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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.
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:
⏱️ 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! 🎧
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:
⏱️ Episode Timestamps:
👤 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. 🎧
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.
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
⏱️ Episode Timestamps
00:02 – Welcome & meet Ian Kimble
00:55 – The coffee shop conversation that started Black Tech Philly
02:20 – What Black Tech Philly does today
05:20 – Is the appetite really there for tech & AI literacy?
09:39 – Deepfakes, media literacy, and “trust but verify”
12:23 – Getting free legal help early through Philly VIP
16:03 – The real definition of company culture
19:39 – How a LinkedIn shoutout sparked momentum
21:15 – Turning story and “being in the field” into inbound leads
28:27 – From political science to insurance sales to code
32:23 – The moment coding became “the thing”
33:53 – Building a sales pipeline for community partnerships
35:48 – Balancing a full-time job while building the org
43:06 – Why the name “Black Tech Philly” was intentional
44:57 – What “Do Small Business Like a Big Boss” means to Ian
46:06 – Where to find Black Tech Philly
🎤 About Our Guest
Ian Kimble is the co-founder and executive director of Black Tech Philly, a Philadelphia-based educational nonprofit founded in spring 2020, focused on expanding access to technology, digital literacy, and AI literacy across the city.
Website: https://blacktechphilly.org
Ian on LinkedIn: linkedin.com/in/iank6
Take the free Small Business Legal Risk Self-Assessment and get clarity before a contract, a lawsuit, or a bad partnership does it for you.
👉 Grab your assessment here: www.smallbizzlegalguide.com
🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC
Podcast Mantra:
Build the dream messy, build it scared, just don't build it small.
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Shan Thomas, founder of Credible Visibility Media, to discuss how she left a six-figure corporate career to build a thriving business on her own terms. Shan shares how she leveraged her corporate experience, developed profitable systems, and created a business that delivers both financial success and work-life balance.
This conversation covers the real-life lessons behind building a business from the ground up—what worked, what didn't, and what every aspiring entrepreneur needs to hear.
🎧 What You'll Learn in This Episode:
How to leverage corporate experience to build credibility as an entrepreneur
The Bullseye Strategy for attracting ideal clients without limiting growth
A pricing framework to confidently raise your rates
How the TAGS Framework helps create a signature offer that stands out
Why your ideal client is often the person you were 5–10 years ago
⏱️ Episode Timestamps:
00:00 – Introduction
00:52 – Guest introduction: Shan Thomas
02:50 – From corporate career to entrepreneurship
08:34 – Overcoming challenges in a male-dominated industry
13:40 – Quitting without a plan and starting a business
19:36 – Faith, fear, and betting on yourself
25:00 – Profit strategy and revenue planning
27:08 – The Bullseye Strategy for client messaging
30:00 – The TAGS Framework
36:28 – Pricing with confidence
39:19 – Building the "10–4 Life"
42:41 – What "Do Small Business Like a Big Boss" means
44:24 – Wrap-up & calls to action
👤 About the Guest:
Shan Thomas is the founder of Credible Visibility Media, where she helps service-based business owners increase profitability through strategic positioning, signature offers, and scalable systems. Drawing from decades of Fortune 500 experience negotiating billion-dollar logistics contracts, Shan brings big-business strategies to small business owners. She is also the founder of Entrepreneur Her, an Atlanta-based community supporting women entrepreneurs.
Connect with Shan: LinkedIn — @shanthomasbiz
Ready to find out where your business is legally exposed?*
Take the free Small Business Legal Risk Self-Assessment and get clarity before a contract, a lawsuit, or a bad partnership does it for you.
👉 Grab your assessment here: www.smallbizzlegalguide.com
🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC
Podcast Mantra:
Build the dream messy, build it scared, just don't build it small.
If this episode helped you, don't forget to subscribe, download, and share it with another boss who needs to hear it.
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Brad Stevens, founder and CEO of Outsource Access, to talk about knowing when it's time to outsource and how to build a team that helps your business grow.
Brad shares his entrepreneurial journey, the unexpected path that led him to build a 500+ employee offshore staffing company, and the systems, mindset, and metrics that have fueled his rapid growth.
🎧 What You’ll Learn in This Episode:
⏱️ Episode Timestamps
01:38 – Brad's origin story: renting Micro Machines toys in 4th grade
05:00 – Learning to spot problems worth solving
08:02 – The moment Brad knew entrepreneurship was the path
13:38 – How Brad thinks about building resilience
18:58 – The exploding pen disaster that led to Outsource Access
25:07 – Why Brad built his team in the Philippines
26:18 – Why Outsource Access serves 85 industries instead of niching down
29:49 – Building word-of-mouth marketing through content and education
33:45 – The two-question exercise for knowing what to outsource
40:14 – The 3 KPIs Brad watches most closely
44:27 – Brad's upcoming book, Automate and Delegate
48:38 – What "Do Small Business Like a Big Boss" means to Brad
🎤 About Our Guest
Brad Stevens is the founder and CEO of Outsource Access, an offshore virtual staffing firm he's grown to 500+ employees across 85 industries in just four and a half years. In 2021, Outsource Access was the only outsourcing company to receive Inc. magazine's Best in Business Award for firms making the biggest impact on their communities, industries, and the environment. His book, Automate and Delegate, is releasing soon.
🔗 Stay Connected with Sedgwick Andrews
👉 https://linktr.ee/Sedgwick_Andrews_LC
Want to see how your business stacks up? Download this business self-assessment: www.smallbizzlegalguide.com
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it.
