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From Parking Cars to VC Success: Rob Matzkin’s Journey to Thriving as a Fractional Executive · Founder Unfiltered - What Founders Think But Never Say

0:00
Welcome to another episode of 6 Figure Secrets for Fractional
0:03
Experts. My name is Bradley Jacobs.
0:05
I'm your host and the founder and CEO of Mylance.
0:09
Today I'm joined by Rob Matzkin. Rob has over 20 years of
0:14
experience helping high growth SAS and AI startups raise
0:17
capital and scale with clarity. Last five years he's been
0:20
running his own fractional business and still in the VC
0:24
world as well. Rob, welcome to the show.
0:27
Thanks for having me, appreciate it.
0:29
All right, expand on my intro. Like, tell us more about who you
0:33
are, what you do, how you got here.
0:35
So I'll just kick it off from a professional perspective, really
0:39
actually grew up in my family business in high school,
0:42
realized that was not a path I wanted to go down after working
0:47
there for a year and then jumped into the world of
0:52
entrepreneurship. Kind of randomly ended up
0:55
starting a company called Booze Carriage, which was me inventing
1:00
the alcohol delivery space in the United in the US 3 1/2
1:04
years. Quickly took that to an
1:05
acquisition. And then from there I've started
1:08
16 different companies, have two, have had two separate
1:11
exits. Got into investing with my
1:14
family office and out of my VC fund and also these days do a
1:19
tremendous amount of consulting and coaching, particularly
1:23
around startups raising money because I've seen both ends and
1:27
it's really a purpose driven business for me trying to make a
1:30
difference for others. I also have a purpose driven
1:33
business summit that I do where I try and bring where I do bring
1:38
purpose driven entrepreneurs together.
1:40
So I've done a few different things across the board.
1:44
Amazing. And you, you mentioned purpose
1:46
driven two or three times. So what is your purpose in this
1:50
in this? World.
1:53
You know, that's a funny question because what is my
1:56
purpose? And I don't know if I have that
1:58
clearly defined yet. I'll say this, right?
2:00
What really fulfills me is making a huge impact on other
2:03
people's lives and seeing other people thrive, right?
2:07
It, it, it really lights me up. Of course, I, I love seeing my
2:11
own success as well. But really what fulfills me is
2:13
that, and I think it's a good question that I actually need to
2:15
answer and put up on the whiteboard that what is my
2:18
purpose? Still seeking it in many ways I
2:20
think. I love just the honesty there,
2:22
right? You could have just made
2:23
something up real, real quick. But it's kind of an evolving
2:26
thing, right? Like your purpose does change
2:29
and evolve as you do and learn different things.
2:31
And then what? But what I like is you, I think
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you've made, you've had a lot of success in your life.
2:36
And so now you kind of the natural thing is to come back
2:39
to, OK, what do I really want to do?
2:42
What like what impact do I want to make on this planet?
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You know, there's, there's plenty of things that really
2:47
interest me, right, as far as where I can make an impact,
2:51
right? Education is huge for me.
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I grew up dyslexic. I still am dyslexic, right?
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And I didn't read till I was 10 years old, right?
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So learning disabilities and things of that nature, huge
3:03
impact that I want to make. What I say it's my purpose to
3:05
change it. I don't know.
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Is that something that's really, I really care about it and I'm
3:09
passionate about it. Absolutely right.
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And even today how I cope with that and deal with that in
3:14
business and navigate business with that.
3:18
I don't want to say it's a disability.
3:19
I think it's actually my greatest advantage of how I
3:22
think differently. But there's a lot of things that
3:24
I'm that I'm passionate about. So I love hearing people's
3:28
starter stories and often the starter story is kind of this
3:31
random thing that happened, but it's really not because, you
3:36
know, there's very few people that would take the random thing
3:38
and turn it into a business, right?
3:41
And you did that with this golf tournament crowd and you turn it
3:45
into a 20K weekend parking business.
3:48
Tell us the the story. What like what happened?
3:51
Yeah, it was. It was really simple and it was
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like, so I grew up near still a golf course called Wingfoot,
3:57
which is where the US Open comes golf tournament comes every like
4:00
8 years or something. So when I was what I was 19 or
4:04
20, they came to town and there was no parking for, you know, 15
4:10
miles or something. People are bussing in from an
4:12
hour away. So I was like, we're a mile
4:14
away. Let's but let's show for people
4:16
in We charged 100 bucks a car fit like 75 cars in a day to
4:21
create. But the wildest thing about it
4:23
was it was like every spectrum of business because OK, we
4:27
advertise, we put a sign up great.
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But then the next day, the cotton, the cops were parking
4:32
across the street in this huge lot.
