#1: This Sucks—How Can I Make Money from It? The 8 Mindsets and The Art of The Pivot with Jason Meyer

What if your biggest setbacks could be the secret to building wealth and resilience in your law firm?

In today’s episode, I sit down with Jason Meyer, a lawyer-turned-entrepreneur with a rare perspective on how to thrive when things suck. Whether it's an economic downturn, getting laid off, or a client crisis, Jason shows us that the key to long-term success often begins with one question: How can I make money from this?

We dive deep into:
• How to flip pain into profit (with real examples from the financial crisis, the pandemic, and today’s market stress)
• Why most law firm owners overlook their most valuable mindset—and how to unlock it
• The 8 essential mindsets that help entrepreneurial lawyers lead, pivot, and scale with confidence
• How to use empathy, storytelling, and systems thinking to stand out and serve your clients better
• The surprisingly powerful role of creativity and resourcefulness in legal practice
• What The Art of the Pivot really looks like for modern law firm owners—and why it's the difference between survival and success

This episode is a must-listen for any legal professional ready to think beyond billable hours and start building real leverage.

By the end, you’ll walk away with a playbook for embracing chaos, doubling down on your strengths, and leading with a mindset built for the long game.

Let’s turn the suck into strategy—and strategy into revenue.

Jason is a business lawyer, career entrepreneur, and a Certified Compliance and Ethics Professional (CCEP). He is the Founder and Principal Lawyer of Princeton Business Law, a boutique firm dedicated to meeting the legal needs of small and medium sized businesses (SMBs) and the entrepreneurs who run them. Jason’s background includes founding LAWCAST, a nationally accredited CLE provider; serving as Chief Legal and Ethics Officer for one of the first major providers of compliance e-learning; and leading a $50 million ethics education business. Jason is a graduate of Princeton University and the University of Pennsylvania School of Law.

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Transcript

So one of the things that I immediately recognized about you was your entrepreneurial mindset
0:06
and I so we came up with the topic of this sucks how can I make money off of
0:13
it yes this sucks how can I use this to make money to make money yeah so the combination between you know your
0:20
entrepreneurial side coming through and then also this mindset that is so rare i'm like we have to make an episode so
0:28
start with telling us your story about how you came to embrace these mindsets
0:33
sure and Chelsea thank you so much for having me on and it's it's really been so great to talk to you and uh and to
0:40
get to know you and and delighted to spend this time with you and you know and to talk about what the strange
0:45
things going on in my head um so yeah I you know I I came out of big law but I
0:52
also come out of a family of entrepreneurs and spent time myself running companies i I I left the big law
0:58
firm to start a company with my wife that that we ran for more than 10 years
1:03
i spent time in house both as a GC and uh later you know purely in a in a sort
1:10
of executive general manager type role for a for a big operation um and you
1:16
know born of that was sort of like trying to marry sort of the way I think as an entrepreneur and the way I see
1:22
other people think as an entrepreneur and as a business person with the skills and requirements and and things I got to
1:29
do as a lawyer and and part of what I realized was hey I see I keep seeing this thing going on and it's this sucks
1:37
how do I use it to make money um and I've seen that in in my client my you
1:43
know my longest client and a dear friend uh made his fortune because his software
1:49
company came up with a fix for the Y2K bug you know Y2K the whole Y2K thing
1:55
back in your childhood um you know that looked pretty scary it sucked and he used it to make money um you know there
2:03
there was a time when we drove in our cars and all we had was the radio and we went for walks and we had to listen to
2:10
music but what if I wanted to learn what if I felt lonely and what if I wanted to hear other interesting people and that
2:15
kind of sucked and now there's podcasts right this is this is the idea um and
2:23
the cool thing is it's also kind of the idea behind behind my law firm Princeton Business Law um that we started it i
2:30
wanted you know I wanted to be a law firm for you know people who thought oddly uh or differently the way that I
2:39
do as an entrepreneur and who wanted both uh you wanted legal advice top-notch
2:45
legal advice i've been you know I've been through the big firm in the GC world um but also wanted it so that it
2:52
fit entrepreneurs and the mindsets and the law firm and everything I hope blend
2:57
together to bring that about um but you know what occurred to me is uh how often
3:04
in entrepreneurship opportunity is born of a problem a setback a crisis right
3:10
that's what's the saying never waste a good crisis right and even the thing that you know the the very old saying
3:17
from you know from before my time right you know build a better mousetrap and the world will beat a path to your door
3:24
it's like well I'm only building a mousetrap because I've got mice
3:30
that's that's the idea i love it and my version of that of this
3:36
sucks how can we make money from it so I have kids and my daughter when she was
3:42
younger we used to watch and love that movie Robots i don't know if you've ever seen Robots okay so the entrepreneurial
3:48
robot has a mantra and he's like "See a need fill a need." And that is his
3:54
business motto it's like when something happens be the solution um and that can
3:59
be profitable and I actually just did a podcast episode it hasn't aired yet um
4:05
for my other podcast about the current economy and how people are completely freaking out and you know they're
4:12
feeling the stress and they're taking on the fear and the theme of that podcast was the same exact thing it's like there
4:18
are absolutely people seeing opportunities right now taking advantage of them and profiting from them
4:26
and again one of the things that I really appreciate about you and how your mind works it's not weird it's actually
4:33
how we thrive and I think in my experience working with so many lawyers
4:39
over my eight-year now career law school didn't teach them entrepreneurship in
4:46
fact I think some components of law school make it more difficult to identify and adapt the entrepreneurial
4:53
mindset can you speak to that challenge yeah totally i I I think I think that's right uh
4:59
particularly now I haven't been to law school in a very long time i'm I'm about to go to my law school reunion um and
5:08
