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How Was I Supposed To Know That?

How Was I Supposed To Know That?

By: 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.

© 2026 How Was I Supposed To Know That?
Economics Leadership Management & Leadership
Episodes
  • Cass Bailey — Growth by Acquisition, M&A Communications & Buyer Due Diligence
    Jul 20 2026

    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 2008
    • The three reasons M&A deals fall apart
    • Why internal communications drive M&A success
    • Buyer due diligence: the questions sellers forget to ask
    • Buying the company back in 23 days
    • Cass Bailey's acquisition and integration playbook
    • What is next for Slice, including AI and executive communications

    Connect with Cass Bailey on LinkedIn (Cass Bailey, Slice Communications).

    Presented by Company Counsel — fractional general counsel and business law for growing companies.

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    42 mins
  • Why You're Leaving Money on the Table — with Alex Hayes (Boost Pricing)
    Jul 13 2026

    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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    32 mins
  • M&A Contracts Made Simple
    Jun 1 2026

    Most founders think selling a company is about agreeing on a price. Then the documents show up, and suddenly the deal feels like a maze of acronyms, redlines, and “standard” clauses that don’t feel standard at all. We sit down with attorney Jon Thielen, partner at Company Council, to translate the legal side of mergers and acquisitions into clear, practical steps you can actually use as a buyer or seller.

    We walk through the M&A process from the first real document, the letter of intent (LOI), through due diligence and into the purchase agreement that ultimately governs the transaction. You’ll hear what typically belongs in an LOI, how exclusivity periods and confidentiality can become binding early, and what “redlining” really means when lawyers start negotiating language. We also talk about how to protect sensitive financial data during a small business sale, including limiting access and using secure document portals.

    Then we get specific about the contracts that decide who owns what and who pays when something goes wrong: asset purchase agreement versus stock purchase agreement, representations and warranties, disclosure schedules, assignment and assumption agreements for key contracts and leases, purchase price allocation for tax purposes, and indemnification provisions that allocate post-closing risk. We also cover common add-on documents like promissory notes for seller financing and employment agreements when the seller stays on during a transition period.

    If you’re preparing for a business acquisition, planning an exit, or just trying to understand M&A contracts without the legal fog, this conversation will save you time and stress. Subscribe, share this with a founder who’s heading toward a deal, and leave a review with the one contract question you want us to tackle next.

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    34 mins
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