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So like state troopers that I was talking to all day and the
4:36
street was shut down. But we're getting people in.
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So I was navigating law enforcement that I was
4:41
navigating local municipalities because there's an ordinance in
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my in my parents town where you couldn't park on the grass, but
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we had a big lot. So we were putting them people
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on like the pavement. So this whole thing to navigate
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and the city was trying to shut us down and we're shuttling cars
4:56
over to auxiliary to the different town, over to buddies
4:58
place. It was all this thing that I was
5:00
working with friends as well and my friends wanted a piece of the
5:03
business and they're just hourly.
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So it's like all the things of business and like a four day
5:08
thing that I was navigating. But it was a fun little cash cow
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and nothing. I love it.
5:12
Like you as a 19 year old are now navigating law enforcement
5:16
and the city municipalities and like subcontracting your
5:19
friends. And then I don't know, did you
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have like an entity? Did you pay taxes on this?
5:23
Like what? I mean, we're being recorded.
5:25
I'm not answering that question fair.
5:27
Enough. A horrible question, but.
5:29
No, but no. Yeah.
5:32
So yeah, but I'm sure. I'm sure you learned a ton in an
5:37
incredibly short period of time. And I guess what would you like?
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What lesson do you take? I'm sure there's a million, but.
5:45
There, there is a million, but I think one of the lessons that I
5:49
think was unfortunate that I've I've rethought about is when
5:54
working with at the time, I was like never working with friends
5:57
again, because you know, they they thought they like owned the
6:01
company, which they did. But really just being clear.
6:04
I think that the new take away, looking at it precious, you got
6:07
to be really clear with people when you start out, right and
6:10
really open and transparent and what the actual contract is,
6:16
right. And I didn't do that.
6:17
I flew by the seat of my pants and asked them to help me out,
6:20
right? And I thought I was doing them a
6:22
favor. They thought they were getting a
6:23
piece. So I think that's the biggest
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lesson in how to navigate interpersonal relationships,
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especially when it comes to money and really being delicate
6:31
with that. And it and it and it, I think
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everybody still has that challenge.
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I still have that challenge to this day, but I'm just really
6:37
straightened and and very upfront with what that is and
6:40
managing expectations. I love that.
6:43
And I would also just say even hearing the story, just go do
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the thing. Oh yeah, right.
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Like how many people would want to be planning Like, OK, what
6:51
are we going to deal with this and then this and then this and
6:54
then this? It's like just just freaking do
6:56
it. Oh yeah, no, I'm a huge fan.
6:58
I I read the books later in life, but screw it, just do it
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by Richard Branson. Right.
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But if I, like tried getting permission from the city,
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there's no way that would have happened.
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I would have been shut down even if I was six months out.
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Like just, and if you're not harming people, like just go for
7:14
it, right? If you're not actually calling
7:16
causing harm and then deal with it later, right?
7:19
And if the city came after me, it would have been fine.
7:21
My dad yelled at me because we broke a bunch of sprinklers, but
7:24
you know, it was fine. Is you're kind of reminding me,
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I worked at Uber back in the day and you know, we are drivers.
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The drivers were getting ticketed and cars impounded.
7:35
Taxi lobby is coming after us threatening, you know,
7:39
arresting, you know, GMs of cities sometimes.
7:41
I mean, it was really ruthless, frankly, in many ways.
7:45
And Travis CEO, the time founder of the company was like, we're
7:50
going to just do this. And because it's this is the
7:52
best answer for transportation, right?
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This taxis are not the best answer.
7:56
So we're just going to do it and we'll deal with it.
7:58
And city by city, by city, state by state, country by country by
8:02
country, they did. They did it right.
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Like I was negotiating with the Raleigh Durham Airport for like
8:07
a year and a half and I was like 24 years old.
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And it's like, OK, we're just going to figure this.
8:10
We're going to figure it out. That's awesome that we had to be
8:14
quite an experience that had to be.
8:16
It was crazy. My favorite, just quick anecdote
8:19
is they the Raleigh Durham airport asked for us to send
8:24
over all of our files like I'm the drivers, like they wanted
8:28
all like the data and the trip date and all this stuff.
8:31
And and I was like, what do you mean by the files?
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And she goes, you know, where you have like the massive filing
8:35
cabinets and you like send over all this shit.
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And I laughed. I did.
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I was like, we don't have those right?
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Like it's in a queriable database and she's like, what
8:44
are you talking about? It's like.
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You're like, yeah, I'll export you in Excel or CSV that you
8:50
could take a look at which fields do you what specific that
8:54
fields do you want? Yeah.
