21: Bragging Rights: Get Comfy with the Uncomfortable
Second Cup Sessions29 Heinä 2025

21: Bragging Rights: Get Comfy with the Uncomfortable

In this honest and hilariously relatable episode, Calley and Kati dive into the awkwardness of promoting your own business—why it feels cringey, especially for women, and how self-deprecation often sneaks into our everyday language. They reflect on how easy it is to rave about a friend's store but how uncomfortable it feels to say the same things about your own.

The conversation includes role-playing introductions of each other's businesses (with lots of laughter and pen drops), a deep dive into imposter syndrome, and personal stories from their early days of entrepreneurship—including creepy warehouse beginnings and the grind that built their brands.

They explore how minimizing your work is a disservice to the past you who put in the long hours, took the risks, and built something from nothing. The episode ends with a challenge: get on social media and brag about your business like you would your best friend's—and tag @SecondCupSessions so they can hype you up right back.

It's a feel-good, fire-you-up kind of episode that reminds you: your hard work is worth celebrating.

Jaksot(30)

30: Cheers to Season 1

30: Cheers to Season 1

It's the end of Season One! We're a little happy, a little sad, and a lot caffeinated as we wrap up this first season of Second Cup Sessions. In this episode, Kati and Calley trade questions, crack ea...

14 Loka 202543min

29: Marketing With Purpose:  Crafting Stories That Connect

29: Marketing With Purpose: Crafting Stories That Connect

In this episode of Second Cup Sessions, we sit down with marketing strategist Mary Czarnecki to unpack how small business owners can use stories with intention—not just for entertainment, but to build...

7 Loka 202540min

28: When "Making It" Looks Different Than You Planned

28: When "Making It" Looks Different Than You Planned

In this episode of Second Cup Sessions, Calley and Kati get real about how their visions of success have shifted over time—from dreams of infinity pools, multiple store locations, and picture-perfect ...

30 Syys 202545min

27: Finding Your Ideal Customers

27: Finding Your Ideal Customers

In this episode of Second Cup Sessions, Calley and Kati dive into the ever-important question: who is your ideal customer? From the quirks of Pacific Northwest culture to the realities of who actually...

23 Syys 202538min

26: Stronger Together with Omega NW

26: Stronger Together with Omega NW

In this episode of Second Cup Sessions, we're joined by Jana and Susie, the powerhouse duo behind Omega NW, a Portland-based nonprofit that helps women transition out of addiction, homelessness, incar...

16 Syys 202538min

25: Simplifying Markets

25: Simplifying Markets

In this lively and heartfelt episode, Calley and Katie sit down with Sarah, founder of Simplicity by Sarah, to dive deep into the world of vendor markets—the highs, the headaches, and the huge potenti...

26 Elo 202548min

24: Sugar, Spice, and Small Business Life

24: Sugar, Spice, and Small Business Life

This week on Second Cup Sessions, we sit down with Hannah Luttrell of Luttrell's Little Cookie Company to talk about the sweet (and sometimes messy) reality of running a business from home while raisi...

19 Elo 202543min

23: Overthinkers Anonymous

23: Overthinkers Anonymous

In this episode of Second Cup Sessions, Calley and Kati tackle a challenge every business owner has faced at some point—analysis paralysis. You know the feeling: too many options, too many "what ifs,"...

12 Elo 202536min

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