Inbound Now #5 - Podcasting for Business with Christopher S. Penn

Christopher S. Penn, joins us for episode # 5 of inbound now!

In this episode we talk about:

  • Podcasting for Business - the dos and don’ts, how to get started with it.
  • Email Marketing Best Practices
  • A great twitter search tip that will help you find prospective customers that are looking for your business!


David: Hey, everybody. Welcome to Inbound Now, Episode 5. I’m joined here with a very special guest today, Mr. Christopher S. Penn. Chris is the Vice President of Strategy and Innovation over at Blue Sky Factory. He’s an avid blogger and podcaster, appearing on a number of different shows including “Media Hacks” by Mitch Joel and his own show, “Marketing Over Coffee.” So welcome, Chris.

Chris: Thank you.

David: Thanks for coming on the show. I wanted to get you on here to talk today a little bit about podcasting for business, and then we’ll dive into some email marketing, best practices because you work at Blue Sky Factory, an email provider. And then, you shared an invaluable Twitter tip on your blog a couple of months back, and I wanted to talk about that as well towards the end of the show. So, yeah, let’s get into it.

Chris: Okay.

David: Let’s start with podcasting. You took two things that I love in life – marketing and coffee – and combined them into one thing which I thought was awesome. Tell the audience a little bit about “Marketing Over Coffee” and why you started the show.

Chris: Okay. It’s a show started with John Wall. Actually, John was the original instigator of the idea. He had a show way back in 2005 called the “M Show.” It was ten minutes news talk and entertainment. He decided at a certain point that he kind of felt a little lonely just doing it himself, so he said, “You’re doing this financial aid podcast thing for the Student Loan Network. What do you think about doing a marketing show?” I said, “That would be great because there’s a ton of stuff I would love to talk about, but it’s just the completely wrong audience for the financial aid podcast.”

In 2007, we rolled out “Marketing Over Coffee,” and it has had probably some of the smartest, best looking listeners in the podcasting world. It’s a great audience. Probably about 10,000 people listen, which is nice. When we look in our database, it’s really interesting. We see a lot of Fortune 50 C-level folks who are tuned in and subscribe to it or the newsletter. It’s pretty amazing.

David: Right. And you use that demographic. You actually sell advertising for the show.

Chris: Yes.

David: So you monetized it.

Chris: Yes, we do.

David: Okay. Cool.

Chris: We have been very, very fortunate and very lucky to have advertisers. We have two advertising slots per quarter. It’s $5,000 per slot, and we’ve had those slots filled consistently since the show started.

David: Okay. Cool. The show’s great. I’ve been listening to it for like well around three years now. It actually inspired me to get into the podcasting game.

Chris: Great.

David: I tried it out there. Now, I’m doing this video podcast, and I’d like to thank you for that, for the inspiration to get out there and do it. So when you’re making the content for the show, when you’re coming up with the show with John, what’s kind of the process around grabbing the content and kind of getting it all together and ready for the show?

Chris: John and I typically via email kind of look at what’s happened in the last week or so in marketing and/or the stuff that’s on our minds. And then, we just show up at Dunkin’ Donuts. It’s a real donut shop. It’s right on the Natick-Framingham line, and there’s a Firestone dealership on 9 East. We’ve been going there. We were at 5:30 in the morning on Wednesdays, but then I changed jobs about a year ago and my commute got much shorter. So, now we have the luxury of 7:00 a.m. for recording which is lovely.

We just bang out the show there. Then, it’s cleaned up in post-production a little bit and stuff. We keep all the ambiance because there’s nothing quite like hearing the staff swear at the customers in Brazilian Portuguese. Unless you speak Portuguese, you don’t know what’s going on. And then it’s published every Thursday.

David: Okay, cool. Do you think publishing every week is pretty important, keeping consistent with that content?

