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 […]

Jocelyn Greenky at the Talent Management Summit 2026 in Dallas discussing leadership, talent, workplace culture and AI.

Talent Management Summit 2026: Leadership, Culture and AI in the Real World

I recently had the opportunity to participate in the Marcus Evans Talent Management Summit 2026 in Dallas, and one of the things I appreciated most was its size. Smaller and more intentionally curated than the typical conference, the Summit gave speakers and attendees time for something increasingly rare at business events: actual conversation. I met […]

Jocelyn Greenky, panelist at the 2026 marcus evans Talent Management Summit in Dallas

Jocelyn Greenky at the 2026 Talent Management Summit: Rebuilding Culture After Change

Sider Road founder and CEO Jocelyn Greenky joined the marcus evans Talent Management Summit in Dallas (September 14–15, 2026, at The Ritz-Carlton Dallas, Las Colinas) as a featured panelist on “Resilient Blueprint: Rebuilding Culture and Engagement in the Aftermath of Change.” Alongside talent leaders from Aimbridge Hospitality and LRS, Jocelyn dug into what it actually […]

Jocelyn Greenky moderating "Architecting the Pipeline" at the 2026 marcus evans Talent Management Summit in Dallas

Jocelyn Greenky Moderates “Architecting the Pipeline” at the 2026 Talent Management Summit

At the marcus evans Talent Management Summit in Dallas (September 14–15, 2026, at The Ritz-Carlton Dallas, Las Colinas), Sider Road founder and CEO Jocelyn Greenky moderated the panel “Architecting the Pipeline: Preparing First-Time Leaders to Excel Amid Uncertainty.” Leading a discussion with senior talent executives from Cisco, Comcast, and International Motors, Jocelyn pressed into one […]

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 Great Wealth Transfer’s Women Problem Isn’t Money

Of the $124 trillion changing hands over the next couple of decades, about $47 trillion is heading to women. A Forbes piece last month put its finger on the part everyone else is celebrating past: wealth can change hands without power changing hands. Reader, I have seen this movie. A daughter inherits the shares. Her […]

New Podcast Feature: Jocelyn Greenky on Building Businesses, Masterminds, and Meaningful Conversations

Jocelyn Greenky, Founder of Sider Road, joined Mike and Zach on the SaveToZero podcast for Episode 21 — and let’s just say 42 years of experience gives you a lot to talk about. The conversation covered what corporate giants, entrepreneurship, academia, and family business consulting actually teach you over four decades. The big takeaway? The […]

Your name on the door is not a legacy. It’s a liability.

Most founders say they want to build something that lasts. What they’re actually building is a business that can’t function without them. If every real decision still runs through you — that’s not legacy. That’s a hostage situation. The next generation doesn’t fail because they lack talent. They fail because they were handed titles without […]

The Founder Is Not the Succession Plan

Most family businesses do not have a succession plan. They have a founder who plans to leave someday. Those are not the same thing. The founder may know who should take over. The next generation may already have an impressive title. The family may have discussed the future over dinner. But until authority, accountability, ownership, […]

Why the World’s Strongest Family Businesses Don’t Try to Act Corporate

For decades, family businesses have been advised to “professionalize”—to adopt corporate structures, bring in outside leadership, and reduce the influence of family in decision-making. The assumption has been that family involvement introduces risk. But some of the most successful companies in the world challenge that thinking. Hermès, for example, has remained firmly family-controlled while building […]

From NASCAR to Your Business: What Happens When Succession Goes Wrong

I can’t stop myself from commenting on all these family run companies—which btw—are the cornerstone of every town, city, state and country in the world. Bar none. Family Business literally rule. Dale Earnhardt Sr. built one of the most iconic brands in NASCAR history. Then he died. And his widow took over (3rd wife). What […]

Air Canada C.E.O. to Step Down Amid Backlash Over Comments After Crash —– An entire lifetime of hard work to have his reputation trashed in seconds.

Two pilots lost their lives. Families were grieving. And the CEO’s response became the story. Not because of what he said — but HOW he said it. Michael Rousseau stepped down after backlash to a condolence message delivered almost entirely in English, in a country where language is identity, culture, and respect. Let’s be clear: […]

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