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Don't Play Small: Brand Voice and Confidence for Founders | Do Small Business like a Big Boss
Learn how to find a brand voice that sounds like you, and how to ride the ups and downs of business ownership without panic.
Becky Freemal spent 25 years as an Emmy Award-winning broadcast journalist before launching Market Exec, a fractional CMO firm that helps founders and leadership teams turn their brand voice into measurable growth. Four years in, she shares what the first scary stretch felt like, where she chose to invest early, and why slow seasons no longer mean "the year of ramen." You'll also hear her simple brand voice test, how to use your own social media data to find your audience, and how she approaches sales calls without feeling salesy.
💡 WHAT YOU'LL LEARN
• How to ride the entrepreneur roller coaster, from "the year of ramen" to a slow summer that included a trip out west
• Where Becky invested early (writing her book and joining a fractional CMO accelerator) and how she judged the return
• A three-part brand voice test: simple, genuine and consistent
• How to find your audience in the data on who already follows you on social media
• A money habit for tax time: keep a separate account for taxes
• How to sell without feeling salesy by leading with your purpose
⏱️ EPISODE TIMESTAMPS
00:00 – Meet Becky Freemal, Emmy-winning journalist turned fractional CMO
02:10 – Why Becky left a 25-year broadcast journalism career
04:01 – Fear, excitement and leaving a safe job
05:02 – The entrepreneur roller coaster: from the year of ramen to a trip out west
08:37 – First months of Market Exec: systems and smart investing
13:54 – Building credibility when you change careers
18:45 – Do you have to prove you belong? Fake the confidence
23:04 – The hardest part: taxes, risk and never letting one person define you
27:09 – Green and growing: why lifelong learning matters
27:47 – A brand habit for solo founders: lead with your purpose
30:36 – How to find your brand voice: simple, genuine, consistent
34:39 – Protecting your time: morning yoga and meditation
37:12 – What Do Small Business Like a Big Boss means: don't play small
38:14 – Final advice: who are you doing all of this for?
🎤 ABOUT OUR GUEST
Becky Freemal is an Emmy Award-winning broadcast journalist with 25 years in news, the founder of Market Exec, a fractional CMO firm, and the author of Brand Voice: People plus Data Drive Results. She also teaches as an adjunct at Virginia Tech.
Connect with Becky:
beckyfreemal.com
linkedin.com/in/beckyfreemal
👉 Stay connected with Sedgwick Andrews: https://linktr.ee/Sedgwick_Andrews_LC
https://smallbizzlegalguide.com
https://TopBillingTrademarks.com
🎙️ Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it.
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PR for Small Business: Why Hyperlocal Beats Forbes
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Nicole Blake Baxter, founder of The Blake Agency, to discuss how small businesses can use public relations (PR) to build visibility, credibility, and stronger audience connections.
With over 20 years of experience, Nicole shares how to create an effective PR strategy without a big budget, why local media coverage matters, and how entrepreneurs can build their digital presence.
🎧 What You’ll Learn:
The difference between PR and marketingWhy local media coverage can be valuableHow to approach sales through storytellingHow to pitch articles to trade publicationsHow earned, paid, and owned media work togetherHow to start building your PR strategy⏱️ Episode Timestamps:
00:43 – Introducing Nicole Blake Baxter
00:46 – PR vs. marketing
03:00 – Her music industry experience
07:29 – Starting her own agency
13:48 – Business partnerships and exit plans
18:50 – Landing her first clients
20:07 – Storytelling and sales
26:52 – Why she turns down short-term campaigns
28:31 – Local press vs. Forbes
33:01 – Building your digital footprint
34:47 – Pitching trade publications
39:50 – Getting started with PR
40:42 – Earned, paid, and owned media
44:50 – Finding The Blake Agency
👤 About the Guest:
Nicole Blake Baxter is the founder and managing director of The Blake Agency, an Atlanta-based public relations firm serving clients nationwide. She has over 20 years of PR experience, beginning her career at Island Def Jam before launching her own agency.
🚀 Make Your Business Official!
Join Aisha’s FREE weekly webinar to learn how to build, brand, and strengthen your business.
👉 Register: https://www.igotnext.co/training
👉 Get Your FREE Legal Guide:
https://smallbizzlegalguide.com
🔗 Stay Connected with Sedgwick Andrews:
https://linktr.ee/Sedgwick_Andrews_LC
Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
If you enjoyed this episode, subscribe, download, and share it with another business owner! 🎧
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The $300K Mistake That Taught Him You Can’t Buy Trust
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Marcus Smith, CEO of Cloud Trailz, a Salesforce support, management, and strategy firm, to talk about the systems and strategies that helped him build and grow a successful business.
