{"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":"From Engineering to Landscaping COO: Recurring Revenue, Smart Hiring & Systems That Scale","slug":"from-engineering-to-landscaping-coo-recurring-revenue-smart-hiring-systems-that-scale","published_at":"2026-07-01T12:43:23+00:00","page_url":"https://stenobird.com/podcast/do-small-business-like-a-big-boss-podcast-7627760/from-engineering-to-landscaping-coo-recurring-revenue-smart-hiring-systems-that-scale","show_page_url":"https://stenobird.com/podcast/do-small-business-like-a-big-boss-podcast-7627760","url":"https://api.riverside.com/hosting-analytics/media/82310b0f342ffbe93f8e0b5b465f2031df9b08620aecfe1e897443be4b251ee7/eyJlcGlzb2RlSWQiOiIxZDljM2YwMS1kOGEyLTQ4MzQtOTQzNi02Zjc1NmM2NTVkOWQiLCJwb2RjYXN0SWQiOiIwN2NhY2I0Mi03YzBmLTQ0ZDQtODg0ZC04YmUyMzA0MzEyNGUiLCJhY2NvdW50SWQiOiI2ODdhZjZjNWY1MjhmYzVlMDY2ZTc2ZmQiLCJwYXRoIjoibWVkaWEvY2xpcHMvNmE0NTBiNmNiZDM1MWJhZGFiZDgyMGVmL2Fpc2hhLW1hc3NlbmdpbGxzLXN0dWRpby1jb21wb3Nlci0yMDI2LTctMV9fMTQtNDMtMjQubXAzIn0=.mp3","audio_url":"https://api.riverside.com/hosting-analytics/media/82310b0f342ffbe93f8e0b5b465f2031df9b08620aecfe1e897443be4b251ee7/eyJlcGlzb2RlSWQiOiIxZDljM2YwMS1kOGEyLTQ4MzQtOTQzNi02Zjc1NmM2NTVkOWQiLCJwb2RjYXN0SWQiOiIwN2NhY2I0Mi03YzBmLTQ0ZDQtODg0ZC04YmUyMzA0MzEyNGUiLCJhY2NvdW50SWQiOiI2ODdhZjZjNWY1MjhmYzVlMDY2ZTc2ZmQiLCJwYXRoIjoibWVkaWEvY2xpcHMvNmE0NTBiNmNiZDM1MWJhZGFiZDgyMGVmL2Fpc2hhLW1hc3NlbmdpbGxzLXN0dWRpby1jb21wb3Nlci0yMDI2LTctMV9fMTQtNDMtMjQubXAzIn0=.mp3","summary":"In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Doug Bonnell, Owner and COO of True North Landscaping, to talk about his journey from automotive engineer to leading and scaling a successful family-owned landscaping company. This conversation covers the real-life lessons behind building a sustainable service business, creating recurring revenue, making strategic hires, and implementing systems that support long-term growth. 🎧 What You’ll Learn in This Episode: Why recurring revenue is the foundation of a stable service-based business How to decide whether to hire, outsource, or acquire to fill business gaps The systems and software that transformed operations and job costing How Doug and his wife successfully work together in the business What every entrepreneur can learn from the landscaping industry's referral culture ⏱️ Episode Timestamps: 00:00 – Introduction 00:35 – Guest introduction: Doug Bonnell & True North Landscaping 01:17 – From automotive engineer to family business COO 03:03 – Taking the leap from corporate life 05:42 – Learning the business from the ground up 06:57 – Building recurring revenue through maintenance services 09:21 – Why recurring revenue matters 11:12 – Acquiring a competitor and expanding services 12:13 – Build, hire, or buy? 14:31 – Managing seasonality and workforce challenges 20:23 – Work-life balance as a business owner 23:43 – Running a business with your spouse 24:51 – Common mistakes customers make when hiring contractors 29:26 – Systems and technology that drive growth 32:12 – Advice for aspiring entrepreneurs 33:05 – What “Do Small Business Like a Big Boss” means to Doug 33:52 – Where to connect with Doug and True North Landscaping 👤 About the Guest: Doug Bonnell is the Owner and…","meta_description":"In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Doug Bonnell, Owner and COO of True North Landscaping, to…","key_points":[],"chapters":[],"topics":[],"duration_seconds":1744,"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-engineering-to-landscaping-coo-recurring-revenue-smart-hiring-systems-that-scale/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-engineering-to-landscaping-coo-recurring-revenue-smart-hiring-systems-that-scale.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}