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EPISODE · Jul 15, 2026 · 54 MIN

How to Know When to Outsource

from Do Small Business Like a Big Boss Podcast · host Aisha Massengill

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. 🔗 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.

Episode metadata supplied by the publisher feed · Published Jul 15, 2026

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How to Know When to Outsource

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