these agency sites, and then cold calls, but I’m wondering if there’s anything in the middle that I’m missing as well?

Erik: Well, I would throw content marketing in there in whatever form, it comes, probably somewhere below a direct, like very warm referral. This is just thinking through the data that I have. Warm referrals, absolutely the best, indirect or that might be on par with content marketing, because I’ve had great luck with content marketing over the years when I used to have this niche management consulting practice that was based around static code analysis.

Sometimes talks to user groups, or I would write a lot of blog posts, sometimes on static analysis tool sites about pretty niche topics. That would result in a lot of business that would be like, “Hey, I read this study you did about X, we’re having this problem at our business. Can you help us? And the reason that I’m putting that so high up there.” So, there’s nothing better than the referral, because that’s the same like you have an actual human that’s saying, “Hey, Erik, can really help you.”

So it’s kind of the one-two punch, the content marketing is, nobody’s telling them that, but they can see it for themselves. So that exists, but the gotcha with content marketing is that you almost can’t do it as a generalist, or it’s really hard as a generalist, you need a specific thing that you’re selling.   

I’m open to being wrong in that. But I run a content marketing business and do content marketing strategy, and I don’t know how I would content market a generalist practice. But yeah, so not to get too far off the rails, because that’s the one I would inject in there, between any form of active reaches this content marketing.

Reuven: I would add one more thing in there, and I’m adding in because I’m trying it now, and I’ve no idea how it’s going to go. So, you guys know, well, just before the pandemic, I used to go to China a bunch of times a year. When I was going there, I was going through a training company. So they were doing the sort of taking a cut. So I told them in a mark of genius timing, on November 1 of last year, I’m setting up my own Chinese company, I don’t need you guys anymore, so long. 

Okay, perhaps timing could have been better. Regardless, I’m now back on track to set up this Chinese company of mine. I’m going to try two things to get sales for and basically just like me, represented in China, selling my online courses and in-person as well. 

One of them is going to be I’m going to hire a manager there of my Chinese company whose job will be to do cold outreach and to take warm leads that I get from the like, for lack of a better term incubator that I’m working with, that will take these leads cold and warm, and then work with them. The other thing is earlier today, I agreed with some people who have a lot of contacts there to provide me with warm leads. 

So this is like having someone on staff working with cold and warm leads, they’re not spending my time, they’re spending my money and their time to hopefully get over that hurdle of cold outreach being a time sink. How well this will work? Time will tell, I really have no idea. But I hope this mix strategy will pay off in some way.

Erik: So there’s something I would say crucial there. That’s a good strategy that I’d personally put a little bit above executing your own cold outreach. I don’t know if I would put it above content marketing if we’re ranking them. But putting my management consulting hat back on, if you are having somebody else that is perceived as a subordinate, like an employee, if you will, executing outreach, well, you have a sales organization. 

So when you get on the call the fact that you have somebody doing demand generation of a form, you’re supposed to have that in the business. So you get this subtle but important, power, dynamic thing that happens. If you’re executing your own cold outreach, you are perceived as desperate, if your employee is executing cold outreach, you’re the CEO and sales is doing what sales does.  

So, it’s not quite the same as if they’re coming and seeking you out. But when they’re talking to you, it doesn’t seem quite as needful. So, if you’re going to execute a cold outreach strategy, and you have some budget, getting a VA or something to do that is probably worth doing.

Marg: Mm-hmm. That’s interesting, out of curiosity, Reuven, and I don’t need exact numbers. Would they get paid a set rate? Or would they take a commission on the sales that come out of that?

Reuven: The employee that I’m probably going to be hiring, I told the incubator, I spoke to them a little bit about… They said, “Well, if you want hire someone, we can help you find someone. I said, “Great, what’s the salary?” They told me probably I could expect to spend about $1,000 to $1,500 a month on salary to have someone mid-level or semi senior. I was like, “Done.” I will totally do that. Because basically, if I pay that for a few months, either it’ll pay off, or it won’t, it will be pretty clear, pretty quickly.

