How real operators build durable businesses under real constraints: capital, regulation, systems, family, and time.
Chief Milestones is a video podcast breaking down the decisions, trade-offs, and structures behind businesses that actually last, told by the people who've had to run them, not just start them with a mortgage, a spouse, and kids in the picture
We talk to entrepreneurs balancing the business with the life around it, bring in doctors to break down hormonal health, chronic stress, sleep, and nutrition for people running a business and a household, feature operators across categories from classical arts studios to influencer-run brands and run a Next Generation series with the kids of entrepreneurial parents because a business that outlasts its founder has to survive physically and generationally.
Subscribe for new episodes every Tuesday and Friday on YouTube. Also on Spotify, Apple Podcasts, and everywhere you listen to podcasts. Clips on Instagram, TikTok, and Facebook.
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