Candice Carpenter Olson has built businesses, steered billion-dollar IPOs, trained thousands of women to enter the workforce in Saudi Arabia, and earned degrees from Stanford, Harvard, and Union Theological Seminary. She has held executive positions at American Express and Time Warner and has been an advisor at AOL. She is an Emmy Award winner and a recipient of the MIT Award for Entrepreneurship. She’s been called an indispensable voice on closing the global job skills gap, and, for a moment in 1999, she was one of the most visible women in American business.
But here in Aspen, she’s just Candice. The neighbor you see around town, the woman who once ran a beloved downtown coffee shop, an avid athlete and rock climber, and now the keen mind behind a new one-day summit, Frontiers of Knowledge, bringing world-class thinkers to the Wheeler.
In this conversation, she reflects on lessons learned from the high-stakes world of startups and IPOs, running a business in downtown Aspen, and why her next chapter is all about reshaping how we see the world.
Q: You were one of the first women in the United States to take a company public. What was that experience like?
Candice:
It’s like planning an outdoor wedding—everything can go wrong at the last minute. At the time, I wasn’t aware I was setting any milestones—when you are building something ground-breaking, you’re too busy running full tilt to think about that.
Q: Is it necessary to adopt such a narrow focus in situations like this?
Candice:
Absolutely. My mind goes to the first guy to free climb El Capitan, only to find the last pitch the hardest. Everything about building the business and the insane growth expectations (in that internet boom) had already been exhausting for the whole team. And then you get to the final leg of the IPO—it’s like walking a tightrope wire high above ground. And then you get to the final leg of filing the IPO, and everything starts crawling out of the woodwork.
The head of the Securities and Exchange Commission called us a few days before our public filing. Ironically, they wanted to learn from us because our accounting was so conservative for an internet company. Regardless of the reason or outcome of the meeting, if the media had caught wind, it would have killed the IPO. It took nerves of steel and a decent amount of luck in the end. Anybody who says you don’t need luck is out of their mind.
Q: How did you deal with the stress?
Candice:
Well, I’ve been sober for 35 years, which helped keep me clear-headed. But what really kept me steady was my daughter.
Q: Michaela?
Candice:
Yes, Michaela. She was born in 1993, so she was six when all this was happening, and we were best friends. We would snuggle every night and relish being in our own little world.
She said the sweetest thing recently, she said, “Mom, now that I’m an adult with my own stresses, I don’t know how you did that, going to war every day and coming home and being so soft with me.”
Q: I think that alone is something you can be exceptionally proud of. How did you do that?
Candice:
The truth is, I had a ritual: I’d sit outside my apartment door for twenty minutes before going in, just to let the day go. Without that transition time, I couldn’t have switched from CEO to mom so quickly. And I watched a lot of TV, I mean a lot.
Q: To switch off your brain?
Candice:
I mean, I couldn’t turn my brain off just by sitting there. I needed something to soothe me. Netflix still soothes me incredibly.
Q: I want to stay on the topic of stress management. Can you go deeper into how you coped with everything during this time?
Candice:
When you go through something where there is a lot of noise in the media, you
have to completely block it out, like an NFL player going into the Super Bowl.
You have to operate in the absolute present. There is no do-over.
What also got me through were investors and a team I felt utterly responsible for because of their years of contribution and faith—this is not a solo sport.
As a rock climber, I’m trained in the idea that there are times you can’t make a misstep, and that’s when our full capabilities as human beings come to the surface.
Q: What was the biggest lesson you took away from that time?
Candice:
I was sensitive and I took things personally, but getting trashed by the Wall Street Journal, which at some point comes with the territory of fame, made me realize some goals are worth more than the luxury of being a softy.
I toughened up even though it was not my default personality. But it came at a cost. When you put on armor, it’s hard to take it off at the end of the day. But I had to, and developing that mental fortitude was the biggest challenge—and lesson—of all.
Q: What advice would you give to a young entrepreneur?
Candice:
You need to be willing to rearrange your life when big opportunities present themselves. You need to realize it’s going to be amazing, life-changing even, but often not fun—there will be periods that are so hard you just want to let it all go.
Q: So after the IPO, you started the Fullbridge Program with your husband, Peter?
Candice:
Well, at that point, I felt I was liberated from a life of cage fighting and was in Divinity School recovering. But my husband, who was at Harvard Business School, worried his students were not getting enough real-world value, so he convinced me to start a company with him, preparing liberal arts graduates for real-world careers. We created a condensed program combining top business leaders and professors, early Zoom technology, and coaches.
