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

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 linksmatrix.streamlinedsolopreneur.comlinkedin.com/in/jcasabonaTheremoteworktribe.comnewsletter.theremotetribe.comJessicamalnik.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 linkslinkedin.com/in/anthonypierriTheremoteworktribe.comnewsletter.theremotetribe.comJessicamalnik.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 linksaroundthebonfire.comTheremoteworktribe.comnewsletter.theremotetribe.comJessicamalnik.com Hosted on Acast. See acast.com/privacy for more information.

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 valuationPodcast linksNick Gray’s EpisodeLaura Roeder’s EpisodeDom Wells’ EpisodeCarrie Kerpen’s EpisodeJason Cohen’s EpisodeTheremoteworktribe.comnewsletter.theremotetribe.comJessicamalnik.com Hosted on Acast. See acast.com/privacy for more information.

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.comTheremoteworktribe.comnewsletter.theremotetribe.comJessicamalnik.com Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we chat with Sebastian, Producer at the Remote Work Tribe. We discuss how AI amplifies your existing skills and taste, the importance of developing judgment in your domain, how self-imposed limits can sharpen your creativity, and what digital work might look like in 2030.Episode timestamps:What does it mean to have good taste, and can anyone develop it? (1:00)AI as an amplifier: why expertise determines whether AI helps or hurts you. (1:30)Combining multiple domains to create work only you can make. (10:23)The shift from doing to curating, and why creativity is the new productivity. (12:28)Outputs vs. outcomes: how to communicate your work in a results-driven world. (14:18)How moving faster with AI frees up time to develop your taste. (18:30)Self-imposed limits as a tool for creativity and better thinking. (20:50)Charged content, Cal Newport, and protecting your ability to think critically. (28:17)What does digital work look like in 2030? (29:59)Why millennials may have a unique edge in the AI era. (34:14)The challenges Gen Z faces entering the workforce right now. (35:46)We hope you enjoy it!Links mentioned on the podcast:Article on GenZ and work being more depressing than unemployment.Theremoteworktribe.comnewsletter.theremotetribe.comJessicamalnik.com Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we chat with Nick Gray, founder of Museum Hack and author of The Two Hour Cocktail Party. We discuss why founders should build their personal brand, how to start sharing online when you have no idea what to post, Nick's approach to asset allocation and investing, and the $50,000 real estate mistake he learned the hard way.Episode timestamps:How did Nick get into living his life "out loud"? (0:55)Why founders need to build a personal brand. (3:23)The biggest reason founders don't start posting online. (6:29)A simple trick to help anyone start sharing on social media. (7:17)What is asset allocation and why should founders care? (14:09)Nick's investing approach and why he's 85% in stocks. (16:08)The best books and resources for beginner investors. (19:19)The $50,000 real estate deal that went sideways. (22:28)Should founders go all in on the business or diversify early? (25:55)Lightning round questions. (31:11)We hope you enjoy it!Links mentioned on the podcast:The Remote Work Tribe Podcast: Nick GrayTri Peak Holdings: Nick Gray's Family OfficePersonalWebsites.org: Discover Personal WebsitesNick Gray's PersonalWebsites.netPatron View: NYC Donor DatabaseNick Gray: The Personal Home Page of Nick GrayThe 2-Hour Cocktail Party BookPatron View Museum Donor Leaderboardstheremoteworktribe.comnewsletter.theremotetribe.comjessicamalnik.com Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we chat with Seth Nagle, Founder at LZC Marketing. We discuss the importance of betting on yourself, how to set up systems for growth and with purpose, trends and tools that are changing the landscape, and more. Episode timestamps:When did he know he needed to create an Agency? (0:47).How did he know it was the right time to bet on himself? (2:24)The importance of doing what’s unscalable, even if underpaid. (5:45)Parameters to avoid going down rabbit holes that don’t serve a purpose. (9:42)Setting up time, both being in the weeds and running the agency. (12:05)Tools or trends Seth has noticed will become important in the future. (14:31)How to make sure systems are in place to run a business. (17:51)  How often do people use a tool or feature as a band-aid for a bigger problem? (22:39)Is there a tool, tactic, or tech that will age poorly? (25:28)The balance between polished work vs. AI accelerated work. (28:26)Lightning round questions. (31:14) We hope you enjoy it!Links mentioned on the podcast:linkedin.com/in/seth-nagleseth@lzcmarketing.comTheremoteworktribe.comnewsletter.theremotetribe.comJessicamalnik.com Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we chat with Greg Osuri, Founder at Akash Network. We discuss the importance of radical transparency when running a company, lessons from developing products with a scrappy mentality, the importance of brand for your business, and more.  Episode timestamps:How did Greg get into his field of work? (0:51).Transparency in running a company and Why It Matters. (6:53)Radical transparency and its impact on onboarding. (12:18)Is access to transparent information a potential danger to the business? (15:20)What would Greg told himself 10 years ago, knowing what he knows now? (18:16)Thoughts on the lean startup method and the problem with undervaluing brand. (21:48)Scrapiness vs. quality when creating products. (24:59)  Lightning round questions. (26:33) We hope you enjoy it!Links mentioned on the podcast:x.com/gregosuriTheremoteworktribe.comnewsletter.theremotetribe.comJessicamalnik.com Hosted on Acast. See acast.com/privacy for more information.

In this episode of the Remote Work Tribe podcast, we chat with Liz Joly, Marketing Lead at Focus Lab. We discuss using AI systems for brand guidelines, distribution, and differentiation in a saturated, noisy environment, encouraging authenticity, and overcoming the cringe factor, among other topics.  Episode timestamps:One of the most exciting things Liz is working on these days. (0:35).Her take on AI. (1:24)Examples of how Liz and her team use AI. (2:02)What are brand guidelines? (3:51)Brand guidelines as an AI engine. (5:52)Distribution and differentiation in an AI-saturated landscape. (9:21)Distribution that breaks through the noise. (10:32)Authenticity from a company account perspective. (11:42)  How to encourage authenticity as a company and for individual employees? (12:48) Sharing valuable content vs. oversharing. (14:38)Cringe mountain and how to get past the fear of posting. (16:24)Lightning round questions. (18:15)We hope you enjoy it!Links mentioned on the podcast:linkedin.com/in/lizjolyTheremoteworktribe.comnewsletter.theremotetribe.comJessicamalnik.com Hosted on Acast. See acast.com/privacy for more information.