#383 Deborah Perry Piscione: From Power Plays to Pay-It-Forward—How Work Got Rewritten — Part One

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Hi, everyone.

Welcome to our show, Chief Change Officer.

I'm Viz Chen, your ambitious human host.

Our show is a modernist humility for change progressives in organizational and human transformation from around the world.

A few days ago, we published a three-port series with George Trim, the co-author of the book, Employment is is Dead.

But we are not done yet.

We are doubling down on this conversation.

Today, I've invited his co-author, Deborah Perry Pestioni,

an entrepreneur, Silicon Valley insider, and best-selling author of the book, Secrets of Silicon Valley.

Before diving into the world of startups, Deborah spent 18 years in Washington, D.C., working in the White House on Capitol Hill and as a political commentator for MSNBC, Fox News, and CNN.

But everything changed when she moved to Silicon Valley.

Instead of politics, power, and the vision, she discovered a culture built on collaboration, innovation, and risk.

taking.

That shift led her to build six companies, write multiple best-selling books, and now to found the Work 3 Institute, helping businesses navigate the future of work.

We're featuring Deborah in a two-part series.

In part one, we explore her incredible journey from shaping policy in Washington, D.C.,

to securing venture capital through a chance encounter at a Starbucks.

She shares how risk-taking, adaptability, and breaking the old rules shaped her success.

Then in part two,

we tackle the future of employment.

Why degrees aren't what they used to be.

How AI and Web3 are reshaping jobs.

and what companies must do before it's too late.

And of course, we'll answer the big question.

Is employment really dead?

Get ready for bold eye-opening conversation.

Let's jump in.

Good morning, Deborah.

Welcome to our show.

You are the first interview I conduct in the new year.

Thank you so much for your time.

Thank you so much, Vince.

It's such a pleasure to be here.

Thank you for allowing me to share my story because I think my story, my background is so critical how I now see the world.

And so prior to coming to Silicon Valley, I had spent 18 years in Washington, D.C.

I worked on Capitol Hill.

I worked in the White House.

I was appointed into one of the presidential administrations.

And then I ended up following into media as an on-air commentator with MSNBC, Fox News, and CNN.

And then DC ended up writing my first book.

But when I realized when we moved to the West Coast and Silicon Valley, I really had spent 18 years doing two things.

Two things I learned how to do really well.

I learned how to divide people into an us versus them,

because in Washington, D.C., it is all about politics.

You're a Democrat, a Republican, for the bill, against the bill.

There really is two camps in that regard.

And I also learned how to put fear in people because when you put fear in people, you can increase viewership at your respective

television network that you're at.

And you can also increase political contributions if you're putting fear into people.

So I just thought everybody worked this way.

This is the way things were.

I never realized that there were other cultures out there in the way that things got done.

So in 2006, my husband and I moved out here and I quickly realized

how the shift in the questions and how people introduce themselves.

I was so used to Washington, DC, two questions, where did you go to school?

Who do you work for?

And then suddenly I came into this culture where it was, how can I help you?

And that very question came up at a Starbucks three weeks after being here.

And I was standing in line at a Starbucks.

Someone noticed I was new in our little small town right near Stanford University and asked me, how can I help you?

And because at that very meeting, a couple weeks later, I was sitting down with one of the premier venture capitalists, Claytor Perkins, and that venture capitalist said, I like you.

Figure out something to do.

I'm going to fund you.

And because of that funding, and my first company that I ended up building out with my co-founder, that company sold 18 months later.

And I realized what a unique culture Silicon Valley truly is.

It's collaborative.

You often work with your competitors.

It's for the greater good.

It's not about money or or power or greed at the forefront.

It's more about how can I contribute in a way to changing the world.

And so from that experience, I ended up writing the book Secrets of Silicon Valley that got picked up in 39 countries around the world.

It made the New York Times bestseller list.

And I realized that having this perspective of not being from Silicon Valley really gave me an interesting view on how things could be and how things should be.

So I was really the first person to attempt to write what this culture was about.

