Parallel Entrepreneur with Mark Cleveland

Hey everybody, welcome back to The Parallel Entrepreneur. I'm Mark Cleveland,

your host, and today I am excited to introduce a guest who's truly a catalyst

for growth and innovation in the business world and a great resource for The

Parallel Entrepreneur.

Jason Putnam is a two-time award-winning executive celebrated as the Globie

Executive of the Year and a Silver Stevie Award winner in 2021,

but most recently named in 2024 as Inspiring Leader by Inspiring Workplaces.

Jason has an impressive track record and a lot to share about scaling online

and SaaS businesses while building top-performing teams, creating positive, lasting impact.

As Chief Revenue Officer of Plum, we're going to talk about what is Plum.

Jason is in the forefront of transforming talent decisions through psychometric

data, helping businesses make smarter and more inclusive hiring choices.

So I can't wait to dive into Jason's journey and hear his insights that have

fueled his success. Welcome, Jason Putnam.

Thanks, Mark. What a good intro. I appreciate it. I'm excited.

I'm definitely hitting this one with high energy. I

want to ask you um i guess my

first question is people will sometimes get an

introduction like that and then the listener is like well now what

is plump so take us through this value

proposition and why it's so important for the parallel entrepreneur people people

are what helps grow companies i think they're the most important thing that

you can have and even if you have a great idea without the people to help you

do it it's not going to work and what we do at plum is is revolutionary from

the perspective of we're able to look at the whole human,

those things that get them out of bed and motivate them every day and align

that to a job that they're going to go into.

So when they're in that job, they are happy and fulfilled.

And when they're happy and fulfilled, they are going to stay longer.

They're going to be more productive. And ultimately, the benefit back to the

company is you have somebody who's going to be there a long time,

they're going to be happy, and they're going to be exponentially more productive

than somebody who when they close their laptop, at the end of the day, they go pour two drinks.

In this situation, they get up, they're happy to go to work.

When they close their laptop and they're done, they're celebrating their day

as opposed to resenting it.

We're going to talk about celebration. We're going to talk about pace of change.

And I'm hearing already in your voice this passion. And I know you to be passionate

about fitting the right people in the right place and how that impacts an organization.

Talk to us a little bit about how entrepreneurs in the plum universe are leveraging

your tool to do exactly that at scale.

Yeah the at scale is is really the the important part and

when i say at scale it could be you're scaling a business

right which is my my passion helping other people scale their

businesses but it could be really large companies like city banks a client of

ours and whirlpool and hyundai really really large companies what they're able

to do is when you're when you're building that from the ground up they're able

to not only bring the right people into the organization again who are happy

who are doing the job but it's helping them align their culture and when you

look at it as an entrepreneur,

whether that's a founder starting something new, or whether it's a CEO of a Fortune X company,

they kind of have three main goals, in my opinion, as a founder or a CEO of a large company.

Number one, you have fiduciary responsibility. Do you have enough money to grow

the business? Do you have enough money to pay your people? Are the revenues

there, all the typical things that we would think about?

Number two is, are you providing a safe and a growing environment for your people?

So do your people feel safe when they come to work, but also are you setting

it up to where they can grow and in their career, whether it's with you or without?

And then the third is culture.

Do you have the, there's not a good or a bad culture, right?

But are you aligned with culture to make sure that all your people can help

you in that up into the right journey with an aligned culture?

And that's what they use Plum for. They use it from a selection perspective

to make sure the people who are coming in are going to be the most productive.

And they're using it both on that selection process, but also in what we would

call talent management, not just talent acquisition.

How do you make sure you're providing everything you need for the people who

are currently at your business to be the most productive?

And then from a culture alignment, is everybody aligned on that culture that's

coming from the top down?

And our mantra is that when people flourish, meaning the people in their roles,

the business will thrive.

And there's many, many reports out there outside of Plum that prove that to be true.

I love it. Now, you are an entrepreneur, you are a leader, and you have been

at multiple organizations.

And I think one of the common themes at Parallel Entrepreneur is how are you

recognizing the patterns from one experience that you're importing to the next,

this opportunity of synergies between organizations,

synergies between clients,

synergies in the marketplace that align talent. Let's speak to that.

Yeah, so my passion, and I know we'll get into passion a little bit, but I really want to help,

make people's dreams come true. And that's, you know, most founders,

that's what they started out trying to do.

So that's a common theme across all of them, right? They had this idea,

they want this thing to be true, whatever that is, a for-profit,

a non-profit, a bake sale. It doesn't really matter what it is,

right? You did it for a reason.

And as you mentioned, right, like a lot of the guests you have on here are founders. I'm not.

My passion is helping those founders scale and exit and bring their dreams to life.

And when you look at it that way, some of the patterns that I see are really,

they had this great idea.

They were most likely an inventor type founder.

And the idea is fantastic. The product is fantastic, whether it's something

tangible or software or whatever it may be.

And they're missing some of those elements to be able to get there.

And they need to surround themselves

with people who know how to take the business to the next level.

And when you're a founder, especially like a startup founder,

again, whether it's a tangible piece, like Bill, one of your guests with his

e-bikes, or it's like a piece of software, there are experts out there who can help you do that.

And just understanding when it's time to pull those levers on people,

when it's time to take a business from not just that, hey, it's this idea that I had.

Okay, now that I have this idea, is it repeatable? Are people not just buying

it as a one-off? Are they buying it multiple times?

And then once it's repeatable, then how can I take it to be scalable?

And that repeatability to scalability and ultimately sustainability,

that's really where my passion comes in.

But that pattern is almost at every company I've ever been a part of and multiple

companies that I'm a part of today.

So, Kaitlin McGregor is the founder of Visionary that created Plum,

and you are a part of the team that is executing that vision at scale.

