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.
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 pr...
28 Sept 2026
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 hidd...
21 Sept 2026
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 differenc...
14 Sept 2026
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 digg...
20 Aug 2026
Legacy-Proof Your Business
27 Jul 2026
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 ...
20 Jul 2026
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. S...
13 Jul 2026
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 in...
1 Jun 2026
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 ...
31 May 2026
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 an...
31 May 2026
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....
31 May 2026
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 bu...
31 May 2026
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 th...
31 May 2026
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 ar...
31 May 2026
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 thr...
31 May 2026
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 d...
25 Mar 2026
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 ...
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