
Hosted by Rob Levin · EN
What separates leaders who scale from those who hit a ceiling? Damon Gersh, founder and former CEO of Maxsens Restorations, has navigated both, building a team that stayed calm and effective during 9/11 and Superstorm Sandy, then evolving from operator to strategist. In this episode, he breaks down the counterintuitive moves that unlock growth: delegating authority before you need it, maintaining non-negotiable standards that attract top talent, and fundamentally shifting from working in your business to working on it. About the Guest Damon Gersh is an entrepreneur best known as the founder and former CEO of Maxsens Restorations, New York's premier property damage restoration firm, which earned recognition for its leadership during 9/11 and Superstorm Sandy. A recipient of the Ernst & Young Entrepreneur of the Year Award, he has co-founded national business organizations including Restoration Affiliates and Gathering of Titans. Now mentoring and investing in entrepreneurs, real estate, and creative ventures, Gersh continues his lifelong focus on leadership, collaboration, and impact. Episode Highlight "A lot of times in life you look back in hindsight, and all the things that you did just moving forward make sense in the rear-view mirror" Actionable Insights Build Your Leadership Team Before Crisis Hits: The preparation work you do in calm times determines your capacity in chaos. By educating his team, delegating authority, and giving leaders room to make mistakes, he built what he calls "decision-making muscles." [02:29] The Leader Sets the Tone, Even When Scared: On crisis days, people are watching you. Gersh was internally uncertain and scared on 9/11, but he knew his job was to project confidence, calm, and control. That psychological anchor, your visible composure, lets your team move into action mode rather than panic mode. [03:41] High Standards Attract High Performers, Culture Self-Selects: Gersh was raised in the old-school service business ethos: all you have is your reputation and good name. He maintained rigorous standards of professionalism and quality, which he embodied as a leader. The result? Top performers wanted to work there. [08:02] Ready to apply these insights to your own business? Download the free Action Kit More About Damon Gersh Connect with Damon on LinkedIn. More Resources Grab your copy of The E-Myth by Michael Gerber 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.
In this episode, Rob Levin breaks down nine foundational practices that separate thriving companies from stuck ones: from leveraging your unique strength to building accountability systems that empower rather than micromanage. If you're frustrated by growing your business but feeling drained in the process, this episode cuts through the noise to show you where the real leverage is. Episode Highlight " If you take care of your talent, they will take care of your clients." Actionable Insights Leverage Your Unique Strength: The work only you can do, where you add value, love the work, and possess irreplaceable skill. But most owners treat it like a luxury. Block time for it relentlessly. Then hire an assistant to eliminate everything else. [01:36] Remove Poor Performers and Fire Poor-Fit Clients Before They Drain Your Team: Poor performers can mean bad attitude or bad capability. Your A players notice who stays and who goes. When you let underperformance slide, you signal that standards don't matter. You also get to choose your clients. Remember: if you don't protect your talent, your clients won't respect them either. [06:30] Continuous Learning Is Your Competitive Moat (Especially in AI): Join a peer group for yourself. Budget time and money for your team to learn new skills. As change accelerates, capability becomes your edge. AI is the obvious case, but this applies across your business. Make it clear: we're investing in your growth. [09:56] Ready to apply these insights to your own business? Download the free Action Kit More Resources: The 3 Things That Separate Business Owners Who Lead from Those Who Just Keep Up Five Talent Changes That Build a Standout Company The Hire That Multiplies Results Without Multiplying Payroll The Best Investment I Make in Myself Every Year Other Episodes You Might Enjoy: 7 Culture Moves Behind a Fast-Growing Company Why Talent Is the New Growth Lever 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.
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 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] 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] 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 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.
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 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] 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] 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] 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 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] 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] 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.
