Jessica Kupferman Interview Transcription

Jessica Kupferman:
I have a gift and I may have always had this; people will tell me things and then go “I can't believe I just told you that.” I either am very easy to talk to, or super nosy, or possibly both!

Harry Duran:
PODCAST JUNKIES. EPISODE 35.

This week we are with Jessica Kupferman. Jessica and I met through a mutual acquaintance, Elsie Escobar, she's the host of the Libsyn ‘The Feed' podcast, and also with Jessica, she's the co-host of ‘She Podcasts'. Now what's funny about that show is that it's a podcast targeted at women podcasters, and once I knew that Elsie was part of it, I had to listen anyway. I'm sort of like a fly on the wall for that podcast. It's not specifically targeted at me, but I get a lot of value out of the show, and the minute I heard Jessica on it, I knew I had to have her on the show as well.

She's really just a bundle of energy, she speaks her mind definitely; I guess you could call her sassy. I knew we'd hit it off because she's just irreverent and has a fantastic sense of humor. She started out selling banner advertising for businesses and she moved her way into marketing and design for some pretty big companies, including Leisure Fitness, Subaru and Bank of America. She also used to run an event magazine for car collectors, and transitioned from all of that into becoming an entrepreneur, and then she started her Lady Business podcast. After doing that for about a year and a half, she also partnered with Elsie to do the She Podcasts.

I reached out to Elsie once I heard the both of them together on the show, and she was able to make the connection for me. We spoke and had a really fun time. She's just had a child as well, so she was off the She Podcasts show for a couple of months, and Elsie was holding down the fort. Those episodes were interesting as well.

We chat about a whole bunch of things – how she got started into podcasting, how she loves to just speak her mind, and obviously she's going to have an input and a point of view about the current rash of podcasting that seems to be all about “x-preneur” and “x-OnFire”, as you'll hear. It really gets under her skin. So hopefully you'll enjoy this episode, and as always, send any feedback to www.PodcastJunkies.com Thanks guys.

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This episode is brought to you by PRDCNF, short for Productivity Conference. PRDCNF is a one-day intensive and it's the type of event that I created because I wanted to have like-minded entrepreneurs and change-makers in the room. I've gathered a fantastic group of speakers together so that they can impart some of their wisdom on you. These are folks that have had very good success in their businesses; folks like Jordan Harbinger, Natalie Sisson and Jayson Gaignard and Mike Vardy, just to name a few. The thing that makes this different in my mind, this conference, is that it's going to be more intimate than I had originally planned.

I thought it was going to be general admission, but over the past couple of weeks I felt that there was more value in getting a like-minded group of folks in the room to work off the topic of productivity, but more importantly, understand that you are the sum of the five people you associate yourself with, and in this case, given that it's such a small group of folks, it's the 50 people we're going to be associating ourselves with.

These are folks who are successful in their own right, and I've always felt that you need to have people in the room that lift you up and make you smarter. Like Jayson Gaignard likes to say, if you're the smartest person in the room, you're probably in the wrong room. We want to use productivity as a touch point, but it's not just going to be a bunch of tips; I think it's really going to be thought of as a mastermind, where we take one day, it's going to be interactive, we're going to have the speakers focusing on one topic for their talks, and then we'll take those topics as a jumping off point to dig a little deeper. There'll be a workbook involved and you'll have some solid takeaways at the end of the day, so that you really feel that you've got the most out of the day and that you've learned a lot about yourself, how to make yourself more productive, but also how to take your business and any other endeavors you're working on to the next level because you're just that much more efficient.

Being busy just for the sake of busyness is not really productivity in my mind. It's really a mind shift, and I think the folks that are going to be in this room (the speakers and the attendees) all realize the importance of getting together on this topic and every now and then, just re-setting and figuring out what you need to do to take yourself and your business to the next level. I hope you can make it; check out the website at www.PRDCNF.com, or a slightly easier to remember URL is www.DowntownProductivity.com, so you can check that out as well. If you're interested, there's an application button there where you can apply. I'm going through the applications myself – I really want to get the right group of folks in the room, so hopefully you can apply soon. Spaces are filling up but I hope to see you there. It's going to be in Downtown Los Angeles. Thanks and now onto our interview with Jessica.

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Harry Duran:
So Jessica Kupferman, thank you so much for being a guest on Podcast Junkies.

Jessica Kupferman:
Thank you so much for having me, I'm excited to be here!

Harry:
Depending on when these come out, I might have not Ladies Night, but Ladies Month, because the next couple of interviews I have coming up are all with fantastic podcasting women.

Jessica:
That's awesome!

Harry:
So that's very cool.

Jessica:
I did that for Valentine's Day last year. I had, for my show,  all guy interviews.

Harry:
Oh yeah?

Jessica:
Yeah, it was fun.

Harry:
And so you've been an entrepreneur since about 2005, if I read that correctly, and podcasting since about 2013. So I'm wondering why, with the podcasts that you were listening to at the time, that you felt there was a need to start Lady Business radio podcast?

Jessica:
To be honest with you, it was completely selfish and power-hungry reasons.

Harry:
[Laughs]

Jessica:
Like I sort of was noticing the entrepreneurial podcasts and at the time, I guess it was about passive income and Amy Porterfield had one, Entrepreneur On Fire, and Lewis Howes was just starting School of Greatness. Those were the ones that I noticed, and I sort of felt like they would never have me on. Even Amy Porterfield's guests were mostly dudes.

Harry:
Yeah.

Jessica:
I just knew so many women with interesting stories. Well first of all, I would just say that a lot of those – in fact all of those shows didn't really ask the questions that I wanted to know, which were like ‘How do you manage your day?' ‘What do you do with your kids?'

Pat Flynn is a stay-at-home Dad and his wife is a stay-at-home Mom and his kids are there all the time, but I wanted to ask them stuff about how they manage their lives. I think for women entrepreneurs, that's equally important as ‘How did you get your last 1000 followers?'

Harry:
Yeah, I think that's a good point because it's almost like they were showing the polished version, right? They were showing like this is what happens, you don't see what's happening behind the scenes when the kids are screaming.

