Your Holiday Binge List Just Might Save Your Business
Seven shows where shortcuts became lawsuits—and what to audit in your business before January 1st.
In this edition of The Loophole:
Why billion-dollar companies and solopreneurs make the exact same legal mistakes (just with different zeros)
Seven binge-worthy shows where someone skipped the boring legal work—then paid for it
The year-end legal audit prompt that might save you six figures (copy, paste, fix)
The Year-End Scramble
December is when everyone wants to clean house before January 1st. Contracts that were “good enough” in March suddenly need review. Marketing claims that felt like standard hype now look like potential liability.
Most of the problems I’m helping clients fix now could have been prevented months ago—whenever they first felt that tiny twinge of “should I get this in writing?”
My mission before the end of the year is to make my client’s 2026 drama-free.
But it’s the holidays! While I have my head down cleaning up legal messes, I hope my business-owning peers are taking some time to relax. If you’re like me, though, you like to watch some edutainment in between all the feel-good classics with the family.
So my mission for this newsletter: Fill your holiday with lots of drama. Drama on the small screen, that is.
Here’s my challenge: watch something this holiday that might save your business six figures in legal fees.
The Pattern in Every Founder Story
I’ve been thinking about a pattern I see in movies about businesses: the legal procrastination that eventually catches up with everyone.
Every business drama tells the same story: Someone skipped the foundational legal work.
Things scaled.
Then the shortcut became drama.
Some of my favourite famous business drama stories sound eerily similar to the drama that’s come through my desk this year.
→ Local beverage company sued after joke in an ad backfires.
→ Treasure hunting partners in dispute over who owns the treasure.
→ Restaurant franchise founders lose millions on verbal royalty agreement.
→ Startup CEO faces fraud charges after product fails to deliver.
→ Real estate company collapses when investors demand financial records.
So while you’re off for the holidays, I’ve got a challenge for you: watch something entertaining that might save your business six figures in legal fees.
This holiday: watch something entertaining that also may save your business
I have seven show suggestions below hand-selected by me to you.
Each of these is fun to watch. Each one also sneaks in a little bit of legal education.
This wouldn’t be a good Loophole without some quick, easy, sneaky ways to teach my readers about the law when it comes to their business.
Here’s what to watch—and what to fix in your business before you’re the cautionary tale.
This Pepsi Commercial Cost Them Millions. Is Your Marketing Making the Same Mistake?
Pepsi, Where’s My Jet? (2022)
In 1996, Pepsi ran a television commercial as part of their Pepsi Stuff promotion. The ad showed a teenager landing a Harrier Jet at his high school, with the on-screen text suggesting it could be yours for seven million Pepsi Points. It was clearly a joke—or so Pepsi thought.
John Leonard, a college student, didn’t think it was a joke. He found a loophole in the promotion rules that allowed people to buy points for ten cents each. He raised the money—$700,008.50, to be exact—and attempted to claim his jet. Pepsi refused. Leonard sued.
Pepsi ran the commercial without proper disclaimers. No fine print explaining it was humor. No clear boundary between what was actually available and what was just creative marketing. Just vibes.
The case went to court, where judges had to decide a surprisingly complex question: was this an enforceable offer or just “puffery”? The answer hinged on what a “reasonable person” would believe. Would a reasonable person think Pepsi was actually offering a $23 million military aircraft? The court said no. But the case still cost Pepsi time, money, and reputation—all because they didn’t add a simple disclaimer.
As a lawyer, I love the lessons on how to advise clients to treat ads, promos, and influencer claims like legal commitments; get clear about what is and isn’t being offered; document terms and limitations in plain language—not buried in a PDF nobody reads.
It makes business owners think about:
Your sales pages: Are you making promises you can’t keep?
Your marketing claims: Would a reasonable person think that’s guaranteed?
Your disclaimers: Are they actually visible, or hidden in fine print?
Watch: Pepsi, Where’s My Jet? (2022). Watch on Netflix.
Two Partners Found Gold. Only One Kept It. Here's What They Forgot to Document.
