Ep. 87 | Courses Are Dead. Here's How to Get More Clients Instead, with Jess Webber
49m 23s
Jess Weber specializes in helping entrepreneurs and coaches simplify their complex ideas and intellectual property into clear, actionable, and emotionally engaging frameworks. Through her "big ideas made simple" approach, she guides clients to define their vision, organize their assets, and create structured pathways from where they are to where they want to be. Central to her work is the design of short, high-impact challenges—typically three days long—that deliver specific outcomes through storytelling, emotional journeys, and micro-wins. These challenges build trust by focusing on transformation, not just content, and include a VIP upsell that offers proximity and feedback, not sales. Jess emphasizes that such challenges are more effective than traditional webinars, courses, or PDFs because they align with modern consumer needs for authentic, human-led experiences. The model is scalable, repeatable, and designed to serve as a “first chapter” of a larger offering, effectively introducing new clients to a business while nurturing trust and loyalty. Her method combines emotional intelligence, strategic structure, and proven results, making it a powerful tool for coaches, consultants, and creators seeking to grow their businesses through meaningful connection.
Welcome to From Click to Client,
where we transform a confusing message
into a clear, compelling story that sells.
I'm your host, Chris Jones, story brand marketing expert.
I'm here to help you attract more dream clients
with the power of story.
Jess Weber, I am so delighted to have you here on the show.
I've been really looking forward to this.
For those of you who don't know about Jess,
you really should, and you're going to get to know her today,
I am a big believer in coaching,
because we are all inside our own dam bottle,
trying to read the label that can only be read from outside.
And I don't care who you are, or what business you own,
you are stuck in your own bottle.
And the only way to really read that label is to get coaching.
So I coach my clients all the time.
But I also have coaches.
And Jess is one of my coaches.
Jess and Adam Roach, the two of them work together.
So I've been working with Jess pretty consistently,
and it has been so number one fun.
Number two, it's been so eye-opening.
Jess has a lot of different superpowers,
and I'm going to let her explain them to you.
But before I do that, I will say that Jess
is masterful at looking at someone's IP
and organizing it in a way that makes perfect sense.
And that's one of the big things that she does for her clients.
She has a podcast called "Big Ideas Made Simple."
Is that right?
Yeah, and I think that really encompasses what she does.
She'll take your big ideas and simplify them
in a way that they can actually be digested.
And that's really fun for the person learning about your IP
to go through it in a way that feels really good
and not overwhelming.
So Jess, welcome to the show.
Thank you so much.
And for such a kind introduction, I'm excited to be here as well.
You're one of my favorite people that I've met through this coaching endeavor.
And I just-- I have so much fun talking to you.
So any day with Chris is a good day in my book.
We do have a good time.
So we have an hour long call once a month.
And we always like to allow another hour just for yap
and a little cushion on the other end of that.
So Jess, I'm really happy to have you here.
And I would love to hear in your words,
like, how do you describe what you do and the problem
that you solve for your clients?
I love that you ask this because it's
something that's constantly evolving
as I spend more time explaining it to people
and figuring out what language resonates.
But I landed on the language of big ideas
made simple because it was the shortest, simplest,
clearest thing that I could say that kind of was a nice umbrella
for everything that I've found myself dabbling in.
Because I am a multi-passionate, multifaceted human
that has different interests and loves
and entrepreneurial endeavors.
And it was like, how do I encompass all of this?
And so I built big ideas made simple as a coaching, consulting,
speaking, podcasting, container to help people
create a clear path through information to an outcome.
And so I've taken my background in all of my experience
first in education where I did have a master's
in curriculum and instruction.
And then my years in franchises and real estate operations
where I ran a billion dollar brokerage
and managed 500 agents.
And I'm kind of married all of that into this new thing
of helping people really figure out what is their vision,
what is their end goal, what do they currently have,
and bridging that gap between the two.
And so you mentioned my business partner, Adam.
When I first met him, he gave me the label of an architect.
And I said, oh, that's a fun way to describe what I do.
Because I sit here and I'm like, hey,
what is the big thing that you want done?
So Chris, what do you want for your business?
Great, what are the parts and pieces
that you currently have now?
Is there anybody else in your world?
Okay, let's write the plan, the strategy.
Let's architect the framework you need
to get from where you are to where you want to be.
And so I just, I love doing that.
And like you said, super power all the way.
Totally, you do.
You really make the path clear both for your clients,
but really for the people consuming that information.
Yeah, it's been really interesting
because I've worked with a lot of clients
in different industries.
And most people think, oh, if you haven't been
in that industry, how can you help?
And I think that is where my skill set comes in
because I can consume vast quantities of information
and quickly understand, does it relate
to the defined outcome or not and have that filter
where somebody who's stuck inside the jar
is drowning in their own IP, right?
