Matthew Reustle - CEO of Colossus

Matthew Ruestle, CEO of Colossus, sits down with Ryan to walk through his career, discuss his approach to growing a media platform with highly-successful podcasts like Founders, Invest Like The Best, and Business Breakdowns, and to talk about his perspective on hiring and being hired.

Connect with Matthew on LinkedIn: https://www.linkedin.com/in/matthew-reustle-cfa-255874b/

Listen to shows by Colossus:

Founders: https://podcasts.apple.com/us/podcast/founders/id1141877104

Invest Like The Best: https://podcasts.apple.com/us/podcast/invest-like-the-best-with-patrick-oshaughnessy/id1154105909

Business Breakdowns: https://podcasts.apple.com/us/podcast/business-breakdowns/id1559120677

Episode Transcript

(00:00):
[MUSIC]

(00:02):
Welcome to the GoodFit Careers podcast where we explore perspectives on work that fits.
I'm Ryan Dickerson, your host.
Today's guest is Matt Reustle.
Matt is the CEO of Colossus, the content platform behind the Founder's podcast, invest like
the best and business breakdowns.
Their podcasts have over 100,000 followers on Spotify with 2 million downloads per year

(00:27):
and nearly 100 million downloads in the company's history.
Matt started his career in financial services.
He was an intern with Lehman Brothers in the summer of 2008, an analyst with Barclays
through the financial crisis, and he spent nine years with Goldman Sachs working his
way up to lead equity analyst focused on transportation activities.

(00:47):
Matt spent two years as vice president and Raven Capital Management before joining Colossus
in 2021.
Matt, thank you for being here.
Great to be here.
Thank you for having me, Ryan.
We're delighted to have you.
So to kick this all off and to get us started here, would you tell us a little bit about
your work today?
Sure.
So currently I am the CEO of Colossus, which is essentially a media organization created

(01:12):
for professional investors where you see us most is our audio podcast, invest like the
best founders, business breakdowns, art of investing, making markets.
We have a select group of shows that we produce weekly and we shipped our audience.
We also have some other forms of media.
We write a newsletter.

(01:33):
We do some stuff with the website, but really it's work around that and building up the
business from the audio foundation and seeing what we can do with it from here.
We'll dive deeper into the work you do in a little bit here, but to build our frame of
reference, would you tell us a little bit about what you were like as a kid?
Sure.
So childhood for me was that, which seems probably very normal for people growing up

(01:58):
in the Northeast, a lot of sports.
I was analytical and interested in a lot of things as a child.
Maybe I didn't always show up in the report card.
So I think one thing I think back to in my early days was being high potential, but never
quite meeting that potential and not really figuring it all out and putting it all together

(02:19):
until I got to college, which I think is actually quite common for entrepreneurs.
I wouldn't necessarily bucket myself as this diehard entrepreneur, but some of the characteristics
that I think you see in these stories, there's some similarities to what my childhood experience
was like.
And then once I got into college, that's when I maybe started to put things together,

(02:40):
where there's a little bit more focus on the output and the grades and a little bit more
concentration in terms of what I was spending my time in rather than being so scattered
and so interested in the many different things out there in the world that can take up your
attention.
Sure.
So you figured it out in college and then maybe found your true calling 10 years into
your career or 15 years in.

(03:01):
Did you have a clear sense of what you wanted to be when you grew up when you were a young
person?
I would know.
I would say I was not the person that was investing in stocks at age four and then goes
on to be a portfolio manager.
I think there were certain things that I was interested in from a very early stage math.
My father was an engineer.

(03:21):
I always appreciated math and that there was a set answer that could not be argued over.
Once you get into the verbal realm, I think I was always interested in people and the psychology
of people, the psychology of markets, what drives them.
But I wouldn't say that writing or anything along on that side of the spectrum was necessarily

(03:43):
my calling.
It wasn't until I got to college and I was figuring things out.
Do I want to go to a law school or do I want to go into some other fields that I had my
first economics class?
I thought, ah, this is a perfect blend of the two things that I enjoy the most.
It was very natural and easy for me to understand.
And that really clicked along with joining in student organization, the Madison Investment

(04:07):
Fund, which was a game changer for me where it put me in an environment with other students
that were very interested in markets where my small interests really started to grow,
just being in that type of environment and getting basically into the world of finance,
which really fascinated me the more and more time I spent on it.

(04:27):
So it was those two things combined that made me set out to launch a finance career, which
I did for many years before transitioning over to classes, which is an extension of
the finance career, but certainly different in many ways.
But it was that college experience that really put the light bulb over my head.
I very much so agree with that economics, kind of being that aha moment.

(04:49):
I went into school having no clue what I wanted to do.
I went to a Syracuse with a really broad range of options.
And that first economics class I was like, ah, here we go.
This will do.
Yes.
Yeah, it's nice when you can have that experience and then you're seeing others around you,
aren't necessarily having that experience.
Maybe some people were, it wasn't clicking as much for them.

(05:11):
And that to me, for whatever reason, was also a signal of, okay, you know, this is something
that not everybody loves it either.
So that there might be something here.
And you were in college right before the financial crisis.
If I understand it correctly, you got to be an intern at the Lehman Brothers in the summer
of 2008.
What was that actually like?
Yeah, it's a story or a thing on the resume that gets better with age, I think, as time

(05:34):
goes on, you reflect on it and you put yourself in that moment.
But it was very interesting.
I mean, even leading up to that, going through the internship process, I was studying abroad
at the time and doing these interviews in internet cafes at the time.
We didn't have the technology that we did today.
So I'm stuffed in this little box, trying to answer brain teasers and all these analytical

(05:55):
questions and basically fighting to get opportunities on Wall Street where James Madison wasn't necessarily
a target school.
So you had to go outside the box in terms of creating those opportunities for yourself
and landing at Lehman summer of 2008.
Little did I know what I would get to witness, but it was a very interesting experience where

(06:17):
I would like to say many times you don't know what's going on in the moment, but there was
a feeling here that there were major potential changes to the entire economic universe.
Bear Stearns had already collapsed and we were, you know, these essentially students that
were shielded from a lot of what was going on.

