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December 3, 2024 67 mins

In this episode of The Intern Whisperer Podcast, host Isabella Johnston sits down with Chuck Goldstone, founder of Chuck Goldstone | Strategies and Stories and the New Venture Institute. Chuck has coached and mentored thousands of startups across the globe, helping them use storytelling and strategic communication to secure funding, create partnerships, and stand out in competitive markets.

Chuck shares insights from his book Strategies & Stories, offering a framework for entrepreneurs to communicate effectively and engage their audience. He discusses the importance of differentiation in a crowded field, the power of simplicity, and how to craft compelling stories that move investors and markets to action. Chuck also dives into the impact of AI on entrepreneurship and how it will shape communication strategies, customer engagement, and business growth by 2030.

Whether you’re an aspiring entrepreneur, investor, or job seeker, Chuck’s expertise will help you craft your story, build stronger connections, and achieve your goals.

Key Takeaways:

  1. The power of storytelling in differentiating your startup.
  2. How to simplify complex messages for your audience.
  3. The evolving role of AI in communication and entrepreneurship.
  4. Best mentoring advice for entrepreneurs and job seekers.

Links:

Strategies & Stories: Tell Me More Book by Chuck Goldstone on Amazon (link below) https://www.amazon.com/Strategies-Stories-Indispensable-Entrepreneurs-Innovators/dp/B0CGWYV5R2 

 

Websites: https://chuckgoldstone.com/ 

                https://strategiesandstories.com 

Free:        https://chucksroundtable.com 

LinkedIn:  https://www.linkedin.com/in/chuckgoldstone/ 

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Hi everyone, my name is Isabella Johnston.

(00:02):
I'm the host of the Intern Whisper Podcast,
which is brought to you by Employers for Change.
Helping hiring teams to recruit and upscale interns
to employees through mission, values, beliefs,
and core skills.
Learn more at www.e4c.tech.
And today's guest is Chuck Goldstone,
who I met at the prepare for VC Winter Oasis pitch.

(00:24):
He is the founder of Chuck Goldstone Strategies and Stories.
And the new Venture Institute.
Chuck has coached, mentored, and trained thousands
of startups across the US and throughout Europe,
Latin America and Asia.
His pioneering communications model book,
Shameless Plug, right here, and workshops,

(00:47):
along with the power of story, have helped emerging
and growing companies redefine their business strategies,
secure funding, create strategic partnerships,
and drive more investors and markets to action.
So Chuck, welcome to the show.
Thank you, and thank you for that introduction.
I would hire that guy.

(01:08):
So yeah, I would too.
And just so our listeners know, or viewers,
if you see a cat's tail popping up,
it's because Chuck has a guest in the room with him.
It's Easter egg if you will.
We'll have to share the stage with all of the cat.
Yes.
Could be here.

(01:29):
Yes, it is.
It was nice meeting you in.
My name is Isabella Johnston.
I'm the host of the Intern Whisper podcast,
which is brought to you by Employers for Change,
helping hiring teams to recruit and upscale interns
to employees through mission, values, beliefs, and core skills.
Learn more at www.e4c.tech.

(01:50):
And today's guest is Chuck Goldstone,
who I met at the prepare for BC Winter Oasis pitch.
He is the founder of Chuck Goldstone Strategies and Stories
and the New Venture Institute.
Chuck has coached, mentored, and trained thousands of startups
across the US and throughout Europe, Latin America and Asia.

(02:12):
This pioneering communications model book,
Shameless Plug, right here, and workshops,
along with the power of story, have helped emerging
and growing companies redefine their business strategies,
secure funding, create strategic partnerships,
and drive more investors and markets to action.
So Chuck, welcome to the show.

(02:36):
Thank you, and thank you for that introduction.
I would hire that guy.
Oh, yeah, I would too.
And just so our listeners know, or viewers,
if you see a cat's tail popping up,
it's because Chuck has a guest in the room with him.
It's Easter egg if you will.
Well, we'll have to share the stage with all of the cat.

(03:00):
Yes.
Could be here.
Yes, it is.
It was nice meeting you in Boston
when you were doing the prepare for BC program,
which I've been a supporter of prepare for BC,
been a sponsor for a number of years.
I'm really impressed with what it is that they do.

(03:23):
That's good to hear.
I love those guys.
I like them.
When I say I love them, I love them.
They've been so helpful.
They've been really good people to work with.
And Jason, I just, who doesn't like Jason?
He's the best.
He gives so much of himself.
So does Steve.
They both do, honestly.
But let's just jump into the interview.

(03:45):
You have an extensive background in working
with both startups and global companies.
What do you think is the most important factor when it comes
to storytelling for startups?
Well, one thing I've recognized for the years
is that coming up with this really great idea that's

(04:08):
going to change the world and make you rich and famous,
coming up with that idea is actually
the second most important thing that startup will do
to become successful.
The first is convincing others, because we don't do this alone.
We need the support of an ecosystem

(04:29):
that supports entrepreneurship.
We need the support of investors.
If we're moving forward, we need the support, obviously,
of our market.
How to reach them is really the most important factor.
And I have seen somebody extraordinary companies

(04:51):
falter and some out not fail, not because the idea was good.
But because they couldn't communicate clearly
what it is that they do.
So I would say one of the major attributes for success
is the leadership skill that we call communication.

(05:13):
It's identifying the right people,
but knowing how to reach them, it's more than just conveying facts.
We've got to be able to connect to an audience.
And I think that is where the power of story comes in.
And that has been my focus.
I'm not a technical guy.
I'm not a finance guy.
Matter of fact, if you called me in to do your term sheet,

(05:37):
you probably wouldn't get funded and you may go to jail.
Oh, no.
Oh, yes.
And if you hear that I'm an air traffic controller
or some other technology that keeps planes in the sky,
likely you're going to die.
So don't rely on me for that.

