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

02/04/25 • 30 min

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 business in Ontario specializing in high-quality window treatments and flooring solutions. With a deep-rooted passion for interior design and a commitment to excellence, Agata has been instrumental in upholding the company's legacy of transforming residential and commercial spaces since 1988. She emphasizes the importance of introspection, continuous learning, and focusing on core competencies to ensure long-term success. Under her leadership, Maple Drapery & Carpet continues to thrive, offering personalized design consultations and a curated selection of premium products to clients across Ontario.

Resources and Links

Agata Olivieri

Madeleine MacRae

Website

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?

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

Resources and Links

Agata Olivieri

Madeleine MacRae

Website

Previous Episode

Scaling the Gap EP 53 | Cracking the Code of Marketing Strategy: Insights from James on Reaching Your Ideal Customer

How often do businesses pour countless hours, resources, and energy into their marketing campaigns, only to feel like they’re speaking to an empty room? Picture this: you’re addressing a crowd of 10,000 people, but none of them are your ideal buyers. All that time and effort are wasted because your message isn’t reaching the right audience. It’s frustrating, right?

In this episode of Scaling the Gap, Madeleine MacRae sits down with marketing expert James Hipkin to discuss the game-changing power of marketing strategy. They explore why so many businesses misdiagnose their challenges as lead generation issues when, in reality, the problem lies in a lack of strategic focus. James offers valuable insights, emphasizing the importance of truly understanding customer needs and mapping out their buyer’s journey.

The episode makes one thing clear: focusing on customer outcomes—rather than just features or products—is the key to standing out in today’s noisy market. Are you ready to stop marketing to an empty room and start connecting with the right audience? Tune in and learn how a well-defined strategy can transform your business.

Take action today: Listen to the full episode and start crafting a marketing strategy that reaches the right people and drives real results. Your ideal customers are waiting!

Key Takeaways

Importance of marketing strategy over mere mechanics
Understanding customer needs and the buyer's journey
Misdiagnosis of marketing challenges as lead generation issues
Creation of customer avatars and journey maps using AI
Focus on outcomes rather than features in marketing
Selling transformations instead of just products
Building trust through genuine relationships in business
The overwhelming volume of marketing messages consumers face
Humanizing marketing efforts to connect with customers
Leveraging technology for effective marketing insights and strategies

In This Episode:

[00:01:03] Introduction to James Hipkin
[00:04:55] The importance of the buyer's journey
[00:05:18] Branding vs. marketing strategy
[00:08:07] The gray noise of marketing
[00:10:13] The necessity of a marketing strategy
[00:11:08] AI in marketing strategy development
[00:14:57] Humanizing the marketing process
[00:17:54] The importance of contextualizing marketing
[00:18:14] The story of FedEx
[00:19:58] Understanding customer needs
[00:21:24] Selling transformation, not products
[00:24:12] James’ definition of success
[00:27:17] Conclusion and resources

Notable Quotes

[00:07:20] "We spend so much time, effort, and energy just marketing to an empty room. Even if the room is crowded with 10,000 people, if not one of them is your ideal buyer, it's essentially empty for you." — Madeleine MacRae
[00:10:55] "You don't have to compete with the masses and the mass marketers. In your local market, you just need to be 10% better than everyone else, and strategy will give you that 10% and more." — James Hipkin
[00:14:33] "So often, marketing feels really sterile. When I put on my marketing hat, my language becomes so stiff, and I'm like, who is this woman? This is definitely not the Madeleine that shows up on stage or in a conversation." — Madeleine MacRae
[00:18:58] "They went after those executive assistants who knew they were going to get yelled at by their boss if the package didn’t get from Chicago to New York overnight." — James Hipkin
[00:21:06] "You’re really buying access to the destination. You just want to be there, right?" — Madeleine MacRae
[00:24:18] "Success for me is not a tangible thing. I feel I’ve achieved success when I have the respect of my peers." — James Hipkin

Our Guest

James Hipkin is the founder of Inn8ly, a company dedicated to helping six-figure business owners grow to seven figures by offering professionally designed, secure, and customer-centric websites. With over a decade of experience in web design, James uses his expertise to simplify complex website management for small businesses. Inn8ly’s services are backed by Red8 Interactive’s 10+ years of corporate experience, ensuring efficient website builds, secure hosting, and customer-focused strategies. James is passionate about demystifying digital marketing and helping businesses thrive online.

