Shorty Awards Creator

I met today’s guest at a podcasting conference in Las Vegas 10 years ago when no one even knew what podcasting was. Since then I’ve never missed an episode of his show Venture Voice which he put on hold for a decade while building his other businesses, but just relaunched.

But he’s gone on to do amazing things including creating The Oscars of social media, The Shorty Awards, and Muck Rack. I invited him on to talk about all of it.

Gregory Galant

Gregory Galant

Muck Rack

Gregory Galant is the creator of the Short Awards and founder of Muck Rack where you can find journalists, get press for your story, monitor the news and report on the impact of your PR.


Full Interview Transcript

Andrew: Hey there, freedom fighters. My name is Andrew Warner. I’m the founder of Mixergy, where I interview entrepreneurs about how they built their businesses. And part of the reason why I do these interviews is because years ago I was at this conference in Las Vegas for podcasters, and I saw this guy Gregory Gallant. Must’ve been the shyest person in the room. Were you shy back then when you started

Gregory: I wouldn’t say shy, but I don’t know, maybe in different contexts, depending on what contexts I was in could, uh, not necessarily be the most gregarious person in the room.

Andrew: It definitely wasn’t your place beyond the fact that you were podcasting everyone else. There was trying to be. Like an actor an over the top, something in an environment podcasting we’re talking about over 10 years ago, that wasn’t really ready for it. You know what I mean? Remember, weren’t the podcast was what bobbleheads made for them at a world where nobody even knew what a podcast was anyway.

So in this room with people who wanted to be comedians and actors and do all that and shove it into the medium of podcasting was this guy who I felt was shy. And I love talking to people, especially shy people. And I said, venture voice what’s that. And Greg says to me, I interview entrepreneurs. I go, Holy crap.

I had no interest in any of this other stuff. I only listened because I’m a podcast addict. This I listened to. I went back and I listened to his podcast venture voice. I did not miss a single episode of his podcast to date. I have not missed a single episode of your podcast. We would talk about it. When I lived in Los Angeles with other entrepreneurs who are just on the edges of this whole startup ecosystem that was developing and his show was one that we were listening to and then the fricking guy stops podcasting.

So, okay. I still use his old podcast episodes for research and then the episodes break on his website. Gotcha. All right. This is why I’m charging. Because if I charge, then I make money from the podcast and it can continue to survive because it’s important to me that the podcast episodes I record and that the history that I recorded people building their businesses is preserved, but what’s he doing when he’s neglecting his podcast and neglecting his fans, he goes off and he builds these two companies that have done killer.

Well, the first is the shorty awards. Every celebrity in this new social media world, whenever the shorty awards go on is basically begging us their fans to vote for them on the shorty awards because Gregory gallon decided he was going to create an award ceremony where people’s votes counted. So Casey Neistat interrupts his blog incredibly popular.

Say, don’t forget, vote for me on this Kara Swisher. Who’s like the most serious above everything person out there says, and by the way, I, I probably shouldn’t tell you this because I’m above this. I, I don’t know exactly what her phrasing was, but you should vote for me on the shorty awards. So this thing blows up and this big event, it’s like the, the Oscars.

Yeah. Social media, And then. He goes off and he creates MuckRack. It’s basically a tool for anyone who is in the media to find reporters, to get alerts on new, to generate reports.

And so on. I only know this because Mark Cuban is not only a customer he goes and brags about anyway. So I’m a big fan of Greg’s. I want to find out about how he turned, how he built these businesses. I really there’s a little bit, I want to know about your podcast, but I’m really fascinated by how you decided to start these companies and how they took off.

And we’ll talk a little bit about the painful one that didn’t work out and we can do it. Thanks to two phenomenal sponsors. The first, if you’re hiring developers, you need to know about top talent. The second, if you’re building a website, I’ll tell you later why you should sign up for HostGator first, Greg, good hat.


Gregory: Okay.

Andrew: dollars and cents. How much money you making with muck rack? I feel like that’s the moneymaker. Give me a sense.

Gregory: we don’t, we don’t release numbers publicly, but we have over, uh, over 80 employees now we’re profitable and it’s been growing quickly.

Andrew: Fair to say over $6 million a year in revenue.

Gregory: Yeah. That’s fair to say.

Andrew: Okay. I get a sense based on the number of people that are on the team, shorty awards, is that a moneymaker or is that just a. Like a big celebrity thing,

Gregory: Yeah, that’s also a, it’s something that we run out of passion, but it’s a sustainable business. We have five people who are kind of year round and, uh, and it’s, you know, done, done well every year we’ve ran it

Andrew: but not a profitable business.

Gregory: it’s profitable, but not, um, Not a hugely pro yeah. It’s not like a software business where it throws off, you know, where it has that same profit potential, but to make something sustainable, you have to make up. Okay.

Andrew: What got you into podcasting?

Gregory: Yeah. You know, it was originally when I was in, um, when I was in college, I started my first business in high school building websites back when that was the new thing, my, um, Senior year of college. I worked at, I got this job I went to school in Atlanta, so I kept getting stuck in Atlanta traffic, uh, going to get to CNN headquarters.

And I hated Atlanta radio and the iPod had just come out and it occurred to me like, Oh, Potentially I could get, you know, content other than music on my iPod. Maybe I could download the news and MP3s and listen on there. And I was thinking, well, CNN has, you know, they had a radio syndication network. I’m like, I’m sure they have it.

So at first I was just podcasting. Wasn’t a thing yet. I always just thinking like, could I get MP3s, uh, about, you know, the news or just any kind of content for MP3s and. Sync it to my iPod. And I started researching around at the time. It was considered RSS feeds with enclosures was the original, hot name of podcasts thing, but became podcasting.

And the idea was RSS feeds existed for news. You’d have an enclosure file, meaning it would link to the MP3 and then you could have a pod catcher is they called them and that would download it and then sync at the iTunes, which didn’t yet have anything like this built in. So I, I thought I was just such an interesting idea that I could create this really compelling, alternative to radio.

And then as I was looking at it more, I saw there were just a couple of mentions back then a podcasting in so many people. Now it surprises me that they don’t know that the name podcasting comes from the idea.

Andrew: My wife didn’t know that until a few days ago, I just assumed that they all knew it. But I think we assumed that everybody knew what podcasting was back then, but really until recently, maybe. Cereal. Most of the world had no clue what podcasting is and you know what? I wouldn’t be surprised if today still most of the world doesn’t know what podcasting is.

Gregory: Well said. Yeah. And I, and you know, I, I come even a lot of people who love podcasts. Now I tell them I started in 2005 and they’re shocked. They’re like it existed back then. They, you know, they feel like it was just invented by years ago.

Andrew: We’re talking about before the iPhone existed. For me, it was, I discovered podcasting as a listener because there was this guy on, in gadget who was somehow. Kicked off of in gadget and is a whole trace of him being on the site was removed, but he was such a geek. He said, here’s how geeks run like this watch for tracking how you run.

I thought, I didn’t know. You could do that where you run, how fast you were on and put it on a computer so you can analyze it. And then here’s how you can get podcasts on an MP3 device. I think he didn’t even have an iPod and I thought, well, you could do that. And I started. Downloading a few and then I would save them because you never know if they go away or something.

I don’t know why I thought I would, uh, I would relisten to them, but they felt so precious. And then I encouraged my sister and her boyfriend who were both, um, They weren’t a comedy. He was a comedian. Um, and I encouraged them to create a podcast and they actually did it because they were also Howard stern fans like me.

I used to listen to talk radio as a kid, a lot rush Limbaugh, Howard stern, anyone, if they had it, um, Bob grant. And, uh, I encouraged him to do it. He was a fan of talk radio. He did it. And then the thing kind of took off. That’s why I ended up in Las Vegas at that podcast conference. So you were listening, you saw it emerge.

What made you say? I think I should be interviewing people on it.

Gregory: Yeah, so basically I got really into it. I was graduating school and I always wanted to be an entrepreneur ever since I started that business in high school. So as I was graduating, I’m like, all right, I just want to get into podcasting and learn about it. What’s the best way to do that. Let me try starting a podcast.

And then I thought to myself, well, what should the topic be? And having been an entrepreneur, I also, I was so spent this summer, uh, working at a venture firm and what, what I was always super hungry for was just knowing like how. Well, what made it work? How did these entrepreneurs scale up these companies?

