Explore every episode of the podcast Do Small Business Like a Big Boss Podcast
Dive into the complete episode list for Do Small Business Like a Big Boss Podcast. Each episode is cataloged with detailed descriptions, making it easy to find and explore specific topics. Keep track of all episodes from your favorite podcast and never miss a moment of insightful content.
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Title
Pub. Date
Duration
Stop Drowning in Tasks — How to Delegate Like a Boss with Tanya Thomas
11 Mar 2026
00:35:51
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.
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.
Don’t Be a Boss, Be a Leader — Building Partnerships That Change Lives with Gregory Weiss
25 Feb 2026
00:39:54
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.
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
Why Your Biggest Security Threat Isn’t Hackers – It’s Your Humans
11 Feb 2026
00:37:43
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.
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
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.
The Leadership Skill Nobody Teaches (But Every CEO Needs) | Richard Yep
04 Feb 2026
00:34:56
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.
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
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
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.
Excited and Terrified: The Dual Emotions Every New Leader Must Master
14 Jan 2026
00:37:10
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
🔗 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.
The Importance of Systems and Coaches as a Business Owner with David Girton of LiveNow Fitness
07 Jan 2026
00:49:58
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with David Girton, founder of LiveNow Fitness, to discuss the importance of having systems and coaches in place as a business owner. David shares his journey from working a corporate IT job to becoming a successful fitness coach and entrepreneur. He opens up about the hard lessons learned while transitioning from personal training to running a business and why many entrepreneurs struggle when they don’t treat their business like a real operation.
This conversation highlights the power of mentorship, networking, and understanding your value—along with the role mental health and resilience play in long-term entrepreneurial success.
🎧 What You’ll Learn in This Episode:
Why passion alone isn’t enough to build a successful business
The biggest mistakes entrepreneurs make when they don’t have systems
Why getting a business coach early can save years of frustration
How to transition from being a service provider to a business owner
The importance of knowing your value and standing by it
How networking and coaching accelerate growth
Why mental health and resilience matter in entrepreneurship
Lessons learned from “doing it the hard way”
⏱️ Episode Timestamps:
25:17–25:58 — “We didn’t know how to run a business and learned too many hard lessons”
24:21–24:44 / 23:55 — Extended Clip: Get a business coach
10:04–11:13 — Know your value and stand by it
👤 About the Guest: David Girton is the founder of LiveNow Fitness, a health and fitness business offering bootcamp-style training focused on strength, accountability, and sustainable results. David helps clients and fellow entrepreneurs build discipline, confidence, and structure—both inside and outside the gym.
🚀 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
🔗 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.
From Google Search to Six-Figure Solo Law Firm: Lauren Lester
01 Jan 2026
00:35:14
From Google Search to Six-Figure Solo Law Firm: Lauren Lester's Unconventional Path to Work-Life Balance Podcast: Do Small Business Like a Big Boss
Episode Description: In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Lauren Lester of Lester Law, a solo legal practitioner who built a thriving six-figure law firm in Denver, Colorado—without sacrificing her personal life. Lauren shares her unconventional journey from a surprising Google search that revealed her true career path to launching her own firm straight out of law school, despite being told it couldn’t be done.
Lauren opens up about the pivotal life moment that pushed her to implement radical boundaries in her practice, including her now-famous “no Fridays” rule. She explains how setting firm boundaries not only transformed her work-life balance but also attracted ideal clients who respect her values. The conversation also explores how Lauren leverages legal tech and automation, makes strategic business pivots, and has expanded into coaching other attorneys.
This episode is packed with practical wisdom for small business owners, solo entrepreneurs, and legal professionals who want to build a purpose-driven business without burnout.
🎧 What You’ll Learn in This Episode:
How to uncover your true career path and act on unexpected opportunities
What it really takes to launch a solo law firm and bet on yourself
Why setting strong work-life boundaries can actually attract better clients
How Lauren’s “no Fridays” rule reshaped her business and personal life
Ways to leverage automation and legal technology to increase efficiency
When and how to make strategic pivots as your values evolve
Business resources that support sustainable growth, including Profit First and the StoryBrand framework
⏱️ Episode Timestamps:
15:07-15:25 (Boss)
18:34-19:06 (Boundaries)
30:22-30:32 (Taking the leap)
👤 About the Guest: Lauren Lester is the founder of Lester Law, a solo law firm based in Denver, Colorado. She helps clients through a streamlined, values-driven legal practice and now coaches other attorneys on building sustainable firms with strong boundaries and systems.