Jessica:
Yeah, it's always the polished version. It's always the ‘How do you get successful version'. You know, not that I'm not interested in being successful, but I think that managing your life is a huge part of that. I wanted to talk to women about how they manage being successful, because I thought that maybe it would help some of us who are almost there, but can't seem to.. Is it because of fear? Is it because of lack of daycare? Is it because they're working from home and they get distracted? Is it because they can't be productive? Whatever it is, those things are equally as important as how you use Facebook.

Harry:
Yeah.

Jessica:
So that's really why I started the show, and then of course, because I felt like I wasn't going to be featured on those shows anyway, so I thought I may as well just start my own!

Harry:
Yeah, I think what you tend to see with those – at least in the beginning – is it's almost like this inner-circle, closed circle, and everyone starts incestuously interviewing each other and then you see everyone on the same show, and then you start to hear these people. It's almost like if you've heard them once, you've heard them dozens of times.

Jessica:
Dozens and dozens! Every webinar, every podcast. And it gets old! I'm super over it, and I guess most of your audience probably is too.

Harry:
Yeah, I mean I think what's happening, and I'm sure my audience at some point probably gets tired of me talking about it, but it's the whole effect of the version of the ‘x-preneur', or the version of the ‘x-on-fire', where everyone is taking the cookie-cutter approach and has said ‘Well, if this is what's hot at the moment, then this is what I'm going to use as my model for jumping on the bandwagon'.

Jessica:
You know, it's really a shame too because I've been on Entrepreneur On Fire and I have to say, the reason that works for John is truly because he's John.

Harry:
Yeah.

Jessica:
Like that approach would never work for me because I can't use the same five questions and make them sound new every time. But yet somehow when I was being interviewed by him, it felt new to me, even though I've heard the show and they're basically the same questions! But that's a skill. Maybe he was born with that skill – I don't know how he would have honed it because I know he started a show from doing something else, I guess corporate real estate. People who copy him are making a huge mistake and doing a show that isn't quite them because they want to model his success. So often in podcasting, and I'm sure you have experienced this as well, it's successful because you are yourself. You become the product. The host becomes the product and you can't be the product if you're being John.

Harry:
Yeah, there's no way you're going to replicate that, and I think it was on She Podcasts, your co-hosted show with Elsie Escobar, when you talked about that, but I think you were saying that if your show is the same as other shows then it's not amazing, and that you go out of your way to be different because that's what you do.

Jessica:
Yes. I do, but I've done that whether I was podcasting or not. I have a tendency to not buy the black leather jacket, I would prefer to wear red. You know what I mean? I'm just always, I don't know, I don't feel the need to do what everyone else is doing. Just because it makes you stand out in New York City, not wearing black, it's not good for here in Philadelphia. I don't know.
It doesn't necessarily mean that you can't be amazing, but how can it be great if it's the same as someone else's? It can't.

Harry:
Yeah, I think a lot of the time, the shows that at least I'm drawn to and I'm attracted to are the people who have personality, who have their own voice, and that's really one of the reasons why I wanted to talk to you. I had heard about your show but I didn't listen to your original podcast. Well, I actually told Elsie that I'm a fan of your podcast.

Jessica:
That's awesome.

Harry:
Because this show interviews other podcasters, so I'm always fascinated to talk to veterans who have been doing it for a while: Dave Jackson, Daniel J. Lewis, I've talked to Rae Ortega and Elsie as well. I'm just always interested in other people's perspectives on podcasting, and also people that are interesting and funny and, I guess, real, for lack of a better term. You definitely come across as that in your conversations with Elsie.

Jessica:
Thank you.

Harry:
I was catching up on, I think it was when I reached out to Elsie to reach out to you, I put in my subject line ‘Shh, don't tell anyone but I'm a fan of She Podcasts'.

Jessica:
We get that all the time! I just got one today that was like ‘Dude fan of your show'. It's like they have to call it out. I love that men listen to it, I think that's amazing, it's awesome. Actually, Harry, I just have to say that I think you're a genius for interviewing other podcasters because in my experience, they are by far the best guests. By far! If you compare a podcaster to someone who is more tech-oriented, you'll get a better show out of a podcaster any time because they love to talk and they're good.

Harry:
And they've got good equipment!

Jessica:
Right! That's a good point, the audio's always stellar, it's true. That's funny.

Harry:
Like when I started, I had a bunch on my iPod that were just folks that I listened to and I just started reaching out to those folks. I probably could have reached out to more folks and I think this is a topic that you've talked about recently as well. At some point, there's probably dozens and dozens of people that want to be on your show, and you have to decide ‘Okay, I'm just going to fill up the numbers, I want to get my one a week/two a week/three a week, whatever it is, and I just want to get volume volume volume'. I'm wondering if that's something that you went through, or that you struggled with as you started? You're close to 100 and something episodes now, right?

Jessica:
Yeah.

Harry:
And obviously there's probably varying degrees of excitement, if you'll call it that, or interest, or just engagement. I'm curious, maybe for myself as well – when you get to those numbers, are all the interviews the same for you, or are there some that stand out, and why do they stand out?

Jessica:
You know, at first it wasn't just to get content. At first I said yes to anyone who would ask because my mission and purpose was to give women entrepreneurs a voice. But then I started noticing that many of them have the same voice! And it was kind of sad, but I had to develop standards. If their voice was fresh and by that I mean like they've had their business around 3 months, they're not going to offer the same as somebody who's been seasoned and gone through some mistakes and failures and changes. Part of the way I filter now is I go based on experience, and also if they have a unique perspective or a unique skill that no-one else has. That's part of it, and then I think, well I don't even know, now I don't even know if I answered your question.

I have to filter based on whether or not it's unique and whether or not they have experience. And also whether or not I feel excited to talk to them. I have noticed that there are certain genres that aren't interesting to talk about for me anymore. I don't want to talk about holistic business anymore really.

Harry:
Okay.

Jessica:
And actually I noticed that certain guests I've had on that do dance class or exercise class, they're not good interviews. It's not because they're not interesting people, but I think it's just because they don't talk and communicate. I don't know, they're just not good at interviews.

Harry:
Do you think it has something to do with whether they, I don't know, do public speaking or do they communicate on a regular basis as part of their job – that that might have something to do with it?