And at the time it’s, you know, it’s easy to take for granted now that you can get all this content, thanks to people like yourself and, and entrepreneurs, writing blog posts about themselves and VCs blogging and all that. But back in 2005, There was almost nothing. I felt like all there was, I subscribed to inc magazine and entrepreneur, and there’d occasionally be an article about an entrepreneur in a paper, but it was always a 500 word article.

And it would be like, Hey Andrew, who started this business? Then one paragraph later, it’s an, I got 10,000 employees and I was like, wait, what they do between like starting the business and even hiring their first employee and getting to 10. And my, I just, I was so hungry for that information and it just wasn’t anywhere public on the web at the time.

So I thought like, Hey, that could be a really cool show through. We’re just interviewing these entrepreneurs about how they got started. And I just thought. When it comes to worse, I just wanted to know that myself. So it’ll be, uh, these some fun interviews to do.

Andrew: And what I remember you doing was taking. Your microphone to their offices and recording, getting them to do interviews with you by calling them up, you’d call up the office of the company that you want to interview. Do you remember the first interview that you did?

Gregory: Very well, Dick Costolo, who was, yeah. At the time, the CEO of B burner and RSS analytics company, uh, at the time that was had in the podcasting scene, because podcasts are, you should use it to measure it, measure their podcasts. So I call their, uh, I call their main number. I’m like, Hey, who can I speak to about sending up an interview with your CEO?

This is Derek. I’m the CEO. I’m like, Oh, Hey, I’d love to set up a time to interview you on my podcast, venture voice. Meanwhile, you went to the website. It was like just the logo. Nothing, nothing there indicating credibility, but I don’t think he’d ever been on a podcast before and podcasts are just so new.

I think he was intrigued by it. So he’s like, Hey, give me a call on Monday. At 1:00 PM that the person was over the phone and he’s like, but one condition I’m like, yeah, whatever the phrase, I didn’t say it, but you’re the first guest he’s like, you have to call me on my cell phone. And now I knew nothing about audio prior to that, but every piece of advice I read at the time, it changed a lot since due to avoid.

But every piece of advice I read at the time was never doing interview on someone’s cell phone. Cause the quality was really crappy on cell phones back then. Uh, but yeah, I took it. I could, yeah, it sounds like, yeah, sure. Sorry. I have to call you on your cell phone, but I’m just curious. Do you mind if I asked you why he’s like, yeah, we only have one line here.

So, if I’m on the phone with you for an hour, customers, won’t be able to get through like, that’s a good reason. And then of course, for anyone who has sit down with the Casa, that I ended up eventually selling feed burner to Google for a hundred million and then became the CEO of Twitter who took Twitter.

Andrew: In the interview you asked him, um, do you think there’s a bubble? And we’re talking about 2005, is it really called a web 2.0 or bubble 2.0, I think was, was one of the things that you guys discussed, which just goes to show throughout the Internet’s history. There are people who think that it’s over-hype overexpanded meanwhile, hardly anyone still use.

I thought until COVID everyone was buying their groceries online. Cause why would you go into a freaking grocery store? Little did I know even today, most people do not. Buy their groceries online. Um, you kept on going. One of the things that I remember being disappointed by was you did not stay in. And the reason I keep referring back to the past is we talked when we met in Vegas, but also, um, after I started podcasting, I reached out to you and I said, would you let me interview you and ask you, uh, about how you do it?

At the time, by the way, I thought, Greg, you were a little bit, you were very gracious and you said, yes, let me answer all your questions. But I felt that maybe you were a little bit threatened by it to be open.

Gregory: Sure. Yeah. I mean, it was a, you know, very early time growing that all, but, uh, yeah, I mean, I think venture voice, I think that was probably the first podcast of its kind like just interviewing entrepreneurs. Uh, I, I hesitate to make the definitive statement like that because the Internet’s such wide place.

It’s easy to miss something, but, um, I’m pretty sure it was, or at least the first one that got out there. So yeah. You know, there’s always that element as an entrepreneur, especially when you’re starting out, that you want to keep putting, you’re doing specials. So on one hand, you want to help other entrepreneurs out and invite them in.

But on the other hand, you don’t don’t lie to a. Invite too much competition. When that’s your main thing.

Andrew: Meanwhile, you have to be glad that you did it because first of all, you helped me. I was going to go anyway. It wasn’t like without you, I would have been in trouble, but it created a relationship. You ended up moving on to other things anyway. And then when you came back, you know, you can count on this guy who you invest in, in a friendship with, uh, to be there, by the way I

Gregory: percent. I do have to say in many years in my career, they’ve been people who. I thought I was competing with and ended up being great partners either because there are businesses evolved in different ways or people end up at new companies. So I think it’s a great, great philosophy.

Andrew: It happens to me a lot though. I remember one guy competed with me, called me up out of the blue. I was so angry at him all the time, but I held back because I went to Dale Carnegie training. He ended up buying my company, you know, like the previous company, right? Like this whole thing that I’m so glad I held back on, uh, was actually good.

Do you have any examples of that, of someone who you thought was competitive with you over the years, but ended up being a partner or working with you in some way?

Gregory: that’s a good question. You know, we have a, I mean, through MuckRack we have a number of, uh, partners now where early on, you know, it wasn’t exactly clear how we both, um, Where exactly we both fell. Like we just completed a great partnership with business wire. That’s going extremely well. And, you know, broadly we’re in the same area, PR you know, kind of PR services.

And, you know, we could have decided to compete with each other and instead it made more sense to work together. And it’s been, uh, extremely fruit for our relationship. Know the other one, you know, even outside of that, I found. Even when I have direct competitors who I’m never going to partner with, there’s this weird thing where I’ve got some to become friends with with many of them and even go out to dinner with some of them and.

It’s the weirdest thing where it’s like, even when we’re direct competitors and it’s like, we know that there’s no way our companies are ever gonna, um, partner. And, uh, you know, as we are speaking pal, they are teams are fighting over the same deal, but there’s also no greater compassion you can have with someone than your competitor.

Cause you all deal with the exact same. Issues and dynamics. So even if I haven’t dinner with a great friend of mine, who’s an entrepreneur in a different field, you know, they’re not going to relate to me on all these nuances of my industry or is the direct competitor who knows all that. So, you know, I found it, you know, the, the market’s out there I’ll really dig in and, uh, there’s lots of, um, Opportunities.

I found it’s been just great to develop friendships. And then also I’ve had several times where, yeah, it might be somebody who’s a competitor now that they, they leave and there’s a new CEO and then it’s a friendship that I still have. So there’s, uh, there’s, there’s been quite a few instances like that.

Andrew: Let me close out venture voice. And I should say to anyone who’s listening, venture voice, he just rebooted it. He started it off with Mark Cuban who came on and said, I’m okay. Customer muck rack. Let me do your ad for you about why muck rack is so helpful. For me, gives me better alerts about it. Um, uh, news stories about me then Google and it’s useful in all these different ways.

And so, and he also did a great interview with, uh, Mark Cuban on the venture voice podcast. But I’m closing out with this. One of the things that’s stuck with me over the years was when you did do that interview with me, where you answered my questions about podcasting. I asked you, do you stay in touch with these.

Entrepreneurs thinking this is an hour of intimate conversation with somebody who you get to know, and they get to see that the caring that you have for them. And you said, don’t know sometimes I stay in touch, usually not. I wondered. What did you get over the years as an entrepreneur from those interviews that you did when you started out?

Gregory: Yeah, I’d say a few different things. You know, one is a God. I learned a ton prime it, yeah. As you can imagine, as you get from listening to it, but, uh, since you’re, you know, it’s always more visceral when you’re the one actually having the conversation that said there are plenty of things. I didn’t learn from it.

One, one funny irony I noticed was, uh, they would, all, many of them told me the thing that the most fatal mistake you can make an accompany is being too early to market or any tech company at least. And I remember there was this part of me. It was probably because I was younger. I was like, yeah. Yeah, old man.

But you know, I I’m sure I’ve just got to make it work and share it out for you to, I was just too early to podcasting back in, uh, back in Oh five for some of the things I was trying to do. Uh, but.

