Do Small Business Like a Big Boss Podcast

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 VIP Why culture isn't your website's mission statement — it's the worst behavior you're willing to tolerate — and how to set that standard early How 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.

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.

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 first How to view hiring as an investment instead of an expense Why Outsource Access serves businesses across 85 industries instead of specializing in one niche The key performance indicators Brad uses to measure outsourcing success How 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.

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-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. 🎧

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. 🎧

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.

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 framework Why relying only on referrals can become a major business risk How to identify skill gaps and decide whether to learn, hire, or outsource What it’s like building and running a business with your spouse What a fractional CTO does and how it helps growing businesses scale strategically ⏱️ Episode Timestamps : 00:14 – Welcome & guest introduction 00:35 – David’s origin story and launching 4V Services 04:06 – The 4-category framework for evaluating business ideas 08:56 – Landing early clients through referrals 10:21 – Understanding the MarkLogic niche 11:37 – Why referrals alone are a “time bomb” 16:17 – Scaling back and lessons on focus 18:40 – Strategic hiring and organic growth 22:28 – The challenge of training clients too well 24:35 – Balancing big clients and smaller accounts 26:04 – Running a business with your spouse 29:44 – The shift into fractional CTO services 36:28 – Advice David would give his younger self 38:01 – 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.

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 partners Why non-technical founders need a technical ally How AI tools like Zapier and N8N streamline operations How major partnerships and relationships drive growth Building 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.

In this episode of Do Small Business Like a Big Boss , host Aisha Jorge Massengill sits down with George Ennis, founder of EAG Advertising, to talk about how small businesses can stop wasting money on marketing that doesn’t work and start building strategies that actually drive growth. This conversation breaks down the biggest mistakes business owners make online, how to maximize a limited marketing budget, and why relationships—not just ad spend—are the real key to long-term business success. 🎧 What You’ll Learn in This Episode : How to audit your digital footprint and uncover hidden marketing issues The right way to calculate and prioritize your marketing budget Why pay-per-click advertising may not be the best move for small businesses The “presearch” method for building authentic LinkedIn relationships How small businesses can compete with bigger brands strategically ⏱️ Episode Timestamps : 00:01 – Welcome and guest introduction 00:52 – Twin dad life and George’s personal journey 01:53 – From corporate America to entrepreneurship 03:07 – Launching EAG Advertising 06:18 – The importance of niching down 08:59 – Building relationships that drive business 12:04 – LinkedIn outreach and the “presearch” strategy 15:54 – Common digital marketing mistakes 19:06 – Competing with big brands on a small budget 24:04 – Why websites still matter 28:37 – Growing and leading a team 33:20 – Work-life balance as an entrepreneur 37:49 – What “Do Small Business Like a Big Boss” means to George 41:20 – Where to connect with George and EAG Advertising 👤 About the Guest : George Ennis is the Founder of EAG Advertising, a full-service marketing and advertising agency specializing in B2B, nonprofit, and complex industries. With more than 20 years of strategic agency experience, George helps small and mid-sized businesses create marketing strategies with big-business impact. Connect with George: LinkedIn: E.A.G. Advertising Website: eagadvertising.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 🔗 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.

In this episode of Do Small Business Like a Big Boss , host Aisha Jorge Massengill sits down with Joy L. King, founder of Lifestyles by Joy and Sweet Life Business Coaching, to talk about building intuitive, referral-based businesses while balancing a high-level executive role. This conversation covers the real-life lessons behind starting messy, trusting your instincts, and creating a business rooted in relationships—what worked, what didn’t, and what every aspiring entrepreneur needs to hear. 🎧 What You’ll Learn in This Episode : How to stop chasing money and start building through relationships The “repeatable value” concept every founder must define before scaling How to protect and maintain your business while stepping into a corporate role Why mindset and self-worth are the biggest blockers to growth What to focus on in your first 30 days before investing in branding or assets ⏱️ Episode Timestamps : 00:00 – Introduction 00:46 – Guest introduction: Joy L. King 02:05 – Launching during the pandemic 06:29 – Turning design into therapy and purpose 09:21 – Building through referrals 11:42 – “All money ain’t good money” 17:34 – When chasing money backfires 24:14 – Tools and systems Joy uses 27:00 – Negotiating an executive role while keeping her businesses 33:31 – The #1 mindset block 38:15 – The first 30 days as a founder 44:14 – What “Big Boss” means 👤 About the Guest : Joy L. King is a lifestyle architect, business coach, and executive. She is the founder of Lifestyles by Joy, a referral-based interior design firm, and Sweet Life Business Coaching, where she helps entrepreneurs define repeatable value and scale with intention. She also serves as a Chief at NCAN (National College Attainment Network), leading strategy and operations. 🔗 Connect with Joy: lifestylesbyjoy.com sweetlifebusinesscoaching.com LinkedIn — linkedin.com/in/joyking912 🚀 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 🔗 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.