This conversation covers the real-life lessons behind building a subscription-based business, protecting your company from overreliance on a single referral channel, creating owned content and SEO strategies, and the $300,000 mistake that taught Marcus a powerful lesson: you cannot buy trust from strangers.
🎧 What You’ll Learn in This Episode:
Why a subscription model can create more stability than relying on one-off projectsHow to protect your business from depending on a single referral or acquisition channelWhy owning your content and search traffic can create long-term growthHow “Demo Week” helps improve the quality and speed of your team's workThe $300K lesson on why trust cannot be bought from strangers⏱️ Episode Timestamps:
00:19 – Introduction00:59 – Guest introduction: Marcus Smith & Cloud Trailz01:54 – Why he built the business on subscriptions, not projects04:00 – How COVID fueled early growth and the risk that came with it08:05 – Insulating the business from a single dominant channel08:48 – Why they invest in owned content instead of renting attention09:16 – SEO explained simply: matching intent to content11:12 – The 3% buying vs. 95% browsing framework12:29 – The corporate moment that made him want out15:11 – How a joke turned him into a CEO16:30 – Handling pushback on the subscription model19:53 – The early hurdle: realizing nobody cares about your new business22:34 – How to actually get customers to care24:48 – A client transformation he's most proud of29:11 – The “Demo Week” structure that changed everything35:23 – The $300K mistake: trying to buy back demand37:49 – Why “systems beat heroics”40:23 – What “Do Small Business Like a Big Boss” means to Marcus41:28 – Where to connect with Cloud Trailz👤 About the Guest:
Marcus Smith is the CEO of Cloud Trailz, a Salesforce support, management, and strategy firm headquartered in Atlanta, Georgia. The company has helped more than 250 businesses put Salesforce to work for their teams.
Website: https://www.cloudtrailz.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. 🎧
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The No-Code Playbook for First-Time Founders
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 Dan Hafner, founder of Dapper No Code, to talk about building a successful software business without learning to code or hiring a traditional development team.
Dan shares his journey from farm kid to software founder, how he discovered the power of no-code tools, and the mindset shifts that helped him turn his skills into a profitable business. He also explains why he intentionally downsized his team, how AI helps him run a high-output firm, and what first-time founders really need to build a business.
🎧 What You’ll Learn in This Episode:
How to turn an app idea into a sellable product using no-code tools
Why knowing your financial “bottom number” matters before going full-time
The three things every business needs: a way to sell, get paid, and reach people
Why growing a team isn't always the goal and how AI can help you stay lean
How to audit your tech stack and eliminate unnecessary subscriptions
⏱️ Episode Timestamps:
00:39 – Introduction & Guest Introduction: Dan Hafner
01:02 – From farm kid to software founder
02:52 – Dan's first job and early career lessons
04:44 – Landing a QA role at Deloitte
08:07 – Discovering his passion for computer work
11:59 – Deciding to become a business owner
14:16 – Discovering no-code app builders
16:50 – Making the business official
19:07 – The moment it became a real business
20:30 – Quitting his job for good
23:29 – Advice for entrepreneurs afraid of the timing
27:24 – Pricing, confidence, and knowing your worth
29:14 – Growing a team to seven and shrinking back to one
32:02 – AI and no-code tools transforming the business
41:11 – Auditing your tech stack
46:06 – What “Do Small Business Like a Big Boss” means to Dan
47:31 – Where to find Dan and The No Code Advantage podcast
👤 About the Guest:
Dan Hafner is the founder of Dapper No Code, a Pittsburgh-based no-code app and software development firm that helps coaches, experts, and small business owners turn software ideas into revenue-generating products without traditional development costs.
Dapper No Code was recognized as Best of No-Code Development in the USA for 2025. Dan also hosts The No Code Advantage podcast.
Connect with Dan:
Website: https://www.dappernocode.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.
Link to episode
Why Digital Literacy Is the New Small Business Skill | Do Small Business like a Big Boss
Thinking about turning your side project into a nonprofit or small business? Ian Kimble breaks down exactly what to lock in early — starting with the two moves most founders put off too long.