With the outreach company or the lead company that I spoke to today, what they want is the equivalent of $300 a month in terms of a retainer, to make all these introductions, and then a 5% Commission on whatever leads they bring me. I figured that’s mostly fair, I just asked them when I emailed them back today. I said, “Can we limit that to two years, I don’t want to be spending like 5% ad infinitum, and assuming it takes, let’s say, up to a year for a deal to actually happen.” So a year to two years of paying them off for that seems reasonable.

Erik: There’s another one that occurs to me because we might be doing that. Somewhere, I would think above the outreach below any of the marketing-oriented tactics is just paid advertise. It’s weird to think like, is that really getting prospects to come to you? But in a sense, it is, you go through LinkedIn advertising, Facebook ads, display ads, whatever it may be, bring them to a landing page. Then if they’re interested, they’ve clicked, and then they’re reaching out to you. 

We haven’t really done any of that yet. I don’t think I’m trying to think back. But it’s another thing that if you’re operationalizing, what you’re doing, and you’re working towards having an established presence, that’s something that clients will expect, businesses advertise. So that’s another way of doing it. It’s expensive but not really expensive.

Reuven: Have any of you have successfully done advertising before? Because I’ve tried it, and it’s had very, very mixed results.

Erik:  No, I haven’t historically, although that’s part of Hit Subscribe 2021 plan. Full disclosure, one of the things I’m looking to do right now is, towards the end of the year, bring out a full-time sales staff, so that’ll probably fall in that department. It could work because what we’ve learned as for our business, content marketing for developer tools companies, they all need it, like sooner or later. It’s really a question of just being top of mind when they decide they need it.  

So for things like that advertising, and even like the right like hello, outreach that isn’t trying to make a sale. It’s almost like, “Hey, I know you’re going to need this sooner or later, and I just want you to think of us when you do.” So I haven’t personally made it work, but I think that visibility and mindshare is really what it gets you. 

For a freelance business, I don’t think that’s as easy to execute. Like, if you’re doing freelance web development or something. I can’t speak for anyone else, but people from offshore firms or whatever, reach out to me like six times a day saying, “Hey, if you ever need freelance app Dev.” 

So, that might be tougher, but if you have something that’s a little more niche, advertising, not even just for the direct sale, but so they know who you are, can be effective. 

Marg: Yeah, I’ve never used it for high touch services, but I do have an ongoing ad per day on… It can be really effective on products, maybe more so than services. So I have an Etsy shop that has website terms and conditions, shop policy, privacy policy that I put together with my lawyers, so people can go on and purchase those.  

Etsy has an advertising program. So for $5 a day, which is pretty, totally reasonable. You get bumped to the top of those search listings, and there’s not a huge competition for those. So there’s stuff like that, it’s low effort as long as the amount that I’m spending, after it’s initially made, I don’t have to touch it. So after it’s already done, I spend a really low amount of money. 

If I can sell two or three per day, then it’s one of those set it and forget it situations. Ads have worked well for that. I don’t know, I’ve never used them for high touch services, so that might be a different story.

Reuven: Yeah, I agree. I can’t imagine advertising services. I have tried advertising products, like my info products and courses, that has not really gone over so well, and it might just be because I’m bad at the advertising thing. What I found worked well was advertising free email courses, and then having them come signing up. Then after the email course, they’re dumped into my mailing list, and basically, after a few weeks or months of being on my list and saying, wow, this is good quality, this is what I’m looking for, then they sign up for course, but it’s a long play. 

Moreover, Facebook has this thing called lead ads, where it can be you click on it and Facebook basically takes the form information, and email address, country, whatever, and sends it directly to in my case Drip and signs off to your mailing list. So I found that was incredibly effective at getting subscribers, but they were completely disinterested subscribers, they never actually pay attention to the mailing list. 

Whereas if I had the ad, take them to a page about my mailing list, or the freebie and there they signed up, many fewer actually signed up, but they were more engaged, and they then did actually pay. So as I said, it has to be a long game. I’m actually thinking recently also, Oh maybe I’ll play with advertising again to see if I can get it to work because people do get it to work, but it just hasn’t worked for me so far.

