WhatKeepsYouAwake.tv

Beyond the Basics: Mark Schwartz on Tech-Driven Finance, Inventory, and Tax Strategy for SMBs

In this advanced follow-up, host David Hooser sits down again with CPA and former attorney Mark Schwartz to dig into the systems that move small and mid-sized businesses from “organized” to “optimized.” What you’ll learn: How to connect your CRM to accounting (e.g., QuickBooks) for real cash-flow forecasting—not just bank balances Inventory intelligence: turnover, just-in-time realities, and choosing industry-specific software Building a clean data pipeline across sales orders, purchase orders, invoicing, and AR/AP Training teams to input the right data (because good data in = good decisions out) Planning working capital: lines of credit vs. credit cards, timing cash cycles, and reading the balance sheet Sales tax automation and quarterly rhythms most owners miss Smart tax moves with a savvy CPA, from timing expenses to leveraging depreciation rules If you’re ready to leverage technology, protect your data, and turn reporting into real decisions, this episode is for you. Subscribe to What Keeps You Awake.tv for more straight-talk strategy from experts who help entrepreneurs win. #MarkSchwartz #SmallBusiness #Entrepreneurship #Accounting #CashFlow #InventoryManagement #CRM #QuickBooks #TaxStrategy #BusinessSystems #DataSecurity #FinancialPlanning #WhatKeepsYouAwake

Mastering Cash Flow & Financial Systems for Small Business Mark Schwartz

In this episode of What Keeps You Awake, host David Hooser welcomes longtime colleague and friend Mark Schwartz, a recovering attorney turned seasoned CPA with over four decades of accounting expertise. Mark shares insights on: Why managing daily cash flow is the #1 concern for entrepreneurs The importance of forecasting and maintaining a strong sales pipeline How to integrate accounting tools like QuickBooks with CRM systems Best practices for purchase orders (PO), sales orders (SO), and invoicing When to outsource bookkeeping vs. hiring in-house staff The essential financial reports every small business should run daily, weekly, and monthly Why “It’s not what you expect, but what you inspect” matters most in business If you’re an entrepreneur or small business owner, this conversation is packed with practical wisdom to help you protect your cash flow, strengthen financial controls, and plan for growth. 👉 Don’t forget to like, follow, and subscribe to What Keeps You Awake for more episodes with experts who help business leaders sleep better at night. #CashFlow #SmallBusinessFinance #AccountingTips #MarkSchwartz #BusinessGrowth #Entrepreneurship #FinancialPlanning #WhatKeepsYouAwake #QuickBooks #SmallBusinessSuccess

Avoid Legal Landmines: Attorney Steven Jacobs’ Playbook for SMBs (Contracts, IP, Data Breach & More)

Small and mid-size businesses face the same legal risks as big companies—just with fewer reps and resources. In this episode of What Keeps You Awake.tv, host David Hooser sits down with attorney Steven Jacobs to unpack the most common (and costly) legal pitfalls SMBs run into—and how to prevent them before they become bet-the-company problems. Steven explains why “buttoning up the holes” matters, how airtight contracts protect revenue, what to know about employees vs. contractors, and why IP, data security, and fast-changing regulations (including AI and employment rules) should be on every owner’s checklist. He also shares practical, budget-smart ways to work with counsel so legal becomes a growth enabler, not just a cost center. What you’ll learn: Why SMBs are vulnerable: fewer repetitions, ad-hoc processes, scattered records The contract basics that save you in court (and help you get paid) Employees vs. contractors: avoiding misclassification traps across states and cities IP protection 101: trademarks, copyrights, patents—and avoiding “borrowed” web content Compliance in motion: how policy shifts and AI rules can hit small teams Data protection and breach response: why investing early (and using a solid MSP) reduces legal exposure Statutes of limitation and record-keeping: how long you’re on the hook—and what to retain Mass arbitration vs. class actions: why prevention beats defense every time If this helped, please like, subscribe, and share with a fellow business owner. Got questions for Steven? Drop them in the comments—we’ll compile and pass them along for a future FAQ episode. #SmallBusiness #LegalTips #Contracts #IntellectualProperty #Compliance #EmploymentLaw #DataSecurity #AIBusiness #Entrepreneurs #SMB #StartupLaw #BusinessGrowth #WhatKeepsYouAwakeTV #StevenJacobs

Scaling Law Firms with AI: Gary Musler on Building High-Performance Legal Practices

