#149: The Story Behind Seeking Wisdom

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This is a podcast episode titled, #149: The Story Behind Seeking Wisdom. The summary for this episode is: In this episode of Seeking Wisdom, DG is taking you back in time...to 2015. He had just joined the marketing team at Drift. There was no content. There was no blog. And he had a busy CEO who was full of ideas – but who had no time to spend turning them into content. Tune into to learn how DG was able get more content from his CEO – and create the world’s first six star podcast in the process.

DG: This is DG. I'm in the studio secretly right now. And on this episode of Seeking Wisdom, I want to tell you, for the first time, I don't think we've ever shared this fully publicly. I want to tell you the story behind Seeking Wisdom. All right. So this is a secret little episode of Seeking Wisdom, because we had a little mix- up. DC is out. I'm out. We're both traveling. And so we missed each other to create an episode, a new episode. But this is actually perfect timing because sometimes this stuff just happens. You ever noticed, like you have an idea and then that idea kind of bubbles up three or four times, and that's how you know it's a good idea and you should do it? At least three times in the past week, I've told a story about how Seeking Wisdom came to be. I did it in two interviews and then another webinar that we're going to do. And I realized, you know what, we haven't actually talked about this on the podcast. And I think the reason why is because DC is humble, and he doesn't like when I talk about this idea that he had, and I don't know, whatever. So I thought that, because we didn't record an episode together this week, and because Gail, who runs everything behind the scenes on the content side of things for Seeking Wisdom, she hit me up and she's like," There's no episode. You got to do an episode." So I was like," I have an idea. I'll tell the story behind Seeking Wisdom." So I thought I'd spend 10, 15 minutes today with you, telling you the story behind Seeking Wisdom. So, funny story is, I been in Boston Tech. Drift is in Boston. Our headquarters is in Boston, and I had been in Boston Tech for a couple of years. And because I was working in sales and mar, I always kind of worked in sales and marketing technology companies. And so, because of that, I had gotten to know, through Twitter, early Twitter, like 2009, 10, whatever, this guy named David Cancel. And I thought he was so mysterious because he had all these Twitter followers. He had this great blog. He had this email list. He had all these really smart things to say, but I never saw him anywhere. I was like," Who is this guy?" And then he was at HubSpot. Long story short, they leave HubSpot. He leaves HubSpot. They go to Drift. They start Drift. Probably a year after they started Drift, I had a podcast on the side that was called Tech in Boston, where I went and I interviewed local entrepreneurs, founders, whatever. And I always wanted to get DC on my podcast, but I never reached out to him. I don't know why. I was probably intimidated. And then one summer, I remember it because I have this weird thing with dates, with memory. I can't remember math. I don't know math. I can't remember anything else, but dates I can remember. And it was July 2015, and DC and the Drift team. This was Drift with two Ts. They were having a party to open up the new office that they had in Canal Park and Cambridge. And I get a direct message on Twitter, in the Tech in Boston Twitter account. And it was from DC. And he said," Hey, we're having an office warming party. Can you share this out to help spread the word?" So, shoutout to DC, doing a little hand- to- hand marketing in their early days of Drift before me. Right? And, so I did it and I shared it. And then I said," Wait a second. This is my opportunity." So I said," Sure, I'll share it. By the way, while I have you, it'd be awesome to have you on my podcast sometime." And he said," Let's do it." So a couple of weeks later, I go to the office at Drift, and I did a podcast with DC, and I was blown away, because I was like," This guy is who I hoped he would be." And we just hit it off. And he had all these stories that just were not like anybody else was telling them about. Why he doesn't hire MBAs and how he doesn't believe in roadmaps. And all the non- traditional DC takes that you know now. At the time, he showed them on his blog, but I never heard a podcast with him. I never heard a ton of interviews with him. It was like he was hiding. So, I had him on the podcast. It was awesome. And then the next day, I was on the Drift website to look up some bio about him to get ready to post the episode. And I found out that Drift was hiring their first marketing person. And so I reached out to Keith, who's still here, still runs recruiting at Drift. And I said," I need that job. I want to come talk to them." So long story short, go in, get the job. But I remember