How Was I Supposed To Know That?

Company Counsel - Bernard Williams
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How Was I Supposed to Know That? is a business podcast hosted by Bernard A. Williams that helps entrepreneurs and business leaders avoid costly mistakes by learning from experienced professionals. Each episode explores legal, financial, operational, and growth-related topics through candid conversations, practical advice, and real-world lessons that every business owner wishes they had known sooner.

  1. Oct 4

    Are You Overpaying Property Taxes? Real Estate Tax Overassessment with Carlo Betts

    Most business owners put their real estate tax bill on autopay and never look at it again. Carlo Betts, founder of Rittenhouse Appraisals and Reduxx Group, says that habit is costing companies real money, and it is about to get worse. On this episode of How Was I Supposed To Know That?, small business attorney Bernard A. Williams, Esq. welcomes Carlo Betts back to the show to talk about real estate taxes and real estate as a growth strategy. Carlo explains what an overassessment is, how a property tax appeal actually works (and what happens when a municipality refuses to budge), and why cuts in government funding are pushing more businesses into overassessed territory. The conversation then turns to strategy: how owners use mixed-use buildings and small strip centers to grow from one location to many, why doctors are often risky real estate investors, the one lease clause every small business tenant should ask for, and where the Philadelphia real estate market is headed. If you own or lease the property your business runs out of, this episode is a reason to pull out your last assessment and take a closer look. Chapters: 0:00 Welcome Back, Carlo Betts 1:18 What Reduxx Group Does 3:16 Launching a Second Company While Running the First 5:12 What Is a Property Tax Overassessment? 6:45 How the Real Estate Tax Appeal Process Works 7:18 When a Tax Appeal Goes to Litigation 9:06 Why More Businesses Are Being Overassessed 11:43 Should Every Property Owner Review Their Assessment? 12:18 When You Are Underassessed: Stay Quiet 14:34 Real Estate Tax Mistakes Business Owners Make 15:46 Using Real Estate as a Business Growth Strategy 18:20 First Steps: Define Your Target Market 21:12 When the Real Estate Strategy Goes Wrong 22:52 Why Doctors Make Risky Real Estate Investors 23:49 The Philadelphia Real Estate Market Outlook 26:19 Should Philadelphia Host the Olympics? 29:19 The Future of Homeownership 32:40 Advice for Tenants: Ask for a Right of First Refusal 33:56 What's Next for Reduxx Group Talk to Company Counsel: https://www.companycounsel.law/contact-us How Was I Supposed To Know That? is hosted by Bernard A. Williams, Esq. of Company Counsel, fractional general counsel for small businesses in growth mode. Have a legal question you wish someone had warned you about? Send it our way. #RealEstateTaxes #PropertyTaxAppeal #SmallBusinessLaw #CommercialRealEstate #FractionalGeneralCounsel

  2. Sep 28

    Is Your Company Valuable Or Just Busy

    We break down why “operational friction” quietly drains time, money, and leadership focus, even in companies that look successful on paper. We also lay out how clean processes, clear decision rights, and trustworthy data can raise business value and reduce risk before and after an M&A deal. • Operational friction defined as anything that makes execution harder  • Owner dependency as a growth killer and a valuation risk  • Undocumented processes and inconsistent handoffs as hidden costs  • Single points of failure in small teams and big organizations  • Running the business like it must operate without the owner  • Core workflows, accountability, and decision rights that buyers expect  • Meaningful KPIs and reliable systems and data for due diligence  • Post-close integration ownership, culture, and operating rhythm  • Merger versus acquisition differences in roles, tech, and culture  • A practical AI approach: fix one painful process first  • The “hidden friction tax” exercise to find time and revenue leaks  • Intake as a universal process worth improving They can reach me either by my website, which is thefrictionfixer.com. My email address is Trisha@thefrictionfixer.com. You can also find me on LinkedIn as Trisha Warren, MBA.

  3. Sep 21

    Your Vendor’s AI Can Create Liability For You

    We sit down with technology transactions attorney Pooja Teckchandani to get practical about AI risk for entrepreneurs who are moving fast and shipping products. We break down what “AI” actually means, where liability can hide in vendor terms, and how to ask better questions before a launch turns into a fire drill. • What a technology transactions lawyer does day to day inside a large company • Career lessons from being the first and only in house lawyer at a fast growing brand • The difference between automation, generative AI, and agentic AI • Where AI shows up in real products and back office operations • Why LLM providers can function like subcontractors and what that changes • Data retention, deletion, and security posture questions to ask vendors • How “improvement” language can become a training loophole • Why AI compliance is often state by state and how to track legal updates • Risk decisions when building agents and who owns output responsibility You can go on to my website, which is tech-law.com, T E C K L A W.com or you can find me on LinkedIn.

