Podcast
Whiskey Fridays
Hosted by Kate Tyson And John Gerber · EN
Real talk at the heart of creative entrepreneurship with Kate Tyson and John Gerber.
Kate and John, longtime small business advisors, drink whiskey while dishing hard-won wisdom for entrepreneurs and leaders. We also publish "Boss Talks" episodes: interviews with leaders on new possibilities in business and economics and are possibly the only business podcast out there to feature special musical guests.
10episodes
Episodes
Newest firstAll episodes
Ep26 - Season Ender: Taking a Break
Dec 13, 202400:22:34Tap to summarizeNo 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:WanderwellConnect on LinkedInSign up for Kate’s NewsletterLearn more about John Gerber:UnlawyerInstagram: @un.lawyerConnect on LinkedInFeaturing Music by Billy Dufala:@bdufala
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Ep25 - Boss Talks: Taking an Extended Business Break with Nic Antoinette
Dec 6, 202400:41:54Tap to summarizeKate 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 SubstackLearn more about Kate Tyson:WanderwellConnect with Kate on LinkedInSign up for Kate’s NewsletterLearn more about John Gerber:UnlawyerInstagram: @un.lawyerConnect with John on LinkedInFeaturing Music by Pete Angevine:@pete_angevine
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Ep24 - Boss Talks: Designing Equitable Pay Structures with AORTA
Nov 29, 202400:34:56Tap to summarizeKate 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 & AORTANeily 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 WebsiteInstagram: @aortacoopConnect with Neily on LinkedInLearn more about Kate Tyson:WanderwellConnect on LinkedInSign up for Kate’s NewsletterLearn more about John Gerber:UnlawyerInstagram: @un.lawyerConnect on LinkedInFeaturing Music by Billy Dufala:@bdufala
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Ep23 - Boss Talks: Building an Anti-Racist and Reparative Economy with Jessica Norwood
Nov 22, 202400:55:42Tap to summarizeKate 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 NorwoodJessica Norwood's websiteRunwayConnect on LinkedInLearn more about Kate Tyson:WanderwellConnect on LinkedInSign up for Kate’s NewsletterLearn more about John Gerber:UnlawyerInstagram: @un.lawyerConnect on LinkedInFeaturing Music by Billy Dufala:@bdufala
Transcribe →Ep22 - Understanding Owner Compensation
Nov 15, 202400:28:36Tap to summarizeBusiness 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:WanderwellConnect on LinkedInSign up for Kate’s NewsletterKate’s Article: Getting PaidLearn more about John Gerber:UnlawyerInstagram: @un.lawyerConnect on LinkedInFeaturing Music by Billy Dufala:@bdufala
Transcribe →Ep21 - The Four Types of Business Investors
Nov 1, 202400:39:52Tap to summarizeEver 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:WanderwellConnect on LinkedInSign up for Kate’s NewsletterLearn more about John Gerber:UnlawyerInstagram: @un.lawyerConnect on LinkedInFeaturing Music by Billy Dufala:@bdufala
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Ep20 - Boss Talks: Making Money as an Anticapitalist with Bear Hebert
Oct 25, 202400:57:18Tap to summarizeKate 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 CoachesFreely: an anticapitalist guide to pricing your workLearn more about Kate Tyson:WanderwellConnect on LinkedInSign up for Kate’s NewsletterLearn more about John Gerber:UnlawyerInstagram: @un.lawyerConnect on LinkedInFeaturing Music by Billy Dufala:@bdufala
Transcribe →EP19 - The Purpose of Profit
Oct 18, 202400:26:24Tap to summarizeKate 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 DistributionLearn more about Kate Tyson:Wanderwell Zine ShopWanderwellConnect on LinkedInSign up for Kate’s NewsletterLearn more about John Gerber:UnlawyerInstagram: @un.lawyerConnect on LinkedInFeaturing Music by Billy Dufala:@bdufala
Transcribe →Ep18 ﹘ Non-Competes Make People Insane
Oct 11, 202400:31:47Tap to summarizeKate 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.Resources:Learn more about Kate Tyson:WanderwellConnect on LinkedInSign up for Kate’s NewsletterLearn more about John Gerber:UnlawyerInstagram: @un.lawyerConnect on LinkedInFeaturing Music by Billy Dufala:@bdufala
Transcribe →Season 2: What's Coming
Oct 4, 202400:05:54Tap to summarizeWe’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!Learn more about Kate Tyson:WanderwellConnect on LinkedInSign up for Kate’s NewsletterLearn more about John Gerber:UnlawyerInstagram: @un.lawyerConnect on LinkedInFeaturing Music by Billy Dufala:@bdufala
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