In this episode of Do Small Business Like a Big Boss , host Aisha Jorge Massengill sits down with Jordie Kern, founder of 7 Eagle Group, to explore what it really takes to build and rebuild businesses from the ground up—seven times over. Jordie shares his 35-year entrepreneurial journey, the mindset behind mission-driven business, and how a simple one-minute video is transforming how military veterans connect with meaningful careers. This conversation dives deep into resilience, purpose, and practical business strategy, especially for founders building with limited resources but big vision. 🎧 What You’ll Learn in This Episode : How Jordie turned a mission to serve veterans into a 30-person recruiting company What the SkillBridge program is and how it supports both veterans and employers Why the traditional resume model is becoming outdated The most important hire to make when scaling a business How to think about funding without giving up equity Morning routines and time-blocking strategies from a serial entrepreneur Why your first business should be designed to fail safely and teach quickly ⏱️ Episode Timestamps : 00:04 – Welcome & intro to Jordie Kern and 7 Eagle Group 00:49 – Growing up as the son of a WWII Army veteran 04:21 – Early entrepreneurial ventures and working with the Clemente family 07:23 – The moment Jordie started 7 Eagle Group 10:06 – The reality of building the business from scratch 12:48 – How the SkillBridge program works 23:50 – The one-minute veteran video and why it works 30:15 – Scaling a remote team of 30+ 34:50 – Bootstrapping vs. investors 36:35 – Systems, delegation, and protecting your genius zone 43:50 – Advice for mission-driven entrepreneurs 46:42 – What “Do Small Business Like a Big Boss” means to Jordie 👤 About the Guest : Jordie Kern is the founder of 7 Eagle Group, a mission-driven talent platform based in Amherst, Massachusetts that connects military veterans and transitioning service members with meaningful civilian careers. With over 35 years of entrepreneurship experience and seven businesses built, Jordie has grown 7 Eagle Group into a fully remote team serving 125+ SkillBridge participants daily through its career academy. The company partners with major organizations including Amazon, the Kansas City Chiefs, American Airlines, and Jack Daniel’s. Connect with Jordie: Website: 7eagle.com Email: jk@7eagle.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

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 Boss” means to Stephen 38:30 – Where to find Stephen 👤 About the Guest : Stephen Spence is the Managing Director and Co-Owner of Project MAPIT, an all-in-one mapping, reputation, and sales platform for contractors in the home services industry. A former special education teacher and coach, Stephen transitioned into entrepreneurship in his 40s and helped scale Project MAPIT into a competitive software company serving hundreds of clients. Connect with Stephen: Website: projectmapit.com LinkedIn: Stephen Spence 🚀 Ready to Make Your Business Official? Join Aisha’s FREE weekly webinar, Make Your Business Official , and learn how to build, brand, and bulletproof 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.

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 Stephen Conti, Founder and CEO of Tocar Spa, Tocar Sport, and Tocar Corporate Wellness. Stephen shares the remarkable story of how he went from running a small spa with Groupon deals to managing a multi-division wellness business in Howard County, Maryland. He reveals the real-life challenges, wins, and valuable lessons from his entrepreneurial journey, offering insights every aspiring entrepreneur can learn from. 🎧 What You’ll Learn in This Episode: How Stephen transitioned from a marketing career to owning a thriving wellness business The ups and downs of using Groupon as a launch strategy and what he would do differently The importance of word-of-mouth referrals and leveraging networking through the Chamber of Commerce How the Goldman Sachs 10,000 Small Businesses program helped accelerate his growth The importance of hiring for cultural fit in a service-based business How to scale a business without losing loyal clients, including transitioning them to other providers ⏱️ Episode Timestamps: 00:00 – Introduction 01:27 – Stephen’s life before Tocar Spa 07:17 – The side hustle: working at a massage franchise 09:27 – Early days of Tocar: no systems, just Groupon 11:20 – Networking: word-of-mouth & social media 14:47 – SCORE, Goldman Sachs, and finding the right CPA 17:18 – Funding the business and bootstrapping 18:35 – Identifying the revenue ceiling and scaling 20:27 – Hiring for culture fit 23:45 – Transitioning clients and leadership layers 32:40 – AI & robotic massage tech 40:35 – Advice to his younger self 45:14 – What Do Small Business Like a Big Boss means to Stephen 👤 About the Guest: Stephen Conti is the Founder and CEO of Tocar Spa, Tocar Sport, and the newly launched Tocar Corporate Wellness, all located in the Columbia, Maryland area. Starting from a single treatment room and Groupon deals, Stephen has grown Tocar into a multi-division wellness company with 20+ team members across three business lines. He is also the creator of the Healing for Healers program, which provides free massages to caregivers of individuals with Alzheimer's, Parkinson's, and dementia. Connect with Stephen: Website: www.tocarspa.com Location: 10630 Little Patuxent Parkway, Columbia, MD (by the mall) | Appointment only 🚀 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: Make Your Business Official 👉 Grab your FREE Legal Guide at: Sedgwick Andrews Legal & Consulting 🔗 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.

