Do Small Business Like a Big Boss Podcast

Aisha Massengill
  • 5.0 (38)
  • Entrepreneurship

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 maximizing opportunity Perfect for: Entrepreneurs ready to legitimize their side hustles into scalable businesses Small Business Owners (10-250 employees) seeking strategic growth frameworks HR Professionals navigating employment challenges in growing companies Ambitious Leaders who refuse to let limited resources limit their vision Each episode features candid interviews with business owners and operators who have navigated the challenges of growth, overcome obstacles, and achieved extraordinary success. Whether you’re scaling your team, refining your business model, or developing a winning mindset, this podcast provides the inspiration and guidance you need to build with discipline, confidence, and purpose. Your turn is coming. Are you ready? New episodes drop every week because champions don't take days off. Subscribe now and join thousands of entrepreneurs who refuse to wait on the sidelines. Your business growth journey starts here.

  1. 18h ago

    Why Digital Literacy Is the New Small Business Skill | Do Small Business like a Big Boss

    Thinking about turning your side project into a nonprofit or small business? Ian Kimble breaks down exactly what to lock in early — starting with the two moves most founders put off too long. Ian Kimble is the co-founder and executive director of Black Tech Philly, a Philadelphia nonprofit expanding access to tech education, digital literacy, and AI literacy. What started as a conversation with a stranger coding in a coffee shop back in 2019 is now a program running in four Philadelphia schools, hosting city-wide Tech Town Halls, and building a growing community of tech professionals and aspiring entrepreneurs. Aisha and Ian talk through the free legal resources that helped him formalize the organization, the importance of building the right kind of  culture that shaped how his team hires and holds people accountable, and how storytelling — not advertising — became his biggest lead source. 💡 What You'll Learn How to find free legal help for 501(c)(3) formation through pro bono lawyer programs like Philly VIPWhy culture isn't your website's mission statement — it's the worst behavior you're willing to tolerate — and how to set that standard earlyHow showing up in person and telling one specific, sticky story about your business turns into inbound leads How to balance a full-time job with building your business in the early days without burning out ⏱️ Episode Timestamps 00:02 – Welcome & meet Ian Kimble 00:55 – The coffee shop conversation that started Black Tech Philly 02:20 – What Black Tech Philly does today 05:20 – Is the appetite really there for tech & AI literacy? 09:39 – Deepfakes, media literacy, and “trust but verify” 12:23 – Getting free legal help early through Philly VIP 16:03 – The real definition of company culture 19:39 – How a LinkedIn shoutout sparked momentum 21:15 – Turning story and “being in the field” into inbound leads 28:27 – From political science to insurance sales to code 32:23 – The moment coding became “the thing” 33:53 – Building a sales pipeline for community partnerships 35:48 – Balancing a full-time job while building the org 43:06 – Why the name “Black Tech Philly” was intentional 44:57 – What “Do Small Business Like a Big Boss” means to Ian 46:06 – Where to find Black Tech Philly 🎤 About Our Guest Ian Kimble is the co-founder and executive director of Black Tech Philly, a Philadelphia-based educational nonprofit founded in spring 2020, focused on expanding access to technology, digital literacy, and AI literacy across the city. Website: https://blacktechphilly.org Ian on LinkedIn: linkedin.com/in/iank6 Take the free Small Business Legal Risk Self-Assessment and get clarity before a contract, a lawsuit, or a bad partnership does it for you. 👉 Grab your assessment here: www.smallbizzlegalguide.com 🔗 Stay Connected with Sedgwick Andrews: Follow us across all platforms for legal tips, business strategy, and boss-level motivation: 👉 https://linktr.ee/Sedgwick_Andrews_LC Podcast Mantra: Build the dream messy, build it scared, just don't build it small.