They've got so much intellectual property
and so many assets that they don't know how
to see the force through the trees.
And so I can come in and say, okay,
if you say this is the outcome,
I can look at this and say, does it match or does it not?
And anything that matches can go into that framework
and anything that doesn't can become a bonus asset
because I'm not saying get rid of everything.
It's just let's create the clearest fastest path
so that anybody interacting with your stuff
actually gets value out of it
and they can attribute their success back to your framework
because if you have 10,000 hours of video in a platform,
nobody knows what to do with that.
And therefore they think it's a waste of time, money,
and energy and they don't become ambassadors of your program.
And so I really just, I enjoy helping people figure out
how to kind of showcase their brilliance
and their expertise in a way that other people can digest it
and then go out and tell the world about it.
- Yeah, it's kind of like when you're editing a movie,
you have 10 hours of footage
and you have to painstakingly remove all the clutter
and keep only what is the gold
and all what's additive to the actual story
and eliminate the rest.
But to your point, you don't have to throw it out.
You package it over here in a bonus or repurpose that
for a blog post or maybe it's better for social media.
Like it's not all thrown away
but it's just not part of your core framework or deliverable.
I love that you mentioned like editing movies
'cause I know there were a bunch of books behind me
if you're watching on YouTube
but I actually am a big movie junkie too.
And the key thing there is sequencing as well
and understanding the journey of the client
or the person trying to get to the end goal.
And I think that's where a lot of people really struggle
not only because they've been in it
and they've got kind of curse of knowledge
but also because they might have not done it
in the fastest and clearest order
that they turn around and teach it to.
They might have stumbled through it,
hit a few pitfalls, all the things.
And if they feed all of their experience into AI
it doesn't always know like how to sequence it
for somebody else.
It's going off of the person who's used the AI platform.
And so that's where having a human who has this skill set
becomes really valuable because I've used it
to help people build challenges.
I've helped people launch group coaching programs
and then like you mentioned my business partner Adam,
I wrote his entire curriculum
and then eventually became partnered with him
to teach said curriculum because he was like,
you know this better than anybody else
and now I have the nickname of the professor
in his ecosystem.
(laughing)
I got my honorary doctorate rather than finishing that degree.
(laughing) You did get your doctorate with him.
And he is an extraordinary coach
and you two together are such a power team
on one of our first calls.
I said Adam, I like you so much but I love Jess.
I love Jess so this is and here we are.
I'm flattered honored and I'm glad that you see it.
(laughing)
So you brought up the idea of a challenge
and I wanna delve into that.
That's something that you and I have talked about
doing for my business.
It's something that we're gonna do together at some point.
I wanna time it right with the launch of the book
which is now coming out in April.
So probably a month prior to that
we're gonna do our challenge.
And my challenge is gonna be as it stands right now,
the sound bite strategy challenge,
how to create the five phrases that you need
to get more clients and to become memorable
and allow people to be able to understand what you do
so simply that they can share it effortlessly.
And that's really how we become known
for the work that we do.
So Jess and I are talking about doing this project
and I've been through challenges
but I've never gone through it with a mentality
of like how would I recreate this
or how would I do my own challenge.
So. Tell us about how a really good challenge works and how if you were to design
your perfect challenge. Number one, why do people want to do challenges and
number two, how do you make a challenge killer? Oh, thank you for asking this
question because I've been very spicy about this recently. I literally this
week, episode 31 of my podcast, was how to gauge whether or not to spend money
on a membership or a challenge because I just went through a half dozen
different memberships challenges that were so painfully bad that I ended up
rewriting them and sending the pitches to the people because I was like, can I
please help you? And so the premise behind a challenge is it's a replacement
in today's world for a masterclass or a webinar or something like that. And
the key here is that a challenge showcases a small subsection of what you do
in a larger offer. And so this is great for people who are coaches for content
creators or even like agencies. If they're like, hey, you this is a little bit
of like a do it yourself in a contained time frame. And then at the end we can
we can tell you how you can have more if you found value in this small thing.
And so the the thing that I tell people when we enter into the context of the
challenge is it's going to feel like you're not giving anything away as the
expert. It's going to be so hard for you because you feel like you're not
giving enough for the dollar amount value. But the key here is that the the
secret inside of it is not about how much content you deliver. It's about
creating an emotional journey for somebody where they do get the outcome that
the challenge is promising by the end of the number of set days. So whether
your challenges is three days, five days, seven days, I really don't like them
longer than that. Then whatever you're promising to deliver, they get that at
the end and they've gone through this journey with you and they feel so good
about it. That when you're like, hey, if you found value in this, if you got the
outcome, here's the next step. And I'd love to invite you to it. And so the
reason I had those challenges that I felt like we're icky was they had great
names. They they were very clear like, hey, you get this in this number of days.