Andrew: sorry, we’ll get to that. I actually want to get into that. Um, but yeah. What was it that you got that was helpful then?

Gregory: Yeah. So, so what was helpful? I mean, it was definitely, it was definitely great for networking. Uh, met lots of great people. I mean, men, you know, some of them I did stay in touch with and created some great relationships out of a meeting of listeners like yourself, many of them, I ended up, uh, you know, Getting, uh, you know, building relationships that have lasted me till till today.

And then it actually led very directly into the two businesses I run now because it got me like right on the forefront of where technology is going with web 2.0 is he caught it back then and in social media, uh, so you know, what example was having a Williams on. Who at the time was working on this extremely hot company.

And it was hot because they’d managed to raise $3 million, this consumer internet company, which today would be considered nothing. But back then was a huge deal. Cause everyone was still shell shocked from the, the bubble in 99. And, uh, he starts Odo, which was meant to be a podcasting directory. It was the hottest podcasting company at the time.

And I had avant and we kind of stayed in touch because we were both doing podcasting businesses and I’d launched a podcast ad business on the side of a venture voice and then Odo didn’t work out. So they pivoted to a little side project called Twitter. And I encourage anyone to look up the original tech crunch article about Twitter, where they’re like, yeah, this is kind of cool, but EBS, a real fool for not focusing on Odo, the great business that he’s working on.

Several of them thought they were just being reckless, almost doing this Twitter side project back then it was TW TTR, but yeah, it’s following him. So I signed up to Twitter pretty early. So I got my first name on there at Gregory. Just cause it was open. It wasn’t, I didn’t call on a paver III then. And then it was from being on Twitter in those early days, that led to the idea for the shorty awards and then doing the shorty awards, seeing how much press that got led to the idea for MuckRack and the rest is history.

So I don’t know that I’d be in the business I’m in today, if it weren’t for podcasting. And in a way, I don’t know if Twitter would exist, if it weren’t for podcasting because, uh, You know, and, and, you know, Jack and, and all those guys that have never gotten into business together,

Andrew: So let’s talk about that one company radio tale that you were starting to say is a little bit early radio tail did online ads for podcast, right?

Gregory: that’s right. So started it soon after venture voice, it seemed obvious to me in launching venture voice that. These people doing podcasts will want to find a way to make money and be sustainable. And it seemed like the rest of the web advertising would be the way to do it. And there were kind of two ideas behind it that at the time went after both of them intertwined, which was on one hand, it would make sense for a company to aggregate the sales.

Of these podcasts, because it wouldn’t make sense for every podcast or to do their own sale. And two that the pod that the ad should be inserted dynamically. So in other words, rather than you doing a static ad where you read the ad and then it’ll live with that podcast for the next 10 years, even though that advertiser might leave you.

That it’d be better to serve the ads at the time the person downloads the podcast so that you could say, okay, well, you know, just like every other form of, uh, web advertising at the time, like, okay, we’ll give you 10,000 downloads for the, to put this ad in.

Andrew: that we have with advertising and podcasting. Right now you sell an ad. If the interview that I do, the ad in bombs, the advertisers still is paying the same amount as if. I had one that did three X, the number of downloads, whoever was in there suddenly got a windfall. They didn’t know why.

And it’s because you can’t dynamically. We don’t dynamically serve it up. There are starting to be waste. And so I get that. You’ve found that. Did you sell ads at the time? I don’t remember if you had ads or not.

Gregory: I did in some of them. Yeah. And then we did some, a Pew that I sold just for venture voice, and then some of them that were, uh, Dynamically inserted where we sold them through radio tail and inserted them in a bunch of podcasts, including that.

Andrew: So you created the software to dynamically insert ads.

Gregory: Yeah. We actually built dynamic ad serving software in 2005.

Andrew: Because then what it would mean is that you would have to have podcast hosting software to host the audio files, which were very expensive to host back then and know where to put the ads and serve them up dynamically.

Gregory: We built all that and actually the way that we built it to get around the hosting costs. It’s a great thing to point out because you’d have to host everything. We built a redirect. Uh, so we gave people the analytics for free. So you just put a redirect in front of your MP3, but then if we were serving an ad for you, only when we would serve the ad, we would then use that redirect to actually serve the MP3 itself with the ad dynamically inserted.

And we even had a.

Andrew: How would that work?

Gregory: So in other words, like when you, uh, when you post one of these podcasts, it’s, it has a URL on the web, that MP3. So you would. Uh, put this to prefects to it. And you would say radio Mark, that MP3 meaning that it would go, it would first ping our server.

When someone someones a iTunes account to whatever they use to download their podcasts, who would first ping our server and then push it to wherever the MP3 goes from. So we could track. And tell that there was the, uh, there was a download, but if we were going to serve the ad, then we’d, instead of redirecting it, we would just serve this dynamically, generate MP3 with an ad in it.

Andrew: Got it only if there was an ad to go out, you would serve it out. Otherwise it’s too expensive to serve the MP3. If you’re not making money from the advertising, but still it would mean that you would dynamically add the advertising into the podcast episode, which is pretty impressive technology, especially back then who built it?

You keep saying we, at this point, who’s the, we.

Gregory: Yeah, it’s myself and a friend of mine, a guy named Aaron Quint, and we co-founded the company. He did the tech. I did the, uh, I did the business side and, uh, we’d kind of worked together on the product.

Andrew: I find that podcast advertising was really, really hard until about four years ago or so. How was it back when you were doing it? Yeah.

Gregory: Brutal, uh, yeah. Cause there were. There were a few elements, you know, looking back at it, it’s super clear to me what the problem was at the time. I was very caught up in like all the challenges of building the business and making the sale and all the tactical stuff, but what took a while to become clear.

And yet it’s obvious in retrospect, it was just too early in the market. And you know, now it’s like, If you tell me about a podcast when we’re out to drink site and can, uh, I can just pull it up on my phone and be listening to it. 10 seconds later, as I’m walking away from the bar back then it was like, okay, I gotta go home.

Uh, really early out. I had to actually download third-party software to get it, but even after iTunes had it, I had to have iTunes open. So my computer would sync with, so my iTunes would sync to download the file that I had to sync my iPod. And what I learned doing, it was a lot of people wouldn’t even sync their iPod a daily basis.

They charge their iPod just into the wall. And they’d only sync it every month, because if you didn’t before podcasting, you would only sync your iPod when you bought a new album. So there wasn’t even this, um, habit of sinking your iPod and then even sick of the iPad. It wouldn’t work that well. So all the times I would leave my own home.

And then realize that the sink didn’t work and be disappointed that all my podcasts weren’t loaded on my iPod and I’m fairly technical, the savvy guy. So there were just so many challenges into my own mother would model listen to my podcasts. I had to burn it on an audio CD for her, so she could pop it in her car, a CD player and take elicit.

So it’s just so hard. They just weren’t. There just wasn’t the volume of listenership back then that there is today. So it was really hard to convince advertisers to deal with it because podcasting has all these disadvantages relative to the web. Uh, you know, that it’s harder to track. Uh, well, it, you know, through the choir here, but there are all these challenges to podcasts that you don’t have on the web where the web taught every, every advertiser to expect all this trackability.

Podcasts has tremendous strengths. I still believe in podcast advertising and think it’s a great format, but unless you had the volume, you know, it was, it, it just made another challenge to explain it to advertisers. And without that volume and with so many advertisers, not even knowing what podcasts were or having ever used it themselves, it makes it so much harder.

Andrew: Yeah. And so that’s the big problem. You’re way, way ahead, way ahead of where everyone else was. And you were thinking they would get to you and eventually they did, but that would have been a slog for years and years and years. You told me when we were talking privately, this was painful for you to admit defeat and close up.

Talk about that a little bit.

Gregory: Yeah, so I I’ve been doing videos, tail, uh, Trying to think exactly how long it was before. I really, yeah. It’s about two years in total. There, there was some point before the two years where I’d, um, I think I’d realized it wasn’t going to work and it was more of a wind down period, but yeah, I went down it really hard and you know, I’m not, uh, I’d never had to close something up before for it not working.

And I just had this leave, you know, you can, I mean, I think it’s something that every entrepreneur shows with, but where you, you tie up your own identity with the business. So there is a bit of me like the business fails. Does it mean that I failed? I didn’t think of it so much. You know, I think a better way to think about it is like a scientific experiment, you know, like, let me try.

