Scaling the Gap EP 54 | The Greatest Lessons in Leadership from a Second-Generation Family Business

What really makes a leader stand out? Is it just about boosting profits, or is it about something bigger—like inspiring a team, navigating challenges, and leaving a lasting impact?

In this episode of Scaling the Gap, host Madeleine MacRae sits down with Agata Olivieri of Maple Drapery and Carpet to unpack the real essence of leadership. They dive into the ups and downs of running a multi-generational family business, the emotional side of working with loved ones, and the power of self-awareness in decision-making. Agata shares how she and her brother took over the family legacy, why focusing on core strengths (and saying “no” to distractions) is crucial, and how continuous learning fuels long-term success.

If you’re a leader—or aspiring to be one—this conversation is packed with insights on building a strong, accountable team, planning for the future, and redefining success beyond just the numbers. Tune in and get ready to take your leadership to the next level!

Key Takeaways

• Leadership and its significance in business growth
• Challenges of multi-generational transitions in family businesses
• Importance of introspection and self-awareness for leaders
• Strategies for building a strong and accountable team
• Defining success beyond financial metrics
• Emotional dynamics and family relationships in business
• The role of professional development and continuous learning
• Focus on core competencies and the importance of saying "no" to distractions
• Planning for the future and creating a sustainable legacy
• The impact of leadership on employees and the community

In This Episode

• [00:00] Introduction to Agata
• [03:20] Challenges of multi-generational business
• [05:29] Building a strong team
• [06:13] Wealth management insights
• [08:00] Importance of specialization
• [09:15] The value of time
• [10:30] Exit strategies for business
• [14:43] The money test concept
• [17:27] Building a path of education and accountability
• [17:55] The necessity of the right team
• [20:06] Accountability as an empowering tool
• [21:01] The heartbreak of closing doors
• [22:28] Defining personal success
• [25:33] Success formula breakdown
• [27:56] Broader definitions of success

Notable Quotes

• [04:23] "When certain family members moved on, like my sister or my nephew, it felt a little bit painful because that was our trust factor." — Agata Olivieri

• [05:29] "Growing up, my parents were immigrants and they worked really hard to get what they got. They had nothing, like a second-hand couch was a big deal at the time." — Agata Olivieri

• [10:30] "If you don’t put an exit plan in place, what happens is that when your time is done, then your business’s time will be done because you didn’t prepare for that transition." — Madeleine MacRae

• [22:28] "I know I consider myself to be successful, and it probably took me a long time to realize that. I started to realize it when I was finally comfortable with accepting or taking a compliment." — Agata Olivieri

• [21:01] "For me, it's a little tiny bit heartbreaking when someone has worked so hard and then just closes the doors because just a little extra work, a little extra investment, could make such a difference." — Madeleine MacRae

• [23:45] "I am happy that I'm able to change lives within the business and outside the business with the work we do." — Agata Olivieri

Our Guest

Agata Olivieri is the co-owner of Maple Drapery & Carpet, a second-generation family...