Episodes

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 Sig...

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 y...

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 ...

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 prioriti...

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...

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 L...

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 prof...

Ever wonder why some companies rake in massive profits while their employees get next to nothing? Meanwhile, other businesses spoil their teams with perks and paychecks, but the owner’s left questioning why they even bothered starting the business. In this episode John Gerber and Kate Tyson dive into the realities of profit distribution, where being the world's best boss can leave you flat broke – and spoiler: that’s not exactly a winning strategy. They also throw a bone to management guru Pet...

In this episode, 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 ...

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 f...

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. 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

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 businesse...

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...

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—an...

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! *** 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 impressio...

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 nonpro...

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 ...

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 ap...

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 Resources: Breaking Up is Hard to Do: Navigating Business Divorce Learn more about Kate Tyson: Wanderwell Connect on LinkedIn Sign u...

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. Learn more about Kate Tyson: Wanderwell Connect on LinkedIn Sign up for Kate’...

“I want us to fix the plane while we fly it.” Charlie Gilkey believes that dominant power structures need reforming – that we can change the way we relate to each other in our teams and at work. Kate and Charlie get into how cultural change is a long-term play and why better team habits are a critical component of the process. Charlie is the CEO of Productive Flourishing, a bestselling author, advisor, podcaster, and speaker. His latest book is Team Habits. Learn more about Charlie Gilkey: Pr...

How do we build worlds of interdependence, regeneration, and care? Sarah Ryhanen, founder of Saipua and Worlds End School of Thought, Agriculture, and Craft joins Kate to talk about dreaming, and most importantly, doing the work of building new worlds when the ones we exist in no longer serve us. Learn more about Sarah Ryhanen: Saipua Worlds End School of Thought, Agriculture and Craft Instagram: @saipua Featured Music by Billy Dufala: Instagram: @bdufala Thinkers and Books mentioned: Donna Ha...

Kate digs into the language of employment and teases out a shift she’s seeing that reimagines the employer-employee relationship. 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

The rules of how we interact with restaurants and the service industry at large are changing. But not without significant confusion, pushback, and sometimes outright belligerence. The restaurant industry as we know it is fundamentally broken and inequitable, a fact made all too clear during the pandemic when restaurant and service workers were hailed as essential, while simultaneously being chronically underpaid and overworked. Jenny Zavala, chef-owner of Philly’s Juana Tamale, joins Kate to d...