No emails, no meetings, just time to reset—Kate is about to find out how that feels.

In this season ender of Whiskey Fridays, Kate and John reflect on the busy fall and Kate’s upcoming six-week sabbatical from Wanderwell.

Kate discusses how she’s prepared her business for her time away.

They touch on the importance of taking time off, delegating tasks and setting boundaries - wrapping up the season with a look ahead.

Resources:

Learn more about Kate Tyson:

• Wanderwell
• Connect on LinkedIn
• Sign up for Kate’s Newsletter

Learn more about John Gerber:

• Unlawyer
• Instagram: @un.lawyer
• Connect on LinkedIn

Featuring Music by Billy Dufala:

• @bdufala

Kate chats with Nic Antoinette about her plan to take an “adult gap year” in 2025: Nic will hit pause and step back from most of her business and work life for 12 months. Nic shares her journey with work, autonomy, and the struggle between traditional productivity standards and personal freedom. They dive into how to prepare for such a big shift and how Nic is approaching her year off.

About Nic Antoinette: Nic Antoinette is a business owner, writer, and creator who has spent the last several years exploring the balance between personal freedom and work. Nic is currently taking a year off to pause her business, reflect on her life, and better understand herself. Through this process, she hopes to gain deeper clarity and reconnect with what truly matters to her.

Resources:

Learn more about Nic Antoinette:

• Nic Antoinette on Substack
  
  

Learn more about Kate Tyson:

• Wanderwell
• Connect with Kate on LinkedIn
• Sign up for Kate’s Newsletter
  
  

Learn more about John Gerber:

• Unlawyer
• Instagram: @un.lawyer
• Connect with John on LinkedIn
  
  

Featuring Music by Pete Angevine:

• @pete_angevine

Kate talks to Neily Jennings of AORTA Cooperative about the organization's process of designing a transparent, equitable, and just compensation framework for their team. They discuss the history of AORTA’s compensation experiments and how they have worked to embed values of equity and justice into their pay structures. Neily also offers practical advice for businesses and organizations seeking to approach pay structures with more transparency and values alignment.

About Neily Jennings & AORTA

Neily Jennings manages finance and operations at AORTA Cooperative, a worker-owned co-op offering facilitation, consulting, coaching, and training to support organizations in practicing democracy and building strategies for liberation. With over a decade of experience, Neily has helped AORTA evolve its pay structure to align with its values, political analysis, and business growth. As a democratically run cooperative, AORTA's workers are also its owners, practicing collective decision-making. Neily's work reflects a deep commitment to equitable systems and transformative change.

Learn more about AORTA:

• Aorta’s Website
• Instagram: @aortacoop
• Connect with Neily on LinkedIn

Learn more about Kate Tyson:

• Wanderwell
• Connect on LinkedIn
• Sign up for Kate’s Newsletter
  
  

Learn more about John Gerber:

• Unlawyer
• Instagram: @un.lawyer
• Connect on LinkedIn
  
  

Featuring Music by Billy Dufala:

• @bdufala
  
  

Kate sits down with Jessica Norwood for a conversation about reimagining finance and capital through building an anti-racist and reparative economy.

Through her guiding question "what would it look like if the economy loved Black people?", Jessica asks us to lean into our imaginations to transform our economic systems. They talk about how her organization, Runway, and the recently launched Rooted Fund practice reparative finance through lending decisions and entrepreneur support that prioritize long-term community relationships over extractive returns.

Expanding the definition of investment, Jessica invites listeners to consider how everyone can be an investor in creating a more just and loving economy.

About Jessica Norwood:

Jessica Norwood is an entrepreneur, investor, artist, and philanthropist who has spent her career exploring the ways that money can be an expression of repair and spiritual care. She is a serial social entrepreneur, who works with a community of investors to provide believe-in-you money in order to create an economy that loves Black people, and encourages others to do the same.

Resources:

Learn more about Jessica Norwood:

• Buy ''Believe-in-You Money'' by Jessica Norwood
• Jessica Norwood's website
• Runway
• Connect on LinkedIn

Learn more about Kate Tyson:

• Wanderwell
• Connect on LinkedIn
• Sign up for Kate’s Newsletter
  
  

Learn more about John Gerber:

• Unlawyer
• Instagram: @un.lawyer
• Connect on LinkedIn
  
  

Featuring Music by Billy Dufala:

• @bdufala

Business owner compensation is not as straightforward as it may seem.

Kate and John discuss challenges with balancing an owner’s personal needs with those of the business, technical aspects of compensation that sometimes confuse owners, and, most importantly, what owner compensation can tell you about your business.

Learn more about Kate Tyson:

• Wanderwell
• Connect on LinkedIn
• Sign up for Kate’s Newsletter
• Kate’s Article: Getting Paid
  
  

Learn more about John Gerber:

• Unlawyer
• Instagram: @un.lawyer
• Connect on LinkedIn
  
  

Featuring Music by Billy Dufala:

• @bdufala
  
  

Ever wonder what kind of investor relationships are actually worth it and what might be the best fit for you?

John talks through the four types of investors—friends and family, crowdfunding platforms, angel investors, and strategic investors— diving into the good, the bad, and the awkward of funding for small businesses.

He also explores the reality check that every founder faces: sometimes you need the cash more than the ideal partnership.

Learn more about Kate Tyson:

• Wanderwell
• Connect on LinkedIn
• Sign up for Kate’s Newsletter
  
  

Learn more about John Gerber:

• Unlawyer
• Instagram: @un.lawyer
• Connect on LinkedIn
  
  

Featuring Music by Billy Dufala:

• @bdufala
  
  

Kate sits down with Bear Hebert, anticapitalist business coach and social justice educator, to reframe the conversation on how we think about money in our businesses as capitalist critical business owners.

They discuss the freedom that comes from separating our worth from what we charge, and dive deep into the complexities of pricing, accessibility, and the importance of building a community where everyone feels welcome.

If you’re grappling with under-earning or trying to balance making a profit with staying true to your values, this chat with Bear is the refreshing perspective worth tuning into.

Learn more about Bear Hebert:
Bear Hebert (they/them) is an artist, anti-capitalist business consultant and social justice educator. Self-employed since 2014, Bear helps tiny business owners build thriving livelihoods while sidestepping the traps of capitalism. Their side gig is teaching men+ how to unlearn patriarchy.

• Bear Coaches
• Freely: an anticapitalist guide to pricing your work
  
  

Learn more about Kate Tyson:

• Wanderwell
• Connect on LinkedIn
• Sign up for Kate’s Newsletter
  
  

Learn more about John Gerber:

• Unlawyer
• Instagram: @un.lawyer
• Connect on LinkedIn
  
  

Featuring Music by Billy Dufala:

• @bdufala
  
  

Kate wants us to think about profit differently. Instead of money lining the pockets of shareholders and business owners, she proposes that profit is a crucial resource to care for all the people in a business. Yes, including employees. She and John discuss ideas from her latest publication: The Radical Business Owner’s Guide to Profit, and talk about shifting from an extractive to a regenerative use of profit.

Resources:

• Kate’s Zine: The Radical Business Owner’s Guide to Profit
• Kate’s Article: Tending Profit
• Whiskey Fridays Episode: Towards Transparent Profit Distribution

Learn more about Kate Tyson:

• Wanderwell Zine Shop
• Wanderwell
• Connect on LinkedIn
• Sign up for Kate’s Newsletter
  
  

Learn more about John Gerber:

• Unlawyer
• Instagram: @un.lawyer
• Connect on LinkedIn
  
  

Featuring Music by Billy Dufala:

• @bdufala