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And she's like, what's a CSV? You know, it's just like, yeah,
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it was, it was great. Anyway, one of the things that
9:01
you've talked about is frankly what no one talks about, right,
9:05
Being a founder when things are hard, right?
9:09
And, and really getting into what it's like, what the
9:12
experience is like, the emotional, the physical, the
9:14
financial toll of building something from scratch.
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And a lot of our audience are fractional executives.
9:20
So they're selling a service, but they're they're
9:23
entrepreneurial, right? At the end of the day, you don't
9:25
go out on your own if you're not entrepreneurial to some degree
9:29
or to a large degree. So what would you share from
9:33
that point of view of what is it really like to be out there?
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I mean, obviously I know, but I want to hear from your point of
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view. No, I, I, I think it's great,
9:41
right? Because, you know, even even
9:42
today, I, I, I, I go through this, right?
9:45
But it's like it's a frigging roller coaster.
9:47
And anybody who says it's not is, is lying, right?
9:51
I, I remember I was 28, I picked up the book The Hard Things
9:57
about Hard Things by Ben Horowitz and this book, it blew
10:01
my mind at the time because especially doing a start up,
10:04
you're raising money from friends, from family, from
10:07
everybody you know, and you have to look good because your
10:09
customers have to think you're succeeding.
10:11
You can't say things are bad. You have nobody to speak to.
10:14
And you're literally on this own little plateau.
10:17
Like even your girlfriend has to think or whoever your spouse is
10:20
at the time has to think. Everything's going perfectly.
10:22
And I was like, and then I read the book, I'm like, Oh my God,
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I'm not alone. Everybody goes through this.
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This is and what he went through was like, you know, peanuts to
10:31
what I'm going through. And it just trickles down to
10:35
even today, right? Like, you know, even like a
10:40
client's going out of business and one client's like off gal
10:44
venting around the world and all of a sudden I'm two clients down
10:47
and I'm going, well, there's a good chunk of revenue.
10:51
And you know, I went from being like sitting pretty to OK, this
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month. I need to like, let's hustle,
10:57
let's get a few more clients. Let's make up for this, right?
10:59
And I don't think that ever necessarily stops unless you get
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to an overwhelming point of lead generation and really getting
11:07
over like a certain inflection point.
11:10
But it's the nature of business. You're you're going to you're
11:13
you're going to be here, you're going to want to grow, you're
11:15
going to increase your infrastructure, you're going to
11:17
want to grow. And at some point it's the
11:19
nature of like capitalism growth that you're always going to be
11:22
stretching yourself and not resting in your laurels.
11:26
So in many ways, it's, it's, it's going to be kind of that,
11:29
that, that tough game unless you want to, I don't want to say
11:33
play small, but like, you need to get to this like flywheel
11:38
breakout success, right? But until you get to that,
11:40
there's always this stress, I guess of that.
11:46
And it's like, I, I say this to people and I, I think it's a
11:49
little less so for us freelancers, but especially
11:52
running a startup, you know, I see my clients, they go from
11:56
like one client's like, I'm shutting down, I'm packing it
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and I'm done to the next two weeks being like, Oh my God,
12:02
this was the most incredible 2 weeks ever.
12:04
And I would go through that. I'm like, I'm worth $100
12:06
million. I'm worth nothing.
12:07
I need to sleep on AI, need to sleep on a friend's couch.
12:10
I'm worth $200 million. I'm going to be homeless.
12:13
Like, where am I going to eat tonight?
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All this stuff. So it's I was like, all right,
12:17
how do I just do this? Like Prozac?
12:19
I didn't actually go on medication, but I'm like, how do
12:21
I just pretend I'm on Prozac? And the highs are here, the lows
12:24
are here. And it's like I'm navigating
12:26
that. Because no matter how bad you
12:27
think it is, given a little bit at a time, it will come out the
12:32
other end. And it's really a signal that,
12:34
OK, is this a signal that things aren't working?
12:38
Or is this emotionally things aren't looking good or like, do
12:44
I just need to give a little bit more time?
12:46
And sometimes it's, it's, it's fuzzy, right?
12:48
But the more clarity you get is like, is this signal that things
12:51
aren't working and I need more leads or I need this or I need
12:54
that? What isn't working?
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Do I need to go upmarket? Like is this effective or not?
12:59
And real tests and real signal, not emotion, but real data,
13:02
right? You work for Uber.
13:03
You guys are very data-driven, right?
13:06
Every city was a new market. Everything had to be data-driven
13:09
and separating from the emotion because the emotions going to be
13:12
like you're going to wake up and freak out.
13:14
But what does the data say and what can you do to calm yourself
13:18
emotionally? And what structures could you
13:20
put in place, whether that's diet, exercise, mental regime,
13:23
whatever that is to really deal with that, right?