I have this hypothesis, let me try it out. It didn’t work. The market wasn’t ready. So, you know, it was for a while there, it was wrapped up with me where I’m like, I’m going to make this thing work by sheer force of will. And you know, you hear as part of the hard thing about it interviewing entrepreneurs, because you hear those stories where someone’s like, you know, the whole world didn’t believe in me and I pushed it through and then they got it in that it worked.

So separating that from the moments where it’s like, Oh wait, this, this really is like, I tried it. I gave it my all and it’s time to move on to something new that that’s what I, uh, I really struggled with. And, uh, it was a hard, hard moment to, uh, to hit.

Andrew: You’re talking about ed Williams famously in, uh, Jessica Livingston’s book of interviews with, with the big success stories of web 1.0, she talks about how I think he was basically sleeping by his server in wherever it was that he was hosting. He actually got to touch it. Because he was the only one left at the company and he had to keep the server up and running while he was keeping, what was the company called?

It was called blogger while he was getting bloggers to actually work with its users. And it was a slog, but eventually it did pay off for him. He sold it to Google. That’s where he made his bones and allowed himself to raise the whopping $3 million for Odo. So I get it. In retrospect, you did make the right decision.

You really could have been in for a world of pain, trying to force this on a world that wasn’t ready. You created the shorty awards. How

Gregory: yeah, the shorty awards. It’s funny. The shorter ones I thought was the least five old business idea I ever had.

Andrew: was it a

Gregory: And I didn’t even think, sorry.

Andrew: I’ve been wondering, was it a business idea or you

Gregory: No, it wasn’t even a business idea. Yeah. So I saw I was on Twitter in the really early days. And a lot of people don’t realize like how long Twitter took to take off.

You know, it started, I believe in 2006 and then didn’t really take off till Oh eight and. I was on it early, but it took me, it took me a few months before I really got it. There were a few months, I think, early on where I would log in once a month to plug a link that I had or something and that’d be it.

But I started getting into it in Oh eight. That’s when it felt like there started to be a tipping point. And what struck me about Twitter was unlike Facebook, which Peggy got on when it was being rolled out to colleges and I was in college. And, uh, the other social networks that came before it, they were all closed down.

It’s like Facebook at the time. It was just you and your friends. There was no concept of like being good at Facebook. Cause it was just something you’d share photos with just your friends with there was no public content. Twitter was so interesting because you had these celebrities and journalists and subject matter experts getting on and sharing stuff about their fields.

So I was like, Oh wait, this is more like blogging or almost more like TV or any form of media where you can actually be good at it and find an audience. Kind of like podcasting in a way, which is maybe why I came out of podcasts thing. So I was like, Oh, people can actually be good at Twitter and to talking about different topics, but Twitter had no discoverability at the time.

So if you were like, Hey, I’m interested in sports. Where can I find people tweeting about sports or I’m interested in, uh, in, in science, where can I find scientists on Twitter? There was nowhere to go. So. My first thought was like, Hey, can we aggregate, uh, can we figure out who the best people by topic on Twitter?

Andrew: Uh, yeah.

Gregory: and I was like, um, we could crowdsource that in a cool way. People could actually tweet out who they think is the best fight topic. And then I was thinking, well, how do we get them to want to tweet out who they think is the best by topic? Let’s call it an award. And so, uh, the banding budget was, uh, was $8, which is that would have cost to buy domain name and GoDaddy back then.

So it was playing around for open domains and thought tweets are short shorty shorty awards, and I pitched it to my now, uh co-founder um, uh, who who’s, uh, who’s con I continue to work with and is our CTO a amazing programmer? Uh, Lisa, I’m all in. I pitched him on the idea and I’m like, you know what? It’s not going to make any money, but I’m pretty sure we could build this in one weekend.

I think it’d be a lot of fun. He said I’m in and ended up taking us two weekends, but we literally built the whole thing in, in two weekends. Uh, you know, why are paying meeting right in the copy, coding it. And we put it out there.

Andrew: And what it would do is anyone could tweet out who they thought was, should win a shorty award in whatever topic like maybe startups, I think was one of the topics you tweeted out. And the shorty awards website would just calculate who got the most points and then put together a leaderboard based on topic.

Am I right?

Gregory: Yeah, exactly. And even more, you could even make up your own categories that first year. So you can make up any category you wanted. We said, we’d only give awards in the official categories, but it was kind of this fun crowd source site. And I should note it’s since changed it. That’s not how it works anymore.

It’s gotten a lot more rigorous, but that first year it was this kind of free for all. Anybody could tweet out, uh, any vote for whoever they wanted.

Andrew: Okay. Here’s one, here’s one of mine, January 16, 20 2009. At shorty awards. I vote for at Mark in the shorty awards finals for. Hashtag photography because he makes the rest of us look good. That was Mark, who was taking pictures of people at the time in tech. And because I would do that, everybody who was following me would see at shorty awards back then Twitter would just let everyone who’s following person.

See it, regardless of what the first, uh, uh, mentioned was in everybody would go and see what is the shorty awards? They would then say, well, I should go and nominate someone or I’d like to be nominated. Let me go and ask people to nominate me. And this thing grew virally and then the next step was live.


Gregory: Yeah. So when we put up the website, we made no promises that there would be an in-person event. Uh, but after it, when, after it went viral, it became the top, top trending term on Twitter and New York times wall street journal, BBC, all, all reached out to us in those first 24 hours to cover it. And I realized like, Oh, you know, people go to actually want to come to this thing.

It would be better put on a show. And I didn’t know how long the Twitter fad would last. So I’m like we gotta do this soon. So I just announced the show would be two months from that date. You know that about, about two months from right after it went viral and looking back at it now, it just seems insane to do that.

Cause I know how long it takes to plan an event, but we just sit that we’ll be at two months, we didn’t know any better. I’ve never worked so hard in my life, Andrew. I called everybody. I knew. So when it went viral, we didn’t have sponsors, you know, a venue. We didn’t have a host. I was just a website. And so I managed to get the, uh, the Knight foundation and Pepsi to sponsor at that first year.

Uh, the venue we used, I did the whole deal on a handshake, no contract. No insurance requirement, just to handshake with the venue owner. And again, looking back at it now, knowing that we signed 30 page contracts with then use and edit, while at least we did before the pandemic and, and we’d sign 30 phase contract of venues and do extend extensive insurance, like, is this season say to me that I just did it on a handshake, but I didn’t know any better.

So that’s what we did. And the first year, I mean, Oh, and we also got. It was called Galapagos art space in Dumbo, Dumbo, Brooklyn, which is right by down under the Manhattan bridge overpass. And at the time now it’s a really hot area. And, you know, there’s always people taking photos there, but at the time it was like just when it was starting to turn around.

Oh. And I also got a MC hammer to come that first seer by direct messaging him as well as Gary Vaynerchuk, who is, uh, just a, a hot, you know, often coming blogger at the time.

Andrew: And the reason that you got, um, MC hammer is MC hammer was interested in technology. He was interested in, I think, investing in technology, he was part of the whole tech crunch world. And so by reaching out, you were able to get, let me ask you this you’ve said this was just like a thing that happened.

You’re an entrepreneurial guy you think about business and have, since you were young, Why wouldn’t you get carried away with this without saying to yourself, where is this thing going? Especially considering that you already had, uh, a painful experience with a business before.

Gregory: Yeah, I knew I was, you know, as painful as it was. I knew I wanted to kept trying. And, uh, and I guess that was one thing I learned from venture voice, and I’m sure you see it too, doing these long form interviews. You, you hear how many failures people have on the way to success that they’ll edit out of those short version of their bio.

And, you know, I don’t tell this story when I only have 30 seconds to introduce myself just cause it wouldn’t, uh, Within fit, but yeah, I knew I wanted to do more stuff. The other thing that the shorty awards taught me was the importance of timing and what traction was because when I was slogging it with radio tail, like that was my first product based business.

In first business where I, you know, where I put, um, a lot more pressure on it in terms of like, you know, building a product and all that versus, uh, just doing, uh, doing consulting. And so I didn’t, you know, I thought it would always be that hard to get people interested in this Shorty’s felt easy compared.