and so things have changed and you you see entrepreneurship much more in the education system even in even in elite
5:15
colleges and universities there you know there is more entrepreneurship when I went to law school I I went to I went to
5:21
University of Pennsylvania I had to go across to the Wharton school to get a class in entrepreneurship um I think I
5:28
think things are more blended now but there is still something about what I
5:34
think of as the big moving sidewalk uh that as a law student and as a young
5:40
lawyer it's really easy to step on that sidewalk and it pulls you off in a direction and you didn't know you were
5:45
heading in that direction and you couldn't get off but but it feels that way right like I'm pulled into big law
5:52
like I'm you know I'm pulled into the realities if I if I join a trial firm of of what that's all about and it is hard
6:01
to look around and see the other opportunities and to think of yourself as an entrepreneur i think the
6:07
advantages for new lawyers and younger lawyers now is growing up in a world of
6:13
social media personal branding we all have profiles we have
6:18
LinkedIn most of us do uh we're where you know you're already thinking about I
6:24
have a brand i am my own business i don't know that I'm going to be in this firm forever i don't know that I'll be
6:30
practicing this kind of law forever i have to make my own opportunities i think that comes a little more naturally
6:36
in this communications environment but there is still something about law
6:42
school and also something about what is frequently
6:48
called the practice of law for entrepreneurs that you hope to learn off of and that is a lot of the time it's
6:54
really about venture capitals about venture capital companies representing VCs representing private equity
7:01
interests and those are actually larger money interests they have their own way of doing
7:07
things frequently I represent founders i represent the actual business owners and
7:13
operators i certainly do work for for private equity interests too and love it and happy to have them but the work I do
7:20
for founders has led me to realize that a lot of what comes out of big law firms
7:25
on behalf of quote unquote entrepreneurs is really documentation for the investor
7:31
class and that makes it more complex more opaque than it needs to be and and tends
7:40
not to be profounder in its meaning so one of the things that that I do in my firm is to try and get those documents
7:47
to be more about the business owner and the founder and their rights but that
7:54
atmosphere as people start legal careers and look to develop legal careers can can cloud it right just like when you
8:00
say entrepreneur people think Shark Tank but Shark Tank unicorn style companies
8:06
are like you know a percent of the world of entrepreneurship most entrepreneurial companies are
8:12
bootstrap you know maybe family-owned or friend-owned companies they can be making a ton of money they can be doing
8:18
really well and they have no interest in bringing in outside investors or flipping the business right they're
8:24
making money by being a company and solving the problem
8:29
and that's harder to see from a law firm seat um I'll I'll if you want to hear it
8:36
I'll tell you one more anecdote which is so again I went to law school decades ago
8:41
okay and at the time I was the only person in my law school class who had been in and run a
8:48
business before I went to law school i think that it's not quite as unusual now as it was then but at the time I was the
8:54
only one and I remember on like the second day of contracts class the professor was talking about non-compete
9:00
agreements and how they worked and you know as basically asked the
9:05
question why would anyone enter into a non-compete and I sit back I I deliberately I remember this really
9:12
clearly I like sat back and waited and everyone's how could anyone sign this it's ridiculous anyone who reads this
9:17
would know it's an infringement on your rights and you know you can't go to work and how can you stand for this why does
9:24
the law permit this and you know there was sort of all this law student outrage and finally I raised my hand because no
9:30
one else was saying it and I said the reason that a worker would sign a
9:36
non-compete agreement is they need the
9:41
job they need the work and if the boss says "You have to sign this to get the job," they will say "Where do I sign
9:47
boss?" Because I need the paycheck and somehow that had not penetrated into law
9:52
school now I think that's different now i I think I think there are many more students who go out of college they work
9:58
for a while they come back to law school and man they know the meaning of a paycheck but that still has stuck with
10:04
me in terms of making sure we look beyond what we
10:09
think lawyers do to what our clients need and and and that's
10:15
something that you and I'll probably keep talking about uh because to me it also comes down to the way your work
10:21
product works yeah absolutely and I know we have a lot of listeners who are around your age
10:28
it's not something and I love that college is evolving and the experience is evolving and they're incorporating
10:34
this more entrepreneurial side to things and starting to think outside of the box
10:40
but for the people who did weren't able to have that experience I want to go back to the this sucks how
10:47
can I profit off of it because I think this is where we can help them shift that perspective and give them some
10:54
insight into how to think like an entrepreneur and so I know you have a
10:59
lot of stories that can serve as proof and show the line of thinking the creativity that solved the problem in a
11:07
profitable way but what is some of your experiences that you've been through or that your clients have been through where it was like this sucks how can I
11:13
make money off of it something I there there's I mean I first
11:20
I'll tell you some of my story I guess which is so uh what's something that
11:26
sucks getting laid off sucks um and and uh on the other hand you know people a
11:33
lot of people got laid off in the great financial crisis uh you know 2008 to 2013ish me included twice um
11:43
uh and a lot of other people got laid off and a lot of those people got laid off started their own businesses and the same thing happened in the pandemic by
11:49
the way and you know the pandemic sucked big time um and a lot of people responded to it by saying
11:57
uh I'm working from home and this is okay and maybe I'm just going to go off
12:02
on my own now uh and maybe I got laid off and I have to go out on my own now what am I going to do sitting here in
12:07
the living room so those hardships gave birth to companies and it was like that
12:14
for me i I I worked in I worked in in very senior positions uh making a lot of money for my
