The Remote Work Tribe Podcast: How do you know when it's time to sell your business

The Remote Work Tribe Podcast: Rob Walling

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 [https://acast.com/privacy] for more information.

The Remote Work Tribe Podcast: Joe Casabona

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. 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 [matrix.streamlinedsolopreneur.com] * linkedin.com/in/jcasabona [linkedin.com/in/jcasabona] * Theremoteworktribe.com [http://theremoteworktribe.com/] * newsletter.theremotetribe.com [http://newsletter.theremotetribe.com/] * Jessicamalnik.com [http://jessicamalnik.com/] ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

The Remote Work Tribe Podcast: Anthony Pierri

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 [linkedin.com/in/anthonypierri] * Theremoteworktribe.com [http://theremoteworktribe.com/] * newsletter.theremotetribe.com [http://newsletter.theremotetribe.com/] * Jessicamalnik.com [http://jessicamalnik.com/] ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

The Remote Work Tribe Podcast: Kevan Lee and Shannon Deep

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 [http://aroundthebonfire.com] * Theremoteworktribe.com [http://theremoteworktribe.com/] * newsletter.theremotetribe.com [http://newsletter.theremotetribe.com/] * Jessicamalnik.com [http://jessicamalnik.com/] ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

The Remote Work Tribe Podcast: How do you know when it's time to sell your business

Most founders think about their exit too late. These six didn't. This episode pulls together first-hand soundbites from successful founders, including Jason Cohen, Laura Roeder, Carrie Kerpen, and Nick Gray on the things that actually matter when building a business that you might want to sell down the line including: documentation, exit timing, knowing your number, and why strategy isn't optional. --- In this episode: - What to do with money once you exit - Why documentation is an exit strategy, not just an ops thing - How far in advance to start planning your exit - Why some of the "worst" assets make the best acquisitions - How to know when you're ready to sell before you're desperate - Why skipping strategy kills your valuation Podcast links * Nick Gray’s [https://open.spotify.com/episode/1gK60BxFpVO3F5HOaDr82b?si=4c69aa4295de4c77] Episode * Laura Roeder’s [https://open.spotify.com/episode/7sgExhZJslrIKYWdAavLZv?si=0e93ae2095d64ac9] Episode * Dom Wells [https://open.spotify.com/episode/1vAzkmNt7f9OocjjpWGmYI?si=73841342b30d4929]’ Episode * Carrie Kerpen’s [https://open.spotify.com/episode/5zGQeHn1P77ZPx9aBq0FZo?si=e1f5cc3b00e54873] Episode * Jason Cohen’s [https://open.spotify.com/episode/1f80iHzUSrszE1pm4LEEhi?si=7c48889d7e704fae] Episode * Theremoteworktribe.com [http://theremoteworktribe.com/] * newsletter.theremotetribe.com [http://newsletter.theremotetribe.com/] * Jessicamalnik.com [http://jessicamalnik.com/] ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.