And if you wanted to try to adopt a similar alchemy, these were the characteristics, the mindset, and the culture that you need to bring to the forefront in order to make it successful.

So really in Silicon Valley, I very much did a build a company, write a book.

go on a speaking tour, watch and repeat.

So I built out six companies.

This is my sixth book coming out, and continue to be on a global speaking tour, not only teaching the Silicon Valley ecosystem, risk-taking to enable innovation, but also an innovation process that is a bottoms-up process where any person in any corner of the company can bring forth good ideas.

And of course, this next book, Employment is Dead: How do you make this transformation from the traditional into the era of AI and Web3 technologies?

You've had such an incredible journey from Washington, D.C.

politics to Silicon Valley startups, from entrepreneurship to authoring multiple books, building six companies, and now shaping the future of work.

Looking back, do you see a common thread?

that ties all these transitions together.

Yeah, Vince, I wish I I had a really interesting story, but it is quite organic.

It was really based on needs that popped up, or my kids had an influence on one of the companies for sure.

But it was as silly as I recognized that women in venture capital, private equity, and entrepreneurs needed to be brought together.

So one was Ally to the Valley, more about the community.

And then when I was on a speaking tour and you're under the hot light, I just developed almost like an undershirt that protected my clothes.

And that ended up getting licensed.

And it really just came out of specific needs that I saw in the marketplace for myself originally or something around my children's development.

It sounds like you are someone.

who's highly absorbent, sensitive to your environment, and deeply aware of the trends around you.

You mentioned your background in journalism, talking to all kinds of people, reading situations, and understanding patterns.

That skill set seems to carry over into how you approach opportunities.

You spot gaps, see what's missing, and then take action.

whether that's building something from scratch, teaming up with others, or investing in solutions that address those needs.

So in a way, your entrepreneurial mindset isn't about business.

It's about identifying what needs to be solved and turning that into action, a product, or even a business model.

Would you say that's a fair summary?

You're incredibly insightful for bringing that up.

I do have to feel it.

It's not like I definitely see needs out there that are not necessarily applicable to me or the people I know.

So it is something I've just, I do put mind, body, and soul into all of it.

So there is, there's, there's got to be a feel.

And really at the end of the day, I think what very much distinguishes the people who come to Silicon Valley, and I'll say this over and over.

Yes, there are times it's been described as the gold rush, but at the end of the day, the people who really succeed are the people trying to make the planet better.

It's not about the money first or the greed.

When it's quite understated, if for those of your guests who have been here to Silicon Valley or haven't, it's not necessarily what you would think of in terms of being such a wealthy place based on so much entrepreneurial success because people are incredibly understated and really do care for the most part about the good of the planet.

And obviously, there's certainly competition in trying to be number one without a doubt.

We're competitive beings.

But at the end of the day, it's really about continuing to advance technology.

in a way that makes it meaningful for people.

You've built and

been involved in multiple ventures, which means you've experienced both the highs and the lows, the wins, the setbacks, and everything in between.

Looking back, is there a particular failure or challenge that stands out?

Something that, despite all your success, really tested you?

Maybe at the time it was frustrating or even painful, but in hindsight, it became a lesson you carry with you.

Something that shaped how you move forward.

You've founded, you're stronger, you're energized.

But is there a moment that, while tough, still holds deep meaning for you?

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That actually dates back to a time when I first moved to Washington, D.C.

And the first thing I bought myself when I had enough money to do so was a bike.

And I would ride this bike every day on Sundays to Roosevelt Island because I didn't have a lot of friends there at the time.

I didn't know anybody in Washington, D.C.

until I ended up working on Capitol Hill.

And I would ride to Roosevelt Island every Sunday and go to the center of the island where the statue is.

And my favorite saying of Roosevelt is, it's better to try and fail than never to have tried to succeed at all.

And it's something I've taken to heart.

I throw things out there all the time that don't work.