In this episode of What Keeps You Awake.tv, host David Hooser welcomes Gary Musler, an expert in building high-performance law firms through AI-driven growth and business optimization. Gary shares how he helps firms move from being people-dependent to process-dependent, using systems and AI tools that create predictable, scalable success. From intake optimization to accountability frameworks, Gary introduces his STAR System, designed to: Treat law firms like sales organizations. Provide proper training and accountability for staff. Maximize ROI on legal marketing spend. Use AI-driven roleplay and feedback to dramatically improve conversions. He also discusses his entrepreneurial journey, the importance of strategy vs. opportunism, and why every firm should operate with a playbook mindset like a championship team. 👉 If you’re running a law firm—or any business that relies on systems and scale—this conversation is packed with actionable insights. For more, visit: scalable.ai And don’t forget to like, comment, and subscribe to stay updated with future episodes of What Keeps You Awake.tv! #GaryMusler #AIForLawFirms #LegalMarketing #BusinessOptimization #LawFirmGrowth #ArtificialIntelligence #STARSystem #SalesTraining #LegalTech #WhatKeepsYouAwakeTV

AI Without Limits: Gerald Hennessey on Building His Own AI Platform for Real Estate & Beyond

In this episode of What Keeps You Awake.tv, host David Hooser sits down with Gerald Hennessey, a master developer who built his own AI system to transform his real estate business—and now pushes the boundaries of what AI can do for small businesses everywhere. Gerald shares how he went from experimenting with ChatGPT to hosting his own AI platform, eliminating latency, reducing failures, and creating human-like customer interactions. He breaks down: Why he ditched third-party AI “bus stops” and built everything in-house. How real estate and service-based businesses can capture 100% of calls with AI. The risks of latency, hallucinations, and downtime—and how to avoid them. Insights on the AI model wars (OpenAI, Meta’s LLaMA, DeepSeek) and the rise of open-source AI. The future of AI + robotics in everyday life and small business operations. If you’re curious about how AI can be customized for real-world business impact, Gerald’s story is a must-hear. 👉 Don’t forget to like, comment, and subscribe to stay updated with the latest episodes of What Keeps You Awake.tv! #ArtificialIntelligence #RealEstateAI #GeraldHennessey #AIForBusiness #Automation #FutureOfWork #VoiceAI #AIChatbots #WhatKeepsYouAwakeTV #OpenSourceAI #DeepSeekAI #BusinessInnovation

AI in Real Estate: Gerald Hennessey on Building a Custom AI Platform for Business Growth

In this episode of What Keeps You Awake.TV, host David Hooser sits down with Gerald Hennessey, real estate entrepreneur and master developer of a fully customized AI system built to transform his business operations. Most people know AI through tools like ChatGPT, but Gerald went a step further — building and hosting his own AI stack to eliminate call center inefficiencies, reduce latency, and capture 100% of inbound leads. He shares how his system streamlines communication across voice, chat, text, email, and web chat, while addressing challenges like hallucinations, downtime, and compliance in outbound calling. 🔑 Key Takeaways: How Gerald identified the flaws of off-the-shelf AI systems and solved them. The importance of reducing latency in real-time customer interactions. Inbound vs outbound AI agents — what works and what doesn’t. Why open-source models like Llama and DeepSeek are game changers. The future of AI in real estate, marketing, and even robotics. If you’ve wondered how AI can directly impact small businesses and real estate, this conversation is packed with insights and practical examples. 👉 Connect with Gerald Hennessey through his website (link in video). 👉 Don’t forget to like, subscribe, and follow What Keeps You Awake.TV for more conversations with innovators and business leaders. #ArtificialIntelligence #RealEstateAI #GeraldHennessey #BusinessAutomation #AIForBusiness #ChatGPT #DeepSeek #OpenSourceAI #RealEstateInvesting #FutureOfWork #SmallBusinessGrowth #AIChatbots #TechInnovation

AI, Marketing, and the R6 Framework: How SMBs Grow Faster with Conversational AI Brian Schreiner

What keeps SMB owners awake at night? For marketing guru Brian Schreiner, it’s staying ahead of AI’s breakneck pace—and turning it into real revenue. In this episode of What Keeps You Awake, host David Hooser and Brian dive into conversational AI, product–market fit, and a proven “6R” framework that boosts revenue before you even buy an ad. You’ll learn how to: • Build AI that sounds like your best salesperson • Capture missed calls automatically (text or voice AI) • Turn reviews and referrals into a growth engine • Reactivate your database for quick wins • Measure what matters so your ad spend isn’t wasted Brian also shares his path from IT consulting and media to launching IgniteBusiness.ai—and why AI won’t replace your team, it will make them unstoppable. Guest Brian Schreiner, Founder, IgniteBusiness.ai Connect IgniteBusiness.ai WhatKeepsYouAwake.tv Freebie mentioned 30-day free Reviews AI install and 30 reviews guaranteed. Visit IgniteBusiness.ai and mention the podcast. #SmallBusiness #AI #Marketing #ConversationalAI #CustomerExperience #SMB #LeadGen #Reviews #ReputationManagement #VoiceAI #Chatbots #Automation #ProductMarketFit #Entrepreneurship #WhatKeepsYouAwakeTV

