Why Justin Gordon Started a Second Newsletter

Justin Gordon has two newsletters. Just Go Grind covers founders and investors and isn't tied to a place. LA Grind is a hybrid: local, but aimed at LA's startup and venture crowd. We talked about how the second one grew so fast, why events are central to it, and how he sells sponsorships when most advertisers want a single ad.

A podcast first, then a newsletter that outgrew his job

Justin started Just Go Grind as a podcast in 2018, just before business school at USC. At Vitalize, the VC firm he joined afterward, he ran marketing and community. That meant a newsletter for angel investors and one for founders, built around the best weekly resources. People liked them because they were easy to read and useful.

At the end of 2022 he restarted Just Go Grind as a newsletter built around deep dives on world-class founders. The first was Sam Altman. He researched it for 30 to 40 hours over about two weeks, while still working full-time. A few months later the list was around 6,000 or 7,000 people and he had a sponsor for four editions.

That was enough. He quit in May 2023 and paused the podcast while he focused on the newsletter.

21,000 readers, and no segmenting

Just Go Grind is at 21,000 after a couple of list cleans. It has been as high as 25,000 or 26,000. His rule is to always clean your list. He turned paid ads off at some point because the numbers have to make sense on the back end.

I pointed out that 21,000 founders and investors is worth far more than 20,000 general local readers. Justin's survey shows a wild mix: multi-billion dollar founders, tier-one investors, and plenty of people who just want to learn from founder stories.

He doesn't segment that list. If you split an audience, you have to send each group different content, and for Just Go Grind one deep dive works for everyone. He is trying segmentation on LA Grind, which has a welcome survey inside beehiiv.

Why LA Grind made sense

Justin has lived in LA since 2018, went to business school there, and knows its startup and venture world. Years of hosting events had built a Luma list of about 1,300 people, which he chose not to import into the newsletter, so every subscriber opts in and opens stay high.

He liked the local newsletter model and saw a way to combine local events with LA venture deals. His honest reason is optionality. It doesn't take much time to run, it opens doors for events, investing or future businesses, and he expected it to be a fun side project first.

Even in LA, deal flow varies week to week. Some weeks there are plenty of venture deals and some weeks there aren't, and he is still working out what that section should become.

Events are the whole model

Justin says demand for in-person is higher than ever with AI everywhere. About 550 to 600 people have filled out the LA Grind welcome survey, and nearly everyone wants some kind of event.

He doesn't just do happy hours. He has run basketball games, beach days, founder retreats, hikes and comedy shows. The pitch to attendees is simple: do the thing you wanted to do anyway and meet relevant people. At a recent hike, about 25 people showed up. One told him he got to burn 600 calories and meet people relevant to him.

Events also change what segmentation means. Some are open to everyone. Others, like an upcoming founder dinner for six to ten VC-backed founders, are curated. He is thinking about separate events for small business owners, VC-backed founders and investors, because sponsors pay differently for each. Sponsors line up for VC-backed founders. A mixer for aspiring coffee shop owners might be a $10 or $20 ticket.

His poll on pricing at $29, $49 and $99 got "maybe, I need more details" as the top answer, and a real chunk of people interested at some price. He is also making an LA founder guide, free, with sponsors behind it. A poll showed most people wouldn't pay for it.

How LA Grind found its first subscribers

The first couple hundred were organic, mostly on LinkedIn, where he has about 8,000 or 9,000 followers. He also has around 41,000 on X, but LinkedIn works better for LA because that audience is local. He also emailed a couple dozen LA VCs: this is a new LA newsletter, tell me if your portfolio companies are hiring, here's the sign-up link.

He started Meta ads at roughly 200 to 300 subscribers. The ads target "curated events and standout stories for LA founders, investors, and operators." He tests creative every week or two, using ChatGPT or Midjourney for images and Canva for the text. The version that worked best had "LA startups and VC" with a line at the bottom about curated events and standout stories.

Organic growth still continues, and he sees people sharing the newsletter. He doesn't have a referral program yet.

Two subscribers for one ad dollar

LA Grind subscribers cost about 70 cents on average. Just Go Grind costs more per subscriber because it isn't local. He recommends Just Go Grind to people who join LA Grind, so one ad dollar buys two subscribers across the two newsletters.

That led him to a thought: why not run an SF Grind, a New York Grind or an Austin Grind, collect cheap subscribers, and funnel them toward Just Go Grind? Or launch a niche newsletter that founders would also want, and recommend three. He admitted time is the limit.

Design, sales and package deals

He paid a designer from Pixels to design Just Go Grind, then reused the same template for LA Grind and only paid for custom headers. The market is crowded, and many LA business newsletters look dated. Setup for LA Grind took about 30 hours, and now it takes 3 to 5 hours a week. Even if you can't pay a designer, a few hours in Canva puts you ahead of most.

For sales, his team keeps targets in Airtable and does cold outreach, warm outreach and social. For LA Grind, a contact he already knew sponsored the first four editions before launch. For the podcast relaunch, he lined up a sponsor before the first episode: he recorded the episode with the company's founder, then pitched their brand person on a bigger package. It covered the podcast, the newsletter, social posts and a relaunch event.

His take on single ads: he stopped selling one-off newsletter placements. He builds packages with several touch points, because it works better for the brand. I told listeners to do the same locally. A local sponsor could get a podcast guest spot, Instagram shout-outs, a newsletter mention and a permanent article on your site.

His advice

Get started, keep going and stay open to opportunities. Justin doesn't know where LA Grind leads, and he's fine with that.

He also runs "serendipity calls," 15-minute calls booked through a calendar link at the top of every LA Grind edition. He reserves an hour a week, books two or three weeks out, and when the four slots fill, that's it.