Most companies treat AI as an efficiency play, bolt it onto existing workflows and hope for faster output. Rob Levin went deeper. After recognizing AI's potential in early 2023 and spending two years experimenting, he made a pivotal decision: transform WorkBetterNow into an AI-first company. This isn't about doing the same work faster; it's about redesigning workflows from the ground up where AI does the heavy lifting and humans design and oversee the process. Episode Highlight "Any workflow that can be done by AI, any process that can be done by AI will be done by AI. It's not about evolving an existing workflow, it's about building that workflow from the ground up where AI is doing the work and humans are designing and overseeing the process." Actionable Insights 1. Recognize that AI-first requires a fundamental mindset shift, not incremental tweaking: Rob spent the first two years of AI's emergence running show-and-tell sessions and encouraging experimentation. The breakthrough came after a hands-on AI course where he built an actual business concept and website using AI in two hours. For your team: stop thinking about "how do we do our current work with AI?" Start asking "what workflows would we build from scratch if AI existed?" This distinction unlocks 10x impact rather than 10% efficiency gains. [02:26] 2. Hire or reallocate for AI oversight, not AI replacement: Rob's commitment on day one was clear: no layoffs. What's necessary instead is retraining people to move from "doing work" to "managing AI that does work." WorkBetterNow's IT department showed exactly how this scales: they built an AI chatbot for first-level IT support, which freed the team to focus on automation and integrations—higher-value work. [04:53] 4. Document and share your AI journey so your clients level up too: Rob is doing something rarely seen: instead of hoarding competitive advantage, WorkBetterNow is documenting every AI workflow transformation and publishing it for clients and the broader market. They're also retooling their WBN Academy to include AI enablement. [09:44] Read: Inside WBN's AI Transformation Ready to apply these insights to your own business? Download the free Action Kit 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.
Most business owners are leaving $100,000+ on the table every year doing administrative work that costs $25/hour while their time is worth $200–$1,000+/hour. Rob Levin breaks down why an assistant is no longer a luxury—it's a necessity—and delivers a step-by-step playbook for hiring one, whether full-time, part-time, onshore, nearshore, or offshore. You'll learn to calculate your true hourly rate, identify what to delegate in three days, and avoid the costly mistakes most owners make (like hiring part-time). Within two months of hiring the right assistant, you'll reclaim 16–30 hours per week to spend on growth, customer relationships, and the high-leverage work only you can do. This is Rob's battle-tested framework from 11 years of managing assistants—and having built a company, WorkBetterNow, entirely around helping business owners get great ones. Episode Highlight "If you don't have an assistant, you are one." — Jack Daly Actionable Insights 1. Calculate your true hourly rate and stop doing $25/hour work: Take your target annual compensation (salary + distributions), divide by 2,000 hours, and face the math. Most business owners are worth $200–$1,000+/hour yet spend 40–65% of their time on low-payoff administrative tasks. That $400,000/year owner is literally wasting $160,000 annually on email, scheduling, and document searching. [05:39] Read: The Hire That Multiplies Results Without Multiplying Payroll 2. Plan what you'll do with 16–30 reclaimed hours before hiring: More time is worthless if you don't know how to spend it. Write down your priorities: More customer time? Focus time to think strategy? Family and rest? This clarity motivates you to actually delegate and hire. Dan Sullivan's principle: spend 80% of your time on your unique ability. Assistants make that possible. [10:53] Read: The 3 Things That Separate Business Owners Who Lead from Those Who Just Keep Up 3. Go full-time, even if you think you don't have 40 hours of work: Part-time assistants create gaps where urgent-but-not-important tasks fall back on your plate. You'll find 40 hours of work quickly as you delegate more. Part-timers often leave for full-time roles elsewhere, forcing you to restart. Full-time is the only model that actually works. [12:52] Ready to apply these insights to your own business? Download the free Action Kit 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.
Every headline screams that AI will transform your business overnight. Most SMB leaders find themselves caught between two extremes: either diving recklessly into every new tool, or staying frozen on the sidelines. Ryan Paugh, publisher of Senior Executive and co-founder of Community.co, cuts through the noise with a pragmatic framework that works for small and mid-size businesses. Rather than chasing unicorn-level AI deployment or ignoring the shift entirely, Paugh reveals what the most successful companies are actually doing: staying steady, experimenting in calculated bites, and treating AI adoption as a cultural conversation, not a technology mandate. About the Guest Ryan Paugh is a Publisher, Senior Executive, Co-Founder, President & COO of Community.co, a company that creates vetted communities to help ambitious professionals grow their networks and expand business opportunities. He is also the author of Superconnector: Stop Networking and Start Building Business Relationships That Matter, and a renowned thought leader on creating strong communities and teams. Episode Highlight "The truth lies in the middle. Going crazy off the deep end thinking you need to compete with Fortune 500s on AI, or ignoring it entirely—both are tragic missteps. Stay steady, find ways to make adoption work slowly for your company." (00:03:00) Actionable Insights AI Adoption Isn't Speed, It's Steadiness: Most SMB leaders react to headlines by overcommitting to AI or avoiding it entirely. The real playbook is the middle path: experiment slowly, pick one workflow at a time, and avoid the sunk cost of "solutions that may or may not work." [03:41] Work-Life Blend Beats Work-Life Balance, And It's a Retention Engine: One-size-fits-all employment is dead. Matching how people work to how they want to live isn't benevolence—it's a lever for better talent, lower turnover, and faster growth. [13:00] Over-Communication Isn't Over-Communication in a Remote-First Company: Distributed teams across 35 states and four continents require a different cadence. What feels like repetitive messaging to you is actually the baseline people need to feel connected to mission and to each other. [16:41] Ready to apply these insights to your own business? Download the free Action Kit More About Ryan Paugh Check out Community Co Connect with Ryan on LinkedIn. Grab your copy of Superconnector 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.
