Caffeine Conversations

By David Sherry

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Learn how your favorite creators are building a brand and community around who they are. This podcast is hosted David Sherry, Founder of Death to Stock and Community organizer of Jacuzzi Club.

Episode Date
3 reminders: State, Story, Strategy
Aug 31, 2022
Struggling to hit your goals? This might be why
Aug 30, 2022
I'm playing too small
Aug 25, 2022
The 4x4 that matters most in life: Happy, Active, or Down/Lazy?
Aug 23, 2022
Take your TOP problem, and focus on it. (To remove overwhelm)
Aug 22, 2022
How do I come up with creative ideas? I sit and listen.
Aug 18, 2022
What can you do if you're feeling "meh" today?
Aug 17, 2022
Kari – An Interview with a Face Yoga Coach
I've started interviewing niche coaches who are doing interesting work that are for hire. Today I interview a "Face Yoga" coach who gained popularity through TikTok. We talk about her process with clients and this emerging coaching space. You can check out her work here: and find her on Youtube/TikTok
Jul 17, 2021
James Rores – Learn to Feel Comfortable Selling

In this episode, I speak with James Rores about learning Sales. James coaching teams and leaders to develop proven strategies for their sales processes, but does so with the mindset of a coach and leader rather than a huckster. 

I really enjoyed this conversation and if you're looking to learn more, you can find more about his company and their processes here:

Mar 14, 2021
Andy Didorosi – Collaborative "Email" Marketing (Basecamp)

In this episode, I talk with Basecamp and Hey email's head of Marketing, Andy Didorosi about a whole slew of topics related to marketing in a collaborative and unique new way. We focus this conversation on their recent "Dumpster Fire" email project 

Find Andy on Twitter:

Mar 08, 2021
Will Mannon – Surfing the Internet For Education and Ideas (BASB)

Will Mannon is the course manager for two fast-growing online, cohort-based courses, "Building a Second Brain" and "Writes of Passage". On this episode, we discuss the future of online learning, the opportunities Will see's for people diving into the creator economy, and some of Will's favorite quotes and ways of looking at the world.

You can follow Will on Twitter or check out his blog here!

Dec 04, 2020
Mac Reddin – Community Metrics that Matter (Commsor)

Mac Reddin is the founder of Commsor, which is a tool that puts all of your community data into one place. Mac also runs a Slack community for community leaders called Community Club. In this episode, we spoke about the rapid growth of Mac's company, how it feels when everything starts to take off, and Mac's perspective on the community metrics that matter.

You can check out Mac at...

Dec 02, 2020
Adam Jackson – User Owned Marketplaces (Braintrust)

Adam Jackson is the Founder of Braintrust. Braintrust is a user-owned, blockchain-based freelancer marketplace. What fascinated me about this conversation is that it sheds light on what the future could look like for user-owned networks. 

And, how the governance built by the Braintrust team is built that allows aligned incentives between investors, freelancers, and companies they serve. This concept is part of a larger shift to how the creator economy will function and how freelancers can create value while retaining power in the networks that they create for.

You can check out Braintrust here which is in open Beta until early next year:

Nov 20, 2020
Maria Falbo – Big Brand Collabs While Keeping Your Soul (Copson)

Maria Falbo is the founder of Copson London, a skate and spiritual brand that collaborates with some of the world's best brands, like Vans and New Balance. Now she's building a community around her soulful search for creative work that brings a spiritual essence to the brands that they work with. 

You can view some her collabs here as well as the video referenced in the podcast.

You can follow Maria on Instagram here:

Nov 17, 2020
Nick deWilde – Balancing Side Projects with Full Time Work

Nick deWilde is a Product Marketer at Guild, a fast-growing startup that helps companies transform their workforces through education. He also publishes a newsletter called the Jungle Gym which based on insights around career growth and working smarter.  

What caught my attention about Nicks' work was his posts on career journey:

As well as creators and communities:

You can also find Nick on Twitter:

Oct 31, 2020
Robert Fritz – The Path of Least Resistance (Author)

Robert Frtiz is an author, composer, and filmmaker who is known for his work dissecting the creative process via his theory of "Structural Dynamics."

In this episode, I speak with Robert about the creative process and his years of studying and speaking on this topic. This episode is different in that it's less about brand/creator strategy but more about the individual process for being a creator. 

I've loved his books, most notably "The Path of Least Resistance" which covers his expertise in depth.