13:25
And I, I could go down a rabbit hole, you know, the whole
13:28
personal growth and development thing and what put in place, but
13:31
I think that's a, a long winded answer to, to, to your question.
13:36
I mean, it's a, it's kind of a crazy concept that I'm fully
13:41
convinced unless you go through it yourself, you truly have no
13:45
idea what it's like, right? Only the actual founders who
13:49
went out there and started their own thing from scratch truly get
13:52
it. And so you talked a little, you
13:57
know, you're touching on the setting yourself up for success,
14:01
right? The stress management, the gym,
14:04
exercise, sleep, that kind of stuff.
14:06
I mean, what are the top maybe two or three things from that
14:09
standpoint that you've put in place for your life that have
14:12
been made the biggest impact in keeping yourself sane through
14:15
the roller coaster of ups and downs?
14:17
And you know, transparently like, so when I'm stressed, I do
14:21
a few things right. When I'm not stressed, I'm a
14:23
little, I'm a little less regimented.
14:26
So the first thing is how do I hack my productivity, right?
14:31
My biggest productivity hack is I literally plan every 10 to 15
14:36
minutes. Like it's the biggest meeting.
14:39
So I write down from 7:00 AM to whenever I'm leaving my desk or
14:44
even my whole day to like midnight.
14:45
What am I doing? What am I going to the bathroom?
14:48
What am I eating? Like and regimented with all of
14:51
it. So then I know exactly what I
14:53
could get done that day and I could take my do list and I
14:56
could plop it in and I know exactly what's going to happen
14:58
that day and what's not right? And then I could reprioritize
15:02
according to that. So that's going to the more
15:03
structure you have, the more freedom you have, right?
15:07
So really putting that into place.
15:09
The second thing is get your mental state under control.
15:12
Everybody says I can't meditate. All meditation is is 1 breath,
15:17
even if it's 10 minutes of mind wandering.
15:20
If it's one breath of all you thought about was that breath,
15:24
that's the success. But how do we calm to mind?
15:26
I'm a huge kite surfer these days.
15:27
I used to be a super, I used to be a huge surfer.
15:30
I used to be an Acrobat. I've done some sort of hobby
15:32
always to get myself out of my damn head and into my body and
15:37
just let the world disappear at least a few times a week.
15:41
Sometimes it works. Like that's why the 5:00 AM club
15:44
is a thing. I personally hate it.
15:47
But even if you have to get up at 5:00 AM to give yourself a
15:49
little bit of time to make sure you're getting that that, that
15:52
quiet time. And then I think the third thing
15:55
I could say is there's a book by Cal, no Poor called Deep Work.
15:59
Basically all he's saying is if you could chunk the biggest
16:02
project you have and block off an hour to hour and a half of
16:06
uninterrupted time to get that done, it'll be the biggest favor
16:09
you could do to yourself. So those are the three biggest
16:12
tips I could give you. The deep work thing and the one
16:14
thing I'll add to it that I've done personally is if I plan the
16:19
night before and say, what am I going to do in that hour?
16:23
Two things, three things. One thing doesn't matter if I
16:25
don't do that, I wake up in the morning and I'm like, I have no
16:29
fucking idea what to do. It's it's a crazy phenomenon
16:31
within myself. No 100% right.
16:34
I wake up with it. Especially when I wake up with
16:37
anxiety going on shit and like I sit my ass down.
16:41
Like I literally go pee, brush my teeth, get a glass of water.
16:44
I sit my ass down at this table and I literally write out
16:48
exactly what I'm going to do. And I'm like, oh, OK.
16:52
I give myself structure, right, Right.
16:55
I hate structure. I hate it.
16:57
I just want to be free. But whenever I'm free, I don't
16:59
do shit. The more structure you have, the
17:01
more freedom you have. It's the best quote I've heard
17:03
in the last like five years. Love it.
17:05
Yeah. And what's interesting, and
17:07
yeah, it's different for every person.
17:09
But if I did what you did and woke up and tried to write down
17:14
what I'm going to do, it doesn't work for me.
17:17
Like I have to do it the night before.
17:20
Otherwise I'm a mess. And.
17:21
And I can't tell you why the night before, I'm so clear.
17:24
Like it's easy. The I have a great morning
17:27
routine. I've been writing down that I'm
17:28
going to put in a great evening routine for like forever and for
17:33
the life of me it's like I most of the times it's like I sit my
17:37
ass down. Even if I get home late, I put
17:39
on ATV and I'll fall asleep and then I'll get up like 10 minutes
17:42
later and then brush my teeth and like pass out.
17:45
But me like I'm not a night person.
17:47
I'm a morning person. So trying to like clarify things
17:50
at night. It's what I should do.
