SaaS Made Her Love Services with Jess Chan (Plus New Podcast Alert: The Pretty Good AI Podcast Is Here)

I have two shows for you this week.

First, check out the newest episode of Founder Mode. Then stick around, because I'm launching something brand new: the Pretty Good AI Podcast.

🎧 Listen to Founder Mode Episode 71 here:

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SaaS Made Her Love Services... Aug 27 · Founder Mode 28:43   ​

On the latest Founder Mode episode, Jason Shafton and I sit down with Jess Chan, founder of Longplay. Jess grew Longplay from an email marketing agency into a full lifecycle growth partner for e-commerce brands. She also just made a big move. She stepped back as CEO and became executive chair, handing the day-to-day reins to her longtime partner Rachel.

The conversation covers the real cost of chasing fast growth, why Jess never took outside investors, and what she learned after building both an agency and a SaaS company. Her biggest lesson: most founders solve the wrong problem, and they solve it fast.

I closed the episode with five takeaways, straight from the show:

1. Take the 10-year curve over the one-year hockey stick.
2. Solving the wrong problem faster is still the wrong problem.
3. Use AI to buy back space, not to run yesterday's playbook faster.
4. Choose your hard.
5. Hurt people, hurt people, and that includes founders.

Introducing the Pretty Good AI Podcast

Now for the big news. I'm launching a new show: the Pretty Good AI Podcast. I'm the co-founder of Pretty Good AI, and each episode I talk to operators who run real healthcare practices. No hype. Just how the work actually gets done.

🎧 Listen to Pretty Good AI Episode 1 here:

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You Can't Automate People wi... Aug 25 · Pretty Good AI Podcast 20:06   ​

Episode 1: You Can't Automate People with Katy Zorich

Our first guest is Katy Zorich, VP of People Operations at Zarminali Pediatrics. Katy's team is small. Just three people run people operations for a company with more than 800 employees. Zarminali is a venture-backed pediatric platform. It has raised over $100 million and completed roughly a dozen acquisitions in just two years.

Katy explains how her team keeps up. Every new practice gets a transition-of-services agreement. This spreads changes out over months instead of dumping everything on employees at once. Her team also runs a compensation analysis on every acquired group, rather than changing anyone's pay right away. And they wait to move a practice onto the Athena system until the timing is right, because that switch touches everything.

Katy's team is also rolling out Zarbot, an AI chatbot that answers routine HR questions right away. Before Zarbot, employees sometimes waited days for an answer. Now they get one instantly, any time they ask.

Here's how I summed up the conversation:

Final Thoughts

Both conversations point to the same idea. Growth that lasts comes from strong systems, not shortcuts. Jess built Longplay by fixing the real problem instead of the fast one. Katy's team scales a healthcare company by standardizing the basics and using AI to clear space for people to do their best work.

Watch the new Founder Mode episode, then listen to the first episode of the Pretty Good AI Podcast. Subscribe so you don't miss what's next.

This podcast builds on the Founder Mode newsletter.

Let’s build.

-kevin

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