🚀 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
🔗 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.
From selling candy on the playground to building and selling multiple seven-figure companies
26 Dec 2025
00:43:09
Episode Title: From Selling Candy on the Playground to Building and Selling Multiple Seven-Figure Companies
Podcast: Do Small Business Like a Big Boss
🎧 Episode Description
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 Cheryl Perez, a seasoned entrepreneur and business coach, to talk about what it truly takes to scale a business from scratch.
Cheryl shares her journey from corporate employee to building and selling multiple seven-figure companies, breaking down the mindset shifts, systems, and resilience required to grow sustainably. 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:
The difference between working IN your business versus ON your business—and why both are required to scale
How to know when it’s time to hire your first team member (even when the numbers feel scary)
Why lead generation systems are the most overlooked investment for new entrepreneurs
How Cheryl uses a six-step meditation practice to make million-dollar decisions without burnout
⏱️ Episode Timestamps:
Guest introduction: Cheryl Perez
06:35 – Knowing when you’re truly “done” with playing small
27:59 – Why capacity limits revenue
38:57 – Stepping into Big Boss energy
👤 About the Guest:
Cheryl Perez is a seasoned entrepreneur and business coach who has built and sold multiple seven-figure companies. Through her coaching and educational services, she helps entrepreneurs transition from corporate careers, build scalable systems, and create freedom-driven businesses rooted in clarity, preparation, and resilience.
🚀 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
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.
Why You Should Do Your Small Business Like a Big Boss!
17 Dec 2025
00:08:21
Podcast: Do Small Business Like a Big Boss
Episode Description:
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, breaks down her journey from the basketball courts of the Bronx to becoming a successful entrepreneur and attorney.
Aisha emphasizes the importance of claiming your space in business, having the right mindset, and treating your business with the seriousness it deserves. This conversation dives into the challenges faced by small business owners and the need for legal and strategic guidance to build a sustainable business. The podcast aims to empower entrepreneurs with real stories, insights, and practical advice to help them grow their businesses confidently.
🎧 What You’ll Learn in This Episode:
Claim your spot in business like you did on the court.
Your mentality is crucial for success in business.
Stop treating your business like a side hustle.
Big businesses have systems; so should you.
You can't build an empire on a shaky foundation.
Real success stories come from perseverance and learning.
Legal guidance is essential for small businesses.
Confidence is key to claiming opportunities.
Think bigger and act with purpose.
Your business journey is unique; embrace it.
⏱️ Episode Timestamps:
[00:00] – Guest introduction: Aisha Massengill
[02:55] – The 'I Got Next' Mentality in Business
[05:50] – Building a Business Like a Big Boss Businesses
👤 About the Guest:
Aisha Massengill is the founder of Sedgwick Andrews Legal & Consulting, LLC.
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.
Hiring Secrets for Startups: What Every Founder Needs to Know
25 Mar 2026
00:27:44
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.
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
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. 🎧
From Military Service to Mission-Driven Business: How Jordie Kern Built 7 Eagle Group
22 Apr 2026
00:45:08
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.
🚀 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
From Teacher to Tech CEO: How Stephen Spence Built a Software Company With No Startup Background
08 Apr 2026
00:36:42
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.
🔗 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.
From Groupon Deals to Multiple Business Lines: How One Spa Owner Built Tocar From a Single Room
01 Apr 2026
00:47:20
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.
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.
How Joy L. King Built Two Businesses on Intuition + Referrals (While in a Chief Role)
06 May 2026
00:42:24
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.
🚀 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.
Stop Guessing, Start Growing: Marketing Strategy for Small Business
13 May 2026
00:40:51
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: 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
🔗 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.
The Bootstrapped EdTech Playbook: Offshore Teams, DIY PR, and 20K Users
20 May 2026
00:29:55
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.
🔗 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.
If You Don't Have a Client Plan, You Have a Time Bomb
27 May 2026
00:33:48
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.
🚀 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.