(05:58):
But I think if I have any talent for this community,
it is really helping people find their voice,
find their story, differentiate themselves
from the rest of the noise out there.
And frankly, to be remembered.
So connection is really, I think, one of the most important

(06:23):
attributes of successful companies.
And I think they do that to their ability
to understand who that audience is and communicate
in a way that both interests are reflected.
I like that very much.
So the second part of the question is,
how can they differentiate themselves in the market?

(06:47):
That is always tricky.
Because to me, when I've gone through a lot
of the accelerator programs, we're
always told look at our competitors.
And they say to differentiate, but I always
want to put all of the features of like, yes, I'm all of this
and I'm this.
And I don't think that's the right way,

(07:09):
because it hasn't helped me get funding.
No.
And I think that you're discovering
what a lot of startups have discovered.
First of all, it's not just about your competition.
I mean, you're competing.
If you're out there, you're not only competing
with other companies who do the same thing.
You're competing with other companies

(07:31):
who are doing different things, because you're all
after the same year and wallards.
So it's really beyond that.
It's you need to differentiate in that you
need to be able to differentiate from not only
the people who are your competitors,

(07:52):
but from all the noise out there.
We're bombarded all the time with messages.
The question is, what is it that's going to make us be remembered?
Call back.
And it's about differentiation.
Now, differentiation is, let's imagine for a minute,
well, we know you're in the edtech space.

(08:15):
Once you say edtech before you really get into your explanation,
I'm already relating to everything
that I know about edtech.
And I'm now throwing you in the category with everyone else.
So now you're in this big pyramid with a bunch of folks
living inside the pyramid.
You're all edtech folks.

(08:39):
So now you're in one in, let's say, 97,
because you haven't differentiated.
If you can differentiate, it's, wait a minute, yeah, I do that,
because you've got to establish your industry first.
But yes, I do that.
But wait, there's more.
This is what I do that makes me not only different,

(09:00):
but perhaps attractive to you.
Now, if you can know your audience well enough to know what's important for them,
if you can get that thing that differentiates you to align with what those
interests are, then all of a sudden you have their attention.
Here's the thing that I've discovered.
I talk about this in the book as well, that we connect based on similarities.

(09:21):
I will know who you are because you're in the edtech space,
and I know a little bit about the edtech space, or at least I've heard about.
But the question is, when you're in there, like you say, you're,
when a 97, I connect with you.
I pay attention to you because you do something similar to what I understand.

(09:43):
We don't.
I just had Siri jump into the conversation.
So she said, I heard something.
Yes, OK.
We engage based on similarities, but we make decisions based on differences.
I'll give you an example.

(10:05):
I had to buy a new refrigerator, which I think I have to buy every four years.
They're somehow timed to fail.
And they're expensive these days.
I remember my grandmother's refrigerator.
She had for like generations.
Refrigerators aren't like that anymore.
So anyway, I needed to buy a new refrigerator.
Refrigerators all do the same thing.

(10:26):
They if they when they work, and that is they keep stuff cold.
So right now there's a gazillion refrigerators that I could buy,
but I bought the one that I finally bought, not based on how
similar it was to other refrigerators, but what were those features that provided
benefits for me, the things that I really needed.

(10:48):
So it could have been another big triangle with 97 other refrigerators, but it stood out.
Now, what happens is once you stand down, here's what's interesting.
You were one in 97.
Now you're one in two.
It's either you or somebody in that big pile.
So find the thing that people will remember that makes you seem a bit different than everybody

(11:14):
else.
And we all have something that will provide us with our own unique voice.
So find that because that's the thing that people are going to remember.
I really like that conversation that you just, that analogy and the conversation though.

(11:36):
Because I cannot tell you how many times I've heard some stuff from others, but never
quite the way that you said it and quite the way, honestly, that another group has said
to me.
And I feel like that truly makes sense because people always want to have the latest thing,
maybe not because it's the latest thing, but because it has one more thing that they want,

(12:01):
right?
Well, one of the problems is the following.
Your audience doesn't know much about you in the beginning.
If we over tell our story, we have a greater risk of losing our audience.
One, because we may get way too technical, we may get too irrelevant.

(12:29):
We may simply confuse them.
We may inundate them with so much that they cannot hold anymore.
But here's the worst part.
If you list everything that you do, the need to know, and here, let me give you all this
nice to know stuff.
If you do that, your audience cannot necessarily differentiate between the nice to know and
the need to know.

(12:51):
And they're going to forget the majority.
I mean, there's something called cognitive load theory, which is very interesting, but
how much information we can intake and hold.
And we can only in sort of a learning chunk only remember so much until it is embedded.
If we tell people all the need to know and then lose them with a big pile of nice to

(13:15):
know, they're going to forget a whole lot of it.
And they may actually start be forgetting some of the important things because they can't
differentiate at least in the beginning between what you have as a major feature and what
you might have as a minor feature.
And so one of those features out of context, and they begin to think that's what you do.
And it may be different from what you really do.

(13:37):
So to clarify, because I really want to make sure I'm understanding.
So the need to know is what I how I'm different.
The nice to know is how I'm everything else or is it up?
No, no, not necessarily.
No, what I'm saying is you need to there are two independent things.
You need to find that thing that differentiates you.
But when this is another point, the other point is when you're explaining what you do, you do not want to

(14:00):
overtell your story, especially in the beginning.
You need to start with a big picture and you don't want to lose people in in great detail because if you
sliver them with too much detail, they're not going to remember everything.
And they may end up remembering some of the things that aren't terribly important, but forget about the
things that really are.

