May 27, 2025 • 5 mins
In this episode of The Briefcase, Dan Cashman reflects on the decision to end The Nite Show, the nation’s last locally produced late-night talk show, after a 15-year run. He explores the emotional and strategic complexities of knowing when to let go, whether in media, business, or personal projects. From pandemic pivots to long goodbye planning, Dan shares lessons on flexibility, gut instinct, and making peace with transitions. He offers valuable insights for entrepreneurs and creatives navigating change.
You’ll learn how to:
-
Trust Intuition in Leadership Decisions
-
Navigate Transitions with Grace and Strategy
-
Balance Passion Projects with Practical Realities
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
(Transcribed by TurboScribe.ai. Go Unlimited to remove this message.) When do you know it's time to let
it go?
I think in a case like this, you
need to trust your gut.
This is The Briefcase from Sutherland Weston Marketing
Communications.
Quick conversations from everyday observations delivering practical marketing
ideas you can carry with you.
(00:20):
I'm Dan Cashman, Public Relations Director at Sutherland
Weston.
And you also have for years and years
and years been the host and producer and
editor and bottle washer of The Night Show.
Yes, it's been a passion project for sure.
Airing on all three markets in Maine.
And I was surprised to learn, and I
think many were, that it was the only
locally produced late-night talk show in the
(00:42):
entire United States of America.
Some have come and gone through our tenure,
and there were certainly some that existed before
us.
But I believe the last one that went
away was called Tonight in San Diego in
San Diego, California.
They were running on the CW affiliate out
there.
And it is no more.
I'm still friends with the people that hosted
it.
It was a wonderful production.
But now yours has gone away.
(01:03):
True.
15 years is a pretty long shelf life
for a local television program.
And it really was a labor of love.
And for all of us that were involved,
we have other responsibilities and jobs.
Let me draw upon your experience as a
host and a producer of a television program
as a person that helps manage PR for
so many businesses and your business background and
(01:25):
ask you this.
When do you know it's time to let
it go?
I think in a case like this, you
need to trust your gut.
Jerry Seinfeld, towards the end of Seinfeld, said
that in comedy, timing is everything.
And I certainly would not call myself a
comedian.
In fact, comedians would bristle at that.
But I do think that timing is everything
(01:46):
when it comes to a lot of things,
television, business, relationships.
And sometimes you have to trust your gut
on that timing.
Sometimes you'll get it wrong, but other times
you'll know it.
And in this case, I knew it.
When you dreamed up your show, it was
the equivalent of someone writing a business plan.
And it has to be flexible.
I'm sure you were flexible with the way
(02:07):
that you produced the night show.
Absolutely.
We had a relationship with the New England
School of Communications at Huston University and a
relationship with the TV stations.
And those really were the only elements that
needed to be strong pillars.
Everything else was flexible.
But when you have a business plan, you
cling to it if you're wise.
(02:27):
And that might prevent you from letting go
when it's time.
I think that's true in many cases.
But I think, especially in Maine, a business
plan is worthwhile.
But the person behind the business plan or
the people need to also recognize that sometimes
you must be nimble.
Every business plan in 2020 with COVID went
out the window.
With the night show, we started shooting the
(02:48):
show in my basement.
And I say we, I mean I, because
nobody could get together.
In order to survive that period of time,
everybody had to be nimble.
And that is true in so many other
small ways as it relates to personal stories
with people in business.
Now, another parallel.
You're a business owner.
You know it's time to let it go.
The people that you just mentioned, the students
(03:08):
from the New England School of Communications, those
who have partnered with you all of this
time, they are the equivalent of your employees.
And that complicates the decision.
Absolutely.
The relationship with NESCOM and HUSN has grown
over time.
And so I have a real fondness for
the faculty and staff and administration and absolutely
(03:30):
the students, current and alumni, who have gone
through that program.
And it was important for me, and I
think for planning, to have a long runway
for this program to say goodbye.
So we announced it in February of 2024
and it ended in May of 2025.
That's a 15-month runway to kind of
figure out what the program can do next,
how we're going to close it up appropriately.
(03:51):
That's not an appropriate runway for everybody.
And in fact, I was criticized from a
lot of friends of mine for taking that
long.
They said, why don't you just say goodbye
and close it up?
It couldn't work that way.
And so the parallel is if you're a
business owner, if your heart and your gut
are telling you it's time, plan the length
of that runway for your employees and for
your vendors.
If you're a sole business owner, only you
(04:13):
know the business as well as you do.
So if you need to take that time,
if you say to yourself, we're going to
close up shop, but it's going to take
15 months to do so, you're really the
only person that can know every single possible
thing that goes into that decision.
So if your gut tells you to do
it that way, do it.
But at the same time, make it public.
I had some seller's remorse when I decided
that the show would come to an end.
(04:34):
And if I hadn't announced it publicly, we'd
probably still be doing the show today.
I wonder if there's a final parallel.
And that is now that you are done
with this chapter, you have opportunities ahead.
You could do this.
You could do that.
If a business owner is seeing that, okay,
it's time for a change while I will
have a period of mourning, I can look
now to other opportunities.
(04:54):
I think that's fair to say.
And I think it really depends on what
the business's goals are and what your own
personal goals are.
And if you're a business is one that
employs 300 people and is making money hand
over fist, then maybe it's not closing up
the business.
Maybe it's selling the business.
Everything is a little bit different, but I
think it all comes back to trusting your
(05:15):
gut and not having it be an impulsive
decision.
Think it through, trust that gut reaction and
kind of see what the pros and cons
are of every possible scenario.
I think the big difference is Ron's Romantic
Supermarket is now closed and closed for good.
And at least with the night show, we
get reruns.
