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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Why Digital Literacy Is the New Small Business Skill | Do Small Business like a Big Boss
Wednesday, July 29, 2026 • Duration 47:10
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.
Build the dream messy, build it scared, just don't build it small.
From Corporate Dropout to 6-Figure CEO: How Shan Thomas Built on Her Own Terms
Wednesday, July 22, 2026 • Duration 42:50
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
How to Know When to Outsource
Wednesday, July 15, 2026 • Duration 54:13
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.
Outsmarting the Big Guys: Building a Challenger Brand Agency from Scratch
Thursday, July 9, 2026 • Duration 37:23
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.
From Engineering to Landscaping COO: Recurring Revenue, Smart Hiring & Systems That Scale
Wednesday, July 1, 2026 • Duration 29:04
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
Building Six-Figures Organically: Social Media, Government Contracts & Community
Wednesday, June 24, 2026 • Duration 47:36
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
If You Don't Have a Client Plan, You Have a Time Bomb
Wednesday, May 27, 2026 • Duration 33:48
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.
The Bootstrapped EdTech Playbook: Offshore Teams, DIY PR, and 20K Users
Wednesday, May 20, 2026 • Duration 29:55
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.
Stop Guessing, Start Growing: Marketing Strategy for Small Business
Wednesday, May 13, 2026 • Duration 40:51
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:
How Joy L. King Built Two Businesses on Intuition + Referrals (While in a Chief Role)
Wednesday, May 6, 2026 • Duration 42:24
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:LinkedIn —
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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
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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.
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. 🎧
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.
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. 🎧
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.
🚀 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.
🔗 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.
🔗 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.
🚀 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
🔗 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.
🚀 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.
🔗 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.
