Peter Sims, Writer and entrepreneur


Peter Sims, Writer and entrepreneur

Name: Peter Sims

Twitter: @petersims

City: San Francisco       

Passion: Empowering people

Peter is one of the most humble people you would meet. When I met over lunch, and after reading his accomplished and stellar journey, I was expecting to sit down and ask him burning questions. Instead, Peter showed up with a gift, a smile and open ears. He was truly present, an attitude that is rare in our ADD culture. Peter happens to be an award winning writer, the man behind one of Stanford Business School's best classes, and a former venture capitalist.  He was also the coauthor with Bill George of the best-seller True North: Discover Your Authentic Leadership, and cofounder of Fuse Corps, a social venture that places entrepreneurial leaders on year-long grassroots projects with mayors and governors to tackle some of America’s most pressing problems. My favorite part of Peter's body of work is his best-selling book Little Bets which inspired our work at The Passion Co. Peter shared with us a candid and unpolished story of how he came to do what he loves and enjoy every single minute of it.

On Passion

How and when did you find your passion?

It’s a long story, but after feeling dissatisfied with my job in venture capital, I started a search in my late 20s for more meaningful work. I discovered my passion to empower people, and help them unlock their fullest potential, as an accidental author, and then later as a social entrepreneur and entrepreneur.

I followed my curiosity and did my best to listen to my heart. There’s a quote that I love from William James:

Seek out that particular mental attribute which makes you feel most deeply and vitally alive, along with which comes the inner voice which says, 'This is the real me,' and when you have found that attitude, follow it.

 When I’ve done the work that I love, it has felt this way.

On Transition

Tell us more about the transition from your traditional job to your Passion.

Again, it’s a very long story, with many dark valleys – times when I felt completely lost, and many others saw me as lost – but, ultimately, I moved from venture capital to being an accidental author by going to business school. At Stanford, I followed my curiosity for leadership to start a class on authentic, values-based leadership.

Through the process of developing the class, which I loved, I got to know Bill George, the former CEO of Medtronic, who is now a Professor at Harvard Business School, and was starting a similar class at HBS. We had a great back-and-forth, and mutual learning, so Bill asked if I would help him with his next book. It was the best learning experience of my life, and our work was meant to empower our readers.


On Mastery

Where did you start with your Passion? 

I really just followed my curiosity, and found projects and like-minded groups of people. Role models and mentors and friends played crucial roles in support – no one ever invents a path on their own. One little bet after another, after years of hard work and building one brick after another, it got to the point where each day of work was a joy.

On Failure

Tell us about a time in your earlier transition to living your passion when you failed. How did you feel? What did you learn?

I’ve been fired three times in my life, including trying to live my passion, and I also had an engagement that didn’t work out.  What I found was that when I lacked self-awareness, I lived in ideas of who I was, rather than the “real me” as James describes. It was a very painful process of enduring painful setbacks and failures, largely because I didn’t really know who I was, and I wasn’t comfortable in my own skin.  There were many moments of feeling lost wandering through dark valleys, wondering if I would ever find another job again, and questioning myself.  The self-doubt was extremely strong, as were the many voices questioning my judgement to pursue a path “less travelled by,” especially after being offered a choice path in venture capital on the partner track. Without the support of my parents, brother, and close friends, it would not have been possible.

Today, I feel very comfortable with myself, perhaps too much so at times, for the journey is always full of learning, and I really don’t think of the term ‘failure.’  Every experience and day is a chance for learning and growth.  I try to live by the credo from Alan Kay: “The best way to predict the future is to invent it.”

 On Fear

What is fear to you? What has been your biggest fear about living your Passion?

I think that my greatest fear has been that I would not be able to get a job. I know it sounds silly, but I felt that fear very strongly for years, and it still flares up in the background from time to time.  It’s not entirely rational, but since my career is so unconventional, when I did try to get a job, it just never really worked, so my fears were somewhat justified.

I can remember one conversation that I had with my dad in particular early into pursuing my passion, when I was already an author, yet still very unsure of my path.  We were having lunch, and my dad, who took very linear career paths as a lawyer and a judge, asked me, “Peter, are you sure you know what you are doing?” He thought a career in venture capital would be exciting, yet also understood that I had my own values and interests. He just couldn’t quite understand what I was doing, since it was so different from his experience, and it wasn’t until LITTLE BETS came out that he finally understood how my mind worked.

I’ve come to realize that expressing my creativity is fundamental to my humanity, especially if it’s channelled toward just, ethical, and socially impactful ends. My dad now really respects my work and path, and he’s very proud of the hard work and struggle it required.


On Money

Was there a time when you were running out of money? Did you need to give up a lifestyle to pursue your passion? Tell us more about that and how you coped.

I’ve never been motivated by money, and there were periods (years, even) when I had a very tight budget.  I've never eaten Ramen, but the trade-off of not making the money of a venture investor was hard in one respect: I felt like the women I dated really cared about whether I made a good living. That was pretty important to them, much more so than finding a guy who was cause-driven.

