{"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":"From Teacher to Tech CEO: How Stephen Spence Built a Software Company With No Startup Background","slug":"from-teacher-to-tech-ceo-how-stephen-spence-built-a-software-company-with-no-startup-background","published_at":"2026-04-08T12:45:00+00:00","page_url":"https://stenobird.com/podcast/do-small-business-like-a-big-boss-podcast-7627760/from-teacher-to-tech-ceo-how-stephen-spence-built-a-software-company-with-no-startup-background","show_page_url":"https://stenobird.com/podcast/do-small-business-like-a-big-boss-podcast-7627760","url":"https://api.riverside.com/hosting-analytics/media/da5762b98161726dbaf29ebc3cffe7b7ed23eac17379fb658a437af87ab8e4b0/eyJlcGlzb2RlSWQiOiIzMGUyODcwOS02MjFkLTQ4YWMtYjE5Yy01YzRjN2RiMmNkOWUiLCJwb2RjYXN0SWQiOiIwN2NhY2I0Mi03YzBmLTQ0ZDQtODg0ZC04YmUyMzA0MzEyNGUiLCJhY2NvdW50SWQiOiI2ODdhZjZjNWY1MjhmYzVlMDY2ZTc2ZmQiLCJwYXRoIjoibWVkaWEvY2xpcHMvNjlkNTNkZDA5NmRkMzRjMDQ3YWUzMDU3L2Fpc2hhLW1hc3NlbmdpbGxzLXN0dWRpby1jb21wb3Nlci0yMDI2LTQtN19fMTktMjQtMzIubXAzIn0=.mp3","audio_url":"https://api.riverside.com/hosting-analytics/media/da5762b98161726dbaf29ebc3cffe7b7ed23eac17379fb658a437af87ab8e4b0/eyJlcGlzb2RlSWQiOiIzMGUyODcwOS02MjFkLTQ4YWMtYjE5Yy01YzRjN2RiMmNkOWUiLCJwb2RjYXN0SWQiOiIwN2NhY2I0Mi03YzBmLTQ0ZDQtODg0ZC04YmUyMzA0MzEyNGUiLCJhY2NvdW50SWQiOiI2ODdhZjZjNWY1MjhmYzVlMDY2ZTc2ZmQiLCJwYXRoIjoibWVkaWEvY2xpcHMvNjlkNTNkZDA5NmRkMzRjMDQ3YWUzMDU3L2Fpc2hhLW1hc3NlbmdpbGxzLXN0dWRpby1jb21wb3Nlci0yMDI2LTQtN19fMTktMjQtMzIubXAzIn0=.mp3","summary":"In this episode of Do Small Business Like a Big Boss , host Aisha Jorge Massengill sits down with Stephen Spence, Managing Director and Co-Owner of Project MAPIT, to talk about his unconventional journey from a 20-year career in special education to building a thriving software company. Stephen shares how a chance opportunity with a former student led him into the world of startups—without formal business training, funding, or a clear roadmap. From surviving on $37,000 in his first year to cold-walking contractor offices with zero sales experience, to now co-owning a company competing with teams 25x their size, Stephen breaks down the real lessons behind resilience, leadership, and growth. 🎧 What You’ll Learn in This Episode : How to keep going when you're left alone in a business and everything is on the line Why cold outreach often fails—and what actually works for lead generation How radical transparency builds trust and drives revenue Why you should master roles before delegating them What EBITDA is and why it matters for long-term business value How systems, tools, and AI support growth in modern businesses The mindset needed to handle rejection and stay in the game ⏱️ Episode Timestamps : 00:25 – Welcome & What is Project MAPIT 02:47 – From teacher to tech startup: Stephen's origin story 04:30 – When the founder left and Stephen stayed in the fight 07:24 – The family decision and support system 10:50 – Wearing every hat in the early years 13:30 – Lead generation: what worked and what didn’t 16:05 – Handling rejection in sales 18:00 – Learning roles before delegating 21:34 – Buying out a founder 23:53 – Understanding EBITDA 25:45 – Systems, tools, and AI 31:30 – AI in small business 33:06 – Advice for entrepreneurs 36:35 – What “Do Small Business Like a Big Bo…","meta_description":"In this episode of Do Small Business Like a Big Boss , host Aisha Jorge Massengill sits down with Stephen Spence, Managing Director and Co-Owner of Projec…","key_points":[],"chapters":[],"topics":[],"duration_seconds":2202,"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/from-teacher-to-tech-ceo-how-stephen-spence-built-a-software-company-with-no-startup-background/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/from-teacher-to-tech-ceo-how-stephen-spence-built-a-software-company-with-no-startup-background.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}