The Remote Work Tribe Podcast

In this episode of the Remote Work Tribe podcast, we talk with Gerard Holland, Founder and Executive Director at Talent Match Africa. We discuss implementing AI with a quality-focused mindset and culture, nurturing a culture of growth and learning, the impact of having an office, and more.

Episode timestamps:

• Most important thing Gerard is working on. (0:25)
• How he uses AI in his workflows as a founder. (0:58)
• Details on his current AI workflow. (1:49)
• Agents he is running that help him save time. 3:46)
• Has he been able to scale his skills using Claude as a traditional Excel power user? (6:02)
• AI and its impact on hiring. (7:12)
• How to ensure the person you’re hiring has an AI native mindset. (9:29)
• How to recognize whether or not the person actually has expertise when it comes to using AI in their workflow. (13:01)
• Gerard’s personal AI stack. (16:46)
• How does he think about AI governance and using AI for the team? (19:44)
• Building an AI-first culture. (21:54)
• Hybrid culture and its impact on AI implementation and workflows. (23:55)
• Measuring performance using AI metrics. (26:10)
• How has AI adoption evolved? (27:17)
• Ensuring AI quality output vs. AI slop. (30:08)
• A lot of slop comes from individuals without a lot of experience. The impact of in-person work on improving their work. (32:44)
• Remote vs. Hybrid? What is really at play when it comes to office spaces? (37:55)
• The balance between online and offline culture. (42:00)
• Lightning round questions. (44:14)

We hope you enjoy it!

Podcast links

• linkedin.com/in/gerardholland
• talentmatchafrica.com
• Theremoteworktribe.com
• newsletter.theremotetribe.com
• Jessicamalnik.com

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we talk with Rhys Williams, Founder and Managing Partner at Domestique. We discuss how to experiment with AI, balancing AI adoption between those who are excited and those who are hesitant to use it, implementing an AI council to figure out the rules of the game, and more. 

Episode timestamps:

• When did Rhys start experimenting with AI? (0:32)
• When did he start taking AI more seriously? (3:27)
• Balancing AI adoption between hesitant and power users. (5:54)
• Is he seeing a lot of pushback or excitement to implement AI? (8:25)
• How much of AI being poorly implemented occurs due to lack of AI policies and systems? (11:24)
• Context switching and how we can evolve at work to use AI in our workflows. (16:19)
• The paradox of AI models improving themselves. (20:14)
• AI costs and how to better monitor token cost and AI usage. (23:46)
• The importance of having a centralized AI council. (28:07)
• Ensuring AI adoption in a way that serves the organization. (29:19)
• How does Rhys think his AI use will evolve at a personal and org level? (31:32)
• Lightning round questions. (33:07)

We hope you enjoy it!

Podcast links

• domestique.info
• linkedin.com/in/rhys-williams-24563617
• Theremoteworktribe.com
• newsletter.theremotetribe.com
• Jessicamalnik.com

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we talk with Laura Weaving, CEO of Perform Platform. She shares her journey in leadership consulting, lessons from her father, profiling done well, and some of the most common flaws CEOs tend to have.

Episode timestamps:

• Most exciting thing Laura is working on today. (0:24)
• How she got started in leadership consulting. (1:00)
• Growing up with a father who works in leadership consulting. (2:27)
• Other leadership lessons she learned from her father. (4:24)
• How to do profiling well. (6:05)
• Tactics to identify leaders and motivation styles. (8:13)
• Surprising leadership lessons she’s learned running her team. (12:05)
• What is the most common flaw leaders have? (15:47)
• Lightning round questions. (19:04)

We hope you enjoy it!

Podcast links

• instagram.com/iamlauraelizabethw
• linkedin.com/in/lauraweavingperform
• Theremoteworktribe.com
• newsletter.theremotetribe.com
• Jessicamalnik.com

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we talk with Mikey Mioduski, founder of GhostRanch Communications. We discuss the journey of running an agency and stepping out of the day-to-day operations, the power of a CEO and COO combo to run your business, how to sync once you’re out of operations, and more.

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Episode timestamps:

• High-level trajectory of focusing on the business instead of working on it. (1:00)
• Stepping out of the day-to-day operations. (6:06)
• How did he prepare to step out of the business for his sabbatical? (11:32)
• What was surprising about moving away from the daily operations? (13:25)
• The process to transition employees into leadership roles and stepping out of the business. (15:25)
• Why did the combo of promoting employees to CEO and COO work for his company? (19:53)
• Internal perceptions and reactions once he stepped out of the business. (22:17)
• How often does he sync with his leadership team? What does communication look like as an owner? (25:56)
• Making sure hierarchies align with ownership and communication. (28:50)
• Storycamp and how he decided to step out of GhostRanch and double down in a new venture. (30:25)
• Lightning round questions. (33:47)

We hope you enjoy it!

