Chief Change Officer
#175 Deborah Perry Piscione: The End of Traditional Work Begins — Part One
Wed, 12 Feb 2025
What happens when a political insider, a Silicon Valley entrepreneur, and a bestselling author walk into a podcast? You get Deborah Perry Piscione. She’s gone from shaping policy in Washington, D.C., to writing Employment is Dead, and she’s here to unpack why work as we know it is crumbling. In Part 1 of this two-part series, Deborah takes us on a wild career ride—working in the White House, pivoting to Silicon Valley, and learning that fear and division drive politics, but collaboration fuels innovation. She shares how a single conversation at a Starbucks led to her first venture funding (yes, really), why failing fast is a non-negotiable skill, and how risk-taking has shaped her entrepreneurial journey. Key Highlights of Our Interview: From Capitol Hill to Silicon Valley – “In D.C., I learned how to divide people. In Silicon Valley, I learned how to bring them together.” Deborah reflects on her 18 years in Washington and how moving west flipped her worldview on work, collaboration, and success. The Starbucks Moment – “I was in line at Starbucks when a stranger asked, ‘How can I help you?’ Three weeks later, I was sitting with a top venture capitalist who said, ‘I like you. Figure out something to do. I’ll fund you.’” Deborah’s introduction to Silicon Valley’s pay-it-forward culture changed everything. Entrepreneurial Instincts – “Most of my companies weren’t grand plans—I just saw a problem and built a solution.”From launching a networking platform for women in venture capital to creating a sweat-proof undershirt on a speaking tour, Deborah proves that the best businesses start with simple observations. Work is Changing—Are You? – “We’re moving into a bifurcated workforce—traditional employment will still exist, but the smartest workers are creating their own playbook.” Why the old career paths are fading, and how the next generation is redefining success. _________________________ Connect with us: Host: Vince Chan | Guest: Deborah Perry Piscione --Chief Change Officer-- Change Ambitiously. Outgrow Yourself. Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs, Transformation Gurus & Bold Hearts. 6 Million+ All-Time Downloads. Reaching 80+ Countries Daily. Global Top 3% Podcast. Top 10 US Business. Top 1 US Careers. >>>100,000+ subscribers are outgrowing. Act Today.<<< --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.12 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>140,000+ are outgrowing. Act Today.<<<
Chapter 1: Who is Deborah Perry Piscione and what is her journey?
We are doubling down on this conversation. Today, I've invited his co-author, Deborah Perry-Piccioni. an entrepreneur, Silicon Valley insider, and best-selling author of the book Secrets of Silicon Valley. Before diving into the world of startups, Debra 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 division, 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 co-found the Work3 Institute, helping businesses navigate the future of work. We're featuring Debra 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 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.
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Chapter 2: How did a Starbucks encounter lead to venture capital funding?
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?
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.
Chapter 3: What distinguishes Silicon Valley's culture from Washington, D.C.?
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 competition. money 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, wash 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 quarter 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 web 3 technologies
You've had such an incredible journey from Washington DC 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 recognized that women in venture capital private equity and entrepreneurs needed to be brought together so one was Alley to the Valley more about the community.
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Chapter 4: What are the key traits of successful entrepreneurs in Silicon Valley?
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
Chapter 5: How does risk-taking shape entrepreneurial success?
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 all 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.
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.
Chapter 6: What lessons can be learned from failure in entrepreneurship?
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?
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 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 in 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 asset 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 Work3 Institute, which you co-founded with George. Leading to this book, Employment is Dead. What was the motivation behind starting the 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 Taylorism, which dates back to 1918. I never understood sitting in my office in Washington, D.C., 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...
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