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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Données mises à jour le 13/11/2026
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Start a Business Before You Feel Ready | Do Small Business like a Big Boss
Saison 1 · Épisode 30
mercredi 11 novembre 2026 • Durée 47:14
Your ideas deserve a home that's yours. Jessica Dalka shares how she turned a side blog into Chicago Planner Magazine, and how she decides what gets her time, her energy and her yes.
Jessica Dalka is the owner and founder of Chicago Planner Magazine, a no-fluff resource for the events and hospitality industry in Chicago. She started it while working in restaurants and hotels, and has kept it going through a pandemic and several big-name event jobs. Host Aisha Jorge Massengill talks with her about starting a business before you feel ready, wearing every hat, and building your own thing alongside a full-time job. You'll also hear how Jessica picks networking events, why she keeps meetings to 15 minutes, and why asking for a fair price doesn't make you a bad person.
💡 What You'll Learn
• How to decide which networking events are worth your time: look at the audience, step outside your own industry, and know when a room is repetitive
• How to keep meetings to 15 minutes by pre-qualifying every request first
• Why testing one small piece before you scale beats a big launch, and what a clean-water project teaches about it
• How to spot early when someone never planned to pay you, and say no without guilt
• Why Jessica adds "accomplishment" alongside "success" when she defines her own impact
⏱️ Episode Timestamps
00:00 – Welcome and meet Jessica Dalka, founder of Chicago Planner Magazine
01:50 – How a steakhouse job and a side blog sparked a business of her own
04:00 – Dream killers, other people's fears and ideas taken without credit
07:15 – Building on the side: focus, sleep and the pandemic networking push
09:15 – Choosing which networking events are worth your time
13:30 – Her writing process: notebooks, compartmentalizing and protecting focus
17:15 – The six-week job that made the decision for her
20:10 – The hardest hat to wear: explaining digital before it was mainstream
21:30 – Digital vs. print: why the mix matters
23:15 – Test one small piece first: lessons from a clean-water project
27:45 – Money and vision: how the pandemic taught her to say no
31:00 – Being of service while respecting what your work is worth
32:56 – Big-business habits: speaking every industry's language and turning creativity into dollar value
35:20 – Making every minute count: pre-qualified 15-minute meetings
39:30 – Tools and routines: "if it's not on my calendar, it doesn't exist"
41:30 – What "enough" looks like and why events are undervalued
43:15 – Advice for the messy, scared first year
44:36 – What "Do Small Business Like a Big Boss" means: being self-defining
🎤 About Our Guest
Jessica Dalka is the owner and founder of Chicago Planner Magazine. With a background in advertising and PR, she has built a career designing events for Fortune 500 executives, celebrities, athletes and politicians.
🎙️ 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.
Permission to fire:How an SEO Founder Keeps Clients for 16 Years | Do Small Business Like a Big Boss
Saison 1
mercredi 4 novembre 2026 • Durée 44:10
Tired of marketers who overpromise? Pete Kleinjan, founder of Tiger29, explains why he tells clients to fire him if they're not getting results, and why that honesty keeps them around.
Pete Kleinjan started in SEO in 2003 after his boss handed him a Wikipedia article, and founded Tiger29 in Sioux Falls, South Dakota in 2009. Today the agency serves local service businesses across more than 20 states. In this episode he shares the sales tax letter that made his hands shake, why he waited seven years to make his first hire, how he turned "recipes" into SOPs, the $150 SEO Power Hour that proves value before anyone signs, and why he has worked with one client for 16 years without ever meeting in person.
💡 What You'll Learn
- Why owning a job and owning a business are not the same thing, and how Pete found the difference
- How to set client expectations so honesty wins you referrals instead of costing you sales
- Why "every molehill feels like a mountain until you've climbed it," and what that meant for his first hire
- How to turn what's in your head into SOPs your team can run without you
- Why the systems that get you to $500K a year break at $1M
⏱️ Episode Timestamps
00:00 – Cold open
00:47 – Meet Pete Kleinjan, founder of Tiger29
02:04 – The origin story: a sales guy and one Wikipedia article
02:58 – Why he left a good job in 2009: something better, not more
03:27 – What SEO is, and what AI changed
05:41 – Why the company is named Tiger29
07:28 – Owning a job vs. owning a business
09:07 – The coach, the book and the mindset shift
11:02 – Doubt, resilience and just another Tuesday
Don't Play Small: Brand Voice and Confidence for Founders | Do Small Business like a Big Boss
Saison 1
jeudi 22 octobre 2026 • Durée 36:18
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
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
PR for Small Business: Why Hyperlocal Beats Forbes
mercredi 14 octobre 2026 • Durée 46:33
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.