12:20
companies uh each of which you know sort of decided they wanted a better quarter
12:26
and a good way to do that was to say goodbye to Jason um I've seen that movie
12:31
now i've seen how that movie ends and I didn't want to see the end of that movie again but I I liked the times when I
12:37
worked for myself i like building my own team and running my own team and also I
12:43
thought you know I have I have I have experience that I can bring to other clients to other entrepreneurial clients
12:49
in terms of this is how things are done inside companies this is what happens in big law firms how do we bring that to
12:54
the world of entrepreneurship entrepreneurs have their own risk threshold and profile
13:01
they have their their risks they would take larger companies would never take like they'll bet on their success every
13:06
day of the week there risks bigger companies would take that entrepreneurs won't take like cash flow risks it's
13:12
it's a different way of thinking every business every legal question rather is
13:17
a business question every question you know Jason what do I do about this is
13:24
what do I have to do what can I get away with not doing what's going to do best for my business model uh it's it's mixed
13:31
questions of business and law and it occurred to me I can help people solve those problems i can build a business
13:37
around that and that was me saying things that sucked and some stuff that sucked for me and and trying to go on
13:43
from there i think you know the other the other example I would give is so I
13:48
actually started two companies uh uh after the financial crisis one was this law firm and the other was a consulting
13:55
company because I came out of the world of corporate compliance actually had developed a reputation as a thought
14:01
leader in in compliance education over that you know 101 15 years in that
14:06
industry picked up my credential as a certified compliance and ethics professional i wanted to use that and
14:12
some of the people who wanted me to do that didn't want to hire a law firm they just wanted what was in my head so I
14:17
started a consultancy also because the ethics rules of my state are such that I
14:23
cannot consult out of a law firm and a law firm should not be offering pure consulting practice so I needed to start two companies and over time they've
14:31
pivoted one's taken the lead one's taken the back seat coming out of the pandemic
14:37
a lot of the work for my consultancy went poof right there weren't big there weren't a lot of people getting together in one place for corporate training
14:43
anymore uh there there you know were not big training events there were not big
14:48
contracts the kinds of stuff I did from my consultancy lead good went away I pivoted my consultancy to focus on
14:55
neurode divergence in the workplace which which is another whole conversation we can have but I also saw this wave of
15:03
entrepreneurs starting put the law firm in the lead and the law firm's grown great over the
15:11
last five years because of that and and that was because we had on you know my team and I had hands-on entrepreneurial
15:17
experience had a lot of it topflight legal training and expectations and I think the other thing
15:23
that that goes into the attitude of the entrepreneur and if I may say the attitude of of the firm I'm building is
15:32
that you're a closer and I realized this from my times as a general counsel and I I was I was
15:40
chief legal officer for a software as a service company and you We had sales people and big sales teams and they went
15:45
out and did stuff and the end of the selling process was getting the client to sell a software license agreement
15:52
which put me in a room with the buyer and the buyer's lawyer negotiating the
15:57
software license agreement and it occurred to me I'm the closer for this
16:02
company it's like like like if I if I negotiate this contract long wrong wrong
16:08
we lose the sale and uh that's not the idea and and so that helped me realize
16:16
that for companies not just entrepreneurial companies the contract with your client is the closing activity
16:25
and that contract better not scare off the clients it needs to be written in a way where the clients know what's going on
16:31
and that is another you know that's another thing that's really sort of guided you know I think guided what
16:39
we're trying to do as a firm um and there's there's something I
16:45
realized about mindset Chelsea um that that's kind of a pep talk I have
16:51
to give myself from time to time and that I have to give my clients and I guess that I would pass along to your
16:56
listeners which is you know if you do a SWAT analysis of your own entrepreneurial business of your own
17:03
small firm right you're going to come up with weaknesses like we're small we
17:09
don't have a lot of resources we do a lot of things by the skin of our teeth we have to make a lot of decisions on
17:15
the fly at the last minute without complete information and then you list your strengths and it's things like well
17:21
we're nimble we're agile we're resourceful we're we're used to making
17:27
you know you you the thing I always say is like you know you give us lemonade and we make nuclear reactors you know um
17:36
uh and when you look at that SWAT analysis you realize wait a minute my weaknesses are my
17:41
strengths it's just the opposite side of the same coin the fact that we're small
17:47
and we're resourceful is what makes us nimble and agile agile right
17:53
so you you have to remind yourself that this is who you are this is the
17:59
field you're on and I could kick myself for that stuff or I could celebrate it i
18:05
could say "Yeah it sucks and this is how I'm going to make money from it." I love that and what I'm thinking over
18:11
here as you're talking about all of these things is like first of all it's never as bad as we think it is if it's
18:17
not the oh wait financial crisis it's COVID if it's not COVID it's the current economy like it is always going to be
18:25
something and so that's kind of where complacency is dangerous right like as
18:31
an entrepreneur part of your what we have to figure out how to do is how to
18:37
pivot like you said and even in these like right now we just created a
18:43
mastermind for immigration law firm owners because of everything that's going on in that space and a lot of what
18:51
these law firm owners are finding are is that yeah this big thing happened and
18:57
what it's doing actually it's not really new it's not necessarily that something new is happening but what it did do is
19:04
it stress tested our weaknesses and it broke and now we have to fix them and so
19:09
at the end of all of this they're going to come out stronger because like you said their weakness is their strength
19:15
