Trimaran Advisory Group

09/24/2026

When you're starting out, you might think that other successful business owners have the answers.

But after decades of working with entrepreneurs, I've learned something different.

Some of the best decisions are made without knowing exactly how things will turn out.

You gather the information you can.

You listen.

You ask thoughtful questions.

You seek advice.

And then you make the best decision you can.

Sometimes it works.

Sometimes it doesn’t.

Either way, you learn from what happens next.

That isn’t weakness. It’s judgement.

Yet when it comes to the next generation, we often try to protect them from making mistakes. In doing so, we may be robbing them of the experiences that build confidence, resilience and wisdom.

Failure isn’t shameful.

It’s experience—if we are willing to reflect on it and learn from it.

And perhaps one of the most valuable things an entrepreneur can pass to the next generation isn't a list of answers. It's an understanding of how to think when there isn't an obvious answer.

Because the next generation will face circumstances you've never experienced.

What remains valuable is the ability to think critically, stay curious, listen to others, take thoughtful risks, and keep moving forward when the path isn’t clear.

Maybe the goal isn’t to give the next generation all the answers. Maybe it’s to give them the confidence to find their own.

09/17/2026

We spend a lot of time talking about the challenges of building a successful family business.

But there's another conversation we don't have often enough:

What happens when you actually succeed?

The business grows.

The family becomes financially secure.

Opportunities that once seemed impossible become possible.

And that's something worth celebrating.

But success introduces a different kind of complexity.

Children may grow up with opportunities their parents never had. Their relationship with money—and with work—may be very different.

Expectations can change.

And the definition of "enough" can become less clear.

Sometimes, the values that helped build the business can become blurred once financial pressure is no longer driving every decision.

Success creates a different set of questions.

What does work mean when you don't have to work?

What does responsibility mean when you've never had to worry about financial security?

How do you teach gratitude without manufacturing hardship?

How do you give the next generation opportunity without taking away their sense of purpose?

These aren't financial questions.

They're human questions.

And for families who have successfully built significant businesses, they may be among of the most important questions of all.

When financial security is no longer the goal, what becomes the goal?

09/03/2026

If you had to score your family enterprise today, what would you give it?

Not just the business. The whole family enterprise.

Maybe the financial side would score a 9.

● Revenue is strong.
● Profitability is healthy.
● The business is growing and creating long-term value.

But what about everything that doesn’t appear on the financial statements?

Trust.
Communication.
Relationships.
Shared values.
Prepared owners and leaders.

Can your family have difficult conversations?
Are roles, expectations, and decision-making responsibilities clear?
Can you disagree without damaging important relationships?
Is participation based on contribution?
Are family members placed in roles based on capability, experience, and fit? Or are employment and leadership opportunities sometimes treated as a right of ancestry?

Is the rising generation being prepared?
Do they understand the values, stories, sacrifices, successes, and failures that shaped the enterprise?
Are there rules to invite family members to work, manage and own shares in the family business?
And what if their calling lies somewhere else?

Success does not require every family member to enter the business.

It may mean giving them the confidence and freedom to pursue a meaningful path on their own.

We often measure what is easiest to measure.

But are we measuring what matters most?

If you scored your Family Business Enterprise today…

Where would you give yourselves the highest marks?
Where would you find there is work to do?

The number is not the final answer.

It is the beginning of a conversation.

Coming next:
The Three Scorecards of Family Business Enterprise Success

08/27/2026

What conversations are you avoiding?

Most family business challenges don't begin with poor intentions.

They begin with postponed conversations.

"We'll talk about it next year."
"They already know what I want."
"Now isn't the right time."

Until one day...

Time runs out.

The strongest family enterprises don't avoid difficult conversations.
They have them early.
With respect.
With clarity.
With purpose.

Ask yourself:

What conversation have you been postponing?
Who needs to be part of it?
What would happen if it never took place?

The conversations you avoid today often become tomorrow's biggest challenges.

08/20/2026

What are you waiting for?

Most business owners delay planning because everything is going well.
Ironically…
That's exactly when planning should happen.

Not because you expect something to go wrong.
But because you have something worth protecting.

Ask yourself:

If something unexpected happened tomorrow…

Would your family know your wishes?
Would your business know the path forward?
Would your advisors know how to work together?

Planning isn't preparing for disaster.

It's protecting everything you've worked so hard to build.

The best time to plan isn't after life changes.
It's before it does.

08/19/2026

Building a business takes years of hard work, sacrifice, risk, and countless decisions. But protecting what you’ve built requires just as much thought and intention.

I was recently a guest on the Glovisor Podcast, where Joe Abreu and I had an important conversation about family business succession, legacy planning, and preparing the next generation for what comes next.

One of the biggest takeaways is that traditional estate planning isn’t always enough. Wills, trusts, and tax strategies are important—but so are the conversations about money, values, expectations, relationships, responsibility, and the future.