Ian Kimble is the co-founder and executive director of Black Tech Philly, a Philadelphia nonprofit expanding access to tech education, digital literacy, and AI literacy. What started as a conversation with a stranger coding in a coffee shop back in 2019 is now a program running in four Philadelphia schools, hosting city-wide Tech Town Halls, and building a growing community of tech professionals and aspiring entrepreneurs. Aisha and Ian talk through the free legal resources that helped him formalize the organization, the importance of building the right kind of culture that shaped how his team hires and holds people accountable, and how storytelling — not advertising — became his biggest lead source.
💡 What You'll Learn
How to find free legal help for 501(c)(3) formation through pro bono lawyer programs like Philly VIPWhy culture isn't your website's mission statement — it's the worst behavior you're willing to tolerate — and how to set that standard earlyHow showing up in person and telling one specific, sticky story about your business turns into inbound leadsHow to balance a full-time job with building your business in the early days without burning out⏱️ Episode Timestamps
00:02 – Welcome & meet Ian Kimble
00:55 – The coffee shop conversation that started Black Tech Philly
02:20 – What Black Tech Philly does today
05:20 – Is the appetite really there for tech & AI literacy?
09:39 – Deepfakes, media literacy, and “trust but verify”
12:23 – Getting free legal help early through Philly VIP
16:03 – The real definition of company culture
19:39 – How a LinkedIn shoutout sparked momentum
21:15 – Turning story and “being in the field” into inbound leads
28:27 – From political science to insurance sales to code
32:23 – The moment coding became “the thing”
33:53 – Building a sales pipeline for community partnerships
35:48 – Balancing a full-time job while building the org
43:06 – Why the name “Black Tech Philly” was intentional
44:57 – What “Do Small Business Like a Big Boss” means to Ian
46:06 – Where to find Black Tech Philly
🎤 About Our Guest
Ian Kimble is the co-founder and executive director of Black Tech Philly, a Philadelphia-based educational nonprofit founded in spring 2020, focused on expanding access to technology, digital literacy, and AI literacy across the city.
Website: https://blacktechphilly.org
Ian on LinkedIn: linkedin.com/in/iank6
Take the free Small Business Legal Risk Self-Assessment and get clarity before a contract, a lawsuit, or a bad partnership does it for you.
👉 Grab your assessment here: www.smallbizzlegalguide.com
🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC
Podcast Mantra:
Build the dream messy, build it scared, just don't build it small.
Link to episode
From Corporate Dropout to 6-Figure CEO: How Shan Thomas Built on Her Own Terms
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Shan Thomas, founder of Credible Visibility Media, to discuss how she left a six-figure corporate career to build a thriving business on her own terms. Shan shares how she leveraged her corporate experience, developed profitable systems, and created a business that delivers both financial success and work-life balance.
This conversation covers the real-life lessons behind building a business from the ground up—what worked, what didn't, and what every aspiring entrepreneur needs to hear.
🎧 What You'll Learn in This Episode:
How to leverage corporate experience to build credibility as an entrepreneur
The Bullseye Strategy for attracting ideal clients without limiting growth
A pricing framework to confidently raise your rates
How the TAGS Framework helps create a signature offer that stands out
Why your ideal client is often the person you were 5–10 years ago
⏱️ Episode Timestamps:
00:00 – Introduction
00:52 – Guest introduction: Shan Thomas
02:50 – From corporate career to entrepreneurship
08:34 – Overcoming challenges in a male-dominated industry
13:40 – Quitting without a plan and starting a business
19:36 – Faith, fear, and betting on yourself
25:00 – Profit strategy and revenue planning
27:08 – The Bullseye Strategy for client messaging
30:00 – The TAGS Framework
36:28 – Pricing with confidence
39:19 – Building the "10–4 Life"
42:41 – What "Do Small Business Like a Big Boss" means
44:24 – Wrap-up & calls to action
👤 About the Guest:
Shan Thomas is the founder of Credible Visibility Media, where she helps service-based business owners increase profitability through strategic positioning, signature offers, and scalable systems. Drawing from decades of Fortune 500 experience negotiating billion-dollar logistics contracts, Shan brings big-business strategies to small business owners. She is also the founder of Entrepreneur Her, an Atlanta-based community supporting women entrepreneurs.
Connect with Shan: LinkedIn — @shanthomasbiz
Ready to find out where your business is legally exposed?*
Take the free Small Business Legal Risk Self-Assessment and get clarity before a contract, a lawsuit, or a bad partnership does it for you.