(06:37):
You got this taste of the good days and Yankee games and restaurants, but then you saw the
stress on a lot of people, particularly having an earnings announcement in the middle of our
internship and then ultimately showing up with 32 interns, the expectation that they
keep 90 to 95% of interns.
That number was 50% for us and it even shrunk beyond that once Lehman filed bankruptcy

(07:02):
in the middle of September that next year.
So it was one of those things where I was fortunate.
It was not going to completely change my life in the way that it did for many, but I still
got to witness what things can be like when all of the confidence in the system gets lost.
Having that I think shapes you in a way which is really hard to create otherwise.

(07:24):
So it's always stuck with me to remember what that environment was like, what the fear was
like, what the living in the unknown and somewhere deep inside of my brain that sticks around.
I imagine that was so fascinating and builds such a great intuition on what the top feels
like, what that crest over the top feels like and then what the beginning of the no-gravity
moment kind of feels like.

(07:45):
Yes.
Yeah.
I think what was interesting is coming back.
I joined Barclays for a short period of time after graduating and Barclays had purchased
Lehman Brothers division that I was based in and even then it still felt so uneasy and
we were off the bottom which was the March of that year.

(08:06):
It didn't feel like that honestly for several years.
The lingering effects of that type of shock don't go away for a while and it's hard to
think about that now in such a completely different environment, but it sticks with you.
All right, Bette, that summer I was in Shanghai.
I was doing a summer abroad program and getting to watch, essentially we were studying international

(08:27):
finance and watching that from Asia was so fascinating.
The perspective was so different.
And I imagine that whole perspective on we hit the bottom.
I was working at Barclays.
I was a full-time employee, but nobody really believed it was actually the bottom.
I mean, that's an amazing experience.
Yeah, it sticks with me.
I'm sure Shanghai was quite a time.
The Beijing summer games were there.

(08:49):
That summer.
Yeah, yeah.
Yeah, that was one heck of a summer games.
So that must have been a pretty neat experience to get.
It was awesome.
So to give us a little bit of perspective on landing that first full-time job, can you
walk us a little bit through the actual hiring process and what your experience was like?
So first full-time job was Barclays.

(09:12):
And this came from again, we had 32 in our intern class, 16 got offers, only eight got
offers from Barclays.
So it got shrunk down significantly.
And it was somewhat of a hodgepodge of an experience because the team that was bringing
you on was still very much integrating into a new business.
So they were essentially joining a new business themselves.

(09:34):
And that creates some interesting nuance to what would otherwise be traditional onboarding.
And I think what I realized was many of the groups that I was interested in being in weren't
purchased by Barclays.
This was not necessarily the right fit for what I wanted to do.
During my internship experience, I had gone through the process with Goldman Sachs, actually
had good opportunity with Goldman Sachs, chose Lehman Brothers.

(09:57):
We can talk about my decision-making.
But what I did through that was stay in close touch with the people at Goldman.
And what happens in these cycles is when you do have internship classes where you don't
hire many of the students, if you then come back and see a rebound, you've underhired.
So there is a need to bring on new people.
So it was about 10 months into my first year that I moved over to Goldman.

(10:21):
And the experience of that was staying in close touch with people just because you haven't
accepted something doesn't mean there has to be a bridge that's burned.
And ultimately keeping those options open, keeping that network working throughout that
period of time, paid dividends.
And I think that could have happened years down the line.
It just happened to happen very early for me in my experience.

(10:41):
So Goldman sounds like the space where you hit your stride.
You found your home and financial services.
You were promoted several times.
Can you tell us a little bit about what you carry with you today from the Goldman experience?
Certainly.
So I think there you have a group of people that are all used to having massive amounts

(11:01):
of success way beyond my imagination, from my levels of success early on in my life.
So you're getting into an organization with people that have accomplished things, people
that are not used to being anything but number one in whatever that they're doing.
So that has some type of impact on the environment that you're in.
One, you are just working around great people.

(11:23):
And I think what impressed me the most was you were ultimately graded based on the work
that you were doing.
And if you got opportunities, which didn't come for everyone, but if you got opportunities
and you took advantage of those opportunities, you presented well, you delivered whatever
needed to be delivered in that moment, then you would quickly move up the chain in terms
of earning the respect of your peers, getting more of those opportunities.

(11:46):
So I liked that type of system where there was very much a reward for any type of good
work that you were doing.
And particularly if you got big opportunities and took advantage of those, that's where you
could see big jumps in your career.
I also think I learned a lot about what I was fit for and what I wasn't fit for.
I started out on a trading floor.
I could be considered type A in certain environments.

(12:06):
In that environment, I was the ultimate beta in a group of alphas and the idea that you
kind of keep your head down and just do your work was not actually a successful strategy
in that type of environment.
It was only until I moved into research where considered more analytical, considered more
of the library and quiet, deep work going on, which to some extent is true.

(12:30):
But that is where the type A that I did have in me was really able to shine and mixing
in the analytical work.
So that's where I really felt like I hit my stride and I realized what I could be good
at in that type of organization.
And comparing that to your early education experience, it sounds like a lot of potential

(12:51):
but didn't quite meet your own expectations of yourself.
But then when you got to be in the library setting, doing research for equities, that
sounds like where you really shied.
What did you learn about yourself in that figuring that out and seeing like, oh yeah,
I really enjoy going deep on this kind of subject.
I think the deep work was always of interest to me.
I think I had a lot of people telling me, you know, you're fit for sales.

(13:14):
You're outgoing and this is what you should be doing, even if it didn't necessarily give
me energy.
So I think you never want to overlook what people compliment about you or think that
you do well.
Sometimes we find people that are doing great things and they wouldn't even realize it.
It just becomes natural to them.
I'm not necessarily putting myself in that category in this case, but I think it's important

(13:38):
to remember what people are telling you that you're good at and making sure that you take
advantage of that, if that's true.
At the same time, you want to be doing things that give you energy.
And where I was falling short in sales is you're never the expert on anything or in very
rare circumstances, you have the most amount of information.
Whereas in research, you're expected to be the expert or the point of contact for certain

(14:00):
questions relating to whatever sector or field that you're covering.
And I think that was a much more comfortable position for me.
I hated having to hand off whoever the investor was onto the research analyst or somebody
else in the bank and not being able to give them the full answer.
So in research, that was the opportunity that I was then given.