  2. Jul 22

    From Corporate Dropout to 6-Figure CEO: How Shan Thomas Built on Her Own Terms

    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 Shan Thomas, founder of Credible Visibility Media, to discuss how she left a six-figure corporate career to build a thriving business on her own terms. Shan shares how she leveraged her corporate experience, developed profitable systems, and created a business that delivers both financial success and work-life balance. This conversation covers the real-life lessons behind building a business from the ground up—what worked, what didn't, and what every aspiring entrepreneur needs to hear. 🎧 What You'll Learn in This Episode: How to leverage corporate experience to build credibility as an entrepreneur The Bullseye Strategy for attracting ideal clients without limiting growth A pricing framework to confidently raise your rates How the TAGS Framework helps create a signature offer that stands out Why your ideal client is often the person you were 5–10 years ago ⏱️ Episode Timestamps: 00:00 – Introduction 00:52 – Guest introduction: Shan Thomas 02:50 – From corporate career to entrepreneurship 08:34 – Overcoming challenges in a male-dominated industry 13:40 – Quitting without a plan and starting a business 19:36 – Faith, fear, and betting on yourself 25:00 – Profit strategy and revenue planning 27:08 – The Bullseye Strategy for client messaging 30:00 – The TAGS Framework 36:28 – Pricing with confidence 39:19 – Building the "10–4 Life" 42:41 – What "Do Small Business Like a Big Boss" means 44:24 – Wrap-up & calls to action 👤 About the Guest: Shan Thomas is the founder of Credible Visibility Media, where she helps service-based business owners increase profitability through strategic positioning, signature offers, and scalable systems. Drawing from decades of Fortune 500 experience negotiating billion-dollar logistics contracts, Shan brings big-business strategies to small business owners. She is also the founder of Entrepreneur Her, an Atlanta-based community supporting women entrepreneurs. Connect with Shan: LinkedIn — @shanthomasbiz Ready to find out where your business is legally exposed?* Take the free Small Business Legal Risk Self-Assessment and get clarity before a contract, a lawsuit, or a bad partnership does it for you. 👉 Grab your assessment here: www.smallbizzlegalguide.com 🔗 Stay Connected with Sedgwick Andrews: Follow us across all platforms for legal tips, business strategy, and boss-level motivation: 👉 https://linktr.ee/Sedgwick_Andrews_LC Podcast Mantra: Build the dream messy, build it scared, just don't build it small. If this episode helped you, don't forget to subscribe, download, and share it with another boss who needs to hear it.

  3. Jul 15

    How to Know When to Outsource

    In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Brad Stevens, founder and CEO of Outsource Access, to talk about knowing when it's time to outsource and how to build a team that helps your business grow. Brad shares his entrepreneurial journey, the unexpected path that led him to build a 500+ employee offshore staffing company, and the systems, mindset, and metrics that have fueled his rapid growth. 🎧 What You’ll Learn in This Episode: The two-question exercise to identify what you should outsource firstHow to view hiring as an investment instead of an expenseWhy Outsource Access serves businesses across 85 industries instead of specializing in one nicheThe key performance indicators Brad uses to measure outsourcing successHow educational content and referrals helped grow the business without paid advertising ⏱️ Episode Timestamps 01:38 – Brad's origin story: renting Micro Machines toys in 4th grade 05:00 – Learning to spot problems worth solving 08:02 – The moment Brad knew entrepreneurship was the path 13:38 – How Brad thinks about building resilience 18:58 – The exploding pen disaster that led to Outsource Access 25:07 – Why Brad built his team in the Philippines 26:18 – Why Outsource Access serves 85 industries instead of niching down 29:49 – Building word-of-mouth marketing through content and education 33:45 – The two-question exercise for knowing what to outsource 40:14 – The 3 KPIs Brad watches most closely 44:27 – Brad's upcoming book, Automate and Delegate 48:38 – What "Do Small Business Like a Big Boss" means to Brad 🎤 About Our Guest Brad Stevens is the founder and CEO of Outsource Access, an offshore virtual staffing firm he's grown to 500+ employees across 85 industries in just four and a half years. In 2021, Outsource Access was the only outsourcing company to receive Inc. magazine's Best in Business Award for firms making the biggest impact on their communities, industries, and the environment. His book, Automate and Delegate, is releasing soon. 🔗 Stay Connected with Sedgwick Andrews 👉 https://linktr.ee/Sedgwick_Andrews_LC Want to see how your business stacks up? Download this business self-assessment: www.smallbizzlegalguide.com Build the dream messy, build it scared, just don’t build it small. If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it.