that in the interview... Actually in the Tech in Boston interview, I wonder if we could splice that episode in somehow. We could go back and check it out. In the interview on Tech in Boston, after that, I talked to DC. He sends me an email about all this podcast gear. He's like," Hey, what gear do you use for your podcast? I've always wanted to start one." Which is funny. If you know anything about DC now, him asking me for gear advice is just, it's ridiculous to think about. So I told them I use a zoom, blah, blah, blah, these mikes. And I was like," What's your podcast going to be about?" He's like," I don't know yet, but I already have the name for it. And the name is going to be called Seeking Wisdom." I kid you not. This was the summer of 2015. I wasn't even at Drift yet. There wasn't even a podcast that he knew he was going to call the podcast Seeking Wisdom, because of this book, Seeking Wisdom From Darwin to Munger. I said," Man, that's such a good idea. Great name for a podcast." Long story short. How many times have I said," Long story short?" I go to Drift. A couple of weeks after I'm there, we start thinking about Seeking Wisdom. But didn't really know what the podcast was going to be. At the time, we had no content at Drift. There was no blog. There was no website traffic. There was nothing. And so my whole strategy was man DC. This guy has so many things to say. He has so many thoughts. He's sending me text messages, videos, whatever. This is all great content that I can use to help jumpstart our content, right? To start writing for our blog. So, I did what most marketing people do. They say," Hey, can you write one article a week for the blog?" And DC, as most CEOs do, they just never respond. Every marketer out there is nodding their head right now because they know how hard it is to get content from your CEO. And it's such a challenge because they have the thoughts. They have the visionary stuff, the thought leadership, the stuff that would make great content. But the challenge is it's so hard to nail them down to actually get it out of them. They're not going to write it. So I had this idea, which is," Wait a second. What if I just go in and I just interviewed DC for 30 minutes each week? Like I just mic him up. And I just have him talk about a topic." So I tried that. We went into the room. I grabbed the zoom mic and I left and I said," Hey, I want you to talk. Here's a topic." I printed out some notes and said," I want you to talk about this thing about why you don't ever hire product managers." And he comes back out 20 minutes later and he hands me their recording. And he's like," Here it is." I listened to it. DC, love you, but it was awful. It was like just DC in a room, just talking about stuff. It had no rhyme or reason, and he wasn't super enthusiastic about it. So I said," Okay, we're going to try this again." And the whole point was, I just wanted to ghost write for him to get content going. So I didn't really need anything groundbreaking on the audio side, I just needed his thoughts. So I could then write them and publish them as ghost written stuff from DC on our blog. Then we go in again and I said,"You know what, this time you don't need to prep. Don't do anything. Just show up in the room and I'm going to interview you." So this time, instead of giving him the notes, I had the notes that I wrote for myself. And I just treated him like an interview subject, right? Like I was on 60 Minutes and my goal was just to interview him. And so we're going to just cut out my voice on the audio and publish that as a podcast. But what happened was, that conversation actually morphed into a little bit of a back and forth. And it was when we had this back and forth that there started to be a little bit more banter. And it was about like," Oh, interesting. I've never thought of it that way." And that helped Seeking Wisdom morph into what it is today, which is conversation between two people about life, learning, marketing, sales, what's happening at Drift, reading, things we're learning, things we're doing. And what it turned into was, this weekly story between two people who are at different ends of their careers, right? DC's done founder and CEO of five companies, five- time founder, two- time CEO. Me, I'm just a guy that had a podcast and I've done marketing at Drift over the last couple of years. And I think that's what we hit gold on, which is, don't try to force this thing. Just have a conversation between two people and see where it goes. And so it went from taking this idea of ghost writing posts for DC into a conversation between the two of us, and the easiest way that we got this podcast going was just about talking about what was going on at Drift." Hey, how do you think about hiring?"" Oh, we just had our first company meeting. How did it go? What did you talk about?"" Oh, we just set goals for Q2 2016."" How do we set that? Like, what's the right way? When should we focus on this first?"" How are you thinking