FTW Wednesday: Jessica Kupferman on Podcasting your way to never selling again

FTW Wednesday: Jessica Kupferman on Podcasting your way to never selling again

We had to change the name. Winning Wednesday was lovely, but Spam filters apparently dislike the word ‘winning’ – so roughly half of you missed our very first feature last week and have no idea what I’m talking about.

Last week, Makeness began publishing a brand new weekly feature called ‘Winning Wednesdays’ [now FTW or ‘For The Win’ Wednesdays] where we feature an in-depth interview with an entrepreneur who deserves a whole bunch of gold stars for doing one single thing really, really right. They are, of course doing other things right too, but this series will tell the whole story of how they got really, really good at just one facet of their business.

Today, I’m delighted to feature Jessica Kupferman of Lady Business.Biz and Lady Business Radio. Podcasting is totally not my area [and I am admittedly wary of anything popular… just owning my bias here], so I’m gonna let Jessica take it away. My comments are in italics below….


Makeness: So, What is the ONE thing you know that you have nailed in your business? Be specific.

Podcasting, baby! My show gets about 1000 downloads per week and I’ve interviewed over 110 women (and some lucky men.) The greatest thing I ever saw was my year-over-year website statistics – I quadrupled my web traffic since starting my show!

[I’m totally paying attention now – in spite of my irrational need to not do anything other people are doing.]


Makeness: Tell us about all the things you tried that relate to this that DIDN’T work?

I had a video show called JKTV for a hot minute. I really wanted a vehicle for business that was SUPER entertaining. But video has some drawbacks for me. First, I hate that in order to LOOK like I’m looking at someone, I had to look into the camera instead. So annoying. Also, I was very distracted by the way I looked – I fidgeted a lot and was sort of obsessed with my hair misbehaving. Lastly, I was a SUPER perfectionist about the editing – like a sick OCD person. So the audio thing was obviously way better for me.

[I love that part of what lead you to this was accepting that you weren’t great at something else – and you had the lady-balls to admit that it didn’t work for you. Quitting is rally hard for a lot of people – but it can lead you to so many more valuable (and right-for-you) things.]

Makeness: What was the catalyst for getting your thing to work really, really well?

I think a combination of things: the name, the guests, the format is very casual and I try to make sure it’s FUN and not a sales vehicle.

You know, I also have to say I’m blessed with some type of ability to get people to open up to me. I’m not even sure I’m a good listener, so I think it’s more about making people feel that no matter what, I’m not going to judge them. I also am a HUGE observer of human behavior – so I often know who will be a good guest before I’ve even spoken to them. Those things together I think make a good talk show host. Trust. Honesty. People know they can trust me and that I’m looking for real truth, not fluff. And it takes persistence and talent to get both of those.

I think if you love and are fascinated by people – and you love the subject matter and you love the idea of having your own show, as I always have, podcasting is the perfect medium.

[Choosing your medium for your message is about so much more than what you *think* will bring the dollars rolling in. You HAVE to really look at your unique cocktail of skills and passions before you decide how to get your work across. So often we disregard things like being easy to talk to or being cool under fire as business skills, but there are so, SO many ways in which you can apply these things, you just have to find the right outlet.]

Makeness: How do you know it’s working?

I know it’s working because people I’ve never even met before tweet me and message me all the time to tell me how much they like it. Also I started a Facebook group for listeners and guests and two months later it’s hopping in there! Very active group and people are very passionate about supporting one another.

I like to use this term: hot leads, served fresh daily. People listen to my show and they write me and are already ready to hire me. No sales convos required. I’ve never before experienced that in my business. I’ve had my own business for 10 years and never once have people just called me up and said, “I know you’re the one who can help me. Where do I pay?” It’s because of the podcast that they feel they know me, they trust me, they like me. So the daily hustle has changed from “who can be my next client” to “how do I get more listeners” because the leads are already coming in.


Makeness: What influenced the direction you took ‘the thing’?

Really it was me.

I have very specific goals that I want to achieve with it. I didn’t know when it started that I’d want to teach others how to podcast but I should have – I often learn something and then want to teach it. But mostly I wanted to create a fun community of truth telling, sassy women who make their own rules and the next step is to travel to meet them in person by creating live events!

[OOOooo, I love the next-step thinking. Real business requires thinking about the step after the step after the step. Podcasting works for Jessica because it’s a natural lead-in to her next thing, and the teaching part is a natural fit to keep it interesting NOW. But I see SO many people starting a podcast just because it seems like this magic traffic-builder. They aren’t thinking about what comes after episode 150… when the boredom, or complacency, or good old-fashioned laziness sets in. Do you know what you want to do AFTER that?]

Makeness:What advice would you give to others who feel like their ‘thing’ isn’t working?

Honestly, I think if it’s not working, it’s not really your “thing.” It took me YEARS of searching and personality tests and experimenting to find my thing. I’m almost 40. It’s a hard thing to do. I would say really, REALLY dig deep and know yourself and what you like – don’t count out ANY part of yourself. There’s a way to incorporate your funny, irreverant side or your nerdy side or your fashionable side. You may just not see it yet. But it has to be ALL parts of you – nothing hidden.

[!!!!!!! – Read that last bit again. Because truer words were never uttered.]

Makeness: Anything else you think people should know about you or your business [as it relates to this topic]?

I’m not someone who is really married to anything working out.

If it didn’t work, I’d do something else.

You have to try stuff and see what kinds of creative disasters you can create. Don’t be afraid of that. A podcast isn’t for everyone – it’s for people with amazing things to say and nowhere else to say them. This is for you – the underappreciated and the overly brilliant. I created my own media channel because I was tired of wishing other people would feature me. Now I feature me and whomever else I want. I like to try new things and see if they blow up in my face. Try it!

[I love that this leap was about full-on risk. Being willing to fall flat is roughly the single most valuable skill any entrepreneur has in their arsenal. And putting yourself out there with your very own voice is a fierce expression of that.]

Makeness: Any final thoughts?

Once you find your thang, you’ll know. People notice. People you admire reach out and tell you. Others try to copy you. Strangers thank you. If it’s not there yet, but you’re almost there, keep at it!

Podcasting is a huge commitment – it’s not like blogging where you’re not sure people will notice if you write or don’t write that week. You have listeners, and they are waiting for content. If there’s even one tiny audio glitch, they write you. And to me, if you’re going to do something, it has to be good. I’m committed to:

1. having an interesting show

2. having good sound quality


3. delivering without fail every week.

It works for me because it offers consistency for me in my OWN business – no matter what crisis is going on, that show goes live on Wednesdays and Fridays and my email goes out once a week. That consistency has offered me a schedule to work around – a beacon of light with which to see each week. So if you don’t have room for that commitment, perhaps it’s not a good thing to start – and if you WANT something like that, something you’re married to, and you want your voice out there, and you want new audience and new clients and instant authority – then sign up, baby!

Makeness: What are you currently promoting in your business?

Podcasting School for Women [not an affiliate link – I just like Jess’ jam], the only online course that focuses on helping busy women create a podcast that’s FUN, technically easy, and doesn’t suck all your time. Check it out!

Makeness: How would you like readers to reach out to you?

Ladybusiness.biz or my Facebook group, ladybusiness.biz/bombsquad


Are you TOTALLY WINNING at something? Tell us all about it and see your very own story here.


Please note: I have turned off comments on the blog because I have found that we have far more lively conversation inside the Makeness Insider Community on Facebook. If you would like to join us there, consider this your cordial invitation.

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