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👯‍♀️ Special Guests: Sammy & Gracie (my twin daughters)

🗓️ Recorded after Take Your Kids to Work Day 2026

This has quietly become one of my favorite episodes to record every year.

My daughters—11-year-old identical twins—have been on the podcast a few times now, and each year the conversation shifts a little as they get older, more independent, and more aware of what’s going on around them.

They’ve grown up watching me leave my corporate job and build this business from home. In past years, they’ve “come to work” with me—but this year, they went to work with their dad instead.

So we recorded these conversations separately, and I asked them almost all the same questions.

What came out of it was equal parts funny, honest, and surprisingly insightful.

There’s a lot we talk about on this podcast—systems, strategy, making your business easier to carry—but this episode is a good reminder that sometimes the simplest perspectives are the ones that stick.

If you’ve ever wondered whether the systems running your business are actually helping—or quietly making things heavier—this might be a good place to start. I offer backend systems audits for both 17hats and Flodesk that review what’s working, what’s fragile, and what deserves your attention next. Learn more at kristenlettini.com/audits.

Text Kristen your thoughts or feedback about the show

Lynn Harris, a culture-shifting producer, award-winning journalist, and founder of GOLD Comedy, shares her non-linear path from journalism to comedy to building a community-driven business.

We talk about what it really looks like to run a business when you don’t fit the typical “founder” mold — from testing and growing an idea over time to the role of community, the behind-the-scenes realities, and why you don’t need to have the whole path figured out to get started.

Learn more about Lynn and GOLD Comedy at goldcomedy.com or follow on Instagram @goldcomedy.
(use code GOLD10PERCENTOFF for 10% off if you join GOLD Comedy)

If you’ve ever wondered whether the systems running your business are actually helping—or quietly making things heavier—this might be a good place to start. I offer backend systems audits for both 17hats and Flodesk that review what’s working, what’s fragile, and what deserves your attention next. Learn more at kristenlettini.com/audits.

Text Kristen your thoughts or feedback about the show

You’ve had this happen before.

A potential client says yes.
You send the quote, contract, or invoice…

And then things go quiet.

Suddenly the questions start creeping in:

Did they change their mind?
Did they forget?
Should I follow up?

This moment is incredibly common in service-based businesses — and it’s where a lot of deals quietly stall.

In this episode, I'm walking through the "follow-up gap" — that space between someone saying “yes” and actually completing the next step — and why it often has less to do with interest and more to do with timing, attention, and how we communicate.

If you’ve ever hesitated to follow up because you didn’t want to seem pushy, this episode will shift how you think about it.

***

Free Workshop: Build a Smarter Document Reminder Strategy in 17hats

Design well-timed email and text reminders that feel personal — even though they’re automated.

You’ll learn how to:

• map out reminder timing for quotes, contracts, invoices, and questionnaires
• choose between email and text follow-ups
• refine your messaging so it sounds like you

→ Save your spot

If you’ve ever wondered whether the systems running your business are actually helping—or quietly making things heavier—this might be a good place to start. I offer backend systems audits for both 17hats and Flodesk that review what’s working, what’s fragile, and what deserves your attention next. Learn more at kristenlettini.com/audits.