(14:21):
And that may create a picture of you that is really not quite accurate.
So I warn people, I've got about 110 overall tips and principles that I share that I've learned through
through the years.
And one of them is you do not try not to tell too much too quickly.

(14:46):
It's a challenge because we're so close to what it is that we want to do that we do.
We sometimes can't make that differentiation ourselves.
Why do people tell too much?
Well, sometimes it's easier to tell too much than too little.
It's easier to write the long letter than the short letter.

(15:08):
Sometimes people do it for that reason.
Sometimes they think if I throw everything out, the audience will get it.
They'll connect the dots and the audience frequently does not.
And the worst thing is sometimes people do it just to impress and you cannot impress if you've lost
people.
You impress if you make complexity simple.
If you summarize, so they say, yeah, I get it.

(15:32):
Then you know you have, then you know you have connected.
So two different points, one, find your differentiation.
But another point is do not, especially in the beginning,
overtell your story because that is where you may lose them.
Find out what is the content that is specific to that particular audience.
What is important to them?

(15:54):
Create that big picture.
I'll tell you the folks who sometimes struggle a little bit more and where the real challenge is.
And that is people who are in a field that's very technical because there is the interest
frequently to tell what is interesting to them as the developer.
And that is how it works.
In the beginning, people don't care how it works.

(16:18):
What they want to know is why it needs to exist and why that's important to them.
So one of the things that keep coming back to is, yes, we all know you start with a problem
or the business cannot doesn't have to be a problem yourself.
And it could be an opportunity that you're bringing people.
You know, identify what it is that is important to the audience and show who you are

(16:43):
or what you do through that lens of here is the benefit as it answers the needs that you have.
And if you can do that, there's every likelihood that you can you can connect.
Good stuff there, Chuck.
So let's talk about your book again.

(17:05):
Strategies and stories right here, folks.
For those of you.
Sorry, I have something just like that behind me.
Right behind you.
I don't know about you, but I have one that's autographed by the author.
Oops, right here.
Well, look at that.
Yeah, I don't know if you autographed something on the back if your autograph is on that one.

(17:27):
But anyway, let's talk about your book because it's out there and, you know, we'll be sharing QR codes
and links and stuff like that.
So people will the nice thing about the book is it not only has the five pillars
that I could explain in a moment and about practices, but it has a step-by-step process.
But it also has a downloadable workbook, 90 pages, 35 worksheets that actually take you

(17:57):
through the process from the very beginning in your strategy and works you
entire through your entire story, which will inform at that point your pitch.
I wrote this book because I have coached for a long time companies to, you know,
create their investor decks or marketing programs to create their story.

(18:21):
First of all, pitch and story are two different things.
We pitch the end when we want to beg for something.
Our MVP is done.
We know we need.
Investment money.
We need funding or we are out there marketing for our customers or clients.

(18:48):
We do that in the end.
But what you need is story.
Story needs to start at the very beginning day one.
You need to be able to articulate to the world what it is that you do and why that's important to them.
And.
I see very frequently the problem that people are are not able to do that.

(19:11):
But let me tell you the reason why you need story from day one.
Number one, the thing that we know in any kind of venture is is there a market?
Can you validate the market?
So when you're out there telling the world what you do, if you're not telling it accurately,
the data you get is not going to be accurate.

(19:32):
So that's that's one reason.
Another reason is our story underpins every conversation we will ever have.
The third thing is as we articulate a story, something very interesting happens.
Sometimes as we're telling our story or explaining something to someone,
we hear ourselves saying something that we didn't even know existed.

(19:56):
It comes out from our unconscious that sometimes smarter than we are.
So sometimes and we all do this.
It's all of a sudden we have this insight as we're telling people what it is that we do.
The fourth reason is also very important.
And that is if you wait until the end to create your story, you're now adding a whole lot of time

(20:17):
when you should be out there actually actually telling your story.
You're actually pitching fundamentally that creates a problem of not only a delay,
but what you have lost is the ability to do trial and error and get rid of all the mistakes
before you hit your important audiences.
I see too many people rehearsing in front of their first audience.

(20:42):
So what you want to do is create your story as you're creating your idea,
your technology, your service, whatever it happens to be.
Because by listening to yourself, you will also do the most important thing in
the development of a venture.

(21:03):
And that is you will listen to yourself, make adjustments, and you will pivot.
So for all of these reasons, I tell people that you need to create your story,
which essentially informs your strategy.
I named my company and the book Strategies and Stories.
And the reason is they're the same thing.

(21:26):
Your story is the narrative that you tell to the outside world.
That's your story.
Your strategy is the story that you tell yourself and your team.
And that's the thing that keeps evolving.
So the book, somebody said, how long did it take to write the book?
And I said, about 15 years and six months.

(21:49):
I've been procrastinating for 15 years.
It took me six months to write.
So it was a very long process of procrastination.
I'll tell you a quick story.
And this is actually a true story.
We all have a pile of books near our bedside.
And we get a new book, we put it on the top.
And we say, I'm going to get around to reading that book at some point.

(22:11):
I swear, I'm going to read next week, I'm going to start that book.
And then a week after, and we still haven't done it.
At the bottom of the pile, and I tell you, this is absolutely true.
I noticed what the book on the bottom of the pile.
And it was on procrastination.
So there you go.
But anyway, it became a labor of love because the joy that I've had

(22:36):
is working with companies to help them try to articulate who it is that they are.
My first company that I had before this worked with large corporate clients,
who are Pepsi, Cola, and Curry, and AstraZeneca, and the Air Force, and
folks like that that were global companies.

(22:57):
But I got smitten by the startup world.
Now they lack one thing that large companies have.
What is that?
We're a money.
That's the word.
However, I see so much potential there.
And I see so many really great ideas that I know will succeed
with the proper kind of mentorship and guidance.