And every single one of them did not deliver that outcome. Wow. It was
crazy to me. Wow. Give us an example. So without without without dogging on.
Yeah. Yeah. I don't. Yeah. I'm not trying to like be negative about the human
because I love the human. Right. But the human was offering results of a specific
nature. So it was like a double year, whatever kind of thing in five days. I was
so excited about this because I love this human. I've worked with this human
before. I was like, Oh, five days is way better than, you know, the year
container, that's way more costly. I want to see what this is all about. And I
even didn't do the first challenge. So this was a challenge that they'd done
several times. And I was like, it's got all the kinks worked out. It's going to be
amazing. Yeah. So I get on there. And day one is heavy content, heavy IP and no
explanation besides a 15 minute YouTube video that you were supposed to watch as a
prerec. But there was no glossary of terms. There was no, hey, you should have
this outlined before we start. So there was a lot of frustration and
overwhelm of like, I don't know this lingo. I don't know this jargon. I have no
idea what's going on. I feel behind. Day two was a lot more of that. And there
was homework with it. So you had to go learn the thing before you could
understand the thing to then deliver the homework. Day three was a pitch for a
product to help support you in what you learned in day one and day two. And that
was it the whole time. The whole hour of the call was a pitch or a product. They
gave you a free trial of it. But it was still a paid product outside of the
scope of the challenge. Day four and day five was the pitch to the upsell. Wow.
Two days of upsell. So three days of sales, two days of heavy jargon in a five
day container. The math doesn't math there, my friends. And it hurt. Because like
I said, I love this human. Yeah. And so, I mean, you know me well enough to
to appreciate this Chris. But I had, you know, bronchitis a few weeks ago. And I
was on a steroid to deal with the cough. Well, every time I take one, I cannot
sleep to save my life. And I was so worked up over that challenge, not delivering
what I wanted it to. And I had friends that I had put in the challenge and was
like, you should come do it with me and everything. That at three I am when I
wasn't asleep because I just couldn't sleep. I rewrote the challenge using
that creators IP and the transcripts from the calls from day one and day two. And
I turned it into a five day challenge with a workbook at three a.m. on my
phone. I love that. That is that is so you. Yeah. I was like, Hey, I love you. But
here's what these like, this is your IP. I'm not trying to take credit for it.
Right. All I want you to do is understand that what you promised was not
delivered and here's how I believe that you can take somebody on a journey to
actually get the outcome. But how did she respond? Well, her person who's like
her second command was like, thanks. I think we've already got it on lock. I was
like, no, you don't. I promise. So I actually saw her at an event last week in
person. And I was like, Hey, I know you don't read emails, but I need you to go
back and read you and go look at this workbook. And like, let's have a
conversation. And so I still haven't heard from them yet. But I'm like, they're
they've got a new challenge scheduled for like three weeks from now. And I'm
like, can we please talk before this? Oh, my gosh, they have they have like a
gold city. They have no idea how much I could change the trajectory of their
upsell even. Not only is it because like their landing page was so good for
this challenge. And the the title of the challenge was perfect because every
challenge should promise a clearly defined outcome. You get this in this many
days. Like, this is exactly what you get at the end of your commitment. And so
like, there's was gold. And when they talked about what you would get in the
context of five days, like the bullet points sounded great. But they gave all of
that in day one and day two. And so the emotional journey, like, I had a hard
stop on day three. And I had no desire to continue to want to work with them
when all they did was try to sell me on other products and services in the
thing I paid for, right? And I mean, the trust the trust is broken, right? It was
a pain. It was a paid challenge, right? Yes, it was a paid challenge. And so the
framework that works really well for people. And I would tell you this, just
like anybody else, is you have to start with an emotional story to start the
emotional journey. So why does this matter coming from you? So like you, Chris, if
you were doing your sound bites challenge, you would start with a story about
why you needed sound bites. How did they impact your life and your business so
that you build trust with people from the very beginning, right? And what did
it feel like for me? What did it feel like for me not to have sound bites?