Oct 24, 2020
Li Jin – The Software That Empowers Community Leaders (Atelier)

Li Jin is the founder of Atelier, an early-stage firm investing in the passion economy. She also writes a newsletter about passion economy platforms and consumer startups on Substack. Prior to Atelier, Li was an investing partner at Andreessen Horowitz.

In this podcast, Li joins me as a co-host to discuss a co-written blog post we wrote as an open letter for community leaders. 
You can read it here:

Oct 17, 2020
Ana Andjelic – The Business of Aspiration (Sociology of Business)

Ana Andjelic is a strategy executive, author of the new book "The Business of Aspiration" who specializes in building brand-driven modern businesses. Ana earned her doctorate in sociology and worked at the world's top brands – Like Puma, Topshop, Tom Ford, etc.

She is a widely read columnist, speaker and advisor.

This conversation was hosted via Jacuzzi Club, so the format is a bit different. You'll hear questions from other members on the show later in the episode, so don't mind that. Also sorry for any slight Zoom lags :) 

Check out her newsletter:
Or her new book:

Oct 08, 2020
Zoe Scaman – The Business Models of the Creator Economy (Bodacious)

Zoe Scaman is a London-based strategist who's worked with celebrities, athletes, and brands like Adidas, Droga5, and Universal McCann.

Our conversation covers how brands and creators are using new models for product development and monetization.

Check out Zoe's writing here:
Or follow her on Twitter:

Or, the talk that got me introduced to her work:

Oct 01, 2020
Andrew Guttormsen – Tailoring the Community Experience (Circle)

Andrew Guttormsen is the Co-Founder of, a flexible community space for teachers and businesses. In this episode, we discuss how Circle is tailored to fit some of the core problems around building community. We get into why certain features exist, and I think that this will help shed light on many ideas around community building that you may have not considered. 

Sep 24, 2020
Dan Hunt – Community as a Publishing Service (Compound)

Dan Hunt is the creator of Compound, a community for aspiring writers and publishers looking for help in their process. Dan has a really diverse and unique background of building products and companies, and so I was really interested to hear about his perspective on community building. To Dan, the community should help you accomplish something, which is exactly what he's built with his writers group that helps you edit, research, and develop your writing to a higher standard. 

Sep 17, 2020
Khe Hy – The Magic of 10k Work (Radreads)

Khe Hy is the writer of RadReads. He's also a Notion Pro, launching his new course Supercharge your Productivity with Notion (linked below). What I love about Khe is his blend of focus and productivity work with his care for community and helping people transform. In this show, we talk about how he pursues his own path when creating courses, and the difference between "$10 and $10,000 work." 


Link to his Notion course:

Sep 10, 2020
Anna Gát – Building a Global Intellectual Community (Interintellect)

Anna Gát is the creator and organizer of the InterIntellect, a global forum for intellectual discussions and remote salons. We discuss how she got this global movement started as well as how she followed her own path launching and building this community.

Sep 03, 2020
Adrian Alfieri – Personal Wellness and Community (The Proof)

Adrian Alfieri is an investor and the creator of The Proof, a collection of interviews with top founders about their wellness habits and attitudes towards self-care. Adrian is one of the best networkers I know (without trying) and we discuss how he percieves building community around his interest in wellness.

Aug 28, 2020
Ben Tossell: Quickly Shipping Side Projects (Makerpad)

Ben Tossell is the founder of – a no-code community for learning to build and ship projects without writing any code. Ben turned his side project into a full time, funded business and community at the heart of this industry. Side-note, I also work closely with Ben and his team.

Aug 24, 2020
Kaleigh Moore: Freelancer Networks (Copywriter)

Kaleigh Moore is a freelance copywriter, course instructor, podcaster and blogger for top companies in the Fortune 500 and startups. She's also the student, turned instructor of the Creative Class, which is a Freelancer course co-created with Paul Jarvis.

Her site:
Creative Class:

Aug 23, 2020
Dan Shipper: Following your Career Thread (Superorganizers)

Dan Shipper is the writer of Superorganizers on Substack as part of the Everything Bundle.

Learn more about the host:

Aug 22, 2020
[Full Conversation] Navigating Life with Ease with Kirat Randhawa

Learn more about Kirat here:

May 21, 2020
[Introduction] Kirat Randhawa, A Kind Rupture

Learn more about Kirat here:

May 19, 2020