Christopher S. Penn, Co-Founder and Chief Data Scientist of Trust Insights [Podcast]

We’re starting a new video series of interviews with some of the smartest marketers we can get our hands-on. We’re excited to kick things off with every marketer’s favorite marketer, Chris Penn.

In this interview, Chris talks about…

  1. The evolution of marketing in the last 10 years
  2. The power of “They Ask, You Answer”
  3. AI for marketers
  4. How to make sense of big data
  5. Advice for marketers in this COVID-19 pandemic

We hope you find this as informative and useful as we did!

Digital Transcription (edited for readability)

Jon-Mikel Bailey: All right, everybody. Thank you for joining us. This is the Wellspring Digital chat and today our first guest is Christopher Penn, who is a marketer extraordinaire. I’m a huge fan of his. If you do not get his newsletter, you need to subscribe to it right now.

Go to or just google Christopher S Penn, you’ll find it. I’m going to do a very small amount of talking so you can get all the goodness from Chris. So first I want to get Chris to introduce himself. So Chris, welcome. And if you can just give us your bio. Give us a little bit about you.

Christopher S. Penn: Sure. I am the chief data scientist and co-founder of We are an analytics consulting firm. I’ve been doing marketing for more than two decades, I have been doing analytics for almost two decades and spent a lot of time now in data science, machine learning AI, all the fancy stuff with numbers and things. And yeah, that’s about it.

Bailey: Cool. Well, thank you so much for taking the time to do this. I know these are crazy times, and we’ll talk about that in a little bit. But I want to do a quick take a trip down memory lane.

So I’ve known you since the Blue Sky Factory days. Greg Cangialosi, Blue Sky Factory in Baltimore. I think I met you at a Frederick County Chamber of Commerce something or other. It seems like 1000 years ago, and I wanted to just, you know, briefly get a sense from you of what you’ve seen in the evolution of marketing since your days at Blue Sky Factory, which was how many years ago? That was now exactly a decade ago. It was a decade.

Penn: Yeah. So obviously, time flies. No, the biggest thing that has changed by far in the last decade is the fact that these little devices (holds up phone), these smartphones, iPhone came out in 2007, iPad came out in 2009. And the world has not been the same since. We live on these devices, 24-7 and all digital marketing is, if you’re not already a mobile-first marketing company, you’ve missed that boat by about five years. Right?

Better late than never. And what’s been interesting to see is how much these portable small devices make the nondigital world also digital from, you know, people googling or searching Amazon for a product while they’re standing in someone else’s physical store, to search inquiries and people talking, you know, now with smart assistance, people who are just shouting to the air, “oh, hey, assistance, you know, the price of this thing.” I remember when Bluetooth headsets first came out, and you’re like, seeing somebody talking to the air like a crazy person or Bluetooth headset now it’s a headset.

Bailey: Everybody’s a crazy person.

Penn: Exactly. And so, you know, that’s really been the biggest macro change the last 10 years is just, you were walking around with a supercomputer and you’re now connected to the sum total of human knowledge in your pocket every single day. Even the lowest budget smartphone still has capabilities that, you know, 10 years ago would have been bewildering.

So when marketers are thinking about what’s happened to marketing, that’s where it’s been, and what’s likely to come next are variations on this because this is just about the right form factor. People have been toying with, you know, smart rings, smart jewelry, smartwatches, and stuff. And those are contextually useful, but they’re not a substitute for having a device that is large enough to be able to read what’s on-screen and be able to interact with the capabilities for your screen

List interfaces are doing good, but not at a point where they’re great. Screenless, voice interfaces definitely are something you should be paying attention to now, and building apps for now. But it’s not at a point yet where people feel comfortable. It’s we’re not in Star Trek yet where you can just yell out to the computer and understand exactly what you mean. You know, in context, we still have to be very specific.

Bailey: Right, right. Yeah, I’m curious to see what the next smart whatever is gonna be. Smart shoes, although I think those already exist. So one of my favorite books is “They Asked, You Answered” by Marcus Sheridan. You’ve really embraced this philosophy with your You Ask I Answer blog series, which I think is great.

I think it’s a fantastic way to stay on top of, you know, regular daily issues that people are having with a blog series, but you do a ton of them. You even did one for me. I wasn’t even expecting it. It was fantastic. Can you talk about the process of that and you know, how it’s been going and you know how well, you think it’s working for you?

