https://simplecast.com Gen X Executive is a first person account of what happens when someone who's spent decades building institutional grade financial systems walks into a 15-20 person startup - and has to figure out how to make it work anyway en Fri, 24 Apr 2026 14:39:07 +0000 Fri, 24 Apr 2026 14:56:46 +0000 https://gen-x-executive-second-act-at-a-tech-startup.simplecast.com https://image.simplecastcdn.com/images/96a10b54-3566-4ae1-87fd-fd8bff7bd182/ffa9e19f-7282-41b4-8151-8c3e1ea5cf10/3000x3000/gen-20x-20executive-20second-20act-20in-20motion.jpg?aid=rss_feed https://gen-x-executive-second-act-at-a-tech-startup.simplecast.com episodic Gen X Executive is a first person account of what happens when someone who's spent decades building institutional grade financial systems walks into a 15-20 person startup - and has to figure out how to make it work anyway Brad Firestone false https://feeds.simplecast.com/4CrbhIZ6 Brad Firestone booking@podgo.io 6f34080d-9075-49d1-850d-ff2031a41f72 Fri, 24 Apr 2026 14:39:07 +0000 booking@podgo.io (Brad Firestone) https://gen-x-executive-second-act-at-a-tech-startup.simplecast.com/episodes/gen-x-executive-the-stack-5vk_uc2l Gen X Executive: The Stack Brad Firestone 00:16:35 Episode 3: The Stack. Gen X Executive: Second Act at a Tech Startup with Bradley Firestone. Episode 3: The Stack. Gen X Executive: Second Act at a Tech Startup with Bradley Firestone. false full 5 35880d49-5136-44ff-86c8-40da79c09c16 Mon, 20 Apr 2026 18:26:22 +0000 booking@podgo.io (Brad Firestone) https://gen-x-executive-second-act-at-a-tech-startup.simplecast.com/episodes/day-two-million-dollar-term-sheet-crisis-1039kTcF Day Two Million Dollar Term Sheet Crisis Brad Firestone 00:18:54 Eighteen hours into a new job, a CEO drops a complex million-dollar preferred equity deal on your desk - no context, no preparation, just pure startup chaos. Welcome to week one at a fast-growing company where everything happens at once. Eighteen hours into a new job, a CEO drops a complex million-dollar preferred equity deal on your desk - no context, no preparation, just pure startup chaos. Welcome to week one at a fast-growing company where everything happens at once. false full 3 dce1c70a-e0ec-4aa8-96d5-ae63120b4ea0 Wed, 15 Apr 2026 14:21:28 +0000 booking@podgo.io (Brad Firestone) https://gen-x-executive-second-act-at-a-tech-startup.simplecast.com/episodes/new-episode-3smpqaFn Today's Whirlwind Brad Firestone 00:22:15 The email came in at 4:42 in the afternoon. Nine items. Numbered list. No pleasantries beyond "Best." My new company email was live. Slack was set up. Ramp access - that's the expense platform - alre The email came in at 4:42 in the afternoon. Nine items. Numbered list. No pleasantries beyond "Best." My new company email was live. Slack was set up. Ramp access - that's the expense platform - alre false full 1