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Climbing mountains to build a world based on dignity with Winter Van Alstine

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One day after her 40th birthday, on July 27, 2023, Winter Van Alstine conquered the Everesting Challenge on Aspen Mountain in Colorado. The feat required hiking the mountain, bottom to top, nine times without sleep. It took Winter 21 hours and 30 minutes, and through her efforts, she was able to raise a total of $10,000 for Acumen. 

What inspired you to take on this challenge of Everesting?

It started with my 40th birthday approaching. I was trying to think of something I could do to give back to the world. I wanted to do something positive and challenge myself. Everesting came to mind as I had heard of it before, and I had heard of similar events that people had done around the country. I started looking into it and it seemed like the hardest thing I could possibly attempt.

I have done other endurance events: ski mountaineering races, cycling races, running races, and to me this seemed like the next hardest thing to try. If I’m going to make a difference, I should try and do something really hard and hold myself accountable, all the way. I wanted to see if I could set my fundraising goal high and take on something extremely challenging, to inspire others and help achieve real impact. 

What were some of the toughest moments you faced?

I started in the dark and I finished in the dark, which made it really challenging. I had to do nine laps up Aspen Mountain, with a vertical gain of 3,267 feet per lap. The most I had ever done in training was four laps in a day. So I knew I would have to dig deep inside myself at some point. 

Planning for the change in temperatures throughout the day was really challenging as it was cold in the early morning hours and really hot in the afternoon – in July. Not knowing how my body was going to respond after so many hours was daunting. I didn’t know if I could actually do it. 

There were similar events around the country that I had looked into. According to those regulations and similar rules, people were given 36 hours to complete a similar challenge and had access to medical assistance, coaches, training plans, and there was a 24-hour-a-day gondola running for easy access down. You could sleep and take breaks. I had looked up the Everesting Hall of Fame and there were some really specific rules about completing an official Everesting challenge, either as a cycling challenge or a running challenge. In a running effort, to complete it, you’re not allowed to sleep. You have to get all your “vert” in on the same consecutive climbing route. If I was going to do it, I wanted to play by the official Everesting rules – with full integrity – no stopping and no sleeping. 

How did you get through those tough moments?

I had a pacer for many of my laps and several different ultra endurance runners and athlete friends took turns to assist me. They were really strong athletes, and their support provided me with constant reinforcement, encouragement, and care. They kept telling me: “You can do this!”

In the back of my mind, I was aware that I hadn’t quite reached my fundraising goal as of early that morning. Trying to do this for other people, not just myself, really gave me motivation. I was told that I had hit my fundraising goal about 12 hours into the effort which gave me a huge surge of inspiration and compelled me to just keep going.  

I didn’t expect the amount of people who showed up for me. Throughout the 21-hour period, there ended up being a lot of community effort and support. I would get to the bottom of a lap and there would be a dozen people cheering for me. Before my last lap up, there were over 30 people at the bottom of the mountain, in the dark, cheering for me. I kept thinking about all of the people that I could potentially be helping and reminded myself that any fatigue or physical pain was temporary. The fundraising aspect gave me the drive to keep going and to finish.

What was one big lesson you learned?

There will always be challenges in any endurance event, but you can never anticipate what they’ll be. You might hope for everything to go smoothly, but it almost never does. Having flexibility is really important. But I learned a lot about myself, knowing that I’m capable of really hard things. We are capable of hard things.

During my training, I came across this quote: “If your goal can be achieved by yourself without needing help or support, then your goal isn’t ambitious enough.” It really resonated with me because I’ve always found it hard to ask for support or assistance. Reaching out for donations, fundraising, cheers, and support was challenging for me. It taught me a valuable lesson, and I credit much of my success to the support behind me. You can do so much more than you ever think possible when you include, ask, and invite others. When you think you have nothing left, then you dig deep inside yourself, you learn there is always more. 

Why did you choose Acumen to support?

I was searching for a cause to support, a way to give back to the world, months before. I contemplated a couple of different causes that I was aware of. Around that time, I had been listening to a lot of podcasts including one of my favorites hosted by Rich Roll. In one episode, he interviewed Jacqueline, and her story, Acumen’s story, and the cause deeply resonated with me. 

I decided to research Acumen more. It became evident to me that this was the organization I needed to support. Without a doubt. I also learned that Jacqueline had spoken at the Aspen Ideas Festival, which is particularly relevant to me as I’m from Aspen, Colorado. That’s when it really fell into place.

I reached out to Acumen and presented this crazy idea I had in mind to see what resources could be available. I wanted to see if they could assist me in setting up my fundraiser, and from there, things started to take shape. Acumen made it so easy.

Winter Van Alstine and Jacqueline Novogratz at a recent Acumen event.

You climbed mountains to help others “move mountains.” What are some of the “mountains” you’re most passionate about moving?

It’s apparent to me the significant challenge we face with wealth distribution in this world and local disparities in our country. I never knew how I could give back or what I could do to really make an actual difference and to be impactful in someone’s life. Acumen helped inspire that in me. Building a world based on dignity, working together, witnessing vast and unfair wealth gaps around the world has left me wanting to do something but just not knowing how. The mountains that I want to move mirror Acumen’s values: building a world based on dignity, investing philanthropic capital, promoting education, protecting our resources and our environment, making a better world. 

What was it about Acumen that activated you?

I found Acumen to be very inclusive. I felt that I could seek support and receive a prompt response. While there are many amazing organizations out there, I didn’t want to be in a position where I had to defend the organization’s decisions or justify where or how the funds were allocated. To ensure transparency and accountability, I invested a significant amount of time on Acumen’s website researching and reading about how the money was managed.

I made a deliberate choice not to handle the funds directly or set up a GoFundMe campaign. It was vital to me that the organization’s integrity could stand on its own. I wanted people to be able to verify things independently, which allowed me to feel confident about where the money was going and in asking people to support me. 

What advice would you give to other people who are interested in participating in a similar challenge?

Don’t hesitate to seek help and ask for support. A huge challenge I faced was reaching out to others, getting the word out, and spreading the message. Don’t be afraid to take that step. Don’t be afraid to put yourself out there and hold yourself accountable. Aim high with your goals, even higher than you believe you can achieve. Setting ambitious goals will keep you inspired and motivated. The more you talk about your cause and share your challenge, the more people become interested.

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