👉 Grab your assessment here: www.smallbizzlegalguide.com
🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC
Podcast Mantra:
Build the dream messy, build it scared, just don't build it small.
If this episode helped you, don't forget to subscribe, download, and share it with another boss who needs to hear it.
Link to episode
How to Know When to Outsource
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Brad Stevens, founder and CEO of Outsource Access, to talk about knowing when it's time to outsource and how to build a team that helps your business grow.
Brad shares his entrepreneurial journey, the unexpected path that led him to build a 500+ employee offshore staffing company, and the systems, mindset, and metrics that have fueled his rapid growth.
🎧 What You’ll Learn in This Episode:
⏱️ Episode Timestamps
01:38 – Brad's origin story: renting Micro Machines toys in 4th grade
05:00 – Learning to spot problems worth solving
08:02 – The moment Brad knew entrepreneurship was the path
13:38 – How Brad thinks about building resilience
18:58 – The exploding pen disaster that led to Outsource Access
25:07 – Why Brad built his team in the Philippines
26:18 – Why Outsource Access serves 85 industries instead of niching down
29:49 – Building word-of-mouth marketing through content and education
33:45 – The two-question exercise for knowing what to outsource
40:14 – The 3 KPIs Brad watches most closely
44:27 – Brad's upcoming book, Automate and Delegate
48:38 – What "Do Small Business Like a Big Boss" means to Brad
🎤 About Our Guest
Brad Stevens is the founder and CEO of Outsource Access, an offshore virtual staffing firm he's grown to 500+ employees across 85 industries in just four and a half years. In 2021, Outsource Access was the only outsourcing company to receive Inc. magazine's Best in Business Award for firms making the biggest impact on their communities, industries, and the environment. His book, Automate and Delegate, is releasing soon.
🔗 Stay Connected with Sedgwick Andrews
👉 https://linktr.ee/Sedgwick_Andrews_LC
Want to see how your business stacks up? Download this business self-assessment: www.smallbizzlegalguide.com
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it.
Link to episode
Outsmarting the Big Guys: Building a Challenger Brand Agency from Scratch
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Justin Bajan, Co-Founder and Creative Director of Familiar Creatures, to talk about leaving a six-figure career to build an award-winning independent advertising agency from the ground up.
Justin shares how his team helps challenger brands outsmart larger competitors, the realities of entrepreneurship, and the lessons that helped Familiar Creatures become one of Adweek’s fastest-growing agencies.
🎧 What You’ll Learn in This Episode:
How Justin transitioned from corporate life to launching his own agencyThe realities of pricing professional services and avoiding undervaluing your workHow Familiar Creatures evaluates potential clients using its “Smiley Face System”Why saying no to the wrong opportunities can accelerate long-term growthHow small, agile teams can outperform much larger competitors⏱️ Episode Timestamps:
00:03 – Introduction01:10 – Leaving a six-figure salary02:56 – Moving his family to start over03:26 – Why Richmond became home for the business07:09 – Landing the first anchor client09:20 – The financial realities of early entrepreneurship11:58 – Learning while building the business13:52 – Pricing professional services17:22 – Building a reputation over time18:33 – Making decisions as business partners21:47 – The creative process behind successful campaigns26:06 – Scaling the agency from 2 to 10 people29:30 – Choosing the right clients30:23 – The “Smiley Face System” explained33:23 – Why saying no can be the best business decision37:57 – How small teams outperform big agencies41:08 – What “Do Small Business Like a Big Boss” means to Justin43:06 – Where to connect with Justin and Familiar Creatures👤 About the Guest:
Justin Bajan is the Co-Founder and Creative Director of Familiar Creatures, an independent advertising agency based in Richmond, Virginia. Since launching in 2018, the agency has been recognized as one of Adweek’s 25 fastest-growing agencies and has helped challenger brands like Duke’s Mayonnaise, Crunch Fitness, and Bubba Burger achieve remarkable growth through strategic creative marketing.
Website: familiarcreatures.com
Instagram: @familiarcreatures
Want to see how your business stacks up? Download this business self-assessment: www.smallbizzlegalguide.com
Stay Connected with Sedgwick Andrews:
👉 https://linktr.ee/Sedgwick_Andrews_LC
Build the dream messy, build it scared, just don't build it small.