Podcast links

• storycamp.com
• linkedin.com/in/mioduskidesign
• Theremoteworktribe.com
• newsletter.theremotetribe.com
• Jessicamalnik.com

Hosted on Acast. See acast.com/privacy for more information.

Remote work unbundled the office. The desk, the meetings, the hallway chats, the culture: they all went their separate ways. In this episode, Jessica Malnik strings together conversations with past guests to trace where each piece landed, and why retreats picked up so much of what the office dropped.

If you want to understand what remote work did to office culture, start here.

Related assets

• jessicamalnik.com/resources/remote-work-retreat-industry
• github.com/jessicamalnik/remote-work-retreat-industry

Episodes we revisit:

• Stella Garber. Offsites build trust and psychological safety. Remote does not mean rejecting face time. Full episode here. 
• William Chia. Remote versus in-person is a false dichotomy. Effective remote work can still require face-to-face time. Full episode here.
• Meryl Johnston. Remote-first teams can value face-to-face relationships. Retreat organizers should handle logistics while leaders shape goals and culture. Full episode here.
• Jared Kleinert. Offsites can build culture or become a box-checking perk. Gathering design should start with goals, environment, facilitation, and invitees. Full episode here.
• Jesse Schoberg. The value of gathering comes from the extra moments around work and the shift in headspace that a different physical context creates. Full episode here.
• Branca Ballot. Small in-person groups can gather around one difficult customer problem for deeper exploration than digital settings allow. Full episode here.
• Scott Brills. Prospective retreat operators should run the trip first with forgiving participants before selling it to strangers. Full episode here. 
• Amar Ghose. Off-topic water-cooler exchanges and team retreats support informal connection that remote work strips away. Full episode here. 
• Barrett Brooks. Creating space and rest helps people return to distributed work without feeling overwhelmed. Full episode here.
• John Yarbrough. Remote work created time for walks, cooking, and more intentional self-care. Full episode here. 

We hope you enjoy it!

Additional Podcast Links

• Theremoteworktribe.com
• newsletter.theremotetribe.com
• Jessicamalnik.com

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we talk with Noel Andrews, owner and CEO at JobRack. We discuss the disruption happening in the job market with AI, how to optimize for taste and judgement, the importance of referrals and how to make them work for any service business, media and its impact in perception and mental health, antifragile roles for the future, and more. 

Episode timestamps:

• What is happening to hiring with AI in the picture? (0:30)
• How to think about quality when it comes to hiring with AI.  (5:02)
• Optimizing for intuition and taste when hiring. (6:55)
• Tools his team has built with AI. (9:35)
• What magical tool would solve a lot of problems in his field? (11:46)
• Building tools and finding out what is outdated. (14:04)
• Should you build your own CRM?. (16:08)
• Referrals and how to build an engine around them. (18:25)
• Asking for referrals the right way. (21:16)
• How to interact with those reluctant to recommend your business. (24:16)
• AI and referrals. (26:53)
• Referrals beyond the transactional nature of it. (29:23)
• How often does Noel send referral emails? (33:32)
• AI as a cover for layoffs. (36:40)
• The role of the media in understanding AI. (41:33)
• What are some antifragile roles Noel thinks will be safe in the future? (45:13)
• Entry-level disruption with AI and its advantages today. (47:44)

We hope you enjoy it!

Podcast links

• The Remote Work Tribe Podcast: Noel Andrews
• JobRack - Referral Programme
• Theremoteworktribe.com
• newsletter.theremotetribe.com
• Jessicamalnik.com

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we talk with Rob Walling, co-founder of TinySeed and MicroConf and host of Startups for the Rest of Us, and one of the most influential voices in bootstrapped SaaS.

We explore what actually matters in a world increasingly shaped by AI, including why taste and judgment may become more valuable than ever, how founders can develop product intuition, why mentorship and battle scars still matter, and what AI is truly changing across software, marketing, and entrepreneurship.

Rob also shares lessons from building and scaling SaaS companies, how he thinks about attention and audience building in 2026, and why bringing more of yourself into your work may be one of the most durable competitive advantages you have.

If you're a founder, creator, marketer, or builder trying to figure out where AI fits into your work without losing the human skills that matter most, this episode is packed with practical insights and thoughtful perspectives.

Notable questions covered:

Jessica: "How do people develop taste now that pretty much you're almost expected to use AI first?"

Jessica: "How do you get those battle scars if all you've known is AI?"

Jessica: "How do you move forward fast enough to build momentum and not constantly start and stop?"

Jessica: How do you know what you should be building when anything can be built faster than ever?"