Jessica:
Yeah. I think if there's no communication on a regular basis, then they're either nervous or very quiet during an interview. And then I find now that people say not that they're introverted, but that they're, I don't know, shy or that they haven't done very many. I should make more of an effort to feel people out because those who are quiet and shy are not always good interviews.

Okay, so for example, Nathalie Lussier is typically a very shy person, even though she has her own podcast and she does a video show. She was a great interview because she's not afraid to be interviewed, but I think when you test someone out, you need to know if they know how to give an answer to your question that's juicy, or do they just do the yes/no/maybe type thing. That's never good.

Harry:
Did you see in yourself that you got better with asking the question in the right way to illicit a more detailed response from people?

Jessica:
Yes. I also take a good 10-15 minutes at the beginning of the show to warm them up, but I am recording it and it's part of the show. I want the audience to sort of warm up to them and get to know them too before I get to the meat. I just sort of BS with them about the weather or if there's something going on like the SuperBowl. I don't want to say extensive, but I have a good enough questionnaire where I can pull out something interesting – like name some stuff that you're into that may or may not be business-related, and so I've learned that people are herb gardeners or ice skaters. I start asking them about that stuff and it sort of warms them up to me, and then that'll work.

If that doesn't warm them up to me, it's not going to be a good interview, I can tell pretty much within 15 minutes, and then I'll know when I do get into the meat, do I need to ask them a question flat out? Have you ever fed answers?

Harry:
Yeah.

Jessica:
So if somebody's not doing well as an interviewee, you can say “So do you find that this happens or do you find that this happens, and can you explain why?”

Harry:
Yes.

Jessica:
You know what I mean? I can give them a choice and I make them tell me more than one sentence.

Harry:
Yeah, and you really try and stay away from the yes/no questions.

Jessica:
Yeah, absolutely.

Harry:
Did you hear, maybe not the Creative Live course with the guy from StartUp, but Tim Ferriss had him on as well. I'm totally blanking.

Jessica:
Is his name Andrew something? What's that dude's name? The StartUp guy?

Harry:
Yeah.

Jessica:
Yeah, Elsie talks about him a lot. Hold on..

Harry:
I just listened to him. But yeah, he had a Creative Live course and then Tim Ferriss –

Jessica:
Alex! That's his name.

Harry:
Yeah, and Tim Ferriss had him on and he actually put half an hour of that course on there, which I thought was really fantastic. He had excerpts from his show, and he talks about how you build a story and how you build anticipation for people to be like: ‘Oh, what's next?', sort of like these cliff hangers where you want to hear, but they intersperse that with a break. They're like “After the break…” and you're like ‘Oh yeah, I want to hear what's going to happen next.'

Jessica:
Yeah.

Harry:
I was going to ask – did you know a lot about your early guests when you had them on, or was it that if they expressed an interest then you brought them on the show, and then you sort of, through the process of the interview, figured out how you were going to structure it and what sort of topics you were going to talk about?

Jessica:
My first 20 guests were friends, people that I knew really well, and I had a structure that worked sometimes and didn't work other times. When I first started, they were my friends and I wanted segments. I wanted there to be like Tech Tuesdays and then Business Thursdays, or just whatever, but I found that the show I was doing didn't always correlate with the guests.

One of the times I was interviewing with my friend, Lisa Byrne, but I also wanted to talk about a change with Twitter, and she's never on Twitter. She had zero to say about what I was talking about, and I knew that I couldn't rely on them. Even if I sent them an article, saying ‘I want to talk about this', they're still not going to have anything to say about it if they don't use it. So I ditched the segments and decided I was just going to use the time to BS, basically. I found that the feedback I was getting from listeners was that they really liked when I did that anyway, that it was so much more interesting than whatever else we were talking about, so I just kind of went with it.

I find that I have a gift and I may have always had this; people will tell me things and then go “I can't believe I just told you that.” I either am very easy to talk to, or super nosy, or possibly both! Like Andrea Owen was on my show and she was telling me about this time where she had an accident, she peed her pants or something, and she was like ‘I can't believe I just told you that on the show'. And I was like ‘I have no idea why you did, but I'm definitely publishing it, thanks!'

Harry:
Exactly.

Jessica:
That's awesome, fantastic, good for me!

Harry:
Yeah, that's podcasting gold right there!

Jessica:
Right?! She's never getting that back, ever! So I find that it just works better if I can just talk to people. I lull them into my trap like an evil spider, and then they just tell me their whole life, it's wonderful!

Harry:
It's interesting because I know when I was looking at the website or the About Jessica bit for your show, you give the overview of your entrepreneurial journey and how you started the podcast, but I love the fact that you had this extra section that talks about how you're an Apple fangirl and how you're a huge fan of the best haircare products, just random tidbits like that which are conversation starters but which also show your ability to just not take yourself too seriously and just be open about who you are.

Jessica:
I think that stuff is the most important thing. In fact, I did take a little free challenge on Facebook – I called it Facebook Foreplay.

Harry:
That's great.

Jessica:
Actually, it was hard to get an ad to stick when you call something that, just as a tip for your listeners. I find that the more off-topic I get, the better I do on Facebook. If I post about random nonsense, I get so many likes and comments, but it actually does really lead to more business.

The know, like and trust cannot be underestimated. The more people feel like they know you, the more they will think of you first. I'm a business consultant, so if I talk about the best ways of using Twitter or the best things to do on your website, they don't feel like they know me. But if I talk about how I burned dinner and got spit up on by the baby all day, they feel like they've had that day with me and then they're more likely to say ‘Oh yeah, I want to work with her because I feel like I already know her'.

Harry:
Yeah, they resonate with you.

Jessica:
Yeah. Even if they're not new Moms or old Moms, and I'm both because I have kids that are in High School and a new baby.

Harry:
Yes, congratulations by the way!

Jessica:
Yeah, thank you. So yeah, talking about him and not even like ‘Oh, I have a new baby!' – I'm not doing the whole savoring every moment, which I am. I mean, I totally am, but that's not self-revealing. It's much more revealing to say that out of all three kids, this is the one that's the most pleasant, but also the biggest mess. He is the biggest mess of any child I've had. He doesn't just spit up a little, he does full-fledged covering the room in vomit, it's awful!

Harry:
Projectile.

