Sider Road

Name: Sider Road
Address: Greenwich, CT, US
Telephone: +19178878175

We help family businesses & leadership teams fix operations, align teams, and lead boldly — via masterminds & advisory.

07/21/2026

Great reporting from The Wall Street Journal and Miriam Gottfried this week —

The Wall Street Journal just ran a story about young millionaires buying HVAC and plumbing companies.

Everyone's reading it as a buyer's story.

I read it as a seller's story.

Because every one of those "shortcut to private-equity riches" deals starts the same way:

An owner decided to let go.

A plumber. A manufacturer. A founder who spent 20, 30, 40 years building something real — and had no plan for what came next.

So a stranger with an SBA loan and a Harvard case study became their succession plan.

That's the part the headline skips.

We're in the middle of the largest transfer of business ownership in history. Boomers built these companies. Most never named a successor. Many have no heir stepping up, no plan on paper, no idea what their life's work is even worth.

And into that vacuum walks a 35-year-old "searcher" paying 1.8x EBITDA.
Sometimes that's a great outcome. A skilled operator takes the reins, doubles revenue, keeps the crew employed.

But here's what I want owners to hear:

Your exit shouldn't be an accident of whoever shows up with financing first.
Succession is a decision. Made early. On your terms. With your values, your people, and your legacy in the room.

The searchers in that article did their homework for years.

The question is — did the sellers?

If you own a business and you don't have an answer for "what happens next," that's not a someday problem. That's the most important strategic decision you'll ever make.

Plan it. Don't get planned around.

07/09/2026

So I did a thing. 🎙️

I joined Mike and Zach on Episode 21 of the SaveToZero podcast and we had one of those conversations that goes way deeper than you planned — in the best possible way.

We talked about building businesses, running masterminds, and what 42 years in the trenches really teaches you. Including why fear is the biggest trap business owners fall into, and why family businesses that treat themselves like real businesses — with actual job descriptions, contracts, and honest conversations — are the ones that survive.

Fair warning: I also said some things that will sound very familiar to anyone who has ever sat across a table from me. 😄

▶️ YouTube: https://youtu.be/esGMpFeFaY0?si=riWPLqjyIJQROmml
🎧 Spotify: https://open.spotify.com/episode/4SwM6BmXhZqKqZvrk1rR3b?si=e97eba822d9c4a46
🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/building-businesses-masterminds-and-meaningful/id1895024430?i=1000775771376
🎧 iHeartRadio: https://www.iheart.com/podcast/269-save-to-zero-331045630/episode/building-businesses-masterminds-and-meaningful-conversations-338323904/?embed=true

07/07/2026

Everyone in a family business says they want to build a legacy. Almost nobody does the work it actually requires.

Legacy isn't passing the keys. It's building people who know what to do with them.

That doesn't happen the week before someone retires. It happens through years of real conversations, real authority given to the next generation, and founders willing to admit their role has to change.

Stepping back isn't becoming irrelevant. It's the hardest — and most important — leadership move you'll ever make.

My latest newsletter goes deep on what it actually takes to transfer leadership in a family business. Not the polished version. The honest one.

Read it at SiderRoad.com

05/19/2026

Every leader needs the right room.

For family businesses navigating succession: Family Leadership & Legacy Mastermind.

For women ready to become the authority in the room: The Authority: Women in Business Mastermind.

For CEOs who are successful but stuck: The Scale CEO Mastermind.

Three rooms. Three leadership problems. One purpose: the real conversation.

Learn more: siderroad.com/what-is-a-mastermind

04/14/2026

This is part 2 of a series on reputation in 2026.

04/13/2026

For years, family businesses have been told to “act more corporate.”

But some of the most successful companies in the world have done the opposite.

Take Hermès.

Still family-controlled.
Still deeply rooted in its identity.
Still outperforming competitors—without giving up what makes it a family business.

This isn’t accidental. It’s strategic.

A recent Harvard Business Review article reinforces what many founders get wrong:

Family businesses don’t win despite being family-run.

They win because of it.

Here’s what that actually means:

The things most businesses try to “professionalize away” are often their greatest advantage:

Trust that doesn’t need to be negotiated
Long-term thinking that isn’t driven by quarterly pressure
Relationships built over decades, not transactions

But most family businesses make the same mistake:

They try to look like everyone else.

They dilute their identity.
They overcorrect.
They trade differentiation for imitation.

And in doing so, they lose the very thing that made them strong.
The hard truth:

You don’t need to become less of a family business to scale.

You need to become a better one.

03/27/2026

This is part 1 of a series on reputation in 2026.

03/25/2026

$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 to repay $815K to his own family's liquor store. The highlights reel:

🍺 Collected $108,500 in wages while serving as mayor and physically not being at the store

🌴 Paid family members — including while they were sipping margaritas on a Mexican beach — for hours never worked

📺 Staff described his primary job function as: watching TV in the back office

💸 Used $5K of company funds to pay his personal lawyer in the wrongful dismissal suit he filed against... the company he was stealing from

The court's verdict on his wrongful dismissal claim? Thrown out. His fiduciary duties? Violated. His brother, in a separate case? Also sued him. (Family dinners must be something.)

Here's the uncomfortable truth: THIS IS NOT A CRIME STORY. IT'S A GOVERNANCE STORY.

The warning signs never look dramatic in family businesses. They look like payroll nobody questions. A "manager" who doesn't answer the phone. |

Meetings that never happen. The slow, comfortable blurring of my money and our money.

Until a judge sorts it out at $815K a lesson.

Family businesses are some of the most resilient organizations on earth — and some of the most vulnerable to exactly this kind of slow-burn dysfunction. The fix isn't complicated. But it requires structure, accountability, and someone with the authority — and the nerve — to say: "No. That's not how this works."

That's the work we do at Sider Road. Before it becomes a headline.

WHAT'S THE UNCOMFORTABLE CONVERSATION YOUR ORGANIZATION HAS BEEN AVOIDING? Drop it in the comments — or reach out privately.

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http://www.SiderRoad.com/

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