The $300K Mistake That Taught Him You Can’t Buy Trust
mercredi 7 octobre 2026 • Durée 42:21
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
The No-Code Playbook for First-Time Founders
mercredi 30 septembre 2026 • Durée 49:19
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
Why Digital Literacy Is the New Small Business Skill | Do Small Business like a Big Boss
mercredi 29 juillet 2026 • Durée 47:10
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 VIP
Why culture isn't your website's mission statement — it's the worst behavior you're willing to tolerate — and how to set that standard early
How 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
From Corporate Dropout to 6-Figure CEO: How Shan Thomas Built on Her Own Terms
mercredi 22 juillet 2026 • Durée 42:50
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
How to Know When to Outsource
mercredi 15 juillet 2026 • Durée 54:13
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 first
How to view hiring as an investment instead of an expense
Why Outsource Access serves businesses across 85 industries instead of specializing in one niche
The key performance indicators Brad uses to measure outsourcing success
How 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.
Outsmarting the Big Guys: Building a Challenger Brand Agency from Scratch
jeudi 9 juillet 2026 • Durée 37:23
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 agency
The realities of pricing professional services and avoiding undervaluing your work
How Familiar Creatures evaluates potential clients using its “Smiley Face System”
Why saying no to the wrong opportunities can accelerate long-term growth
How small, agile teams can outperform much larger competitors
⏱️ Episode Timestamps:
00:03 – Introduction
01:10 – Leaving a six-figure salary
02:56 – Moving his family to start over
03:26 – Why Richmond became home for the business
07:09 – Landing the first anchor client
09:20 – The financial realities of early entrepreneurship
11:58 – Learning while building the business
13:52 – Pricing professional services
17:22 – Building a reputation over time
18:33 – Making decisions as business partners
21:47 – The creative process behind successful campaigns
26:06 – Scaling the agency from 2 to 10 people
29:30 – Choosing the right clients
30:23 – The “Smiley Face System” explained
33:23 – Why saying no can be the best business decision
37:57 – How small teams outperform big agencies
41:08 – What “Do Small Business Like a Big Boss” means to Justin
43:06 – 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.
Détails sur Do Small Business Like a Big Boss Podcast, podcast de Aisha Massengill
12:09 – The sales tax letter that made his hands shake
14:28 – Quick pause: like, follow and subscribe
14:56 – Seven years solo, then the first hire
18:05 – Why he waited so long to hire: fear
19:54 – SEO's bad reputation and the $150 SEO Power Hour
21:15 – Proof over promises: if you're not getting results, fire us
23:48 – Did honesty ever cost him a sale?
25:12 – Handling the no
28:05 – Systems: SOPs as recipes anyone can follow
31:38 – What gets you to $500K breaks at $1M
31:53 – The lottery-ticket file rule
33:55 – Letting go of email: it's handled
35:09 – Quick beat: your free Legal Risk Assessment
35:41 – From Sioux Falls to 20+ states
38:08 – Keeping up with the algorithms: masterminds, newsletters, NotebookLM
41:00 – The gem: surround yourself with good people
42:30 – What Do Small Business Like a Big Boss means to Pete
43:07 – Close: build the dream messy
🎤 About Our Guest
Pete Kleinjan is the founder of Tiger29, an SEO and digital marketing agency in Sioux Falls, South Dakota, that helps local service businesses compete online. He has worked in search engine optimization since 2003, founded Tiger29 in 2009, and is known for the SEO Power Hour, a live session where he makes visible improvements to a business's online presence before any contract is signed. Outside of work he serves as a church deacon and nonprofit board member in the Sioux Falls community.
🎙️ 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.
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.
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! 🎧
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.
🚀 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.
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. 🎧
👤 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.
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.
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.
Build the dream messy, build it scared, just don't build it small.
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.
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.