and they expose the weaknesses and they're going to make that their strength you know once they get
19:22
everything patched up and so yeah the art of the pivot so you
19:28
have these um eight mindsets that I don't I want to
19:35
give us enough time to talk about all of these because I love your eight mindsets so talk about how that came about and
19:42
let's start going through them yeah so so in the in the consulting corporate
19:47
compliance world um is where the the eight mindsets first
19:53
came up and and I I work a lot with with uh my dear friend Nicole Rose who's
19:59
based in Australia she's also an entrepreneur and lawyer and educator and
20:05
also just super creative and and you know she she has her businesses and
20:11
thanks to you know thanks to the pandemic and the technology it gave
20:16
birth to here I am working regularly like you know on a on on a almost daily
20:21
basis for sometimes with another professional in Australia and we're like making cool stuff together and uh we now
20:28
do a podcast together called the eight mindsets podcast and there's a companion website conveniently called the eight
20:34
mindsets um that is about these ideas we came up with and and the eight mindsets
20:41
are a crystallization of the way we thought about leading and educating and
20:47
doing persuasion within an organization but as an entrepreneur and
20:53
as a lawyer for entrepreneurs I realized hey there there's more to these eight mindsets this is this is really
20:59
generally about leadership and it is certainly about the pivot and the way we
21:06
can keep our eyes open to see the pivot the way we can decide how to pivot and
21:13
the way we can approach that pivot with confidence and I think with a better chance of success and it still kind of
21:19
boils down to these eight mindsets so they I I'll rattle them off and then we can we can break them down how I think
21:25
they apply in this world if that's good okay so the eight majads are the So I'm
21:30
strapping on this mindset these are like the glasses the binoc you know not binoculars but like the the glasses the
21:36
viewfinder I'm looking through at the world through so it's the mindset of the entrepreneur the audience
21:43
storytellers marketers producers collaborators program executives and
21:50
buyers and it it's kind of a loop and we come back to the mindset of the entrepreneur so I'll break that down if
21:56
you want right so obviously the mindset of the entrepreneur it's all about the mindset of the entrepreneur in some way these are all mindsets of the
22:04
entrepreneur um but the idea behind all of them is hey innovate with what you
22:09
got uh exercise creativity resourcefulness agility resilience like
22:16
embrace those things as I said they are they could you may think of them as your weaknesses they're also your strengths
22:22
um you know that's the hand you're dealt use it
22:29
um that is you know that's the mindset entrepreneur and and the thing as people
22:36
who are leading law firms we have to remind ourselves about okay guys are offer Yeah go ahead please oh sorry I
22:43
didn't mean to I have a specific question on that one um because I I love
22:49
your your description here like innovate with what you have utilize creativity
22:55
utilize resourcefulness innovation agility and resilience and it's never a lack of resources only a lack of
23:02
resourcefulness right and one of the things that I see because my my question to you is what do you see in law firms
23:10
specifically that stunt their creativity and their resourcefulness
23:16
wow um first I don't want to pretend that I've got perfect vision into the into
23:22
the life of other law firms i've built myself my own nice cocoon thank you very much and uh and and and life in here is
23:29
is very nice some of the things I see are are
23:34
again our mindsets um and and and in a way this this goes over into the second
23:40
mindset which is remembering to strap on the mindset of your audience the mindset of your client base um if you're
23:48
persuading the mindset of the learner life is about them it's not about you
23:53
and I think a mistake that lawyers make frequently particularly coming out of
23:59
education and maybe big firm training that we talked about is you know well I I need to I need to sound like a lawyer
24:06
right client comes to you and says hey can you can you help train my employees on this it's like well yes I'm the
24:11
lawyer so I'm going to train your employees by telling them about the individual subsections of the Civil Rights Act and and give them you know
24:19
citations as I do it because that's what lawyers do that's what lawyers do no human being thinks that way outside of
24:25
the law firm okay it does not matter to the worker in a company what the section
24:31
number is um what the what the you know what the actual legal language of that
24:38
sentence is and frankly if you think about your audience you don't want them making those legal rulings you need to
24:45
give them much more easily digested shorter nuggets for how they pretty much
24:53
stay out of trouble and mostly when they need to know to go ask somebody who's
24:58
the expert that's the challenge but as a lawyer my head's all in my head's all in
25:05
you know the blue book and and how do I make those citations and there's a lot of stuff about trying to sound like a
25:11
lawyer if I find this in templates right everyone talking oh go to template you
25:17
know there are all these templates now and you know use what you can get off Alexis it's like yeah okay that's a
25:23
starting point but you know what those all sound like you know those sound like the kinds
25:29
of contracts that go into a file and no one ever reads them and no one ever uses them and we have to sign something and
25:34
you know if there's ever if there's ever a lawsuit we're you know we're protected eight ways from Sunday but this is not a
25:41
document for a closer right so that is one of the ways I think a typical lawyer
25:47
attitude gets in the way i think another way particularly if you come out of big
25:53
law there's an expectation about levels of resources i
25:58
think I think particularly in my world of being a business lawyer and a lawyer
26:04
for small and medium-sized businesses often in the big firm mentality there is a disconnect
26:12
between frankly the cost of the services and the business objective at hand and
26:17
and I remember a time working for a big firm where it's you know we dropped you
26:23
we spent 30 $40,000 doing the initial filing and some lawsuit and then I
26:28
realized well this whole lawsuit's fighting over $60,000 but we just spent half of it like there has to be a different way
26:36
to approach that that doesn't you know nobody watching a business model does that make sense are there times that it
26:42
makes sense yes if I'm the big company and I want to create a reputation in the community you can't push me around and