Cause it was like, it’s the same guys, a person who did radio tail. And I was putting in. They say amount of effort, but I was getting a ton more return for it. Cause the market wanted what I created. So people were excited about the shorty awards in a way they were never excited about radio tail. So I’d have these, you know, I do the calls, I’d put all that effort in, but I get a much higher win rate, you know, between, when I talk to people and.

Some someone saying yes to my idea. So I got to say the shorty words it’s really, the first time I really felt like felt what it was like to have traction or, you know, product market fit is that later became known. Uh, and it was really invigorating. I mean, I never, it was one of the most fun times of my life.

Just putting that together in their first couple of months.

Andrew: All right. That kind of feeds into my first sponsor. Paul Graham, October, 2020, put up a early work. I, I actually had my ID had read it to me while I was making myself some lunch. And then when it accidentally started repeating it, I said, I want to hear it again. I didn’t stop it. This is so it was so meaningful.

He says, look, one of the biggest things, holding people back from doing great work is fear of making something lame. Fear of making something lame. And this fear is not an irrational one, many great projects go through a stage early on where they don’t seem very impressive even to their creators. You have to push through the stage to reach the great work that lies beyond.

But many people don’t, most people don’t even reach the stage of making something they’re embarrassed by let alone continue past it. They’re too frightened to even start. And then he goes through an SSA about all the different ways that you can. Get past it without compromising your good taste and your sensibility, how can you create something lame?

And he says, one of them is just make it a hobby or do it as a way of being of expressing your curiosity. And this is partially what you did with the shorty awards. It’s also partially the way that I talk about HostGator, my sponsor, which is HostGator is so inexpensive for hosting websites. In fact, for under five bucks a month, you can get an unlimited hosting package, meaning they’ll host as many domains as you throw at them.

Which means that anytime you have an idea for an awards, this for a site that sells that, whatever, you don’t have to think about it, he’s talks about sketching it out on paper. This is the same type of thing. Sketch it out on the internet for people to see, or frankly, maybe say, save it and keep it private for yourself to see what it looks like to decide whether you want to continue with it or not.

And if it captures your heart, if it feels right, you’ll know it more, when you see it and get past that, that. In your head part then if you just keep it in your head. And so I’m going to tell everyone, listening to me that if you haven’t yet played around with the site, forget creating a site for business purposes, forget the more proper thing that you should be doing.

If you haven’t yet just sketched. I urge you to go to sign up. And when you throw the slash mixer at the end, really, of course, I get credit for sending you over. I don’t get paid any extra. They paid up for a bunch of ads, regardless of how many orders they get, but I want them to know that you’re coming from me.

And so you’ll be helping me out that way, but you also help yourself because you get the lowest price that they have available and you’ll get an incredible hosting package that would allow you to experiment by putting websites up. Do you, maybe one of your ideas ends up being like the shorty awards, this thing that you thought was just a, a game, a play a thing, but actually becomes this life-changing experience.

All right. Shorty awards, first event successful, right? People came.

Gregory: Very successful. Yeah, almost too successful. We had a venue that could fit a 300 and we had 400 people show up. So it’s actually a little, I mean, it was very successful. It was a little bit of a, of a mess because they were very important that people couldn’t even get to the door because we didn’t have that level of organization the first

Andrew: who was the one?

Gregory: Well, I I’ve got a receipt to say it. So John Borthwick, the founder of Bader works is extremely gracious in helping in helping, uh, to get started and connections. And then, uh, he was one of the people couldn’t get in. I felt so awful. I called him the next day to apologize, and he was extremely gracious about it.

Uh, but, but him and yeah, many others, it was just like, I was terrified. We wouldn’t have enough people show up and we had the opposite problem. And you had to just organize it in two months with people who aren’t professional, who don’t come there at an event, production background makes it crazy, but it worked and it had so much by the end of the first year.

Yeah. You can get away with that. By the second year we hired professional event producers, and that’s not the kind of mistakes you can make twice and have any kind of reality. But we were forgiven by the community that, that first year.

Andrew: I want to close out a shorty awards by asking who are some of the big names who’ve shown up over the years. Lizzo, I think performed. Am I right?

Gregory: That’s right. Yeah. We have Lizzo perform panic at the disco. Amanda Palmer, uh, on the music side, we had a Michael Bloomberg Val, who was the mayor of New York come not to be honored for being the mayor of New York, but for being the mayor of city hall on Foursquare. And delivered an excellent speech about that.

Andrew: Okay. Anyone else? Um, Casey Neistat did end up winning that year, right. And

Gregory: yeah, that’s right. Casey. Neistat’s actually won one twice and, and yeah, it was there. Thing has been to three of them for winning twice. And then, um, he, he’s also done, uh, been a presenter other years. You’ve had MKBHD the top, uh, top gadget viewer on YouTube. Come to accept the award. Uh, Tyler Oakley, many of the biggest names on a, on social media and within the influencer world, it’s kind of this.

You know, put in it, they might not know the askers, but they know this. And, and, you know, it’s weird for me because I dunno, you know, I still think of myself sometimes as a young guy in the market, but then I meet these influencers and they’re like 19. So the shorties have existed since they were like seven, you know, and anything that exists before you can remember.

Has this, um, or, uh, to it.

Andrew: of permanence.

Gregory: Yeah. So like if you met someone who was a hundred years old and was involved in the first Oscars that took place 80 plus years ago, you’d be like, Oh my God. So it’s a, you know, I think there’s like this weird dynamic for these 19 year olds who like someone started the sorority or it’s like, you don’t even think about the fact that a human being started at award show this,

Andrew: always existed.

Gregory: Yeah, like the Nobel prize or the Oscars. You don’t think of them like Microsoft. I go, yeah, of course. Bill Gates started Microsoft, but when you hear

Andrew: about the shorty awards, the way that you, obviously, everything we’ve talked about is interesting, but what’s maybe more impressive than all that is how relevant you kept it. You started out with a name that almost limited you to Twitter, but as social media, stardom expanded beyond Twitter, you were able to keep up with that.

And more importantly, As the people who would have been popular back when you started age and newer people came in, who would have every reason to say I don’t, I reject the older generation. I reject the Twitter generation. I am, whatever is the new thing you manage to keep up. And part of it is because you ask people to vote.

And the reputation that you’ve had from the history of other people, who’ve asked to vote, you get new people who then go and promote it to their audience, which then brings in a younger right. MKBHD is bringing in a newer audience. Then whoever won the first one, am I right?

Gregory: Hundred percent. Yeah, I think that’s a great point. It’s this big pressure to constantly reinvent it because the medium, we honor always changes. I would always think like the Oscars haven’t really had to do much since they added sound to movies and that’s been kind of a continuous stream, but for our media, yeah.

It’s always changing. So you have to keep integrating these new, uh, these new communities into, into it and changing the

Andrew: the Webbys do it. You did it. Why didn’t the Webbies do it. The Webbies was the award ceremony money for a long time. They didn’t keep their cool. Why not? You’re in the space.

Gregory: Yeah, I think, you know, the shorties were always about honoring. We started with honoring individual, like honoring the actual creators on these social platforms. And then we’ve, we’ve now added this big part where we also honor brands, whereas the Webbys started the opposite where they, they started with this paradigm of honoring websites.

And then they’ve had to adapt to this newer world that we’re in. So I think Kylie had been too, but I, you know, I think it’s that classic innovator’s dilemma where, where they were, they were built around something very different than what we were built around.

Andrew: That makes sense. You’re right. You, you banked on the people on the celebrities. They banked on the brands and the websites. And there was a period where the websites were the shining, but once people could blog, it meant that we could see the people building our websites and then we care more about the people than the product.

Okay. All right. Second sponsor. And then I want to understand how

Gregory: Sounds like you’re about to launch into another HostGator ad.

Andrew: I’m going to launch into now a top talent, but I can’t do a great segue into this. All I’m going to say to you is you asked me how top tout, what top tower was before we got started. How do you hire your developers at MuckRack?

Gregory: To hook her. Correct. Well, find them any way we can.

Andrew: All right. I’m going to give you another little technique to add to your, to your repertoire. Keep all the things that are working. But when you have this one position, that’s hard to fill that you’re urgently needing to fill, go to, hit the button, or ask your CTO to hit the button and schedule a call with hop towel.