about content? How are you thinking about PR? How are you thinking about building a brand?" We just started having conversations about all that stuff, really similar to the conversations that we would have in our one- on- ones or on a walk. And also, if I saw DC tweet something, I would just take that and then bring that onto the podcast and then ask him about it. And so it was able to get all these ideas from things that were already happening. And the reason why I think Seeking Wisdom is what it is today, is because of this whole idea of document, don't create. I know we've heard Gary V call it that document don't create. But we wanted the podcast to be and still do just a real conversation about what's happening between two people, between Drift, between what we're learning, sharing the things that we're learning back to you. And I think that there's so many marketing and business lessons in what we discovered through Seeking Wisdom, which is, we didn't set out to create this show, but it just happens to be a conversation between two people, a fly on the wall. And I think that is what people want out of a brand today, which is being real, which is being authentic, which is being human. And so, my takeaway from this episode, little behind the scenes story of Seeking Wisdom, is focus on documenting. Don't create, right? If you've tried to create something, sometimes it becomes too much of a thing. We document everything. We record everything. We film everything and that's what people want today. Nobody wants to be marketed to. Nobody wants to be sold to. And so we never try to market or sell on Seeking Wisdom. We have a lot of funny and fun things like... DC created this way of asking, somehow, this way of asking for reviews, which was like a joke, which is like six stars only, has led to 500 plus five- star reviews. And I was on a podcast with Christopher Lochhead from Play Bigger the other day. And he's like," I don't know how you guys get so many reviews." Because DC has found this way of asking for reviews that's like funny, but it also gets reviews in. And so, to focus on documenting, don't worry about creating so much. The best marketing today is real. It's authentic. It's human. And I would love to know from you, have you created something. What's an example of something you've created in your business that is real, right? That is not this highly produced, highly curated, highly thought out thing. But what's an example of a video that you made where it's just you talking about something that's happening in your business? Maybe you have a podcast. Maybe you've done a webinar. Maybe you have a newsletter. I'd love to know examples, or tweet at me @ DaveGerhardt. Also hit up DC and let him know what you think about the early days and the start of Seeking Wisdom. And also let us know, what do you want from in the future? Right? We're going to have more guests. DC's launching his show. We have a lot to come to the Hyper- Growth Podcast network, which Seeking Wisdom is a part of. We have the Build Show with Maggie. We have Ops with Sean Lane. We have Growth with Matt Bilotti. We have Exceptions with Jay. We have my new podcast, the Marketing Swipe File, and we have this show, Seeking Wisdom. But I also heard DC is working on a little podcast of his own. So, it's crazy to think back how this conversation, something that started with literally just me trying to interview DC to get ghost written content has now turned into six plus shows, an audience of people that we love and feel like we actually get to connect with and talk to. The response from a podcast is unlike any other marketing channel, because you're literally in somebody's ears while they're at the gym. While they're making dinner, cleaning the house, going for a walk. You don't get that from a blog. You don't get that from many other channels. So, love doing this podcast. It's amazing. And just want to get on the mic for a couple minutes to tell you a little bit of the backstory, because I know a lot of people have been asking. So started off as quick interviews to ghost write some content, now turned into a whole platform in a network, and that's what's possible. I think today in marketing, if you focus on documenting, don't create. If you love the podcast, go ahead and leave us six stars. Only on Apple Podcasts, wherever you get your podcasts, Seeking Wisdom is now everywhere. Stitcher, Spotify, Apple Podcasts, wherever you listen. And we'll be back. Next week, DC and I are both back in town. We'll be back with your regularly scheduled episode of Seeking Wisdom. Have an awesome week. See ya.


In this episode of Seeking Wisdom, DG is taking you back in time...to 2015. He had just joined the marketing team at Drift. There was no content. There was no blog. And he had a busy CEO who was full of ideas – but who had no time to spend turning them into content. Tune into to learn how DG was able get more content from his CEO – and create the world’s first six star podcast in the process.