AI Without the Intimidation—Takeaways from our latest Breakfast Club
Artificial Intelligence can feel like a tidal wave—fast-moving, powerful, and a little overwhelming. At EFBC’s recent Breakfast Club, AI: Your New Office BFF, members gathered to explore that wave together.
Here are the biggest takeaways from the event:
1. “I thought I could opt out of AI… until I couldn’t.”
Patty Rioux, President of Odea and co-founder of Trybl, opened with honesty and humor. Like many of us, she assumed AI was something she could avoid—or at least leave to someone else on her team. That changed the moment a client used ChatGPT to generate branding ideas and came back with AI-generated icons. “I think we can all agree… they were horrible,” she said, laughing.
But that moment was also pivotal. “It was our first AI-generated client input,” she shared. “And that’s when I realized—I wasn’t going to opt out before this hit my company.”
Instead of resisting, Patty’s team leaned in. They started experimenting—not just with marketing tools, but with operations and internal workflows. She reminded us that AI isn’t just about being tech-savvy, It’s about being adaptable, curious, and open to change.
2. Shared experience > advice
One thing that makes EFBC unique is its commitment to learning through shared experience. In Patty’s words: “In our Forums, we don’t give advice—we share what we’ve been through. And this presentation is no different.”
That mindset shaped the entire event. There were no AI evangelists telling people what to do. There were people sharing what they’ve tried, what worked, what didn’t, and what they’re still figuring out. And that made all the difference.
Whether you’re just starting to explore AI or you’ve already integrated tools into your business, your perspective has value. EFBC is a space where those experiences are heard and honored.
3. AI is already changing how industries operate
Ryan Williams from PSM Partners shifted the lens to a broader view. He highlighted how AI is already embedded in industries we interact with every day—often without us even noticing.
“That’s AI listening. It’s transcribing the visit and doing the backend documentation so doctors can focus on you—and see more patients.”
It’s a powerful reminder that this isn’t some futuristic idea. AI is already here, behind the scenes, saving time and boosting efficiency. And the same is becoming true across sectors—from law to recruiting to logistics.
4. Start small, think smart
Two of Trybl’s founders—JJ Lattea, and Hassan Momin—walked us through their real-world experiments with AI, showing how they’re using tools like ChatGPT, Midjourney, and Figma AI plugins to support their creative process.
- JJ showed how AI can rapidly prototype visual concepts, saving hours in the design phase.
- They emphasized the storytelling side of design, using AI to map out user journeys and generate language that speaks to target audiences.
- Hassan brought the technical lens, sharing how they’re building internal tools and workflows powered by AI to streamline collaboration and handoffs.
Their advice? Don’t try to boil the ocean. Pick one part of your workflow that feels repetitive or messy—and test AI there.
What stood out was how naturally AI fit into each person’s workflow. Not as a replacement, but as a thought partner. A brainstorming buddy. A second set of hands when you’re short on time.
5. The future is collaborative—and a little messy
From mic issues to system crashes, the irony of hosting a tech event with tech struggles wasn’t lost on anyone. But it also reinforced a core truth: trying something new is always a little messy. And that’s okay.
The room was full of members who weren’t afraid to admit what they didn’t know. Who asked hard questions. Who laughed when things didn’t work perfectly. And who walked away inspired to try something anyway.
Final Thoughts
This event wasn’t about becoming AI experts—it was about starting the conversation. Together, we explored how AI is already showing up in our businesses, how it can support creativity and efficiency, and how we can begin to experiment in ways that make sense for us.
Thank you to our strategic partners, PSM Partners and ODEA, for helping bring this event to life. A special thanks to the team at Trybl for sharing your tools, process, and perspective. And to our EFBC members, thank you for showing up with curiosity, honesty, and a willingness to learn.
See you all at the next event!
EFBC President’s Message: Clarity
Dear EFBC Members,
I am back with another themed letter, and this time I am thinking about Clarity.
In business, we often strive for growth, efficiency, and opportunity. But there’s another factor that plays a critical role in our success – Clarity.
It’s not just about knowing when things are going well – it’s about understanding the full picture, even when the news isn’t ideal. We all know that we live in an ambiguous world, but that uncertainty can slow us down. Clear answers, good or bad, allow us to act with confidence.