But I know that sometimes you've got to throw you know, a dozen things to the ceiling and one of them may stick and 11 of them may may fail and that's just part of the journey is really about risk-taking because risk-taking no matter what happens whether it's successful or it fails at the end of the day you're going to learn something incredibly valuable i have learned and time and time again there was a great article in harvard business review many years ago about the founder's dilemma.

And again, it goes back to the root of greed.

It's not about the greed.

It's about moving things to the next level.

And so maybe you don't like that number that's being offered to you as an exit or in a strategic partnership, but there is going to be so much greater benefit by exiting or doing that strategic partnership than continuing to sail on your own.

And so for me, it's all about risk-taking, knowing that 80% of the time you may fail, but that 20% of the time is what keeps life really interesting.

You've been engaged in a lot of interesting endeavors.

The current project is Work Free Institute,

which you co-founded with George,

leading to this book, Employment is Dead.

What was the motivation behind starting Institute?

What was the driving force that led you to create it?

I guess this goes back to the why.

What inspired you to take this path

i

never

understood the command and control model known as tailorism which dates back to 1918

i never understood sitting in my office in washington dc

finishing my job by 2 p.m but yet I had to sit there until 6 p.m.

because it was just FaceTime.

So the value was based on time rather than productivity and output.

Now we're in the era of AI and other Web3 technologies that is going to make work not only that much more efficient, but individuals who can really capitalize off the benefits of having these new technologies in the workplace.

So the Work3 Institute that Josh and I built together is really advising companies and enterprises, how do you

traditional

organization into the era of AI and Web3 technologies, bringing your employees along in communication, in this evolution, in upskilling, all the things that are going to be required in this next generation of work.

And Josh and I both, at the end of the day, feel very passionate.

We don't understand.

If you're going to spend the most hours of day at work, why should you feel bad?

Why should you be treated poorly?

We need to encourage people to bring their best selves to the table.

And you can't do that if you don't have psychological safety.

You can't do that if you can't try new things.

So work three is really showing leaders how they move and do this massive transformation that's going to happen and bring their employees and workers along to be a part of being on the train, if you will.

While the title is Employment is Dead,

if I'm hearing you correctly, this book is really a message to employers, almost a wake-up call.

With all the new technologies happening, the traditional value chain of employment is being disrupted.

whether companies like it or not.

And if they don't adapt, they risk losing the best people, whether to solo partnership, competitors, or simply disengagement.

Is that the core message you're trying to get across?

And is this the primary audience you are speaking to?

I think we're trying to target and edify not just leaders, but workers themselves to say they've got a choice now.

They don't have to put up with the old style and the old guard anymore.

We are in this era of a hyper gig economy.

So maybe you got an education in coding, computer coding.

Maybe you don't like it that much.

Maybe you spend an hour a day doing it because Anthropic is now assisting you in coding.

And you really enjoy a lot of other things.

And so you can cobble

various ways of earning a living together in ways that you could never foresee decades ago.

I remember when I needed extra money because my first job on Capitol Hill was $13,000

a year.

I needed to work at night in order to be able to afford to live.

And I would have to type in these job ads as people were watching over me and making sure that I was just doing things just right.

Really feeling like enslaved in a lot of ways.

And so what we're seeing now, Vince, is that we're moving into this bifurcated work track.

Traditional employment will remain.

Some industries will never evolve fully.

They may die out.

There's other industries.

We need to be more cautious.

We can't have AI and Web3 technologies taking over.

But there are other industries where, you know, the leadership is going to realize that one person can now do the job of three or four.

So what happens to those people, the three or four people who now lose their job because of AI?

And so we're really trying to edify both sides of the house, if you will, to understand,

here's what's coming.

You need to upskill as quick as possible if you need to.

Because we've got Gen Z coming into the workplace.

This is the first time

we will have a generation coming in who knows the future and work

better than the current people in leadership.

And so it's going to be a real, I don't want to use the word that's on my mind, it's going to be a circus.

And so you really have to edify yourself what's coming down the pipe and understanding how you need to evolve or make adjustments as quick as possible.

Sure.

Now

I noticed the book includes a story about how you and George met.

Two people from different backgrounds who, according to the book, hadn't even met before.

