Do Small Business Like a Big Boss Podcast

Aisha Massengill
  • 5.0 (100)
  • Entrepreneurship

Ready to take your small business from basement startup to Big Boss success? Welcome to Do Small Business Like a Big Boss! where we prove that with the right strategy, any up and coming business owner can compete with the big guys. Hosted by Aisha Jorge Massengill, founder of Sedgwick Andrews Legal & Consulting, a seasoned employment attorney who's advised large publicly traded companies for over two decades, this podcast is your courtside seat to business transformation. Just like that fearless 13-year-old girl shouting ""I got next!"" on Bronx basketball courts, successful entrepreneurs don't just wait their turn—they prepare for it. They study the game, assess the competition, and build the skills they need to win when opportunity calls. What You'll Discover: Real Success Stories: In-depth interviews with business owners who've successfully scaled from side hustles to legitimate enterprises Strategic Frameworks: Proven systems and structures that help small businesses compete like industry giants Legal & HR Insights: Employment law guidance that protects your growing team while fostering company culture Risk Management for Entrepreneurs: Smart ways to minimize liability while maximizing opportunity Perfect for: Entrepreneurs ready to legitimize their side hustles into scalable businesses Small Business Owners (10-250 employees) seeking strategic growth frameworks HR Professionals navigating employment challenges in growing companies Ambitious Leaders who refuse to let limited resources limit their vision Each episode features candid interviews with business owners and operators who have navigated the challenges of growth, overcome obstacles, and achieved extraordinary success. Whether you’re scaling your team, refining your business model, or developing a winning mindset, this podcast provides the inspiration and guidance you need to build with discipline, confidence, and purpose. Your turn is coming. Are you ready? New episodes drop every week because champions don't take days off. Subscribe now and join thousands of entrepreneurs who refuse to wait on the sidelines. Your business growth journey starts here.

  1. 13h ago

    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.

  2. Oct 14

    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! 🎧

  3. Oct 7

    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. 🎧

  4. Sep 30

    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.

  5. Jul 29

    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 leads How to balance a full-time job with building your business in the early days without burning out ⏱️ Episode Timestamps 00:02 – Welcome & meet Ian Kimble 00:55 – The coffee shop conversation that started Black Tech Philly 02:20 – What Black Tech Philly does today 05:20 – Is the appetite really there for tech & AI literacy? 09:39 – Deepfakes, media literacy, and “trust but verify” 12:23 – Getting free legal help early through Philly VIP 16:03 – The real definition of company culture 19:39 – How a LinkedIn shoutout sparked momentum 21:15 – Turning story and “being in the field” into inbound leads 28:27 – From political science to insurance sales to code 32:23 – The moment coding became “the thing” 33:53 – Building a sales pipeline for community partnerships 35:48 – Balancing a full-time job while building the org 43:06 – Why the name “Black Tech Philly” was intentional 44:57 – What “Do Small Business Like a Big Boss” means to Ian 46:06 – Where to find Black Tech Philly 🎤 About Our Guest Ian Kimble is the co-founder and executive director of Black Tech Philly, a Philadelphia-based educational nonprofit founded in spring 2020, focused on expanding access to technology, digital literacy, and AI literacy across the city. 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.

  6. Jul 22

    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.

  7. Jul 15

    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: The two-question exercise to identify what you should outsource firstHow to view hiring as an investment instead of an expenseWhy Outsource Access serves businesses across 85 industries instead of specializing in one nicheThe key performance indicators Brad uses to measure outsourcing successHow educational content and referrals helped grow the business without paid advertising ⏱️ Episode Timestamps 01:38 – Brad's origin story: renting Micro Machines toys in 4th grade 05:00 – Learning to spot problems worth solving 08:02 – The moment Brad knew entrepreneurship was the path 13:38 – How Brad thinks about building resilience 18:58 – The exploding pen disaster that led to Outsource Access 25:07 – Why Brad built his team in the Philippines 26:18 – Why Outsource Access serves 85 industries instead of niching down 29:49 – Building word-of-mouth marketing through content and education 33:45 – The two-question exercise for knowing what to outsource 40:14 – The 3 KPIs Brad watches most closely 44:27 – Brad's upcoming book, Automate and Delegate 48:38 – What "Do Small Business Like a Big Boss" means to Brad 🎤 About Our Guest Brad Stevens is the founder and CEO of Outsource Access, an offshore virtual staffing firm he's grown to 500+ employees across 85 industries in just four and a half years. In 2021, Outsource Access was the only outsourcing company to receive Inc. magazine's Best in Business Award for firms making the biggest impact on their communities, industries, and the environment. His book, Automate and Delegate, is releasing soon. 🔗 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.

  8. Jul 9

    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. 🎧

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Ratings & Reviews

5
out of 5
100 Ratings

About

Ready to take your small business from basement startup to Big Boss success? Welcome to Do Small Business Like a Big Boss! where we prove that with the right strategy, any up and coming business owner can compete with the big guys. Hosted by Aisha Jorge Massengill, founder of Sedgwick Andrews Legal & Consulting, a seasoned employment attorney who's advised large publicly traded companies for over two decades, this podcast is your courtside seat to business transformation. Just like that fearless 13-year-old girl shouting ""I got next!"" on Bronx basketball courts, successful entrepreneurs don't just wait their turn—they prepare for it. They study the game, assess the competition, and build the skills they need to win when opportunity calls. What You'll Discover: Real Success Stories: In-depth interviews with business owners who've successfully scaled from side hustles to legitimate enterprises Strategic Frameworks: Proven systems and structures that help small businesses compete like industry giants Legal & HR Insights: Employment law guidance that protects your growing team while fostering company culture Risk Management for Entrepreneurs: Smart ways to minimize liability while maximizing opportunity Perfect for: Entrepreneurs ready to legitimize their side hustles into scalable businesses Small Business Owners (10-250 employees) seeking strategic growth frameworks HR Professionals navigating employment challenges in growing companies Ambitious Leaders who refuse to let limited resources limit their vision Each episode features candid interviews with business owners and operators who have navigated the challenges of growth, overcome obstacles, and achieved extraordinary success. Whether you’re scaling your team, refining your business model, or developing a winning mindset, this podcast provides the inspiration and guidance you need to build with discipline, confidence, and purpose. Your turn is coming. Are you ready? New episodes drop every week because champions don't take days off. Subscribe now and join thousands of entrepreneurs who refuse to wait on the sidelines. Your business growth journey starts here.

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