Jessica:
He is the worst! But he's so pleased with himself afterwards. You can't fault him for it. But anyway…

Harry:
I'm getting visions of, what is it, Amityville Horror?

Jessica:
Yes! Oh my God. Yes, and he doesn't make a messy diaper unless it's like upto his belly button, it's ridiculous.

Harry:
Thanks for those visuals, that's awesome.

Jessica:
Thank you, hey, no problem! I didn't tell you what color or anything. But anyway, yes, so that stuff I think is much more. You wouldn't think it would be more valuable than your expertise, but in a lot of ways it is. Similarly, people always say – with Facebook, they used to say ‘I don't care what you had for lunch', but people really do!

Harry:
Yeah..

Jessica:
They really do care what you had for lunch.

Harry:
Well the thing is that the people that are interested in you care, and so they're going to follow you. The minute you post stuff they're going to be like ‘Oh yeah, haha, that's funny', and the people that don't resonate with that will say that it's TMI and they'll either unfollow you or will just not provide a comment.

Jessica:
I mean, just do an experiment and ask for a meatloaf recipe and see how much engagement you get. I'm telling you, it's ridiculous.

Harry:
I may actually try to do that myself.

Jessica:
And then once you get that kind of engagement, your next post will be seen more. That's the trick.

Harry:
It's so funny because sometimes it's the stuff that you don't think about too much that has the biggest impact. And the stuff that you over-analyze and say ‘Okay, today I'm going to create the perfect post or the perfect newsletter and I'm going to make sure I triple-check this and I've got all the keywords and the hash-tags in there', or whatever it is that you need to do for that medium. And then you post it out and it's like crickets and you're like ‘Oh man', and at the end of the day you're rushing to get a post out or an email out or an update, and you put two lines there and it's all misspelled, and that's the one that gets all the attention.

Jessica:
Yeah, or the day you accidentally post a picture of a hamster in a sweater, that's the day you get the most engagement you've had.

Harry:
How do you accidentally post that, by the way?

Jessica:
Well, you know, I'm just saying. You don't want to accidentally do that, but I was thinking that on Pinterest, that's my top most-shared pin after all the episodes and all the articles and all the resources for social media and digital business – the hamster in the turtleneck, that's the one.

Harry:
So that was my follow-up question. So you do have a hamster in a sweater?

Jessica:
I do.

Harry:
What's his name?

Jessica:
I started Pinterest a long time ago, so it's an old picture now, but I just was amazed at how much engagement that got, and not the stuff you want to get, which is sort of what sparked my little science experiments about what gets the most engagement.

It's important that you BS a little about yourself because I think it really helps you in business. If that's the goal – I mean, I don't even know if your listeners give a crap about how much engagement they get on Facebook or not, but I'm just saying. Most people like to feel visible and noticed. I have friends that say ‘You always get so much on your stuff and nobody ever gives a crap about my pictures', and I was like ‘Well, I think I reveal a lot about myself, and that's why'.

Harry:
It's like ‘Wahh, woe is me' type of thing.

Jessica:
Yeah, ‘No-one loves me'.

Harry:
It's funny that you asked about who my listeners are, and I think about that as well, and I've been in some mastermind groups where we talk about that. Obviously it's folks who are interested in other podcasters, but I think right now, I'm creating the podcast that I would like to hear, and that's why I try to have the guests on that I would like to talk to, and I think over the long-term, I could probably be clearer about my “avatar”, but I think I'm trying not to overthink it. I just want to have very cool and interesting conversations with podcasters, and take it from there.

Jessica:
Yeah.

Harry:
Over the long term, and it's something you touched upon – you have another show, and that's She Podcasts with Elsie Escobar from Libsyn. She's the Community Coordinator? I always get that mixed up.

Jessica:
Yeah, Community Manager for Libsyn.

Harry:
Community Manager. So I had her on and she was a blast.

Jessica:
She's so sweet.

Harry:
When she was on, her daughter was on and her daughter kept interrupting, and I actually left most of that on.

Jessica:
It was probably with May, and May is like her nemesis when it comes to podcasting. It's hilarious!

Harry:
It was very nice. I thought it was very sweet because it just shows that it doesn't have to be a super perfectly edited show, and I got some really good feedback from folks on that.

Jessica:
Her interactions with May are my favorite because she's showing such patience. There are often times when I'm speaking with her and she always says ‘I'm sorry, I have to go wipe a butt, I'll be right back'. She's so cute about it! They're a very cute little family. It's smart that you left it in because I think she and her children are so charming.

Harry:
And so it's funny with you guys – you literally talk about anything. You guys were so happy to reconnect in the last episode, and I don't think you even cared who the heck was listening because you were just dropping curse words and ranting about your husband not stepping up. I was just laughing the whole time, I thought it was just a fly on the wall conversation. Those are my favorites.

Jessica:
Yeah. Well, I regret that now a little bit because there's been a remix about me doing that line where I said ‘When I say bounce, you bounce', but yeah, we were definitely happy to reconnect. I don't always mean to curse as much as I do necessarily, but that particular episode we were talking and it was a lady rant, I guess, and we were talking about how to podcast and get along with life, and the things that we experienced versus men, and it's true. I do feel like men with families have a choice about when they can do things and when they can't because they have the Mommy to take care of whomever so they can go do what they've got to do. I don't always feel like my time is a choice.

So it annoys me, even to be sitting and feeding the baby late at night and to have my husband go ‘I think I want some grapes, would you like anything?' I'm like ‘My hands are full, I can't eat grapes. Enjoy your life.'

Harry:
So he can sit there and feed them to you.

Jessica:
He did, actually, he fed me a few, but even that annoyed me. Just the whole thing is annoying. It's like ‘Here, why don't you have the baby and I'll eat the grapes, jerk.' And he's not a jerk, it's not his fault, but I don't know, it's just something I didn't expect to feel, I guess.

Harry:
Well I think it's great because it gives at least guys a unique perspective. I think if they don't hear these types of conversations, sometimes they're just left in the dark and they're clueless.

Jessica:
Yeah, I think so too. And he's certainly not doing anything wrong, and he's very helpful and he'll do whatever I ask. Again, it's just something I didn't expect to experience and so I guess I got a little animated. Plus, Elsie's a very good audience, so if you're funny, she kind of brings it out more because she's an appreciative audience.