(23:20):
And that's been the thrill that I've had is watching companies that
initially were struggling, trying to figure out how to become successful.
But let me tell you one other thing.
A lot of my focus is with emerging companies, startups, early stage,
scaling companies, companies looking for additional long-term funding,

(23:43):
even still some mature companies.
But here's an interesting audience that I'm getting more and more.
And that is job seekers.
And one of the things I discovered and let them know is you're just like a,
if you're looking for a job, you're just like a startup.
You need to brand yourself.

(24:04):
You need to tell a good story.
You need to connect to the audience.
And you must differentiate.
I think the important thing, we rely very frequently job seekers on your resume.
Your resume tells the world important stuff, but it tells you what you have done in the past.
What I think is important in terms of the story is you say,

(24:27):
here's how what I did in the past is going to help you and employer in the future.
It's the same thing with a startup.
Here's all the work we've done in the past.
Here's our product and here's how it's going to help you.
So I think that startups and career seekers are really pretty much the same thing.

(24:51):
I'll tell you a little story.
So I had just graduated with my MBA and I'm going to hope that I get your approval.
This is what I'm hoping you're going to tell me I did.
I did good.
So I was interviewing with the Nature Conservancy and I was interviewing to be a
grants administrator and a financial analyst.

(25:12):
I was with five people, round robin interview.
And the last question was, you don't have any experience.
Why should we hire you?
And I told them, I said, well, I looked up the company and I said, I believe because
I had to work so hard with my finance, my accounting and they knew I was an English

(25:34):
major and my statistics classes.
I believe I'll be able to share that, make it easier for your scientists in the field to
understand the grants.
And 30 minutes later, they told me that was the reason.
That was the answer because I could benefit their company that way.
Well, that's a common question for not only job seekers, but this is where it comes back to

(26:00):
startups.
Someone will say, well, let's just take job seekers as the example, because that's what
you used.
And let me say, well, do you have experience in this area and you may not.
And some people sort of, have an a, and they don't know how to answer that question,
but I think you can turn it into a benefit.

(26:23):
Frequently, you can say, yes, I have, I have not worked in this field, but let me tell you
the fields that I've worked in and why that is actually more important.
If I had all this experience in the field, I would frankly do probably a lot of the things
that either you're already doing or I will do things that are pretty traditional in this particular

(26:45):
area.
But what I can bring in is a perspective that may give us innovation because we can see from
other industries some of the things that you can effectively do here that differentiate you.
So if you, so I think if you like that story correctly, you can show that

(27:08):
that what was originally thought to be a deficit actually becomes a benefit.
Yeah.
And that comes from the confidence of listening to who your market or a job provider or whomever.
Whoever you're trying to sell.

(27:30):
And that's what we're doing when we communicate.
We're selling ideas.
We're selling, we're looking for not just money.
We're looking for alignment, approval, support, whatever.
And so we're selling ourselves to be able to get that thing.
It is really all about showing why what it is that you do is beneficial.

(27:52):
When we pitch, no matter what, when we tell our story, it needs to start with them.
So many people start, I do this.
Well, big deal.
You know, people don't necessarily think that you're more important than they are.
You need to get them to think about what it is that is either their problem or their opportunity.

(28:18):
You need to have them feel bad.
Once you do that, once you get them thinking about themselves or putting themselves in the
story, then all of a sudden you're in a situation where you can say, yes, you know, that pain you have.
I can, I can, I can eliminate it.
That fear you have, I can, I can, I can eliminate that.

(28:39):
The opportunity that you would like to get, I can help you achieve that.
So you need to have them think about themselves first.
I call it inverting the subject rather than starting out, I do this.
It's recognizing what's important to you.
And let me show you why I can be beneficial.
So I think that, that is important.

(29:03):
And keep in mind, we're trying to drive action.
We do not communicate to change what people know.
We communicate to change what people think and do.
That and find the action.
It's always a verb.
Before you go into any type of presentation, you have to understand what the verb is.

(29:28):
What do you want your audience to do?
I want you to fund me.
I want you to remember me.
I want you to move out of my way.
I want you to join me, whatever that happens to be.
Always a verb.
Identify the verb.
Identify what it is that you want your audience to do.
And don't be vague because if you're vague, your audience is going to be vague as well.
Can you give me an example?

(29:49):
Because I'm going to be pitching in January.
And it's at the Florida, I mean, future education technology conference.
And I want to win.
But I know that serves me.
It's not serving them.
So to do that, I would have to, I'm just listening to what you've been saying.
I need to think about, well, what does my audience care about?

(30:11):
They want to have a really good product that helps students be able to find internships.
So that my audience is educators.
And it could be customers because there will be vendors there.
So to show how I'm different is to be able to help explain how we can help your students get jobs quicker.

(30:36):
Well, keep in mind, it's a two stage process.
You've got to, you can't start by saying you're different if they don't know what you're different from.
Right.
So you really need to say, you know, here in the education field,
here is a challenge that we've had that we have not been able to address.
Or here's something in education that we haven't thought about doing because we couldn't do it.

(30:57):
And now we can.
So it is an opportunity to make things better.
So that's when you have to, that's where you start.
You start with making sure they know generally what it is that you do.
But then you go into the differentiation.
And I think that's, you know, frequently, how do you start?
There are five phase.
I discovered this 15 or 20 years ago.

