How Was I Supposed To Know That?
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
11 episodes
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 ...
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 w...
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
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...
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 s...
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 B...
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...
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...
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&...
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 b...
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...