Harry:
That's very funny – sometimes I make jokes and my wife groans and she's like ‘That's not funny'. But if we're with friends and I've literally got just one friend left, I'm like ‘See, it's funny, one person thinks it's funny'.

Jessica:
That's right.

Harry:
And sometimes that's all you need.

Jessica:
That's how you know if the tree falls in the forest, right? If one person laughs, then you're funny.

Harry:
Exactly.

Jessica:
That's how you know. I mean it sort of counts if you can make yourself laugh, I think.

Harry:
Yeah, that's the first test.

Jessica:
Does that count?

Harry:
How did you guys hook up? How long have you known Elsie?

Jessica:
I have known her since 2011. We took B-School together, Marie Forleo's school. And at the time it was a very very small class. I think the first B-School – she might have taken it the year before me – but so at the time, the Facebook group for B-School was like 400 people, which isn't very much. Those who were active in the group got to know each other pretty well, just in working through the kinks of setting up our business and our website and our opt-ins and our this and our that. Now it's like 12,000 people and the launch just started last week.

Harry:
Yeah, it's so funny because you know it's B-School time when you start seeing everyone trying to make it sound as natural as possible in their emails.

Jessica:
Yeah yeah. And so again, with my desire to be different, it's difficult. I just got one this morning that was so casual, I had no idea it was going to be about B-School. It was one of her friends, actually, and my friend Laura Belgray, and it had the subject line: “You used to have big ones”. She always pulls me in with the subject lines, and it was about how when you're a kid, you never had a problem pedaling your lemonade on the side of the road, and yet somehow along the way, you get fear in sales and selling and marketing, and how Marie can help you. And I was like ‘Ah, she tricked me into that! It was so good!'

Harry:
Yeah, they're going to have to get creative at some point because now literally everyone and their mother is an affiliate.

Jessica:
Put in the subject line: “B-School Pedaling. Open if interested”. I don't want to trick people into selling them B-School, especially if they're already members. I am an affiliate, but I don't like to sell it the same way everybody else does because I feel like they're getting enough of it already. I get enough of it already, and so I just kind of want to say “Hey, I took it and it was really good for me”. I don't know if it's going to be the same experience for you, but if you're interested, I'll help you.

Harry:
Good for Marie, right?

Jessica:
Yeah, it's great for Marie, although this year she got really selective about who was going to be able to sell it, which was probably smart.

Harry:
Yeah. that's probably a good idea because at some point, I guess she provides collateral and they start to butcher that, I'm sure, at some point.

Jessica:
Exactly, yes.

Harry:
So when you started up She Podcasts, was it just a function of finding someone that you really resonated with and that you got along with and you said “Hey, we should do a show together”, or were you trying to meet a certain need? Or were you just tired of podcasting by yourself?

Jessica:
None, actually. I actually started the group – I had no intention of doing a show whatsoever. It was after New Media Expo and I felt like I had gotten to hang out with a bunch of women podcasters and it was so much fun to just have dinner with like six other women in podcasting and commiserate about the stuff we go through and help each other with marketing and what kind of scheduling pieces we use, and what guests we've already had. It was great, and so I was like ‘You know what, I want to have a little group', and it was just like the six people that were at NMX with me, and Elsie was there as well. And then she was like ‘Oh, this is such a good idea, can I invite some other people?'

So then I opened the group up and I said ‘If you know any women podcasters, please invite them because I really feel like we can all help and support each other'. And then Elsie kind of messaged me separately and said ‘I'm so glad you started this group and it's so helpful and I really want to help with it'. I was like ‘Sure' and so I made her an admin. Then maybe a week or so later she was like ‘You know, I've been thinking about doing a show, but I had this idea for what it was going to be called'. At the time it was just like ‘Women Podcasters' as the name of the group, and she was like ‘Oh, I want to do a show called ‘She Podcasts'.'

I was like ‘Oh, such a good idea'. And she was like ‘Well, do you want to do the show with me?' So I said sure, and then I changed the name of the group. So the show actually came after the group, and her idea was to do the show. It was weird because the community started first, and then she sort of married her idea for a show with it, and then it all just kind of clicked and worked together. Now I think I add like 10 women a day, at this time.

Harry:
What is the total up to?

Jessica:
I think it's 1200 but let me take a look.

Harry:
Woah!

Jessica:
I know! It's like 100 a month, it's incredible, isn't it? Let me look. I'm going to the group right now. 1,176 members, and yet right now, and I just did this last night, I have 8 requests, and it's 1.30 here.

Harry:
And are you getting them from all over the world?

Jessica:
I get them, yeah, from all over. Here's one – Celeste is a writer for Huffington Post. Hello Celeste, welcome! I usually go by if they have mutual friends or if I can see what they do for a living. Sometimes we do get spam requests, and then I have to say no to those.

Harry:
I'm going to call out Celeste when I post this show. I'm going to be like ‘We called you out at minute whatever'.

Jessica:
Yeah!

Harry:
I'd love to hear that.

Jessica:
Yeah. So 8 requests, can you believe that? I do it every night and usually I check in the morning because I don't want anyone to have to wait too long, and Elsie's busy so I try to at least do the maintenance stuff in the group so she doesn't have to deal with it. She writes crazy awesome show notes so I feel like it's only fair.

Harry:
Yeah, you were telling her how bad you feel about that I think on the last episode.

Jessica:
Oh my God, I can barely live with the guilt!

Harry:
So it sounds like you've filled a vacuum, right? I don't know if there's a lot of other shows that are covering this topic, or obviously not with your format.

Jessica:
I don't think there's any, are there?

Harry:
Well not that I know of. I can only follow one female podcasting show at a time.

Jessica:
Without losing some of your masculinity you mean?

Harry:
Yeah, maybe it's something like that, but you guys are hilarious so that's why I don't have a problem.

Jessica:
You know, somebody tweeted me once like ‘Oh, I'd love to listen to your show but it's She Podcasts', and I was sort of like ‘Umm.. Yeah, but we're not talking about like menstruation. Feel free to listen!'