Ultimately, I stopped dating a woman partly because of this. I was in love with her, and she said vice-versa, but her fears about money were significant, and she didn’t have the stomach for the risk of dating an author. In hindsight, her fears were misplaced, as I’ve lived a very comfortable life as an author, speaker, and entrepreneur, but ultimately, the people closest to you need to be 100% supportive.

I love hearing stories of hugely successful entrepreneurs like Infosys founder and former CEO Narayana Murthy, whose wife Sudha worked to help him and start the business when he had no money. That is love.

Otherwise, figure out how little you need to survive, and then every dollar above that is freedom – freedom to pursue the work you find calls you the most, and that will be the most meaningful. Money can be the ultimate trap that prevents people from pursuing their passions.  I see it all the time.

On Self-Love

How do you take care of yourself? Do you pause, work out?

I always need to do a better job of this, but the key elements are: get plenty of sleep (8 hours on average), eat as healthy as possible, and get plenty of exercise (5 times a week).

On Inspiration

Who inspires you and why?

I’m inspired by people in large and small ways. I’m inspired by my wife in many ways, my parents and brother in others, and people I don’t know who lead good and noble lives.  I’m currently reading a book about Teddy Roosevelt, and he inspires me for his willingness to stand up to corruption as an enthusiastic reformer. We need more of that type of leadership in America today. Too few people in politics have any courage, nor the conviction to take on some of the big interests that have corrupted our political institutions.   


On Support

Do you have a mentor? How did you find him/her?

I used to place a LOT of weight on mentors, and always seemed to have one big mentor through the various stages of my life, until my early 30s.  At that stage, I resolved to myself that I needed to figure things out on my own in life, and borrowed advice from John Donahoe, eBay’s CEO, who when I interviewed him, said,

Learn a little bit from a lot of people.

  I really internalized that. I’ve learned an enormous amount from my Uncle Joe, who’s a truck driver, and I’ve learned a little from dozens of taxi cab drivers.  Everyone has wisdom and insight, often very unique insight.  You just have to ask the right questions.

Advice to the Community

Follow your heart, believe in your dreams, and live your values. To do anything else would be settling, and I think it’s really important to aspire to ‘not settle’ in life – in your work, in your relationships, and in your potential to make a contribution to other people and society.

Your Inspiration

Do you have a video, playlist or anything else you would like to share with our community that helps inspire you?

I do not.  But this speech, by John W. Gardner, entitled “Personal Renewal” is the best speech I’ve ever read, and I find inspiration in it each time I read it:


Adam 'Smiley' Poswolsky, Writer


Adam 'Smiley' Poswolsky, Writer

City: San Francisco, California 

Passion: Writing, Community


The common thread amongst those who are looking to live a creative, meaningful life in San Francisco is one person. Adam is known as Smiley because he is always smiling to you, and to life in a big way. And in his own words:

"Why do I smile a lot? Well, there is so much beauty and joy in the world. I've always been someone who looks at the world, and feels good. It doesn't mean I'm always happy, but there's an inclination to look around, and I can't help but notice beauty. And when you smile a lot, it makes other people smile, too." 

With an inspiring tale of a writer, and so much he wants to give back, Smiley helped me personally honor my dreams of being a writer, when I had known him for just two hours.

We met up with Smiley at his favorite morning spot in NOPA, Matching Half Café, ( the library where he writes was closed), to talk about his first book, out in two weeks, The Quarter Life Breakthrough, on how to find your voice and purpose when you hit your mid 20s. 




I have always really enjoyed telling stories. Growing up, I loved movies, I loved reading books, and I loved the transformation that happens when you read a story. I was huge into The Hobbit as a kid, The Lord of the Rings, A Wrinkle in Time; books that kind of take you to another world. In school, I was really interested in sports, but realized since I wasn’t really good at sports- I was really short and skinny- that I should write about them instead. So I started with sports writing.

In 2008, I worked for the Obama Campaign, and then got a job working for Peace Corps headquarters in DC. I was doing a lot of writing at my job, because I was good at writing and I liked it, but it was a little more bureaucratic. It was writing in a government context; a lot of memos and talking points and policy papers, so it wasn’t very creative. I wasn’t fired up by what I was writing about. A writer needs to find their voice, and be able to write about things that they’re truly passionate about. I realized what I wanted to write about was personal transformation and people taking risks in their lives. So basically it was my own journey that inspired my writing.


First and foremost, the key is accepting that everything is a work-in-progress. I always think, I am a beginner. When you have the perspective that this is a learning opportunity, that you are a work-in-progress, it opens you up to realizing that you are always practicing and honing your craft. The process of writing my book has made me become a better writer. Every blog post I write, I get better and better, and closer to my voice.

Mastery is about learning. It’s about learning how you do your best work. I’ve learned that I am an extrovert, a people person, so I need to set intentional habits when it comes to writing. This means saying no to people, blocking a day to write with no email, no Facebook, no lunch dates. The last thing that a writer wants to do is actually write, so you have to put yourself in a place where you can actually do your work.