If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it. 🎧
Link to episode
From Engineering to Landscaping COO: Recurring Revenue, Smart Hiring & Systems That Scale
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Doug Bonnell, Owner and COO of True North Landscaping, to talk about his journey from automotive engineer to leading and scaling a successful family-owned landscaping company.
This conversation covers the real-life lessons behind building a sustainable service business, creating recurring revenue, making strategic hires, and implementing systems that support long-term growth.
🎧 What You’ll Learn in This Episode:
Why recurring revenue is the foundation of a stable service-based business
How to decide whether to hire, outsource, or acquire to fill business gaps
The systems and software that transformed operations and job costing
How Doug and his wife successfully work together in the business
What every entrepreneur can learn from the landscaping industry's referral culture
⏱️ Episode Timestamps:
00:00 – Introduction
00:35 – Guest introduction: Doug Bonnell & True North Landscaping
01:17 – From automotive engineer to family business COO
03:03 – Taking the leap from corporate life
05:42 – Learning the business from the ground up
06:57 – Building recurring revenue through maintenance services
09:21 – Why recurring revenue matters
11:12 – Acquiring a competitor and expanding services
12:13 – Build, hire, or buy?
14:31 – Managing seasonality and workforce challenges
20:23 – Work-life balance as a business owner
23:43 – Running a business with your spouse
24:51 – Common mistakes customers make when hiring contractors
29:26 – Systems and technology that drive growth
32:12 – Advice for aspiring entrepreneurs
33:05 – What “Do Small Business Like a Big Boss” means to Doug
33:52 – Where to connect with Doug and True North Landscaping
👤 About the Guest:
Doug Bonnell is the Owner and COO of True North Landscaping, a high-end residential design, build, and maintenance company serving Northern Michigan. After earning an engineering degree from Western Michigan University and spending six years in the automotive industry, Doug joined the family business and has helped grow it into a 50-person operation with multiple service lines, including maintenance, irrigation, fertilization, and snow removal.
Connect with Doug:
LinkedIn: Doug Bonnell
Website: True North Landscaping
🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
👉 Register here: https://www.igotnext.co/training
👉 Grab your FREE Legal Guide at:
📘 Free Guide: www.smallbizzlegalguide.com
🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC
Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it. 🎧
Link to episode
Building Six-Figures Organically: Social Media, Government Contracts & Community
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Myown Holmes, Owner and Senior Strategist of Socially Polished and Founder of The Prism Effect, to talk about building a six-figure business organically while balancing family, a full-time career, and entrepreneurship.
Myown shares how she leveraged social media, strategic relationships, and community-building to grow her business, navigate government contracting opportunities, and create a platform that empowers minority women entrepreneurs.
🎧 What You’ll Learn in This Episode:
How the “Power of One” framework can help you grow without burnout
Why focusing on one platform can outperform trying to be everywhere at once
How to build a referral network and secure early testimonials through strategic partnerships
The government contracting opportunities many small business owners overlook
Why knowing your numbers and building the right advisory team is critical for growth
⏱️ Episode Timestamps:
00:04 – Welcome & guest introduction
01:04 – Building a business while raising a family
03:31 – The realities of building in the margins
07:25 – Knowing when it was time to leave her job
09:22 – Creating a structurally sound business
13:35 – Breaking into government contracting
16:12 – Diversifying revenue vs. stabilizing revenue
17:50 – The “always be marketing” mindset
18:57 – Knowing your numbers and building your dream team
22:38 – Finding the right platform for your audience
23:31 – The Power of One framework
26:04 – Organic marketing vs. paid advertising
31:10 – Building a referral network through bartering
35:59 – Using AI in small business
39:01 – The hardest lessons of entrepreneurship
40:26 – The mission behind The Prism Effect
46:22 – What “Do Small Business Like a Big Boss” means to Myown
48:22 – Where to connect with Myown
👤 About the Guest:
Myown Holmes is the Owner and Senior Strategist of Socially Polished, a boutique digital marketing agency based in Washington, D.C., specializing in social media strategy, personal branding, B2B social selling, and brand management. She is also the Founder of The Prism Effect, a community dedicated to supporting the mindset, wellness, and business growth of minority women entrepreneurs.
Connect with Myown:
LinkedIn: https://www.linkedin.com/in/myownh/
Website: https://socially-polished.com/
🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
👉 Register here: https://www.igotnext.co/training
👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com
https://smallbizzlegalguide.com
🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC
Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
Link to episode
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.
Link to episode
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:
⏱️ 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?