Penn: Sure. So let’s talk about how well it’s working. It is the dominant form of content on my personal website. Right now it is also cross-posted to company properties.

I have seen it make up for the loss of social media traffic, thanks to YouTube and its distribution channel. The important thing about the process is not that it’s a blog series or it’s a video series, but it is taking content and repurposing it as quickly as possible.

So the way it works is, every day I take a question and I went with Marcus’s philosophy because it means I don’t have to create new ideas, right? Customers are creating the ideas for me I just have to provide what information I have available that will answer the question. The process is that…

  1. I record the video every day 10 minutes or less because LinkedIn has a hard limit of 10 minutes for uploaded videos, answer a question.
  2. I produce the video and I get the mp4 file I use a piece of software a piece of open-source software called FFmpeg to convert it to an mp3 file.
  3. Now, I have a video, I have a podcast episode.
  4. I take the mp3 file, I load that to a company called They’re a transcription company or AI-powered, a phenomenal company, love them.
  5. That gets me an SRT file, which is the closed captions and it gets me a text file.
  6. That text file then becomes the blog post transcript.
  7. So now I have a video. I have a video with subtitles, I have audio and I have text.
  8. All of that gets turned into a blog post.
  9. The videos get loaded to LinkedIn.
  10. the videos get loaded to YouTube and the SRT files go up to link to YouTube as well.

I can’t remember the exact status but an astonishing number of people watching the video if it has subtitles without the audio on. They can see this, business folks a lot in the restroom. They will watch a video without the audio on if it has subtitles, they’ll stick around and watch if it doesn’t have subtitles, they don’t want to turn the audio on to the restroom stall.

And so they’ll skip past to the next thing.

Bailey: That’s interesting.

Penn: Yeah, it’s people being people. And so the process there is you create all this stuff and you have, you know, all of its templated things so that there’s a minimum amount of time spent processing the thing.

And so from beginning to end, I start the video at approximately 7:10 am each day. And by 7:45, I’m wrapped up and everything is out. Distributed, got the social posts from it in a blog post, got the video on YouTube, three videos on LinkedIn got the sharing across networks.

So it’s a way to create a lot of content quickly, efficiently and it’s a one-person show. I know there are a lot of folks. My fellow high school classmate, Gary Vaynerchuk is funny, famous for saying like you need to create, you know, 100 pieces of content today. Well, that’s great, because he has literally a staff of 27 people doing that for him.

The process I use a one-man show, it’s just one person to do all of it, but it works really well. And so again, the traffic I get, I get great search traffic from it, because the transcripts 10 minutes of talking equates to 1500 words.

Yes, if you crank a 100-word blog post each day, you’re doing well. I get the podcast exposure because it is available as a podcast. And so I get those numbers. I get YouTube exposure links, and then I get, you know, LinkedIn traffic and stuff like that. So it’s a comprehensive way to do a lot of content quickly.

Bailey: One thing I wanted to ask real quick, you went to high school with Gary Vaynerchuk? What was he like in High School?

Penn: Yep. He was in high school. Very quiet withdrawn he was on his own. He was by his own admission, a terrible student. English is not his first language, Russian is. You know, he basically spent most of it when he talks it when you listen to him talk about his childhood growing up, you’re working his dad’s wine store is 100% true.

You know, he went to school did badly then I went home and work to this his dad’s wine store for the rest of his, you know, his time and did not do much, you know, socializing, if you will, right now. Not that I did either.

Bailey: Yeah, I’m kind of with you. Alright, so everybody’s talking about data and AI. I see some posts about it that are good. I see some posts about it that are bad. A lot of people glaze over at the mention of big data or AI. I think a lot of people really just misunderstand, generally what AI actually is.

Can you talk a bit about the impact of AI for marketers in terms of their day to day and how they might already be using it and not even realize that and other ways that they can be using it?

Penn: Sure. So let’s start with what it is. It is a blanket term that means we’re trying to create capabilities and computers to replicate human intelligence tasks. So if you can hear the sound of my voice, and it means something, you are doing what’s called language processing in your brain, right, which we can try and teach computers to do that. If you are watching this video, and it makes sense to you using what’s called vision.

There’s the analog of computer vision. But so, AI encompasses all the different ways to try and get computers to replicate human intelligence tasks. What is most applicable to marketers is what’s called machine learning, a subset of AI in which you give an enormous amount of data to a machine and you teach it to learn from that and then predict or classify based on what it is.