In this episode of Do Small Business Like a Big Boss , host Aisha Massengill , Founder of Sedgwick Andrews Legal & Consulting, LLC , sits down with Bala Vishwanath , Founder and CEO of Novo Guild , to break down what it really takes to hire the right people in a startup. Bala shares lessons from decades in entrepreneurship—from early startup failures to building a high-demand recruiting firm serving venture-backed companies. They discuss why hiring is harder than most founders expect, what makes a great early-stage hire, and how Lean principles and systems can improve hiring outcomes without losing the human element. This conversation also explores the growing importance of go-to-market (GTM) talent and how immigration trends are impacting today’s tech talent pipeline. 🎧 What You’ll Learn in This Episode: Why hiring is harder than most founders expect—and why great hires still fail What GTM talent is and why it’s critical for early-stage startups How to apply Lean principles and structured systems to hiring The key traits that predict success in startup environments How immigration trends are shaping the tech talent market ⏱️ Episode Timestamps: 00:00 – Introduction & Novo Guild overview 01:08 – What GTM talent means 03:53 – Scaling a nonprofit globally 06:02 – From platform idea to recruiting firm 07:34 – Why hiring is harder than expected 10:46 – Building credibility with clients 12:20 – Applying Lean principles to hiring 17:29 – Using the scientific method in hiring 19:03 – Traits of successful startup hires 21:06 – Immigration and talent supply 23:04 – Work-life balance as a founder 24:13 – What “Big Boss” means to Bala 🎤 About the Guest: Bala Vishwanath is the Founder and CEO of Novo Guild , a talent firm helping venture-backed startups hire top engineering and go-to-market talent across the US and India. He previously founded United Prosperity , a nonprofit supporting small businesses through crowdsourced loan guarantees. Connect with Bala Vishwanath: Website: https://novoguild.com Email: bala@novoguild.com LinkedIn: Search “Bala Vishwanath” 🚀 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. 👉 https://www.igotnext.co/training 👉 Grab your FREE Legal Guide : https://www.topemployermistakes.com 🔗 Stay Connected with Sedgwick Andrews 👉 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, subscribe, download, and share it with another boss who needs to hear it. 🎧