Chris: It’s not the weekly schedule that matters. It’s the consistent expectation of time. One of the things I ask people and this is kind of funny. When I do presentations in conferences, I say, “How many people remember when Seinfeld was on?” And consistently, about a third of the audience always goes, Thursdays at 9:00 and stuff. I’m like, “Why do you people know this 14 years later? The show hasn’t been on since 1997.” It was content we wanted, and we knew when we wanted it. And so, for a lot of media producers who kind of do things haphazardly and publish whenever they have something to publish, that’s fine. But if you want to have that kind of predictable reaction, you do need to have a schedule of some kind. It doesn’t have to be weekly, but it has to be predictable.

David: Right, right because your audience expects that.

Chris: That’s right.

David: So, you’ve had a lot of success with “Marketing Over Coffee.” You also mentioned before the financial aid podcast where you worked at the Student Loan Network, where you managed to raise over $10 million in student loans via the podcast. Can you tell the audience a little bit about how you did that?

Chris: Well, a couple of things. The financial aid podcast came around because we were a small company. We needed some kind of strategic advantage over these gigantic mega banks that, frankly, their cream cheese budgets were larger than our annual profits and stuff. There’s no way we were ever going to out market or out spend Sallie Mae, as an example. So, we created the show.

Now, the nice thing about financial services, at least, during the heyday of the student loan period, 2004 to 2007 really, was that all these banks were just buying loans like crazy from every marketing company they could get a hold of. Clearing $10 million in loan volume is not a huge deal when at the time these banks were paying a grand, two grand, three grand per loan as a referral fee. At the time we were clearing a couple billion dollars in loan volume as a company, so $10 million by itself sounds cool. But then you look at the big picture and go, okay, a couple billion dollars of loan volume, that’s not a huge amount.

David: So, to put it in context, it’s kind of like the Dell Twitter campaign where they raised over $8 million. It’s like, wow, but if you think about how many billions they make a year, it’s a drop in the bucket. But it’s still pretty impressive. You used the new medium to raise money. You proved its worth, basically.

Chris: Right. It was worth the time invested, and the return on investment was great. You had, basically, $50 a month hosting service. You had a couple hundred dollars in the gadgets and stuff like that and then your time to put it together, but the time was going to be spent anyway because one of the most important things you can do as a company is basically command your employees to learn the industry, to learn what’s going on. And there was no better way for me to do that than doing this podcast where on a daily basis I had to figure out, “Okay, what’s changing in the student loan world? What’s different? What’s new? What legislative things are going on?” By the time I had done the show for a couple of years, I was at financial aid conferences surrounded by my peers of 20 and 30 years in the industry speaking to them about financial aid stuff. It’s because you bring this fire hose into your head and some level of expertise is almost guaranteed unless you’re really deeply stupid.

David: Right. Other than the monetary gain from doing the actual podcast, your company gained that thought leadership, and also your employees learned a lot more about the industry because they have to, basically, aggregate all of that content and share it out. I think that’s interesting that it’s not just a monetary ROI. It’s the return on thought leadership, if you will.

Chris: I still maintain that thought leadership is basically you’re thinking about leading, and one day you’ll do it.

David: Okay.

Chris: There is a baseline ROI. There’s a hard dollar amount that says at the very least we will earn this much, and that’s kind of where new media, I think, is right now. We are at a point where we can say, there is a baseline ROI on this, and everything that happens on top of that is gravy, all the thought leadership and stuff like that, the media.

We got into CNN and U.S. News & World Report, and the Wall Street Journal, just by having a podcast, because in 2005, no one was sure what it was. So they would, basically, talk to anyone who had a microphone.

David: Okay. Cool. For people out there watching and companies listening in, what advice would you give them, starting out with the podcast? What steps do they need to take, and what advice do you have from your experience?

Chris: When it comes to giving advice about podcasting, the first thing you have to figure out is does your content lend itself to an audio or video format? I’ll give you an example. Even though it’s very popular, one of the things that drives me absolutely batty is having an audio podcast about photography. I’m like, “I want to see what you’re taking a picture of.” It’s like, “Here’s a picture of the Louvre that I did with HDR.” I can’t see it. Show it to me.