So, for example, if you fed all of your Twitter data to a machine learning algorithm, and then you said predict for me whether my next post will get more or fewer likes than previous posts, that would be an example of machine learning. Marketers are already using AI, whether they know it or not.

If you use Google Analytics, you have a little Google Analytics app on your phone. And you notice there’s a little, you know, notifications. And it says, “Hey, you got more traffic, you know, yesterday than did last seven days,” or “Hey, I noticed this page seems to be doing well.” Those are that’s anomaly detection, essentially. And Google Analytics is doing that on your behalf.

Then we can ask Google questions. Again, that’s language processing and insights. So marketers already have access to some of these capabilities.

Where there’s a tremendous amount of value from marketing going forward, is in more customized uses of this. So a simple example is we do something called digital customer journey modeling inside Google Analytics. There’s a tremendous amount of valuable data like, in what order? Did somebody use different channels Facebook, Twitter, email, etc, on the path to conversion?

And then you can take that apart with custom software that we built, and understand how important is any one channel to the conversion? The analogy I like to use is if you watch basketball unless you’re talking Golden State Warriors, in which case Steph Curry is pretty much the only person on the court.

The person who assists is just as valuable as the person who shoots at school. Sure, right. That’s modern attribution analysis, all these digital channels we have interacted with each other. You and I know this from our customer journey, our own customer journeys when we’re researching a product. We just don’t go and follow a linear order. We ask friends, we read reviews, we do all these things that eventually lead us to buy something.

So when marketers are doing customer journey mapping, if you use the data you already have, you can put together at least on the digital side a very comprehensive model of how people interact with us. Here’s what channels assist the most, right? And therefore, we should not cut their funding even if they’re not the last thing somebody did.

In what order do they do it so that we can tune our messaging. So, for example, if Facebook is the beginning of your customer journey, and all your Facebook messaging is buy now, it’s like, you go on that first date, it’s like “marry me.”

Bailey: Right, right. So with all of that data, you know, with all of the platforms and dashboards that are available to people, do you have any tips for marketers on how to stay focused, you know, when so much is coming at them at all times.

Penn: There’s are two ways to handle this. The data science and machine learning ways to take all the data you have essentially put in a really big table. And then you have an outcome you care about: leads, sales, revenue, whatever. And you run a mathematical technique called multiple regression subset analysis that mixes and matches every possible combination of all those fields.

And then it spits out “here are the ones have a mathematical relationship/correlation to the outcome you care about,” then you test that correlation with the scientific method. And you establish these four or five numbers are really the most important.

The nonmathematical way that people do that is called KPI mapping. We say okay, we have revenue. Okay, well, what things do we know drive revenue: number of sales deals one great, number sales deals won. What things drive that? Well, open deals, okay, well, what drives that and you keep chasing this chain of evidence and creating a sort of like almost like a tree, and then you figure out okay, what things do I have control over that have a connection to that outcome we care about?

That is a more practical but less accurate way of doing that kind of KPI analysis because at the end of the day, we have to ask ourselves as marketers, what number am I going to get a bonus for? What number am I going to get fired for? Right? That’s your KPIs. If you know that, you’re kind of hosed.

Bailey: Right, Yeah. Good point. You gotta follow the money.

Penn: Exactly.

Bailey: Yeah. Yeah. So last question. I wanted to ask you, and I’d be remiss if I didn’t mention our buddy Covid-19. I just wanted to see if you had any advice for marketers and small businesses out there on you know, how to just exist in a professional way and navigate these strange and very scary times.

Penn: There’s a lot of different answers and different aspects to this question. The first is that you need to stay informed through reliable authorities: Johns Hopkins University, the CDC, World Health Organization, the state, and local authorities in your area. If you’re outside the United States, you know, whatever your provincial government says. So, you know, you need to know what’s going on.

Secondly, be paying attention to economic indicators, economic indicators are going to be what’s going to impact your business the most because if you see, for example, a drop in consumer spending and you’re a B2C company, guess what? There are people are going to be spending less money with you.

If you’re a B2B company, you need to be looking at things like producer price indices, business confidence indices, to again, understand what is the appetite somebody has for making a purchase of products or services.

