{"podcast":{"title":"21 Hats Podcast","slug":"21-hats-podcast-502638","podcast_index_feed_id":502638,"rss_url":"https://www.spreaker.com/show/4439758/episodes/feed","website_url":"https://www.spreaker.com/show/21-hats-podcast","image_url":"https://d3wo5wojvuv7l.cloudfront.net/t_rss_itunes_square_1400/images.spreaker.com/original/27e8ec21209a6c9a99a0f0963132b13e.jpg","author":"21 Hats","episode_count":568,"summary":"The 21 Hats Podcast presents an authentic weekly conversation with small business owners who are remarkably willing to share what’s working for them and what isn’t. Unlike many business podcasts, which tend to talk to highly successful entrepreneurs whose struggles are in the past, the 21 Hats Podcast features a rotating cast of business owners who are still very much in the trenches fighting the good fight. Every week, our regulars gather to talk about the kinds of important issues many owners won’t even discuss behind closed doors: whether their businesses are as profitable as they should be, whether they are willing to give up some control to an investor in order to grow faster, why they had to lay off employees, how they wound up with way too much inventory, why they don’t have a succession plan, and even why they are concerned about their own mental health. Visit 21hats.com to hear all of our podcast episodes, read episode transcripts, and learn more. The show is produced by Jess Thoubboron, founder of Blank Word.","last_synced_at":"2026-09-18T20:17:08.095147+00:00","page_url":"https://stenobird.com/podcast/21-hats-podcast-502638"},"episode":{"title":"Best of: Selling My Business Nearly Broke Me","slug":"best-of-selling-my-business-nearly-broke-me","published_at":"2026-08-25T09:03:28+00:00","page_url":"https://stenobird.com/podcast/21-hats-podcast-502638/best-of-selling-my-business-nearly-broke-me","show_page_url":"https://stenobird.com/podcast/21-hats-podcast-502638","url":"https://21hats.com/selling-my-business-nearly-broke-me/","audio_url":"https://api.spreaker.com/download/episode/74660464/21_hats_best_of_episode_8_25_26_stereo.mp3","summary":"This week, we revisit a conversation with Laura Zander that we first published last year, shortly after she and her husband Doug sold Jimmy Beans Wool, the business they had spent more than two decades building. Laura had been preparing to sell for years. She had kept the company’s books clean, built systems that could survive without her, and cultivated relationships with potential buyers. In other words, she had done many of the things owners are told they should do to prepare for an eventual exit. And still, when the right buyer finally came along, Laura says the process nearly broke her. There were 155 due diligence requests, endless rounds of legal negotiations, mountains of paperwork, and months when Laura and Doug were so consumed by the transaction that the business itself suffered. Meanwhile, life kept happening: a major website migration, tariffs, industry turmoil, family issues, and the constant fear that some unexpected development would cause the buyer to walk away. Even after the papers were signed, the work—and the stress—continued. Laura did ultimately get a deal she was happy with. But the more useful lesson may be what it took just to get there.","meta_description":"This week, we revisit a conversation with Laura Zander that we first published last year, shortly after she and her husband Doug sold Jimmy Beans Wool, th…","key_points":[],"chapters":[],"topics":[],"duration_seconds":3021,"processing_state":"not_requested","actions":[{"name":"request_transcript","method":"POST","url":"https://stenobird.com/v1/public/podcasts/21-hats-podcast-502638/episodes/best-of-selling-my-business-nearly-broke-me/transcription-requests","description":"Idempotently request low-priority transcript generation for this episode."},{"name":"read_markdown","method":"GET","url":"https://stenobird.com/podcast/21-hats-podcast-502638/best-of-selling-my-business-nearly-broke-me.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}