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Podcast Mantra:
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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:
⏱️ 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
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Podcast Mantra:
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🎧 If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.
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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.
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Podcast Mantra:
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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: [email protected]
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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?
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Podcast Mantra:
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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
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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: [email protected]
LinkedIn: Search “Bala Vishwanath”
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
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🎙️ 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. 🎧
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Stop Drowning in Tasks — How to Delegate Like a Boss with Tanya Thomas
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 begins03:10 – Navigating the early days of business05:54 – Building Team Delegate: From solo to agency09:05 – Transitioning from working in to working on11:52 – Delegation: The art of letting go15:08 – Identifying when to hire a virtual assistant18:03 – Overcoming control issues in delegation20:57 – Tools for effective task management23:54 – Onboarding and building relationships with VAs27:06 – Learning from mistakes and growing30:01 – The value of US-based virtual assistants32:57 – Finding fulfillment in helping others35:58 – Staying grounded in entrepreneurship💡 Key Takeaways:"Delegation is a skill set.""Communication is key.""Learn from your failures.""Identify when to hire a VA to manage overwhelm.""Trust is the foundation of client-VA relationships."🎤 About Our Guest:Tonya Thomas is the founder of Team Delegate, a virtual assistant agency offering US-based VAs to help businesses scale. Tonya’s entrepreneurial journey began in the early 2000s, and she now leads a growing agency focused on effective delegation, building trust, and supporting business owners as they grow their teams.
Connect with Tonya Thomas:
Website: teamdelegate.com
LinkedIn: linkedin.com/in/tonyathomas
Follow us for legal tips, business strategy, and boss-level motivation:
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Build the dream messy, build it scared, just don’t build it small.
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Don’t Be a Boss, Be a Leader — Building Partnerships That Change Lives with Gregory Weiss
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 Group01:37 – The importance of partnerships in staffing05:06 – Transitioning roles: From CEO to Managing Partner06:20 – Navigating COVID-1907:45 – Common hiring mistakes for small businesses10:03 – Building client relationships13:31 – The role of AI in recruitment16:55 – Managing chaos in staffing19:41 – The human element in business decisions23:19 – Staying focused amidst competition26:23 – Personal motivation and accountability29:16 – The importance of listening in business34:50 – Leadership vs. Bossing: A Philosophy💡 Takeaways:"We are in the business of helping people change their lives for the better.""Titles don’t mean a thing; it’s about the success of the company.""Just pick up the phone and talk to people—that’s how partnerships are built.""Sell with your ears, not your mouth.""Don’t be a boss, be a leader.""AI is hurting businesses because you’re losing human-to-human interaction."🎤 About Our Guest:Gregory Weiss is the Managing Partner of Action Staffing Group, a staffing firm focused on changing lives through meaningful employment. Gregory believes in leadership built on accountability, relationships, and understanding that people—not positions—are at the heart of every business.
Connect with Gregory:
LinkedIn: linkedin.com/in/gregory-weiss-2591a935
Website: actionstaffing-group.com
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.
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Why Your Biggest Security Threat Isn’t Hackers – It’s Your Humans
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 cybersecurity04:55 – The importance of cybersecurity for small businesses12:04 – The human element in cybersecurity20:06 – Best practices for employee offboarding25:04 – Balancing security with growth34:00 – The impact of AI on cybersecurity38:59 – Final thoughts on small business success👤 About the Guest:Carter Schoenberg is the Chief Cybersecurity Officer at SoundWay Consulting, Inc., with decades of experience in cybersecurity and risk management. Carter focuses on the critical role of human behavior in securing digital infrastructures for businesses of all sizes.
Connect with Carter Schoenberg:
LinkedIn: linkedin.com/in/carter-schoenberg-5122011
Website: soundwayconsulting.com
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Build the dream messy, build it scared, just don’t build it small.
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The Leadership Skill Nobody Teaches (But Every CEO Needs) | Richard Yep
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 trustWhy hiring for passion over perfect qualifications attracts the right talent to small businessesHow to balance finances with growth—and why patience often matters more than speedHow inclusive leadership improves decision-making and organizational effectivenessWhen to delegate, how to let go, and why listening is a leadership superpowerThe real cost of values-based decisions—and why they define organizational integrityPractical advice for entrepreneurs preparing to scale⏱️ Episode Timestamps:00:00 – Introduction02:54 – Navigating the challenges of leadership05:53 – Hiring and attracting talent in small businesses08:54 – Balancing finances and growth11:55 – Common challenges for CEOs and nonprofit leaders14:53 – The importance of communication and inclusivity17:47 – Delegation and letting go20:35 – Values-based decision making23:35 – Building an inclusive culture26:39 – Pivots and new ventures29:24 – Advice for entrepreneurs32:36 – Conclusion and resources👤 About the Guest:Richard Yep is the Vice President of Vetted Solutions, bringing decades of leadership experience from nonprofit organizations and executive search. He specializes in helping organizations navigate leadership transitions, build inclusive cultures, and make strategic decisions that align with core values.