Erik: What’s interesting to me about what you just said there, it’s a distinction I’d probably like to call out for people listening is, when I’m talking about content marketing, at least if it’s like me five or six years ago, I think of content marketing as Oh, you create blog posts, or maybe YouTube videos or what have you. So you create this content, and people consume it, and that’s your marketing. 

But Reuven, what you just described is just another flavor of content marketing that people might not think of in those terms, where you do something that gets you contact information for a person, and then you do what’s called lead nurture, which is, so if somebody’s willing usually gives you their contact information. Usually, you would call that a lead, it’s somebody who’s interested enough in you to trust you with that.  

Then there’s this form of content that you create, where you’re not trying to sell them stuff. You’re eventually trying to sell them stuff you’d like to, but you’re continuing to drip out content. So whether that content is just blog posts, and they follow you on your site or follow you on social media, or if it’s that they signed up for some free email course, and then you keep them warm as a lead over the years. All of that falls under content marketing.  

It’s all really when you get down to it about providing value in exchange for staying top of mind. Like it all goes after, I want you to think of me when you have a need. I recognize that that might not be right now, but when you have that need, I hope you’ll [inaudible].

Reuven: That’s why I woke up this morning, and much to my great pleasant surprise, I found that someone had bought five of my courses, I was just like, “Wow, what is going on?” So I said like, maybe he just discovered my blog, or my YouTube channel or my mailing something? No, he’s been on my list for years. He bought something from me three years ago. I guess for whatever reason, he decided, Okay, now I have cash, I have the interest, I have the need. So I was the place that he went to buy from.

Then it’s also a numbers game, the more people you have, the more likely it is that someone’s going to buy, then to just keep increasing sales like that.

Erik: You know what else? This is going to sound like the most obtuse things ever, but it’s a joke I’ve told but a serious joke. A lot of getting businesses is just staying in business long enough for people to figure out they have a need, like, I can’t tell you how many clients for blogging or whatever from years ago, just reach back out and they’re like, “Hey, are you still a thing? Like I have a need now.”

So like, even if you just like let everyone know what you’re doing, and you’re discouraged because it’s like six months in and nobody’s calling you. Sooner or later someone will someone two, three years down the line will be like, “Oh, right. Doesn’t this person do X? Hey, are you still doing that?” So, a lot of businesses is just surviving so that you’re around with their need.

Reuven: So it’s funny you say that. There was a company in Tel Aviv where I did some courses for them. I see now, four and a half years ago and every year so, I would email the training manager and say, “Hey, you need any Python courses?” “No.” “Okay, that’s fine. That’s fine.”

Two days ago, she calls me and says, “We need courses desperately now, what can you do?” What, really, really? So, you never know, you never know where it’s going to come from, and keeping those leads warm, it turns out it pays off.

Meg: Thinking too just taking a different angle on that, like when you talk about doing content marketing, and especially if you’re like me, and you don’t have an audience of your own that’s large yet, or at all. Then that whole idea of borrowing other people’s audiences or appearing on other people’s podcasts, writing a guest article, even if you don’t get something right away. You might think I’ve got nothing from it, I still get people clicking through my site from a podcast I did back in 2017/2018. 

It will still pop up, the people are still finding it, that content is still there. It’s there for people to find it when they’re ready. So if they’re searching, how do I get testimonials? That doesn’t go away unless the other person deletes it, it’s not going away anywhere, it’s still out there working for you after you’ve done that. So, again, yeah, that’s what we’ve been talking about making yourself so that you can be discoverable when they’re ready to discover you.

Erik: Thought of the angle of guest appearances, another flavor of content marketing. For anyone listening, there’s a lot of content marketing ground and plays, you can cover. If we’re going to roll up content marketing, in general, it’s basically like putting yourself out there with some focused expertise and just try to make yourself as ubiquitous as possible, and in a way that doesn’t seem scummy, lack of a better way of putting it.

Share your opinions, but not resign yourself to the fact that you may go on a podcast and talk about something you’re an expert in, and it will provide no leads, that’s possible. If you’re willing to do it anyway, your heart’s in the right place, like go share your knowledge and expertise, I promise you on a long timeline, it will pay off. But do it without the expectation like don’t go in and say, alright, I’m going to go on this podcast and then get five leads, because people will sense that you will seem off-putting. 