(14:21):
And it's not always going to work out well because if you don't have the answer or the
answer is not to the investors liking, then that's going to be a good experience.
But you learn from that.
And that's the type of thing that motivates you to get better and better at what you're
doing.
So it was that process which kind of unlocked that realization for myself.
That's awesome.
You were pretty far into your financial services career when you switched over to content and

(14:46):
podcasting.
How did that actually play out?
So I had been listening to podcasts for many years at that point and audio to me was something
that I quickly became obsessed with.
It was this white space in my day that now was being filled with something I could learn
from.
You know, they're great podcasts as it relates to investing or just general business industry

(15:10):
dynamics that I wasn't getting elsewhere.
It was also entertaining.
I started to realize I was having these parasocial relationships with these hosts where there
were inside jokes or certain dynamics going on in their environments that I felt like
I was a part of.
And it felt very different than any other medium.
Video, text, there was something about the audio format that was major in terms of how

(15:33):
I was playing a role in everything that I was doing.
So I had this interest in audio.
I was very intrigued by it.
Then layer in the podcast that I probably listened to the most at the time and best like the best.
Patrick O'Shaughnessy was the host and he announced in the summer of 2020 that he was
going to build a team and build a business around his initial podcast.

(15:56):
And that just caught my attention.
Again, I'm in the finance world.
I think there's no way I'm leaving for the podcast world.
But he announces he's building and six months later he announces he's looking to bring someone
on to focus on building out the content.
As part of my work in research, I was writing research reports for investors doing various
forms of what you would consider content.

(16:17):
We could debate if it's the same type of content, but you get some idea of what people
care about.
So I thought to myself, here's something that's very interesting and I feel that's very interesting
and that the people that I would be working with, I find really, really intriguing.
They're young, they're hungry, they're doing something.
And this would be an opportunity to build something from the ground up.
I was not planning to leave the world of finance, but sometimes you have opportunities where

(16:42):
you think this is really, really interesting.
And in 40 years, if I didn't take that opportunity, I think I would be upset with myself.
And that's how it really came together.
I reached out to the team when they announced that they were doing this and the conversations
went on and on.
And ultimately we came to a nice arrangement and now it's been three years.
That's awesome.

(17:02):
And now you're CEO.
I mean, way to go.
What was the interview process actually like?
This doesn't sound like you're traditional.
This is a big company with formalized processes and an HR and recruiting department.
How did that actually play out in that first role you held?
So it is very much, you're completely right in terms of the process being much more boutique,

(17:23):
flexible in many ways, different in many ways.
But ultimately what they were looking for was give us some proof of work.
And I think this is increasingly common in large organizations today.
What can you show us that you've done?
It is not a resume that really speaks as loudly anymore, a cover letter.
You want to see something, some tangible output and a way to provide for that.

(17:47):
So upfront, it was provide some work that you've done that would make us think that
you could do this.
And that was just on the upfront application.
Show some interest in the content.
I think there was very much a test for do you actually care about this?
And fortunately, I definitely did.
So it's very familiar with a lot of what was going on there.
And then having conversations with everyone on the team was a team of four at the time

(18:09):
and then a few outsiders, multiple conversations with people from the team.
Actually doing some work as it relates to the natural week to week stuff that they were
working on, just getting my opinion on different things and basically seeing how my thought
process would fit into the own work process.
And then getting down in terms of negotiating the contract, what was great about it being

(18:33):
a small business was a lot of flexibility in terms of how we came to a structure that
would work from both sides.
It's no surprise to anyone, the finance world known for high wages, the podcasting world,
kind of more opaque in terms of what it can be.
But there was a lot of flexibility around if you hit certain milestones, that means the
companies hitting those milestones, that's a win-win where we can notch this up and ladder

(18:55):
this up to get you to a place where you're very comfortable.
So it was the ultimate example of how smaller companies can take on larger companies with
recruiting by being more flexible, by changing up the structure that you would typically
have with interviews and arriving at an agreement.
And within less than a year, you were promoted to CEO.

(19:17):
How did that play out?
So that was much more related to the organizational dynamics that were taking place.
You were essentially part of a portfolio of businesses, all somewhat related, but our
work was very separate.
And as part of that, the original CEO of Colossus actually went back to his previous
company to become CEO.

(19:38):
He had left his COO, he became CEO, great opportunity that just happened to come up
while all of this organizational change was going on.
And it quickly came to light that there needed to be somebody solely focused on Colossus
on the media, giving it sole attention, isolated attention.
And that's where I was tapped in to do that.

(19:59):
I think it ultimately came down to a trust factor of I can trust Matt to do all of these
tasks and nothing is going to fall through the cracks.
We could put him in front of anybody, he could be doing the behind the scenes work, but it
was in terms of the responsibilities, just meant taking on a lot more and basically taking
this mission to the next step, was a passing of the baton that happens.

(20:22):
But I think that a lot of media organizations help us understand where you fit within this
company.
It sounds like there's a portfolio of companies here, you are a CEO within the portfolio.
How does that structure work?
So it's been simplified quite a bit.
We now essentially operate isolated from those businesses.
Today, we have Colossus and then there is the venture capital fund of Patrick's positive

(20:47):
sum.
Those are the two teams that are working most closely together today.
There are each isolated businesses.
There's very much separation of church and state, but there are a lot of ways that we
can ultimately help each other.
We are certainly a funnel for interesting people that are either in our audience, featured
as our guests, featured as our sponsors, a variety of different ways that we have interesting

(21:11):
people coming through our doors.
Those can be interesting opportunities for positive sum.
Equally, they have interesting opportunities, whether they've backed these businesses or
these founders, and just been in touch with different organizations on the venture side
on the investing side.
You can see where there's some marriage between the two businesses and we're working on a
lot of more projects together just to really use all of the collective muscle that we have