Resources and Links

James Hipkin

Madeleine MacRae

Next Episode

Scaling the Gap Ep 55 | The Contractor’s Edge: Rich Harshaw on Resilience, Perspective, and Redefining Success

What if the key to standing out in a crowded market wasn’t just about what you sell, but the stories you tell?

In this episode of Scaling the Gap, host Madeleine MacRae sits down with Rich Harshaw, owner of Level 10 Contractor, to explore leadership, marketing strategies for contractors, and the transformative power of storytelling. Rich delves into the evolution of his company, highlighting the importance of standing out in a competitive market. Rich also shares his personal journey, including lessons learned from business challenges and the invaluable role of mentorship, offering actionable insights for contractors looking to elevate their marketing and build lasting client relationships.

Rich introduces his philosophy, "It's always something; it's never nothing," underscoring the inevitability of life's challenges and the importance of resilience in overcoming them. The conversation explores the distinction between pain and suffering, with Rich advocating for gratitude and perspective as tools to navigate life's ups and downs.

This episode leaves you with a reminder to appreciate what you have and embrace challenges as opportunities for growth. Let’s dive in!

Key Takeaways

The role of introspection and leadership growth in driving business success.
Tailored strategies for contractors in the home services industry to stand out.
How authentic, relatable stories can transform marketing efforts.
The importance of differentiation in a crowded market.
Insights into navigating obstacles faced by smaller contractors.
How personal experiences shape professional journeys.
The value of mentorship and building industry relationships.
Evaluating marketing materials for uniqueness and authenticity.
Using relatable messaging to establish credibility with clients.
Viewing challenges as opportunities for growth and learning.
Understanding success as a subjective, perspective-driven concept.
The importance of bouncing back from setbacks.
Recognizing that while pain is inevitable, suffering is optional.
Cultivating a mindset of appreciation for current circumstances.

In This Episode:

[00:00:00] Rich Harshaw's background
[00:01:45] The meaning of Level 10
[00:04:45] The Happy Money Promise
[00:07:24] The importance of identity in marketing
[00:08:30] Storytelling vs. platitudes
[00:09:22] Using quality materials in marketing
[00:11:51] The 'So What?' game
[00:15:04] Connecting with customers through relatable stories
[00:17:56] Rich's journey into marketing
[00:25:01] Lessons from business failure
[00:29:55] Success and personal definition
[00:30:07] Facing challenges and appreciating what you have
[00:37:03] Closing thoughts

Notable Quotes

[00:05:38] "We had a customer install an HVAC system for $17,000, and the client felt overcharged. So, we refunded all their money, and they kept the system. That’s one way to fix a problem." — Rich Harshaw
[00:12:23] "When someone acts like the table stakes of business are their calling card, it gets me going. We show up on time? Oh, goody. You have to be competent at an extreme minimum to earn and maintain your business." — Madeleine MacRae
[00:14:42] "If we’re even one single minute late, you don’t pay. There’s no fine print, no hoops to jump through. It’s just free." — Rich Harshaw
[00:22:24] "Having been a cash millionaire, I was in debt $3 million. That was my business exploding like the Hindenburg." — Rich Harshaw
[00:25:28] "The fear of failure completely goes away once you've failed. It allows you to take more risk, controlled risk, of course." — Rich Harshaw
[00:27:06] "I was in a pretty low moment, and I saw a sticker that said, 'But did you die?' I burst into laughter because it reminded me that even if you stumble, you’re still alive." — Madeleine MacRae

Our Guest

Rich Harshaw is a seasoned entrepreneur, business strategist, and the founder of Level 10 Contractor, a company dedicated to helping contracting businesses achieve exponential growth and operational excellence. With over two decades of experience in the construction industry, Rich has established himself as a leading authority in business development, marketing, and strategic planning for contractors.

Rich's journey began with his own contracting business, where he honed his skills and developed a deep understanding of the challenges faced by contractors. Leveraging this hands-on experience, he transitioned into consulting, where he has helped countless contracting businesses streamline their operations, increase profitability, and scale effectively.

At Leve...