Last year, Matt Dimmer was burning the candle at both ends trying to launch The Extra Mile, a nonprofit designed to allow people to donate unused frequent flyer miles to the family members of terminal cancer patients. Working a demanding day job as a creative director at an ad agency while struggling to set up his fledgling organization, he was fueled only by the memory of his late father, Pete, and some innate networking skills. Given that Dimmer’s idea is such a no-brainer, it seemed like only a matter of time before his org was up and flying. As he said in his interview with Co.Exist at the time: “There’s a need for this, and I’m going to make it happen.”

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Eight months later, Dimmer is still struggling, but he just took a massive first step. And the second chapter of his story holds plenty of encouragement, inspiration, and information for anyone out there trying to build their own organization or foundation from scratch.

Let’s start with the bad news: After collecting around 140,000 miles via a website partner called Mileage.org, Dimmer found himself and his organization totally gutted when that site went out of business in November 2013. The miles disappeared, as did his only third-party avenue to collect them. The setback was so upsetting, he remains reluctant to talk about it. Meanwhile, the major airlines themselves–who maintain plenty of donation accounts with large, well-established charities like the Make-A-Wish Foundation–remained largely non-responsive to Dimmer’s solicitations. (Delta has graciously offered two flight vouchers.) “It’s the same story as before,” Dimmer says. “I need a third party to help me, or an airline to step up. I need to be able to put people on planes. So whether it’s corporate donations from a funding standpoint or it’s a partnership with an airline… A car can’t go anywhere without gas.” He’d lost a year of hard-earned donations, but Dimmer, the master networker, kept pushing. He established a partnership with travel advertising platform Sojern, who now offers The Extra Mile free advertising space on boarding passes. He set up a charity account with American Express to collect donations of Amex points, which can be converted directly into miles. He continues to establish relationships with philanthropic-minded corporations in the hopes that one of them, someday, will help him get his foot in the airline door. Mostly, he says, “I started boot-strapping,” creating personal accounts with each airline to accrue mileage donations directly, paying the transfer fees out of his own pocket. This system, naturally, has led to some “weirdness,” as he calls it. “There was a guy who reached out and was like, ‘Hey, I’d love to donate, but these accounts are in your name,’” Dimmer recalls. “I was like, Yeah, dude. No one will give me a corporate account, so this is the only way to do it. If you don’t feel comfortable about donating to a guy who runs this outside of his day job based on the fact that he lost his dad to cancer, don’t donate.” Dimmer believes that transparency about TEM’s status is helping him, not hurting. “For me in life, that’s how I operate,” he says. “Without begging for help or trying to look desperate, by telling people the state of The Extra Mile with total transparency versus acting like we’re a big company, it hopefully adds to their propensity to want to help.” Now for the good news: This past weekend, The Extra Mile completed its first flight, using donated Amex points, with a Today Show cameraman in tow. The spark came last October, when Today tweeted that they were on the hunt for people doing good to profile in their “Hope To It” web series. “I saw that tweet and jumped all over it,” said Dimmer, who rallied his social media network to support his cause. “A couple months later I got an email [from Today] saying, ‘We’re interested in talking about this, do you have anything major coming up?’”

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That was literally around the time that Mileage.org went belly-up, so I called the producer and was like, ‘I’m going to be completely transparent with you. This is the worst point in the history of this organization. I just lost my mileage partner, I’m treading water, but I’m looking to complete a flight. So if you’re interested in chronicling the first flight, I have something that’s press-worthy.’ And he was like, ‘We’re in.’”

The recipient of TEM’s first flight was JJ Rolle, a 53 year old Seattle-based actor, singer-songwriter, and street performer, originally from Valdosta, Georgia. Rolle, who is openly gay, has a story straight out of central casting: He and his dad had a falling out 23 years ago over both his sexuality and his peripatetic artist’s lifestyle; although they’d been trying to mend fences, they still hadn’t seen each other in over two decades. Then the phone rang. “My sister called me and said my father had a stroke and it didn’t look good,” says Rolle. “She gave me the hospital number and, speaking with his nurse, I learned of masses in his liver and gallbladder, as well as his kidneys failing and being septic. I knew I had to see him.” Rolle also knew he lacked the funds to make that happen. (In fact, our interview was conducted via email, because his phone has recently been cut off.) “I was frantically trying to find a way to him,” Rolle writes. “I couldn’t possibly afford a ticket. Even with the bereavement discount of 50% from the airlines, you must still pay full fare and, after you prove the emergency is real, you get a refund of 50%. I tried churches, Travelers Aid, anything that came to mind. I found a website called AngelFlightWest.org and contacted them. Unfortunately, they don’t cross the country, only the western U.S. However, the representative told me of The Extra Mile, and I got in contact with them. I was desperate, and they could only say yes or no, so I went for it.” “Divine intervention” is how Dimmer explains the email from Rolle. “This guy wrote me, hasn’t seen his dad in 20 years, traveling, working random jobs, hasn’t been able to get back. The stars aligned,” he says. “I love it because it’s a father-son story like mine, which couldn’t be more fitting for the first flight.” Rolle gave Dimmer a hospital code word so he could speak to nurses and vet the legitimacy of the situation, and on Friday, May 2, Dimmer used his personal (non-TEM) frequent flyer miles to fly from Denver to Seattle; he and the Today Show staffer then accompanied Rolle on his flight to Georgia, where they rented a car and drove to Macon. “Standing in the hospital room with JJ was moving,” Dimmer reports. “He talked to his father, who was semi-unresponsive and connected to a ventilator with his eyes closed. When his father squeezed his hand, we all knew that the connection had been made, and that the trip was a success.” As someone with first-hand experience of how it feels to stand at a similar bedside, Dimmer admits he had to leave the room and cry. “It was all too familiar for me,” he says. “What I experienced two years ago felt like it was yesterday.” For Rolle, the weekend was an opportunity to change a part of his past. “When you get news of this kind about a loved one, your mind is constantly on that person and you go through your entire life with that person, remembering the good and the not-so-good,” he says. “All you want to do is be there with them. It’s an opportunity to resolve any issues that one might regret not having the opportunity to. I’m really happy that’s not the case for me.”

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After 5,500 miles and three airports in three days, Dimmer is both energized by his first completed flight, and simultaneously aware that he’s still got a long way to go. Still, “it’s something of a relief,” he says. “I learned that hand-delivering a candidate is a lot of work, and isn’t a sustainable model for The Extra Mile. I need to divvy up some of the responsibilities of the organization, so I can get more people involved, to accomplish more, quicker. We need to get a system in place that will allow for the individual to receive the miles, points or whatever else we’re able to offer, and take responsibility to get themselves to the destination. “Mostly,” he says, “this first trip proved that this can happen–to me, and hopefully to lots of other people and organizations that can help us in the future.” With one flight down and ideally countless more to follow, his message remains the same as it was on day one: “I’m trying to help people, so help me help people.”