Over 80% of business owners can't find qualified people. But 15–25% are thriving, hiring, retaining, and growing at the same time. The difference isn't luck or budget; it's strategy. Rob Levin breaks down the three fundamental shifts that separate winners from everyone else: designing culture instead of hoping for it, competing for talent with the same intensity you compete for customers, and expanding your talent pool beyond local markets.

Episode Highlight
"Talent deserves the same strategic attention you give revenue."

Actionable Insights

1. Design culture, don't let it happen by default: Most owners still believe that paychecks drive performance, but those days are gone. Great people want to be part of something meaningful. Reinforce your core values through hiring, firing, recognition, and promotion. It's not easy, but it's never too late to shift culture. [03:53]
2. Your employer brand may be the reason why great candidates won't apply: Before applying, candidates check you out online. Check out your Glassdoor rating today. If the reviews are accurate, you have a culture problem to solve. If they're skewed by disgruntled former employees, ask your team to share their real experience, without incentives or scripts. Also, rewrite your job descriptions to sell the company and role, not just list requirements. A thoughtful job posting signals that you care about candidate experience. [06:35]
3. Stop fishing in a shrinking pond, expand your talent pool through remote and nearshore hiring: Most business owners say it's impossible to find good people locally. It's not. They're just fishing in a shrinking pond. Remote hiring expands your access to talent you can't reach locally. Nearshore or offshore hiring takes it a step further: you gain access to qualified people and reduce labor costs at the same time. Use talent partners to handle recruiting, vetting, and payroll. You're not just solving today's hiring crisis, you're building a structural advantage. [09:24]

Ready to apply these insights to your own business? Download the free Action Kit

More Resources:

• 88% of Small Businesses Can't Find Qualified People. The Other 12% Are Doing This.
• 7 Culture Practices Worth Stealing

More About Rob Levin & WorkBetterNow

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Follow Rob Levin on Substack.
Out now! The New Talent Playbook: The Ultimate Guide to Building Your Dream Team 📕 Available on Amazon or visit thenewtalentplaybook.com and get the free scorecard.

Alan Pentz, AI investor and operator, cuts through AI hype with a clear framework: we're entering the era of "multiplayer AI," where individual productivity gains transform into company-wide business transformation. AI success isn't about replacing people—it's about shifting from doing work to managing AI agents. This structural change in how businesses operate will separate forward-moving founders from the rest.

Episode Highlight
"The reality is the opportunities on the table right now, every industry is going to be remixed because of this collapse of services and software into each other. Don't you want to be a part of that?"

About the Guest
Alan Pentz founded OwnerRx to help business owners adopt AI in practical, real-world ways. As a hands-on investor and operator across government consulting, AI software, and defense manufacturing, he brings frontline credibility. After stepping back from day-to-day CEO duties, he's 10x'd his personal productivity in six months by building AI agent systems and now teaches cohorts of business owners how to replicate this at scale.

Key Takeaways

1. Multiplayer AI is the breakthrough: Single-player AI (personal automation) already works. The scalability challenge is deploying to teams—handling authentication, legacy software, and user friction. Claude Cowork is the first real multiplayer solution, sandboxing AI work with permissions and MCP integration. If you're waiting for "maturity," you're already behind. [04:11]

2. Building beats talking: Most owners don't grasp AI's potential until they build something. Conceptual understanding doesn't stick. You must see agents run, complete tasks instantly, and become real. Once that clicks, your mindset shifts to encoding entire workflows into skills and agents. [08:52]

3. Expand, don't just cut costs: Using AI to fire people is the wrong play. The right move: expand what your team can do. A 10x more productive team member becomes invaluable, not expendable. Real competitive advantage comes from serving more customers, going deeper with existing ones, or entering new markets. [15:39]

4. Lead the culture shift: As owner, get hands-on with Claude Cowork this month. Understand how your team must evolve from "doing work" to "managing AI agents." This is a culture shift, not just a tool switch. Model it, then cascade it across your organization. [26:14]

Ready to apply these insights to your own business? Download the free Action Kit

More About Alan Pentz

Check out OwnerRx
Connect with Alan on LinkedIn

More About Rob Levin & WorkBetterNow

Like this show? Click on over and subscribe to our YouTube channel!
Follow Rob Levin on Substack.
Out now! The New Talent Playbook: The Ultimate Guide to Building Your Dream Team 📕 Available on Amazon or visit thenewtalentplaybook.com and get the free scorecard.

Declining employee engagement is a warning signal for every small and mid-size business. Gallup's 2026 State of the Global Workplace report shows engagement dropping across the board, but Rob Levin unpacks three critical takeaways that separate thriving companies from those fighting burnout. Discover why manager stress signals a crisis, why every seat counts more than you think, and concrete, cost-effective moves to strengthen culture, reduce turnover, and position your team to leverage AI competitively.

Episode Highlight
"If only one out of every three people on your team were engaged in your business, in a smaller mid-size business, you'd probably be out of business, because every seat counts in a smaller, mid-size business."

Actionable Insights

1. Core Values as Decision Filters: Define 3-5 core values that reflect who you actually are, document them, and give real examples of what living those values looks like daily. This guides the hundreds of micro-decisions your team makes. [05:11]

2. Manager Burnout as Your Warning Signal: Declining manager engagement signals stress and burnout, usually from covering for disengaged team members. Fix hiring quality immediately, establish a culture where poor performers don't linger, and audit leadership directives for clarity and realism. [07:46]

3. Internal Mobility Drives Retention: Top performers leave when they see no path forward. Create a formal internal mobility program mapping growth pathways and visible ways people can develop, shift roles, or take on bigger challenges inside your company. [06:42]

Ready to apply these insights to your own business? Download the free Action Kit

More Resources:

• 88% of Small Businesses Can't Find Qualified People. The Other 12% Are Doing This.
• 7 Culture Practices Worth Stealing
• Podcast Episode: How WBN Is Becoming an AI-First Company

More About Rob Levin & WorkBetterNow

Like this show? Click on over and subscribe to our YouTube channel!
Follow Rob Levin on Substack.
Out now! The New Talent Playbook: The Ultimate Guide to Building Your Dream Team 📕 Available on Amazon or visit thenewtalentplaybook.com and get the free scorecard.