And I'm curious, how did you meet and how are the two of you slaying dragons

in this relationship of co-executor?

I met Caitlin. It's an interesting story to me as we talk about kind of my passions

for helping other people.

And the way that manifests sometimes is just running into people.

And I've been in the HR tech space for a long time.

As you mentioned in the bio, I feel very blessed and honored for the success that I have.

But I happened to be exited one company, going to another company.

I hadn't made a decision of where I was going to land yet, but I was at an industry

event and a bit of an inner circle.

A PR firm at my previous company was also the PR firm at Plum.

And our a great PR firm called The Devon Group. Their team's amazing.

And the team there said, hey, will you please go to this industry dinner?

Because Caitlin, who's our client, doesn't really know anybody.

And we're a Canadian company.

So she was coming into the US, small company that had been around 10 years,

but wasn't really where anybody wanted it to be.

Not a lot of people knew it. So we sat down, had dinner with her,

huge table, and it was myself.

And at the time, a woman named Michelle Meehan, who ran brand marketing for

us. She's now our VP of marketing over here.

We were at PandaLogic together. And as we sat there, I looked up,

I don't know, three hours later, and it had only been the three of us talking.

And she was sharing some of those things. She was sharing her journey.

She was sharing the struggles she had had. And just the person in me of wanting

to make people's dreams come true and help them, we bantered back and forth

about, hey, this is how I would do it.

Because everything I do is really, I'm a pattern person, right?

So I'm able to kind of see the forest through the trees and use the same patterns

and the same approach I've always used to kind of go there.

So as she's coming up with these struggles that she's had for a decade,

it's like, well, here's what you should do about that. Here's what you should do about this.

And by the end of dinner, she had offered us both jobs and Michelle and I are

here today. So that's how we ran it ran.

That's how the origin story met as, as one would say. And then it was about.

Taking somebody who is a founder and saying, yes, you've done this for a long time.

And yes, there are things that worked really well and there aren't things that worked really well.

And it's now time for you to separate yourself from some aspects of the business

and give those to people who are going to be able to take it to the next business.

So as we're talking about slaying dragons, we went from a company that had been

around 10 years and was thinking, dabbling into enterprise, going from like

SMB to bin market to enterprise to fast forward three years later.

In the last two years, we've won 100 awards, over 100 awards.

We've grown the business hundreds and hundreds of percent.

We're now fully baked in enterprise.

Some of the biggest enterprise companies in the world use us.

And we're really viewed as really the darling in the industry when it comes to what we do.

So we have really big dreams. And it's not just trying to build a company to

exit, like that's my job, but we want to do things for good.

And there's a lot of people every month, frankly, 50,000 people a month who

take Plum as part of an application process or an employee or even organically

to learn more about themselves.

And although we don't make money on that side, that's the thing we celebrate

a lot because we're giving people the opportunity to learn more about themselves.

We've democratized access to this really, really helpful data,

the psychometric data that people have.

And we're helping people find jobs and we're helping people change careers and

we're helping people build upskilling and coping mechanisms to be better,

to be feel more fulfilled in their job. And when they're fulfilled in their

job and we're aligned, right, then they're going to flourish in what they do.

You know, a common theme in the parallel entrepreneur podcasts experience for

me is how founders view recruiting.

And I'm a human talent tracker. I recognize talent when I see it.

What a great story about how Caitlin met you and the change makers,

good cultural fit, and the humans are good at making these judgments.

But there's also there's bias, there's undiscovered bias in the process of bringing

people at scale into your organization.

You know, clearly it was a good decision for her to recruit you and you to recruit

other people on the team.

So the attitude towards recruiting is key.

Talk about what happens in this unconscious bias and how do you free your entrepreneur

clients, your growth companies?

How do you free them from that restraint?

It's an interesting world to me because there is intentional bias.

But there's a lot of unintentional biases, as you talked about.

And the older you get, the more set in your ways that you get,

the more that comes to light that, hey, all salespeople have to be this way.

All accountants have to be this way.

Or they went to the same school that I went to, the same university that I went

to. So they're probably this.

Or they were the captain of the football team. Or they were the head cheerleader.

Whatever it may be, there's that bias in there.

What you find is when you start looking at patterns around people,

you're leaving out so many diamonds in the rough. So not to be a commercial

about Plum, but I just want to tell a story that talks about exactly the question you asked, Mark.

Scotiabank, which is a really, really big Canadian bank. And for years,

they went about it like this.

And very unintended consequences and I would say unintended bias.

So they say, hey, for our early career, recent grad program,

here's how we go about bringing people in and recruiting them into the organization.

They say they had to go to these five universities. By the way,

they're the same five universities that probably the CEO, CFO all went to.

They have to have a business degree or a finance degree, right?

So you have kind of two buckets that if you weren't one of those, you're out.

And what they ended up finding out was they would make 10 offers or 100 offers,

but about 20% would say yes.

And the other 80% would go out to, they'd go work for Deloitte or another bank.

So they couldn't bring in enough talent that matched those really specific gating

functions and the ways you would screen people to commit.

So they took a really novel approach and they said, we're going to eliminate

resumes for recent grads and early entry, and they're going to only apply with Plum.

So we're looking only at what we call durable skills. Think of it like soft

skills, your ability to innovate, work well with others, determination,

all those things that go into psychometric data.

And when somebody applies, they're matched to, let's say, 16 different jobs

at the bank. And that's what they use to bring them in.

So even though one of those people may be a 98 out of 100 for Plum,

that person may have not gone to one of those five schools.

They probably didn't. They may not have a business or finance degree.

Well, if you fast forward to now, they're now hiring for that program from 32

different universities.