26:47
you know I want to be the Goliath and okay I get that there reasons why in your business model it may make sense
26:54
there you know I don't want to create a precedent Yes I understand all that but there are also times where you know it's
27:01
a $20,000 dispute well the first thing I need to do is like how do we get out of this dispute for a few thousand dollars
27:08
maybe we can't but I need to keep the business model in mind and that's that's
27:13
something that that I think is easy to get lost in the processes and procedures
27:20
of of of corporate law and especially in litigation and litigation's a bear in
27:25
this way because it's really tough to keep litigation costs contained um you
27:32
know the answer is how do I avoid litigation um so I'm rattling on here Chelsea but like
27:39
that's another thing I try to do with like contracts is like now the contract needs to be about how do we how do we
27:45
not get into trouble while we're doing business with each other because the last thing we want to do is be dropping money on litigation it would be much
27:52
easier if we just all did what we're supposed to do and what is the document
27:58
that tells me what we're all supposed to do that would be our contract so now the contract needs to
28:05
read like a recipe card instead of like whereas the party of the third part
28:11
fourth Robinette triple I little V says you know
28:18
yeah I can see that and and I was laughing earlier because that was one thing I had to overcome coming from the
28:25
financial space like accounting is the language of business right and it is a language it has terms and I was laughing
28:31
because I had to figure out how to speak human through my education of finance to
28:37
get through and and you know help people understand who didn't know numbers and who don't know finance and all of those
28:43
things so um so one of the things that I see that stunts back to my original
28:49
question the creativity and the resourcefulness is money um and a mistake that I see law firm owners make
28:55
instead of tapping into creativity and how they could creatively solve a problem um they kind of throw money at
29:02
the problem so I love how those all weave in and you know inevitably you
29:08
know to our audience like it's about them it's not about you like speak their language come across you know in a way
29:14
that they can really get it and give them the tools they need in a way that they'll actually want to use them and
29:21
empathy I think goes in all you know a lot of what I'm talking about is in the world of corporate transactional law but
29:28
but empathy which is really what it is when you put on the mindset of your client and of your audience empathy goes
29:34
a long way um in in all kinds of p practices and I think
29:41
You know to me the the times when I have
29:46
represented either companies like business owners dealing with a longtime employee who's become a problem
29:54
or longtime employees who have been you know being shown the door right those
30:01
from both sides that hurts like hell that's that sucks big time and and and I
30:07
appreciate as as someone who owns a business and who has hired people and had to fire people it's like when
30:15
something goes wrong with your team it hurts personally that's part of your identity as an entrepreneur
30:22
and just letting your client know I get it this sucks um it hurts it's going to
30:30
keep hurting is is really important there there's you know there these
30:36
stories get swapped around uh I won't vouch for its complete accuracy but I but I I I remember there was a story
30:43
going around in the as that um a major hospital chain wanted
30:51
to change its policy and actually start apologizing to the families of patients
30:57
who had bad outcomes like the doctors wanted to say I'm sorry it came out this
31:03
And we did what we could and sort of the the risk people at
31:09
the hospital were like "No don't do that we admitting liability you know you can't do that you can't give an inch you
31:14
can't show anything." And finally decisions made no we're going to be humans and we're going to express
31:19
empathy and the result I heard was that their number of lawsuits and liability
31:27
went down by expressing empathy by putting on the mindset of of
31:35
the audience they actually improved their legal
31:40
position which is a reminder that most people don't sue for monetary reasons
31:46
they sue because they're pissed off and if you can keep people from being pissed off mindset of the audience then then
31:54
that you know that will lead to better legal outcomes so that's that's where I try to put these are all pep talks I try
32:00
and give myself too Chelsea i'm I am a long way from perfect on this and it's an ongoing balance right that the
32:07
balance between delivering the service and the framework and the black and white and having that human component
32:15
you know cuz too much of either side is not going to serve you or your clients
32:20
so it's about striking that balance and if everything's changing all the time and we have these things popping up then
32:26
it makes sense that it needs to be revisited consistently it's It's kind of like you're a student of it for life
32:31
you're never truly a master you know at that art right we practice law yes i'm still
32:40
practicing exactly exactly okay so we've got So we got mindsets we got the We did
32:47
entrepreneur audience i'll rattle through some of them for for for the the sake of time and and your audience's
32:54
patience so the the mindset of the storyteller just a reminder stories are what grab people right your elevator
32:59
pitch what is your elevator pitch and is there a story behind it because that's what that's what captures imaginations
33:06
that's part of capturing empathy um when when trial lawyers talk about you know
33:12
the first thing I needed to realize was what's the theory of the case most of these cases are never going to get to a
33:18
jury but from the very beginning I need to be thinking what am I telling the jury what's the theory of the case
33:24
what's the that's storytelling it's the same idea what how do I reduce this whole complex piece of
33:30
litigation into a story and ideally one line
33:35
uh same thing for transactional negotiations especially in the kind of
33:40
setting I'm in where frequently I'm I am dealing with an imbalance of power I'll represent a smaller business negotiating
33:46
with a larger business that comes up a lot I need a good story I need I need to be telling the story of why you want to
33:53
work with this business what's the value you're getting for this business and why maybe this business why you Goliath it's
33:59
not in your best interest to make my business the smaller business actually
34:04
go through that and you do that with storytelling and with with selling the story of the