I had a great job on paper, but it was not the right fit for me. I was really nervous to leave a job that provided salary, benefits, and job security, because it was the recession and the job market wasn’t great. But something inside me knew I needed to listen to my heart, and make a change. It was only when I met other 20- and 30-somethings facing the same kind of situation, the same question of how do you figure out what you love and then get paid for it, that inspired me to make the leap. So my passion came out of finding a community of supportive people.

I did a program called StartingBloc, which is a social innovation fellowship. There, I met many young people who were starting their own businesses, and working for organizations that aligned with their values and the change they wanted to see in the world. That made me realize that anything is possible.

I finally found the courage to overcome my fear, quit my job, listen to my heart, and move to San Francisco, a place I’d wanted to live for 10 years. I moved with the intention of being a freelance writer, and writing about people who were following their dreams.


Failure is writing. Inevitably when you write, some people aren’t going to like what you say, and some people are going to resonate with it. So if you’re going to write, you have to accept failure. I have sent parts of the book to people and they really didn’t like it, they had a really adverse reaction based on their own experience. But that’s part of the process, you have to accept that as a reality.

Once, I wrote a piece for a social impact publication and they didn’t pay me for it. I called to ask for the money and the editor told me that the piece was the worst thing she had ever read. I’ve also written blog posts that people said had changed their lives. I’ve never met anyone who created something magical in this world that hasn’t failed.

My book, The Quarter-Life Breakthrough, can’t be a New York Times bestseller because it’s not yet in bookstores, but does that mean the book failed? No! For me, success is the growth I went through, and from people hearing my story or reading about the book. Even if the book simply helps others think more about what they are going to do with their life, I’ve already won. I have already failed and already succeeded, and my book hasn’t even launched yet!


I have a lot of fear about money. That issue of knowing how deeply I care about what I’m doing, but also knowing how much stress it causes me to worry about money, and balancing that.

I have overcome the fear of failure and what others think. Often people project their fears on you. “What happens if you get a bad review?” That is other people’s fears about themselves. Then you have to realize which fears are your own, and which are the fears of others. I learned this when I was leaving my job, that I was internalizing others’ fears about leaving a job. People can only really give advice based on their own experiences.

The big thing is accepting fear. I am scared about the money, but that makes me work harder, that makes me figure out alternative ways to make income. In a way, you can use fear as a source of energy and inspiration. So if you are scared of something, it probably means you should do it.


The biggest challenge for any artist is the balance between doing your work, and making a living. I’ve recently found that it’s this struggle, this balance, that makes you an artist, and figuring out how to navigate that. That’s how you end up doing your best work. The people that discover that balance are the ones that succeed as artists, and don’t give up.

I’ve found a variety of different projects to balance writing my book and doing the work I love. I do writing and storytelling for companies that I think are doing good work, which allows me both to write and get paid. This allowed me to work on my book, which took me 10 months and didn’t pay me a salary, but was a project I deeply believed in. I think the key is finding side projects that pay money, but also where you are not compromising who you are, what you believe in, or what you’re good at.


A lot of the times we think success and finding a job is about hustling and networking. But I think it’s about spending time with people you love and finding rituals that make you joyous. For me, that means spending time with my sister, going on Sunday walks. I’ve also started meditating and eating better.

Self-love is the essence of any good work. Surrounding yourself with people that love you makes you better.


People that inspire me are people that build communities to help others find their dreams: the Passion Company, StartingBloc, Hive, The Bold Academy. Those who are building accountability and support systems inspire me, because you just can’t do this stuff alone. My book is not just a book, it’s about building a community of young people who want to find meaningful work. I am inspired by people who are looking beyond themselves to create a network for people to do this work together.

I get inspiration from people who are younger than me; they’re not yet influenced by the late 20s pressures of “I have to get married and have a high-paying job.” Young people are still audacious and naïve, which allows them to do great things.


I have a lot of mentors. I try to surround myself with a lot creators. One of them is Ryan Goldberg, who is a freelance writer for the New York Times. He has an ability to play with words like no one else. He reminds me to keep going, no matter what. I have been mentored a lot by my friend, Evan Walden, who co-founded ReWork, which helps people find meaningful work. My sister is the one who deals with the most of my freaking out, she is my biggest source of inspiration and support.


Listen to the voice within. If something inside is telling you to do something, do it. If you have to start Sunday afternoons or Tuesday evenings, do it. But no matter what, start, and have someone hold you accountable for it. Ask yourself: what is the one thing that you know you need to do, but haven’t done yet? For me it was starting a blog while I was at my old job. It took me 20 minutes and $20 to start my blog. And just that simple beginning (writing that one blog post), helped me connect to other writers and pitch stories to publications, which eventually led me to start writing my book. There is beauty in putting yourself out there. There is beauty in beginning.