40% of their hires have STEM and art degrees, and 60% of their hires are underrepresented minorities.

And these are now, they're bringing in the top, top, top talent.

We ask the internal team every year, of the people you brought in,

would you rehire them again? And it's nearly 90% they would rehire again.

So those are people they never would have even seen before. And we've taken

out that unconscious bias to say, there are people, especially now when you

think of the world of AI, everyone can apply to a million jobs and every resume

is going to look the same.

You really got to get it down to what makes that person special?

How does that align with what we need at the organization?

If it doesn't align personality-wise, psychometric-wise, they're better off

not coming to work for you, for you and for them. So let's bring in the people

who are going to be able to really flourish here at the right time so we can thrive as a business.

Yeah, what a terrific insight. They stopped. They re-evaluated their process.

They threw out the resume, and I think that is a game-changer re-evaluation

of how you recruit and determine what and what is not talent,

what is and what is not a match.

Are, and I would like to believe this question is a laydown,

but are there enough companies who are willing to throw out the resume and take

advantage of the match of talent to the requirements of talent for success?

The answer is no, which you're probably not surprised today,

because number one, HR tends to be, it's a long answer, Mark,

HR tends to be, has become more of a risk aversion kind of department.

Like, let's make sure we don't make a mistake to protect the company.

So by nature, you don't have a ton of innovators or early on adopters.

There are some, I don't mean to be that to sound derogatory,

but by nature, they're at their bottom of the P&L type people, right?

They're not people who are like me or you, who's like, I'm willing to take a

risk, even though I may fail at that risk. By nature, they have to do that.

So as a department, that makes it hard. And the bigger the company,

it also makes it hard because the change management is hard.

Where I see change coming is based on, we talked about the pace of change, the pace paradox.

They're going to be forced to do it. And that's really where change happens

at companies. You're going to have to be forced. And here's what I mean by that.

It used to be that the companies had all the power.

So if you were a big company or a small company, you were in charge and you

controlled how much people made unless it was minimum wage. And you said,

here's who I'm going to hire.

And as a company, I didn't just have the power because I was writing the paychecks.

I had the power because I had a technological advantage. I could put an ad in the newspaper.

I eventually have an applicant tracking system. I can have all these ways to

be able to attract you and then say yes or no.

Well, as soon as generative AI happened, that has now even the playing field.

And it's a long answer, but I think it's really important for even early on

founders or small companies to understand this.

So now the human, me, if I'm an applicant or I'm an employee who's going to

look for a job somewhere else, I have the exact same technological advantage

as a company or a corporation does.

So now it used to be, again, the company struggled with looking at a thousand

resumes and determining the one person they're going to hire through whatever their process is.

But as a human, I could only apply to so many jobs because it was arduous.

Now there's tools out there that I can match my resume to any job description

and be a perfect fit with AI and apply to a thousand jobs a day.

So because I have this technological advantage, the juxtaposition between the

two is an even playing field, like I said.

Then when you layer on what's going to happen with generative AI and the pace

paradox that we're talking about, the things that can be automated are going to be automated.

So if you think about a programmer today, those things that went into being

a programmer, do you know this particular programming language?

Do you know this? All that's going to go out the window because now the skills

needed are going to be much more of these durable skills. Now a programmer's

most important talent is can you communicate well when you're writing these prompts?

So there's going to come a point when the only thing that's going to be left

to differentiate people is who they are as humans.

And those hard skills, right, do you know Excel? How well do you know Excel?

Those are all going to be automated. So it's going to be forced that you're

going to have to look at it this way.

And what you did on a resume, so if you think about it like LinkedIn,

LinkedIn says what you've done.

You're going to have to figure out a way to match people on what they can do, not what they've done.

My, and I love this great leveling that AI represents. You've talked about pace of change paradox.

Let's dive into that just a minute, because when you say it's going to happen,

and we all, in my own work, studying AI, implementing AI systems,

managing pace of change specifically at an organization's state of readiness for change.

I'm not sure people really understand just legitimately how fast this is happening.

So let's address that topic.

Yeah, there's a futurist. His name's Ira Wolf. I recommend everybody go read some of his work.

He has this concept called the pace paradox.

And I'll summarize it. So if you don't want to go read this,

you don't have to. But of all the things we're talking about today,

at least for my opinion, I think it's the most important. It's also the scariest.

But it goes into, hey, why do I feel the way I feel? And we all kind of feel

weird right now. Like, oh, that seems different. Let me tell you why it is.

So the Pace Paradox says this. From 2000 to 2004, so a five-year period of time,

the amount of change that happened in that year, those five years,

has already happened this year.

So you have five years worth of change crunched down into one year.

20 years from now, that same amount of change that happened in five years is

going to happen in a month.

So now think about how fast things are going to change.

So keep in mind, the generative AI we have today, as game-changing as it is,

is the most expensive it'll ever be and the worst quality it'll ever be.

It's only going to get cheaper and better and faster.

So as it gets cheaper, better, and faster, the speed of change is going to even

get faster than probably what he predicted.

So what does that mean? If I'm used to running a business, I'll say typically,

you have a CEO at the top, he or she says, here's my soldiers,

all the other C-level executives. Here's what we're going to do this year.

And then those C-level executives take it to their VPs who then take it to the

directors, right? Big corporation.

By the time the message gets to the manager, the pace of change has already happened four times.

And the same thing's going to happen with hiring and retaining people.

So as an entrepreneur with three employees or yourself or a huge corporation,

you're going to have to understand that everything's going to be changing so

quickly that you're going to have to reimagine how business is done.

Yeah, I've got that experience in my own companies where in 2019,

it took me 19 people to execute a plan. Today, it takes me two.

And, you know, all those people have used those learning experiences in my organizations

and others to amplify their effectiveness.