Harry:
Someone sent me a link one time and was like ‘Oh, my girlfriends are trying to podcast' – because every time you tell someone that you podcast that doesn't podcast, they mention the one podcast they know. And she happened to have these girlfriends that started one, and I listened, and it was literally like two girls podcasting on like 100% female topics. I was like ‘Okay, I gave it a shot, but I'm definitely not the target audience for this one', but it was hilarious.

Jessica:
And yet still you were okay with listening to me rant about my unfair and uneven marriage once I'd had a baby. That's interesting.

Harry:
Well because you mixed it in with the podcasting tips.

Jessica:
Yeah, I guess we were sneaky like that for you, Harry.

Harry:
No, but at the end of the day, right, think about the shows you listen to – obviously if you still have time to listen to podcasts.

Jessica:
Yeah, it's true. If you ever have a baby, now you'll know what to be sensitive about, I guess.

Harry:
Oh, I definitely will, believe me!

Jessica:
To be helpful and not to let the other person do all the work, right?

Harry:
I'll think in my mind – what would Jessica do?

Jessica:
That's right. What would I say? Would she call me a ‘b' word, and if so, I won't do that!

Harry:
You can curse on this show, don't worry about it.

Jessica:
Yeah, and I wouldn't want to listen to all men, even if it wasn't about sports. What are male topics? I don't even know what that is. Like male bonding and shaving? What would I care about that for?

Harry:
Some of them, I'm sure, get pretty raunchy.

Jessica:
Yeah, right! Or God forbid that I find out something about men that I never wanted to know, like how they really think.

Harry:
Right. I'm sure there's podcasts like that. Because I see some of these and I follow a lot of podcasters on Twitter, and then I look at the topics or I look at the cover art and I'm like ‘Woah, this is like bordering on soft porn over here'.

Jessica:
Oh my!

Harry:
No, just raunchiness. Like they're talking about just stupid topics, and it's just like toilet humor. I'm like ‘Wow, man', but they've got all these followers and there's an audience for everyone, I guess.

Jessica:
There is an audience for everyone. I bet you find a lot of that in the Comedy section, I'm guessing. Because what's funnier than toilet humor? Nothing.

Harry:
Well, that's a point. You outgrow that, right?

Jessica:
No, apparently you don't. I really don't. I think people like to pretend like they outgrow it, but they don't.

Harry:
So how are you feeling about your show? I always wonder and I'm fascinated by people that are in the 100s and 200s and like Dave Jackson with 400. Does it ever get tired and do you feel like you want to move on?

Jessica:
Yeah, I've been talking about this a lot, especially with Elsie and especially on She Podcasts. We did talk about pod fading and I've sort of started considering it, but only because it's really hard, Harry. I am starting to feel like it's possible that I've spoken to and interviewed everyone, with the exception of maybe 10, I might want to talk to. Like ever. But at the same time, then something happens. Like yesterday my husband got a Facebook message from a High School friend that said ‘Oh my God, I had no idea your wife is Lady Business Radio, I listen to it the whole way from driving from here to Chicago. She's brilliant, she's funny'.

And then I'm like ‘Well, dang, maybe I really shouldn't stop doing it'. I started getting to a point where I couldn't interview anymore because as my pregnancy was progressing I was kind of getting dumber and dumber and unable to focus on other people, so I started doing the Jess Files, which was just me talking. And it's shorter, it's like 20 minutes. I can keep my own attention for like 20 minutes, and I've been enjoying that more, so I'm wondering if I should just change Lady Business Radio, or the Jess Files, and then pepper it in with interviews as someone interesting pops up for me? I don't know. I just don't know what to do about it.

Maybe it's just that I've not done an interview since like September/October and I feel sort of lazy about starting it up again. It's an hour show, and I don't know that I can switch it to a half hour without getting to the juicy, random things that are good.

Harry:
I'm of the opinion that at the end of the day, whatever decision you make about your show, is perfectly fine because it's your show. People talk about this responsibility we have to our listeners, but a lot of the time I'm just like ‘Look, it's my show, I'm going to try this out and if you don't like it, then I guess you won't be listening anymore, and if you do, then I guess you'll keep listening'.

Jessica:
Yeah, I don't feel responsible.

Harry:
There's both camps, right?

Jessica:
I guess I'd feel like if people really like it, it's a shame for me not to do it anymore, and then on the other hand, I feel like if I don't like it, it is a shame for me to keep doing it.

Harry:
But maybe it's a function of trying to find, or holding out for just really truly special guests. So when you do have them on, it's someone that everyone is looking forward to that conversation and they're going to say ‘Wow, I can't wait to see Jess and this person talk'.

Jessica:
Yeah. When you get feedback from your show, Harry, are people usually commenting on the guest or are they usually commenting on you?

Harry:
I think they're commenting on the conversation. Like: “That was a good conversation”, “I really enjoyed how it was laid back and how you guys were just shooting the shit”, and that sort of stuff. I just had Jordan Harbinger on and I don't know that they necessarily say things like “I'm glad you had” – well, it just came out so I haven't had too much feedback on it yet, but I don't know that people would be like “That one tip he gave was so so valuable”, because he's been on so many shows so it's almost like what do you bring? What's the combination of me and my guest together? What's that alchemy that results? At the end of the day, that is, I would imagine, why people listen to a specific show.

Jessica:
See, and that's the thing. Sometimes I get what you're saying. Sometimes I hear “That was such a good conversation”. Sometimes I get, and it depends on the guest, people will say “I really loved her, I'm glad you had her on.” But the majority of feedback I get is “I love listening to you, you're hilarious”. And that makes me feel like maybe I don't need the guests all the time, I can just rant the way that I do, and then people would still like it and I wouldn't have to do a different show. You know what I mean?

Harry:
Yeah. Have you polled your listeners yet?

Jessica:
No, I'm scared! I don't know when this is coming out, so by then I may have already made a decision, but I'm scared to poll them.

Harry:
Yeah, I think you've just got to ask them, and then if you've got a Facebook group for the show, just say “Hey, I'm going to stop the show, what do you think?”, just maybe make it that dramatic and see if people automatically all jump in and just say “No no no no, don't”.

Jessica:
Yeah, one time I polled them about whether or not I should split the show into two half-hour show, and there was like a revolt. And I didn't understand what the big deal would be about hitting ‘Next', but whatever.