(31:23):
And I haven't changed a word.
Every presentation needs to do five things.
It must start by capturing attention.
You've got to get people focused.
And sometimes you can do that with something provocative in the beginning,
or you can do a case study, a story.
And I'll come back to talk about that because I think those are really powerful

(31:46):
ways to get in.
So the first is, is you use is you capture attention.
Second is you engage your audience with content that is relevant.
The third thing is it you simplify, you make it simple and clear so they don't get it.
You don't overtell your story.
The fourth thing is you make it memorable.
You want them to go from short term attention to long term memory.

(32:10):
So you do something that creates this reason to continue to think about you.
And the fifth thing is much of drive action.
So those are five things that every presentation must do.
But let's go back to that attention thing.
How do you start?

(32:31):
Well, a lot of people start up, I say, my name is this and I do this.
And here's my background.
And by that point, the audience still has no idea why you're talking to them.
Sometimes we can start out with a case study.
And sometimes it can be an example of somebody who would be the beneficiary of what you do.
Here's Susie.

(32:53):
Here's Susie's problem.
Here's Susie's issue.
And or you use a case study of a client you've worked with or a problem you've solved.
Because what is very interesting, people will begin to either identify or empathize with whoever
that character is.
And sometimes they actually place themselves in the story.
You talk about a case study of solving a problem.

(33:16):
There's every likelihood that the person you're talking with has either had that specific problem
or it becomes a springboard for a problem that they have that now that you've touched on something
they can identify with.
Now, all of a sudden, there's a reason to begin to listen to you.
You've helped them identify.

(33:37):
You've aligned with them.
And now you can say, and here's the solution to that problem.
Always start with the problem or opportunity first.
Make because that's about your audience.
Establish that and then establish who you are.
Now, do I say this is a hundred percent of the time?

(33:58):
No, there's nothing that's a hundred percent.
But the best thing that you can be as somebody who is telling a story is
astute.
Part of it is the science of presentations.
Part of it is an art.
And what I work with people, what I'm trying to do is create their ability to look at any situation

(34:22):
and then know who the audience is, what's important to the audience,
and how to reach them with the appropriate content and not overtell their story.
So that at the end, you have picked their interests and one would hope
that you create an opportunity for the Q&A.

(34:45):
And we can talk about this in a bit, but I think the Q&A sometimes is more important
than the pitch and presentation that you deliver.
Let me tell you what.
The reason is because once they start asking questions, you know that they have engaged.
You learn the things that you weren't quite clear about so you can clarify.

(35:08):
You learn the things that, I mean, what happens is you learn as much in a Q&A
as your audience does.
I have a whole segment on Q&A because I think it is so important.
That is frequently where the decisions are made.
The decision to say thank you will be in touch maybe or I like that.

(35:36):
Let's have another meeting because keep in mind the goal of the first meeting,
especially in an investor meeting, is not to walk away with a check.
Nobody does that.
The only purpose of a first meeting is to get a second meeting.
And if you can keep that going because sometimes it takes four or five, eight,

(35:58):
ten meetings before you really get somebody alive, especially for funding.
You may have one or two meetings with somebody who is going to be a customer or client.
So set goals and sometimes that goal is give them enough to actually wet their appetite so that
they are going to call me back because they want to know more.

(36:19):
And in the presentation itself, sometimes you only have five or 10 minutes and you can't do
everything.
Lay the seeds for a question.
So something that will prompt them to ask you the question because now you're not answering it
in your time, that five or 10 minutes, you're answering it on their time.

(36:40):
I love writing about Q&A because most people really don't address how important it is
especially in a pitch to be able to really know you can anticipate the questions that you ask
and have a blow away answer.
You know you're asked the same questions all the time.
But like I say, lay the seeds for other questions.

(37:05):
So we're going to take a moment and acknowledge our sponsor, Cat5studios,
and we will be right back.
I'll insert that.
So Chuck, this was great stuff.
I took so many notes.
I only have three minutes for my pitch and there is no Q&A.
So I have to capture them right at the beginning.

(37:27):
That is all I have is three minutes.
Well sometimes people start with way too much runway in the beginning.
They use some kind of, when they use a story, sometimes it just goes on forever.
And then there's not enough time to deal with the important stuff.

(37:49):
What I think most people need, what everyone needs to do is understand what the time frame is
and what is going to be the most important to either discuss,
to discuss briefly, to a mention what stuff do you have to spend a little more time with.
With investor pitches generally have a number of categories that you need to deal with.

(38:15):
Marketing presentations have a number of things that you need to discuss,
including features and benefits.
And frankly too many people spend too much time on what the feature is,
the features about the product.
The real focus needs to be what is the benefit of that feature for that particular

(38:36):
audience. So three minutes is tough.
I coached a lot of people on three minute presentations.
The most important thing from the three minute presentation is you give them the big picture.
You can't give them all the detail.
You give them the big picture, you what they're appetite.
So it is very clear what you do and why it is important.

(38:59):
The most important question we answer, the most common question we get,
we get it all the time.
It is the most, and sometimes they say this in the presentation,
I say you walk into a room, you tell people who you are, you introduce yourself,
they know your name now or they see it on the name tag.
What's the first question you get asked, especially in the entrepreneurial space?
What do I do?
What do you do?

(39:21):
And I do this all the time to people.
I say what do you do?
And sometimes they tell me and it's highly technical and I glaze over because I'm another
technical person or I just got lost or they used a lot of jargon that I don't
understand.
And at the end, I want to say that's really interesting.
I only have one follow-up question.

(39:42):
What do you do?
So I think the answer, I think what people really want to know
is not how your gizmo works or the detail or the algorithm or any of the things that
are the how it works.

