How Was I Supposed To Know That?

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

July 20, 2026 42 mins

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 relen...

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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 owner...

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June 1, 2026 33 mins

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.

W...

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May 31, 2026 40 mins

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 mult...

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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,...

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May 31, 2026 36 mins

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...

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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 Wi...

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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 t...

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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 thinki...

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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 spec...

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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 rai...

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