So it’s about having this expertise making ubiquitous and public, but being genuine about like, you’re actually helping people with this content.

Meg: If they listened to nothing else, or looked at nothing else, or never contacted you, again, they have something valuable that they’ve walked away with and their life is better for having spent their 25 minutes, 30 minutes, 40 minutes of listening to you, that they’ve got something too. 

Yeah, absolutely, you should. You can tell if somebody’s going in with the end, if you want to learn more pay for this thing. Let them take that next step if that’s what they need, but with that, still, you can mention those things, but the intent should not be selling the thing it should be providing value and building the trust. 

So that if they do need more, they seek out what you have to offer that’s maybe not free, or other things you have free or either way.

Marg: Mm-hmm. Yeah, and I can also say, like 100% from a customer because even though we’re talking about clients, we’re all still customers of someone else in different capacities. So when I try to think about my experiences of finding experts, I go to where I’ve seen those experts before. 

Sometimes that was like a year ago, sometimes I’m like, Oh, I need help with this, but I remember, I saw this YouTube video or listen to that here, and this was the person. So, I’ll go back and look for it to find that person. So don’t underestimate how you can position yourself over the long tail as well. Because I know myself, that’s how I seek people out as well.

Meg: I don’t know if this will seem out of left field or? One of my really good channels of connecting with people, great clients that we work really well together was meeting people at conferences. That’s really not an available like meeting people in person, and with the intention of going there just to connect with other business people and the intention of just leveling up our businesses.  

It just so happened that there was a fit to work together and yes, you get talking. I’m wondering what the replacement for that sort of channel would be like making those relationships and connections without that like serendipitous meeting that we can’t have necessarily right now, during pandemic times. 

Erik: For me, I’ve discovered some community Slacks like, there’s a Slack I’m in for content marketers. Even though a lot of the folks in there would theoretically be Hit Subscribe’s clients, I don’t go in there and try to sell them anything, it’s for me a way to learn what interests my buyers and then to exchange ideas to learn things, etc.  

So I feel like there’s a pretty strong analog between that and going to a conference where it might be a mix of people who are either competitors, or peers, or customers, and you’re all there together, operating in good faith. So Slack and Facebook groups, to some extent is another one in the virtual either these days. By the way, that’s a great point, like in the theme of the episode, how can I help prospects find me on their own? Go where they hang out. Talk to them, listen to them, like human beings don’t go there and pitch them stuff [laughs].

Reuven: Your suggestions are good and better than nothing, and I don’t have anything better to suggest. But it feels like there’s nothing that replaces good old just like bumping into people having lunch with them at a conference. Oh, you’re from where? That I just don’t see, even with all these online virtual conference, software systems that have been unveiled in the last six, eight months, they aren’t really that impressive. Unless they want to sponsor our show, in which case, they’re great.


Meg: No, I agree. It’s not, having been in that it’s like… I have also started up relationships with people that became clients in that sort of virtual community. Yeah, it’s not a replacement for but it definitely, but it’s exactly. Erik, I think you put that beautifully, like, go hang out, listen, be available to answer questions, and if somebody’s looking for what you’re, but often people will mention what they’re looking for. Somebody else might say, oh, by the way, Erik, he does this and tag you.  

That’s probably more likely to happen if you are part of that community and helping via I’m going to be looking forward to the one day when we can have conferences again and connect with people face to face again, that’ll be nice.

Reuven: So given all these options, so someone who’s relatively new, where is the biggest bang for their buck? Where should they given all these options for content marketing, what one or maybe even two things should they concentrate on to try to get the ball rolling?

Erik: Personally, the referrals, so like, the lowest hanging fruit is if you’ve had past success, whether it’s with like employers, co-workers, former clients, etc. Asking for referrals, and this, by the way, is not my area of expertise. So, but asking for referrals and getting those warm referrals is a great thing to do, would get my vote. The thing with content marketing is to get started there, you have to pick an area of content focus, which I would encourage anyone to do. 