17:52
It's great advice. I think it's way better than
17:54
mine. I need to do that.
17:57
One of the things that you talked about is working on the
18:01
right things, right, actually prioritizing what moves the
18:05
needle. And it's a perfect segue from
18:08
the deport conversation, but especially for fractionals, for
18:12
independents listening to this. Yeah.
18:15
What is the one thing, two things that are most important
18:19
for them to actually move the needle in their businesses?
18:22
OK. The first thing I want to say is
18:23
cash is king, right? You got to look at, at what's
18:28
actually moving the needle, right?
18:29
And you got to look at their data and everything's a test,
18:33
right? Everything's an experiment.
18:34
That's the biggest thing I could say from the startup world is
18:37
the companies that live or die. They, they're the ones that the,
18:42
the, the ones who fail are the ones, oh, I think this, I'm just
18:45
going to go do it and I'm not going to give any feedback loop.
18:48
And the ones that succeed overwhelmingly are the ones
18:51
like, let's run a test. What does the data show us?
18:54
Could even be an informal test. But how do we learn from what's
18:57
not working right? And I think that's one, one of
19:01
the biggest things that I take into this from, from startup
19:04
world is like, how do I just listen to the data?
19:07
How do I listen to feedback? How do I, you know, people tell
19:10
us all sorts of opinions, but how do I take that?
19:12
And it's like, oh, that's gold. Let me incorporate that.
19:14
Let me let me get more wins here.
19:17
But like, even going a step deeper is like, OK, we all want
19:23
top line leads and we all want to find the perfect customers at
19:25
the perfect time. But like when we actually speak
19:28
to people, what's working, what's not working?
19:32
Are we getting the second meetings?
19:34
Are we closing? Is is our follow up
19:36
documentation or proposals? Are they being effective?
19:40
Like are people like what? Where is it breaking?
19:44
Like what's not working? Let's go fix that.
19:47
Yeah. Well, and notice, right, you're
19:49
talking all about sales and new business, right?
19:53
You, you, you said cash is king. It's about finding new business.
19:56
Most consultants don't like doing that.
20:00
It's a lifeblood of the business.
20:02
It's like, OK, great. You know, for me, I'm like, it's
20:06
everything. I mean, we can operationalize
20:08
everything and it is about delivering the product or
20:11
delivering the product. If if delivering the product was
20:14
hard, I'm pretty sure we wouldn't be doing what we're
20:17
doing right now, right? It's probably our natural spot.
20:20
So I say that I have this quote that I tell the to technical
20:24
founders all the time and I go, let me ask you something.
20:28
Are you dreaming about your product every night they go,
20:31
yeah, I'm like, are you? Do you have, like the next two
20:34
to five years built out in your head of what you're going to do?
20:37
Like, yeah, I'm like, great. So you don't have to think about
20:40
that shit ever again. And all your time and your
20:43
resources are on sales and biz dev.
20:46
The end of the day too right is around.
20:49
It's with AI it's never been easier and it's only going to
20:54
get easier to build whatever product you want.
20:58
Yeah. Right.
21:00
And and we know from a services perspective how many people have
21:02
become independent fractional in the last four years with COVID.
21:06
I mean it exploded. We're talking about millions of
21:09
people literally went out there are out there now.
21:12
OK, so let's just assume to some degree we're all a commodity.
21:15
We all delivered the same either service or product, which is not
21:18
true. But let's just say for sake of
21:20
discussion, what then separates the winners?
21:24
I don't want to say from the losers because it's not a win
21:26
lose game, but from the people that really win.
21:28
Like what separates them? So I think it's a few things
21:31
right? One the the the canned answer is
21:36
positioning is branding, right? It but that's one thing.
21:41
But getting down, it's like, how are you going to build rapport
21:44
and trust, right? Tony Robbins has a great quote.
21:47
I don't usually quote them, but people only buy from people that
21:50
they like, know and trust, right?
21:53
So the sooner you can get somebody to know you, like you
21:57
and trust you, they're going to buy.
21:58
And the second they know that you could deliver, they'll buy.
22:03
But it really comes down to giving an overwhelming amount of
22:08
value because if you over deliver and there's something in
22:13
startup work called Net Promoter score, bottom line is you reach
22:17
a certain number in a survey and people are raving to their
22:20
friends about you. You don't want to be lower than
22:24
that because then they're just like, meh, they never talk about
22:26
you. And you certainly don't want to
22:28
be lower than that, because then they're talking shit about you.
22:31
Right there, I'm seeing as you talk this cycle, right of get in
22:35
front of people, of course, deliver value.
22:38
Value builds trust and the likeness that you talked about.