Exactly. Yeah, because there's a there's an opportunity cost. There's also an
opportunity lost cost and you need to help people connect with everyone, whichever
one of those two things resonates with them. And so storytelling is an amazing
way to do that. And so if you can start with a story, then the rest of the
challenge you can anchor back to that story. So it gives you that really solid
trust building emotional journey foundation. And then for the majority of the
time, so like, I'll use percentages, let's say, you don't spend a ton of time on
the story, like 10% maybe. And then like 80 85% of the time, you're taking
them through the journey of the steps. Like you are creating the process for
them and walking it through. And you are direct instruction teaching, but you
can also have micro Q&As and things like that along the way that like bread
and crumb to the invitation you're going to make at the end. And then you make
sure at the end that you capture their emotion again. So what did they think they
were getting to what they actually got? What did they have false beliefs around
that now they have true near truth surround, right? And so the end like percentage
is really just making sure that you've walked them through the journey and they
feel like they got what they paid for. And that's when you have the opportunity
after the emotion and the resolution to say, Hey, if there was value in this
for you, if you stay on the call, just a couple extra minutes, I'd love to
invite you to what I what else I do. And you do not make it part of the actual
challenge, right? Because people are paying for something they're paying for an
outcome. You better darn sure, make sure you give them an outcome, right? Right,
right? And it's sorry, I talked about there. No, it's okay, spicy. It's it's okay
to sell, but you don't want that selling to be part of the challenge. You want
it to just be at the end. I love the way you call it an invitation. And it's no
one wants to be sold to, but they would love to be invited to whatever that
next step is. And that's such a different way to present it. When you were
sharing the image that came to mind.
for me was my I have an eight-year-old son named Jude. We both have young boys and on the first day
of kindergarten they took a picture of each kid and it was like kind of like almost a life-size kind
of cut out of this kid. And then at the very last day of kindergarten they did it again and just
showed how much they've grown and it said on the first image it said I couldn't read and then at
the end of the year it said I can read. And we got to take those home and Jude got to hang this
on his wall of like looking at himself as an early kindergartener that couldn't read and then the
transformation that happened. And so I think such a big part of what you're talking about is also
like celebrating that transformation and reiterating that transformation and acknowledging the
transformation and putting a bow on it just like you do at the end of a movie then move on to
the invitation. Exactly. One of the best challenges that I've seen done that I attended to study
and learned from was Graham Cochran's and he's changed the name a couple of times but I think
he calls it like the 10k challenge or something like that because he's like you can sell anything
you know and here you just have to frame it a certain way. And I wanted to rewrite part of his
challenge so I'm not saying it's perfect because I still naturally do that but he was the one that
taught me that invitation language and he shared it as if you know you are at a restaurant and they're
like well would you like a side? Oh would you like dessert? Would you like an appetizer? You're much
more inclined to say yes then be like somebody throwing the menu in your face and saying you have
to buy this you have to buy this and I was like that is so powerful when because people buy through
emotion. And so if you are not creating an emotional journey you're like you said the transformation
for them and reminding them that the transformation happened with so like the visual of Jude is awesome.
Then they're not going to be as tied to it and excited about the offer in an invitation format
at the end. And something that he does that I've also seen done in probably half the other
challenges I've attended is they will take small snippets or cuts from the previous days group
recording and trim out some of the transformations and ah-ha's that people had that remind
and then they play it right at the beginning before they start the next day's content. So it's like
30, 60, 90 seconds I mean it's not a lot. Some I've seen go as long as five minutes and that's too much
but you know it's one of those things where it's like oh so and so said this yesterday about like
they had this belief that changed or they had this idea that changed or they had this win
and by putting that at the beginning it gets people in that emotional state faster
so that the depth is there and depending on how many days you do I mean that can really move
somebody and move the needle from like you are unknown to them to liking you to trusting you to
wanting to buy it from you or work with you right and and so you know Adam and I have run challenges
for his company which is called I love coaching co and we joke I was like I need you to define what
co means because it's a community it's not a company that like you're at a coach of I was like
but it could be cohort collaborative like co could be anything but anyways his his challenge is
the same kind of concept and it's so funny how many people we've been able to convert
from a very low ticket challenge to a high ticket membership by taking them on an emotional
journey and delivering everything that we promised because people go from not knowing you to
trusting you in ours is three days now he used to be five days but and they're like yeah if you
did everything you said you were going to do and I got this result in three days then when you
ask me for something else I believe that that's going to be a thing you believe that you've been
that for me yeah you've been that you've been able to solve a micro problem for them in three days
and if you can solve a micro problem for me in three days I can only imagine the bigger problems
that you can solve for me exactly yeah exactly and that's why this works so well for coaches and
consultants and anybody who's in that kind of creator space because I mean we're we're in a weird
era now and I've said this on several other podcasts too I believe that we're past the information
age you can get in from information for free anywhere we're past the era of buying how to's because
you can ask AI for it again Google it whatever and now we're in this new era of people paying
for proximity to people who have done the thing and they're paying for how use and so a challenge
is a micro how you it's oh I want to achieve this thing I want to have this result I want this
outcome this person says they've done it and now in three days they're going to teach me how to
do it cool and so people are more willing now to buy into a challenge or something where
there's proximity they can get questions answered because they're learning a specific path to an