34:13
business and of the deal and it really is that kind of exercise uh there's the
34:19
mindset of the marketer to me this is one that that is really easily
34:25
forgotten outside of the world of of marketing and quote marketing and
34:30
communications um uh you know deep within the bowels of law firms
34:36
uh you know within corporate training and HR departments really easy to lose sight of the mindset of the marketer
34:44
which is simply to learn from the people who persuade for a living that there are
34:49
people who have invested billions of dollars and made billions and billions more by knowing exactly what it is we do
34:56
to persuade people to change their behavior to win hearts and minds so that
35:02
when I open my wallet I do a certain thing with the money that's inside of it and I do a certain thing with my
35:09
time as lawyers we also persuade for a living but we do it in a different
35:14
setting we do it over a negotiating table or we do it in a courtroom or we do it in
35:20
arbitration but again we have to persuade an audience and we have to meet them where we are so what does all tie
35:28
into each other like we all tie into each other focused on one right so what do marketers do they keep it short i
35:36
will tell the story of of corporate training compliance training which again is an industry I come out of
35:43
how many compliance training courses these days are still 45 minutes an hour
35:49
here's your two-hour mandatory California anti-h harassment training why is it two hours because the law says
35:55
we have to give you two hours of training every two years yeah every two years you could do that by giving me you
36:01
know 60 two-minute courses all right what does the marketer
36:07
do well last time I looked most TV commercials were 30 seconds or shorter
36:13
and they seem to work you know political campaigns back
36:18
when I was a child ran hour-long commercials with like speeches by the
36:23
candidate you don't see that anymore it isn't because candidates can't you know national candidates can't afford it they
36:30
have all the money they need to buy whatever marketing works they don't run hourlong commercials anymore because
36:36
they don't work the lessons are out there all we have to do is look and see what do
36:43
marketers do and then you know try to try to follow along this is how things
36:48
get read get used get understood you know why do I think I
36:54
know more than they do and and again this is part of being a closer no I appreciate that it's so smart like look
37:00
at the people who do this study this study the data like take that shortcut please yeah so then there's the mindset
37:07
of the producer what we call what what Nicole and I call the mindset of the producer and that is you know have a
37:13
process right if if I produce things for a living like I'm a movie producer I'm a TV producer right I have a process I
37:20
don't make it up the first time it's like step one step 20 step 30 um make a
37:26
process when you can make a process it should be repeatable it should be scalable that is also you know that's
37:32
that's entrepreneurship 101 right it's like is it repeatable and scalable but
37:37
that also has to So for what we do as lawyers and what we make for our legal
37:44
clients are we handing them something that is also repeatable and scalable that's really where the value is and
37:50
Chelsea I know for you and in your work you know thinking about process is
37:56
is a big one right absolutely absolutely and I I find that
38:03
um this is a great place where like if you're a lawyer and you're listening to this right now and you are telling
38:09
yourself the story that you know my practice is a unicorn I don't see any
38:16
potential for processes i can promise you if you can open up your mind to be a
38:22
student and and create a new narrative in your mind there is absolutely a process and a system for whatever it is
38:28
that you need and by the way processes and systems are the only way that you
38:34
grow scale protect profits exit profitably without them it's not
38:40
attractive to outside buyers to team and clients get an inconsistent result
38:49
let's talk after the show
38:54
still learning still working on that one but Always a student yeah yeah always always a student uh only just practicing
39:00
so yeah so mindset that's what the mindset of the producer is about and it's in a way it's also the mindset of
39:06
what we call the mindset of the collaborator right make a team even if you're solo you know from whom can I
39:14
learn who can help me out how do I enjoy the benefits of of
39:20
working with other people what's what's the team I can create and that doesn't mean I have to hire somebody although
39:28
sometimes it does and that can be great And it's very rewarding it can also just
39:33
be who who do I collaborate with you know for for companies frequently there
39:39
is the board of directors that you do some formal stuff with and then there's my board of advisors who I do more you
39:45
know who we're not taking notes and it's not part of corporate governance and it's the people who tell me I'm full of
39:50
it and that's that's part of being a collaborator too and I I think for
39:56
lawyers in particular at least in my practice this is important when it comes
40:03
to knowing and teaming with experts and concentrations that I don't do and one
40:09
of the things that that I have decided over over my many years of practicing
40:14
law uh one of the things I've decided is like okay these are areas that I have
40:20
some familiarity with i'm not going to dabble in them you know I'm not going to dabble in tax law i'm not going to
40:26
dabble in patent prosecution i mean I was I was an intellectual property
40:32
journalist for 10 years i know the patent system i know enough about the patent system to know I should not be
40:39
drafting patent claims unless the only thing I do is draft patent claims
40:44
because that is a minefield so I collaborate right if a
40:50
client needs something from me and it's something I don't personally know how to do I build a built a network of people
40:55
that I would turn to and I'm still building that network of people I can turn to and say I work with them in this
41:01
area and that creates what in networking circles i'm also a member of of BNI and
41:08
that's turned out to be uh that was a pandemic decision I made like I want to see people and it's a
41:14
pandemic what am I going to do going to sucks I'm going to join BNI and I'm like wow this is like paid off in so many
41:20
different ways not just in referrals but in also in having collaborators and and what what in networking circles whether
41:26
it's BNI or association for corporate growth or Vistage or whatever else what people call power teams right these are
41:33