Episode timestamps

• Why Rob started writing again after years focused on podcasting and video. (0:25)
• Using AI to transform podcast transcripts into newsletter content. (2:02)
• Why taste matters more than ever in the age of AI. (6:07)
• Can future generations develop taste if AI creates most content? (8:24)
• The future of attention, distribution, and human-created content. (11:45)
• Why bringing more of yourself into your work builds stronger audience connections. (13:18)
• The future of SEO, authority, and search in an AI-driven world. (15:19)
• What AI is actually killing and what is merely changing. (18:05)
• Why entry-level workers face a different challenge than previous generations. (20:18)
• Mentorship, battle scars, and learning skills in the AI era. (21:00)
• The story of Rob's son spending $210 on Meta ads to learn marketing. (23:40)
• Founder coping mechanisms, anxiety, and managing uncertainty. (26:08)
• Why every founder strength eventually becomes a weakness. (27:50)
• Childhood experiences, confidence, and entrepreneurial risk-taking. (30:25)
• How founders build momentum despite anxiety and self-doubt. (32:30)
• The power of making a series of ever-increasing bets. (33:15)
• Whether the Stair Step Method still works in the AI era. (35:00)
• Why so many founders build the wrong SaaS products first. (37:25)
• How to decide what features to build when AI makes development easier. (39:00)
• Product intuition, product-market fit, and what AI still can't do well. (39:50)
• How founders can develop stronger product judgment. (44:05)
• Lightning round questions. (45:15)
• The surprising impact of podcasting over 16 years. (46:20)
• Why YouTube changed how people recognize Rob in public. (48:05)

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we talk with Joe Casabona, a solopreneur business coach. We discuss the importance of creating systems, implementing AI in ways that augment your capacities rather than replace them, delegating to VAs and/or AI tools, and more.

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Episode timestamps:

• Joe’s overall perception of AI in 2026. (0:50)
• Focus work vs. Process work and how AI fits into it. (3:15)
• The importance of designing and thinking in systems. (6:12)
• Limits of AI in organizing processes. (8:23)
• Thinking of the system first as a founder before delegating. (10:29)
• How to get someone to think in systems. (14:42)
• AI implementation vs. VA work. (17:42)
• Joe’s approach to AI in his overall business. (20:21)
• Non-negotiables when working with contractors. (23:00)
• Preproduction processes and AI. (25:28)
• Automation vs. using AI for ideation. (27:58)
• AI in the production process for Joe’s podcasts. (30:38)
• Appropriately using AI for focus work. (32:26)
• The argument for the end of AI price subsidies. (36:18)
• Visions of the future of AI pricing models. (41:49)
• Lightning round questions. (43:42)

We hope you enjoy it!

Podcast links

• matrix.streamlinedsolopreneur.com
• linkedin.com/in/jcasabona
• Theremoteworktribe.com
• newsletter.theremotetribe.com
• Jessicamalnik.com

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we talk with Anthony Pierri, co-founder at Fletch. We discuss the importance of doubling down on quality and depth for marketing efforts, how to build a team and use AI effectively, the importance of productizing your business model, and more.

Episode timestamps:

• How has Anthony grown his business through LinkedIn, and what makes his approach unique? (1:17)
• What is Anthony thinking about when it comes to creating content that is unique or interesting, or something that only he or Fletch can say? (8:24)
• What is keeping Anthony up at night right now when it comes to the business? (25:41)
• Does Anthony worry about investing time in getting his core team to promote the brand, and then having them eventually leave after all that investment? (31:01)
• Is Anthony worried about giving away so much of his IP and intel to freelancers who are working under the Fletch umbrella but are ultimately independent? (37:04)
• Does Anthony ever worry that given his productized model with workshops and homepage wireframes, AI will eventually undercut him and force him to lower prices or evolve? (45:28)
• Where does Anthony see himself in 10 years? (53:23)

We hope you enjoy it!

Podcast links

• linkedin.com/in/anthonypierri
• Theremoteworktribe.com
• newsletter.theremotetribe.com
• Jessicamalnik.com

Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we talk with Kevan and Shannon, co-founders at Bonfire. We discuss the rollercoaster of starting an agency, finding the best way to utilize their time, management styles, and how to ensure clients receive excellent deliverables. We also chat about the importance of betting on yourself, finding the confidence to do hard things, and evolving from in-house to founder.

Episode timestamps:

• How did they come up with the idea for Bonfire? (0:40).
• How did they know it was the right time to start their own thing? (4:00).
• Mindset shifts from working in-house to running a business. (6:39)
• How did they know they wanted to team up instead of going solo? (9:12)
• Accountability, structure, responsibilities, and more of starting a company. (12:51)
• Alignment to make sure the best work gets done. (17:36)
• Team structure and leadership between two cofounders. (21:07)
• Knowing what they know now, what would they have done differently? (25:28)
• Managing people: Giving advice vs. internalizing advice - Shannon. (27:37)
• Managing people: Giving advice vs. internalizing advice - Kevan. (31:54)
• What did they learn in-house that has helped them be better founders? (35:27)
• Pressure working for yourself vs. working for someone else. (38:29)
• What message would they tell themselves 10 years in the past? (40:55)

We hope you enjoy it!

Podcast links

• aroundthebonfire.com
• Theremoteworktribe.com
• newsletter.theremotetribe.com
• Jessicamalnik.com

Hosted on Acast. See acast.com/privacy for more information.