outcome not just buying a PDF or buying a course that doesn't give that human feedback or the
ability to figure out what the story is for them that might be slightly different from the
original presenter and so I just I think that's a really powerful thing for anybody who's in
this space of understanding that I I don't want to say courses are completely dead but I think
courses are much more dead than they were three years ago because of the advent of AI and people
are now desperate for proximity to real people they want authentic humans I think enough people
have bought enough courses and not gone through them or not finished them or started them and
bailed and they realize now more than ever that they need their hand held and they they to your
point just crave the guidance like the actual human guidance someone's brain who knows how on
their unique situation because everyone's different there's no cookie cutter solution that's
going to fit everybody like there's just nuance for every every coach consultant business owner
every everybody and so that proximity I think is incredibly valuable yeah it is well and it's
valuable whether you're doing a small contained thing like a challenge masterclass training whatever
you're calling it or a larger thing which is your membership your community your group coaching
whatever you're calling that I mean that's it's the same thing at scale that people would rather
spend five 10 20 thousand on something where they're getting proximity to humans one that's already
done it so like a founder but also others who are going along the same journey that they're going
along towards the same outcome so that they don't feel alone in it and and I am very passionate about
what it looks like to have a good quality group coaching your membership and the three pillars
that you need inside of that because I've I've watched some of the foremost leaders in certain
thought leadership spaces build things that flopped that were very high ticket and it hurts to watch
because I'm like I respected you I might have even potentially put you on a pedestal that I
probably shouldn't have done that but like I respected you I spent a ton of money to be in this room
and all you gave me was a book report and a Slack channel and I'm like that's not what I wanted
so what are the three pillars so the three pillars in my world I think of it like a three-legged stool
and the seat is the that defined outcome that pay off that you're promising people and each
leg is important to actually have that CP balance so we talked about proximity right and this
is not an ego play this is ability to get feedback from somebody who's already gone through the
process and done the thing so proximity is not about celebrity it's about success in the outcome
space the second one is that that process what are the steps that you took in like a three to five
step process to get there nobody wants 52 weeks of something I had somebody try to sell me on a
high ticket coaching when they told me it was a coffee and connection call and I was like oh that
was a bait and switch and they were trying to sell me on a binder of 52 weeks of homework as part
of it along with daily one hour calls to get the homework done in and I was like I would pay to not
be in that thank you like how much can I pay to get off this call right now but like seriously so
that people want a clear simple clean process which is where my love language is and then thirdly
they want peers they want proximity to other humans that are trying to get that same outcome so
they're not doing it alone because you can go read a book
alone, you can go play with your AI alone. If you're paying for something, you're paying to be in
the room with other people so that you can connect and learn from them and not do this in a silo,
or inside a bottle, as we were talking about earlier. There's so much power in the community part,
the peer part, because I think people, people want their hand held, and they think they want one-on-one,
but they really need that peer community because so much encouragement, guidance,
insights, support, comes from people literally navigating the journey with you. Yes,
you get that proximity, too. So you get the best in both worlds, but you do absolutely need
all three of those. Well, and legs. Yeah, yeah. It's such an interesting thing, because typically,
like in I love coaching, so we teach people how to build coaching businesses from their unique
experience and expertise. And so we provide the framework and the coaching on building a business,
and then you get to go build whatever you want, which is a beautiful thing. And so in the framework,
we teach people how to start with one-on-one coaching, and before they try to step into group coaching,
because I've watched too many people try to build it around their proximity, but they don't have a
leg of process because they've never coached before, or they haven't streamlined their coaching
into one outcome. And they throw people who are not connected to each other into a group,
and then the group becomes dead silent because there's nothing uniting them. They're not all
working towards the same thing. And so for me, I am very, very determined to help people understand
that people need people, people want people, but you do not just build a group arbitrarily,
because it needs all three of those legs to grow and thrive, not just survive. And so that's
where a lot of my personal coaching and consulting comes in outside of things, you know, related to
I love coaching, and the big idea is made simple, is I will help people build a challenge, build a
community, launch it, all that, to make sure that they have all three of those legs in place, so that
they don't feel like they're having to carry the entire stool on their back while holding the
proximity leg. That's a powerful visual right there. Yeah, I think in pictures. Okay, so
the perfect challenge, the perfect challenge. I think a three-day is the perfect length. I think
people, I like it. I just think three feels good for people. It depends on what you're trying to
accomplish, but if you can do it in three days, that's way more valuable than having to do it in
five days to people. Yeah, yeah. I like three days a lot. I would, I would typically cap it at five.
The reason I said seven is maybe you haven't run over a seven-day window, but it's not meeting all
seven days. I get it. Yeah, and so typically I really love three to four meeting days,
and so you can do it with three days of content, and then a bonus Q&A, or VIP day, or something like
that, and that works beautifully. Or a lot of challenges that I've done is if you offer VIP extra
coaching, which is literally no prep, you just answer questions. You can do it where like the Q&A
is before or after the live training, and you just use a different like Zoom link, or whatever
you're using platform. Why is there? Yeah. So that way people understand, hey, you're going to get
the defined outcome in the main session, the general admission ticket, the VIP stuff, the extra
stuff, that's that's an upsell, but that proximity should help you get there even faster. So, yeah,
ideally three days of teaching, yeah, and and in less than a seven-day window.