Think about the content. Content is very flexible. I did a podcast that had several tens of thousands of listeners on financial aid. If there’s any more dry a topic, I can’t think of it, maybe mortuary science. If you can do it on financial aid, you can do it on anything. The question is, do you have the time and the content and the ability to be flexible with your content to fit it into the podcast medium?

Sometimes, it’s not the right choice. You probably do not want to have a video podcast on tax law, probably. If someone’s doing it and doing it well, obviously, leave a message in the comments of the show.

David: Right.

Chris: And think about whether your audience is ready to consume it. One of the biggest problems we had back in the day when the financial aid podcast started was that up until Apple released iTunes with podcasting support, there really was no customer base because people didn’t have the ability to do it.

Now, of course, they have iPads and iPhones and Androids and all the stuff. Everyone has the ability to listen to a podcast or watch a podcast. The irony is all those people who were doing the whole quit your day job thing with podcasting back in the early years, all the infrastructure is gone now. But the audience has all the devices now. We’re almost at podcasting 2.0. Let’s reboot it and get back into it.

David: Right. So, I think it is important if your industry is kind of boring, I think there’s a way to work around it. But, like you said, doing an audio podcast on photography doesn’t make a lot of sense.

Chris: Right, or cooking shows that are audio.

David: Right.

Chris: Why?

David: You can hear it sizzling, but you can’t see what it is.

Chris: Exactly.

David: Yeah, that’s awesome stuff. I wanted to switch gears a little bit and talk about email marketing.

Chris: Okay.

David: I’m going to play devil’s advocate here and basically say this and gauge your response.

Chris: Okay.

David: Email marketing is dead.

Chris: Absolutely. It is totally dead, and here’s why. It was never alive in the first place. What’s the function of marketing?

David: The function of marketing is reaching your customer base or prospective customer base and pulling them in and getting them to buy your product.

Chris: Okay. In the world of email, that’s called spamming because they’re not your customers. You don’t have an existing business relationship. So, if you just start emailing millions of people, you will be called a spammer, rightfully so. You have no permission to email these people. If the primary function of marketing is drive leads and to bring people to the table, email can’t do that. There is no such thing as email marketing.

Email itself is a really good sales tool. It’s two things. It’s a way to keep people coming back. If they’re a little bit engaged, you can deepen that engagement and get them coming back. Come to our webinar. Read our newsletter. Enjoy our content. Buy something. It’s also what I call an alternative sale.

There will be a certain percentage of your audience that they’re not good customers. They’re not going to be good customers. They have no budget. They have no authority. They have no need. They have no time frame. They’re unqualified to be customers. They are not unqualified to be fans or evangelists or advocates or people like that. For those people, email is the alternate sale.

So, you say, “Okay, if you can’t buy our product, at least subscribe to our newsletter and share it with your network, share it with your friends. Tell people about us.” It functions very well in that capacity for people who are not sure they want to commit or for people who can’t commit. It’s the alternate sale.

David: Right, right.

Chris: Email is a phenomenal sales tool.

David: I think that’s interesting that it’s not a marketing tool because you can’t just send out those mass messages because it’s not like check this out.

Chris: It’s illegal.

David: Exactly. It still happens occasionally, but it is illegal. I think to your point of it’s the after, after they know who you are, after they subscribe, after you pull them in via whatever inbound marketing you’re using, then it’s a good sales tool follow-up.

Chris: Yes.

David: I think that’s an awesome point you make there. What’s one of the biggest mistakes you see people getting into email marketing? I’m going to use that phrase because it’s …

Chris: We don’t have anything better yet, right?

David: Right. Yeah. Maybe, we’ll coin one later, but that would be interesting. So, what’s one of the biggest mistakes you see people making with their email marketing?

