Chief Change Officer
#383 Deborah Perry Piscione: From Power Plays to Pay-It-Forward—How Work Got Rewritten — Part One
Thu, 22 May 2025
What happens when a political insider, a Silicon Valley entrepreneur, and a bestselling author walk into a podcast? You get Deborah Perry Piscione.In Part One of this two-part series, Deborah shares her wild career ride—from shaping policy in Washington to pioneering bottoms-up innovation in tech. She breaks down why fear is a tool in politics, but collaboration fuels real change—and how a chance encounter in a coffee shop led to her first startup and a new lens on what work could be.From co-founding six ventures to co-authoring Employment is Dead, Deborah’s story is a masterclass in trusting your instincts, failing fast, and knowing when to break the rules. Part Two will dive deeper into AI, upskilling, and why Gen Z might be the smartest workforce we’ve ever had.Key Highlights of Our Interview:From Capitol Hill to Palo Alto“In D.C., I learned how to divide people. In Silicon Valley, I learned how to bring them together.”The Starbucks That Changed Everything“A stranger asked, ‘How can I help you?’ Three weeks later, I had venture capital.”Six Companies, Six Books, No Master Plan“I didn’t have a big strategy—just instincts, observation, and the nerve to try.”Innovation Isn’t Top-Down Anymore“The best ideas often come from the people with the smallest paychecks.”Risk Is the Real Skill“You can throw ten ideas at the wall. One might stick. The rest will teach you.”Founders Dilemma: Know When to Let Go“Sometimes it’s not about the perfect number—it’s about moving the mission forward.”Why She Launched Work3 Institute“People spend most of their waking hours at work. So why do so many feel terrible doing it?”Old Model, New World“I never understood why finishing work early meant I had to sit until 6 p.m. Taylorism still haunts us.”Empowering Workers, Not Just Employers“We’re not just talking to companies—we’re telling workers: you have choices now.”Gen Z Knows More Than the Bosses“For the first time, a generation entering the workforce understands the future of work better than the people in charge.”_________________________Connect with us:Host: Vince Chan | Guest: Deborah Perry Piscione --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.18 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>170,000+ are outgrowing. Act Today.<<<
Chapter 1: What is Deborah Perry Piscione's background?
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 to spend 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 on 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.
Chapter 2: How did a Starbucks meeting change Deborah's career?
Chapter 3: What lessons did Deborah learn from her time in Washington, D.C.?
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 on 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, D.C., 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?
Chapter 4: What is the importance of collaboration in Silicon Valley?
And because of that very meeting, a couple of 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 power or greed at the forefront. It's more about how can I contribute in a way to changing the world?
Chapter 5: How does risk-taking contribute to success?
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, wash and repeat. So I built out six companies.
Chapter 6: What is the 'Founder's Dilemma'?
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?
Chapter 7: Why is the traditional work model outdated?
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 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 recognize that women in venture capital, private equity and entrepreneurs needed to be brought together. So one was me. Alley to the Valley more about the community.
Chapter 8: What does the future hold for Gen Z in the workforce?
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're someone who's highly observant, 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 gotta 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 rebounded, you're stronger, you're energized. But is there a moment that, while tough, still holds deep meaning for you?
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