{"podcast":{"title":"Do Small Business Like a Big Boss Podcast","slug":"do-small-business-like-a-big-boss-podcast-7627760","podcast_index_feed_id":7627760,"rss_url":"https://api.riverside.fm/hosting/OoLlOizM.rss","website_url":"https://sedgwickandrews.com/","image_url":"https://hosting-media.riverside.com/media/podcasts/07cacb42-7c0f-44d4-884d-8be23043124e/logos/e9430cc7-f608-4e67-906f-49a9804b50f7.png","author":"Aisha Massengill","episode_count":17,"summary":"Ready to take your small business from basement startup to Big Boss success? Welcome to Do Small Business Like a Big Boss! where we prove that with the right strategy, any up and coming business owner can compete with the big guys. Hosted by Aisha Jorge Massengill, founder of Sedgwick Andrews Legal & Consulting, a seasoned employment attorney who's advised large publicly traded companies for over two decades, this podcast is your courtside seat to business transformation. Just like that fearless 13-year-old girl shouting \"\"I got next!\"\" on Bronx basketball courts, successful entrepreneurs don't just wait their turn—they prepare for it. They study the game, assess the competition, and build the skills they need to win when opportunity calls. What You'll Discover: Real Success Stories: In-depth interviews with business owners who've successfully scaled from side hustles to legitimate enterprises Strategic Frameworks: Proven systems and structures that help small businesses compete like industry giants Legal & HR Insights: Employment law guidance that protects your growing team while fostering company culture Risk Management for Entrepreneurs: Smart ways to minimize liability while m…","last_synced_at":null,"page_url":"https://stenobird.com/podcast/do-small-business-like-a-big-boss-podcast-7627760"},"episode":{"title":"The Leadership Skill Nobody Teaches (But Every CEO Needs) | Richard Yep","slug":"the-leadership-skill-nobody-teaches-but-every-ceo-needs-richard-yep","published_at":"2026-02-04T16:05:51+00:00","page_url":"https://stenobird.com/podcast/do-small-business-like-a-big-boss-podcast-7627760/the-leadership-skill-nobody-teaches-but-every-ceo-needs-richard-yep","show_page_url":"https://stenobird.com/podcast/do-small-business-like-a-big-boss-podcast-7627760","url":"https://api.riverside.com/hosting-analytics/media/34da3614b15396e269a5543e2789b2769a8e03d0576136ef55b4a3c715895467/eyJlcGlzb2RlSWQiOiIxYTM1NGMzOS01ZDAyLTRmODgtOTI1NS05NjQ5ODY2MmI4ZWIiLCJwb2RjYXN0SWQiOiIwN2NhY2I0Mi03YzBmLTQ0ZDQtODg0ZC04YmUyMzA0MzEyNGUiLCJhY2NvdW50SWQiOiI2ODdhZjZjNWY1MjhmYzVlMDY2ZTc2ZmQiLCJwYXRoIjoibWVkaWEvY2xpcHMvNjk4MzcwNjQwNDQ4OTEzMDgwYTYwOTcwL2Fpc2hhLW1hc3NlbmdpbGxzLXN0dWRpby1jb21wb3Nlci0yMDI2LTItNF9fMTctMTQtMjgubXAzIn0=.mp3","audio_url":"https://api.riverside.com/hosting-analytics/media/34da3614b15396e269a5543e2789b2769a8e03d0576136ef55b4a3c715895467/eyJlcGlzb2RlSWQiOiIxYTM1NGMzOS01ZDAyLTRmODgtOTI1NS05NjQ5ODY2MmI4ZWIiLCJwb2RjYXN0SWQiOiIwN2NhY2I0Mi03YzBmLTQ0ZDQtODg0ZC04YmUyMzA0MzEyNGUiLCJhY2NvdW50SWQiOiI2ODdhZjZjNWY1MjhmYzVlMDY2ZTc2ZmQiLCJwYXRoIjoibWVkaWEvY2xpcHMvNjk4MzcwNjQwNDQ4OTEzMDgwYTYwOTcwL2Fpc2hhLW1hc3NlbmdpbGxzLXN0dWRpby1jb21wb3Nlci0yMDI2LTItNF9fMTctMTQtMjgubXAzIn0=.mp3","summary":"In this episode of Do Small Business Like a Big Boss , host Aisha Jorge Massengill , Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC , sits down with Richard Yep , Vice President of Vetted Solutions , to talk about the real challenges of leadership—especially the difficult transition from being someone’s peer to becoming their boss. Richard brings decades of leadership experience from nonprofit organizations and executive search, sharing hard-earned insights on building inclusive cultures, hiring the right people, and making values-based decisions even when they come at a cost. This conversation explores what worked, what didn’t, and what every entrepreneur, CEO, and emerging leader needs to hear as they grow their organization. 🎧 What You’ll Learn in This Episode: How to navigate the awkward but essential transition from peer to boss without losing trust Why hiring for passion over perfect qualifications attracts the right talent to small businesses How to balance finances with growth—and why patience often matters more than speed How inclusive leadership improves decision-making and organizational effectiveness When to delegate, how to let go, and why listening is a leadership superpower The real cost of values-based decisions—and why they define organizational integrity Practical advice for entrepreneurs preparing to scale ⏱️ Episode Timestamps: 00:00 – Introduction 02:54 – Navigating the challenges of leadership 05:53 – Hiring and attracting talent in small businesses 08:54 – Balancing finances and growth 11:55 – Common challenges for CEOs and nonprofit leaders 14:53 – The importance of communication and inclusivity 17:47 – Delegation and letting go 20:35 – Values-based decision making 23:35 – Building an inclusive culture 26:39 – Piv…","meta_description":"In this episode of Do Small Business Like a Big Boss , host Aisha Jorge Massengill , Founder and Principal Attorney at Sedgwick Andrews Legal & Consul…","key_points":[],"chapters":[],"topics":[],"duration_seconds":2096,"processing_state":"not_requested","actions":[{"name":"request_transcript","method":"POST","url":"https://stenobird.com/v1/public/podcasts/do-small-business-like-a-big-boss-podcast-7627760/episodes/the-leadership-skill-nobody-teaches-but-every-ceo-needs-richard-yep/transcription-requests","description":"Idempotently request low-priority transcript generation for this episode."},{"name":"read_markdown","method":"GET","url":"https://stenobird.com/podcast/do-small-business-like-a-big-boss-podcast-7627760/the-leadership-skill-nobody-teaches-but-every-ceo-needs-richard-yep.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}