22:42
And then when they trust and like you, they buy from you.
22:44
Yeah. And then when they love what you
22:46
bought, as you said, they rave about you.
22:49
Yeah. And then, you know, we all know
22:51
referrals are the best way to build a trusted relationship
22:54
because it's just the the trust has passed, passed on.
22:58
Exactly right. So I focus a lot of my time on
23:01
referrals. I focus a lot of time on
23:03
connections. I focus.
23:05
I mean the the best customers I've ever gotten were from
23:08
referrals. My longest lasting customers
23:11
were from referrals. So that's where that's where I
23:13
spend a lot of my time for better or for worse.
23:17
I'd love to crack the Facebook marketing game.
23:20
That was a lot of tears and I think I actually I'm up five or
23:28
10K from all that, but not if you count my time.
23:33
You're right. Right.
23:34
How much effort? Yeah.
23:35
Yeah, not if you count my time. And then, you know, I was
23:38
talking to somebody about doing like organic and stuff like that
23:42
and I'd love to crack the code with it.
23:43
I have not cracked the code on that to be perfectly honest, but
23:47
what I am naturally great at is being in front of people and
23:51
having a VC fund and traveling the world.
23:54
I meet a tremendous amount of amazing individuals who run
23:58
funds and family offices and all sorts of things.
24:01
So then doing referrals to their their startups and stuff like
24:04
that has been tremendous as well.
24:06
Yeah, it was kind of interesting at the beginning, before we got
24:09
online, I asked you what you do for marketing and you're like,
24:12
oh, you know, nothing really. It's just word of mouth and
24:14
referrals. And then I was like, well, how
24:15
do you get the word of mouth and referrals?
24:17
And then you're like, oh, I do all this networking at
24:19
conferences and, and meeting people in introductions.
24:21
It's like, OK, that's actually a huge amount of marketing right
24:24
there that you do. It's just not traditional, you
24:26
know, content. Or whatever.
24:28
Yeah, there's I mean, you got to remember there's 138 different
24:32
ways of marketing 138 right? You can look it up.
24:36
Maybe ChatGPT will take 136 or 180.
24:39
I don't know. But there's a lot right And so,
24:42
but yeah, networking, you know, somebody's like, oh, you should
24:45
do B and I Oh my God, please no, never again.
24:48
But or like you should join the chamber.
24:51
I'm like, OK, but I think for I think there's certain fields
24:55
that stuff works for, but finding a niche and finding a
24:58
room that is going to be target rich or refer rich and I don't,
25:03
I actually don't want to be in front of a target audience
25:06
because if I'm in a room with startup founders, I'm actually
25:08
like, I'm hurting after I really am.
25:12
I'm sorry, if you're a startup founder out there, I love you to
25:15
death, but I'm hurting if it's a room with you.
25:17
But if I'm in other people that can refer me, those that are
25:20
trusted partners that that room is, is something special for me.
25:25
And I try and find those rooms and I try and now I'm like,
25:28
where do I put my energy and intentions so I could be full on
25:31
one of those rooms? Right, so you have found this in
25:34
person conference, networking, introductions, word of mouth
25:37
game is very effective for you. It's the most effective thing I
25:41
have gone on yet. Now, by the way, the one thing I
25:43
need to add and nobody's going to people are going to call say
25:47
I'm full of shit is I'm an introvert.
25:49
I'm an introvert. I grew up super shy and not that
25:53
this, this is like you're getting the authentic me, but
25:56
like I and when I mean introvert, it means being out
26:00
there is a net energy loss for me.
26:03
So I'm even more particular when I network of being intentional
26:06
with that. So anybody could be put out
26:09
there. If you met me when I was 12,
26:11
like I, no, I, I wouldn't want to talk to anybody.
26:14
I'm also. An introvert myself, and which
26:17
means, as you said, I recharge by being alone, right?
26:20
That's to me the definition. What I used to think it means is
26:23
that like I don't like talking to strangers which is bullshit
26:27
right? That's just a fear driven
26:29
response of I'm afraid of the awkward conversation or not
26:32
knowing how to approach it or they'll reject me or whatever.
26:35
That has nothing to do with introvert extrovert.
26:37
No. I learned that more recently,
26:39
but it's, it's a good one. So that's why people say you're
26:42
going to, that's why you said people are going to say you're
26:45
full of shit because they they think that they're an introvert
26:49
because they don't like talking to strangers, which really means
26:51
they're just scared about talking to strangers.
26:53
I've seen the most awkward, I've met a few individuals that like
26:59
are the most spectrumly awkward humans.
27:03
And there are all these conferences and they're some of
27:06
the most successful people. So if they could be out there
27:10
like and be fine, anybody really can.