  4. Jul 9

    Outsmarting the Big Guys: Building a Challenger Brand Agency from Scratch

    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 agencyThe realities of pricing professional services and avoiding undervaluing your workHow Familiar Creatures evaluates potential clients using its “Smiley Face System”Why saying no to the wrong opportunities can accelerate long-term growthHow small, agile teams can outperform much larger competitors ⏱️ Episode Timestamps: 00:03 – Introduction01:10 – Leaving a six-figure salary02:56 – Moving his family to start over03:26 – Why Richmond became home for the business07:09 – Landing the first anchor client09:20 – The financial realities of early entrepreneurship11:58 – Learning while building the business13:52 – Pricing professional services17:22 – Building a reputation over time18:33 – Making decisions as business partners21:47 – The creative process behind successful campaigns26:06 – Scaling the agency from 2 to 10 people29:30 – Choosing the right clients30:23 – The “Smiley Face System” explained33:23 – Why saying no can be the best business decision37:57 – How small teams outperform big agencies41:08 – What “Do Small Business Like a Big Boss” means to Justin43:06 – Where to connect with Justin and Familiar Creatures 👤 About the Guest: Justin Bajan is the Co-Founder and Creative Director of Familiar Creatures, an independent advertising agency based in Richmond, Virginia. Since launching in 2018, the agency has been recognized as one of Adweek’s 25 fastest-growing agencies and has helped challenger brands like Duke’s Mayonnaise, Crunch Fitness, and Bubba Burger achieve remarkable growth through strategic creative marketing. Website: familiarcreatures.com Instagram: @familiarcreatures Want to see how your business stacks up? Download this business self-assessment: www.smallbizzlegalguide.com Stay Connected with Sedgwick Andrews: 👉 https://linktr.ee/Sedgwick_Andrews_LC Build the dream messy, build it scared, just don't build it small. If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it. 🎧

  5. Jul 1

    From Engineering to Landscaping COO: Recurring Revenue, Smart Hiring & Systems That Scale

    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 COO of True North Landscaping, a high-end residential design, build, and maintenance company serving Northern Michigan. After earning an engineering degree from Western Michigan University and spending six years in the automotive industry, Doug joined the family business and has helped grow it into a 50-person operation with multiple service lines, including maintenance, irrigation, fertilization, and snow removal. Connect with Doug: LinkedIn: Doug Bonnell Website: True North Landscaping 🚀 Ready to Make Your Business Official? Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence. 👉 Register here: https://www.igotnext.co/training 👉 Grab your FREE Legal Guide at: 📘 Free Guide: www.smallbizzlegalguide.com 🔗 Stay Connected with Sedgwick Andrews: Follow us across all platforms for legal tips, business strategy, and boss-level motivation: 👉 https://linktr.ee/Sedgwick_Andrews_LC Podcast Mantra: Build the dream messy, build it scared, just don’t build it small. If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it. 🎧