I like it. Yeah, the the challenge that you and I had designed was three days, and then on the
third day after the teaching, we're going to have Donald Miller come in and do hot seat coaching,
which is the VIP upsell offer, like getting his eyes on your business, and I'll be I will be
there too, but that's a way to keep it to three days. I could have and I still might make the VIP
portion of it day four, but I really like I like the idea of having that third day. You've got
that momentum and getting that VIP experience after that. I think out of all the ones I've been in
and I think I'm I'm high double digits now, like I collect I collect things Chris. I think I like
the ones where the VIP stuff is on the same day as the training because I can time block and my
head is in it like you said. So there's no like task switching for me or like mental train shifting,
and that's really powerful. And so the way that you designed yours is great because yours is
unique with the Donald Miller play in, but if it's just you delivering like Adam and I do for
I love coaching, we actually do VIP every day. And so that's an option as well, and that when you
so the average challenge is a $97 challenge with the VIP upsell being $297, like that is almost the
standard in the industry as of this recording. I love it. Okay. And so you know 97 gets you
for most people that's three hours, right? If you're doing an hour three days a week. Yeah.
And that's about the same as a masterclass or a webinar. So it's it's really the same thing,
but it's broken up. Like if you think about the length of time when you're teaching a webinar
or a masterclass, all you have to do is take that time block and turn it sideways. And that becomes
the arc of your challenge. So it's really the same concept. Start with the story, teach the steps
in a bite size emotional journey where people get quick wins along the way. And then recap it,
make sure that you get, you know, what you paid for at the end. And yeah. And then your VIP portion
is at the end of the call every day like a queue. It can be beginning of a call. It can be
end of the call. It can be extra call. It really doesn't matter. But I the ones more of them
are on the same day. So that way people are thinking about it. So like yours being on the end
of day three is perfect for that. Right. And VIP is only Q and A. So it's only paying for proximity
to the person hosting. Got it. It is no extra content. Unless you're delivering like an answer to
a question that then becomes valuable to the people listening. But it's your the experts eyes on
your situation. And that's the VIP. I love it. So simple. It is. Well, we heard a line Adam and I
somewhere forget who I can attribute it to. But they said people pay to pay attention. People pay
a lot to pay a lot of attention. So the higher the ticket, the more likely people are invested in
getting the outcome that they're paying for. And so I like this framing of hey, general admission
is going to get exactly what they paid for. They're getting this framework, this model, this whatever.
The VIP, they're paying for extra proximity and extra feedback in their world. And that that's where
they're paying more, but they get more attention. And so they give more attention at the same time.
And what we found math wise, super interesting for anybody doing the upsell thing is typically
we find that on average, a challenge has about 20% VIPs. And then you can convert about 20% of those
into your upsell if you do that invitation the right way. There are some that go way higher and do
more, but Pareto's principle of the 80 20 rule works really well math wise for the average of challenges
and upsells. Wow. And then the people who pay VIP are way more likely to become clients.
Is that what you're saying? Because they've already paid more. And then they get more value. And
there's more proximity. So the trust is gained faster. Your authority has grown larger in their
eyes. So therefore they are more likely to pay attention. So if you're a math person and numbers
and percent don't scare you and fractions don't scare you. 20% of 20% means that somebody who is
buying the VIP and then your upsell is 16 times more valuable than the person who bought a general
admission ticket. Because 20% is you know one fifth and then you kind of do the math of 20% of 20%
and so that makes them 16 times more more valuable. And I think that piece and that mindset of
oh not all attendees are equal. Yeah. And and so understanding also like your ratio of conversion
and where you're getting people from and what your goals are on the other side of a challenge
can also really help you because for me it's not about having 10,000 people in a challenge
if my goal is a certain number of upsells on the other side. It's how many do I need in VIP
because if that's roughly 20% and then how many do I want I can go and reverse engineer that.
And that to me is a freeing thing for people who are
our big thinkers and high achievers
and have big vision, but then they're like overwhelmed
by the almost like the selling
or the recruiting of a challenge.
It's like, no, if you want five people on the other side,
multiply that by five, you need 25 VIPs,
multiply that by five, that needs to be 125 in the challenge.
- That's adorable numbers.
- It's a doable number and it removes all the drama
and all the emotion from it.
It's a number numbers game, yeah.
- Okay, so my first career I told you I was a teacher,
I actually taught history and math,
which are like the two most considered boring subjects
or least emotional subjects,
but I think they made people the most emotional
because what they didn't understand that.