Harry:
A lot of people I see that do two-parter shows, and a lot of people used to talk about it increasing your download numbers.

Jessica:
Yeah, John recommended that I do it! So I asked them what they thought about it, and they were like ‘No, we'll never listen to you again', and I was like ‘Alright, fine'.

Harry:
Nowadays you just pause if the show's too long. You just pause and you pick it back up again.

Jessica:
Right! I don't see what the big deal is.

Harry:
I don't understand these multi-part shows.

Jessica:
Strong feelings, very strong feelings. So yeah, that's why I'm a little afraid to ask. I'm afraid, as a people-pleaser, I'll be super compelled to do what they say and not what I want.

Harry:
Yeah, you can't do that.

Jessica:
Right, so that's why I kind of don't want to ask. So anyway, so yes. You're asking me at a time where I'm super torn about what I want to do because I don't necessarily want to pod-feed, but that doesn't mean I can keep up 8 interviews a month either. I don't think I can do that, so I'm in the process of coming up with some type of happy medium that works for me, I guess.

Harry:
Yeah, for me I thought at some point I would just have someone help me get interviews as much as possible so I could fill up the show, but then I thought ‘I don't want to talk to someone who I don't know, I don't resonate with, who I haven't heard before, just because they're a podcaster'. Obviously nowadays, there's thousands of podcasters, so I would probably never run out of people to talk to, but I want it to be an interesting conversation. I'm sort of holding out for meeting people or getting connected to people like you, where I've heard them and I just know it's going to be a fun conversation, even though we've never had a conversation before on Skype. I get a feel for people sometimes, is what I'm saying.

Jessica:
Yeah, of course. And you can take that person. If you really resonate with Elsie, she could probably recommend like 800 people that would be awesome.

Harry:
Yeah, totally.

Jessica:
Because she's awesome and she probably gravitates towards more awesome people.

Harry:
As I'm sure you do as well.

Jessica:
Yeah. I mean I certainly know a lot of podcasters, of course, that I think would be good. I'm curious: do you only interview people who – and I guess this shows my knowledge of your show – but I don't know if you only interview people that have podcasts on iTunes, or do you count it if they have a Google show? Do you count if they have a YouTube show? I get it where people think it's not a podcast if you can't listen on an iPod, right?

Harry:
Yeah, I think it would have to be on iTunes to be considered a podcast, because if it's just on YouTube, then they're a YouTuber, I guess, right?

Jessica:
Yeah, right. Then they're a YouTuber, not a podcaster. So you go based on iTunes. So yeah, I know someone who has an amazing show, but I think it's just a Google show, I don't know if it's on iTunes.

Harry:
They do just HangOuts?

Jessica:
Yeah, they're just HangOuts, but she's amazing.

Harry:
Actually no, it doesn't technically have to be on iTunes because there are people who now host it on SoundCloud and they're trying out different hosting options. I guess at the end of the day, if there's an RSS feed and you can pull it through any sort of Podcatcher, I guess that would qualify.

Jessica:
But technically, if you look up the term podcast, it's meant to be an Apple piece played on an Apple product, right? If you have to be all crazy technical. So that's why I was asking what you so far have stuck to.

Harry:
Was that your inner Rob Walsh?

Jessica:
Did I sound like Rob Walsh?

Harry:
[Laughs]. No, because I've heard him and Elsie, and he loves to get super technical about what exactly a podcast is.

Jessica:
He does! I really like that about him. Yeah, he does. He's very technical and serious. He's a serious dude.

Harry:
I'm having fun with this conversation, so maybe we'll pick it up at another point. What insights do you think you've learned with the show that you have? Or any surprises that you had when you first started podcasting? What did you think the show would turn out to be like, and 100+ episodes, bordering on 200 episodes in, what do you think you've learned over the course of the 2+ years that you've been doing it?

Jessica:
You know, the one thing that I've learned over both shows consistently is that you have no control over your audience, their likes and their dislikes. You can gear your show to someone, but that does not mean that that person is going to listen or care. Ever.

For example, when I started Lady Business Radio, I wanted it to be live. I wanted the guests to take calls live, but I didn't want it to be a webinar. I thought ‘No-one has a live podcast, I'm a genius, I'm going to do the first live podcast'. But yet, the truth is that people like podcasts because they're on demand, not because they're live. So I was getting super irritated when I would get 10 people or like 5 people on a call and I would get so annoyed, but then I realized that that show got 200 downloads like 3 days later.

So I was like ‘Oh, they want to listen, just not when I say so'. So I just kind of let go of that live aspect of it, and the same with She Podcasts. Often, the people who are sending us feedback are men. Women do too, but I would say at this point, it might be even. That doesn't mean that we have an even audience, but I know that the vocal audience might be even – the people who are willing to tell us something. Actually, we had one person who was relatively well-known say ‘It's a shame that I can't participate in the conversation because I'm a dude'.

Harry:
Maybe you need to have Dude Week or something like that.

Jessica:
But I can't let guys in the group.

Harry:
Oh no, no, of course.

Jessica:
That's the thing. And so therefore there's no way to really engage in the discussion. That's true, we don't have discussions anywhere else except Facebook, and that's a women-only group. So it's hard.

Harry:
And I'm sure some women would probably not want it.

Jessica:
They don't.

Harry:
Dudes have plenty of podcasts; they've got plenty of forums for them to talk about their shit.

Jessica:
That's right.

Harry:
This is something that's specifically for you, and they're not going to want some dude to come in and spoil it.

Jessica:
They don't, because men can be very technical and a little condescending about tech, and that's why it needs to stay women only – so they feel safe and not stupid asking basic questions about how to do this or that.

Harry:
I think as much as I'd enjoy coming on the podcast and talking to you guys, I definitely think we have to give you guys your space and let you do what you do, which is cool.

Jessica:
Not even that you would do that, or that these guys would do it, it's just that women just feel like when there are men in the group, they're less likely to ask basic questions, and they need to know the answers. I don't want to make those shy women feel uncomfortable.