  6. Jun 24

    Building Six-Figures Organically: Social Media, Government Contracts & Community

    In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Myown Holmes, Owner and Senior Strategist of Socially Polished and Founder of The Prism Effect, to talk about building a six-figure business organically while balancing family, a full-time career, and entrepreneurship. Myown shares how she leveraged social media, strategic relationships, and community-building to grow her business, navigate government contracting opportunities, and create a platform that empowers minority women entrepreneurs. 🎧 What You’ll Learn in This Episode: How the “Power of One” framework can help you grow without burnout Why focusing on one platform can outperform trying to be everywhere at once How to build a referral network and secure early testimonials through strategic partnerships The government contracting opportunities many small business owners overlook Why knowing your numbers and building the right advisory team is critical for growth ⏱️ Episode Timestamps: 00:04 – Welcome & guest introduction 01:04 – Building a business while raising a family 03:31 – The realities of building in the margins 07:25 – Knowing when it was time to leave her job 09:22 – Creating a structurally sound business 13:35 – Breaking into government contracting 16:12 – Diversifying revenue vs. stabilizing revenue 17:50 – The “always be marketing” mindset 18:57 – Knowing your numbers and building your dream team 22:38 – Finding the right platform for your audience 23:31 – The Power of One framework 26:04 – Organic marketing vs. paid advertising 31:10 – Building a referral network through bartering 35:59 – Using AI in small business 39:01 – The hardest lessons of entrepreneurship 40:26 – The mission behind The Prism Effect 46:22 – What “Do Small Business Like a Big Boss” means to Myown 48:22 – Where to connect with Myown 👤 About the Guest: Myown Holmes is the Owner and Senior Strategist of Socially Polished, a boutique digital marketing agency based in Washington, D.C., specializing in social media strategy, personal branding, B2B social selling, and brand management. She is also the Founder of The Prism Effect, a community dedicated to supporting the mindset, wellness, and business growth of minority women entrepreneurs. Connect with Myown: LinkedIn: https://www.linkedin.com/in/myownh/ Website: https://socially-polished.com/ 🚀 Ready to Make Your Business Official? Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence. 👉 Register here: https://www.igotnext.co/training 👉 Grab your FREE Legal Guide at: https://www.topemployermistakes.com https://smallbizzlegalguide.com 🔗 Stay Connected with Sedgwick Andrews: Follow us across all platforms for legal tips, business strategy, and boss-level motivation: 👉 https://linktr.ee/Sedgwick_Andrews_LC Podcast Mantra: Build the dream messy, build it scared, just don’t build it small.

  7. May 27

    If You Don't Have a Client Plan, You Have a Time Bomb

    In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with David Cassel, co-founder and CTO of 4V Services, to talk about the realities of growing a consultancy, scaling a team, and building a business that doesn’t rely solely on referrals.  David shares the lessons he learned growing 4V Services from a small operation into a team of 18, the hard decisions that came with scaling back, and why every entrepreneur needs a real client acquisition strategy before growth becomes a problem. 🎧 What You’ll Learn in This Episode: How David evaluates business ideas using a 4-category frameworkWhy relying only on referrals can become a major business riskHow to identify skill gaps and decide whether to learn, hire, or outsourceWhat it’s like building and running a business with your spouseWhat a fractional CTO does and how it helps growing businesses scale strategically ⏱️ Episode Timestamps: 00:14 – Welcome & guest introduction00:35 – David’s origin story and launching 4V Services04:06 – The 4-category framework for evaluating business ideas08:56 – Landing early clients through referrals10:21 – Understanding the MarkLogic niche11:37 – Why referrals alone are a “time bomb”16:17 – Scaling back and lessons on focus18:40 – Strategic hiring and organic growth22:28 – The challenge of training clients too well24:35 – Balancing big clients and smaller accounts26:04 – Running a business with your spouse29:44 – The shift into fractional CTO services36:28 – Advice David would give his younger self38:01 – What “Do Small Business Like a Big Boss” means to David 👤 About the Guest: David Cassel is the co-founder and CTO of 4V Services, a consultancy focused on helping enterprise organizations maximize their MarkLogic investments while applying operational strategy to software development. After nearly a decade at MarkLogic, David launched 4V Services with his wife and grew the business organically to a team of 18. He now helps businesses through fractional CTO services, providing executive-level technology leadership without the cost of a full-time hire. Connect with David:   LinkedIn: David Cassel Website: 4vservices.com 🚀 Ready to Make Your Business Official? Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence. 👉 Register here: https://www.igotnext.co/training 👉 Grab your FREE Legal Guide at: https://www.smallbizzlegalguide.com 🔗 Stay Connected with Sedgwick Andrews: Follow us across all platforms for legal tips, business strategy, and boss-level motivation: 👉 https://linktr.ee/Sedgwick_Andrews_LC Podcast Mantra: Build the dream messy, build it scared, just don’t build it small. 🎧 If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