It was Ron's Romantic Supermarket, wasn't it?
Dave's.
(05:35):
Boy, you remembered that quickly.
I think we're done here.
You have been listening to The Briefcase from
Sutherland Westin Marketing Communications.
Got a question for the Sutherland Westin team?
Email us at SutherlandWestin.com.
(Transcribed by TurboScribe.ai. Go Unlimited to remove this message.) When do you know it's time to let
it go?
I think in a case like this, you
need to trust your gut.
This is The Briefcase from Sutherland Weston Marketing
Communications.
Quick conversations from everyday observations delivering practical marketing
ideas you can carry with you.
(00:20):
I'm Dan Cashman, Public Relations Director at Sutherland
Weston.
And you also have for years and years
and years been the host and producer and
editor and bottle washer of The Night Show.
Yes, it's been a passion project for sure.
Airing on all three markets in Maine.
And I was surprised to learn, and I
think many were, that it was the only
locally produced late-night talk show in the
(00:42):
entire United States of America.
Some have come and gone through our tenure,
and there were certainly some that existed before
us.
But I believe the last one that went
away was called Tonight in San Diego in
San Diego, California.
They were running on the CW affiliate out
there.
And it is no more.
I'm still friends with the people that hosted
it.
It was a wonderful production.
But now yours has gone away.
(01:03):
True.
15 years is a pretty long shelf life
for a local television program.
And it really was a labor of love.
And for all of us that were involved,
we have other responsibilities and jobs.
Let me draw upon your experience as a
host and a producer of a television program
as a person that helps manage PR for
so many businesses and your business background and
(01:25):
ask you this.
When do you know it's time to let
it go?
I think in a case like this, you
need to trust your gut.
Jerry Seinfeld, towards the end of Seinfeld, said
that in comedy, timing is everything.
And I certainly would not call myself a
comedian.
In fact, comedians would bristle at that.
But I do think that timing is everything
(01:46):
when it comes to a lot of things,
television, business, relationships.
And sometimes you have to trust your gut
on that timing.
Sometimes you'll get it wrong, but other times
you'll know it.
And in this case, I knew it.
When you dreamed up your show, it was
the equivalent of someone writing a business plan.
And it has to be flexible.
I'm sure you were flexible with the way
(02:07):
that you produced the night show.
Absolutely.
We had a relationship with the New England
School of Communications at Huston University and a
relationship with the TV stations.
And those really were the only elements that
needed to be strong pillars.
Everything else was flexible.
But when you have a business plan, you
cling to it if you're wise.
(02:27):
And that might prevent you from letting go
when it's time.
I think that's true in many cases.
But I think, especially in Maine, a business
plan is worthwhile.
But the person behind the business plan or
the people need to also recognize that sometimes
you must be nimble.
Every business plan in 2020 with COVID went
out the window.
With the night show, we started shooting the
(02:48):
show in my basement.
And I say we, I mean I, because
nobody could get together.
In order to survive that period of time,
everybody had to be nimble.
And that is true in so many other
small ways as it relates to personal stories
with people in business.
Now, another parallel.
You're a business owner.
You know it's time to let it go.
The people that you just mentioned, the students
(03:08):
from the New England School of Communications, those
who have partnered with you all of this
time, they are the equivalent of your employees.
And that complicates the decision.
Absolutely.
The relationship with NESCOM and HUSN has grown
over time.
And so I have a real fondness for
the faculty and staff and administration and absolutely
(03:30):
the students, current and alumni, who have gone
through that program.
And it was important for me, and I
think for planning, to have a long runway
for this program to say goodbye.
So we announced it in February of 2024
and it ended in May of 2025.
That's a 15-month runway to kind of
figure out what the program can do next,
how we're going to close it up appropriately.
(03:51):
That's not an appropriate runway for everybody.
And in fact, I was criticized from a
lot of friends of mine for taking that
long.
They said, why don't you just say goodbye
and close it up?
It couldn't work that way.
And so the parallel is if you're a
business owner, if your heart and your gut
are telling you it's time, plan the length
of that runway for your employees and for
your vendors.
If you're a sole business owner, only you
(04:13):
know the business as well as you do.
So if you need to take that time,
if you say to yourself, we're going to
close up shop, but it's going to take
15 months to do so, you're really the
only person that can know every single possible
thing that goes into that decision.
So if your gut tells you to do
it that way, do it.
But at the same time, make it public.
I had some seller's remorse when I decided
that the show would come to an end.
(04:34):
And if I hadn't announced it publicly, we'd
probably still be doing the show today.
I wonder if there's a final parallel.
And that is now that you are done
with this chapter, you have opportunities ahead.
You could do this.
You could do that.
If a business owner is seeing that, okay,
it's time for a change while I will
have a period of mourning, I can look
now to other opportunities.
(04:54):
I think that's fair to say.
And I think it really depends on what
the business's goals are and what your own
personal goals are.
And if you're a business is one that
employs 300 people and is making money hand
over fist, then maybe it's not closing up
the business.
Maybe it's selling the business.
Everything is a little bit different, but I
think it all comes back to trusting your
(05:15):
gut and not having it be an impulsive
decision.
Think it through, trust that gut reaction and
kind of see what the pros and cons
are of every possible scenario.
I think the big difference is Ron's Romantic
Supermarket is now closed and closed for good.
And at least with the night show, we
get reruns.
It was Ron's Romantic Supermarket, wasn't it?
Dave's.
(05:35):
Boy, you remembered that quickly.
I think we're done here.
You have been listening to The Briefcase from
Sutherland Westin Marketing Communications.
Got a question for the Sutherland Westin team?
Email us at SutherlandWestin.com.
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