  4. Sep 14

    Succession Planning Starts The Day You Open

    Your company shouldn’t depend on a single human being to survive a surprise. I sit down with Ivy Slater, CEO of SlaterSuccess.com and author of Best of the Best, to talk about what happens when business gets messy fast: rejected sales calls, thin margins, partnership betrayal, and the moment you realize you need real infrastructure, not just hustle. Ivy shares how she broke into New York City’s printing industry when it was openly a boys’ club, then learned profitability the hard way by digging into overhead and asking “show me the numbers.” We also walk through the day she opened the office door and found half the place emptied out, and why her first moves were practical: protect the checkbooks, call the attorney, call the accountant, call the bank. That experience shapes how she now coaches leaders through partnerships, mergers, separations, and the communication breakdowns that signal trouble. Then we get into the core idea: succession planning is really legacy planning. Ivy explains the “life happens” moments that can hit any founder, why a strong growth strategy doubles as business continuity planning, and how her 365-day vacation thought experiment exposes whether you’re delegating, training your team, and spreading key knowledge across the organization. You’ll leave with a simple planning method that starts with a five-year vision and turns it into 90-day goals, weekly steps, and consistent progress. If you care about small business growth strategy, leadership development, and building a sustainable company, subscribe, share this with a founder friend, and leave a review so more owners can find it.

  5. Aug 20

    Legacy-Proof Your Business

    How Was I Supposed To Know That?

  6. Jul 27

    HR Outsourcing & AI Hiring Risks with Tina Hamilton

    Tina Hamilton, CEO and founder of myHR Partner, joins Bernard Williams to unpack HR outsourcing, the new hiring risks created by AI (including an all-AI reference-check scam), why employment disputes tend to be the most expensive litigation a company faces, and when a workplace issue needs an attorney. Plus Tina's 24-year founder journey: her first staffing franchise, surviving the 2007 crash by pivoting to HR, and why she runs the company debt-free. Learn more about Tina and myHR Partner at myhrpartner.com. How Was I Supposed To Know That? is a podcast for entrepreneurs, by entrepreneurs — hosted by Bernard Williams of Company Counsel.

  7. Jul 20

    Cass Bailey — Growth by Acquisition, M&A Communications & Buyer Due Diligence

    On this episode of How Was I Supposed To Know That?, host Bernard A. Williams talks with Cass Bailey, CEO and founder of Slice Communications, a Philadelphia communications agency that helps high-risk and complex organizations communicate through change, crisis, and opportunity. Cass Bailey shares her accidental path into PR and crisis communications, why she founded Slice in 2008 to bring social media and PR together, and how relentless networking carried the company through the recession. She and Bernard get real about selling the business in 2012, the acquisition that fell apart, and buying her own company back in just 23 days. From there the conversation turns to Slice's growth-by-acquisition strategy: the red-flag/green-flag playbook, why buyer due diligence matters as much as seller due diligence, and why 70-80% of M&A communications should be aimed at internal audiences. If you are thinking about buying, selling, or scaling a company, this one is full of hard-won lessons. In this episode: What Slice Communications does and the crisis calls that come in at 2 a.m.Founding a PR + social media agency in 2008The three reasons M&A deals fall apartWhy internal communications drive M&A successBuyer due diligence: the questions sellers forget to askBuying the company back in 23 daysCass Bailey's acquisition and integration playbookWhat is next for Slice, including AI and executive communicationsConnect with Cass Bailey on LinkedIn (Cass Bailey, Slice Communications). Presented by Company Counsel — fractional general counsel and business law for growing companies.

  8. Jul 13

    Why You're Leaving Money on the Table — with Alex Hayes (Boost Pricing)

    Small business owners obsess over revenue — but Alex Hayes, President of Boost Pricing, says that's exactly the trap. In this episode, Alex joins Bernard A. Williams, Esq of Company Counsel LLC to explain why "revenue is a vanity metric," and why profit margin is the number that actually keeps a business alive. Drawing on 15+ years in sales leadership, Alex unpacks the difference between skill and confidence, why so many owners discount when they don't have to, and how to think about price increases without the fear of losing clients. She shares Boost Pricing's profitability calculator, the "$300-to-$200" discount problem, and why giving work away for free is often better than cutting your rate. For any professional-services owner — law, marketing, consulting — this is a practical, mindset-shifting conversation about charging what you're worth. Guest: Alex Hayes, President, Boost Pricing — alex@boostpricing.com. Ask about the book Fearless Pricing.

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About

How Was I Supposed to Know That? is a business podcast hosted by Bernard A. Williams that helps entrepreneurs and business leaders avoid costly mistakes by learning from experienced professionals. Each episode explores legal, financial, operational, and growth-related topics through candid conversations, practical advice, and real-world lessons that every business owner wishes they had known sooner.

Information

  • Creator
    Company Counsel - Bernard Williams
  • Years Active
    2026
  • Episodes
    17
  • Rating
    Clean
  • Copyright
    © 2026 How Was I Supposed To Know That?
  • Show Website
    How Was I Supposed To Know That?