(21:34):
between these organizations.
What we're trying to do is create a world for investors and high level business operators
that they can get the content that they want to consume, that's high value.
They can potentially be featured in a variety of different ways.
They can put money into the business via sponsorships, advertising opportunities where they know

(21:55):
they're hitting their target audience.
That's ultimately what we're trying to do is expand on that and really, you put out this
bat signal for those interesting people to come and find you.
That's ultimately what we're doing now.
Interesting.
Would you tell us a little bit about your team?
Sure.
As it's constructed today, we have essentially four full-time people working on Colossus,

(22:20):
me doing a little bit of everything from ad sales, sourcing, hosting shows, working with
the distribution, even the back office, finance, accounting, taxes, all the unglorious things.
We have Dom, who's heading up our content, who potentially was doing what I was doing
before, which was really being keyed in on every show, what's being released, all of

(22:42):
the coordination that goes into that, the editing, making sure things are polished.
We have Joanna, who again works across the business.
She joined us in the past year out of school, and she does a lot of supporting me in terms
of the various endeavors, and then taking the lead on certain shows where she can be
editing, sourcing, helping out.
Then we have Jo, who works on our engineering side, and he has built a website, has incorporated

(23:06):
all the transcripts, done a lot of the linkage between all of our materials, so you have
kind of a common destination.
We then have, between the positive sum team, where we have some people who are helping
out quite a bit with our business, they do a variety of different things, whether it's
related to our writing, related to helping out with the sponsorship efforts.

(23:26):
Then we have the vendors and the contractors who are extensions of our teams, our audio
editors.
You can narrow it down to saying when we have a weekly team meeting, it ends up being four
people usually.
When we are doing bigger group calls, that can be closer to 15.
If you extend who I'm talking to on a daily basis, it goes beyond that.

(23:47):
The measurements are always interesting to me, but that's how it currently operates today.
Makes sense, on a sense.
Would you tell us a little bit about what you had to learn to become a successful CEO in
this space?
I think there's a list of things that I had to learn, and there's a longer list of things
that I still will have to learn.
I think what's most important to me always is the leading by example, especially in a

(24:11):
remote environment.
We are remote, and that works to our benefit in many ways.
Dom being in Europe gives us some early cushion in the day.
When we release an episode, he has the ability, if anything has gone wrong, to catch that
before it truly gets to the mass of our audience in the US.
It just makes it important, leading by example, and then communicating.

(24:34):
This is the area that I think is almost cliche in many ways, but I constantly have to remind
myself to work on it, is the communication is so important to keep everybody rowing in
the same direction.
It just is a matter of, "Okay, I have these three different tasks.
Am I working on the website?
Am I working on this new plugin that we're building?

(24:55):
Or am I working on this random one-off project that somebody, one of our partners brought
in and needs to be done?"
That type of communication just needs to be constantly done for a variety of different
reasons as simple as prioritization and as important as morale, too.
I think that's very, very key.
That's probably one of the biggest areas that I think good CEOs, good managers, good people

(25:19):
within organizations are constantly delivering those messages and not letting this uncertainty
really fuel the system, which I think can really be a plague in many ways.
Sure. How do you think about the communication?
Is it just slack updates or emails?
I think everyone's going to have a different style and I think it's very dependent on the
work environment that you have.

(25:41):
If it's engineers, it's going to look a little bit different.
It might be daily stand-ups.
It might be weekly stand-ups.
For me, I think some form of weekly meeting is very, very important.
We basically have two, one oriented around content, one oriented around the business.
One on one calls, depending on how many direct reports you have, I think are very important

(26:02):
as well just to get a pulse check.
We have scheduled.
We do not have them every week, but I think it's good to have that placeholder and just
to allow that open conversation, you can deliver very specific things, usually have a laundry
list.
Those are things that are important.
Then slack, I think, is where I probably underestimated the benefit of additional communication.

(26:26):
It's so easy with slack to pull back from doing that because you do not get any type
of response unless somebody opts into responding to you.
That could be emojis, which can mean a whole host of different things.
That can be actual replies and sometimes it's nothing.
I think what we often do is if we get nothing more than once, then we just stop doing it.

(26:48):
That is not the answer.
I think I need to constantly remind myself.
In 10 years from now, there'll be some great business book about managing organizations
that are mostly remote.
There's a whole industry that needs to be created around that or will be created.
I don't know if it needs to be.
But at this point, I think that's been one of the biggest lessons to me is the challenges
of the organization when it comes to communication outside of day-to-day interaction.

(27:12):
Makes a lot of sense.
We'll get back to the conversation shortly, but I wanted to tell you about how I can help
you find your fit.
I offer one-on-one career coaching services for experienced professionals who are preparing
to find and land their next role.
If you're a director, vice president, or a C-suite executive and you're ready to explore new
opportunities, please go to GoodFitCareers.com to apply for a free consultation.

(27:37):
I also occasionally send a newsletter which includes stories from professionals who have
found their fit, strategies, and insights that might be helpful in your job search and
content that I found particularly useful or interesting.
If you'd like to learn more, check out GoodFitCareers.com and follow me on LinkedIn.
Now back to the conversation.
What does a good year actually look like for you as the CEO?

(28:01):
Well, there are certainly monetary targets that are always important to hit revenue growth.
I think to me, given our size, we're seven figures in terms of where we are in revenue.
Depending on how you measure revenue, you can bump that up in different ways.
But that to me is, that's a number that I want to be so substantially larger than that.

(28:28):
Yes, the growth of that is important, but a lot more is about the foundation that's going
to lead to that growth.
If we develop a product that we can then sell which really unlocks the ability to grow that
number in multiples, what are we going to need?
We're going to need an audience with people that would be interested in that and really
tailoring things to having the audience that we want and making sure that we have their

(28:51):
attention, we have their trust.
A lot of what I try to measure is, what are we shipping in terms of the content?
What type of engagement is that getting?
What is that fueling in terms of communication that's coming back to us?
Can we continuously do that where we have more and more of these people in our audience,
in our group, and we've had them in there for longer, or we've really built trust with

(29:15):
these people that we're serving them in ways that they want?
Because that to me is one of the biggest assets that we have that goes beyond anything else
is just the network and the community of people that are listeners beyond my expectations.
That to me is what's most important.
Makes a lot of sense.
What keeps you up at night as CEO?

