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.

Episodes

  1. 2d ago

    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.

  2. 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.

  3. Jun 1

    M&A Contracts Made Simple

    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.

  4. May 31

    A Business Valuation Starts Every Serious Deal

    The fastest way to lose leverage in an acquisition talk is to walk in with a fuzzy idea of what your business is worth. We sit down with forensic accountant Allie Aldrich of Turning Numbers to get practical about business valuation in the M&A process, from the first documents a valuator requests to the real reasons a price goes up or down. If you’ve ever heard someone say “just use a multiple” and felt uneasy, this conversation gives you a clearer, more defensible path.  We talk through what a valuation is really measuring and why it becomes the backbone of negotiations. Allie explains the standard inputs valuators rely on, including three to five years of financial statements, tax returns, and corporate or LLC paperwork, plus a detailed questionnaire that surfaces risk factors like customer concentration, debt structure, and owner perks. We also dig into “textbook clean” books versus the messy reality of many small businesses, and how normalization adjustments can change earnings by backing out perks or correcting owner pay to a market-rate replacement cost.  Because Allie brings a forensic background, we also explore what happens when valuations uncover red flags, why secure document sharing matters, and why buyers often want a valuator who knows how to find skeletons. You’ll hear why founder dependence can shrink enterprise value, how a calculation of value can help you plan before a sale, and how concepts like goodwill and intangible value are still evolving in the valuation world. Subscribe, share this with a founder who’s thinking about selling, and leave a review with your biggest valuation question.

  5. May 31

    Exit Planning For Small Business Owners

    Most business owners work for years to build something valuable, then guess at what it’s worth when it’s finally time to sell. That guess can cost you real money. We sit down with business broker and M&A advisor Hitash Patel of TransWorld Business Advisors to get practical about exit planning for small business owners and what actually drives a strong business sale. We talk about when to bring a broker into the conversation, why the best time to think about an exit is earlier than you think, and how a business valuation can double as a roadmap. Hitash explains how he looks beyond financial statements into operations, legal readiness, and the transferability of the business. We also tackle the word everyone throws around but few define clearly: multiples. Instead of treating a multiple like magic, we break it down as risk assessment, including owner dependence, customer concentration, and what buyers worry about when they take over. From there, we walk through the real mechanics of taking a company to market: using a teaser to protect confidentiality, requiring NDAs, vetting buyers, and building a Confidential Information Memorandum that tells the company’s story with the data to back it up. If you’ve ever wondered how buyers are found, how serious buyers are separated from curious clickers, or how to sell on your timeline instead of in distress, this conversation lays out the playbook. If this helps you, subscribe, share it with a fellow owner, and leave a review. What part of selling a business feels most uncertain to you right now?

  6. May 31

    Growth Marketing For A Higher Exit

    If you’re aiming for a “happy exit” someday, you can’t rely on vibes, likes, or a handful of referrals and hope a buyer sees the same value you see. We sit down with Craig and Emilia Andrews of Beholder Agency to unpack how growth marketing can increase small business valuation by building real assets: clear positioning, a website that converts, and distribution channels you own. We get specific about the difference between advertising and marketing through the owned, earned, and paid model. Paid media (PPC, Meta ads, LinkedIn ads, geofencing, streaming TV) can accelerate growth, but it also exposes a brutal truth: if revenue stops when the ads stop, you don’t have a durable system. That’s why we dig into frameworks that connect sales goals to marketing strategy, with metrics that matter for M&A like qualified leads, conversion rates, and customer lifetime value. We also hit the mistakes we keep seeing in the real world, from vanity metrics that only feed ego to messaging that confuses the market (yes, we talk about the “sushi at a gas station” problem). And because growth can create risk, we cover compliance and legal basics, including AI content pitfalls, brand guideline violations, and why your privacy policy and terms of use need regular attention. If you want marketing that builds valuation instead of noise, subscribe, share this with a founder who’s thinking about selling, and leave a quick review so more business owners can find the show.

  7. May 31

    How To Value A Small Business Before You Buy

    Most small business owners dream about the day they sell, but the market doesn’t care about dreams. A company is only valuable if it can be verified, financed, and operated without the founder holding everything together. That’s why we sat down to talk about acquisition entrepreneurship, the buy-side path that flips the usual startup story and forces you to think like a buyer and a lender from day one. Bernard Williams, a small business owner and attorney focused on helping companies grow and plan for exit, and I’m joined by Ben Smith, an acquisition entrepreneur who left a long career in IT consulting to acquire a logistics company. Together, we unpack what buyers actually look for: clean financials, realistic EBITDA, smart valuation multiples, and enough cash flow to cover overhead and SBA loan debt service. Ben shares how he modeled 40 to 50 opportunities, narrowed them to a short list, and learned to watch for hidden owner expenses that inflate a profit and loss statement. Then we get into the part that rarely makes it into “how to buy a business” checklists: people, culture, and customer trust after closing. Ben explains why he wanted the sellers to stay on for a transition, how core values guide hiring and firing, and what happened when experienced staff walked out the door and service quality slipped. If you’re considering buying an asset-heavy business, we also cover a key risk most first-time buyers underestimate: fixed asset condition, maintenance cycles, and surprise repair costs. Listen, share this with someone thinking about a small business acquisition, and if you found it useful, subscribe and leave a review so more buyers and owners can find the show.