But content marketing, if you’re a generalist, and you’re not sure how you’re going to play, it can be a little like boiling the ocean-ish. So my suggestion would be to rely on that referral, ask them for testimonials, that type of stuff, while formulating a plan, like who are you going to sell what to with content marketing? That’s my take anyway. 

Marg: Yeah, I would agree that those two going hand in hand for sure was probably the best route. For sure referrals, and I’m sure the next question for some freelancers, it’s like, well, if I don’t have project, who’s going to refer me to other people? The answer to that, which a lot of people would say, is, well, like hit up friends and family. I know that’s one of the biggest things that people say, I don’t know if my opinion is popular or unpopular about this, but I would say, avoid working with close friends at fan and family at all costs. 

Really, I know, that is a lot of times the first step that people tell you to do. But I would make… It’s harder to go outside of your inner circle. But I would make a concerted effort to do that, because things can get quite messy, especially with close friends and family. I would say as the first few steps is see the people who can be a really complementary skill set. 

So if you are a developer, seek out designers, seek out amazing designers that you can work with. If you are, again, I’m just talking from my experience as a developer as well. But if you’re a developer, there’s always entrepreneurs who are moving on to the next iteration of their business, which is a lot of the times creating online courses, productized services, things like that. 

Seek out those people who are really evolving because they need people to pass their clients off to that they like and trust and know. So those two things have been my biggest winners. I would say go the route of those two before going to friends and family, that’s my unpopular opinion. But I’ve definitely seen things go with teaching a lot of freelance developers, I’ve seen the biggest conflicts and the biggest mismatch of value come in when you’re working with friends and family.

Reuven: Yeah, I can’t imagine asking friends or family to help me draw a business. It feels very weird. I agree with you. I know a lot of people talk about it. I know a lot of people suggest it, and I can’t imagine it.

Meg: Yeah, I don’t know if I have anything. Those are the good places to start. Maybe past colleagues would be a good spot too, If you’ve been in your profession at all, for any amount of time, you probably don’t have no contacts. I said that, right, I forgot about that. It might have done a double negative there. But if you’re just starting out, there’s probably some reputation you can pull from to get some referrals for those first few projects.  

Definitely, I’ve also had experience with referrals with people who are in a different field, who are serving similar customers. Connect with those people, ask them how you can refer, who you can refer to them? Or some other reciprocal thing you could do for them like, so it’s not just asking, can you do this thing for me? Yeah, I agree on the on the content marketing, you need something to hook it on to. I think we come back to niching down a lot. But it’s not something you have to do right away. 

I didn’t go right, from generalist communications to case studies and testimonials, experts. It’s something I slowly flipped a switch over three years on, but I all my content marketing, if you could, podcast appearances, chatting with people, I focused it on that new service offering so that I could slowly move over to that.

Reuven: Right, I definitely think that the more you have a clear niche, the easier it is for people to understand, like, are you an appropriate fit for them? Do they want to talk to you? People become more self-selecting in terms of leads.  

It becomes just clear to say your message of what you do. When people would ask me what I did, I would give these long, long answers, because I’ve had to describe all the different things that I was doing. Now I just say, I teach Python.” Oh, Z, right. Now it’s okay, that’s interesting, let’s talk or that’s, or that’s not interesting, let’s talk, but like, that’s interesting, and not for us. 

We can make a quick, go no go sort of decision, and it’s mutual as well. Also, it means that now, okay, I know what I want to write my blog post about, I know what I want to do my YouTube videos about, I know what I want to develop in terms of additional knowledge. It’s good for me, and it’s good for my potential clients as well.

Erik: What I think of when I describe marketing, especially working in the content marketing business, Hit Subscribe, we sell things to developer tools, companies like Fullestop. So if you want content for developer tools company, that’s what we do. Otherwise, not so much. It makes the sales conversation focused like good marketing is really about establishing a position.  

I think of it as, helping your customers or prospective customers understand when you would be a good fit. But critically, also helping bad prospective customers understand that they wouldn’t be a good fit. The reason I’m saying all that is to work back to the genesis of this, the sales conversation is when you have stuff out there when you have a presence out there and a way of articulating what you do very specifically. 

