{"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":23,"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":"2026-07-23T00:19:55.255262+00:00","page_url":"https://stenobird.com/podcast/do-small-business-like-a-big-boss-podcast-7627760"},"episode":{"title":"Outsmarting the Big Guys: Building a Challenger Brand Agency from Scratch","slug":"outsmarting-the-big-guys-building-a-challenger-brand-agency-from-scratch","published_at":"2026-07-09T12:49:35+00:00","page_url":"https://stenobird.com/podcast/do-small-business-like-a-big-boss-podcast-7627760/outsmarting-the-big-guys-building-a-challenger-brand-agency-from-scratch","show_page_url":"https://stenobird.com/podcast/do-small-business-like-a-big-boss-podcast-7627760","url":"https://api.riverside.com/hosting-analytics/media/b309dc0b2c6e1e6108133e8efda98fa27e7e367177665ee75ce7689c478a369c/eyJlcGlzb2RlSWQiOiJlNzE0ODc3OS0wYjVjLTQzMzgtYjU1NS05Y2QwNjUxZDc1NzkiLCJwb2RjYXN0SWQiOiIwN2NhY2I0Mi03YzBmLTQ0ZDQtODg0ZC04YmUyMzA0MzEyNGUiLCJhY2NvdW50SWQiOiI2ODdhZjZjNWY1MjhmYzVlMDY2ZTc2ZmQiLCJwYXRoIjoibWVkaWEvY2xpcHMvNmE0Zjk5NTg4ODI1NWRhYWJjM2Y0MmQ2L2Fpc2hhLW1hc3NlbmdpbGxzLXN0dWRpby1jb21wb3Nlci0yMDI2LTctOV9fMTQtNTEtMzYubXAzIn0=.mp3","audio_url":"https://api.riverside.com/hosting-analytics/media/b309dc0b2c6e1e6108133e8efda98fa27e7e367177665ee75ce7689c478a369c/eyJlcGlzb2RlSWQiOiJlNzE0ODc3OS0wYjVjLTQzMzgtYjU1NS05Y2QwNjUxZDc1NzkiLCJwb2RjYXN0SWQiOiIwN2NhY2I0Mi03YzBmLTQ0ZDQtODg0ZC04YmUyMzA0MzEyNGUiLCJhY2NvdW50SWQiOiI2ODdhZjZjNWY1MjhmYzVlMDY2ZTc2ZmQiLCJwYXRoIjoibWVkaWEvY2xpcHMvNmE0Zjk5NTg4ODI1NWRhYWJjM2Y0MmQ2L2Fpc2hhLW1hc3NlbmdpbGxzLXN0dWRpby1jb21wb3Nlci0yMDI2LTctOV9fMTQtNTEtMzYubXAzIn0=.mp3","summary":"In this episode of Do Small Business Like a Big Boss , host Aisha Jorge Massengill sits down with Justin Bajan, Co-Founder and Creative Director of Familiar Creatures, to talk about leaving a six-figure career to build an award-winning independent advertising agency from the ground up. Justin shares how his team helps challenger brands outsmart larger competitors, the realities of entrepreneurship, and the lessons that helped Familiar Creatures become one of Adweek’s fastest-growing agencies. 🎧 What You’ll Learn in This Episode: How Justin transitioned from corporate life to launching his own agency The realities of pricing professional services and avoiding undervaluing your work How Familiar Creatures evaluates potential clients using its “Smiley Face System” Why saying no to the wrong opportunities can accelerate long-term growth How small, agile teams can outperform much larger competitors ⏱️ Episode Timestamps: 00:03 – Introduction 01:10 – Leaving a six-figure salary 02:56 – Moving his family to start over 03:26 – Why Richmond became home for the business 07:09 – Landing the first anchor client 09:20 – The financial realities of early entrepreneurship 11:58 – Learning while building the business 13:52 – Pricing professional services 17:22 – Building a reputation over time 18:33 – Making decisions as business partners 21:47 – The creative process behind successful campaigns 26:06 – Scaling the agency from 2 to 10 people 29:30 – Choosing the right clients 30:23 – The “Smiley Face System” explained 33:23 – Why saying no can be the best business decision 37:57 – How small teams outperform big agencies 41:08 – What “Do Small Business Like a Big Boss” means to Justin 43:06 – Where to connect with Justin and Familiar Creatures 👤 About the Guest: Justin Bajan is the Co-Fo…","meta_description":"In this episode of Do Small Business Like a Big Boss , host Aisha Jorge Massengill sits down with Justin Bajan, Co-Founder and Creative Director of Famili…","key_points":[],"chapters":[],"topics":[],"duration_seconds":2243,"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/outsmarting-the-big-guys-building-a-challenger-brand-agency-from-scratch/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/outsmarting-the-big-guys-building-a-challenger-brand-agency-from-scratch.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}