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.
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Featuring Music by Billy Dufala:
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.
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Featuring Music by 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.
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Featuring Music by Billy Dufala:
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.
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Featuring Music by Billy Dufala:
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.
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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.
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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.
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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.
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Kate and John tackle the thorny issue of non-competes: from the weirdly emotional reactions to employees starting their own business, to the sneaky ways non-solicitation clauses can still bite you, they dive deep into what’s driving this need for iron-clad control.
Hint: it’s not always about protecting the business—it might just be insecurity.
So, do non-competes actually make sense in today’s world?
Especially since over the summer we saw the Federal Trade Commission adopt a rule effectively banning worker post-termination non-competes, which was overruled just before its implementation by a TX federal court order that banned the FTC’s ban.
John and Kate debate whether businesses should be less worried about losing employees and more concerned about why they feel the need to lock them down in the first place.
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We’re back with drinks in hand, gearing up for a new season of Whiskey Fridays. This season, we’re tackling all the big stuff—starting with non-compete agreements. They’ve been in the courts and in the news, and John’s got a new take on them.
We’ll also be focusing on money—but not in the typical way. Think radical approaches to profit, ethical compensation, and a primer on investor relationships. Kate’s got some fascinating interviews lined up, including with anticapitalist wealth management firm Chordata Capital and with Jessica Norwood, where they explore the question: What would it look like if the economy loved Black people?
So, grab a drink and get ready for real talk, great interviews, and plenty of laughs. Whiskey Fridays is back!
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Featuring Music by Billy Dufala:
Whiskey Friday's is on Summer Break! But we're recording new episodes for the fall and have a tiny sneak peak on what we're working on.
Mostly: Money.
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So you want to offer your team members paid family and medical leave? Yeah, good luck with that.
The few government programs that exist to help businesses support paid leave policies often don’t apply to small businesses. So, owners who want to provide paid leave are left to cobble together solutions and policies of their own.
Kate discusses the historical context of paid leave in the US, including the lack of national policies compared to other countries and the challenges businesses face in providing adequate leave. She examines three critical components of creating a paid leave policy: profitability, system documentation, and policy consistency.
Offering paid leave isn’t easy, but it’s a huge opportunity for businesses to rise to their potential as systems of care.
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If your relationship status with your business is “it’s complicated,” then it’s time for some clean-up.
You and your business need some space. And that space? John calls it legal hygiene. And if you take the time, you and your business can enjoy a long and fruitful relationship.
John shares three real-life examples of legal hygiene gone wrong, from newbies making mistakes to people who really should have known better. Kate adds her two cents on why you need to respect your containers and why, in the Venn diagram of your business, you should only overlap when you intend to.
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Today is a bonus episode featuring Kate, Charlie Gilkey, and Tara McMullin discussing the creator economy. It originally aired in the What Works feed—the first part of this conversation is here.
"How do I want to live?" Philosopher Rahel Jaeggi says this question is bound up in the concept of alienation. Our disconnection and dissatisfaction keep us from answering that question—but they also keep us from asking it in the first place.
So in this episode, Kate, Charlie, and I ask that question—and five more. We examine how work in the creator economy can reinforce competition and individualism when what we really need is solidarity and collective action. If you're curious what you can do to join with others for your own success and theirs, this episode has some ideas.
Footnotes:
As always, find an essay version of today's episode at whatworks.fyi
Today is a bonus episode featuring Kate, Charlie Gilkey, and Tara McMullin discussing the creator economy. It originally aired in the What Works feed. Part 2 of this conversation will be available on Thursday!
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It seems the creator economy is booming. Or is it?
And what even is the creator economy??
Platforms like Instagram, YouTube, and TechTalk are quite happy to advertise the ways they support creators with features and advice. Their aspirational creator hubs give the distinct impression that becoming a creator is akin to getting paid to be yourself.
But that said, when Kate told Tara that she doesn’t think the creator economy should exist but that she couldn’t put that in writing, Tara told her she was wrong—about not being able to put that in writing. Turns out, Kate and Tara's mutual friend Charlie Gilkey had told her the same thing. So Tara arranged a meeting of the minds.
Today's episode is Part 1 of 2 of that conversation. We get into who a creator is, how the creator economy really works, why we value what we value, and how platforms distort the market for our creative work.
You can also read an essay version of this episode here.
Footnotes:
If an organization is progressive and cares about its staff, then workers don’t need a union, right?
Employee survey says: Nope.
Unions are taking off in all sorts of mission-driven non-profits and small businesses.
Management can work with the union or against it, stagnate in defensive mode, or ultimately see it as an opportunity for the organization to get stronger.
That’s what Melissa Weiler Gerber, President and CEO of Access Matters, found out when some of her nonprofit’s employees announced their intent to unionize.
Melissa walks John through the unionization process—from the first announcement to the signed collective bargaining agreement. She shares how her thinking evolved and explains why it is important for leaders to be introspective rather than reactive so that they can approach each union request with curiosity and a solutions mindset.
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Featuring Music by Dan Matz:
Should you reward your employees with performance-based bonuses? Kate says…
No! The more equitable move is transparent profit distribution.
Kate explains why performance-based bonuses make a false connection between hard work and profit, can’t be accurately measured, and lack transparency. Her thesis is that profit distribution ties additional compensation to the collective success of a company. Everyone gets to enjoy a bit of what they create together.
Plus, she offers an inside look at how profit-sharing works at Wanderwell.
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Featuring Music by Billy Dufala:
Employees are critical to business growth and success. So, shouldn’t they get a piece of the pie?
Well…maybe. Offering employee equity is a process. You’ve got to consider the whats, whys, whos, and hows to ensure it’s the right move for your business (and your employees!).
Kate interviews John about the finer points of two employee equity models–partnership vs participation– and they get real nerdy about profit distribution, tax ramifications, and ownership dilution.
Plus, a special guest appearance by CPA extraordinaire John Sullivan, explaining why no pie is ever free.
Listen to the bonus addendum to this episode - BONUS Addendum to Episode 13
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Featuring Music by Dan Matz:
Once you give an employee equity, does that mean you’re partners for better…and worse?
In this bonus addendum to Episode 13 – Employee Equity: Sharing the Pie – John talks through all the glorious nerdy technical details around ensuring you can buy back shares from employees.
Go and listen to the full episode here - Episode 13 - Employee Equity: Sharing the Pie
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Money shit is hard, even on a good day.
So, what should you do when a client refuses to pay you, even after you have fulfilled your end of the agreement? You’ve done your part, but the client is refusing to pony up?
Kate and John use two real-life examples of service-based businesses to explore payment structure, well-drafted contracts, and what you can do to ensure you get paid.
Hint: It’s all about relationships.
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Featuring Music by Pete Angevine,