Anyway, back to your question – I can't control that guys are listening or not listening. I don't want to stop them from listening. You know what I mean? We didn't gear the show towards guys, and yet they listen anyway, and we have no control over that. If we were to do, for example, a live event and an even amount of each would want to come. Elsie and I have no control over that. And similarly, you and I maybe are geared more towards the business podcaster, but I don't know if She Podcasts is or not. I know Elsie is not anti-, but she's not really interested in catering to people who are podcasting for their business. She also likes entertainment podcasts and tech podcasts and comedy podcasts. I think if she and I could control the show, it would go in two totally different directions and have two totally different audiences, and we've never polled them to find out. We've never said: Are you more of a business podcaster, are you more of a non-business podcaster?

Harry:
I think the fact that they're just podcasters period is what keeps it interesting.

Jessica:
True, but for example, we were asked to do a seminar together and that'll come more into fruition soon, and I was just like ‘We should teach people how to get sponsorships and advertising and do it for money', and Elsie's like ‘But what if people are just doing it for the fun of it?' That wouldn't even occur to me! Do you know what I mean?

Oh, people podcast for fun?! Well, then maybe we should teach them something else? But neither she or I really have any say in what they're doing. We just have to find out, sort of. And the same with Lady Business Radio. If they're all stay at home Moms, that doesn't mean I targeted them at all.

Harry:
That's true, that's true.

Jessica:
But it's the one aspect of media that you can't really control. I don't know, I just feel like with your blog and your business, you can have a target audience that you are in control of, but with podcasting, I don't feel like that's true. You don't know who's going to like it or not like it or why.

Harry:
We're at a really interesting time and so we sit here in February of 2015, and podcasting is on everyone's lips right now, courtesy of StartUp and Serial.

Jessica:
Yup, I know.

Harry:
So what has got you excited? What do you think the biggest opportunities are in the coming year?

Jessica:
To be honest, I really feel like, and I'm hoping, that it just means more eyeballs. I don't want to hope and wish for more than that, because I just don't want to get my hopes up. I will say that there are so many people who have started out on YouTube and become like these international sensations, and you very rarely, if ever, hear of a podcaster who's done that.

Harry:
Yeah.

Jessica:
Like, Serial's probably the first one. People who are successful on podcasts usually are so because they've had success elsewhere – Aisha Tyler, Adam Carolla. They're all famous people elsewhere. Nobody starts a podcast and then all of a sudden is an international sensation. Even Sarah Koenig is NPR. You don't become a famous person just from podcasting necessarily. I would like to see the first – I'm not saying BE the first, although hey! that'd be amazing! – but I'd like to see the first people start a podcast and then move that to a television show, or move that to a Howard Stern type deal, or move that to something bigger and exciting that does warrant a significant amount of advertising.

I get advertisers, but they're not based on downloads. They're based on reach. In a lot of courses, including Podcasters' Paradise, there's this mathematical equation that like 1,000 downloads = $15 in advertising, but a lot of women's shows will never get 1,000 downloads an episode. It's very hard to do that when you have an all-women audience. But that doesn't mean I'm only charging $10. Forget, that, I charge $250. You know what I mean?

Harry:
Yeah, it makes sense.

Jessica:
So I guess I'd like to see a different advertising model for people that have different audiences, that aren't business-based, that are more of a bigger reach. I'd like to even try different types of podcasts and see if I can hit with one that isn't business-oriented. I have a couple of other ideas for shows that are more entertainment or where we can do one like Ricky Gervais where it has seasons. His show had like Season 1, Season 2, Season 3.

Harry:
Yeah, I've seen a lot of people do that.

Jessica:
And I really want to try that and see if I can get one that's popular or well-liked with that format, so that pod-fading isn't.. You know, you just have four seasons and you're done.

Harry:
Yeah, and then it's evergreen content.

Jessica:
Yeah. Like on Netflix, or whatever.

Harry:
So wait, you're a podcaster and you actually have ideas for new podcasts? No way!

Jessica:
I know, can you believe it? I never stop having ideas for podcasts, it's just a matter of what you have time to do and if you get sick of yourself, right?

Harry:
Hear, hear.

Jessica:
Right? Don't you have ideas for other shows too?

Harry:
I do.

Jessica:
How many other ones?

Harry:
Uh, probably at least 2 others. I started out with one originally that I didn't do, and I ended up doing this one.

Jessica:
Well, will you tell me the idea for the first one?

Harry:
Yeah, I had a mobile app for electronic music because I'm a DJ, and I wanted to interview other DJs.

Jessica:
And why didn't you do it?

Harry:
I felt it was going to be hard to get in contact with the types of DJs that I wanted to, and then I just went to New Media Expo in January of 2014 and I saw all the entrepreneurs there and I thought I actually like some of these podcasts, so why don't I talk to some of these people first?

Jessica:
Yeah, because that idea's not going away.

Harry:
[Laughs]. No, not at all.

Jessica:
And maybe in doing this one, you'll find easier ways of doing that one.

Harry:
Yeah. And it just makes me aim for bigger guests on the podcasting scene. Obviously I would love to interview Joe Rogan, I would love to interview Sarah Koenig, you know, so they're now on the list.

Jessica:
Yeah. Joe Rogan probably wouldn't be hard to find!

Harry:
Yeah, I must get on that.

Jessica:
Yeah, why not. Go for it.

Harry:
I am, let's put it out there. So Jessica, thanks so much for your time.

Jessica:
Thank you so much, it's been amazing.

Harry:
Time flew by, right?

Jessica:
It did!

Harry:
So I saw that you're also a candy connoisseur; is Willy Wonka one of your favorite movies?

Jessica:
Uh, the old one.

Harry:
Yes, of course the old one.

Jessica:
Johnny Depp is a little creepy in that new one.

Harry:
No, I didn't even watch the new one. But the old one I never get tired of.

Jessica:
Yeah. The new one is like the stuff nightmares are made of. But I love Gene Wilder, yes. I do love Willy Wonka, absolutely, and all his candies as a matter of fact.

Harry:
Yeah, never get tired of that. So where can people find out more about Jess and what she's up to?

Jessica:
So my website is www.LadyBusiness.biz, and then if you are a female podcaster, there is a group and a website: www.ShePodcasts.com and then the group is just www.ShePodcasts.com/group, and it goes right to Facebook.

Harry:
OKay, that's perfect.

Jessica:
And thank you so much, really, it's been so fun talking to you!