Take the recent back-and-forth on tariffs. Regardless of the impact on your business, positive or negative, the most challenging aspect for me has been the daily back-and-forth and unexpectedness. Once we have clarity, we can plan much more effectively. We might not like the answer, but at least we know how to move forward.
I’ve also recently experienced this in my own business while evaluating a large transaction. Very recently, there were still many unknowns. But after a key discussion, the options became clearer. And while that development wasn’t all positive, the clarity itself is a win – it removes guesswork and allows for decisive action.
So, I’ve been making an intentional effort to get clarity. One of our Core Values at Specialty Sales is Honesty and Transparency, which can seem obvious – “Don’t lie”. But more importantly, we seek clarity in our communications with our customers, vendors and partners. We communicate clearly and ask direct, clear questions to have more effective relationships and conversations.
As we navigate our businesses going forward, I encourage all of us to seek clarity – in our decisions, our strategies, and our conversations. Once we see the path ahead, we’re already in a stronger position.
As a reminder, the EFBC is celebrating our 30th anniversary this year, and GALA REGISTRATION IS OPEN. I am looking forward to seeing you all there.
Warm regards,
Darrin Shillair – EFBC President 2024-2025
How to Get the Next Generation Excited About the Family Business
Engaging the next generation in the family business isn’t just about handing over the reins—it’s about inspiring curiosity, purpose, and connection. For many families, ensuring that G5 (the fifth generation and beyond) is excited and invested in the business is one of the biggest challenges.
At our recent Women in Family Business event, held in partnership with the Loyola Family Business Center, we explored how to cultivate that engagement in a way that feels natural, meaningful, and rewarding.
Amelia Patel, Chief of Staff at LDI, shared valuable insights on how her family business fosters excitement and involvement among G5. It’s not just about preparing them for leadership—it’s about creating opportunities for them to engage early, aligning their roles with their passions, and emphasizing the impact the business has on both the family and the community. From mentorship programs to innovation projects, the key is to make G5 feel valued and empowered—on their own terms.
Start Early and Make It Meaningful
One of the biggest takeaways from the discussion? Start them early. Waiting until the next generation reaches adulthood to introduce them to the family business often makes the transition feel forced rather than organic. Instead, businesses should create touchpoints for involvement throughout childhood, adolescence, and young adulthood—without overwhelming them.
At LDI, the family hosts an annual retreat, which was originally designed to bring everyone together while incorporating business education. However, after receiving feedback, they discovered that many next-gen members felt the retreat leaned more toward a business conference than true family bonding. This raised an important question: What does next-gen education really look like?
The answer is different for every family, but a key approach is balancing structured learning with organic engagement. Rather than making business discussions feel like formal obligations, they can be woven into family experiences in ways that spark interest and build relationships.
Play to Their Strengths
Another important takeaway is meeting G5 where they are. The next generation isn’t a monolith—some may be naturally drawn to leadership, while others might prefer supporting roles that align with their unique skills. That’s why playing to their strengths is crucial.
- Are they into computer science? Let them redesign the company website or explore ways to optimize digital operations.
- Passionate about storytelling? Encourage them to help with social media, create video content, or manage the family business’s online presence.
- Do they love numbers? Involve them in financial planning discussions or let them analyze business trends.
By giving G5 real, tangible ways to contribute, their involvement shifts from an expectation to an opportunity. They start to see how their skills can directly impact the business, making them more likely to stay engaged over the long term.
Engaging Even the Youngest Family Members
One of the most exciting parts of the conversation was about engaging even the youngest members of G5. Business involvement doesn’t have to wait until they’re old enough to take on formal roles—there are creative ways to introduce them to the family business at an early age.
Amelia shared that she’s even used ChatGPT to brainstorm ideas for introducing family business concepts to kids in fun, interactive ways. These might include:
- Gamifying business lessons, such as creating a mock business where kids can “run” their own small projects.
- Creating leadership challenges that encourage teamwork and problem-solving.
- Finding ways to connect their interests back to the family business, whether it’s through art, technology, or even philanthropy.
By making the learning process engaging, hands-on, and age-appropriate, families can instill a sense of curiosity and belonging from an early stage—which can make all the difference in whether they see the business as a meaningful part of their future.
The Big Picture
Ultimately, getting G5 excited about the family business isn’t about pushing them into leadership—it’s about showing them why the business matters. Whether it’s through family history, innovation, or community impact, the goal is to help them see their place in the larger story.