(40:03):
We want to start with why.
Why doesn't they do exist?
So the first part of that question, what do you do?
The first part of it says why do you deserve to be in the cosmos?
What is the problem you're solving or the opportunity that you're bringing?
Now have you done something that no one's done before or are you doing something that

(40:25):
someone's done before but you can do it better or faster and cheaper?
And I used to think it stopped there but there's a third thing which is really interesting.
And that is you may not be first.
You may not even have the best product but you have the best story.
And you know the example I use in workshops and that is if people are old enough to

(40:47):
have this is we all have a closet filled with old video cassettes.
Probably VHS.
VHS and beta came out at the same time beta was much better but VHS,
folks who made that had a better story.
They knew the market better.
They were more responsive.

(41:09):
That's why they, not the better product became the pretty much standard.
So the first part of this, what do you do is why do you deserve to be in the cosmos?
The second creates the story because the second part of it is why should your audience care?

(41:32):
That you can find out based on the research you do, based on just knowing who your audience is,
putting yourself in their shoes.
What is important to them?
How do they think?
What is the lens that they need to see you through?
And then the third element people often forget and that is what's the ask?
Okay, now that we understand each other, what do we do next?

(41:55):
How do we work together?
What should I do to provide you with that next step?
So why deserve being the cosmos?
Why should your audience care?
What do you do next?
That's the answer to the question.
What do you do?
That's all good stuff here.

(42:16):
So Chuck, what do you think the future of entrepreneurship is going to look like?
We can deal with it with the state of it now, but with AI and automations,
everything blew up.
What do you think?
Well, the 2030, by the way, 2030.
We're going to be talking about now versus 2030, whatever your thoughts are.

(42:41):
I'm not good enough to know what's going to happen
five or 10 years from now.
I can guess, but things change so quickly.
So I don't think I can give people tools that they can use in the next six years.
I can give them guidelines to say, here's how you can respond no matter what happens.

(43:05):
So I think that is, I don't know what's going to, what I do know is it's going to continue to
be competitive.
What I know is innovation is going to continue because people have really, really great ideas.
I know it's going to be difficult.
Some types in the economy, it's much more difficult than others.
We have to be aware of what the technology is going to do.

(43:29):
AI is out there.
I've got mixed feelings about it.
I see its benefits.
And I also see that it's doing some damage.
We can't trust reality as much anymore.

(43:50):
There's a lot of things that, I mean, we used to say, oh, I saw it on the internet,
so it must be true.
Well, it's even worse with AI now because AI sometimes gets it wrong.
I've defined AI early on.
Well, first of all, early on, I was really skeptical and I thought AI is going to rise
up and kill us all in our sleep.
So I'm a little less concerned about that though I'd still see some of the

(44:14):
possibilities of doing things that are bad or to be not comfortable.
But the way I've described AI because it's not always accurate is it is like a very eager
and enthusiastic assistant who is an imbecile who just makes mistakes.

(44:38):
So what you have to do, obviously with AI is trusted.
But let me go one step further.
People who use it as the end product, I think, are, first of all, it's not their thoughts.
It's not original.
It could even be plagiarism.
So you need to find your voice.

(45:00):
But what you need to do is, number one, you need to verify because it could be wrong.
But the other thing that's more important is you need to put it in your own voice.
If you're writing, let it do the research.
Let it be the assistant.
Let it even do a first draft if you want it, but you need to go in and put it number one in your

(45:23):
voice and number two, make it sound like it's not AI.
I mean, there are AI detectors all over the place.
I'm teaching at college.
And what I see, it's a very significant problem in academia right now,
is a lot of the students are using AI and not citing it as using AI.

(45:48):
And that's going to be a problem.
The other problem that I see is this wonderful skill of writing.
If we rely too much on AI, I think we're going to lose the ability for people to really
write well.
I'm still old school.
I'm at the keyboard all the time, and yes, I'll use AI, but I use it very sparingly.

(46:13):
I think still the best ideas come from humans.
I think, yes, let AI make connections and pull in things that you might not think about.
But it ultimately has to filter through you.
And that's the beauty.
I don't think AI tells a good story.
I'm a story guy.
I think stories come from us.
We're story animals.

(46:35):
You know, we have been since we sat around fires and caves.
That's how we learn when we're free language or just barely post languages as toddlers.
Much of what we learn is through the stories that our parents tell us.
So, story has been with us forever.

(46:57):
And I am sometimes disappointed that people don't understand what its power is because
they take it for granted.
So, my job right now is to say, here is the power of story because it may become one of

(47:20):
your greatest assets because it is the connection between you and those you're trying to reach.
We've got to stop telling our story from the inside out.
We're this.
Pay attention where this is what we are.
Take a look at that.
No, we shouldn't tell a story from the inside out.
We should tell it from the outside.

(47:42):
From the perspective, we understand who our different audiences are.
And we give them the lens.
So, you don't change.
Who you are doesn't change.
But the lens that we give people to see us, to oughta be a reflection of what's important to them.

(48:03):
How we answer their needs.
How we provide them with opportunities.
You know, decisions are not made in the cognitive part of our brain.
And that's why people who slather their decks presentations with just bunches of facts don't
win their audience over.
We need to understand what we want our audience to do first and what is important to them.

(48:30):
So, the first level is what do we want them to do?
The second level is what do we need them to think or feel in order to make them experts know,
but in order to get them to do what we want them to do.
And then the third level is now what is the contact content that we need to make them experts?

(48:53):
No, to tell them everything?
No.
It's to get them to think
either differently or to reinforce the way they're already thinking if that's what we want them to do.
Because that thinking, that feeling is the thing that's going to drive them to some kind of action.
So, I think that's and I've something in the book called the Z chart that actually shows step by step

(49:19):
how you get to the right content.
And I think that's important.
Content is important, but intent must start before content.
You know what's funny is that it struck me a while back that when we go into formal education
we're taught to conform and you know because it was to scale right we have all of these

(49:44):
kids that we're putting through.
So, we need everybody to behave the same way act the same way read the same stuff.
So, it's always about unifying and just conforming.
But once you go away to college and you still have that mentality, but they don't prepare you
how to be different, how to differentiate.