What they have is a network of some of the best developers in the market and some spaces they’ve got all the best developers, all the leaders. In their network available to work with you. And the reason that I say go to them is challenge them. Say, we’ve got this big project. I don’t know how we could do it.

We don’t believe that you can do it, but let’s see what they come back to you with. What they will often do is go and find within their network of people. Who’ve been pre-screened, pre-vetted, pre-tested pre everything. People who’ve done. The project that is new to you. That is urgent to you. They’ve done it before sometimes several times before.

And they will put one or two people like that in front of you, Greg, or in front of your CTO. You do a zoom like I’m doing with you. If you like the person you can hire them often get started within days. If you don’t, you’ve lost nothing. It’s not like you’re paying for even an ad. You just asking them to go prove that you, that they could do this.

I’ve had people do this, Greg who have huge, um, networks, we say, you know, I’d rather have the speed. I’d rather have the expertise and they go to top down. I shouldn’t say people, I should be specific. We’re talking heat and Shaw. We’re talking Neil Patel. We’re talking several people who I’ve interviewed here.

Who’ve gone on the record and said, dude, I’m not getting paid by. Top-down I’ve hired from top talent. They’re not good. Not telling me you can hire, I’m saying add them to your repertoire and talk to them. If you do, you’ll be blown away. If you don’t. I’m always here. Say, Andrew, you lied to me.

I’m going to say that because I know most people are going to listen to this. They’re going to thank me for introducing them to talk to Alan. If you use this URL, Greg, even you, I know you’re incredibly wealthy, but I also know that you still care about money. You’re going to save a lot because if you go to a top, you’ll get 80 hours of developer credit.

When you pay for your first 80 hours. In addition to the no-risk trial period, by the way, I keep my camera on to see is this resonating with my guests or not? I’m watching you smile as I’m saying this. And it’s like, it’s making me want to laugh at them. It’s does sound a little bit like one of those infomercial promotions.

It’s like I did the ad. Well, but I also came across a little bit like those infomercial guys that we used to watch his kids. I’m assuming you watched them and liked them as a kid. Did you.

Gregory: I, I, you know, I, I wouldn’t say I like the infomercials, but I was always, uh, I was always intrigued by them. I couldn’t sometimes hard to look away.

Andrew: How do you do it? I want to know how to be a good salesperson. I was super shy. All right. My crack happened because of something you noticed at the shorty awards, what was that?

Gregory: Yeah. So that was, you know, another thing, uh, about the, it was funny when I was doing the podcast stuff, I was always struggling to get press and I got some press, but it was extremely hard. With the shorty awards, it was the opposite. So in those first 24 hours, New York times wall street journal, a BBC all caught us up wanting to cover it.

And, uh, and we had a lot of amazing journalists just come there and check it out. We had Brian Stelter there who now has his own show on CNN and, uh, all these journalists who are just kind of at the avant-garde of using social. So I saw, um, I saw there was this kind of. Huge interest in Twitter and social media by journalists.

And yet there was no way to find them all. And it just struck me, like, if you cared about any publication, why wouldn’t you want to know what all their journals, all the journalists on. I’d have to say. So, you know, if you’re interested in the New York times, when you want to see all the tweets from the people who write the New York times, because it was the New York times itself, aside from just a bunch of people writing it, uh, you know, or wall street journal or wired magazine or any other outlet.

So I had this idea that you could, and this was before Twitter lists even existed or before there was any way to curate a Twitter and social. So I had this idea, like, what do we just have a site that would just show you all the journals on Twitter in one place and show you all their tweets and organize them by publication.

That was the original idea. Again, it was like, I bet you, we could build this in a week. So I thought, well, it’s a week project, not a weekend project. I ended up taking two weeks rather than one week, but it was just like, let’s just build it. And my philosophy, by this point, it was one of the lessons I learned from radio Terra, radio tale.

I spent a lot of time really planning it out before launching and researching it and building financial models. And then the shorty awards is this weekend project they took off. So it’s like, you know, if you can build something fast, there’s no sense doing a bunch of analysis. Um, If you have a business idea where you have to like sign a lease and invest a million dollars.

Yeah. You better do your business, this plan and make sure the numbers work and do research, but you can build it in a couple of weeks then, like why bother researching? Cause if it doesn’t work, you just out a couple of weeks. So that was my, that was my philosophy at the time. I mean, still would be if I, if I had a band with the Vivanta where businesses, uh, and, and it just figured like, okay, let’s just get it out there.

So built it in two weeks. Put it out there. It became very popular journals. Like the day after launching it, I had, um, Have you remember David Carr? Uh, at the time Mike was one of the top media writers. He sadly since passed away, but he wrote the media equation in New York times, like absolute legend in journalism circles.

And he emails me the day after like subject line David Carr. Can you add me to muck rack? And we had over that year, uh, I learned later the New York times even linked to it in their internal intranet. So their own. Journalists could find their colleagues on social media.

Andrew: wow. It was just all you were doing was finding journalists, organizing them by category and, and showing their tweets.

Gregory: That was the original iteration.

Andrew: That was it so that you could find a journalist who’s writing about a topic you care about and see what they’ve sent, what they’ve said about them. Were you making it easy for your users to contact journalists or was it just a database of what they tweeted out?

Gregory: Just what they tweeted. We made it easy to follow them on Twitter, but that was it at the time, pile them on Twitter and find, I think we quickly added find their other social profiles too. If, if it was publicly

Andrew: today, it’s like so much now it’s like, it’s your ideal CRM? There’s a page that says everything about them. And on the right side, from what I remember, there’s a phone number, an email address, like truly research on the person and easy connection with them.

Gregory: Exactly. It’s come a long way since, uh, since the beginning, but it was that first iteration that we saw there was this resonance with journalists. Uh, they loved it because they wanted to, you know, have, uh, get more, you know, attention for their personal brand out there on the web. And then being in New York around lots of PR people and kind of knowing that community.

I talked to PR people are very PR savvy entrepreneurs. And they would just be like, I love muck rack. I use it to figure out who to pitch. I was like, you guys don’t have software that does that already. Like no, none of our software does that. So I was like after, um, there’s some twists and turns in there, but after, uh, A little while of operating MuckRack I realized like, Oh, there’s this they’re already using us for this business application and we weren’t charging them for it.

And we didn’t built build it with that use case in mind. So you thought like, Hey, we actually wants to support that use case. There’s a ton of pro tools we could build to find the right journals, like a search engine to find the journals, what they write about and what they tweet about. Uh, and then there’s this obvious test business model for it.

And I’d seen friends of mine who had started tasks companies. And I saw how powerful that was to have the recurring revenue, because it’s shorter words. I mean, it was profitable. And those first couple of years, it was great. Pat, you have a business making a profit every year, but it was so stressful to make that profit because every year I’d have to sign a big venue contract and then I’d have to sell my ass off to get the sponsorship.

And if I weren’t able to sell enough sponsorship, then I’d be on like personally liable or at least, you know, the business would be liable for which bits I took personally would be liable for all the, uh, all the costs. So it was super stressful every year, even when it made a profit. And I looked at these SAS companies, I’m like, Oh wait, you just.

No exactly how bud, how much buddy, you’re going to get that smarter. At least you can predict it, you know, within a few percentage points. And then you can feel really good about hiring people and taking on overhead because you can predict your revenue. So I’m like, okay, we have, we solve a business problem and we could have a SAS business model to solve it.

So let’s go.

Andrew: And so you started it to PR people who wanted to find reporters based on topic and have an easy way to contact them. Basically, it was like a LinkedIn for reporters. Based on topic, not company that they work for with, with an address book.

Gregory: yeah, that’s a great way to put it and to take you to in further, like the way people thought about building media lists and pitching journalists before we came along was, was like, let’s say you made a new, um, you’re doing PR for HostGator. You’ve got a new great, I, you know, great ideas, something to launch.

You’d go in and you’d be like, okay, let me just pitch every tech journalist. And the problem would be that like, well, they’re all these people that show that detector a loss, but some only write about enterprise software and they’re not going to cover your conceit. You know, you’re a small business hosting company and some of them write about gadgets and they’re never going to cover a hosting company.