(29:37):
It's always going to be the what can we do that really innovates on top of what we're
already doing.
That next step on the ladder, it's that next three steps, how are we going to get there?
How are we going to get there collectively?
I think you can have the individual view.

(29:57):
How do I get everybody on board to do it?
Then how do I make it happen?
I think it's the ideas that you have running through your head and executing on those ideas.
To me, it's not so much, oh, I worry about an episode going out with somebody's name pronounced
wrong or something not getting shipped right in that direction.

(30:21):
It's very much a how are we going to accomplish these next few projects that can potentially
take us to the new level and execute on them properly.
I feel very confident anytime we're shipping something in audio, we're doing something
in other mediums.
That is where I get that nervous energy that will ripple through my veins in the evenings.

(30:43):
Yeah, I hear you.
What did you expect it to be like to become a CEO and what was it like in reality?
I think if I had expectations, I can't say this specifically, but if I had expectations,
probably would have been more monumental or I think sometimes you have these movie-esque

(31:04):
images of what things are like.
In reality, it was very much just taking on more responsibility and doing a lot of the
same things that I was already doing.
It was just business as usual plus like many things and you just get down to business.
I think when I look back on various experiences that I've had in my career with getting more

(31:26):
responsibility, that's often the case is it feels overwhelming to think about, "Oh, I
might have that responsibility where my name is attached to all that stuff."
I can't even imagine what that would be like.
Then you get closer and closer to it and then it just feels very natural as a transition
is made.
I think reflecting on it, it's a lot of words and then the reality of it is just a lot of

(31:49):
actions and it's just getting back to that usual stuff.
I think it's important to reflect on these things and make sure to zoom out where that's
probably more important for CEOs and managers is the zooming out and it can be easy to get
lost in the execution.
But net net, I would say, it was not this whoa overhaul to my life in a way where maybe

(32:11):
I could have expected that.
To zoom out a little bit and to be a little bit more philosophical here, what does your
work mean to you?
To me, it's what I leave out there in the world.
I'm not a big, "Oh, you have this legacy."
I think that can happen from business standpoints, from personal standpoints is the work that

(32:34):
I'm doing having some impact and having some shelf life.
One thing that's very important to me is this is something that somebody could listen to
not only today, but two years from now, five years from now, 10 years from now.
There's something very interesting about creating something like that.
It's non perishable, a long shelf life.
That to me is what means the most.

(32:57):
I think mostly about what is actually going on into the world.
It's why I can get incredibly frustrated when I have to spend time on taxes and accounting
things which are necessary evils, but stop me from being able to focus on that product
and content and the quality of things that we're putting out there into the world because
it just brings so much back in a good way.

(33:20):
It lives out there forever.
You see some of the rewards in the early days, but I have had so many experiences where those
rewards came years after content has been released.
I think that's a beautiful segue.
Focusing on the quality of the work, some of your shows have had extraordinary success.
Would you teach us a little bit about your perspective on creating truly good work?

(33:45):
There are different aspects of quality when it comes to something like business investing
content.
When you're creating something for individuals out in the workforce, maybe already accomplished
in their career, you really need to be thoughtful about what you're doing for them and what
their takeaways are going to be.

(34:05):
I think it's so easy to get lost with content about, am I actually solving something for
the listeners?
Something good that's coming out of this that's going to be a takeaway.
We can get instead lost in the, "Oh, there was good flow to that."
That was a nice conversation and made me feel good, but it might not have any extension

(34:25):
to the audience.
I think that's one thing that's important is who are you trying to reach and what type
of impact are you going to have on them?
When I was writing research, there used to be a very simple mantra of, "When any time
you looked at a piece, the questions were, what did I learn and now what do I do with
it?"
I don't think that always has to be the case with podcasts.

(34:48):
It can simply be, "What did I learn?"
It's up to you to figure out what to do with it.
I think that's a good at least directional steering in terms of what you're trying to
accomplish.
There are podcasts that are solely focused on entertainment.
I think that that plays a role in any type of content.
You need to keep some element of entertainment involved there, keep some type of natural

(35:12):
charisma and audience engagement that just is important.
It's not the number one thing on our list, but we take that into consideration.
Those are the things that I put together, and it's just a willingness to provide new
information, something that people don't already know, and then give them some steering in
terms of what can you do with that information?
How might it apply to you?

(35:32):
That's like if I boiled it down the most important things.
One of the things that I'm curious about is going from zero to one, building something
from the ground up.
Would you walk us through how you built the Business Breakdowns podcast?
Sure.
I came in in the middle of that project being in launch idea phase, but I came in very much

(35:56):
in terms of seeing this going through the reps.
It was an idea that idea was how can we just boil down the densest way to quickly learn
about a business?
It is if you know nothing about this company, you spend 45 minutes doing an hour listening
to this podcast, you're going to have the most efficient time used in terms of learning

(36:17):
about something.
That's relative to reading a 10K, reading an annual report.
This podcast is going to give you great context, bring you to zero to six or zero to seven
on a 10 scale.
Not answering everything, but really putting you in the right spot.
This was a tricky task, you need to find the right guests to do it on a weekly basis.
These guests are often in investment organizations with heavy compliance.

(36:41):
Getting approvals and getting cooperation is difficult.
When you're talking about things very numbers oriented, preparing for that is different than
preparing for just a natural flow conversation.
There was going to be more prep work involved, but what it ultimately came down to is reps.
There were probably 30 episodes that were done just as essentially practice episodes
that were thrown out prior to launch.

(37:04):
And even when we did launch, it was constantly a recalculating of, "Okay, what do we want
to do?"
We've had management teams on, the audience doesn't seem to like them, they tend to be
way too positively biased, let's shift to having more investors or people close to
that industry that can provide a more balanced information.

