Jason Wojo: Dating, Money & Power Dynamics Explained | DSH #1723

What does masculinity even mean anymore? In this raw, unfiltered conversation, Jason Wojo breaks down boundaries, relationships, money, business, culture, and why so many men feel lost right now. From dating dynamics and moving out early, to building a 100-person agency, rejecting fake online gurus, questioning gym culture, and calling out financial delusion — this episode is honest, controversial, and grounded in real experience. We talk about: • Why boundaries define masculinity • Modern relationships and respect • Moving out young vs staying comfortable • Why most online “leaders” are selling air • Agency life, bad clients, and real scale • Why discipline beats motivation • The hidden cost of validation culture • Money, debt, and financial delusion • Sleep, health, and sustainable performance • Why leadership starts at home This isn’t motivation. It’s perspective. Chapters 00:00 Why Masculinity Is Really About Boundaries 02:17 Dating, Respect & Power Dynamics 05:16 Miami, Materialism & Flex Culture 07:54 Scaling an Agency to 100 Employees 11:12 Why Most Online Gurus Are Fake 15:00 AI, Data & The Future of Business 19:12 Debt, Financing & Financial Delusion 23:41 Leadership Starts at Home 28:31 Moving Out Young Changes Everything 40:30 Why Sleep Beats the Gym 🎙️ APPLY OR CONNECT 👉 Apply to be on the podcast: https://www.digitalsocialhour.com/application 📩 Business inquiries / sponsors: sean@digitalsocialhour.com 👤 GUEST: Jason Wojciechowicz - https://www.instagram.com/thejasonwojo/ https://wojorunsads.com/start 💼 SPONSORS QUINCE: https://quince.com/dsh 🥗 Fuel your health with Viome: https://buy.viome.com/SEAN Use code “Sean” at checkout for a discount! 🎧 LISTEN ON 🍏 Apple Podcasts: https://podcasts.apple.com/us/podcast/digital-social-hour/id1676846015 🎵 Spotify: https://open.spotify.com/show/5Jn7LXarRlI8Hc0GtTn759 📸 Sean Kelly Instagram: @seanmikekelly ⚠️ DISCLAIMER The views and opinions expressed by guests on Digital Social Hour are solely those of the individuals appearing on the podcast and do not necessarily reflect the views or opinions of the host, Sean Kelly, or the Digital Social Hour team. While we encourage open and honest discussions, Sean Kelly is not legally responsible for any statements, claims, or opinions made by guests during the show. Listeners are encouraged to form their own opinions and seek professional advice where appropriate. The content shared is for entertainment and informational purposes only — it should not be taken as legal, medical, financial, or professional advice. We strive to present accurate and reliable information; however, we make no guarantees regarding its completeness or accuracy. The views expressed are solely those of the speakers and do not necessarily represent those of the producers or affiliates of this program. 🔥 Stay tuned for more episodes featuring top creators, founders, and innovators shaping the digital world! 🔑 Keywords modern masculinity podcast, jason wojo interview, boundaries in relationships, leadership for men, agency owner reality, online guru culture, gen z masculinity, hustle culture debate, financial delusion, debt culture discussion See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info . Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.