So our idea was like, we had this. Rich database with everything the journalists tweeted and wrote about, and you could search for any keyword or bullying string you wanted. So you go in there and you could be like, show me all the journalists that have written about HostGator and past. Show me all the journalists writing about our competitor GoDaddy.

Uh, show me all the journalists who’ve ever mentioned the term WordPress hosting, and then you could do the super targeted pitches. So rather than pitching. 500 journalists were 490 of them are, it’s going to be irrelevant and they’re going to get pissed off at you. And Mark you is fam here. We’re going to help you find like the 10 journalists that are like, you know, writing about the hosting market.

And then you can just really customize those 10 emails and simultaneously pile them on Twitter, send them an email and really focused on making an impact and getting that journalist to pay attention to you.

Andrew: There were databases before though. You’re just saying yours was, I think yours was just cheaper than theirs, right? And more targeted by subcategory, especially around this new world of social media and tech. Am I right?

Gregory: the difference was that the people before us were static databases. So it was more like picture a directory would just be like, click on. Business and tech and then the sub category might be consumer electronics. Then you’d get a list of journalists. And they’d actually evolved out of being books. You know, like basically like phone books for journalists would get mailed out to people been around for many decades.

So we were the first to come in and be like, you know what? It’s not a directory, it’s a search engine and you can search for any keyword you want. And because of that built extremely targeted lists. So it ended up being much more about the, about the power, about just approaching it as like a search engine, as opposed to directory than it was about a price

Andrew: You also, from what I saw you started out with, I think the first product was a press release. People could submit their press release, type it into your box, right? Pay you by

Gregory: Yeah, that’s right. Yeah. So this was actually a little, a little known part of this story, uh, where before we started the SAS product, we just had this idea. My co-founder always brags that it was the, um, The best ratio of code to revenue because he wrote it. And I forget how many lines of code, like 50 lines of code or something like that.

And it made us thousands of dollars where it was called the one-line press release. And the idea was that you’d write your press release up to 130 characters. We charged a dollar per character. So it incentivized you to be there, be brief, and then it would get tweeted out from, at muck rack and then also featured on the right hand side of the site, because that would be, um, the journalists would see it there.

So that was actually, that’s a great piece of research. Uh, that was our first business model with my crack. And then we made a few grand off of that. And then it was after that, that we saw like, okay, there’s probably a bigger opportunity. We, we saw that. That was a lot of fun, but probably wouldn’t be too scalable.

So we saw that this idea of like providing people, the research tool would be a much more, um, scalable business and also lend itself better to a SAS model

Andrew: We’re also calling up your customers. You realize your customers were people who are doing PR and saying, what else do you need? Am I right? It was constantly, what else do you need in order to do your job?

Gregory: hundred percent. Yeah. In fact, I remember we even invited, um, Well, it was funny for a while. We just fill up those one-line pests releases, uh, go and never analyzed it. And I, one day I threw it into Excel and did a pivot table and count, like there was one PR agency that it paid us a couple of grand over the year, you know, over the course of a year.

And those online press releases. So I remember like we showed them actually the first prototype we had, if I remember right. We were thinking of for briefly of doubling down on the one-line press release product and creating, you know, ways to add images to it and make them them fancier. And then we had this kind of secondary idea off of it.

I think it was actually, my co-founder just was like, you know, they’re going to need to know which journalist to pitch to me, have the database. So. He coded this, this thing up really quick, that would just suggest to journalists, they signed what was in the one nine press release or a couple of keywords.

And then I remember we showed that workflow to people and it was like that last step of like, here are the journalists to feel like their eyes lit up. They’re like, Oh, you can find, how do you figure out who is journalists for like the Twitter data? So like we could tell there was a lot more excitement around finding the right journalist and there was on posting the alumni and press release or making that better.

And then that actually caused us to hone in a lot more on finding the best on that whole idea of finding the right turtles to pitch.

Andrew: I think it’s, it’s an enterprise product, right. Where I can’t just go to the site, sign up on my own. Right.

Gregory: That’s right. Yeah. It’s an enterprise product. Uh, it all goes through a sales team. It’s thousands a month and it can, or sorry, uh, thousands per year. And, uh, can scale up to the six figures depending on how big the organization is, how many users they have, et cetera.

Andrew: All right. I want to close that out with it. And I’m assuming by the way, because this business grew so much, you couldn’t focus on the podcast. You had to focus on the business. Am I right? Is that why you left it?

Gregory: Yeah, that’s what happened. You know, I love doing venture voice. Uh, it was so much fun to interview the people. You know, I really identified with the listeners and getting good feedback from the listeners was a super, super positive a cycle. But yeah, the shorter words were taken off. My crack was taken off.

We bootstrapped both the businesses. So they were a lot of work. I mean, it was, you know, for several years, two or three of us doing everything. And, you know, I was balancing the books. I was doing the sales, writing, the purchase orders, getting our, you know, making sure we have the right insurance, everything.

So yeah, it was kind of work. And I had to, uh, and there were, you know, years there is like, you know, we’d make a profit, but it was a struggle to make a profit. So, uh, I just didn’t have the, uh, the free time.

Andrew: What was the part that you weren’t prepared for having done the interviews? Having studied it business, having started a business at 14, the web design business. What’s the part that when you got to, you said, All that practice and research and prep didn’t prepare me for this. What was it?

Gregory: that’s a good question. I would say, I would say two big things, you know, one was. With radio tail. It was that struggle of knowing when to keep going, knowing when to quit, to kind of diagnose it. Is it me or is it the business? And then the other big challenge I found was just building a team, learning how to hire people and manage people, lead people, especially because that never.

Uh, outside of my experience that you’re in college, I’d never worked for a corporation. So it wasn’t like I was a manager or even had a manager as being a full-time employee. So I found that was actually one of the biggest struggles. And, uh, you know, there are a lot of good, I mean, I think I, there’s lots of good advice from my interviews and lots of good books.

I can recommend Nannette, but there’s such a large degree that when it comes to building a team, you just have to learn it the hard way.

Andrew: And

Gregory: Sorry, anyone listening hopefully to, by the, all the

Andrew: learn it?

Gregory: Chad and Eric. Yeah. It’s just bringing people on and learning how to, uh, how to manage him. Kind of getting that feedback loop of okay.

What works, what doesn’t work. I, you know, I find it’s also such a delicate thing because some of it relates to your own personality. So, you know, they’re different. There are many different kinds of leaders. I mean, that was actually one of my big takeaways from venture voice. I always thought I would discover it at like, Oh, entrepreneurs are extroverts or entrepreneurs or introverts, or, you know, this or that I found like, as I’m sure you’ve seen it on your podcasts, such a huge range of personalities, even among the most successful entrepreneurs.

Uh, so, you know, there’s that element to which you have to find the leadership style that matches your own personality. So there’s that kind of journey of self discovery along with learning to lead, that, that isn’t just a cookie cutter kind of thing. And then there’s also when it comes to managing people that you have to.

Manage different personality types differently. So maybe you figure out how to manage one person and what makes them tick, but then you get your second employee and there are different personalities. So you try to manage them the same way you manage the first person and it fails. So it takes a while to like, just have been in enough positions of leadership and had enough for reports to start to learn, you know, learn enough variety of skills to be versatile.

Andrew: All right. I thought when you were coming back. Okay. That you’re going to be lame. I’ll be honest with you. It stopped doing it for a while. I thought you were going to be lame. You came out strong and I thought, all right, he got Mark Cuban. He’s going to think he got Mark Cuban. He’s going to do a celebratory dance around it.

Blah, blah, blah. Mark Cuban is going to do the same stories. He’s told a million times. Oh, you had a really good perspective with them. You had a good rhythm with him. He was not afraid. He did repeat some stories that I heard him say before, but I fricking loved it. I remember exactly where I was running, where I heard him talk about how he bought the plane ticket that allowed him to take first class tickets as much as he wanted all over the world.

I remember saying I heard that story before it’s going to fire me up and sure enough, it got me to go up this fricking Hill. That’s right here, uh, about two and a half miles away from my house, which I freaking hate that Hill. Um, it was really good. Venture voice is a podcast. Uh, even the older stuff is worth listening to Reed.