  8. May 31

    The Deal Gets Easier When The Owner Lets Go

    A business can look wildly successful on the outside and still be “not ready” the moment you try to sell. We sit down to unpack the uncomfortable gap between what owners think buyers will pay for and what the market actually rewards, especially when risk shows up during due diligence. If you care about getting the best outcome for your money, your people, and your legacy, this conversation is for you. We get specific about deal structure in mergers and acquisitions, including why earnouts are so common, how buyers use them to protect against uncertainty, and why they can become a mess once the seller gives up control. We also talk through a popular private equity approach, the equity rollover, and how staying invested can create alignment and a real “second bite at the apple” when the next exit happens. Along the way, we zoom out from pure valuation and focus on the total package that determines what you actually take home. Then we go to the root issue that quietly drives price cuts and tougher terms: owner dependency. If your top customers only trust you, or your team can’t operate without you, buyers see risk and will structure the deal accordingly. We share practical ways to reduce that risk by building leadership depth, documenting processes, cleaning up financial reporting, addressing customer concentration, and thinking like a buyer who asks, “How do you double this business in three years?” We also tackle the emotional side, including fear near closing and how a founder’s identity can derail a great deal at the last minute. If you’re thinking about selling a company or planning an exit strategy, subscribe for more conversations on M&A readiness, deal terms, and building a business that can thrive without you. If this helps, share it with a founder friend and leave a review. What part of selling a business feels most intimidating right now?

  9. May 31

    The Emotional Side Of Selling A Business

    Selling your business can be the proudest moment of your career and also one of the most emotionally complicated. We talk about the part founders rarely plan for: the identity shift, the protective instincts, and the unexpected grief that can show up right when the numbers say you should be thrilled. I’m joined by Jonathan Peters, senior partner at Empirical Consulting Solutions, to break down how operator-first thinking changes the way you prepare for a lower middle market transaction. We dig into the difference between working in the business and working on the business, why buyer confidence depends on a management team that can run without the founder, and how that independence can directly impact your valuation multiple. We also get tactical on exit readiness and M&A preparation 18 to 24 months before a potential sale: balance sheet cleanup, obsolete inventory, accounts receivable aging, predictable revenue and earnings, gross margin discipline, and customer concentration risk. Then we zoom out to the softer factors that can make or break a deal, including culture, employee retention, customer stickiness, and the real-world limits of your team’s capacity to “fix everything at once.” If you’re a founder, owner, or advisor thinking about exit planning, business valuation, or small business M&A, listen, share it with a partner, and subscribe so you don’t miss the next one. After you listen, leave a review and tell us what exit readiness challenge you want to hear us tackle next.

  10. May 31

    The Exit Mindset

    Most founders say they want an exit. Far fewer talk honestly about the moment you realize your partners are no longer aligned, your lead pipeline is changing, and the business you built is quietly becoming harder to carry. We’re joined by Angela Poynton, a Philadelphia marketing leader who launched her agency in 2017, navigated a partner buyout, and later sold the firm after taking it to market and sorting through multiple offers. We unpack what happens when a partnership that once solved business development starts to shift, and how learning sales, networking, and visibility becomes essential for agency growth. Angela also shares how she built the support system she needed: mentors, EO and EO Accelerator peers, and the professionals who helped her stay steady through an emotional, high-stakes decision. From valuation disagreements to bank financing and personal guarantees, we get specific about the mechanics of a partner buyout and the reality of running a services business where “sweat equity” eventually turns into real dollars. Then we walk through the M&A process for a marketing agency: deciding to sell while performance is strong, choosing between private equity and strategic buyers, living through months of due diligence, and designing a transition that protects clients, team members, and your own next chapter. If you’re thinking about a business exit strategy, selling a services business, or preparing your company for acquisition, you’ll leave with clearer trade-offs and a more realistic path forward. Subscribe, share this with a founder who’s building for an exit, and leave a review with the biggest question you have about selling your business.

  11. Mar 25

    The Quiet Work That Maximizes Your Exit Value

    Ready to sell your business without leaving money on the table or inviting a post-closing headache? We break down due diligence in plain English and show how early preparation turns chaos into clarity, protects your price, and shortens the path to a clean exit. With partner and M&A attorney John Thielen from Company Counsel, we dig into what buyers actually look for, how documents get reviewed, and why the right systems can raise your valuation. We start by defining due diligence beyond buzzwords: the structured exchange of financials, contracts, leases, corporate records, and proof your operations work without you. John explains how letters of intent set the stage, why LOIs are mostly nonbinding but still shape exclusivity and expectations, and how diligence windows typically run 30 to 45 days. We explore deal mechanics like purchase price adjustments tied to findings, escrow holdbacks, and the hidden friction of third-party consents such as landlord approvals and contract assignments. From there, we map a prep plan owners can follow months or even years in advance. Build a central repository for everything: formation documents, cap tables, tax returns, client and vendor contracts, employment and contractor agreements, IP assignments, SOPs, and HR policies. Document how work gets done, from onboarding to delivery to invoicing, so buyers see a transferable machine rather than a founder-dependent practice. We also tackle the myth that skipping diligence saves time. In reality, poor prep invites delays, lower offers, and expensive litigation later. Whether you are eyeing an exit in two years or two months, this playbook helps you organize, disclose, and negotiate with confidence. If you want to pressure-test your readiness, set up a legal audit and get your checklist moving now. Subscribe for more owner-first conversations, share this with a founder who’s thinking about selling, and leave a review to tell us what part of the exit process worries you most.

  • 11 Episodes

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
    11
  • Rating
    Clean
  • Copyright
    © 2026 How Was I Supposed To Know That?
  • Show Website
    How Was I Supposed To Know That?