- Right, and so I laugh now
because I think in you know,
persents and fractions and all this stuff,
and I use math to help me remove emotion
from things when I'm feeling it,
and people look at me like I'm nuts,
and I was like, no, math does not make me emotional,
it makes the path clear and easy.
Literally the path is in the math, my friends.
(laughing)
I love that.
So how frequently do you recommend doing a challenge
and how frequently do you do your challenges?
- Oh, that's a good question.
I would say don't do it so redundantly
that you burn out like your email list
if you've got an email list or an audience on socials.
So I see it work really well either like every other month
or quarterly,
and then you can filter in other events in between if you want
or that way it becomes kind of a cadence
where people know it's coming
and they get a little fomo if they miss out
and they hear great things,
but it's not so far away that they can't buy into the next one
and know the next one is coming.
And so I really like quarterly,
and then what I do with I love coaching is
we have live events in Charleston at the headquarters
in other months,
or we'll do a webinar solving a specific problem
that isn't related to the challenge
but is related to a different facet of coaching
and invite people and that's a paid class
that's usually 90 to 120 minutes.
So they're getting about the same thing for the same price
but we don't do a VIP upsell on those.
- Got it.
- Cool.
- Yeah, you can sprinkle in other engagements
and ways to connect with people.
But I love the idea of a quarterly challenge,
a three-day challenge as a way of just continually
and relatively not totally effortless
but once you get it down to a well-oiled machine
it just becomes rinse repeat.
But what a wonderful way to bring new potential clients
into your world, bring new followers
and if they don't become clients, that they can share you
with the people that they know that might be a right fit for you.
- Yeah, and there's a lot of books out there.
I think I've read them all on like launches
and building groups and cohorts and programs.
And I love a challenge as an easy way
to extend an invitation to a group of people
who are more ready buyers
without feeling like you have to do a hard sales launch.
And so I think that's a really powerful thing of
you are changing your own psychology
instead of I have to go sell this
as so many seats to this thing.
You can say, "Hey, I want this many people I want in these seats,
let me go do an invitation to a warm audience."
- And that is so powerful.
- And an engaged and warm audience.
I think when we think about the last 10 years,
I think the downloadable PDF is played.
Nobody wants that.
Nobody wants a DIY course anymore.
People are the formula of a master class or webinar
is also played and people are tired of being sold to.
And I feel like the challenge is much more relevant,
much more current, much more ethical on us.
- It is.
- Then the way we've done things in the past.
- Well, you hit the nail on the head
of people are being tired of being sold to.
And I think anything that's labeled a webinar
is automatically now filtered through people's ears
as a sales pitch.
And they're like, "I will only sign up for webinar
if and then I will like log in, leave my camera off
and wait till they give us the discount code or offer
for the thing that I was actually planning on buying
at the end or two thirds of the way through
like the pitch usually goes."
And so I love, I still think there's space
for master classes, workshops and challenges
because they are delivering something specific.
And so yes, webinars are dead, courses are dead,
PDFs are dead in my world.
If they are not specifically giving somebody an outcome.
And so, and I love that you said it, it's more ethical
because I agree.
I'm like, I don't feel like I'm selling anything.
I'm giving whatever somebody paid for every single day.
- Right.
And rather than just like delivering this vast amount
of information and hoping and praying that they digest it,
the challenge allows it to work with the human brain
and be more bite-sized and feel more supportive
and just much more engaging.
It's such a wonderful way to market.
I look at it as if your membership, your offer
that you have the big thing the core offer
on the other side of this is like a whole book's worth
of knowledge, a challenge, you know, master class,
whatever is like the first chapter of that book.
So you can give away context and you can give away
the framing of everything they would get.
And you're delivering something in a container.
So you get to put your best foot forward
to keep encouraging people to keep reading essentially.
So we call it the first chapter framework
inside of I love coaching because it's really truly that
of you give away enough, but it's still attached
to everything you're doing.
It's not something totally random or different.
- Right.
- And so you're wetting their whistle
and getting them excited about reading the rest of the book.
- Mm-hmm.
- And so for me, I just, I think that there's more opportunity
for more people to do this.
And I'll tell you, it's not hard.
And like I love you said, you can rinse and repeat it.
It is, like it's so great.
Adam and I have run this, I love coaching challenge
for like a year and a half now.
So we've done it a number of times.
I tweaked and iterated along the way
to make sure it was more valuable.
And like I said, we shortened it from five to three days.
But at the same time, he and I can show up and come,
like very, very committedly and articulately,
say everything because we know that that leads to this outcome
which then informs everybody of what they could get
if they joined our annual membership
and worked with us, whether in a group setting
or one-on-one or both.
And so when you can get to that space of,
oh, I don't have to create something new.
I have to take a little piece of my best stuff
and give that like best foot forward.