Culture isn't a recruitment tactic, it's your competitive advantage. In this solo episode, Rob Levin reveals seven concrete practices that transformed WorkBetterNow into a fast-growing company. You'll walk away with immediately actionable systems: peer-driven recognition that reinforces values and clarity frameworks that eliminate "mutual mystification" (that silent killer of remote teams). Rob draws from hard-won lessons; his first venture failed partly because he deprioritized culture despite knowing better, and shares exactly what changed when he led with core values from day one. Episode Highlight "Recognizing people is just a really easy way to emphasize when people are doing things that are consistent with the culture that you want to have." Actionable Insights Build core values intentionally, they're the foundation for everything else: Start with 4–6 core values developed with your A-players, not handed down from leadership. Use them to guide hiring, recognition, and decisions. At Work Better Now, "Put Talent First" is the first value and shapes every system. Read: This Overlooked Factor Will Add or Subtract Millions From Your Business Install culture practices today: Rob walks through exactly what WorkBetterNow does: recognition (W Awards), humanizing people (My Story presentations), clarity + KPIs, in-person connection, transparency, remote bonding, and continuous education. Pick one and commit to it for 90 days. Read: 7 Culture Practices Worth Stealing Make clarity + accountability your competitive advantage: Avoid "mutual mystification" by using simple frameworks (EOS, KPIs, Rocks). Overcommunicate: video + email. Review progress weekly. This removes friction and builds trust faster than anything else. Read: How to Make Remote Work at Your Company Ready to apply these insights to your own business? Download the free Action Kit to get started. 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.
Innovation isn't the exclusive domain of tech startups, it's the competitive edge every small and mid-size business must build into their DNA. But most owners centralize innovation within themselves, missing their biggest advantage: the ability to move faster than corporations. JL Heather reveals why innovation is fundamentally a cultural challenge, not a structural one. You'll learn concrete steps to build psychological safety, shift from assigning work to assigning problems, and avoid sabotage patterns, especially when integrating AI. About the Guest JL Heather is an innovation coach and co-founder of Centered who has spent 20 years helping teams solve problems faster without enterprise complexity. He specializes in translating agile and design thinking into practical methods for small and mid-size teams where everyone wears multiple hats. His approach cuts through buzzwords to deliver systems that actually work. Episode Highlight "Innovation is just the ability to continually move beyond your customer's expectations, because if all you're doing is meeting those expectations, someone's gonna catch up, someone's gonna surpass you." Action items Culture is where innovation lives, not in separate teams: Leadership sets direction, but culture lives in people. Skip skunkworks models; they disempower everyone else by saying "you innovate, the rest do your jobs." That kills distributed thinking. [00:04:00–00:06:00] Switch from assigning work to assigning problems: Work assignments create doers who avoid trouble; problem statements empower teams to engage their brains. Use design sprints to validate with customers, then build prototypes over 3–9 months. [00:10:00–00:12:00] Don't let tools drive your organization: When adopting AI, resist top-down implementation. Align on what "AI first" means, engage teams in defining how it supports their work, and let them experiment. This takes longer upfront but is vastly cheaper than getting it wrong. [00:21:00–00:25:00] Ready to apply these insights to your own business? Download the free Action Kit More About JL Heather Check out Centered Connect with Mike on LinkedIn. Grab your copy of Breakthrough Innovation Other Resources Check out JL's podcast: Breakthrough Innovation 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.