And I hire for culture. I've always hired for fit.

Let's just say if I was to reflect on who I am, I am a connector.

And so people will reach out to me and they're saying they're looking for a

job. They're looking for an opportunity.

So there's two questions. One is everybody who's working for you right now is

able to put out a million applications.

It's not just unemployed people looking for the right fit and a better job opportunity.

It's everybody that's on your team today, number one.

Number two, you have described a change management attitude based on old paradigms

that can't change fast enough.

So that inbound inquiry that I've received from friends, from people that used

to work with me and are looking for opportunities and staying in touch, I'll point them to Plum.

I'll say, go take, go to Plum and take the Plum ingesting experience.

And they'll come back to me and say, I didn't know that about myself. Holy cow.

So I want you to address this.

Everybody's available at the pace of change. We can barely recognize or sustain.

And what are people learning about themselves from this tool that you're offering

for free? Great question. Thank you.

What you described from an experience perspective, people come in with preconceived

notions because if you're an applicant, let's say, to an organization,

the way things used to work was you uploaded where you found your job,

wherever it is, you uploaded your resume.

And if they asked you to do something else, it was very much they were in control,

right? It was this black box, whether you were taking a disk assessment or other

assessments who are out there.

And you then, at some point in the future, if you got a response,

it was like, you're not a fit, but you didn't know why, and now you're mad.

And let's say you're a company like Citibank or Whirlpool.

They have tens of thousands of people applying, and they're hiring one or five.

All those other people who got rejected are either current customers or potential

future customers, right? So their candidate experience is awful.

So what we did was we really wanted to say, hey, let's make it about the human

first. Let's build a product for the human.

So even though they may be an applicant or they're coming organically or they're

an employee at a company, let's give all the value on the front end to the human,

even if they don't get the job.

And if you think of those 50,000 people a month who take it,

the majority of them as applicants don't get the job that they applied for.

But what they leave with is what we call Plum Flourish, which is this full career management platform.

So they can figure out not just other jobs. We actually don't serve them up

jobs. We serve them a kind of career pathing or, hey, here's why a particular

job may not be a fit for you.

Right. This company is from you talk about culture a little bit, Mark.

This company is very, very innovative and very fast. So they're going to require

people who are, again, innovative.

High in communication and really high in adaptation. If you're somebody who's

low in adaptation, it doesn't mean you can't adapt.

It just means if you had to do that all the time and that pace of change was

constant and your job was changing every day, you're going to go find another

job because you're just going to be burned out.

Whereas if my job was about adaptation innovation, which it is at Plum,

I hop out of bed every day looking for the next challenge that comes in front of me.

So being able to just bring that light to people to say, there's nothing wrong

with you, this is why you feel that way.

And if you're next time you're talking to your spouse, this is why this happens.

Next time you're talking to a colleague, try talking to things about this.

And if there's certain areas that you want to get quote unquote better at,

it's not that they're going to make you more fulfilled, but we can build some coping mechanisms.

So for me, you know, I'm an executive. I have to be really good at teamwork.

Teamwork is the thing that drains me the most, right? So if I have a to-do list

or somebody says I have an idea, I'd rather spend time talking to that person

about their idea or how to make their dreams come true versus going to a happy

hour, which is to me like a complete waste of time.

But as an executive, I have to build coping mechanisms that say,

cool, once a month, we're going to do this for our team.

And I'm going to do team check-ins these days and these days.

And I'm talking to my team all the time, but these are much more at the human

level and it's just draining for me. So I have to build those.

So we let people know that, hey, you can't be driven by everything.

There are going to be things you're really driven by. There's going to be things

you're really drained by.

And there's something you're kind to neutral with understand what those are

understand why you feel the way you feel and then let's figure

out how you can overcome some of them so you've just touched on one of my favorite

questions which is you know there are things that drain us there are things

that energize us how do you personally i think our listeners are interested

in in understanding your personal journey as well how do you restore energy when you feel depleted.

I don't know if the word depletion is right. Here's what I find kind of as a catalyst.

And a catalyst is somebody who's, you know, again, driven by change,

driven by innovation, typically brought in to drive that change.

And what ends up happening is you go really, really, really fast.

And you, because of these patterns being able to see patterns,

you're the one who comes in sometimes as a bull in the China shop and you know what needs to be done.

And you want to be able to pull people along with you. Sometimes they can't

go as fast as you, or they may not agree with where you're going.

And that is the thing that ends up depleting me. Sometimes it manifests as burnout.

Sometimes it manifests as resentment.

So what I have to do is kind of like bring myself back to say.

Okay, how do I refill that cup?

And inherently, I'm an introvert, but I really want to help people.

So I get motivated by working with people. It's why I have these other things

around me and I'm helping in all these ventures because I want to be able to sprinkle that around.

But I want to be able to, the thing that really fills me up every day is working

with really good people, but especially those with kind of diverse backgrounds

and diverse perspectives.

So I find that inspiring because if you're working with really,

really dynamic groups, it brings that other kind of thing that fills me up,

which is solving really big problems that seemed unsolvable before.

So even if it's outside of where I am or a company I'm working for,

I want to go help solve a problem.

The other thing that really helps me and if I need to recharge is learning something new.

And I don't mean like tangentially learning something new. I I mean,

going very, very, very deep into something new.

So I remember four or five years ago, we were talking about,

somebody was talking about quantum mechanics. I didn't know anything.

I ended up sitting through hours and hours of MIT lectures on it, right?

And not that I'm an expert on it, but I wanted to know enough to be able to

have a conversation with somebody, not be the smartest person in the room,

but be the dumbest person in the room when it comes to that and just learn more and more every day.