Yet somehow, this collaboration just clicked.

From your perspective, what was the spot?

What made you think, hey, this is someone I need to work with?

As Josh may have shared with you, he ended up applying to speak at a Web3 summit that I was putting on with another Silicon Valley notable.

And we were probably getting in about a dozen applications a day.

And I wasn't even the person necessarily to do the first vetting of these speaking topics.

But I just happened to capture Josh's submission.

And I thought, there's a book.

This is a book.

So you want to talk about risk-taking.

We didn't know each other at all.

And so I just asked him, I emailed him and I said, look, your topic sounds interesting, but I have something even bigger to talk to you about.

And we had a first phone call.

And I would say within 10 minutes of that phone call, I was like, hey, do you want to write a book together?

And that's how simple it was.

And I think when,

and I don't want to make this about gender at all, but I think that men in particular are really good about jumping off the cliff, right?

And just saying, hey, I'm going to give this a shot.

Women may be in general a little bit more risk adverse, but when you open yourself up for opportunity, you never know what can come along.

And it may work and it may not.

But in this case, not only did it work, but we ended up getting many bids on this book and then ended up working with Harvard Business Review.

What does each of you bring to the table?

I imagine there are similarities that made the collaboration work, but also key differences in your backgrounds and experiences that add unique perspectives.

Can you share a bit about that?

What you each contribute and how those differences shape the work you're doing together as a partnership?

Yeah, I have always been fascinated with innovation and bringing ideas to the table because everybody's walking around with good ideas.

It's just, is there a pipeline?

Is the psychological safety there?

Is there an improvisational element to being able to bring forth good ideas?

So right after I wrote Secrets of Silicon Valley, I ended up writing a book on risk-taking to enable innovation.

and really looked at what it took to be successful, to have bottoms-up innovation processes rather than the other way around, where it's top-down and it's executives driving the future of innovation within an organization.

Because at the end of the day, what I realized is sometimes it's the people closest to the job, sometimes it's the people with the smallest paychecks in the room who may have the next

multi-hundred million dollar idea.

And so I ended up developing in concert with

Qualcomm an innovation process that enabled anybody in any corner of the company to bring forth a new idea.

And so I've always come with that

mindset leading with innovation first.

Josh comes from more of an HR perspective.

on and employee dissatisfaction.

And I think the marriage between those two perspectives make it a very comprehensive book.

I had the privilege of reading through the book before it was published.

Now, I'll be honest, I skimmed through a lot of it.

Certain chapters really stood out to me, especially the one on credentials.

Before starting my podcast, especially before COVID, I was deeply involved in the learning and education technology space.

I was speaking at conferences around the world on the future of work, including South by Southwest.

So when you covered credentials, education, and training, that chapter really caught my attention.

Now, looking at one of the quotes from that chapter, you wrote,

Getting more employers to rethink their degree requirements will take hard work.

Employees have grown up in a system where the four-year degree is the proxy, and that's a perception that it's risky to do things differently.

I completely agree, but the big question is, how do we actually change that mindset?

What's your take on making this shift happen?

I shall share that I'm living this.

I have a twin boy.

Both would have been sophomores in college by now.

One is at a traditional four-year college.

The other one got waitlisted at Harvard and was thinking about the Naval Academy as well.

And he had started a business during, he had started a street work company called Faith versus Fury during COVID because he was 15 and very bored sitting at home.

That's the web for today.

We've covered Deborah's incredible journey from DC politics to Silicon Valley startups and why the old way of working just doesn't cut it anymore.

But we're just getting started.

In part two,

we'll break down the real shift.

happening in the workforce,

why college degrees are losing their their grip, and how AI and Web3

are reshaping jobs, and what companies must do before it's to link.

Plus, we'll tackle the big question.

Is employment really dead or just evolving?

Don't miss it!

Thank you so much for joining us today.

If you you like what you heard, don't forget to subscribe to our show, leave us top-rated reviews, check out our website, and follow me on social media.

I'm Viz Shen, your ambitious human host.

Until next time, take care.

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