Building a development model on human connection

Jake Hylton went to 19 conferences this year.

“It was a hustle,” he said.  

But going to as many convenings as possible was part of his personal plan as well as the strategic plan for LOOKOUT Publications, a nonprofit news site covering Arizona’s LGBTQ+ community. After all, the organization is built on the values of partnership and collaboration.

“Most funders won’t respond to your emails if they don’t know who you are, and the only way for them to know who you are is to build a relationship with them, and the only way to build a relationship with them is to be where they are, and the only place where they are is at the conferences.” he said.

Hylton has served as the outlet’s executive director since its founding in January 2023, but he’s relatively new to the journalism industry. For him, conferencing is part learning about the news business, part making connections. Before each conference, he develops what he calls his “crazy spreadsheet for funders,” a color-coded document that serves as his personal guide to success. 

Before each conference, he obtains the list of attendees, drops it into an AI application, has it separate the funders from the publishers and scrapes the Internet for the attendees’ photos so that he knows what every single person looks like. He makes sure he has their names, emails, roles, and what foundation they’re with. Then he checks what regions they serve and which issues they fund. 

“Is this a funding possibility?” he asks himself. Based on the potential, he then prioritizes who’s on the spreadsheet, labeling them Priority 1-5 based on who he needs to meet. “If I can get to my fives, I will, but I need to make sure I get through all my P1s and P2s, and my P3s are people I’ve already had conversations with that I need to just continue chatting with.” He adds nearby meeting spaces to the spreadsheet, such as restaurants and coffeehouses.

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When he finally meets a funding officer, he doesn’t pitch his organization or ask for money. 

“I never talk about the things I do, and I don’t talk about the things they do. I just treat them like a person, and we have human conversations. I get to know who they are. I get to know where they live. I get them talking about their family and their kids – and maybe one of the few times that they’re in a work setting surrounded by hundreds and hundreds of people, they feel seen. And sometimes on a human level, that’s all you really need,” he said.

“Not everything works out. Funders are like dating. You don’t go on a first date and say, ‘So are we gonna get married?’ If you go up to a funder and the very first thing you say to them is, ‘How do we get to be in a partnership and when will you give me money?’ That doesn’t work.”

His system is part of how he’s raised hundreds of thousands of dollars and made LOOKOUT a model for fundraising success among others in the industry.

LOOKOUT launched as a monthly Substack publication in January 2023 before receiving a $400,000 grant and an incubator invitation from the American Journalism Project in May, which helped it become a full-time business. Hylton and his partner, founder and editor-in-chief Joseph Darius Jaafari, raised an additional $74,000 in the last quarter of that year. In 2024, they brought in another $345,000, and so far this year, another $475,000, not counting AJP funding. With that, their team of 2.5 people produces three newsletters a week, a quarterly print magazine, and runs 40 events a year.

Cultivating community

Connecting, clearly, is the crux of the publication, and Hylton said bonding with community members is the most rewarding part of his job. Nonprofit publication leaders often ask him how LOOKOUT can hold so many events a year. The key, Hylton said, is partnerships. “The community benefits the most,” he said. “It’s not enough to just give you information. You should also be able to understand who that information affects and who you can go to to not feel alone.”

The publication links with community organizations to share the workload and bring in collective audiences for events such as poetry nights, community workouts and inclusive gyms, trauma-healing workshops through drag.  Each event costs the publication about $200. Forty events can be tiresome so the goal for next year is to pare it down to one monthly LOOKOUT signature event, hold smaller ones that others will manage, and recruit volunteers to chip in.

He recently was elected to the board of the Institute for Nonprofit News with a mission, he said, to use his experience and privilege to advocate for identity publications and publishers for marginalized communities. His supporters speak highly of his energy, creativity, and deep understanding of people.

“For me, building relationships makes me feel less alone. It also means that if either of us needs something, there’s a resource. It’s lonely to run a news organization. Everyone’s doing the same thing and figuring it out on their own. Why is everyone doing the same thing and making the same mistakes when there are people who’ve already gone through those mistakes and have figured out how to make it better? So for me, it was like: How do we work together?”

His work journey began at age 10, when he apprenticed under his mother in her restaurant consulting firm. His first love is theater, where he worked in his 20s, but after an on-the-job accident left him injured, he pivoted to tech startups.  After working for several of them, he was miserable. 

“I’m a storyteller, and I don’t know how to be anything but authentic and genuine. Being able to tell the story of what we do in an authentic and genuine way is extremely powerful. The one thing that I will say that I’ve always done in the many careers that I’ve had, and that theater made me good at is building relationships. Authentic, good relationships, not extractive, fake ones.”

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Cite this article

Williams, Monica  (2025, Dec. 11). 19 conferences, one spreadsheet and zero pitches: A look at LOOKOUT’s fundraising success. Reynolds Journalism Institute. Retrieved from: https://rjionline.org/news/19-conferences-one-spreadsheet-and-zero-pitches-a-look-at-lookouts-fundraising-success/