Chris: It’s really simple. We have a mantra that is practically a knee jerk reflex around the office. Send relevant, timely, targeted, valuable information for people who ask for it. If you screw up on any one of those things, you’re doing it wrong. If you send stuff that’s not relevant, it’s not timely, it’s not targeted, it’s not valuable, valuable most of all, to people who did not ask for it, you’re doing it wrong.

You need to send stuff that if you’re an inbound marketing company, like HubSpot, you probably should not be sending lemonade product emails to people. If you are an inbound marketing shop and you want to work with prospects, you probably shouldn’t send them emails seven months after they subscribe to your newsletter. If I subscribe, I want to get something when I subscribe.

You want some targeted stuff. If you can segment out people who come in via social media, you want to send them news and information that’s focused on social. You don’t want to send stuff on direct mail. They probably don’t want that. And the biggest one, the one that everyone gets wrong at a certain point because we treat email like a commodity, is valuable. Your content has to be valuable. It has to, in some way, provide entertainment, education, some kind of actual, tangible value in order for people to want to keep reading it.

Two of my favorite examples, Peter Shankman runs a service called Help A Reporter.

David: Right. He’s going to be on the show on an upcoming episode.

Chris: He has content that is so valuable. It’s free opportunities for media. It’s so valuable he gets angry emails and tweets and messages when his newsletter is an hour late. That’s the kind of value you want, something where people will be angry at you when your stuff isn’t there. If you miss a day or you miss a couple days on your newsletter and no one cares, it’s not valuable enough yet.

David: Right. I think another person who has a pretty valuable newsletter would be Chris Brogan.

Chris: Yep.

David: He spends a lot of time crafting that content that’s specific to the newsletter and not just an aggregation of all his blog posts and stuff.

Chris: Right.

David: I think that’s important to kind of gauge. Give them different content. Give them a reason to subscribe to your newsletter, other than subscribe to your blog and your Twitter feed. Make it different.

Chris: Yes, with the caveat that, especially when it comes to podcasting and new media, you want to have the email option.

When I was doing the financial aid podcast, I increased my audience by 25 percent overnight, literally, one day to the next, by having a subscribe by email option to it so people could get the link to the MP3. You would think, why in the world would you ever do that? That’s not what it’s for.

David: Right.

Chris: But there’s a certain percentage of the audience said, we know email. We understand email. We get it. In my case, it was financial aid officers, the folks who were outside the demographic of the college student. But they are very influential in the process. Put in that email box, boom, they’re on the list. They’re like, “Oh, this is great. Can I share this with my students?” Of course, you can share my marketing message with your students, but that’s the power of email. If you’re careful with it and you provide value, people will love you for it.

David: Right. And I think email is kind of, like you said, entrenched. Everyone’s used to it. It’s been around for so long that people are so used to getting content that way. I think providing that, if they don’t have an iPod or they don’t know how to use iTunes or what have you, make it easy for people to subscribe. And I think that’s kind of the takeaway there.

Chris: Yep. That and with email, too. The thing that’s funny about email is that it is truly a public utility. It’s got a set of protocols. No one owns email, right? So you build your database. Jeff Pulver is famous for saying, “You live or die on your database.” You build your database. You have it. You own it for as long as you’re in business.

There is absolutely no guarantee that today’s Facebook won’t be tomorrow’s MySpace, that Twitter, as we all know it, will suddenly just stop working. These things, they look like public utilities. They are not. You do not own them. You can be kicked off of them. You can have your fan page canned. You own your email. You own that asset, and that is the best digital asset you can have.

David: Definitely. I think I brought that up on past episodes. I think I heard it from you on “Marketing Over Coffee.” So there you go. What are your thoughts on people doing lead nurturing or drip email campaigns that kind of keep people engaged while they’re not ready to buy but, maybe, in the future they will be?

Chris: It’s probably one of the biggest no-brainer things you can do. Provide valuable content to people. Whether or not they’re going to buy anything, provide valuable content anyway because, again, it’s the alternate sale. If they’re not going to buy, that’s fine. If they share it with 20 people who will buy, there you go. You’ve paid for it, more than the investment in it.