And if I could then pass some of that knowledge on or it becomes applicable

in something else I'm doing, it's really, really motivating.

And so that deep dive helped you learn how to ask better

questions in that environment yes so

how do you stay agile then open to experimentation when

success is elusive it's uh maybe it's my definition of success i i don't find

it elusive again the thing that motivates me is i want i want i want other people's

dreams to come true when it's all over someday i want i want people to look

back and say jason help me do this even if it was a small tiny thing right i

i say tell the people all the time.

I really care much more about what people say at my funeral than what my resume

and my bank account says.

And that's where I find success, right? If I have people who work at Plum with

me, we've been at five companies in a row together, some two companies,

some three companies. To me, that's the definition of success.

Here's what I have found though, when you put those people first and you work

with them and you solve big problems, that success ends up being the success of the business.

And I haven't failed yet. And I don't think I will because of that.

We are all of us learning from patterns.

You spoke earlier about patterns, pattern recognition.

A part of that is what AI is doing at scale and helping us sort of get better

at even those of us who aren't any good at pattern recognition.

We have a new tool to enable us to flourish.

I want to ask you a question about AI because I don't think we're done with

that conversation. It's moving fast.

It's in your product. It is learning to be.

Effective and learning to communicate. Right now it's hallucinating, as some people say.

And I think so many of us as humans, perhaps we hallucinate a little bit and

aren't really honest with ourselves about circumstances,

conditions, patterns that we see and things that suck us into a less than joyous state.

So I am curious about, can we individually, You've talked about how an organization

needs to adjust to the pace of change.

Are people able to adjust to the pace of change? And where does that line cross in giving us hope?

Very, very hopeful on AI, just so you know.

I mean, worst case scenario, it takes over the world and kills us all.

But I don't think that's what's going to happen. So let's embrace it.

As we've gone through all these things in history, we've all kind of been there.

I remember, you know, I'm old. I remember one of my first jobs was at a newspaper,

and it was right when the internet came out.

And they're like, you're young, help us figure out the internet,

right? And how many people actually read a newspaper now, right?

It didn't take people's jobs.

It made people's jobs better and easier and more productive.

But there's this conflation point to your question mark where I need AI in my

personal life, which everyone's using it already. They don't realize it,

but they have this weird feeling about their work life.

So people have Alexis in their home. They They talk to Siri on their phone,

right? They've been using AI for a really long time.

It's getting smarter and it's getting better, but they see it's like kind of

okay in their personal life, but they're terrified of it at work.

And the reason, again, opinion, the reason they're terrified of it at work is

they think it's going to take away their job, but it's just going to make them more productive.

The people who are going to be left behind are the people who don't adopt it.

And what I find is if people will actually start adopting it more and more at

home, it makes it way easier at work.

So I don't think there's anything to be scared of, but it needs to be pushed.

You're going to have some individuals who just own it and they're going to be

superstars, even if they weren't superstars before, because they're going to

be exponentially more productive to my point with AI.

But companies also need to push it. I'll give you, we talked about Caitlin, who's our founder.

You know, we're not a huge company, but as generative AI came out,

we shut the business down for a day, entire business, and everyone did nothing but learn about it.

And once we left there, we knew, hey, it was okay.

We learned the do's and don'ts. So we learned what hallucinations were.

We did all these different exercises and we split up departments.

You had a salesperson and a marketing person and a developer on one team.

And we had all these little mini teams. So we shut the company down.

And when we left there, we have a bunch of people who on that adoption curve

are really forward thinking when it comes to change.

And we have some who just wanna keep using their piece of paper.

And those are the people we monitored, those people who kinda just wanna do it the old way.

And those were the people who adopted it first because they knew it was okay.

They knew they could do it in a safe environment where nobody was going to feel

judged and they knew it wasn't going to take their jobs away.

I love it. And I think at the heart of humanity, we are explorers.

Definitely a consistent thread throughout the parallel entrepreneur and entrepreneurship.

In my own experience, we're exploring.

I can't help but notice, and for the listeners that aren't watching us on YouTube,

there is a terrific collection of Star Wars theme paraphernalia in your library behind you, Jason.

And I think that this idea that we could explore, we could be faster and better

and not waste time, but experience more with these tools at hand.

We're seeing it in our entertainment. We're seeing it in our imagination.

We're seeing it in the fiction we read, which is rapidly becoming the truth

and our lived experience.

Tell me why you have the Star Wars collection, What wisdom did you pick out

of Star Wars that made you such a fan? Because I need to hear that story.

Yeah, I mean, age-wise, right? It was the original Star Wars were big for me

as a kid. So that was where I got in there.

But the thing I like a lot, and this goes into, it's very applicable to this podcast, I think, is...

Star Wars really nailed the three-part epic to me.

So it could have been about anything, but what I see in life and what I see

in really successful trilogies and what I see in businesses is people just think

it's one long movie and it's not epics.

And what does Star Wars do? It's really cool in the beginning and the good guys,

quote unquote, won in Empire, right?

The bad guys won. And then the third part epic, the good guys win again.

And it's just this testament. It was a really good, big part of my life to understand

that whether you look at it to seasons or whether you look at it at epics,

if you're walking through hell, just keep walking.

And that's the wisdom I got there. But also the exploratory nature that you

brought up, the world is going to change and the world's going to become an

even smaller, smaller place,

because the speed by which we can even explore outside of the earth is going to be so much faster.

I mean, it took us forever just to launch into space.

And then we had this decades long journey where we really didn't do really much.

And then Elon Musk came and look what he did. And 20 years from now.

What's going to be going on?

It's going to be insane. And again, I love it.

And I don't think the technology that's in Star Wars will be around in my lifetime,

but I certainly think elements of it will be around in my kid's lifetime.

