Sider Road

I love reading the WSJ…. but —– the WSJ article was just wrong (link below)

Calling GEORGE Magazine a “bust” is just wrong. I know—because I had a front row seat. At the time, I was running domestic digital editorial operations for Hachette Filipacchi Médias, including GEORGE. Let’s get the facts straight: • Launched in 1995 • Turned a profit in year one • Reached 400,000+ paid readers • Scaled […]

$815,000

That’s the price tag on watching TV in the back office while your family business pays you to be mayor. Meet John Vassilaki — former mayor of Penticton, British Columbia, and newly minted poster child for why “he’s family, we’ll figure it out” is not a governance strategy. The B.C. Supreme Court just ordered him […]

$133 BILLION. That’s how much the Estée Lauder empire is worth.

And yet… the fourth generation can’t agree on what to do with it. Here’s a masterclass in how NOT to run a family business: 🔴 Step 1: Build something legendary (great job, Estée) 🔴 Step 2: Hand it to your kids (fine, still okay) 🔴 Step 3: Hand it to THEIR kids (getting spicy) 🔴 […]

Reputation is built in silence. It is lost in a soundbite.

What Timothée Chalamet’s town hall disaster teaches every business leader — including the ones who think they don’t care about any of this. There is a particular kind of reputation damage that does not arrive with warning. It does not come from a scandal, a lawsuit, or a product failure. It arrives in a single […]

We’re Blaming the Wrong Generation

Stop Blaming Gen Z. Look In the Mirror. Are these kids showing up to job interviews high? Genuinely asking — because I personally know CHROs who get calls from parents when their adult child gets feedback at work. As in, a grown person received constructive criticism from their employer and their mom picked up the […]

The Tisch Family Just Showed Us Everything Wrong With How Family Businesses Handle Succession

The New York Giants are worth $10.1 billion. The Tisch family has owned half of them since 1991. And it took an Epstein scandal to force a succession plan into motion. Let that sink in. This week, Steve Tisch — along with his siblings Jonathan and Laurie — formally requested the NFL’s approval to transfer […]

A family business just sued itself. And it’s only the beginning

One branch of a family that built a Yonkers coffee roasting company together — from the ground up — is now asking a judge to force the whole thing closed. Why? The other branch allegedly placed a family member on the payroll who never worked there. Not a day. Not an hour. Possibly to inflate […]

The bravest thing Jay Graber did at Bluesky wasn’t building it. It was knowing when to stop running it.

Most founders cling to the CEO title like it’s the prize. It’s not. It’s a job. A very specific, often brutal job — and it has almost nothing to do with why most founders started building in the first place. Jay Graber just did something the startup world rarely celebrates: she looked in the mirror, […]

Damon Whiteside just stepped down as CEO of the Academy of Country Music. Now, here’s a dude I can R-E-S-P-E-C-T.

On paper it looks clean. The numbers are clean. Six and a half years. Profits up 150%. Membership at an all-time high. He even said it himself: “I’ve really accomplished what I wanted to accomplish here.” And he meant it. According to his own Billboard interview, there was 100% staff turnover during his tenure. A […]

Women Behind (and Often Leading) the Family Business

Family businesses rarely fail because of numbers. They fail because of unresolved people dynamics. If you work inside a family business, you already know this—even if no one has ever said it out loud. The hardest moments don’t come from spreadsheets. They come from conversations that never quite happen, roles that are never clarified, and […]

Family Work Culture: China, Hong Kong, Singapore, Turkey, Pakistan and Venezuela

Many different types of work cultures Family culture is characterized by a strong emphasis on hierarchy and orientation to the person. The result is a family-type environment that is power-oriented and headed by a leader who is regarded as a caring parent and one who knows what is best for the per- sonnel. Trompenaars found […]

Be Relevant: What You Need To Know And Why

Here’s a tip #102, when meeting with a Spanish speaker.  Be able to introduce yourself, “Me (MEH) llamo (YA-MO)  ______.” My name is _____. It sends a message that you care and took five seconds to learn out to speak their native tongue. “Nunca(Noon-Ka)  sabes (SA-BAYS) quien (KI-EN) conoceras (Co-No-Sa-Ras)”. You never know who you’ll […]

Succession Without Sabotage: How Family Businesses Can Transfer Power Without Destroying Trust, Talent, or the Company

Succession planning is the Achilles’ heel of most family businesses. Everyone knows it’s coming, but few know how to handle it without burning bridges. The Common Pitfalls Avoidance: no one wants to talk about Dad retiring.  Favoritism: heirs are chosen based on relationships, not readiness.  Sabotage: family members undercut each other to secure power.  What […]

Three Decision Traps Family Businesses Fall Into (and How to Escape Them)

Family businesses are powerful engines of wealth and legacy—but they’re also minefields of decision-making drama. After decades of coaching and consulting, Jocelyn has seen the same traps pop up again and again. The good news? Once you name them, you can escape them. Trap 1: Consensus Paralysis When every family member needs to agree, nothing […]

How MBA 101 Training Supercharges Team Efficiency (Without the Ivy League Price Tag)

Think MBA thinking is just for suits and spreadsheets? Think again. Today’s smartest organizations from fast-scaling startups to legacy family-run businesses are going all in on one game-changing idea: Business fluency isn’t just for the C-suite anymore. It’s for everyone. And that’s exactly where MBA 101 training comes in. No soul-crushing tuition. No endless semesters. No jargon-for-jargon’s-sake. […]

Family Business Crisis Never Knocks It Crashes Through the Door. 5 Mistakes That Can Worsen the Situation (And How to Avoid Them)

How you respond in the first 24–48 hours can make or break your company’s future. Data breach? PR disaster? Market disruption? Internal scandal? The pressure to act fast is real but speed without strategy is a trap. At Sider Road, we’ve worked alongside leaders in the heat of major crises. And we’ve seen even the smartest […]

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