Jesse Boland


“I own the #1 1920’s fashion website in the world. I was a firefighter for 10 years, and then I broke my back. Then I decided to go to law school, hated it. But I had an English degree, I liked to write, I liked to be creative…so I was watching the Godfather one night and thought ‘I bet there’s a bunch of weirdos out there that like to get dressed up in 1920’s shit.’ I did some research and sure enough, there were, so I built a website that was getting 15,000 unique hits a day and that kept me self-employed for five years.”


“What was your inspiration to start the website?”

“I would say it was one of those God shot moment. I got the exact thing I needed and the exact time I needed it. It was luck. It was being inquisitive about the world around me. One of my talents is that I want to know why stuff is the way it is. So it was part sheer dumb luck and part sheer determination to figure out what I wanted to do with my life. I’m not super smart, but I’m often in the right place at the right time and I take advantage of the opportunities that come my way.”

“What’s the story about you breaking your back?”

“I was a wildland firefighter. We’d go to the large fires and work 16hr shifts. I was running a chainsaw and I slipped and I went ass over teakettle. I broke three of the transverse processes off on my back. My lumbar spine bulged all the discs. I worked the rest of the day but by the end of the day, my back was all messed up. At the end of the day I asked my buddy to pop my back, so he did the whole hug thing and picked me up. When he put me back down my legs didn’t work anymore. That was a little scary.”

“What was your emotional response to that?”

“I didn’t pick up on the gravity of it in the moment. I was 24 and I felt disappointed that I had let my team down by getting hurt. I had to take 3 months off of work. I didn’t realize I would have these long lasting results physically. If I had I probably would have taken better care of myself. If was one of those moments in your life that defines you. But defines you in past tense because in the moment you don’t know it’s going to be a big watershed moment.”


“What do you think has you in the right place at the right time?”

“I think it’s perception. The inquisitiveness has something to do with it. You either accept things as they are or you ask questions. If you accept things as they are they pretty much stay the same but if you keep looking for a specific person or experience you typically find what you’re looking for.”

jesse-6“Even though I worked for 10 years as a firefighter I feel that working at YouCaring is the noblest work I can do. It challenges me every day to be better as a person and look for the empathetic side of myself. We become jaded because we see so many horrible stories but then it also becomes impossible to ignore these people’s suffering so that inspires me to come to work and do my best. I feel like I have an obligation to educate people on why YouCaring is the best crowdfunding platform.”

“Why is that?”

“Because we’re free. We don’t charge people money that they need to fund their cause. We give people a great product by putting people into a good light.”

“How are you able to not charge money and still run a business?”

“We ask for a voluntary contribution at the time of donation. We allow them to opt out if they don’t want to donate to us but about 80% do give to us also.”


“What’s the biggest way you feel like you’ve changed since you started working at YouCaring?”

“I’m much more inspired by the people that I work with. We have a lot of people that are advanced in their career and we have a lot of people who are coming into their career and I feel it’s my obligation to teach people the path because I’ve been through a lot of it. I’ve made plenty of mistakes and I have good, practical knowledge to share with my team. It’s also really good for me to be around other creatives. Like Svetlana, she inspires me to be more compassionate and to be more excited about the work we’re doing. My tendency is to be more analytical and left brained.”

“What’s one of your dreams for your life?”

“I want to have a legacy. I want to be remembered as a good person. As I get older that becomes more important to me. I want to reflect that I was different. Not just another face in the crowd. I want to visit every country in the world. I have a 20-year-old son, I want him to be proud of me. And I want a cabin in the woods where I can fly fish and write.”

jesse-2“When people are remembering you what are they going to say?”

“He was honest. He was transparent. He didn’t bullshit anybody. He was funny, but there was an edge to his humor. He did a good job. I don’t need to be slapped on the butt and told ‘good job’, but I want people to respect me for who I am.”

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October 22, 2016