Well, you talked earlier about participating in exits.

You are building a company for an exit because it's a plan. It's an outcome.

It doesn't have to happen. It can happen.

You're planning for it. You're scaling for it. Talk about some of the lessons

that you've learned participating in driving exit stories in technology businesses.

What would you do more of or a little bit less of as you continue to refine

that skill and that experience and bring your team with you through it?

Yeah, it's an interesting journey, right? And a couple of lessons I would tell

people kind of out in the streets.

Most of the stories you hear about exits are the really good ones or the really

bad ones. And those are very few, if far in between, right?

My friend worked at Google and he or she made $10 billion or whatever the story

is. We put money in this company and it failed.

But most of the stuff that happens is in the middle.

When you think about it through an entrepreneurial lens, again,

I'm going to build this product and I'm going to take it to market.

And I think all these things are going to be true.

But the journey is never what you thought it's going to be.

Sometimes it's way worse. Sometimes it's way better. Sometimes it takes a lot longer.

But understand that you're still on a journey. And that goes back to kind of,

you know, the epics that we talked about.

And the biggest lesson, and this is where, again, I get my passion from,

is understanding when it's time to bring the right people in to do the thing.

So if you build a new widget and somebody buys it once, cool,

that doesn't mean a billion people are going to buy it. So now 12 people buy it.

Cool, that doesn't mean a billion people are going to buy it.

So if you're not an, let's say you're an inventor and you're not an expert on

go-to-market, what's the right point to bring a go-to-market person and team

in? What's the right time to bring a CFO in?

Oh, you're going to be selling to enterprise companies. When's the right time

to bring a chief compliance and security officer in?

So lesson one, know when to bring the people in. Lesson two,

know when to get rid of people.

And then another lesson for me is also know that not everyone's your friend.

And just because somebody tells you something doesn't mean it's always true.

And as an entrepreneur, what you say is so-and-so said this and it's great,

or they're going to help me here, or they're going to do that.

A lot of people just want to be surrounded kind of in that orbit of doing it,

but understand you built this for a mission and it's time, you know, it's time to go.

And the final lesson is just kind of be okay with good.

I know it's really hard for entrepreneurs, but there's a great quote that great is the enemy of good.

Sometimes you don't have to be perfect. And yeah, if you're building a new drug

that goes out in the market, sure, you have to be perfect, right?

If you're doing something that people are going to be driving,

sure, there's a level of perfection, but that's few and far between.

And I've seen so many entrepreneurs, even currently, who want things to be so

perfect that they don't make progress. And I'm a big fan of,

you know, progress without perfection.

Just keep going. Just keep going. It's never going to end the way you thought

it was going to end. But if you do it the right way, you're going to have an

end and you're going to be happy with the outcome.

You know, this experience of getting into podcasting, preparing really to write

a book, things that I have resisted for a long time, self-talk.

I'm uncovering my own self-talk as I'm experiencing this journey with you and

other parallel entrepreneurs. And I'm out on the edge of what feels comfortable.

I'm moving myself intentionally outside my comfort zone.

And then I still find my perfectionist tendencies are going to be the death

of me, as my wife would say.

How would you do an assessment? Your company is helping people self-assess.

Your company is helping companies assess what their real needs are,

not what they have been doing, but finding, identifying, uncovering their real needs.

Talk about assessment. Talk about the decision to innovate in the historic discipline

of self-deception or self-talk that is your self-limiter.

These, I think, are true on the

corporate side and in the personal side of living the lived experience.

Yeah, keep in mind a corporation is just a sum of a bunch of people.

A corporation is a thing. It's not a person.

So if the leader of that corporation is a perfectionist, guess what's going

to happen to the business, right?

That's just the nature of how things are, right? Now, as you get bigger and

bigger and you have a board and you have C-Levelin sex, then you have a little more variety in there.

And I don't think being a perfectionist is necessarily a bad thing because it

takes a perfectionist to get a certain thing to a certain place.

But then there is times where perfection is not always there.

Like self-talk, I'm very, very guilty of doing that, right?

Oh, I could have done it this way or I can't do it that way.

If you're using it correctly, it can be very motivating.

But there are things just that, so I'll give you a great example.

We measure something called decision making. It's got a whole bunch of competencies under it.

And you can be very, very driven, my guess is you are, Mark,

by decision making, meaning you're good at it. Not that somebody's bad at it,

but like, that's your thing, right?

But just because you're driven by decision making or your score high in decision

making, you could be patterned two different ways.

For example, I'm very high in decision making.

That doesn't mean I always make great decisions. That means a high percentage

of the time I make really good decisions, but I make decisions really quickly.

So in an innovative environment, right, progress without perfection,

I'm going to make some mistakes, but time is not going to be my enemy.

I'm going to make them fast. You can also be really high in decision where when

you make a decision, it's the perfect decision, but it took you two years to

make the decision, right?

So, hey, I need to go get, yeah, I need to go get a new car,

right? I know people who spend six months researching a car, right?

Down to the most minuscule detail. When they buy that car, they're like,

this is the best decision I've ever made. Great.

I don't buy a car that way. I'm like, I kind of know what I want. That sounds good.

Let's do it. So we're both high in decision-making, but I'm also okay if,

oh, I thought this car had this, but it didn't. I'm okay with that.

So I'm not judging myself on perfection. Where I really want to get it perfect

is aligning people to work, especially people who are on my team, right?

Because I want to make sure that number one, they can be the same person at

work that they are at home. They can feel trusted.

I'm really big on transparency, really big on loyalty,

right i want to get that decision right but everything else as long as it's

a decision you can redo just make it quickly right like hiring somebody's really

hard like take your time to do that firing somebody right that's really hard

there's decisions out there that you can't be undone take your time on those

but if there's something that can be undone just make it fast and move on.