(37:24):
It also changed the structure of the conversation.
They were a little too inconsistent.
Now we have six general areas that we try to cover.
They might come in different spots, but at least you know what you're going to get out
of the conversations.
So, it's constantly tweaking that.
And I did not believe that we would be able to accomplish what we did.
I had skeptical doubts about being able to do this weekly, so it surpassed all of my

(37:47):
expectations.
Wow.
As we transition over to perceptions and misconceptions here, would you tell us a little bit about
how you believe the world sees your job as CEO of Colossus?
So I think many people think that it would be incredible that we're working on really
interesting things.

(38:08):
We get to talk to really interesting people.
And I would mostly agree, it is an awesome organization, awesome opportunity.
There are so many little things that go into running a business.
I think particularly for investors, it's so hard to comprehend what goes into operational
roles.
That sounds more of a plea for sympathy on that side of things.

(38:29):
But I also think that there's some skepticism as it relates to any investors viewing content.
What is the angle here?
What are they trying to do?
And ultimately, I wish it's really just about we care about our audience.
And our content conversations, there is not groupthink when Patrick, Dom, and I will talk

(38:49):
about episodes.
There's a lot of back and forth.
There's a lot of debate.
There's a lot of...
It's not yes men, it's not groupthink.
And I think that is something that maybe doesn't get captured in terms of the perception
of what we do.
I think one of the things that I'm really curious about, you mentioned you had 30 or
so practice episodes that didn't quite make it to the public.

(39:11):
Was there a moment or like a formula or some sort of way of saying, "Okay, now we're on
episode 31 of this practice and this is ready to go?
What was that delineation?"
I would say it did not happen where episode 30 was a no and episode 31 was a yes.
What actually happened was it was probably episode 24 was a yes, we got one.

(39:33):
Episode 25, 26, 27 were no's.
28 was a yes.
We had basically four episodes ready to go at launch and those came at various points.
Some of it was our mistake.
The hosts just maybe not taking the conversation to areas they wanted to go, not being as consistent
with the flow, not having the rapport with the guest.

(39:55):
Some of it was the guest challenges.
But I think we knew it when we were going to hear it.
There were certain things that we were looking for and you can walk away saying, "Yep, this
is it."
And to this day, we still don't run a lot of episodes.
So that's still not uncommon for us.
It's a quality bar thing.
But we know when we hear something that does meet that quality bar.
How interesting.

(40:16):
I imagine most people don't understand that as a podcast producer that there are a whole
bunch of episodes that the world might not ever listen to.
Yes, there are some great episodes.
Sometimes it's the guest that doesn't want to run it.
So it's not uncommon.
But there's a lot in the library.
You'd mentioned earlier that you really care about the audience.

(40:38):
There's an obsession with what they care about.
How do you begin to measure what they care about and perhaps frame this in the way that
you'd give advice to someone like me or anyone else producing a podcast?
I think that you can't overweight individual opinions too frequently.
I think it's very easy to go on to Twitter or LinkedIn and see three to four really loud,

(41:03):
aggressive opinions and miss out that that is the tiniest fraction of the audience.
So what I think often comes is you'll get negative feedback more often than you'll get
positive feedback.
I think people that are giving positive feedback are doing it by listening from week to week.
So I think having that right up front is important.
I do think sometimes we can overcorrect based on opinions that are not widely held.

(41:28):
That said, I think when we have things that we are unsure of, we will ask the audience
for feedback.
We're testing this out.
We'd love to hear what you think.
And we'll usually get some follow-ups.
And a lot of those we'd be done privately.
You will sometimes get really Dharhard listeners that it pains them to give you negative feedback.

(41:51):
And what I appreciate sometimes is the lead-up paragraphs of the, you know, essentially
don't take this the wrong way, all of this qualifying positive.
And then three paragraphs on why they didn't think that episode was a fair representation
of this or that.
And those I really appreciate.
I don't need necessarily all the build-up.

(42:11):
But when you've really thought it out, explain why something didn't work or didn't really
meet your standards, those are things that we appreciate and then we can adjust from
there.
So I think it's a combination of asking when you're curious and then fielding it from select
groups or individual types that you can trust.

(42:31):
Feel free to take a swing at either of these or both.
But what do you wish that people knew about your job as CEO?
Or what do you wish people knew about the podcasting world more broadly?
Well, I think there's two things.
I think in terms of the inspirational answer, the thing that I wish everybody could experience

(42:53):
is putting something out there in the world, creating something great, like a podcast episode
and seeing the feedback and the inbound commentary that you get from people, how detailed it
is, how impressive some of these people are, not that it should matter, but it could be
celebrities or business celebrities wherever we want to categorize those.

(43:14):
And you're thinking to yourself, wow, this is insane.
And usually the conversations don't stop there.
So I think that is something that it's so hard to appreciate until you've gone through
the experience and why I always recommend people starting podcasts.
If it's something that you enjoy, you can get so much out of it and it doesn't have to

(43:36):
be monetary.
The other thing that I would mention is just what goes into a lot of the work, how we think
about trying to improve the product.
That is more of a looking for sympathy type answer and I wouldn't, you know, plea that
to the audience.
But I think if they saw inside the factory in terms of how these things are done, the

(43:57):
pushback that we give on guests or in different opportunities that arise, they would walk
away with more respect for what we're doing and sometimes telling that story is important.
If someone is excited about starting a podcast, they've got an area that they're very passionate
about, they're convinced that this is what they're going to do.
What sort of expectations would you set for them?

(44:20):
I think trying.
There's no reps are so important.
I have seen so many people with interest that do three to four and then the interest winds
down.
So there's no substitute for trying it out.
Expect it to be a long road.
Do not expect to be a success from day one.

(44:41):
And there's benefits to, you know, creating this habit, putting it out there, seeing it
grow over time.
And that's the expectation that you should have.
You should have the expectation that we often say don't expect to make any money for a year
and would you still do it?
And that's a good litmus test for their interest in it.
Those are the things, but I would encourage people to go through the experience because

(45:03):
I think it's very unique and it's such a low barrier to entry that there's not a lot of
things stopping you.
Let's talk a little bit about hiring.
So now that you're CEO, you have a relatively small team, you've got a handful of contractors
out there.
Can you tell us a little bit about your philosophy for hiring for your own team?
Sure.
So we want some type of affinity to the content itself.

