business
business · EN-US
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.
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Contact path
Verified email
Booking probability
29%
Guest openness
Selective
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Signup to Generate a PitchHow 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.
Recent episodes include "Are You Overpaying Property Taxes? Real Estate Tax Overassessment with Carlo Betts" (4 October 2026, 36 minutes), "Is Your Company Valuable Or Just Busy" (28 September 2026, 42 minutes), and "Your Vendor’s AI Can Create Liability For You" (21 September 2026, 34 minutes).
How Was I Supposed To Know That? publishes roughly weekly, with episodes averaging 37 minutes across 17 episodes.
Booking probability for How Was I Supposed To Know That? is 29%, and the host is rated Selective on guests. How Was I Supposed To Know That? requires a Pod Score of 80 or higher. How Was I Supposed To Know That?'s contact route on record: verified email.
The strongest fits for How Was I Supposed To Know That? are Business & Management Consulting and Law & Legal Services. How Was I Supposed To Know That? has a business audience.
How Was I Supposed To Know That? is a business podcast with 17 episodes published.
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How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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 Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
How Was I Supposed To Know That?
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...
Recent guests on How Was I Supposed To Know That?. Study who booked and why before you pitch.
Author of ”Best of the Best: Lead Boldly, Scale Rapidly, Create Your Leg..., Slater Success Coaching
powerlifting coach, Harris and Hayes
new associate head baseball coach and assistant athletic director of external affairs, Hoover Spine and Relief Now Laser Birmingham
Founder and Principal Ally, Beholder Agency
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