Sider Road

Your Business Outgrew the Backyard. Did Anyone Tell the Neighbors?

A family-run car dealership in the Scottish Highlands is fighting its local council to stay open.Angus MacKillip has run Horsepower Cars since 2015, from land next to his home. He’s been a licensed dealer since 1991. Now his licence renewal is headed to a council hearing in late October, after objections he says he only […]

You Don’t Lose the Family Business in a Fight. You Lose It in the Paperwork.

A headline in my inbox this week stopped me cold. A family business had already changed hands entirely before anyone noticed. What gave it away? A letter from the accountant. From what I could see, the parents were too exhausted by the conflict to force their son to the table. And legally, he held all […]

The CEO Just Left. Who’s Running Things on Monday?

This week, Roger Lynch announced he’s leaving Condé Nast after seven and a half years to run Mattel. Vogue, GQ, Vanity Fair, and now Barbie. I spent a good part of my career in the magazine business, so I read his goodbye memo the way some people read box scores. Here’s what jumped out at […]

Family Business Succession: The Most Expensive Breakfast | Sider Road

The Most Expensive Breakfast in Family Business History Larry Miller was very good at his job. As a young parts manager, he took one car dealership’s parts department from 961st in the country to No. 1 in just 28 months. He was promoted to operations manager for five dealerships. Then the owner invited him to […]

Family Business Succession: What NYC’s Grocery Fight Reveals

A family grocery store can survive a Costco opening down the block. It can survive COVID. It can survive inflation, thinning margins, and a changing neighborhood. But can it survive a competitor that doesn’t have to make money? That’s the question playing out in New York right now. Family-owned bodegas and grocers are challenging the […]

Reputation Is a Shared Asset With an Unshared Downside

The Met board approved it. Anna Wintour is wearing it. That’s the whole lesson, and it’s worth a minute of your time even if you couldn’t care less about fashion. Quick recap, per NPR: in late July the Met announced a spring Costume Institute show honoring John Galliano, the designer whose 2010–2011 antisemitic remarks are […]

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, […]

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 […]

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