In this episode of Do Small Business Like a Big Boss , host Aisha Jorge Massengill , Founder of Sedgwick Andrews Legal & Consulting, LLC , sits down with Tonya Thomas , founder of Team Delegate , to discuss the entrepreneurial journey and the crucial skill of delegation. Tonya shares her experiences transitioning from a solo entrepreneur to leading a successful virtual assistant agency. The conversation touches on the challenges of scaling a business, building trust with clients, and identifying when to hire a virtual assistant (VA) to manage overwhelm. They also discuss the tools and systems that can streamline task management and the value of working with US-based virtual assistants. 🎧 What You’ll Learn in This Episode: Delegation is a learned skill —and it’s essential for business growth. Building trust with clients and VAs is key to a successful working relationship. How to know when it’s time to hire a virtual assistant to avoid burnout. Tools for effective task management and how they help in scaling a business. The importance of US-based virtual assistants and why they are a valuable asset to businesses. ⏱️ Episode Timestamps: 00:00 – The entrepreneurial journey begins 03:10 – Navigating the early days of business 05:54 – Building Team Delegate: From solo to agency 09:05 – Transitioning from working in to working on 11:52 – Delegation: The art of letting go 15:08 – Identifying when to hire a virtual assistant 18:03 – Overcoming control issues in delegation 20:57 – Tools for effective task management 23:54 – Onboarding and building relationships with VAs 27:06 – Learning from mistakes and growing 30:01 – The value of US-based virtual assistants 32:57 – Finding fulfillment in helping others 35:58 – Staying grounded in entrepreneurship 💡 Key Takeaways: "Delegation is a skill set." "Communication is key." "Learn from your failures." "Identify when to hire a VA to manage overwhelm." "Trust is the foundation of client-VA relationships." 🎤 About Our Guest: Tonya Thomas is the founder of Team Delegate , a virtual assistant agency offering US-based VAs to help businesses scale. Tonya’s entrepreneurial journey began in the early 2000s, and she now leads a growing agency focused on effective delegation, building trust, and supporting business owners as they grow their teams. Connect with Tonya Thomas: Website: teamdelegate.com LinkedIn: linkedin.com/in/tonyathomas 🔗 Stay Connected with Sedgwick Andrews Follow us 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 with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss , host Aisha Massengill , Founder of Sedgwick Andrews Legal & Consulting, LLC , interviews Gregory Weiss , Managing Partner of Action Staffing Group . Gregory shares insights into leadership, hiring, and how the staffing industry is about changing lives—not just filling positions. They discuss the challenges of navigating COVID-19, the costs of bad hires, and why human connection is irreplaceable in business, even in the age of AI. Gregory highlights how building meaningful partnerships and leading with heart are keys to success. 🎧 What You’ll Learn in This Episode: Staffing isn’t just about filling positions —it’s about changing lives. Why titles don’t matter —team success is what drives business. The true cost of a bad hire and how to avoid it. Why AI can’t replace human-to-human connection in business. Leadership vs. Bossing : What makes a great leader. ⏱️ Episode Timestamps: 00:00 – Introduction to Action Staffing Group 01:37 – The importance of partnerships in staffing 05:06 – Transitioning roles: From CEO to Managing Partner 06:20 – Navigating COVID-19 07:45 – Common hiring mistakes for small businesses 10:03 – Building client relationships 13:31 – The role of AI in recruitment 16:55 – Managing chaos in staffing 19:41 – The human element in business decisions 23:19 – Staying focused amidst competition 26:23 – Personal motivation and accountability 29:16 – The importance of listening in business 34:50 – Leadership vs. Bossing: A Philosophy 💡 Takeaways: "We are in the business of helping people change their lives for the better." "Titles don’t mean a thing; it’s about the success of the company." "Just pick up the phone and talk to people—that’s how partnerships are built." "Sell with your ears, not your mouth." "Don’t be a boss, be a leader." "AI is hurting businesses because you’re losing human-to-human interaction." 🎤 About Our Guest: Gregory Weiss is the Managing Partner of Action Staffing Group , a staffing firm focused on changing lives through meaningful employment. Gregory believes in leadership built on accountability, relationships, and understanding that people—not positions—are at the heart of every business. Connect with Gregory: LinkedIn: linkedin.com/in/gregory-weiss-2591a935 Website: actionstaffing-group.com 🚀 Ready to Make Your Business Official? Join Aisha Massengill for her FREE weekly webinar , Make Your Business Official , where she helps small business owners navigate the legal steps to build a legit, protected, and profitable business. 👉 Register here: Make Your Business Official 🔗 Stay Connected with Sedgwick Andrews For legal tips and business strategies, follow us here: 👉 https://linktr.ee/Sedgwick_Andrews_LC

In this episode of Do Small Business Like a Big Boss , host Aisha Jorge Massengill , Founder of Sedgwick Andrews Legal & Consulting, LLC , sits down with Carter Schoenberg , Chief Cybersecurity Officer at SoundWay Consulting, Inc. , to discuss the human side of cybersecurity—why it’s the biggest threat and how small businesses can protect themselves. Carter brings decades of cybersecurity experience, sharing insights into the human element’s role in organizational security. He also discusses the impact of AI on cybersecurity, the importance of HR and IT collaboration, and why cybersecurity is not just for big companies but for small businesses too. This conversation highlights real-world lessons every entrepreneur needs to hear to ensure their business stays secure in today’s digital world. 🎧 What You’ll Learn in This Episode: Cybersecurity is essential for businesses of all sizes : Understand why even small businesses are targets. The human element is the weakest link : Why employees must be educated and involved in protecting sensitive data. Best practices for employee onboarding and offboarding : Protect your business during employee transitions. The impact of AI on cybersecurity : How artificial intelligence is reshaping the security landscape. Balancing security with business growth : How to ensure security doesn't slow down your momentum. ⏱️ Episode Timestamps: 00:00 – “The human is the weakest link” – Opening discussion on the human factor in cybersecurity 04:55 – The importance of cybersecurity for small businesses 12:04 – The human element in cybersecurity 20:06 – Best practices for employee offboarding 25:04 – Balancing security with growth 34:00 – The impact of AI on cybersecurity 38:59 – Final thoughts on small business success 👤 About the Guest: Carter Schoenberg is the Chief Cybersecurity Officer at SoundWay Consulting, Inc. , with decades of experience in cybersecurity and risk management. Carter focuses on the critical role of human behavior in securing digital infrastructures for businesses of all sizes. Connect with Carter Schoenberg: LinkedIn: linkedin.com/in/carter-schoenberg-5122011 Website: soundwayconsulting.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: Make Your Business Official 👉 Grab your FREE Legal Guide at: Sedgwick Andrews Legal & Consulting - Where Value and Experience Intersect 🔗 Stay Connected with Sedgwick Andrews Follow us 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, subscribe, download, and share with another boss who needs to hear it.