Gold (2016)
There’s a particular kind of business relationship that feels solid until money arrives. The handshake deal. The partnership based on trust. The verbal agreement that “we’ll figure out the details later.”
Gold tells the story of a modern treasure hunt—a partnership formed on optimism, big dreams, and almost no documentation. When the gold is discovered and the money starts flowing, something predictable happens: trust evaporates. Competing narratives emerge. Suddenly nobody can prove what was actually agreed to.
As a lawyer, I love the lessons on how to advise clients to never treat optimism as due diligence; define who owns what, who decides what, and how profits are split; assume every deal needs a paper trail when big money is involved.
It makes business owners think about:
Partnerships and collaborations: Is everything in writing?
Verbal agreements: Do you have any? Get them documented now.
Profit splits and ownership: Could you prove your deal in court?
Watch: Gold (2016). Watch via rent/buy and streaming options.
Ray Kroc Made One Promise Outside the Contract. It Changed Everything.
The Founder (2016)
Ray Kroc didn’t invent McDonald’s, but he scaled it. The McDonald brothers created the system—the efficient kitchen, the limited menu, the replicable model. Kroc saw the franchise potential and convinced them to let him run with it.
At some point in the deal-making, Kroc apparently made a promise to the brothers: they’d get a royalty on all future franchises. It was a side deal. Outside the main contract. The kind of promise that feels solid when everyone’s excited about the partnership.
As a lawyer, I love the lessons on how to advise clients to ensure every material term belongs in the signed deal; protect brand control and core assets before scaling; understand how leverage shifts once growth is underway.
Business owners can learn the moment a “side promise” is made outside the contract, and how power and paperwork, not fairness, decide who wins.
It makes business owners think about:
Side agreements: Have you made promises outside your contracts?
Scaling plans: Are your terms locked down before you grow?
Brand and IP control: Who actually owns what you’re building?
Watch: The Founder (2016). Watch via streaming and rent/buy options.
How to Build a $9 Billion Fraud (Just Skip These Four Things)
The Dropout (2019 podcast)
Elizabeth Holmes built Theranos on a simple, compelling promise: a revolutionary blood-testing technology that could run hundreds of tests from a single drop of blood. Investors poured in hundreds of millions. The company reached a $9 billion valuation. Holmes appeared on magazine covers.
There was just one problem: the technology didn’t work.
As a lawyer, I love the lessons on how to advise clients to build a culture where people can flag red flags safely; treat investor updates as legal documents, not hype; in regulated industries, make compliance and quality control first-class systems.
It makes business owners think about:
Marketing vs. reality: Can you prove every claim you make?
Internal documentation: Would your files help or hurt you in court?
Compliance systems: Are you gambling in a regulated space?
Listen: The Dropout (2019 podcast). Listen on major podcast apps (ABC News).
WeWork Had a $47B Valuation Until Investors Asked One Question
WeCrashed (2020 podcast)
WeWork’s story is less about fraud and more about something equally dangerous: a massive governance gap. The company built a billion-dollar valuation on narrative, charisma, and the promise of transforming commercial real estate. When it came time to go public, the IPO process required detailed disclosures.
That’s when the problems surfaced.
As a lawyer, I love the lessons on how to advise clients that strong governance is not optional at scale; manage conflicts transparently or they will manage you; assume fundraising and public filings turn your operations into a legal record.
It makes business owners think about:
Governance structure: Can it survive outside scrutiny?
Conflicts of interest: Are you creating hidden liabilities?
Financial records: Would they hold up to due diligence?
Listen: WeCrashed (2020 podcast). Listen on Wondery and major podcast apps.
Your Employment Contract Might Own What You’re Building Right Now”
Silicon Valley (2014–2019)
Silicon Valley is a comedy, but the legal issues driving the plot are real. The show opens with a central question that terrifies every founder: who actually owns the code?
Richard Hendricks builds Pied Piper while employed at another tech company. His employer, Hooli, immediately claims they own the intellectual property. The question comes down to tiny facts: When was it built? Where? Using what resources? What did Richard’s employment agreement say about IP created on company time?