27:13
I mean, truly, it's just about being yourself.
27:15
Go there, have some fun with it makes it I mean.
27:19
And, and and you know, it's, it's funny, I I had to deal with
27:22
this for a while, Like I have a coach.
27:24
I've had a coach for a long time, personal growth coach
27:26
slash business coach, and for the longest time and I still
27:29
don't understand it. But like people are like we
27:32
really like you, Rob. We we really get along with you
27:35
and this and that. I'm like, I don't know why I'm
27:37
like, I just don't, I'm like, I don't know, like my Genesee qua.
27:40
I'm like, I'm just me, like you love me, you hate me.
27:44
Like cool. But the feedback I get when I
27:46
ask that is like, well, I'm authentic and I'm vulnerable.
27:50
And as long as I'm authentic and vulnerable, people gravitate me
27:53
because nobody wants to be around somebody who's bullshit
27:55
or full of shit, right? And especially I live in Miami
27:58
Beach these days, the biggest challenge I have down there.
28:01
I love it, don't get me wrong. Not complaining just a little
28:05
bit, but being around real people and you, you, you tend to
28:08
get it. Like when you're in New York,
28:09
it's like, oh, you work for Goldman.
28:11
Cool. I know what you do.
28:12
You're a known entity. I, I, I get, you're doing really
28:14
well. I know how you made money down
28:16
here. It's like it'll be anything.
28:19
So it's like being real around real people.
28:21
It's like it's it's everything and that's across the globe.
28:24
So anyway, sorry for my my tangent.
28:26
Curious with the vulnerability piece, like what?
28:30
What does that mean to you? To show up vulnerably, let's
28:33
just say at a conference or meeting someone new?
28:35
I mean, the definition of vulnerability to me is like just
28:38
being open is like you don't, I don't have to put on like some
28:43
things are really difficult, right?
28:44
Some things really aren't working right and just being
28:49
real with people that that is like, I'm definitely human.
28:52
I definitely have my own demons. I definitely have my own
28:55
challenges. I think I have to remind myself
28:58
of how good I have it. But I definitely have goals that
29:01
I haven't achieved. And as long as I'm real with
29:04
people like the good, the bad, the ugly, and sometimes show the
29:08
ugly, you know, one of the reasons I, you know, sharing
29:12
that I'm dyslexic and I didn't read to, I was 10 years old.
29:14
That's to me for the longest time that was super
29:17
embarrassing, right? I didn't think I was smart.
29:19
I thought I was stupid, right? To me, like I was like, Oh my
29:23
God, like, how could I share? Let anybody see, you know, And
29:28
people destroyed me when the teachers asked me to read out
29:30
loud. Even today, I'm like, you know,
29:33
and like I'm MCA conference in three weeks and it's first time
29:36
I'm seeing obviously I'm decently spoken.
29:39
I curse a little bit, but like the thought of emceeing, I
29:42
almost said no because I was like, I have to read in front of
29:46
like 500 people and get everybody's names right.
29:49
And I'm like, to me that is like, this is going to be so
29:52
confronting. Like, let me tell you, it's
29:54
going to be another, another little breakthrough.
29:56
But I'm going to, I'm going to sit there and I, I usually wing
29:59
stuff like I'm like, ask me anything.
30:01
I'll, I'll go for it. But now I'm going to actually
30:03
have to sit there and study and know my script.
30:05
So it like it just rolls off. So I'm polished.
30:08
Otherwise I'll feel like an idiot and then it'll snowball
30:11
and I'm like go to just spiraling and anxiety.
30:14
So it's, you know, but that's the real, that's what scares me,
30:19
not public speaking, public reading.
30:21
I love it. I mean, I, I just, I want to
30:24
acknowledge well. I I I don't love it.
30:27
I'd love to share. That's what I'm saying.
30:30
And the willingness to get uncomfortable by getting up
30:35
there and emceeing the event anyway, right?
30:38
I just, that's a growth opportunity.
30:40
And as you said, it's kind of it's kind of an edge and it's a
30:43
breakthrough that some of the things, I mean, some people even
30:47
on this podcast come to me and they're like, I'm terrified to
30:49
post on LinkedIn, just like terrified, right?
30:52
For all the list of reasons. And it's like, cool, what do you
30:56
want to do about that? You can either let the fear
30:58
prevent you from doing it, prevent you from marketing
31:00
yourself and getting yourself out there, or you can
31:02
acknowledge the fear and do it anyway.
31:05
Yep. You two options, right?
31:07
Yeah. No, exactly.
