👋 I’m Justin. I run The LA Grind and The SF Grind and scout for Headline.

Happy Thursday! Today is an experiment. I’ve wanted to expand The LA Grind from one to two editions per week for a while. I’ve also wanted to highlight amazing founders and investors in Los Angeles better. As we close in on 10,000 subscribers to this newsletter, it’s time to expand.

We'll be back to our normal editions every Monday, sharing events, opportunities, venture deals, and more, but Thursdays will be where we test out some new formats.

Please tell me in the poll at the end what you think of this direction for a second weekly edition, I’d really appreciate it!

Let’s get to it.

Today we have a Q&A with Kevin Bailey, co-founder of Understood Care, an AI-native Medicare-covered patient advocacy platform. The company has raised $8.4M, including a $5M seed round and $3.4M pre-seed round, backed by Rethink Education, Zeal Capital Partners, 1984 Ventures, and Y Combinator.

What's the backstory?

So my co-founder Sam and I actually met online. We had both just gotten out of other co-founder relationships and were ready for something new. We spent some time together and really resonated on our working style and goals. We decided to give working together on a startup a try.

While exploring what sorts of business we should try to build, we stumbled across healthcare advocacy, a huge, underserved, and brand new category where we knew we could make a massive impact. Put up a quick painted door test, and the pull from the market was unlike anything I’ve ever seen before.

Tell me the story of how you got your first customer.

We actually got our first customer through Facebook ads! We had a landing page that was integrated with Hubspot, and that is how we orchestrated our early conversions.

How has the growth strategy evolved since then? What was one thing that worked surprisingly well to help you grow?

We have micro-optimized our patient experience and onboarding process. Everything from button placement, to how patients are able to schedule appointments, to the intake staff, to patient happiness tracking, it has all been painstakingly hand crafted and closely monitored. All these things are in place so that every patient gets seen as quickly as humanly possible, and that no patient is ever left behind. We think delivering the best possible experience to our patients is the best way to grow the business.

I wouldn’t say it is surprising that caring about our customers has helped us grow. I guess one thing that was surprising was that disabling scroll on the mobile onboarding flow did meaningfully improve conversion rate, which is surprising.

What's something most people either don't know or misunderstand about how businesses in your industry actually make money?

We do receive this question from our patients a lot, but we are a medicare covered service. Most of our patients pay $0 out of pocket for our services.

Have there been any memorable "Oh shit" moments where you thought the whole thing might fall apart?

There have been a handful. I think the most memorable one was when I took my first week off to celebrate an anniversary, and something went wrong with the way our internal portal displayed appointment times and no patients were being seen at the correct time. That was very stressful… Murphy’s law at play.

What's one important part of the business model or strategy that you've changed your mind on since starting?

How much AI can optimize workflows. Going into this I was optimistic that AI could definitely help. But seeing first hand how much better our caretaker’s workflows are when augmented by AI has been eye-opening. At this point I think we’re just scratching the surface of what AI can do.

What was the last purchase of less than $1,000 that made a serious impact on your life?

I am not sure if this counts, but we have a ton of Celsius in the office. I am sure having celsius everyday isn’t that good for me… but the ROI from a business perspective on it is through the roof. At least 40% of the diffs I push have got to be attributed to Celsius.

What are the 2-3 AI tools you use the most? Why?

CLAUDE CODE with a max subscription. Literally a game changer. I know some folks prefer Codex, but Claude is a bit better for me. I usually have 2-3 instances of Claude Code going at any time. I finally feel like the limit of how quick we can push features is how quickly I can read the mark down files. It’s like magic.

What's a favorite under-the-radar spot in LA that you keep going back to (and why)?

Not quite in LA, but Nick’s in Laguna Beach. Literally everything on the menu is a 10/10.

Interested in joining The LA Grind Club?

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Here’s what Will, an investor in over 100 companies, had to say about the club:

“The LA Grind Club has some of the most genuine people in LA's startup ecosystem. Every event I've been to, from the holiday party to the basketball runs, I've walked away having met people I actually keep in touch with.“

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Here's what's top of mind for me today: Figuring out what an annual summit for The LA Grind looks like.

I've hosted 50+ events over the last 10 months since launching The LA Grind. Producing a larger summit with 100+ people annually, eventually expanding over time, has been an idea I can't shake.

But I'm currently focused elsewhere, growing The LA Grind Club, hosting great events for members, ramping up events in SF for The SF Grind, working with sponsors across both cities… There's a lot happening.

When I have an idea I can't shake, though, I typically end up doing it.

LA has big events annually like the Upfront Summit, LA Tech Week, Expo West, The Montgomery Summit, and more.

The question is: How can I create a differentiated experience that is highly valuable to the audience?

That current answer is I’m not sure… but I’m working on it.

What I know I want is amazing speakers and plenty of opportunities for attendees to connect with each other, which is often the most valuable part of any summit or conference. I'd want it to be a memorable experience that people cannot wait to go to every single year.

When I have explored this idea in the past, people told me I needed six months to do a big summit, even a one-day event, to do it well in terms of prep, getting everything in order: speakers, sponsors, venue, etc. Maybe that’s why I haven’t committed to it yet.

But I want to make it happen. Stay tuned, more updates to come.

Talk Shop Media is an LA-based tech PR agency that helps brands at any stage break through the noise and earn the coverage that actually moves the needle. From emerging startups to established names, they build and execute media strategies that get you in front of the right people, press, influencers, and beyond. If you're ready to turn your story into momentum, let's talk: talkshopmedia.com 

Marc Hankin of HPL Law advises inventors and high-growth teams on patents, trademarks, copyrights, trade secrets, and licensing. Before your next fundraise, launch, or M&A chat, know where you stand by talking with Marc, who you can reach at [email protected]. Marc can often be found at startup events in LA and has been one of the biggest supporters of The LA Grind since its inception!

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See you next week,

Justin

P.S. Want to connect?

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