While our most prestigious win was that the top law firm in the country had us train their incoming associates every year, the most meaningful work was preparing 20,000 Saudi women—in Arabic—to enter the workforce. We won a huge follow-up contract, but then King Abdullah died suddenly, and his nephew had completely different priorities. We were ready to be done. We sold the company and moved to Aspen the same day.
Q: And that’s when you made the move to Aspen?
Yes, my daughter, Michaela, had moved to Aspen around that time. We thought it would be a temporary pause, a rare chance to take real time off in a place that felt like a deep breath. Six months turned into 10 years!
Q: What have those 10 years in Aspen looked like for you?
Candice:
I’d spent years operating on a big stage, and when I got here, I wanted to go very local. I consulted for the mayor for a year and a half, got to know the engineers in City Hall. Most people who move here never see that side of Aspen—I was really lucky.
I went through yoga teacher training, completed three years of spiritual psychology, and returned to school for a PhD in Philosophy, cosmology, and consciousness. I also became an athlete again, spending more time in the mountains than in meeting rooms. It’s been a completely different way of being in the world, and I’ve loved it.
Q: How did the challenges of running a Main Street business compare to your previous endeavours?
Candice:
Michaela and I owned, and she ran, Local Coffee and Here House for seven years. Retail here can be as stressful as doing an IPO.
Between seasonality, bad snow years, unexpected events like COVID, and city regulations that can be costly and poorly timed, it’s a constant balancing act. The cherry on top is that you have billionaires complaining about the price of coffee going from $4 to $5.
Michaela jokingly called it retail jail; she initially worked for almost nothing. But it’s also deeply social; you meet everyone, create a sense of community, and most customers are genuinely grateful.
But it’s harder and harder for small independents to survive. Know that if a local business raises its prices, it’s to survive, not to buy a Ferrari.
I wish more people understood that. The amount of love, goodwill, and grit that goes into keeping a small Aspen business alive is enormous.
Q: With Here House and Local Coffee closed, what’s next on the agenda?
Candice:
After years of operating at full tilt, these last ten years in Aspen have given me the space to slow down, reflect, and feed the more thoughtful side of myself.
As I enter a new phase, I wouldn’t so much call myself a policy activist as a worldview activist, and that is what I am trying to achieve through the Frontiers of Knowledge summit. It’s designed to bring together leading thinkers in our understanding of the world. No lectures atop an ivory tower. We keep it grounded with relatable discussions that spark curiosity, challenge assumptions, and ultimately inspire real-world action.
I’m not interested in policy change that gets overturned a few years down the line. We aim to transform the way we perceive and interact with the world, facilitating change from the ground up.
Q: Can you tease a bit of the roster for us?
Candice:
Gladly! Iain McGilchrist is coming—his new book has been called the most important book in the West since Darwin’s Origin of Man. Brian Swimme is a cosmologist who invites us to see our place in the unfolding universe; Bruce Damer is an astrobiologist exploring the origins of life. David Abram helps us see the more-than-human world anew. And more…
Q: And it’s at the Wheeler?
Candice:
Yes, 13th of September!
Q: Sounds great! One last one to take us home. Do you think you’ll ever leave Aspen?
I don’t think so. I could see myself spending a few months a year in a university town just to hang out with fellow geeks, but Aspen has been part of my life for fifty years. I’ve seen it go through countless different seasons, but it always finds a way to rebalance.
People who come here only for status usually get bored and move on. For me, Aspen is home, and I don’t see that changing.
Candice Carpenter Olson has spent her life reaching summits—corporate, personal, intellectual—and now, she’s creating one for the rest of us. Frontiers of Knowledge isn’t just another Aspen event; it’s the product of a woman who has built billion-dollar companies, held the line in IPO war rooms, and still believes that the deepest kind of change begins with how we think, connect, and imagine.
On September 13th at the Wheeler, she invites Aspen to join her at a different kind of summit. One not of altitude, but of inquiry. Because for Candice, it’s not just about climbing higher. It’s about seeing more clearly from wherever you stand.
Bryan Welker lives and breathes business and marketing in the Roaring Fork Valley and beyond. He is President, Co-founder, and CRO of WDR Aspen, a boutique marketing agency that develops tailored marketing solutions. Who should we interview next? Reach out and let us know bryan@wdraspen.com
This article was originally published by The Aspen Times.