(45:29):
I think if you look at successful media businesses over time, whether it's ESPN, Saturday Night
Live, there's a great book recently on the Village Voice.
You know, these are just examples, HBO.
There's a real care for the brand and what they're putting out there.
And because the content has so many touch points, you know, so many people have their fingerprints

(45:51):
on it.
And we want that type of pride in terms of what you're shipping.
So teasing that out is really important to me, important to us.
That's number one.
From there, it's a matter of the depending on what role you're going to fit.
Again, just the attention to detail and the ability to meet deadlines, do the small things.

(46:15):
You know, if I were hiring for a salesperson, I would have different criteria.
But for so much of what we're doing, it's very dependent on people getting their work
done in the windows of time that they need to get it done for the next person to put their
fingerprints on it.
There is a lot of manual work in the factory.
And we pulled out as much as we possibly could to make it more efficient.
But those are important things.

(46:35):
So it's that and then some form of taste in terms of appreciating what we're doing and
having a real desire to make it tasteful for who's consuming it.
Those are the most important thing.
And then you get into the other things like you want to trust somebody, obviously.
That's very important.
You want somebody to be ambitious and be on board with something that's growing.

(46:57):
So those are the main things that I would point to.
You've been hired in some of the most rigorous, competitive, perhaps brutal hiring processes
that exist.
You've also been hired and promoted within the flexible, dynamic, kind of boutique hiring
structure.
Do you believe that there's an ideal hiring process today?

(47:18):
I, not a one size fits all.
I think for organizations, it could be very dependent on, again, the position that you're
hiring for.
I do think that hiring processes have changed and rightfully so, where there should be a
lot more dependence on proof of work.
What have you done?
And what can you show us that you've done?

(47:40):
And the reference checks that go beyond this is who I've provided.
I think there's so much to be learned from that that will not come up in an interview
that I think there's a certain amount that should go into that, where the incremental
work to be done is let's see things that you have done before and we can get some sense

(48:01):
of your work product.
And then also let's talk to some people that you've worked with and we can get a sense from
them.
And you have to have your own ability to tease out what those people are saying, the value
in that, whether good or bad, extending beyond just the close relationships that they have.
But those to me are the two things that I think offer the most opportunity for organizations

(48:24):
to change and lean into that will provide the best outcome.
What might compel you to take a chance on a candidate?
It's usually something that indicates that they have picked up on something that is non-obvious
and I'll just use an example.

(48:45):
This feels very small, but Joanna, who works for us in one of our early conversations,
she had worked for a large company and was running social media for one of their management
team members and she got a reply from another high profile person.
So basically two celebrities talking on social media and what she was thinking to herself

(49:07):
was, this is probably not two celebrities, it's probably two people working for these
celebrities that are communicating and the world thinks that there's two celebrities
talking on social media.
And it was just this layer of depth and awareness in terms of the system and not to get too
caught up in certain things which could easily pull people and make them feel some form of

(49:29):
FOMO or some other over weighted reaction that to me it felt like she had this insight.
And that was just a very small thing from a long list of other things that you went through
that stood out to me.
So that's number one.
And then number two is just these examples of unique experience where I think some of

(49:50):
the best people come out of smaller schools, but they have fought, they have done things
and accomplished things in their life which required a lot more flexibility outside traditional
systems and that just shows like a street smarts ability that I think can get lost with other

(50:10):
people who have maybe been in a rigid system for their entire career or their entire educational
career.
Sure.
In terms of leadership, management and kind of achieving outstanding outcomes, how do
you think about accountability and performance management?
Super super super important accountability I think for everyone is the most important

(50:35):
thing.
You need to be accountable yourself that I put this person in a bad position, that I need
not meet my end of the bargain and you can hold them accountable as well.
And I think that creates a high trust system where everybody is working hard, you can make
mistakes, you own up to the mistakes and they'll wash away to the extent that you don't make

(50:58):
them too often.
That goes such a long way where I think it's important.
I think sometimes it could be hard to figure out, oh, how do I create a system where there's
like ultimate checkpoints of accountability, particularly in work that's not as numbers
based, but you have to work hard to do that.
And then you have to hold people accountable because that's what makes them better.
And I do find with most people, they make mistakes once and they learn from them.

(51:24):
And the faster that you can get through that, the faster they're going to feel comfortable
and that they're working with a certain level of urgency to make things better.
Makes sense.
For somebody who had a transition like yours, being an expert in an industry at a relatively
large company and then transitioning into management and leadership at a smaller company,

(51:46):
what sort of advice would you have for those new managers?
I think, don't forget what it takes.
And I think one of the best experiences I had was I was a manager with a lot of autonomy
at Goldman, where I had a boss, but they were several chains up the ladder where I basically

(52:08):
had freedom.
We met a few times a year.
I had a team.
When I went to Raven, I had a lot of people that I was reporting into and there were people
under me, but they weren't necessarily my team.
And what I realized there was, you know what?
This is reminding me that managers, you don't get the full picture of everything.

(52:28):
You're getting some adjusted response.
All of your jokes are funny.
You're going to get some pushback, but they're picking their battles.
So I think that's like one of these things where once you move into smaller organizations,
you need to reset a little bit.
You need to be willing to get your fingernails dirty where I think I go back and forth on
setting the tone.

(52:48):
You know, there's some benefits.
I remember my best friend's father told me, don't be the guy who's in there first thing
in the morning every day when you start work.
Because then if you ever want to change that, people will notice and they'll say you're
slacking off.
You might want to be the third guy in.
You might want to be in the early chain, but don't make your reputation that because

(53:09):
the pain of ripping that off is going to be ugly.
And you're setting yourself a standard, which how valuable is that?
It was just interesting insight to me.
So there's the level setting.
But I think with small organizations, you just need to be willing to do everything.
And you'll learn a lot about what everybody's doing then.
It'll build a lot of respect with the rest of your team.
And I think from there, you can hand things off.