(50:06):
So, I feel like a lot of what you're teaching you're talking right now in your book, it really
is something that has not been taught until we get into a either business for ourselves.
And even still, I don't feel like how we differentiate has been the

(50:27):
highlight of some of the programs that I've been in.
And I feel that your book is really valuable and what you're teaching is valuable for that
reason because when you get you're looking for the job, the ability to differentiate and say,
hey, this is how I do this, or this is how I think is key.
I've been on both sides.

(50:52):
I've been in academia and the real world.
I spent more time in the real world.
I started out in academia and now I'm sort of going full circle because of the professorship
that I was just offered.
And but the reason I was offered it is because they like the content of the book and they want
now to embed that in their curriculum.
So, I'm trying to get more and more colleges, universities, and accelerator programs to

(51:15):
adopt this model because it has been very effective.
But here's the issue in education is we're taught to be subject matter experts.
We're not necessarily taught how to communicate what it is that we know and do
so that other people understand it.
So, we're taught to be subject matter experts, but not how to communicate what it is that we know.

(51:40):
So, that becomes my job.
That's my role.
Like I say, I'm not a technical person.
But here's the weird thing.
I have not found a technology, an idea that is so complicated that it cannot be explained
on some level very simply.

(52:04):
Like a five year old, explain it to a five year old.
Well, yeah, to a degree, but it is understand who your audience is.
If it's a five year old, then that's how you tell it.
But if it's a professional person, you still must explain it in the way that you can explain the basics.

(52:26):
I have a really another program.
I run a six week or seven week, I've got two versions of it masterclass
on this strategy and story.
And it's been a major game changer for literally thousands of companies.
I love what I do.
The book is based on the model that I've been teaching forever.
And that's a longer class, but I have a short class now.

(52:51):
Three hours, specifically for people who are technical.
And I think you'll like the name of it.
It's called teaching technical experts to speak to mere mortals.
And it is, I mean, that's a challenge that I see because especially technical
technical people, and I don't want to overgeneralize, but I kind of will.

(53:13):
They're taught to think about detail and precision and solution, where I think the
non-technical audience, and these are often the decision makers, need to know not necessarily
all the detail, they need to know the big picture.
If you tell them some of the features that you have, make sure that it's backed up by a benefit

(53:39):
to benefit is about them.
It's not about how you do things.
It's why you do it.
And it's not about the data.
It's the consequences of the data.
So if I can just change these four things in people who are technical,
all of a sudden now they can still reach their peers.

(54:00):
But also reach people who are not technical, who might get lost in the jargon,
because they think in a way that is different from the technical people, and they are far
further away from the detail, the content, the technology.

(54:22):
Now where that differs is if your audience is already up to speed, and they are already
very technical.
You still want to start by saying why you're doing it.
But then once that, you're on the same page, and now you can go into the detail,
even with technical people who do want to know more about how the GISMO works, how it's wired,

(54:45):
what your algorithm is.
But once again, it really always comes down to know your audience, and people who do that.
And the other thing, the other thing I want to point out in the time we have left is
be authentic, be yourself.
Don't be overly scripted.
Talk to your audience.

(55:07):
This is not public speaking, this is not oratory, this is a monologue that should turn into a dialogue.
Be yourself, and never memorize your, what a horror story is.
I was doing a, I was judging a program at MIT, and these were graduating students

(55:36):
who had come up with a concept, an idea for entrepreneurship.
And they had five minutes to pitch to investors and mentors like me.
And I was one of the people who was to make some comments about it.
And most of the people did a, you know, an adequate job.
We understood what it is that they do.
One poor guy was so focused on not forgetting anything that he wrote everything out and then

(56:06):
memorized them.
Well, first of all, he came across as very stilted, very difficult.
He was, he was delivering words and not phrases and feelings.
He got about 30 seconds into his presentation, and he forgot what the next line was, and he froze.
You know, deer in the headlights.
And it seemed probably seemed like hours for him that he was standing, not knowing what to say.

(56:31):
And you know what he ended up doing?
He started from the beginning.
So he finally got through it.
I talked to him afterwards and I said, you know, don't memorize.
Don't, I know you thought you would be more confident that way, but it showed the
way, but it showed that you weren't confident.
He said, you know more about the subject than most of the people in the room.

(56:52):
Be confident about that.
Be yourself if it's if it's stammer.
So what?
Be authentic.
They are buying you, not just your technology.
And this happens all the time.
And you'll find this in your entrepreneurship that there are a lot of ideas in ed tech.
They're going to buy it not just because your idea is a good one,

(57:15):
but because they have the confidence that you can pull it off.
And where does that confidence come?
The only place they see it was standing in front of them.
So, you know, I think all these things are important.
I see a lot of companies that succeed.
I see a lot of companies that fall during, in fact, most of them, most startups don't succeed.

(57:38):
But I'll tell you, if you've engaged your audience, if you've connected, if you've aligned,
if you've said something that takes their curiosity, if you have something that is memorable,
whether you start with that thing or end with it, then you're going to be remembered.
Remember, start strong.
Start with a story.
Start with a provocative attention getting statistic and end strong.

(58:04):
Don't, you know, invite them to participate.
Have some strong phrase at the end that is memorable.
So, start strong and strong.
Starting strong is really important.
I was working with a woman who was an ophthalmologist.
She and her team had come up with this really, really highly sensitive test for those things

(58:31):
that lead to vision loss.
You know, glaucoma, macular degeneration, things like that.
And she started out in a traditional way saying, this is the test and here's the,
it works with the gold.
It's better than the Goldman device that we've been using.
And here's the statistics, but here's the things, the data behind it.