We've talked about the explorer in each of us. We've talked about space travel.

I love this conversation. We've talked about Elon Musk and SpaceX.

And again, perhaps the apex parallel entrepreneur.

And one of the things that we just touched on was this idea of,

it's kind of been summarized in popular business books by fail fast.

But one of the things that is obvious and true, if you get out underneath it,

is that Elon Musk didn't invent space travel.

He didn't invent the rocket.

He didn't invent the idea of a reusable space vehicle.

He did some things in the area of practicing

intentional, professional decision-making and adjusting quickly.

The story goes, he began with his team to launch.

Let's just launch. And what did we learn from the launch? Okay,

what did we learn from the second launch? And a lot of rockets blew up on the launch pad.

But eventually, every single thing was disassembled and analyzed and the lessons

learned, implemented in the fastest fail-forward space development project in history.

What is that teaching us? That's an entrepreneurial, that's a discipline that

is adventurous, it's risky, and we live in a world where so many people are afraid to fail.

How do we draw from that lesson in our, maybe applied to our daily lives and

maybe applied to our business life when it comes to risk-taking and learning quickly?

Yeah, what he did was he made it okay and was very, from a leadership perspective, encouraged failure.

And I know that sounds like, why would you encourage failure?

Because when you fail really fast, you progress really fast.

And versus sitting back and engineering a rocket for a decade and then launching

it, what if it would have failed then?

Then you wasted a decade, right? So in every company he has and everyone who

works for him, whether you like his culture or not, some people love it or they

wouldn't be working for him. his whole thing is celebrate failure,

not intentional failure.

But if it fails, that means we may have learned one thing from it or two things from it.

And instead of taking five years to learn those one or two things in a laboratory

or in a classroom or an office building, let's just do it when we're out there.

And to me, that is like the ultimate entrepreneurial spirit.

Just go and let's see what happens.

So there's a couple of questions that occur to me, Jason, with so much going

on, failing fast, failing forward, I like to say it.

But how do people, how do you live in the moment?

It's hard. It's actually, it's very, very hard for me, right?

So I am somebody who wants to move forward, right, in that explorer type way.

I look at my historic wins and failures to learn from them.

And I then take that little nugget of time and say, okay, in the moment right

now, what's tomorrow going to bring?

And what did I learn from yesterday? And yesterday could be a decade ago.

And no matter when I try to sit down in the moment, I find myself pulled in those two directions.

So what I really have to do is say, okay, I'm going to focus on something that

is not a thing I'm working on right now.

So that may be spending time with my family. That may be I'm really disciplined

when I work out every day at five in the morning, right?

And I use that time to kind of just turn my brain off to where I'm not being

pulled in all these other directions.

So I've built these coping mechanisms over time, like a really,

really rigid schedule to say, I'm giving myself permission to have these times

in my day where I don't have to worry about my day.

I know that sounds weird, but like, these are the times where I could listen

to a fiction book or read a fiction book and not be worried about that.

These are the times that I could be talking to my friends about nonsense.

These are times I could watch stupid cat videos, whatever it may be,

like giving yourself permission, which is really hard as an entrepreneur and

somebody who scales, but giving yourself permission each day to have that time

to not be worried about yesterday or tomorrow.

I love it. And I think giving yourself permission is important on so many levels,

particularly in the experimentation and exploring and recalibrating and evaluating progress.

Maybe there's times where we as humans really should be doing nothing and practicing a meditation.

How are you practicing mindfulness when you're in it?

Is it just turning off or what? Part of it's turning off, right?

And then there's the, you know, part of that morning routine for me is like,

I spend part of it in prayer.

You may spend part of it in meditation, whatever your thing is like,

being able to turn your brain off and then mindfulness towards other people as well.

So I want to, you know, again, I talk about helping people a lot.

I truly want to help them in a non-self-serving, in a non, you know, self-serving way to me.

So just being able to sit there and listen actually helps me turn my brain off

because it's not about solving my problems. It's about solving other people's problems.

I probably spend four to five hours a week talking to people,

just helping them solve their problems.

And it may be people I've known. It may be a board I'm on. It may be somebody

who's, you know, their washing machine broke and they don't know how to fix it.

Just being mindful of other people really actually helps me not worry about

the things that are in my brain every day because there's a lot of them.

Excellent. So now this rapid fire section I love so much.

Jason, tell me, what's the last book you read? Last book? I'm reading one now.

So we'll start with that one because it's very applicable to the conversation we were having about AI.

It's called Scythe. So like a scythe, like a sickle. It's fantastic.

It's actually an audio book. I like reading real books, but this one's only available in audio.

And it's fast forward hundreds of years from now and what has happened in the

world of AI. And it's fascinating.

The last business book I read was, and I recommend everybody get it.

It's called The Talent Fix. It's by Tim Sackett.

Okay. The talent fix. Thank you for that. And the next book you're going to

read, what's on your nightstand?

Yeah, I've had this book for a while and I have not opened it,

but I believe it's going to be the next one. It's called Spartan Up.

It's by Joe DeSina, who's the gentleman who founded the Spartan races.

And I love to do those. It's been a while pre-COVID before I've done them,

but just how he built that business.

And just like Elon Musk, there was a bunch of people doing adventure races and

how he revolutionized that from a go-to-market perspective to really be the industry leader there.

Yeah, that's a terrific book. I personally have some experience as a co-founder of Swiftwick.

We manufacture the world's best compression socks for athletes and aimed at

that group of people out there trying to challenge themselves to take it to

the next level who would look at that sock as a tool to achieve their competitive objectives,

not just a sock you could have really low expectations for. I'm a big fan of them.