Hastings was one of my fate. No, it was my favorite. Going back in time, Reed Hastings was by far my favorite, because you could see how he thought about his audience back then. You could see how Reed Hastings thought about creating LinkedIn and why. Reid Hoffman, who am I saying? I’ll read Hastings from Netflix.

Thank you, Reed Hoffman. He was talking about, but I even remember where I was running, where I heard that interview. I was in LA. I remember it’s so weird. How, for me, music and audio books and podcasts are linked up with where I was running or where I was listening to him. He’s analyzing. Why my space has a different audience than him, how his audience is people who are busy, busy at work, and they don’t have time to even be online.

And it’s kind of interesting for the time that unlike the MySpace audience, his people need to get in and out, it was really well done. And it’s, uh, it’s the first one that you’re bringing back and I think it’s absolutely worth listening to, and I’m looking forward to seeing what you’re doing in the future before we close it out.

Give me feedback as a podcast or what do you think of this interview? Yeah, I don’t. In fact, I don’t need the nice stuff. The nice stuff is Andrew. Congratulations. Great. Who gives a rats? What feedback that you wish was done differently or better in this interview? Go ahead. What do you think people are going to judge you now based on your analytical skills?

Gregory: that’s a tough one, you know, at this point you’re more experienced than me. So I feel like, uh, Like the novice, uh, going at it, but it was, it was fun. I, you know, I enjoyed, I mean, I enjoyed, uh, getting, getting challenged and brought back to the real year, early days, as opposed to, uh, could have held the show easily.

Just talking about scaling the later companies, you know, it’s funny with a lot of this stuff, it’s almost hard. Trying to think it was better not knowing that I got to get to these like early stories because some of those early stories I haven’t told in in years. So it takes more to dig it out of the memory banks, but maybe it’s more authentic hearing it, hearing it first drawn up from the memory banks versus probably had a chance to, uh, T to have a premeditated.

My, uh, my answers on them.

Andrew: I did kind of do a pre-interview with you on our conversation a week ago. I, I took, I take endless notes on people so that when I do interviews with them, I’ve got it. And I think that helped me a lot. There are a lot of parts here that I didn’t realize even having research do that that was going on.

That was helpful. I’m going to give myself the negative feedback since you’re too nice to do it, or maybe you’re just enjoying the conversation and you couldn’t. I find that any podcast or including myself who gets too excited or happy about a guest, lose a little bit of the edge. And I think that we don’t need to be friends with the guests, but we do need to have a little bit of a challenging edge.

Otherwise, all we’re doing is having a Bragg happy-go-lucky session with the person and a little bit of what about this? Makes for an awkward, uncomfortable feeling for the audience, but also draws the personality in a way that gives some satisfaction to the audience that they couldn’t get otherwise that they couldn’t get from your Twitter.

Couldn’t get from you sitting down and writing or talking into a mic on your own. We didn’t have that. Um, I also had, I had this experience where, because I talked to my guests during the ads, a professor. Brought my, my, my ads into his classroom. And he invited me to sit and listen, since everything’s on zoom to people analyzing.

And one of the things that I learned listening to these students analyze my ad rates is even a little bit of negativity with my, with my, uh, advertiser. I thought was there to give credibility. Look, Andrew is going to give you both sides. Even a little bit of negativity made them feel uncomfortable because they realize Andrew took money from this company.

If Andrew has anything negative, it’s like, he’s, he’s an ingrained. Like how do you take money from someone? And then you say something negative about them. And. Every time that they said something negative that I, that came out of my mouth. It was with this uncomfortable feeling about this. Like why would Andrew treat the sponsor that way?

It’s okay to treat the guests that way. But the sponsor and even me mentioning my pitch was like an infomercial. I realize I’m going a little bit too much into the negative territory around my sponsor, which I totally, I don’t think the sponsors care. They trust me, the results are there for, but I don’t want to make the audience feel like I am disrespectful of somebody that.

That they’re sitting back and seeing is a customer of mine. Because if you disrespect the customer, who’s paying you for an ad. Why not disrespect the audience who’s going to pay you for something it’s like spitting in someone’s food after they, after they served it up for you. Anyway, there’s my

Gregory: let me, let me ask you as someone who tried to do dynamic podcast ads in 2005. Why aren’t you doing them now? Or why don’t you insert them in post-production.

Andrew: Ah, okay. Um, it’s still a pain in the ass to serve up our ads. And so that’s the biggest one. The thing that I discovered also with podcast ads, it’s, if you try to play it in the, um, if you try to compete with Facebook and Google on trackable ads served up to specific people, it’s going to be, it’s going to be.

Too challenging. And you’re going to lose Spotify has a chance of doing it. And even they’re kind of challenged by it, but also you’re missing the beauty, at least at this point in podcasting of what works with podcast advertising, the understand that you have to go back to. I interviewed the founder of Uggs.

He sold these highly fashionable. All the celebrities were wearing his Uggs boots. And he loved rush Lynn by think we definitely bought an ad from Russlynn by and I said, how’d the ads go? So he says, this one woman came in, older lady comes in and asks for, I think, five different pairs of Uggs when the salesman says, why?

Cause she doesn’t seem like a typical hugs, customer rush Limbaugh said it. And so I’m going to go and buy all these eggs. Super expensive boots, not her style. She’s not the target market. She’s buying it because rush Limbaugh said it. There is. A feeling that comes from the host that, that the sponsor is asking and buying and getting.

And that I think is a special part of spot podcast advertising. So. I have to keep remembering that when I think about Jason Calacanis who’s podcasts, listen to he, it’s not, he, sometimes she reads it and I go, why is it still working for me? It’s clearly reading it. Even when the, he must have a line in his question for his, uh, sponsors, what’s your call to action.

Even read that he goes, so here is your CTA. Here’s your call to actions like he’s reading that part too. It feels to me. Why is it still working? Because the more I like him, the more I care about what he’s pitching, it’s not about the words it’s about. He could just be saying, I liked them. I liked them. I liked them.

I liked them. And that would be enough. Anyway. That’s my takeaway from podcast advertising. You thinking about bringing back radio tail?

Gregory: No, not anytime soon.

Andrew: Don’t do it.

Gregory: Yeah, but it’s, I’ve heard, it’s funny you say that that was one of the objections and challenges I saw to try and do in dynamic ads back in 2005, was that a lot of people just prefer the, uh, the host read, but I’m very, I’m very happy being in the, uh, the SAS business, but my crack, uh, and it’s keeping me more than where this year with it on its

Andrew: I would say, um, by the way, the worst example of this is the verge. The verge has ads. The verge podcast, people will talk about how 5g is just an illusion. It’s not really going to do anything. It’s not a race. It’s not this, it doesn’t do anything, anything right now. Now let’s take a word from our sponsors and they go, well, it sounds like coins dropping.

And then it’s the sponsor. The Ryzen is bringing 5g to surgery. Surgery’s now happening on five G. Like they just said, this doesn’t happen. Verizon’s pretending it happened. It’s a little bit out of sync in it. Right? I think it doesn’t, it doesn’t look good. And it’s because they dynamically insert ads and I think that’s a problem.

All right. Here’s what I always suggest to you as a podcast, or I want you to do more. I complained to you the first time, like 10 years ago, why aren’t you doing more? Most people don’t know. It takes me 10 hours. Find a way to have it take less hours. You have a fricking good team of people behind you, right?

They’re creating so much for you. You just needed to say, I need to do an interview. Somebody bought you a freaking mic. Got you. Everything you need have them do more of the work, produce more. You’re good.

Gregory: I’d be rolling out more. Podcasts plan is a one every two weeks. And who knows? They all ramp it up more. It’s good. A good encouragement.

Andrew: Good guys, keep watching and keep listening to him and keep complaining to him about why he’s not doing enough podcast. It is called venture voice. And I want to thank the two sponsors who made this interview happen. The first is top talent. If you’re hiring developers and I know no, Greg in the back of his head is now going to remember something about top talent.

I have to go back and search for it in the podcast episode in two months from now, he might come back and look for it and you might too, and here it is for you. Your call to action. Go to top And number two, if you’re looking to play around with ideas, host your ideas on a site. Not a platform that will take good care of them.

Go to Greg. Thanks so much continued success. Bye everyone.

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