Inside The Garage SF with Michael Gallagher

I moved to California amidst the pandemic. I left Chicago because my first lockdown winter was brutal, and facing another one was too much to handle. Fortunately, my roommate from undergrad at Northwestern reached out about a room that had become available in his house in Los Altos. We were able to relive our college days for a while, but when things started to reopen, he promptly moved to New York.

After he moved, my tiny Northwestern Bay Area network shrunk to just a single node. There were hints of other Wildcats in the area: a post about one finishing her PhD at Stanford, a man jogging in his PA shirt. However, I didn't know how to plug myself back in like I did in Chicago. That was until I met Keyaira at the TGSF Kickoff Mixer.

It felt like school when we were all in the same room at the event. I immediately saw some familiar faces, and Keyaira put us straight to task brainstorming ideas for getting alumni more involved at Northwestern’s SF campus. One of those ideas was Co-working Fridays. As a founder bouncing between cafes, WeWorks, and my friends' offices, I quickly affirmed that I would be there every Friday.

That ended up being an underestimate. I learned that The Garage SF was taking applications for Entrepreneurs in Residence (EIR), and was over the moon when my company was accepted. I finally had a perfect opportunity to reconnect with other NU alumni while growing my business.

I started working on building new startups about two years ago with my co-founder, who was my PM at our last company. My decision to join the partnership was equal parts “if I don’t do it now, I’ll never do it” and “I should learn new skills in case AI steals my job.” We built several products across various verticals, including dev tools, fintech, and geospatial data, all the while keeping the ship afloat by contracting with other startups.

At our latest contract, we uncovered an opportunity. We were building an HOA software platform and realized there was a massive communication issue in large communities that we could help solve by leveraging AI. We started talking with board members in different communities to validate the problem and learn about the space.

We learned it's a growing $8bn+ market with undifferentiated competition. HOA directors all had a common frustration: they had joined the board to solve a problem, usually a financial issue where the previous board members had misspent funds. We latched onto this problem and began developing a spend management tool designed specifically for HOAs.

Since joining as an EIR, I have worked with my cofounder out of the SF campus most days. During that time, we’ve gotten close with JP, the office manager. JP is awesome, and when he heard from a Kellogg alum that she was having issues at her HOA, he put us in touch. We met for the first time on the same day as the first Co-working Friday and closed our first customer!

I returned to the office, still shaking, and fortunately, the food had arrived. I was glad I had time to regain my composure before introducing myself to the amazing Wildcats that came out. I met other founders, VCs, potential customers, and potential friends. I also gained some valuable insights.

We closed out the day with a little competition by playing board games. And afterward, hit a happy hour to punctuate a long day of working and socializing. Reflecting on this experience, I’m looking forward to building strong connections with everyone I’ve met here. Everyone I talked to seemed eager to return to the space, so I hope we have more opportunities this summer to host! I’m also excited to see who will join us next month. If you’re interested in attending the next one, check out the events tab on the TGSF website.

All in all, our first coworking session was a blast. Thank you to Jill, who shared her experiences as both a parent and a founder, Shalin, who pointed me to a data vendor to help source clients, and Keyaira, for organizing a fantastic event that grew The Garage’s network and community here in SF!

If you or anyone you know are on the board of HOA, please reach out to the Bento team at michael@withbento.com