When the next generation feels a sense of ownership, purpose, and alignment with their passions, engagement happens naturally. The key is to start early, play to their strengths, and continuously evolve the way families introduce business involvement to keep it relevant and exciting.
How does your family business cultivate excitement in the next generation? Let’s keep the conversation going.
EFBC President’s Message: Resilience = Success
Dear EFBC Members,
I am back with another themed letter, and this time I am thinking about Resilience.
Running a business isn’t for the faint of heart. It takes grit, adaptability, and – sometimes most importantly – resilience. The reality is stark: about 20% of small businesses don’t make it past their first year, and 70% fail within a decade. But those that survive aren’t just lucky – they’re resilient. Sometimes the key to outperforming your competitors is just to outlast them.
So, how do we build that resilience? A few key things make all the difference:
- Plan for the Unexpected – Have a game plan for downturns and challenges before they hit. I often do scenario planning with my team around big risks, e.g. the loss of a large customer, implementation of punitive tariffs, etc.
- Keep Finances Strong – A financial cushion can be the difference between weathering a storm and closing up shop, and it is prudent to be very careful with debt.
- Stay Adaptable – Markets change, and the most successful businesses evolve with them. We make a strategic plan for the year, but we never hesitate to change it when circumstances demand it.
- Lean on Your Network – Customers, vendors, and fellow business owners are invaluable sources of support and insight. The EFBC and our strategic partners are an invaluable resource for this.
- Keep Learning – The best leaders never stop looking for ways to grow and improve, whether it’s from their EFBC Forum or one of our many educational events.
Challenges will come, but they don’t have to define us. What matters is how we respond. By staying prepared, connected, and open to change, we not only survive—we thrive.
Here’s to the resilience that it takes to build businesses that stand the test of time.
Speaking of Resilience and organizations that have stood the test of time, the EFBC is celebrating our 30th anniversary this year, and GALA REGISTRATION IS OPEN. I am looking forward to seeing you all there.
Warm regards,
Darrin Shillair – EFBC President 2024-2025
What No One Tells You About Selling Your Business
Selling a business is often seen as a strategic and financial decision—one defined by contracts, valuations, and negotiations—yet it is just as much an emotional and psychological journey.
At EFBC’s February 13th Fireside Chat, seasoned business leaders Jim Flanagan and Mark Wesa shared their firsthand experiences in selling their companies. Jim Flanagan, the former CEO of Nuance Solutions, and Mark Wesa, the former owner of MKD Electric, have both navigated the complexities of business sales in recent years.
Although they anticipated challenges in their M&A journeys, they encountered many unexpected surprises along the way.
Here’s what they—and many other business owners—wish they had known before stepping into the world of mergers and acquisitions.
1. The Emotional Toll is Real
No matter how prepared you are, selling your business isn’t just about the numbers—it’s about identity, legacy, and years of hard work.
Jim and his brother agonized over the decision, asking themselves, “How much risk do we want to take at this point in our careers?” Many business owners face the same struggle: logic vs. emotion, what’s best for the business vs. what feels right personally.
Deanna, EFBC member and chat moderator, summed it up perfectly:
“Deciding to step away from a business is truly a head vs. heart decision.”
The process can be exhausting, and when emotions take over, it becomes harder to stand firm on important terms.
Takeaway: Acknowledge the emotional weight early. Surround yourself with trusted advisors to stay grounded.
2. The Deal Isn’t Final Until It’s Final
A signed Letter of Intent (LOI) does not guarantee a sale.
The speakers recalled “11th-hour” situations where terms were renegotiated at the last minute—even after an LOI was finalized. This happens more often than most sellers expect.
Takeaway: Expect changes. Have a contingency plan, and ensure all verbal promises are put in writing.
3. Trust is Essential—But Not Always Enough
Even well-meaning buyers may struggle to uphold commitments due to market conditions, leadership changes, or financial challenges. Jim put it simply:
“In reality, what’s in writing is just on paper.”
Takeaway: Trust is important, but so is legal protection. Work with experienced advisors and push for contract transparency.
4. Keeping Quiet Can Be Critical
Mark stressed the importance of keeping acquisition talks private until a final decision is made.
“Don’t put your team on the emotional rollercoaster unless you’re certain it’s happening.”
Premature discussions can create unnecessary stress. Employees may start looking for new jobs, clients may get uneasy, and competitors may exploit the uncertainty.
