Aggressively Human: Online Business in the Age of AI, Algorithms & Automations

Two hearts and heads are better than one: Collaboration with Emma Whittard and Karen Worthy


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Partnerships are everywhere in small business: business partners, project collaborators, behind-the-scenes co-creators, podcast co-hosts (hear our origin story!). But we don’t talk enough about what makes them actually work. If managing yourself is hard, imagine navigating the commitment (and the scheduling tetris) of two people.

Emma Whittard (mindset coach) and Karen Worthy (executive career transition coach) had their “business meet cute” in one of Jessica’s classes. What started as simple client referrals turned into collaborations, a shared offer, and even Emma supporting Karen’s business behind the scenes. From the first casual chat to co-creating paid offers, sharing clients, and navigating logistics (like money, time zones, and email volume), we talk about how they built trust without a contract, how they make decisions, and what it means to do good work together.

We talk about the emotional labor of collaboration, the unspoken agreements, and what it takes to prioritize relationship over revenue in a world that teaches us to keep everything transactional.

Before teaming up with someone, listen to the foundation of what makes this collaboration work.

* How a casual class connection became a long-term collaboration

* Why their “Base Camp” offer came after the referrals, not before

* What they’ve learned about setting boundaries, expectations, and pricing

* The value of emotional support, operational partnership, and sounding boards

* Navigating logistics: scheduling, tech, shared values—and the messy middle

* Why trust (not contracts) is what makes these kinds of partnerships work

“We also both said upfront that our relationship was more important than the business together. So the relationship first. That means that hopefully we won't get into a situation where there's something icky happening and we can't address it, or it sort of ruins things. So again, it is back to values and priorities again.” - Emma Whittard

About our Guests

Emma Whittard | LinkedIn

Karen Worthy | LinkedIn

Base Camp Offer

Connect with Us

Listen on Spotify

Listen on Apple Podcasts

Connect with Meg and Jessica

Meg Casebolt

Jessica Lackey



This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com
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Aggressively Human: Online Business in the Age of AI, Algorithms & AutomationsBy Meg Casebolt & Jessica Lackey

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