So tell me, what's your perspective on charity? How do you approach giving?

Love the question. So to me, there's two forms of it.

There's obviously financial giving, and then there's giving of your time or your knowledge.

And I really try hard to do both. Up until not that long ago, I sat on two boards.

So I have my youngest daughter, I have two daughters, 14 and 10.

My youngest daughter has Down syndrome. So I was a vice president of the Down

Syndrome Association here in Texas.

And I also sat on the autism board. So for me, that was like,

not we gave them money too, but it was just giving my time and giving my expertise there.

And then we sit down and really think about where we can, where our money will

go the furthest, if that makes sense, and have the biggest impact kind of outside of ourselves.

So there's a lot of places you can donate from a nonprofit perspective,

but there's actually only a few where you look at and it's like,

oh, more than 80% actually goes to the cause.

So I'm not going to name any of those, but that's where we really sit down and

are very purposeful in where we give them.

On the theme of giving, what's the best gift you've ever received?

It's not the best gift I've ever received, because I'm sure there's things that

are bigger and more expensive, but you can't see it on my shelf.

I have this bell on my shelf, and this bell was given to me by the woman I mentioned

earlier, Michelle Meehan, who we were together at the previous company.

She's our VP of marketing now, and it showed at my house, and it's very heavy.

It's not cheap, and it's engraved, and the engraving just has FFS.

Michelle is right again, so every time she's right in a meeting,

I have to pick it up and ring them, which I ring it a lot every day.

So it's a very thoughtful, yet funny, yet practical.

So what's the best gift you've ever given? Best gift ever.

I'll tell you the most impactful to me and hopefully the most impactful to the

other person. I have a very good friend of mine who at the time was waiting for a heart.

He was very sick and he was waiting for some other things as well.

And at the time he was also getting married.

And this was also during COVID. So they had to get married and they wanted to go on a honeymoon.

And we're very blessed to have a place in Florida that hadn't been rented out

for a while. So we made sure they did a really, really extensive cleaning there

because he couldn't, you know, he couldn't have any germs, not just from COVID,

but with everything he was waiting for.

And we provided that as a safe haven for them so they could have a honeymoon.

I love it. That was, that's brilliant.

What are the three words that define your life? In no particular order.

I would say innovation because I'm really driven by it.

Determination based on, you know, not mostly from how I grew up.

And love, like it's important to love other people, all people.

So if you could talk to your younger self, and I think we, at least for myself,

I'm my own most ruthless critic, and I've had to set that down and accept myself

and meet myself where I am, which I think is a strength. I try to meet other people where they are.

But if you could talk to your younger self, what's the first thing that you would say?

Yeah, I'll give you just a slightly long answer. Like I grew up saying a blue

collar family is probably being very generous. So, you know,

it wasn't this unlike Bill, who was one of your guests, you know,

his dad invented the CD-ROM.

I didn't grow up in that type of family from like an innovation.

It was very, very, I'll call black collar family.

So I had to work for everything I got and still do that day.

But what I found early on in life, I was pattern recognition.

I was doing pattern recognitions of other people. So if I saw somebody who was

successful, I kind of tried to emulate those people.

And it was later in life where I was just like, hey, two things were a catalyst for me.

There is a book called Move Fast, Break Shit and Burnout. It's about being a catalyst.

And when I read it, it was like looking in a mirror. It was like,

stop trying to pattern other people.

And there's nothing wrong with you. Like, this is who you are. Embrace it.

So the advice I give to my younger self is like, be yourself and don't worry

about what other people think.

Like, there's a lot of value in what you bring to the table.

And if people don't see that, that's okay. Move on and go somewhere else or talk to other people.

Yeah. Terrific advice. I wish I'd have had you talking to my younger self a long time ago. Same.

What question, Jason, did you expect me to ask that I have not asked?

Well, that's a great question.

Favorite quote. How about that? What's your favorite quote?

So my favorite quote, and it goes to what we were talking about today,

and it's from Mother Teresa.

If you can't feed 100 people, then feed just one.

So if you think about that, if I can't help, it doesn't just have to be feed, right?

Everyone looks at it to say, I want to end world hunger. I want to have world

peace. I wish there was no poverty. Whatever the big thing you're trying to

do globally, it seems so overwhelming.

But if I can't feed 100 people or I can't solve world hunger, I can feed one person.

And if everyone who could feed one person fed one person, there would be no more hunger.

And that's the same approach I want to take with humans in my life,

with business. If I can just solve that problem that's in front of me and everyone

can have that same approach, the world will be a significantly better.

I love it. I want to ask you this question because I think you are thoughtful.

And maybe we ought to be asking better questions.

What is the question that we should be asking all of us? First of all, I love that question.

To me, COVID brought a lot of things to light and it wasn't COVID,

it was that everyone was locked in their houses and they realized that their

life wasn't exactly what they thought it would be.

So the question I always like to ask people is like, are you okay?

And I know that seems so simple, but just there's a lot of people who aren't

okay and they're just, nobody's ever asked them if they are.

And if they say no, what can I do to make it better?

Like, that's what I would ask everybody in the world. Because everyone has a thing.

Everyone has something they're wrestling with that you may end up being that

person who can help them solve it. You may not be, but you may know the person.

And even if you don't know a person, at least they feel like somebody's seen

them or heard them. Well, you've been seen and heard today, Jason.

Thank you for joining me on the Parallel Entrepreneur. Ladies and gentlemen,

you're listening to a 2024 Inspiring Leader winner from Inspiring Workplaces.

I continue to be inspired by the work that Jason and his team are doing at Plum.

And I just want to really just express my gratitude for your contribution to our conversation.

Thank you so much for having me, Mark. I appreciate it. Appreciate you.

Love it. G'day.