  8. May 20

    The Bootstrapped EdTech Playbook: Offshore Teams, DIY PR, and 20K Users

    In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Regnault Drake Sanders, founder of School Economy Inc., to talk about building an EdTech company from scratch with no outside funding. Starting with just $2,000 in Amazon gift cards, Regnault built a platform that rewards K-12 students for academic engagement and now serves over 20,000 active students across New York, Atlanta, and Dallas. This conversation dives into validation, partnerships, grassroots growth, AI automation, and what it really takes to build a mission-driven business that also generates sustainable revenue. 🎧 What You’ll Learn in This Episode: How to validate a business idea before investors or partnersWhy non-technical founders need a technical allyHow AI tools like Zapier and N8N streamline operationsHow major partnerships and relationships drive growthBuilding mission-driven revenue with repeatable sponsorships ⏱️ Episode Timestamps: 00:02 – Intro & guest welcome 01:25 – Origin of School Economy 03:20 – Mission behind the business 06:52 – How the platform works 09:25 – Referral & growth system 11:25 – Sponsorship ROI model 12:05 – Starting with $2,000 12:58 – Scaling to 20,000 users 16:16 – Building partnerships 17:40 – First 50 users via outreach 20:03 – Tech companies as people businesses 21:04 – Managing offshore dev teams 24:25 – Bootstrapping without VC 26:10 – Scaling with AI automation 27:47 – DIY PR & media coverage 32:08 – “Do Small Business Like a Big Boss” 33:04 – Where to connect 👤 About the Guest: Regnault Drake Sanders is a serial entrepreneur and EdTech founder based in Atlanta, Georgia. He is the founder of School Economy Inc., a platform that rewards K-12 students for academic achievement with redeemable prizes and incentives. His platform has grown to serve 20,000 active students across multiple cities and has been featured on Fox 5 Atlanta and at Microsoft education events. Connect with Regnault: LinkedIn: linkedin.com/in/regnault-drake-sanders-24797310b Website: schoolconomy.com 🚀 Ready to Make Your Business Official? 👉If you’ll be in Maryland on June 10, 2026, come see Aisha in Columbia, MD:  https://www.eventbrite.com/e/1988791451769?aff=oddtdtcreator  Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence. 👉 Register here: https://www.igotnext.co/training 👉 Grab your FREE Legal Guide at: https://www.smallbizzlegalguide.com 🔗 Stay Connected with Sedgwick Andrews: Follow us across all platforms for legal tips, business strategy, and boss-level motivation: 👉 https://linktr.ee/Sedgwick_Andrews_LC Podcast Mantra: Build the dream messy, build it scared, just don’t build it small. If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

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Ratings & Reviews

5
out of 5
38 Ratings

About

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 maximizing opportunity Perfect for: Entrepreneurs ready to legitimize their side hustles into scalable businesses Small Business Owners (10-250 employees) seeking strategic growth frameworks HR Professionals navigating employment challenges in growing companies Ambitious Leaders who refuse to let limited resources limit their vision Each episode features candid interviews with business owners and operators who have navigated the challenges of growth, overcome obstacles, and achieved extraordinary success. Whether you’re scaling your team, refining your business model, or developing a winning mindset, this podcast provides the inspiration and guidance you need to build with discipline, confidence, and purpose. Your turn is coming. Are you ready? New episodes drop every week because champions don't take days off. Subscribe now and join thousands of entrepreneurs who refuse to wait on the sidelines. Your business growth journey starts here.

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