We know with almost perfect certainty that a recession started actually about two months ago, but it was just the first hints of it. This obviously is not a tipping point, it’s a giant shove. Yeah. And so according to Johns Hopkins Center for Health Security, in a situation like this, your planetary GDP is likely to be down to minus 11%. First Year minus 25%. The second year, that’s a huge number.

So for marketers and businesses, one of the things to be paying attention to is: how do you pivot your product offerings, so you’re pricing to reflect the new reality? People are going to be extremely risk-averse. They’re gonna be focused on ROI. They’re gonna be focused on generating revenue, focused on cutting costs.

How do you change your service offerings and things to reflect that? So, for example, with Trust Insights, we’ve made sure that we have many tiers of pricing and many different products that are available for where people are, and understand that your sales cycles are going to be lengthened dramatically because your people are risk-averse.

The disease itself, even in the worst-case scenario is any loss of life is sad. But it’s not a big problem. The big problem is the healthcare system impacts. Yeah, 20% hospitalization rate and the macroeconomic impacts which will arguably be the biggest problem because if you have a whole group of people who have no income anymore, have no jobs, things that significantly dampens things like consumer spending.

The consumer goes first, the business comes second, so B2C gets hit hardest first and then because B2C dries up B2B then runs into trouble. So by projections from the University of Basil, the first wave of the pandemic is likely to be over by August or September, but just because we’ll run out of people to infect, right now that you know, that’s where the biggest and it will peak in some time.

In June, then you’re going to have if you model it based after 2008/2009, you’re talking about a three-year recession. Three to five years depending on how bad it gets. Supply chains so far more or less holding up, but you know, that’s that going to depend heavily on what happens.

So, if you’re a small business owner, and we just did this ourselves, get yourself a business line of credit. Now, while credit markets are still available so that you have that backstop for financial services. This is the time to look at your own spending, remove anything nonessential, I mean, you’ll have to like cut to the bone and just, you know, stop doing everything.

But if there’s that software that’s subscription or that service, like yeah, you know, we’ve never actually used that thing. This would be the time to turn those dials off. It won’t save you a ton of money but every little bit will help.

As a marketer, this is the time to build your audience, your audience is going to be what you live or die on. This is the time to grow your mailing list, grow your text messaging list, make sure and make sure it’s an own audience, not something that Facebook owns, own that audience and grow it as fast as you can, by providing great value.

Be in a position where as long as it’s not materially harmful to your business, give as much as you can. Because in times of stress, people appreciate you not taking advantage of them.

Bailey: Right. Yeah, exactly.

Penn: And, ultimately, you want the, it’s going to take according to the Journal of, can’t remember, the European Journal of Social Psychology: new habits take about a median of 66 days to set in work when the habit becomes automatic. So as we do, how is it how all these major changes happening you know, right now it’s too soon.

Don’t try to, you know, change consumer behavior. Monitor. Keep an eye on it. And then as new habits start to form, you’ll know in a couple of months, you’ll be able to get a sense of here’s where we need to go in the marketplace, based on what people are doing, what they’re buying, what they’re selling, and so on and so forth.

So that’s at that point, you could start to make, you know, more longer-term strategic decisions because you’ll be well into the recession by then. The pandemic will have become business as usual. Right, and the new normal, which is the phrase everyone loves to use, and from there, you can begin really planning.

So right now cut your costs, keep your expenses contained as best as you can. If you have not already been doing so stockpile some cash, it’s a good thing to do, from a business perspective, get that line of credit, and then do a lot of these planning exercises. You know, what’s the worst-case scenario? What’s the best-case scenario, what’s likely, what are second, third or fourth-order consequences? If the spending goes down what happens next? What happens next? What happens next? And that way you could scenario plan.

Bailey: Okay. And speaking of building your list, do you want to take a moment and let people know where they can find you and sign up for that, that those both those amazing newsletters that I subscribed to that I love?

Penn: Sure you can go to for our company newsletter, we have fresh data every week. This week actually just went out, the business mentions of Covid-19 and the impact on Facebook engagement rates and my personal newsletter, you can find at

Bailey: Which is a great one of my favorite newsletters. Definitely. So well, I wanted to thank you again for doing this. And again, amazing stuff here that you’ve given us and so I really appreciate it. And that’s it. We’re done. All right.

If you or your company needs any assistance, please let us know and we’ll help in any way we can. You can contact us here or call us at 301.304.9349.

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