It makes everything so much easier when the sales conversation happens because you can disqualify all kinds of bad fits right up front and allow good fits to qualify. So really, when you get on the sales call, there isn’t a lot of dancing. They know what you do. They have a pretty good idea maybe even about your prices, can you help them?

Then so it’s just kind of you almost have this conceptual agreement going in. You’re just talking particulars and like, for anybody out there listening that really doesn’t like sales, getting prospects to come to you, good marketing, good lead generation really takes a lot of the most horrible aspects out of the sales process.

Reuven: So, Meg, you got any picks for us this week?

Meg: Yeah, I’m going to recommend Keith Perhac’s new book, The 90-Minute Guide to Building Marketing Funnels That Convert, since we’re on the topic of content marketing. It’s really just no craft. Simple advice, if you have any marketing funnels or built an email, marketing funnels, run any of them, then I would say that this book’s got a bunch of practical advice on how to improve what works, and what doesn’t, and why. 

The 90-minute guide is a perfect name it that’s exactly how long it takes to read it. I have underlined the crap out of it for when I built a marketing funnel, so I can refer back to it. Yeah, so that it’s available in ebook and paperback.

Reuven: Excellent, amazing. Marg, got anything for us?

Marg: I honestly have no idea.


Reuven: Quick, look around the room.


Marg: I too tried to do, Oh my God,

Erik: I think you’re allowed to not have a pick for the week, right?

Reuven: Yeah.

Meg: I have skipped before.

Marg: Okay, I’m going to skip, I’m going to use my past to skip.

Reuven: You’d like to call a friend? Erik, you got anything for us this week? 

Erik: Sure, I will double up on self-promotion. First of all that the blog post series that I wrote, which is called the Business of Freelancing, so that’ll be easy to remember. I will include a link to that, just because that was part of what inspired the discussion here. So it isn’t just that post about sales. I’ve been doing these like lengthy series of posts aimed at freelancers kind of a broad range of topics, but like reasoning about business profit. Sales is part of it. Just a lot of different things that I wish I had known when I started out that I’ve learned as a business owner.  

The other one is if you’re in the app dev space, and you’re interested in writing for Hit Subscribe, we are going to be opening up the author roles, again. It’s relevant here, especially if you’re freelancing as a software engineer, and thinking about content marketing, number one, you’ll learn about content marketing. But number two, we’re getting author bylines about topics that you choose. 

So if you want to write about something out there in a particular tech stack, or you want something like that, you do get bylines on sometimes prominent, even developer tools, companies. So that’s a nice way to get your name out there. We do, of course, pay you. So I’ll give you the author link, and if you’re interested in that, mention in the form, you fill out that you heard about it through the show. That’s all I’ve got.

Reuven: Okay. This week, I will recommend a book that I just finished, called Flu: The Story of the Great Influenza Pandemic of 1918. Because what better way to spend your leisure time than reading about a pandemic that killed people. It’s a fascinating book, they’re actually two books on the subject. So now I’m about to start the second one. 

This book, is by Gina Kolata, who is a biology reporter science reporter for The New York Times for many, many years. Especially in very little time describing the flu itself and a ton of time describing how scientists over the 70 years following figured out and sequenced the gene and what they did all the crazy stuff they went through. A non-book version of this, it turns out was on a podcast I listened to called Science Verses where they basically told the story in radio form. Then they said, I’m thinking this sounds really like the book I read. At the end, they said, by the way, a lot of this was taken from the following book. 

So just mentioned amusingly, that on the Amazon page for the flu book, they say people who bought this also bought a book called The end of Epidemics published two years ago. Well, that was a poorly chosen title.


Reuven: Anyway.

Marg: Not the right, back to Meg.


Reuven: Great, great book, great podcast, definitely worth taking a look. Well, that brings us to the end of this episode, be sure to subscribe to our podcast in your podcast app of choice. If you like the show, please leave us a review. 

Thanks for joining us, and we’ll be back next week with the Business of Freelancing podcast.