Do Small Business Like a Big Boss Podcast

Aisha Massengill
  • 5.0 (8)
  • 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. 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.

    34 min

  2. 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.

    30 min

  3. May 13

    Stop Guessing, Start Growing: Marketing Strategy for Small Business

    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 issuesThe right way to calculate and prioritize your marketing budgetWhy pay-per-click advertising may not be the best move for small businessesThe “presearch” method for building authentic LinkedIn relationshipsHow small businesses can compete with bigger brands strategically ⏱️ Episode Timestamps: 00:01 – Welcome and guest introduction00:52 – Twin dad life and George’s personal journey01:53 – From corporate America to entrepreneurship03:07 – Launching EAG Advertising06:18 – The importance of niching down08:59 – Building relationships that drive business12:04 – LinkedIn outreach and the “presearch” strategy15:54 – Common digital marketing mistakes19:06 – Competing with big brands on a small budget24:04 – Why websites still matter28:37 – Growing and leading a team33:20 – Work-life balance as an entrepreneur37:49 – What “Do Small Business Like a Big Boss” means to George41:20 – 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.

    41 min

  4. May 6

    How Joy L. King Built Two Businesses on Intuition + Referrals (While in a Chief Role)

    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 relationshipsThe “repeatable value” concept every founder must define before scalingHow to protect and maintain your business while stepping into a corporate roleWhy mindset and self-worth are the biggest blockers to growthWhat to focus on in your first 30 days before investing in branding or assets ⏱️ Episode Timestamps: 00:00 – Introduction00:46 – Guest introduction: Joy L. King02:05 – Launching during the pandemic06:29 – Turning design into therapy and purpose09:21 – Building through referrals11:42 – “All money ain’t good money”17:34 – When chasing money backfires24:14 – Tools and systems Joy uses27:00 – Negotiating an executive role while keeping her businesses33:31 – The #1 mindset block38:15 – The first 30 days as a founder44:14 – 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.

    42 min

  5. Apr 22

    From Military Service to Mission-Driven Business: How Jordie Kern Built 7 Eagle Group

    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 companyWhat the SkillBridge program is and how it supports both veterans and employersWhy the traditional resume model is becoming outdatedThe most important hire to make when scaling a businessHow to think about funding without giving up equityMorning routines and time-blocking strategies from a serial entrepreneurWhy your first business should be designed to fail safely and teach quickly ⏱️ Episode Timestamps: 00:04 – Welcome & intro to Jordie Kern and 7 Eagle Group00:49 – Growing up as the son of a WWII Army veteran04:21 – Early entrepreneurial ventures and working with the Clemente family07:23 – The moment Jordie started 7 Eagle Group10:06 – The reality of building the business from scratch12:48 – How the SkillBridge program works23:50 – The one-minute veteran video and why it works30:15 – Scaling a remote team of 30+34:50 – Bootstrapping vs. investors36:35 – Systems, delegation, and protecting your genius zone43:50 – Advice for mission-driven entrepreneurs46:42 – 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

    45 min

  6. Apr 8

    From Teacher to Tech CEO: How Stephen Spence Built a Software Company With No Startup Background

    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 lineWhy cold outreach often fails—and what actually works for lead generationHow radical transparency builds trust and drives revenueWhy you should master roles before delegating themWhat EBITDA is and why it matters for long-term business valueHow systems, tools, and AI support growth in modern businessesThe mindset needed to handle rejection and stay in the game ⏱️ Episode Timestamps: 00:25 – Welcome & What is Project MAPIT02:47 – From teacher to tech startup: Stephen's origin story04:30 – When the founder left and Stephen stayed in the fight07:24 – The family decision and support system10:50 – Wearing every hat in the early years13:30 – Lead generation: what worked and what didn’t16:05 – Handling rejection in sales18:00 – Learning roles before delegating21:34 – Buying out a founder23:53 – Understanding EBITDA25:45 – Systems, tools, and AI31:30 – AI in small business33:06 – Advice for entrepreneurs36:35 – 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.

    37 min

  7. Apr 1

    From Groupon Deals to Multiple Business Lines: How One Spa Owner Built Tocar From a Single Room

    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.

    47 min

  8. Mar 25

    Hiring Secrets for Startups: What Every Founder Needs to Know

    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 failWhat GTM talent is and why it’s critical for early-stage startupsHow to apply Lean principles and structured systems to hiringThe key traits that predict success in startup environmentsHow immigration trends are shaping the tech talent market ⏱️ Episode Timestamps:00:00 – Introduction & Novo Guild overview01:08 – What GTM talent means03:53 – Scaling a nonprofit globally06:02 – From platform idea to recruiting firm07:34 – Why hiring is harder than expected10:46 – Building credibility with clients12:20 – Applying Lean principles to hiring17:29 – Using the scientific method in hiring19:03 – Traits of successful startup hires21:06 – Immigration and talent supply23:04 – Work-life balance as a founder24:13 – 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 MantraBuild 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. 🎧

    28 min
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Ratings & Reviews

5
out of 5
8 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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