For family business owners, the business isn’t just an asset. It can represent generations of work, sacrifice, values, and dreams.

The goal shouldn’t simply be to leave wealth behind.

It’s to leave the next generation with the knowledge, values, communication, and confidence to carry it forward.

If you own a business or are part of a family business, I believe this is an important conversation to have—and the sooner, the better.

Thank you to Joe Abreu and the Glovisor team for having me.

🎙️ Listen to the full episode:

What happens to your wealth when you're no longer around to protect...

08/18/2026

What stories haven’t you shared?

Every successful family business is built on stories.
The victories.
The setbacks.
The difficult decisions.
The relationships.
The values.

Yet many founders unintentionally leave out one important part...

The failures that taught them resilience.

Without those stories, the next generation often only sees success—but never understands how hard it was to achieve.

Ask yourself:

What stories have shaped your leadership?
What failures became your greatest teachers?
What wisdom do your children or future owners still need to hear?

Businesses are transferred through documents.
Legacies are transferred through conversations.

08/13/2026

If you stepped away for 30 days…what would happen?

August often provides something business owners rarely experience…
Perspective.

So here's a question worth asking:
If you stepped away from your business for 30 days, what would happen?

Would your team confidently make decisions?
Would your family know your wishes if something unexpected happened?
Would your advisors know who to call and how to work together?
Or would everything simply wait until you returned?

One of the greatest measures of leadership isn't how indispensable you are.

It's how resilient your business becomes without you.

Leadership builds a business.
Continuity ensures it lasts.

08/10/2026

"We thought we had more time."

It's a sentence we've heard more than once with clients.

And behind those words is usually a story.


A business owner who planned to have a conversation with their family next year.
A partner who assumed everyone understood the plan.
A family who believed they were on the same page, until they discovered they weren't.

The reality is that most challenges come from good people who have tunnel vision on running their business today, leaving the hard conversations for ‘another day’.

However, the conversations we postpone today can become the challenges our families and businesses have to navigate tomorrow.

We've seen the difference it makes when families and advisors come together early:

• Expectations become clearer.
• Future leaders feel more prepared.
• Families understand each other's goals.
• Businesses become stronger and more resilient.
• Difficult decisions become thoughtful decisions instead of urgent ones.

Every business represents years of sacrifice, commitment, and belief.

The people behind that business deserve more than a plan sitting in a drawer.

They deserve to understand it.
They deserve to be part of the conversation.
They deserve the opportunity to move forward together.

So today I leave you with this big question: What big conversations have you been avoiding, and is it smart for the health of your business and family to continue to leave things unsaid?

This month, let’s tackle some of the most important questions we ask business owners like you…

07/30/2026

Summer has a way of slowing us down.

Whether we're sitting by the lake, travelling with family, or enjoying a quieter pace, July often gives us the opportunity to reflect on conversations we rarely have time for during the rest of the year.

One of the most important—and often most challenging—conversations within family enterprises is the conversation about fairness.

At first glance, fairness seems straightforward.

Yet within families, fairness is rarely experienced in exactly the same way by everyone involved.

Each family member brings their own experiences, expectations, contributions, sacrifices, and perspectives.

As a result, what feels fair to one person may not feel fair to another.

What appears fair on paper may not always feel fair in real life.

And what is equal is not always perceived as fair.

These differences are not unusual.

They are the reality of every family system.

The challenge is that fairness is often discussed as though it were an objective fact, when in reality it is frequently influenced by personal experiences, emotions, expectations, and individual perspectives.

This is why conversations about fairness can become difficult.

Often, the issue is not the decision itself.

It is the meaning people attach to the decision.

The conversation may appear to be about money, ownership, inheritance, compensation, or opportunity.

But underneath, it is often about something much more human:

Recognition.
Contribution.
Belonging.
Respect.
Understanding.

That is why I often encourage families to slow down before rushing to conclusions.

To become curious about perspectives that differ from their own.

To ask questions before defending positions.

And to consider that another person's experience may be valid even when it is different from their own.

When families are willing to stay in these conversations—even when they are uncomfortable—they often discover that the issue is not simply about what is fair.

It is about understanding what matters most to the people involved.

Sometimes the goal is not to make everyone agree.

Sometimes the goal is to ensure everyone feels heard.

Because while life is not always equal and outcomes are not always identical, families can often accept difficult decisions when they understand the reasoning behind them and feel respected throughout the process.

The strongest family enterprises are not those that avoid difficult conversations.

They are the ones that have the courage to engage in them with curiosity, respect, and a little humility.

This summer, consider asking yourself:

When I think something is unfair, am I evaluating the situation from today's reality—or from my own personal lens and experiences?

Because understanding another perspective does not require agreement.

But it often creates the clarity needed to move forward together.

And perhaps that is where fairness begins.

“Equal is a calculation. Fairness is a conversation.”