the people they're not in my company but they're my they are my strategic allies we are passing business back and forth
41:39
we are collaborating all the time because we serve similar client bases from different points of view and and
41:44
that's a critical ical mindset I think for for a successful lawyer yep i agree i've always believed in be a
41:52
master of few not a jack of all trades i think there's a lot of power that
41:58
Exactly leaning on the people we know and and finding people who know what we don't or who are better than we are in
42:04
some areas i mean you've got to be able to do that as an entrepreneur i I I will
42:10
quote I will quote my my marketing guy um Josh Irons who who runs u the
42:16
marketing firm I rely on and and his saying for his firm is we we'd rather be
42:22
your shot of whiskey than everybody's cup of tea yes just you know I love that
42:29
um so two mindsets to go if we're going to if we're going to do the full the full list of eight uh there's the
42:34
mindset of the program executive and let me spend some time I guess on this Chelsea a little bit of time because this is like where did this come from
42:41
program executive what do you mean this to me this is
42:46
something Nicole and I went back and forth like what is this we're talking about and this is the way we capsulated
42:52
it this is something kind of born of our times there all these communications channels now right there's it isn't just
43:00
you know two or three ways of communicating with people there's dozens of ways there's hundreds of channels of
43:05
communicating with people there's all these technology possibilities there's all of these technology processes I
43:12
could tap into there's all this disruption and on top of that the economy has gotten to a place where
43:19
things that were for jobs at the turn of the millennium are one job now right
43:25
we've we've you know everyone's gone lean and everyone's laid off lots of people and then hired other people like
43:31
any a job description now used to be something four people did
43:37
what do you have to do in this environment and I I I was a big West
43:43
Wing fan right and I remember I remember the episode where President Bartlett is
43:48
talking to Rob Low over a chessboard and he says "You have to see the whole
43:54
board." Okay what we have to do is we have to see the whole board and we have
43:59
to keep challenging ourselves to see the whole board so you're a program
44:04
executive as in don't think of yourself as running one show don't think of yourself even as
44:10
running one network you are running just because you live in 2025 you are running
44:16
a web of networks you have a range of possibilities of
44:22
things you need to do and you have to master the whole board you have to you have to use one thing and trade it off
44:28
against something else in the world of marketing communications this is you know what message goes out on you know
44:35
blue sky and Instagram and the other message goes on YouTube and LinkedIn and what are the ways that I'm going to
44:41
actually repeat the same message and all those places and you know which thing goes
44:46
where that's part of being a program executive if I have content and I have channels how am I going to distribute
44:52
that content across channels but then think that way about your business or about your practice not just about the
44:58
marketing of that practice but just again seeing the whole board um I I I
45:04
will say right now you know and so in the pivot you're seeing what sucks for your
45:10
base and then how do I bring what I have to bear against that i think the other thing that comes
45:16
up and Chelsea this is a place I am challenging myself now like this is a current challenge I think my firm is
45:22
facing and I assume other firms are facing what do we do about artificial intelligence
45:28
right um I think if if you say oh I'm all in on AI you know that's look how
45:34
easy this makes life well if if if it's all about AI and AI can do it then your
45:40
clients don't need you They can ask Gemini or chat GPT or
45:46
whatever they want just as well as you can right it's actually not enough right
45:52
it may be faster there may be a process but what about quality what about
45:58
accuracy what about the art of persuasion and being a lawyer that's what you bring to the table and so as a
46:05
program executive you have to see the board and all the possibilities and then you have to decide i mean maybe I should
46:12
say you're an organist right i've got 150 different keys and pedals and I'm going to play this chord with these
46:18
three keys um you know maybe to me we have to become you know we have to
46:24
become the AI artist we have to become the AI whisperer right think of AI as your as a paintbrush not as the whole
46:31
painting and use it to deliver better value to our clients i don't think it's
46:36
yet apparent how to do that um the platforms I've played around with
46:43
continue to hallucinate they continue you get one result that's spectacular another result it's like oh man that is
46:49
so far off um the example I give to you
46:54
know I give to clients is I I had a client who say oh I had chat GPT drafted can't you just review it and it's like
47:00
yes I can spend three hours getting chat GBT's outcome to be legally okay or I
47:07
can spend 20 minutes doing the same thing from my own template that I've been massaging for 10 years you choose
47:14
ai is nice and sexy i got a faster way it's called experience right and oh here
47:19
look at this chat GPT document you see how it says in this paragraph like the
47:24
50th paragraph buyer shall and it has all these duties of the buyer it's like um you're the
47:31
buyer you don't want those duties you want the seller to have those duties because in this deal you're the buyer
47:38
but JTGBT doesn't know that it doesn't know the context it frankly doesn't even
47:44
really know the contextual meaning of any of the words it just knows this word sounds right after this other word and I
47:51
can predict what word sounds right next that's what large language models at their heart are doing are they getting
47:57
better of course they're getting better are we going to have to stay super nimble about what to do with this new tool yes we certainly are um we're going
48:05
to have to adapt to the fact that frankly to me standard research tools have gotten worse since AI's gotten
48:12
better because the vendors want me to buy their AI tool um at least that's how
48:17
it looks to me as a buyer um so that's part of seeing the whole board and the
48:23
mindset of what we call the mindset of the program executive and then that that's the mindset of the Chelsea also
48:30
the mindset of the buyer right you're going to have to rent rent it until you make it um what are you going to spend
48:36
your precious money on what are you going to throw money at i like to throw it at things that are force multipliers
