Do Small Business Like a Big Boss Podcast
Booking Overview
Metrics
Episodes: 26
Frequency: Weekly
Rating: 5.0/5.0
Estimated listeners: 1,000 - 10,000
Listener location: USA
Contact Information
Publicly listed emails
aisha.massengill@sedgwickandrews.com
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Host
Aisha Jorge Massengill - Founder of Sedgwick Andrews Legal & Consulting and a seasoned employment attorney who has advised large publicly traded companies for more than two decades.
Booking Intelligence
Booking Requirements
Recent Guest Discussions
Ian Kimble - Nonprofit Formation, Legal Resources, Company Culture, Digital Literacy, Artificial Intelligence Literacy, Storytelling-based Marketing, And Building A Sales Pipeline Through Community Partnerships.
Shan Thomas - Moving From Corporate Employment To Entrepreneurship, Profitable Systems, Client Positioning, Signature Offers, Pricing, Revenue Planning, And Work-life Balance.
Brad Stevens - Outsourcing, Delegation, Hiring, Resilience, Performance Metrics, Educational Marketing, And Scaling A Staffing Company.
Justin Bajan - Launching An Agency, Pricing Professional Services, Client Selection, Challenger-brand Strategy, Creative Operations, And Competing With Larger Agencies.
Doug Bonnell - Recurring Revenue, Hiring Versus Outsourcing Or Acquisition, Operational Systems, Job Costing, Seasonality, Family-business Leadership, And Service-business Growth.
Recent Topics
Episodes
The $300K Mistake That Taught Him You Can’t Buy Trust
October 07, 2026
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 $...
The No-Code Playbook for First-Time Founders
September 30, 2026
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 i...
Why Digital Literacy Is the New Small Business Skill | Do Small Business like a Big Boss
July 29, 2026
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 school...
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Frequently asked questions
How do I get in touch with Do Small Business Like a Big Boss Podcast?
Do Small Business Like a Big Boss Podcast is hosted by Aisha Jorge Massengill. Its publicly listed email is aisha.massengill@sedgwickandrews.com. For guest bookings, the host or producer is usually the best person to reach. Podseeker helps you find direct host and producer contacts and pitch from your own inbox.
What is the email for Do Small Business Like a Big Boss Podcast?
The publicly listed email for Do Small Business Like a Big Boss Podcast: aisha.massengill@sedgwickandrews.com.
How many listeners does Do Small Business Like a Big Boss Podcast have?
Podseeker estimates Do Small Business Like a Big Boss Podcast reaches 1,000 to 10,000 listeners per episode. Only the publisher has exact numbers.
Who is an ideal guest for Do Small Business Like a Big Boss Podcast?
Do Small Business Like a Big Boss Podcast typically books rising experts. Typical guest background: Founders, owners, executives, and operators with firsthand experience building, formalizing, or scaling a small or midsize business. Strong candidates typically bring measurable business results, meaningful team-building or operational experience, or specialized expertise in areas such as marketing, hiring, outsourcing, legal risk, or business systems. Common among recent guests: Built or scaled a service business, agency, nonprofit, or staffing company; Expanded a team, service offering, or customer base; Developed repeatable systems, revenue strategies, or operational frameworks. Recent guests include Ian Kimble, Shan Thomas, and Brad Stevens.
How hard is it to get booked on Do Small Business Like a Big Boss Podcast?
Medium. Guests usually need solid credentials in the topic and an idea that fits the show.
What topics does Do Small Business Like a Big Boss Podcast cover?
Recent episodes cover Business, Entrepreneurship, Scaling, Leadership, and Hiring. Pitch an idea tied to one of these topics and mention a recent episode.
Publicly listed emails
aisha.massengill@sedgwickandrews.com
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