31:09
By the way, I hate posting. I felt like my Instagram's
31:13
private again, Like there's just so much about it that I, I, I
31:16
can't stand. Like I used to do all these
31:19
reels. You'd probably find a bunch of
31:20
those reels, but I did hundreds of reels and some of them were
31:25
cringe worthy. Nobody else saw their cringe
31:28
worthy. I wanted a cringe right, right.
31:30
And you know, and then I was like, Oh my God, how many likes
31:33
did I get? Oh, I didn't get that many
31:34
likes. I'd feel less right It's but
31:38
it's Prozac again. Prozac.
31:40
Prozac yeah, I always tell people if you record a shitty
31:44
reel or write a shitty post, nobody sees it.
31:49
This is also true. Right.
31:51
Like I have an audience of like 23,000 on LinkedIn and I've
31:54
literally written a post. I got 0 likes and I have like 50
31:57
impressions, which is actually kind of challenging to do if you
32:00
really think about it. And I was like cool, that post
32:02
was so bad not a single person engaged with it, which means no
32:06
one freaking saw it. Yep, except the one.
32:09
Probably the one person who didn't want to see it did see it
32:11
though, because that's no idea. I will tell you unless I piss
32:15
someone off, which I have before, but no one has ever no
32:18
one has ever come to me and said that post you wrote, yeah, that
32:23
was really shitty. Never they disagreed with me.
32:27
I pissed them off by like a, you know, claim I made sure, and
32:32
that's fine. But no one has ever been like
32:34
that was a piece of shit content ever.
32:38
So, you know, again, they can disagree with me and that's
32:41
fine. But all right, last question.
32:44
And then we got to jump. But productizing a service, it's
32:48
such a cliche, it's such a phrase to create scalable
32:52
revenue. But to you, Rob, what is
32:55
productizing a service really mean?
32:57
I just went through it, right, because I was like, I hired
33:00
somebody. He's like, we're going to do
33:01
100K and 300 KA month and it's going to be great and we're
33:05
going to get 30 clients a month and you're going to have 300 a
33:07
year. I'm like he's like, you can't do
33:09
that by a loan. You got to have like cohorts.
33:12
I'm like, all right, cool. So let's productize this, right?
33:14
And how do I actually sit down and codify what I do and how do
33:19
we actually make this? You know, and what, and I listed
33:22
out like 80 different things and I'm like, I'm like, I can't have
33:26
an 80 week program. And I kept whittling it down,
33:29
whittling it down. I was like, all right, let's do
33:30
a 24 week program. But I really broke down.
33:34
What are the core elements of what I did?
33:35
What difference do I want to make?
33:37
How do I get that across and how do I bring people through
33:40
through a process? Now from those 80 things, I got
33:44
4 pillars and from those 4 pillars, I really was able to
33:47
redefine how I even spoke about what I did right.
33:52
So that exercise right there redefined my business.
33:55
But then I also had the have the ability to really push people
34:00
through in a, in a cohort, like in a huge impactful way to
34:06
really make a difference for them.
34:08
And, and, and creating those systems.
34:11
By the way, it's also easier than ever right now because
34:13
having a conversation with Chenchi PT or Claude or Gronk or
34:17
whoever you want to talk to and, and how to really organize that
34:22
is, is really, it's just such a huge tool in the toolbox.
34:28
Yeah, one thing you'd leave our audience with anything.
34:32
Two things. How about I'll re say my quote.
34:34
The more structure you have, the more freedom you have.
34:36
And the darkest part of the night is right before dawn.
34:43
How would you translate? Yeah, go ahead.
34:45
The darkest part of the night is right before dawn, right?
34:50
So literally it's going to be as dark as it could be and as you
34:55
could be at your bottom. And then you're right there and
34:59
you see you find that breakthrough or the other, the
35:02
other quote to that is the biggest failures in life never
35:06
know how close they were to success, right?
35:08
There's a little pick up. There's a little GIF of like the
35:11
guy like cracking away at like a diamond seam and he's like right
35:15
there and he's walking away, right.
35:18
So if if you're looking for if like you're pounding away and
35:24
you're like right there and you don't know if you're right
35:26
there, but you just if things aren't working, I'd say this one
35:29
is look at what really isn't working, what what is and then
35:34
just keep at it and push another month longer because or two
35:39
because it could just be right around that corner.
35:42
Where can people find you if they're looking to get in touch?
35:46
It's my name, robmadskin.com, Rob Madskin at Gmail, Rob
35:51
Madskin at insto or LinkedIn. But just reach out.
35:55
Always happy to support, always happy to lend some advice or a
35:58
helping hand and if I can make a difference for you, let me know.
36:03
Amazing. Well, Rob, thank you so much for
36:05
the time and the insights. Great to have you on.
36:07
Hey, thanks for having me. This is great.
36:09
Really appreciate all the questions.