Managing Risk & Building Community: Insights from Robert Inglhofer

What does it take to successfully manage a high-rise building in the heart of downtown Phoenix? In this episode of What Keeps You Awake.TV, host David Hooser sits down with Robert Inglhofer, Building Manager of 200 East Van Buren, to talk about the day-to-day challenges of operations, supporting small businesses, and mitigating risks in an ever-changing environment. Robert shares what really keeps him awake at night — from ensuring tenants have seamless operations, to the importance of reading contracts thoroughly, to preparing for unexpected challenges like elections, technology breakdowns, and economic downturns. You’ll also hear valuable insights on: Why building managers must think like risk managers The balance between keeping tenants happy and attracting new ones How AI and technology are shaping building management Why contracts can make or break small businesses The importance of finding a landlord who values community, not just the bottom line If you’re a small business owner, entrepreneur, or just curious about what it takes to manage one of Phoenix’s landmark properties, this conversation is packed with lessons you won’t want to miss. 👉 Subscribe to What Keeps You Awake.TV for more conversations with leaders, innovators, and entrepreneurs. #BuildingManagement #SmallBusiness #RiskManagement #PhoenixBusiness #CommercialRealEstate #BusinessGrowth #Entrepreneurship #Leadership #DowntownPhoenix

Why SMBs Need Managed IT: Inside MBPS on Stopping Phishing, Malware & Ransomware

On this episode of whatkeepsyouawake.tv, host David Hooser talks with Austin Johns and Tyler Hooser from MBPS about the real IT risks facing small and mid-sized businesses. They unpack how phishing and social engineering actually hit companies, why every endpoint needs XDR/antivirus, what layered backups look like for fast ransomware recovery, and how to build proactive defenses with permissions hygiene, patching, and Microsoft 365 controls. They also cover the smart uses of AI in security and the privacy guardrails teams should follow when using AI tools. What you’ll learn: • The human side of security: user training and social engineering awareness • Phishing defense: smarter mail filtering and org-level settings in Microsoft 365 • Malware and XDR: why protection must run on every device, on-site and remote • Ransomware readiness: off-site and M365 backups, access control, and recovery playbooks • Proactive vs. reactive IT: monitoring, patching, closed ports, and documented processes • AI in the stack: using AI to defend while protecting sensitive company data About MBPS: MBPS is a people-first Managed IT Services partner that pairs friendly, responsive support with enterprise-grade security practices so issues become opportunities, not roadblocks. Connect with MBPS: Website: mbps.com Email: sales@mbps.com If this helped, please like, follow, and subscribe to whatkeepsyouawake.tv for more practical playbooks that help entrepreneurs sleep better at night. #ManagedIT #SMB #Cybersecurity #Ransomware #Phishing #DataSecurity #EndpointSecurity #Microsoft365 #Backups #IncidentResponse #AI #SmallBusiness #ITSupport #MBPS #WhatKeepsYouAwakeTV

Cash Flow, Funding & Risk: CFO Mark Briden on Smart Financing for Small Business Growth

In this episode of What Keeps You Awake.TV, host David Hooser sits down with Mark Briden, CFO of one of Arizona’s fastest-growing companies, to break down the real-world strategies small and midsize business owners need to manage cash flow, fund growth, and reduce financial risk. With years of experience leading SMB turnarounds and scaling companies, Mark shares: Why cash flow is the #1 thing keeping business owners awake at night How to time your funding before growth opportunities hit so you don’t miss out The role of asset-based lending (ABL) using receivables, inventory, and equipment Risks of overleveraging and how tariffs and market shocks can cripple margins The truth about personal guarantees and how to negotiate them out as your business matures Why trusted advisors (CFO, CPA, lenders, attorneys) should work together—not in silos Mark also gives a practical look at unexpected expenses, alternative lenders, and how to navigate today’s rising bankruptcy and credit risks. 👉 Learn more about Mark’s firm: 360advisor.com 👉 Don’t miss more financial insights for entrepreneurs—subscribe to What Keeps You Awake.TV. #WhatKeepsYouAwakeTV #SmallBusinessFunding #CashFlow #CFOInsights #BusinessGrowth #Entrepreneurship #AssetBasedLending #RiskManagement #StartupFinance #SMBSuccess #FundingStrategies