Connect with Richard Yep:
LinkedIn: https://linkedin.com/in/richardyep
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
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From Alcatraz to Budding Wine Dynasty
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 businessNavigating Legal and Regulatory Challenges: Decoding federal alcohol licensing and finding loopholes to launch a winery in a dry countyTurning Mistakes Into Revenue Streams: How Nancy’s early wine failures led to profitable new product linesBuilding a Sustainable Business Model: How Nancy scaled her winery while keeping her passion and paycheck separate to prevent burnoutBalancing Full-Time Work with a 24/7 Passion: Setting boundaries and making use of simple tools to manage both business and full-time workRedefining Success on Your Own Terms: Why Nancy defines success as loving what you do—and not just making money⏱️ Episode Timestamps:00:00 – Introduction03:23–03:58 – How Nancy learned to make wine with no formal background10:01–10:28 – Cold-calling government officials to get wine-making approval25:10–25:45 – How mistakes became new revenue streams, like pineapple-grapefruit wine48:22 – 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.
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Excited and Terrified: The Dual Emotions Every New Leader Must Master
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 extraordinaryWhy leadership often feels both exciting and terrifyingThe power of mentorship in personal and professional growthHow remote work has changed collaboration and leadershipWhy strong processes are essential for managing complex projectsHow to achieve work-life balance through trust and flexibilityThe value of women-owned business certificationsWhy a research-minded approach leads to better client outcomesHow to simplify complex marketing challengesAdvice for aspiring leaders facing tough decisions⏱️ Episode Timestamps:
5:40-6:07– The importance of mentorship in leadership23:02 - 25:15 – Research-minded approach to client work34:07-34:34 – Doing small business like a big boss👤 About the Guest:
Karen Murphy is the President of FBM Integrated Marketing, a B2B marketing and branding agency. She leads with a research-driven mindset, a passion for mentorship, and a commitment to simplifying complex marketing challenges for clients.
🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof with confidence.
👉 Register here: https://www.igotnext.co/training
👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com
🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC
Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.
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The Importance of Systems and Coaches as a Business Owner with David Girton of LiveNow Fitness
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 businessThe biggest mistakes entrepreneurs make when they don’t have systemsWhy getting a business coach early can save years of frustrationHow to transition from being a service provider to a business ownerThe importance of knowing your value and standing by itHow networking and coaching accelerate growthWhy mental health and resilience matter in entrepreneurshipLessons 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 coach10:04–11:13 — 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
👉 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.
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From Google Search to Six-Figure Solo Law Firm: Lauren Lester
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 opportunitiesWhat it really takes to launch a solo law firm and bet on yourselfWhy setting strong work-life boundaries can actually attract better clientsHow Lauren’s “no Fridays” rule reshaped her business and personal lifeWays to leverage automation and legal technology to increase efficiencyWhen and how to make strategic pivots as your values evolveBusiness 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
👉 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.
Link to episode
From selling candy on the playground to building and selling multiple seven-figure companies
Episode Title:
From Selling Candy on the Playground to Building and Selling Multiple Seven-Figure Companies
Podcast:
Do Small Business Like a Big Boss
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 scaleHow 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 entrepreneursHow Cheryl uses a six-step meditation practice to make million-dollar decisions without burnout⏱️ Episode Timestamps:Guest introduction: Cheryl Perez06:35 – Knowing when you’re truly “done” with playing small27:59 – Why capacity limits revenue38:57 – 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
👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.
Link to episode
Why You Should Do Your Small Business Like a Big Boss!
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.
Connect with Aisha Massengill:
Instagram: https://www.instagram.com/sedgwickandrews/LinkedIn: https://www.linkedin.com/in/aisha-jorge-massengill-shrm-scp-95bbba4/overlay/about-this-profile/Website: https://sedgwickandrews.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 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.
Link to episode