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Justin Bajan, Co-Founder and Creative Director of Familiar Creatures, to talk about leaving a six-figure career to build an award-winning independent advertising agency from the ground up.
Justin shares how his team helps challenger brands outsmart larger competitors, the realities of entrepreneurship, and the lessons that helped Familiar Creatures become one of Adweek’s fastest-growing agencies.
🎧 What You’ll Learn in This Episode:
⏱️ Episode Timestamps:
👤 About the Guest:
Justin Bajan is the Co-Founder and Creative Director of Familiar Creatures, an independent advertising agency based in Richmond, Virginia. Since launching in 2018, the agency has been recognized as one of Adweek’s 25 fastest-growing agencies and has helped challenger brands like Duke’s Mayonnaise, Crunch Fitness, and Bubba Burger achieve remarkable growth through strategic creative marketing.
Website: familiarcreatures.com
Instagram: @familiarcreatures
Want to see how your business stacks up? Download this business self-assessment: www.smallbizzlegalguide.com
Stay Connected with Sedgwick Andrews:
👉 https://linktr.ee/Sedgwick_Andrews_LC
Build the dream messy, build it scared, just don't build it small.
If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it. 🎧
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Doug Bonnell, Owner and COO of True North Landscaping, to talk about his journey from automotive engineer to leading and scaling a successful family-owned landscaping company.
This conversation covers the real-life lessons behind building a sustainable service business, creating recurring revenue, making strategic hires, and implementing systems that support long-term growth.
🎧 What You’ll Learn in This Episode:
Why recurring revenue is the foundation of a stable service-based business
How to decide whether to hire, outsource, or acquire to fill business gaps
The systems and software that transformed operations and job costing
How Doug and his wife successfully work together in the business
What every entrepreneur can learn from the landscaping industry's referral culture
⏱️ Episode Timestamps:
00:00 – Introduction
00:35 – Guest introduction: Doug Bonnell & True North Landscaping
01:17 – From automotive engineer to family business COO
03:03 – Taking the leap from corporate life
05:42 – Learning the business from the ground up
06:57 – Building recurring revenue through maintenance services
09:21 – Why recurring revenue matters
11:12 – Acquiring a competitor and expanding services
12:13 – Build, hire, or buy?
14:31 – Managing seasonality and workforce challenges
20:23 – Work-life balance as a business owner
23:43 – Running a business with your spouse
24:51 – Common mistakes customers make when hiring contractors
29:26 – Systems and technology that drive growth
32:12 – Advice for aspiring entrepreneurs
33:05 – What “Do Small Business Like a Big Boss” means to Doug
33:52 – Where to connect with Doug and True North Landscaping
👤 About the Guest:
Doug Bonnell is the Owner and COO of True North Landscaping, a high-end residential design, build, and maintenance company serving Northern Michigan. After earning an engineering degree from Western Michigan University and spending six years in the automotive industry, Doug joined the family business and has helped grow it into a 50-person operation with multiple service lines, including maintenance, irrigation, fertilization, and snow removal.
Connect with Doug:
LinkedIn: Doug Bonnell
Website: True North Landscaping
🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
👉 Register here: https://www.igotnext.co/training
👉 Grab your FREE Legal Guide at:
📘 Free Guide: www.smallbizzlegalguide.com
🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC
Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it. 🎧
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Myown Holmes, Owner and Senior Strategist of Socially Polished and Founder of The Prism Effect, to talk about building a six-figure business organically while balancing family, a full-time career, and entrepreneurship.
Myown shares how she leveraged social media, strategic relationships, and community-building to grow her business, navigate government contracting opportunities, and create a platform that empowers minority women entrepreneurs.
🎧 What You’ll Learn in This Episode:
How the “Power of One” framework can help you grow without burnout
Why focusing on one platform can outperform trying to be everywhere at once
How to build a referral network and secure early testimonials through strategic partnerships
The government contracting opportunities many small business owners overlook
Why knowing your numbers and building the right advisory team is critical for growth
⏱️ Episode Timestamps:
00:04 – Welcome & guest introduction
01:04 – Building a business while raising a family
03:31 – The realities of building in the margins
07:25 – Knowing when it was time to leave her job
09:22 – Creating a structurally sound business
13:35 – Breaking into government contracting
16:12 – Diversifying revenue vs. stabilizing revenue
17:50 – The “always be marketing” mindset
18:57 – Knowing your numbers and building your dream team
22:38 – Finding the right platform for your audience
23:31 – The Power of One framework
26:04 – Organic marketing vs. paid advertising
31:10 – Building a referral network through bartering
35:59 – Using AI in small business
39:01 – The hardest lessons of entrepreneurship
40:26 – The mission behind The Prism Effect
46:22 – What “Do Small Business Like a Big Boss” means to Myown
48:22 – Where to connect with Myown
👤 About the Guest:
Myown Holmes is the Owner and Senior Strategist of Socially Polished, a boutique digital marketing agency based in Washington, D.C., specializing in social media strategy, personal branding, B2B social selling, and brand management. She is also the Founder of The Prism Effect, a community dedicated to supporting the mindset, wellness, and business growth of minority women entrepreneurs.
Connect with Myown:
LinkedIn: https://www.linkedin.com/in/myownh/
Website: https://socially-polished.com/
🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
👉 Register here: https://www.igotnext.co/training
👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com
https://smallbizzlegalguide.com
🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC
Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
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