Unless you actually are selling toasters in retail, there is not a lot to be gained from a constant stream of buy, buy, buy messages. There is a lot to be gained from education and entertainment in all the marketing channels, not just email but Twitter and Facebook and all these things.

If you can provide people with stuff that they consistently find valuable, they will buy from you because at a certain point you gain presence of mind. You gain mind share, and if the need arises for them, you don’t have to do demand generation then. As soon as they think, I need inbound marketing help. Who should I call? I’ll just call HubSpot. I get their newsletter. I just need an email marketing service. I’ll just call Blue Sky Factory. There is no one else in their brain.

The idea of a lead nurturing campaign or a drip campaign is very short-sighted. Create good stuff all the time, and people will naturally just come back to you because, “Hey, where do I get my good stuff from? Oh, I’ll just go to David. He knows his stuff.”

David: Right. It’s staying top of mind and providing that valuable content. They’re like, “Oh, yeah, I do need an email solution. I’m going to call Blue Sky Factory because they help me out with so much stuff. They help me decide how the best practice is and what have you.” I think that’s super important and really something that we really want to stress here is you want to keep top of mind so when they are ready, they’re going to thank you for it and come back.

Chris: Right. Ideally, you want to be synchronous in people’s mind with the term that is your expertise. If you say inbound marketing to someone, you want them to have the reflex reaction, oh, yeah, HubSpot.

David: Right.

Chris: You say email marketing. Oh, yeah, Blue Sky Factory. When you say Twitter, who do you think of? You say Facebook. Who do you think of? These are all things that if you create that value, it’s baked into people’s brains.

David: Absolutely. There’s a lot of industry buzz now about tying email marketing to social media. How are you seeing companies do this, and what are some tips that you can give people who are trying to tie the two together?

Chris: At the most basic levels and this is something you’d be surprised how many companies don’t do it is tell people that you have a social media presence. That’s an obvious thing, but people don’t do it anyway. Tell them that you have a Facebook account and what you’ll get by going over there. You have a Twitter account and what you get by following someone on Twitter.

And then, there’s functionality in most providers. We have it. Share with your network. Share this content with your social network. If it’s valuable, people will do it anyway, but make it easier for people to do it. For example, in our tool, Publicaster, we have a little set of share buttons. And then, what I do that works really well for me, and I’ve done this in “Marketing Over Coffee” and I’ve done this with my personal newsletter, is I will give you incentives for sharing.

We had five free tickets to the Inbound Marketing Summit for the people who shared the “marketing Over Coffee” newsletter the most. You can measure this inside of our tool. We had a 282 percent growth in audience by having a share with your network thing that had an incentive tied to.

People saw it and said, “Yeah, I want a $700 ticket. What do I have to do? Oh, click Twitter. Share, Twitter click. Share on Facebook? Okay, I’ll do that.” I do this thing on my own personal newsletter that is totally free. It seems like the silliest thing in the world. Every newsletter I measure who shared, got the most new eyeballs and the most new clicks via social media, by sharing it with their networks. I feature them in the little section of things that you did, and people can have their Twitter icon and their name in lights and the link to their website. I tell my audience about some of the more prominent members, but they get prominent by sharing it with their networks. So, the incentive is share this and you’ll get your time in the spotlight.

David: In the inbound marketing example, I actually won one of those tickets.

Chris: Yes, you did.

David: And thank you for that.

Chris: You’re welcome.

David: Incentivize people to share your stuff, and people will. I think that’s an awesome tip and incentivizing your list to share it and to follow you, just saying hey we’re on Twitter. Follow us on Twitter for the latest news on Industry XYZ or whatever is really a powerful thing because people are opening your emails. And if they don’t know you’re on Twitter or they don’t really want to search for you to find you, it’s just an easy way to do it.

Chris: Yeah. And, you know, also do a little bit of research. One of the easiest things you can do is take a thousand of your email addresses, create a brand new Gmail account, fresh and new, load those thousand in as contacts, and then go network by network. Sign up on Twitter. Sign up on Facebook. Sign up on LinkedIn.