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 – Pivots and new ventures 29:24 – Advice for entrepreneurs 32:36 – Conclusion and resources 👤 About the Guest: Richard Yep is the Vice President of Vetted Solutions , bringing decades of leadership experience from nonprofit organizations and executive search. He specializes in helping organizations navigate leadership transitions, build inclusive cultures, and make strategic decisions that align with core values. Connect with Richard Yep: LinkedIn: https://linkedin.com/in/richardyep 🚀 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 🔗 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

In this episode of Do Small Business Like a Big Boss , host Aisha Massengill , Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC , sits down with Nancy Belle Hansford , Founder of Watkinsville Wine , to talk about how she turned a passion discovered at 19 into a thriving winery business. Nancy shares her inspiring journey from making wine in her parents’ house during the COVID quarantine to founding a federally licensed farm winery. She talks about navigating complex alcohol regulations, turning wine-making failures into new product lines, and balancing a full-time job with running a 24/7 passion. This conversation is a masterclass on how to start small, think big, and build a business that funds your passion without burning you out. 🎧 What You’ll Learn in This Episode: Starting Young and Asking for Help : How Nancy learned to make wine with zero formal training, and why attending a dry college helped her business Navigating Legal and Regulatory Challenges : Decoding federal alcohol licensing and finding loopholes to launch a winery in a dry county Turning Mistakes Into Revenue Streams : How Nancy’s early wine failures led to profitable new product lines Building a Sustainable Business Model : How Nancy scaled her winery while keeping her passion and paycheck separate to prevent burnout Balancing Full-Time Work with a 24/7 Passion : Setting boundaries and making use of simple tools to manage both business and full-time work Redefining Success on Your Own Terms : Why Nancy defines success as loving what you do—and not just making money ⏱️ Episode Timestamps: 00:00 – Introduction 03:23–03:58 – How Nancy learned to make wine with no formal background 10:01–10:28 – Cold-calling government officials to get wine-making approval 25:10–25:45 – How mistakes became new revenue streams, like pineapple-grapefruit wine 48:22 – Wrap-up & Calls to Action 👤 About the Guest: Nancy Belle Hansford is the founder of Watkinsville Wine , a federally licensed farm winery. Starting her wine-making journey at just 19 during the COVID quarantine, Nancy has since grown her business while working full-time as a project manager in tech. She is passionate about creating quality wines, navigating complex legalities, and building a business that allows her to follow her passion without sacrificing her well-being. 🚀 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 🔗 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.

In this episode of Do Small Business Like a Big Boss , host Aisha Jorge Massengill sits down with Karen Murphy, President of FBM Integrated Marketing, to discuss her journey from employee to owner of a 35-year-old B2B marketing agency. Karen shares what it’s really like stepping into leadership—feeling both excited and terrified—while navigating mentorship, remote work, and high-level decision-making. This conversation dives into building strong processes, simplifying complex marketing challenges, maintaining work-life balance, and leading with confidence in a women-owned business. 🎧 What You’ll Learn in This Episode : You don’t have to start from scratch to build something extraordinary Why leadership often feels both exciting and terrifying The power of mentorship in personal and professional growth How remote work has changed collaboration and leadership Why strong processes are essential for managing complex projects How to achieve work-life balance through trust and flexibility The value of women-owned business certifications Why a research-minded approach leads to better client outcomes How to simplify complex marketing challenges Advice for aspiring leaders facing tough decisions ⏱️ Episode Timestamps : 5:40-6:07– The importance of mentorship in leadership 23:02 - 25:15 – Research-minded approach to client work 34:07-34:34 – Doing small business like a big boss 👤 About the Guest : Karen Murphy is the President of FBM Integrated Marketing, a B2B marketing and branding agency. She leads with a research-driven mindset, a passion for mentorship, and a commitment to simplifying complex marketing challenges for clients. 🚀 Ready to Make Your Business Official? Join Aisha’s FREE weekly webinar, Make Your Business Official , and learn how to build, brand, and bulletproof with confidence. 👉 Register here: https://www.igotnext.co/training 👉 Grab your FREE Legal Guide at : https://www.topemployermistakes.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.