{"podcast":{"title":"The Friday Habit","slug":"the-friday-habit-1209031","podcast_index_feed_id":1209031,"rss_url":"https://feeds.transistor.fm/the-friday-habit","website_url":"http://www.thefridayhabit.com","image_url":"https://img.transistorcdn.com/N35exE95CVyDQfQvBwhSQ0SAxOOwoZIY8KhjaJVB8Pk/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS81YWU1/ODlkMDNkMWVlZTI4/YWZiMTBjMDUxYjQ3/ZDg4NC5qcGc.jpg","author":"Mark Labriola II","episode_count":228,"summary":"Grow your business. Lead with purpose. Love your life. The Friday Habit gives entrepreneurs and small business owners actionable tips, inspiring interviews, and real-world strategies to help you scale smart and stay sane. Hosted by Mark Labriola II, this weekly show is your permission slip to build a business that works for you—not the other way around.","last_synced_at":"2026-07-17T20:18:39.451541+00:00","page_url":"https://stenobird.com/podcast/the-friday-habit-1209031"},"episode":{"title":"Why Regret Is More Dangerous Than Risk With Henry Yoshida","slug":"why-regret-is-more-dangerous-than-risk-with-henry-yoshida","published_at":"2026-02-13T13:00:00+00:00","page_url":"https://stenobird.com/podcast/the-friday-habit-1209031/why-regret-is-more-dangerous-than-risk-with-henry-yoshida","show_page_url":"https://stenobird.com/podcast/the-friday-habit-1209031","url":"https://share.transistor.fm/s/6d0421ab","audio_url":"https://media.transistor.fm/6d0421ab/c722b9ca.mp3","summary":"In this episode of The Friday Habit, host Mark Labriola II sits down with Henry Yoshida, CEO and Co-Founder of Rocket Dollar, to unpack what it really takes to build a durable fintech company in a highly regulated industry. Henry shares his journey from a risk-averse upbringing and a stable career at Merrill Lynch to founding multiple companies—including Rocket Dollar, now part of a platform managing $12B+ in retirement assets. They dive deep into ownership, timing, regret vs. risk, venture capital trade-offs, and why paying attention to “small signals” can unlock massive opportunities. 🧠 Key Takeaways Regret Is More Dangerous Than Risk – Fear fades, but “what if?” lingers Stay a Mile Deep, Not a Mile Wide – Specialization creates leverage Timing Matters More Than Ideas – Many failures are just too early Venture Capital Is a Clock – Momentum determines survival Build for the Right Customer Segment – CAC must beat LTV Balance Fuels Longevity – Burnout kills good businesses Curiosity Compounds – Small observations connect into big ideas Resources & Links: 🔗 Learn more about Rocket Dollar: https://bit.ly/4qaDVxU Connect With Henry! Instagram: @fitfinancehenry 📘 Download the free Friday Habit Guide: https://thefridayhabit.com Chapters: 00:42 Meet Henry Yoshida: CEO & Co-Founder of Rocket Dollar 02:05 Growing Up Risk-Averse & Fear of Regret 04:45 Merrill Lynch’s Competitive Culture 07:55 Early Career Lessons That Shaped a Founder 10:40 Leaving Stability to Take the Leap 13:10 Building & Selling the First Business 16:00 Venture Capital, Timing, and Momentum 18:55 Failing Into an Acquisition 21:35 Why Most Startups Pick the Wrong Customer 24:10 The Problem With Traditional IRAs & 401ks 27:10 What Rocket Dollar Actually Does 30:05 Building in a Highly Regul…","meta_description":"In this episode of The Friday Habit, host Mark Labriola II sits down with Henry Yoshida, CEO and Co-Founder of Rocket Dollar, to unpack what it really tak…","key_points":[],"chapters":[],"topics":[],"duration_seconds":2445,"processing_state":"not_requested","actions":[{"name":"request_transcript","method":"POST","url":"https://stenobird.com/v1/public/podcasts/the-friday-habit-1209031/episodes/why-regret-is-more-dangerous-than-risk-with-henry-yoshida/transcription-requests","description":"Idempotently request low-priority transcript generation for this episode."},{"name":"read_markdown","method":"GET","url":"https://stenobird.com/podcast/the-friday-habit-1209031/why-regret-is-more-dangerous-than-risk-with-henry-yoshida.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}