48:41
i like to throw it at things I don't know for my practice the first thing I spent money on was
48:47
bookkeeping um and yeah Chelsea that's smart you can Yeah yeah I can I can I
48:53
can back you up on that one um what what am I doing spending all this time i'm not an accountant i don't
49:00
know this stuff other people do they are happy to do it for me and they're happy
49:06
to do it for me you know and I can instead go build and uh I'm not an
49:11
accountant but I you know I figured that one um I figured that one out um and I think
49:19
the same thing goes for buying technology right it's like I could buy I could completely sink every dollar I bill into technology i can't do that i
49:27
need to think like a careful buyer about what I'm buying and then finally that takes us back to the entrepreneur to the
49:32
mindset of the entrepreneur itself to me it's a circle you know we we but but at the end it's the mindset
49:39
of resilience of the entrepreneur it's like I you know I'm a survivor i will find a way through this i am built to
49:46
weather the storms yeah yeah cuz you know working a job you get to clock out not only on a piece of
49:52
paper or you know a time card digitally but you get to clock out mentally and as entrepreneurs we've taken the
49:57
responsibility of we don't actually get to do that we would some of us would like to think that there's a separation
50:02
between work and home um but it's so easily pierced and it gets blurry um and
50:09
so it is so important and I love your eight mindsets because to me it also
50:15
sounds of like sounds similar to the fact that as entrepreneurs we wear multiple hats in our business and
50:22
they're all very important and I think so I had this question for
50:28
you but you actually already answered it which is great because we already talked about like you know what's for the future and we're talked about AI but
50:36
another question to kind of leave our listeners ers with is wearing all the hats and being an
50:42
entrepreneur can be overwhelming hearing all of these mindsets and everything that we've talked about from you know
50:49
making a situation that sucks how can I make money out of it what does it take to pivot and all of these things that we
50:56
really have to do as entrepreneurs what would you say are just two of the most
51:02
important things to focus on for the people that are feeling overwhelmed listening to all this right now
51:12
wow i the the first thing I would say is cut yourself some slack okay be be
51:17
gracious be gracious to yourself to me part of what I get out of thinking about
51:22
the mindsets and thinking about the life of the entrepreneur is and thinking about this sucks how do I use it to make
51:29
money is th this is the name of the game it
51:35
isn't you i mean okay yeah sometimes it is you you got to be aware where you have to
51:42
where you have to improve right but life sucks in a lot of different ways you got to stick your struggle yeah right the
51:47
definition of insanity right you keep keep doing the same thing expect a different result you know yeah okay i'm
51:52
guilty uh in in so many ways but at the same
51:58
time give yourself the grace for being human give yourself the grace of realizing
52:05
what you have done and what you are accomplishing think about the value you
52:12
are actually delivering to your clients
52:17
and to me part of it is also you know you're having fun yeah uh part of part
52:25
of what I part of what and and it should be fun and it you should think of it as fun and it should be it the journey
52:32
should be rewarding to you because if you're if you've taken an entrepreneur's
52:37
choice you you have your own firm and you're running your own firm you need to there's not a you know
52:43
okay there may be a destination at the end but that that's just not that's just not how the practice works right I
52:49
finished this client there's another client and another client and another client when I was a journalist Right we
52:54
finished this edition now there's another one and then there's another one and it will be that way for as long as I
53:00
have this job right um you you need to enjoy the journey you need to embrace
53:07
the journey and what's going on and you know I there's something I say to new
53:14
potentially new entrepreneurs when they're thinking about starting a business which is you know I've I've learned that when you run your own
53:19
business life is great 13 days out of 14 the 14th day is
53:26
payday and suddenly on payday instead of it being like it doesn't matter how bad things are suddenly there's money in my
53:33
bank account now it's it doesn't matter how much fun I'm having suddenly I have to put money in other people's bank
53:38
account um or in my own and that's a challenge but it also means
53:45
you need to enjoy those other 13 days and if
53:51
you I guess here's what I would say to lawyers who maybe are not in their own firm right if you're there and all you
53:57
can think about is man I wouldn't do it that way boy I think that's a mistake boy this really came back to bite us do
54:02
we have to keep doing it this way i would do things in a different way like keep take those notes to yourself file
54:09
that stuff away make the hypothetical thought in your head what would I do in this situation and then wait three
54:15
months or six months and see if your answer was right or if the managing partner's answer if they made a different decision was the right
54:21
decision a learn from that but be it if you keep thinking that way and you keep
54:27
feeling like I think I know the better way you may be wired to have the
54:32
entrepreneurial mindset and you should go off that way and I know other people who are like found themselves in positions where they're running their
54:38
own company not just lawyers they're running their own company they're going through these struggles they're
54:44
challenging these mindsets and they realize you know what I liked it when I was part of a bigger team i liked it
54:51
when I had my own world that I worried about but I didn't worry about the whole
54:56
world i liked having resources anytime I needed them and I you know was talking
55:03
to somebody the other day and they're in a big organization they were like "The problem is not money if I decide we need to spend money on something I could
55:09
spend money." Right if you like that world that's fine that's who you are
55:15
that's your mindset you you may not be cut out for what we're doing um but if you do have that
55:23
mindset and you think that way then then embrace it your strengths are your
55:28
weaknesses strap on these mindsets be conscious of what you see when you strap
55:33
on those mindsets and and think about delivering value to your clients and
55:41
uh you know good times and bad that that carries me through