(53:32):
But I think if you don't want to be doing that, you should ask yourself, do I really
want to make this change?
It's a lot easier to lean on your experience in bigger organizations than it is in smaller
organizations.
Tremendous advice.
And I love that perspective.
As we begin to wind this conversation down at a macro level, what are you excited about

(53:55):
for the future?
Just what we can continue to ship in terms of the quality that we are thinking about
when it relates to written work, potential video work.
These are all experiments.
We don't want to just do it where you're not getting additional value versus what you
would get from a podcast.

(54:16):
We want to make it feel like, oh, this is a step up.
I'm getting something that I wouldn't be able to otherwise capture.
And having that influence, you know, all of what we talked about before with the world
building, I would love in 10 years from now to have our library, which has already grown
with how many hours of episodes that people can get lost in.

(54:37):
That will just continue to grow week to week.
But then if we're doing more, we're shipping more, we have this library of content and
people that have now really dug in and become, you know, stakeholders in various forms of
the business, that to me is exciting because it feels very new.
You know, in many ways, this is a case study in why do you spend so much time studying success
stories or studying business?

(54:59):
And you do it so that you can start a successful business.
So we are, you know, patient zero for seeing whether all that is worth it.
And that to me gets me excited.
It also lights a fire under me to prove that all of this is very valuable.
Well said.
We're recording this in May of 2024.

(55:20):
What do you think your field is going to look like in 2030?
Significantly different because we've learned that everything looks very, very different
versus where we were just six years ago.
I think that the conversations with individuals is something that's going to become more and
more important to be doing personally.

(55:41):
I think conversations to me are everything that is value in the world because you're
going to take what you learned.
You're going to take what somebody else has learned.
And it's going to be able to basically pull out that to one another.
So you're basically informing each other.
But then also you're going to be able to build on it.
And it's synergy gets overused in business.
But there are one plus one equals three outcomes here where you're having conversations and

(56:05):
you're just basically creating enlightening moments of, okay, I'm connecting a lot of
dots between our two contexts that we're bringing together.
You're sharing that with the world.
I think that's important on a personal in your personal life as well.
You need to be constantly having conversations.
You're not interviews, conversations, incredibly important.
And I think that's only going to become more and more magnified as AI gets better and better

(56:29):
to have reliable people that you can go to and ask for opinions on things.
And I hope that that improves what we're doing now.
Just about media in general.
I think there's more and more shift towards individuals over institutions.
That's very commonly held view these days.
And I think that will continue to be the shift over time.

(56:49):
So there's going to be trust in individuals.
And hopefully what we can create is a brand above those individuals that people trust
that when we introduce somebody new, there's a stamp that is some type of approval and
being something.
I think it's going to be so fascinating to see how that plays out.
This might be a little bit of a complicated question given your position, but are there

(57:11):
any books or podcasts or other content that you'd like to recommend to the audience that
you find particularly delightful?
Sure.
I mean, depending on what you're looking for, if you're in the world of entertainment,
something I always enjoy is film and TV industry because I think there's so many parallels
to what I'm doing from a content perspective.

(57:33):
But then also industry as a whole.
I think when you look at how movies have evolved over the years, so many lessons that
you can take away, directors in many ways being the founders of that field and of that
world.
And I think it's a popular platform, but the ringer has some great shows in that category
with the big picture, the watch and some others.

(57:56):
I also think that there are other shows that extend outside of us that are commonly listened
to and I think are always great.
So depending on if you want, kind of like that story-based business history acquired
is great for that.
And there's a variety of others that I could list off.
I wouldn't want to shortchange anybody.

(58:16):
And I'm always open to D Amazon.
If you have a category, I can probably give you a show that I like.
Right on.
Well, very last question here.
Do you have any parting words of advice or inspiration for our broader audience?
Think I tapped into it a little bit before, but the power of creation is really hard to

(58:38):
overstate.
I think that I felt some of this in my Goldman days of shipping research reports where I
will still from time to time get outreach because those reports are out there in the
system to be discovered.
But when you do great projects that have your name attached to them, kind of leading
name, and that can be just in your company.

(58:59):
You put together something that simplifies the workflow or gives people something that
they can use anecdotes from customers.
Great ways that people are framing things and packaging it nicely so it's easy to consume.
These little things go such a long way in terms of getting attention.
I think what we often do is get stuck on our own head thinking about how am I going

(59:20):
to create my next opportunity?
Oftentimes it's how is the next opportunity going to arise?
Not even thinking about how we create it.
The way you create the opportunities is by creating the great work.
So whatever it is, I just really, really recommend that people think about different things that
they can do and they can put out there because it's so fulfilling in so many different ways.
And it can bring you opportunities, ways beyond your imagination.

(59:43):
All it takes is one person to respond and have a great opportunity.
So you can get lost in the numbers and think about thousands and millions and all these
things.
But really it comes down to one, one or two people that can create your next job opportunity
to create your next interesting business endeavor.
And that's what's special about the world that we live in.
The internet has made this so easy to do.

(01:00:04):
What a beautiful way to close.
Matt, you've been so very generous with your time and your wisdom.
Thank you so much for joining me and sharing your perspective.
Thanks for having me, Ryan.
It's been a blast.
Great to think through this with you and love the way that you're approaching us.
Thank you very much.
Our next episode is with Nick Anastasiades, Chief Growth Officer of Nyla.

(01:00:26):
This isn't the most important thing by far.
It's having the right team that you're able to go through the journey with us.
If you enjoyed this episode, make sure to subscribe for new episodes, leave a review, and tell
a friend.
GoodFit Careers is hosted by me, Ryan Dickerson, and is produced and edited by Melo-Vox Productions.
Marketing is by StoryAngled, and our theme music is by Surftronica with additional music

(01:00:50):
from Andrew Espronceda.
I'd like to express my gratitude to all of our guests for sharing their time, stories,
and perspectives with us.
And finally, thank you to all of our listeners.
If you have any recommendations on future guests, questions, or comments, please send
us an email at [e-mail].
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