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

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.

The Remote Work Tribe Podcast: Tyler Hochman

In this episode of the Remote Work Tribe podcast, we chat with Tyler Hochman, AI Solutions Architect and founder at FORE Enterprise. We cover how AI has raised the baseline for software engineers, what separates average AI users from elite ones, how to build a culture of experimentation inside a company, and more. Episode timestamps: * How did Tyler get into AI, and what does FORE Enterprise do? (0:23) * The pivot from workplace turnover software to AI architecture firm. (2:23) * How AI has raised the productivity floor for software engineers. (5:14) * What separates a 60% AI user from a 90-95% one in engineering interviews. (7:23) * Hiring for non-engineering roles and how AI changes those job descriptions. (10:23) * Big data synthesis as the differentiator for elite salespeople using AI. (13:14) * The most interesting AI application Tyler has built: parsing sports footage for scouting. (14:23) * How to set internal KPIs and performance reviews around AI usage. (16:23) * Using senior management to set baselines and weekly AI education for the team. (17:23) * How to keep those baselines from going stale as tools evolve rapidly. (18:23) * Building an experimentation culture and what that looks like day to day. (19:23) * Tyler's current obsession: image recognition and pixel quality with Gemini. (22:23) * Lightning round questions. (24:23) We hope you enjoy it! Links mentioned on the podcast: * foreenterprise.com * Theremoteworktribe.com * newsletter.theremotetribe.com * Jessicamalnik.com ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.