Takeaway: Share information strategically. Until the deal is confirmed, limit discussions to those who absolutely need to know.
5. Define Your Non-Negotiables Early
Having clear guardrails—on culture, employee retention, leadership roles, operating systems or brand legacy—can prevent regret. Jim recalled Mark mentioning this concept at an EFBC meeting, emphasizing how it helped him maintain clarity.
Takeaway: Establish non-negotiables before negotiations start. Write them down and revisit them often.
6. Get Every Verbal Promise in Writing
Many sellers assume that once a deal is signed, everything will go as planned, but that is rarely the case.
Mark admitted:
“If I could do it differently, I would get all verbal promises in writing.”
Jim agreed:
“Same!”
Takeaway: Never assume verbal agreements will be honored. Get everything in writing—and be prepared to hold buyers accountable.
7. Private Equity: A Common Buyer with High Turnover
Many business owners sell to private equity (PE) firms, which are among the most active buyers in the M&A space. But PE firms have high turnover.
Statistically, the people you negotiate with may not be the ones leading the company post-sale—or even through the entire process. This creates unexpected challenges, especially when new decision-makers shift priorities.
This turnover can also mean verbal agreements or assurances may not hold up under new leadership. The individuals who promised to maintain company culture or protect employees might not be around to enforce it later.
Takeaway: If selling to private equity, expect leadership turnover. Get every commitment in writing, and don’t assume the people you’re negotiating with will be the ones executing the plan.
8. EFBC’s Impact: Having the Right People in Your Corner
One of the biggest challenges of selling a business is navigating the unknown. Having a trusted network of advisors and peers makes all the difference.
Mark described EFBC’s impact as invaluable:
“The advice and experience I received from my EFBC forum was very powerful during this time.”
Forum members who had already been through the process helped him anticipate challenges, evaluate offers more critically, and make better decisions.
Takeaway: Surround yourself with a strong support system. Peer networks like EFBC provide real-world insights that can help you navigate both the emotional and strategic complexities of selling a business.
Final Thought: Selling a Business is More Than Just a Transaction
Selling a business isn’t just about valuation and deal structuring—it’s about relationships, emotions, and unexpected hurdles. The more prepared you are for the hidden challenges, the smoother the transition.
If you’re considering selling, learn from those who have been through it. Their experiences might just save you from surprises down the road.
Want to connect with business owners who have firsthand M&A experience?
Join EFBC to gain access to a network of peers who have navigated the same journey.
Kevin Halbert’s Path to Business Ownership
EFBC MEMBER SPOTLIGHT
Kevin Halbert built his career in strategy and management consulting, helping large enterprises tackle complex challenges. But he wanted something more—an opportunity to take ownership of decisions and see their impact firsthand. That opportunity came with Winkler Tree, where he transitioned from advising businesses to leading one.
We are proud to have Kevin as a member of the Entrepreneur and Family Business Council. We reached out to him to gain insights into his path to business ownership, learning how he has navigated the challenges of entrepreneurship while embracing the impact his business has on the urban landscape.
From Consultant to Business Owner
Kevin spent years solving complex business problems across industries, particularly in mining and chemical production. While he valued the intellectual challenge of consulting, he wanted to take on a role where he could see the long-term impact of his decisions.
“I enjoyed tackling new problems with new clients, but was often frustrated by the lack of long-term ownership over the results of our work. We would typically make a recommendation, launch the initiative, and then move on to another client or issue,” Kevin shared. “I wanted the chance to be the principal decision maker who would have to live with the pros and cons of my own decisions and actions. Owning and operating my own business has certainly been that!”
Overcoming the Learning Curve
Stepping into the tree care industry as an outsider wasn’t easy. Earning trust—from both employees and industry peers—took time, effort, and patience.
“I understandably faced a lot of skepticism from both employees and industry peers,” Kevin admitted. “The only way to resolve that was through time and effort, but it certainly wasn’t easy to build the experience and trust right out of the gate. I’m grateful to a lot of exceptional teammates and industry peers for giving me a chance to learn and earn their trust.”
Beyond relationships, the operational side of running a small business also came with challenges.
“I had a broad background in finance and operations, but had never worked in a small business where people and process issues are just different from those in large enterprises,” he explained. Over time, he built the experience and network needed to make more confident decisions. “You develop a network of ‘go-to’ people for different issues, which makes it a lot easier and faster to make better decisions.”
