The Bootstrapped EdTech Playbook: Offshore Teams, DIY PR, and 20K Users

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: The difference between PR and marketing Why local media coverage can be valuable How to approach sales through storytelling How to pitch articles to trade publications How earned, paid, and owned media work together How 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! 🎧

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 projects How to protect your business from depending on a single referral or acquisition channel Why owning your content and search traffic can create long-term growth How “Demo Week” helps improve the quality and speed of your team's work The $300K lesson on why trust cannot be bought from strangers ⏱️ Episode Timestamps: 00:19 – Introduction 00:59 – Guest introduction: Marcus Smith & Cloud Trailz 01:54 – Why he built the business on subscriptions, not projects 04:00 – How COVID fueled early growth and the risk that came with it 08:05 – Insulating the business from a single dominant channel 08:48 – Why they invest in owned content instead of renting attention 09:16 – SEO explained simply: matching intent to content 11:12 – The 3% buying vs. 95% browsing framework 12:29 – The corporate moment that made him want out 15:11 – How a joke turned him into a CEO 16:30 – Handling pushback on the subscription model 19:53 – The early hurdle: realizing nobody cares about your new business 22:34 – How to actually get customers to care 24:48 – A client transformation he's most proud of 29:11 – The “Demo Week” structure that changed everything 35:23 – The $300K mistake: trying to buy back demand 37:49 – Why “systems beat heroics” 40:23 – What “Do Small Business Like a Big Boss” means to Marcus 41:28 – 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. 🎧

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.