(58:56):
And except for our ophthalmologists in the room, she was losing people.
So I was looking at her deck and buried in her deck was this little one line thing.
And it was in the end that she sometimes ignored it.
And the line was, by the end of life, one out of four people will be blind.

(59:19):
And I said, that's your opening.
It grabs people's attention.
And now you can say the reason is that we do not catch those things that cause blindness early enough.
We have a technology that is much more sensitive than anything here that can.

(59:40):
And then she went on to that.
So remember, your audience is so important.
Try to find something that makes you memorable, that reaches them,
that gets them to sit forward and say, okay, tell me more.
That's part of the title of my book.
It's getting people to listen like you and say, tell me more.

(01:00:01):
That's what you do if you want to engage people and have a really important second step.
This whole show has been immensely filled with just so much wisdom and nuggets.
We're at the end and we have just a few minutes, but what's the best mentoring advice that you
want to share with our listeners?
I know you've been talking about the present, but it also applies to the future.

(01:00:26):
So best mentoring advice.
I've done a lot of mentoring.
I've met literally thousands of companies as a result of doing office hours and having meetings
and judging and coaching.
When you sit down with somebody, first of all, find the right mentor and be selective,

(01:00:50):
because not everybody's going to be the right mentor.
Find somebody who is going to be what you think is effective, but be coachable.
Now, I always say just because I'm a mentor and have experience doesn't mean I'm always right.
You've got to make that decision yourself, but let me try to convince you why.

(01:01:13):
So the worst people I deal with are people who
go in and come out with exactly the same ideas because they're not listening even to,
if it's not a great idea.
So you need to be coachable.
You'll also find that so much of the support that you get

(01:01:36):
will be from peers.
Entrepreneurship is interesting.
Yes, it's to a degree competitive, but I see more support.
I'm doing something now.
I'm running a global entrepreneurial roundtable that I will actually invite your listeners to join.
We do it on Wednesdays. It's virtual.
We've had a thousand people in our network.

(01:01:57):
We have 15 to 30, 35 people each week join us online,
and most of the conversation is about how people are helping each other.
It's about general concepts and entrepreneurship.
It's here challenges that you can bypass.
Here are problems that you can circumvent.
Here are some best practices.
That's your problem.

(01:02:18):
I've gone through that before.
Let me tell you how we got out of it.
So it's really quite fascinating.
So it's trucks roundtable.com, that simple.
And maybe we can send out some information on that, but you'll meet extraordinary.
We've had over 15,000 connections, collaborations, job leads, opportunities.

(01:02:43):
So that is my second favorite thing to do.
My first of these workshops that I do, these six-week programs meet once a week, virtually.
And we go through this step by step.
So I can see at the end people absolutely transforming,
because now they're not just subject matter experts,
but now they have the tools to communicate what it is to make it seem important to others,

(01:03:09):
because unlike other people who are pitching, these folks are no longer amateurs.
They really know how to engage and monitor an audience as they're presenting.
So it comes down to story.
My five pillars, strategy, it's your content, the right content for the right audience.

(01:03:33):
And you figured that out in your strategy.
It's the right visual support, because when we pitch,
we use things like PowerPoint.
And I wish we had another hour.
I would talk about why PowerPoint is being used in effectively.
We're creating too many slides that are way too complex.
So the fourth pillar is delivery, how we deliver naturally in the fifth is follow-up,

(01:03:59):
because it's just as important as the initial strategy.
So that's what I'm trying to teach people.
And it is the biggest joy.
I love doing it.
It never, never gets old.
So again, I'm not going to be able to write your term sheet.
I'm, if you have me code your app, it's going to crash.

(01:04:21):
And once again, if I'm a pilot or a traffic controller,
that your life is going to be worthless.
But what I want to be able to do is help people.
I'm frequently labeled a storyteller.
And yes, I do.
I have all kinds of writing that I do.
But what I see as a more important job is being a story catalyst,

(01:04:44):
helping people find their story, helping people find their voice.
And if I can do that, I will retire at some point in my life maybe,
but I won't do it.
Quite satisfied and happy that I was doing things that
really had some level of impact.
Well, Chuck, it's been really delightful to have you here on the show today.

(01:05:08):
I want to thank you so much.
I'm very excited about publishing it.
I will include the links to your book on Amazon and also the round table.
I did ask to join it, but I had to unsubscribe from some other groups.
And I feel your group was worth that.
So I did.
And I am very excited about continuing to learn from you and also hopefully be able to contribute

(01:05:34):
value too.
Well, like startups do it because they love what they're doing.
And they think they can have impact.
And maybe it's like that for most of us who really want to do something that we love.

(01:05:55):
Well, thanks so much.
I will see you in Boston whenever I come up there.
Excellent.
Thank you.
We want to thank our sponsor Cat5 Studios and thank you to our video production and editing team.
And music is by Sophie Lloyd.
The interim whispers brought to you by employers for change,

(01:06:16):
helping hiring teams to recruit and upscale interns to employees through
mission, values, beliefs, and core skills.
Learn more about it at www.e4c.tech.
Subscribe to the intern whisperer today and show your support by sharing our show,

(01:06:37):
tagging a friend and leaving us comments.
And be sure to go and follow up with all of our great guests.
Thank you.
And Boston, when you were doing the prepare for VC program,
which I've been a supporter of prepare for VC, been a sponsor for a number of years.

(01:07:00):
I'm really impressed with what it is that they do.
That's good to hear.
I love those guys.
I like them.
When I say I love them, I love them.
You know, like they've been so helpful.
They've been really good people to work with.
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On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

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