Growing a Legacy
For Kevin, tree care is more than just a business—it’s about making a lasting impact on the environment and the community. The trees Winkler cares for today will shape the urban landscape for generations to come.
“We’re a team of tree lovers, and the trees themselves are the legacy we hope to leave behind. We’re proud to play our small part in creating and maintaining a healthy urban forest, populated by people who appreciate it,” he said.
Not everyone sees tree care as a priority—some see it as a task to check off a list. But for those who recognize the beauty and importance of trees, Kevin’s team is eager to help.
“I think most people subconsciously get a lot of positive benefits from trees, even if they don’t notice or think about them very often. Next time you’re outside, take a moment just to notice the volume of trees in our region. Try to imagine your neighborhood if all of the trees were gone. Their absence would be striking, and they’d be greatly missed.”
Proud to Have Kevin in Our Community
At EFBC, we are proud to have Kevin as part of our community of business leaders. His dedication to learning, adapting, and making a meaningful impact—both in his business and in the environment—exemplifies the drive, resilience, and leadership that define great entrepreneurs. We look forward to supporting his continued growth and celebrating the lasting contributions he and Winkler Tree Service are making to our local landscape.
Read Kevin’s full interview:
Q: What drew you to transition from your previous career to business ownership?
I spent the previous 10 years as a strategy and management consultant for large enterprises, working across a broad range of industries, though primarily focused on mining and chemical production. I enjoyed tackling new problems with new clients, but I was often frustrated by the lack of long-term ownership over the results of our work.
We would typically make a recommendation, launch the initiative, and then move on to another client or issue. The role was primarily focused on influencing decision-makers, but I wanted the chance to be the principal decision-maker—someone who had to live with both the pros and cons of my own decisions and actions. Owning and operating my own business has certainly been that!
Q: What were some of the challenges you faced during the transition?
The list is long! As an outsider entering the tree care industry for the first time, I understandably faced a lot of skepticism from both employees and industry peers. The only way to resolve that was through time and effort, but it certainly wasn’t easy to build the experience and trust right out of the gate. I’m grateful to a lot of exceptional teammates and industry peers for giving me a chance to learn and earn their trust.
Another big challenge was simply how long it took to solve problems I had never faced before. I had a broad background in finance and operations, but I had never worked in a small business where people and process issues are just different from those in large enterprises.
Over time, you start to build some pattern recognition, and you also develop a network of “go-to” people for different issues. That has made it a lot easier—and faster—to make better decisions.
Q: What legacy do you hope to leave as the owner of Winkler Tree?
We’re a team of tree lovers, and the trees themselves are the legacy we hope to leave behind. We’re proud to play our small part in creating and maintaining a healthy urban forest, surrounded by people who appreciate it.
Some people, of course, view tree care as a necessary burden they have to deal with, and we’re happy to help them through that. But it’s especially rewarding to work with clients who truly appreciate trees and care about maintaining them for the broader community and future generations.
I think most people subconsciously benefit from trees, even if they don’t often stop to notice them. Next time you’re outside, take a moment just to observe the volume of trees in our region. Now, try to imagine your neighborhood if all of the trees were gone. Their absence would be striking, and they’d be greatly missed.
Cray Kaiser White Paper:
Essential Steps to Getting Your Business Ready for a Merger or Acquisition
Preparing to sell your business is a complex process that requires careful planning and strategic decision-making. From getting your financials in order to assembling the right team of advisors, every step plays a crucial role in ensuring a smooth transition.
In this video, Deanna Salo, Managing Principal at Cray Kaiser, shares key insights on what business owners need to consider before an acquisition or merger, helping them maximize value and successfully navigate the journey to their next chapter.
Key Points covered:
- M&A Trends: Business owners are either passing companies to family or selling to third parties (often private equity).
- Preparation Matters: Start early, get financials and processes in order.
- Financial Readiness: Audits and documentation boost credibility for buyers.
- Organizational Clarity: Have a structured leadership chart and clear roles.
- Advisory Team: Lawyers, bankers, and wealth advisors are crucial.
- Valuation Strategy: Market demand, not just retirement goals, determines business worth.
- Confidentiality: Use NDAs before sharing financial info.
- Letter of Intent (LOI): Clearly outline deal terms (price, structure, payment).