The first thing all of the services do is say connect us with your Gmail account, and they will tell you how many of the people out of that thousand are on Twitter or Facebook or LinkedIn or whatever. If it’s zero, then obviously you don’t need to spend a whole lot of time there. But if it’s out of that thousand, 970 are on Facebook, you probably should have a really big share this on Facebook button in your newsletter because that’s where your audience is.

David: Definitely. And you can do that just by searching with someone’s email address that signs up on your list, like, to plug it into the Facebook search box to see if they’re there.

Chris: Exactly.

David: I think that’s a great tip as well. All right. So, on your blog,, Awakening Your Superhero, you wrote a couple months back on three nearly guaranteed moneymaking words to use on Twitter. And those would be recommend, suggest, and anyone. Can you explain?

Chris: One of the things that is like Social Media 101 is listen, and people are like, “What do I listen for?” Well, start with your keyword list. But one of the simplest, most powerful terms people use is, hey, can anyone recommend a service that does X? Can anyone recommend an inbound marketing service? Can anyone recommend an email marketing service?

These are questions you should be listening for. These are easy softballs that you can bat out of the ballpark. If someone says, hey, can anyone recommend an email marketing service, we have our Director of Community, DJ Waldow, is usually within ten minutes will say, “Hey, here we are. How can we help you?” What are trying to do and stuff?

These people are asking these questions every single day on every single social network. You have the list. Or on Quora, which is the newest shiny object. People are still saying, “Can anyone recommend?”

David: Right.

Chris: It doesn’t have to be just on Twitter. It’s on any social network. People are saying, can anyone help me understand X? And if you are that resource, you automatically identified someone who is interested and has displayed very publicly their intent to, if not buy, at least learn more, and that’s the fastest way to gain mind share with folks is to be there. Both Chris Brogan and Greg Cangialosi, our CEO, live by the mantra, “Be there before the sale. Be there if people just need help. Be there as part of their network, as part of their community.”

So, again, when they go, now I’ve learned a bit about email marketing or inbound marketing, now I’m ready to buy, there is no question who they buy from.

David: Exactly. So, just searching the social media and, basically, is an invaluable market research tool and using these advanced search strings, recommend “email marketing ? – HTTP.”. I’ll put this in the show notes because it’s kind of [makes noise]. But basically, that’ll filter out who’s actually looking for suggestions or recommendations on product, whatever your key word is.

It’s, like you said, a great way to just, hey, raise your hand and say we’re here. Do you have any questions? Do you need any help with … not jumping in and saying, “Hey, we’ll sell you it right now.” But helping them out and nurturing them down to that purchasing state.

Chris: Exactly.

David: I thought that post was awesome, and I actually set up my entire HootSuite with a bunch of different search strings for different things that I’m looking for.

Chris: You want to take that up a notch. Subscribe to the searches in Google Reader.

David: Okay.

Chris: And then, you’ll get in Google Reader, there’s a little show detail links. Click that and you can see how many people asked that question over a 30-day period? What day of the week did they ask? What time of the day did they ask it on? And that will give you the insight as to … if you're sending a newsletter about inbound marketing, why not send it on the day and time when most people are talking about it?

David: That’s good. That’s a good tip. I’ll have to do that. I haven’t touched my Google Reader in a while, actually. I use an iPad app but, you know, it’s all good. Cool.

Chris, where can people find you online?

Chris: You can find me at I blog every Monday on email. This year, actually, the theme has been email as sales. And then, you can find my personal blog at, and the podcast is at

David: Right. I definitely recommend checking out “Marketing Over Coffee.” They have some great stuff coming out every week. So go check them out.

Chris: Every Thursday morning.

David: Awesome. Well, thanks for coming on the show.

Chris: Thank you.

Read more: Podcasting for Business & Email Marketing Best Practices w/ Christopher S. Penn [@InboundNow #5]