Then it, again, builds more trust and authenticity in you
because it's not a performative thing
where you're not delivering.
- Mic drop moment.
- I need to get like a Styrofoam microphone
so I can just like drop it on these holes.
Oh, I have is from my friend Adley Kinsman
at Rubber Chicken, can I drop that?
- You can drop that, that's, yeah, for drop.
Tiny mic drop.
- Tiny mic drop, I love this.
- Jess, it has been so much fun talking with you today.
I honestly, I feel like we should do a monthly
professor Jess comes to the show
and just infuse all your wisdom.
- I mean, I'm always happy to come back, Chris.
All you have to do is tell me when
and what I'm talking about and I will be here.
- I so appreciate the opportunity to have this conversation
'cause like I said, I got opinions for days.
- You do, if we need to hear more of you.
- So thank you, where can, where can we find you?
- Yeah, I'm on all major platforms
as the Jess Weber, double S, double B,
not because I'm full of BS, I promise.
And so you can find me on all social media platforms.
My podcast is big ideas made simple
and that's on all platforms as well.
So I would love to connect with anybody
if there's value or you heard something
or you've got a question or you wanna go verbally spar,
let's go.
(laughing)
- That's awesome, all right, thanks so much Jess.
- Thank you, Chris.
- Is your website turning away potential clients?
I can help you turn that around.
Book a money-making messaging call with me today
and we'll transform your story
into your most powerful sales tool.
That's all for this episode of From Click to Client.
Don't forget to subscribe and follow.
I'm Chris Jones and I'll see you next time.
Podcast Summary
Key Points:
Jess Weber helps clients simplify complex ideas and organize their intellectual property into clear, actionable frameworks that are easy to digest and share.
She uses a "big ideas made simple" approach to bridge the gap between a client’s vision and current assets, creating structured, outcome-driven pathways.
Jess and her partner Adam design challenges that deliver defined outcomes in a short, emotionally engaging journey—typically three days—building trust through storytelling, micro-wins, and transformation.
A successful challenge emphasizes emotional journey over content volume, with a clear outcome, a streamlined process, and peer community to foster real human connection.
The VIP upsell is positioned as a premium invitation to proximity and feedback, not as a sales pitch, increasing conversion rates and client value significantly.
Challenges serve as a modern, ethical alternative to outdated formats like PDFs or webinars, offering tangible results and building trust through proven human-led guidance.
Jess emphasizes that challenges are not redundant but strategic, recommended quarterly to maintain audience engagement without burnout.
The challenge model acts as a "first chapter" of a larger offering, exciting potential clients and building momentum for deeper engagement with a full membership or program.
Summary:
Jess Weber specializes in helping entrepreneurs and coaches simplify their complex ideas and intellectual property into clear, actionable, and emotionally engaging frameworks. Through her "big ideas made simple" approach, she guides clients to define their vision, organize their assets, and create structured pathways from where they are to where they want to be. Central to her work is the design of short, high-impact challenges—typically three days long—that deliver specific outcomes through storytelling, emotional journeys, and micro-wins.
These challenges build trust by focusing on transformation, not just content, and include a VIP upsell that offers proximity and feedback, not sales. Jess emphasizes that such challenges are more effective than traditional webinars, courses, or PDFs because they align with modern consumer needs for authentic, human-led experiences. The model is scalable, repeatable, and designed to serve as a “first chapter” of a larger offering, effectively introducing new clients to a business while nurturing trust and loyalty.
Her method combines emotional intelligence, strategic structure, and proven results, making it a powerful tool for coaches, consultants, and creators seeking to grow their businesses through meaningful connection.
FAQs
Jess helps clients simplify and organize their complex ideas into clear, actionable frameworks. She focuses on creating a 'big ideas made simple' approach that makes their expertise digestible and impactful for others.
Jess analyzes a client's IP and filters it to identify what aligns with their core outcome. She removes clutter and organizes the remaining content into a clear, efficient framework that delivers value and helps clients achieve their goals.
A good challenge provides a clear, emotionally driven journey with defined outcomes. It starts with a story, delivers step-by-step guidance, includes quick wins, and ends with a recap of the transformation, all within a short timeframe like three days.
Challenges are more engaging and human-centered because they focus on delivering specific outcomes through a structured, emotional journey. They avoid overwhelming audiences with information and build trust through real results and proximity.
She structures challenges with a story-driven opening, three days of direct instruction, micro-interactive elements, and a powerful recap that emphasizes transformation. A VIP day or Q&A is offered at the end to build trust and invite upsells.
The three pillars are a defined outcome, a clear and simple process, and peer community. Together, they create a balanced, supportive environment where participants feel guided, connected, and motivated to achieve results.
Chat with AI
Loading...
Pro features
Go deeper with this episode
Unlock creator-grade tools that turn any transcript into show notes and subtitle files.