The show exaggerates for comedy, but the core issues are real. Employment contracts often include broad IP assignment clauses. “Company time” can be interpreted more broadly than you think. And term sheets—even ones that say “non-binding”—create expectations and sometimes obligations.
As a lawyer, I love the lessons on how to advise clients to read their employment IP clauses before building anything on the side; document invention timelines and contributions.
It makes business owners think about:
Your employment agreements: What IP clauses did you sign?
Side projects: Do you actually own what you think you own?
Term sheets and LOIs: Are you treating them casually? Don’t.
Watch: Silicon Valley (2014–2019). Watch on Max or Crave in Canada, plus purchase options.
The One Thing May Make Your Contracts Unenforceable (Even If You Paid a Lawyer to Write Them)
Let’s Simplify Legal Jargon (2010 TED Talk)
Most legal disasters aren’t dramatic. They’re boring. They happen because nobody understood what they were agreeing to.
Designer Alan Siegel makes a compelling case in this TED Talk: legalese and dense forms don’t just annoy people—they create avoidable conflict. When customers can’t understand your terms of service, they don’t follow them. When employees can’t parse your policies, they don’t comply. When contracts are unreadable, disputes multiply.
As a lawyer, I love the lessons on how to advise clients to think about how layout and wording change behavior. Clear language doesn’t just make people feel better—it makes them more likely to comply, less likely to misunderstand, and less likely to sue. Clarity is risk management.
It makes business owners think about:
Your contracts: Can your customers actually read them?
Your terms of service: Are they designed to confuse or clarify?
Your internal policies: Do people understand what’s required?
Watch: Let’s Simplify Legal Jargon (2010 TED Talk). Watch on TED or YouTube (TED channel).
What to Do Before January
If you plan to take some time off and find yourself turning your mind to your business over the holidays, trust me, you’re completely normal.
If you laugh when people call it ‘holidays’, also totally normal.
Before January I’d advising thinking about cleaning your legal house – you dont need a lawyer.
Pick one item from the lists above to think about. Just one.
Fix it before the year ends.
A little secret most law firms won’t advertise? The best time to handle legal clarity is before you need a lawyer.
Copy and paste this into your AI tool of choice to get a personalized audit of what to fix before January 1st.
I'm a solopreneur running a [describe your business type and what you sell].
Here's what I'm currently doing in my business:
- Marketing channels I use: [list them - social media, email, ads, etc.]
- How I work with clients: [contracts, proposals, terms of service, or informal agreements]
- Partnerships or collaborations: [describe any, or say "none currently"]
- Intellectual property I've created: [courses, content, software, designs, etc.]
- How I handle payments and refunds: [describe your process]
- Disclaimers I currently use: [list them, or say "none"]
Based on these common legal vulnerabilities:
1. Marketing promises without proper disclaimers
2. Verbal agreements and undocumented handshake deals
3. Side promises made outside of written contracts
4. Gap between marketing claims and actual capabilities
5. Weak governance and undisclosed conflicts of interest
6. Unclear intellectual property ownership
7. Contracts and terms that customers can't understand
Give me a prioritized list of 3-5 specific legal issues I should address before the end of the year. For each issue, tell me:
- What the risk is
- What to document or clarify
- A simple first step I can take this week
Be direct and specific to my business model.And on that note, I’m taking a few days off over the holidays. I’m writing it on my calendar: No computer, no work.
My goal is to show up calmer, clearer, and more creative in 2026. Because when I’m rested, I negotiate better. I scope projects better. I spot red flags faster. And I stop saying yes to things I should decline.
Let’s maximize our rest so we can have a great 2026.
Build smart,
Sonya
P.S. If you watch or listen to any of these, please let me know. I’d love to know how they came about or if they inspired you to make any changes in your business.
“If you laugh when people call it ‘holidays’, also totally normal.” Hahahaha! Loved this.
I’ve enjoyed many of these films and podcasts too - and I’m bookmarking “Gold”! Thanks for the recs. Sound advice as always(clear legal language FTW)!