Bold Enough

In this episode of Scaling the Gap, host Madeleine MacRae has an honest and inspiring conversation with Andrew Killian, founder and CEO of HomeStead HotLeads, about what it really takes to walk away from a successful career in software engineering and build something of your own.

Andrew opens up about the motivations behind his leap into entrepreneurship, the obstacles he’s faced, and the deeply personal rewards that come from pursuing freedom, fulfillment, and impact. He highlights the role of gratitude in business, especially in the remodeling space, and how being intentional about connecting with female buyers has helped him create a more human, results-driven customer experience.

This episode offers real-world wisdom on starting over, staying agile, and scaling strategically—with heart.

Key Takeaways

• Adapting to changes in a fast-paced environment and learning to anticipate market shifts before they happen.
• Building a vision for your business that balances where you are now with where you want to go.
• Bridging the gap between ideas and action through intentional, consistent execution.
• Turning launch delays or market entry setbacks into opportunities for growth and strategic reflection.
• Using gratitude as a foundation for better client relationships and stronger business culture.
• Understanding emotional buying behavior to create more impactful customer experiences.
• Pursuing freedom and autonomy as core motivators for long-term entrepreneurial success.

In This Episode:

• 00:00 - Introduction to Andrew Killian
• 01:55 - Andrew's Entrepreneurial Journey
• 03:09 - The Power of Gratitude in Business
• 04:47 - Making the Leap: Motivations and Challenges
• 09:05 - The Importance of Environment and Free Will
• 16:54 - Niches Make Riches: Tailoring to Female Buyers
• 20:03 - Defining Success and Personal Freedom
• 25:10 - Conclusion and Final Thoughts

Notable Quotes

• [00:03:14] " Thank you is so much more powerful than I'm sorry. It's really leaning into that expression of gratitude, helping to align things to appreciate rather than to point for the failing or to point towards something different." — Madeleine MacRae
• [00:09:45] “ I'm a big believer in always questioning why you believe what you believe.” — Andrew Killian
• [00:19:25] “ if you do what you've always done, you're gonna end up getting less than what you've always gotten.” — Madeleine MacRae
• [00:22:21] " Being able to just control your time is  the most accurate predictor of happiness." — Andrew Killian

Our Guest

Andrew Killian is the founder and CEO of HomeStead HotLeads, a company dedicated to helping home improvement businesses generate high-quality leads through strategic digital marketing. With a background in software engineering, Andrew made the leap into entrepreneurship to pursue greater freedom and impact. He's passionate about gratitude-driven leadership, customer experience, and empowering service-based businesses to thrive through smarter marketing and authentic connection.

Resources and Links

Andrew Killian

• LinkedIn

Madeleine MacRae

• Website
• LinkedIn
• Instagram

In this episode of Scaling the Gap, Madeleine MacRae sits down with Dena Jalbert, CEO of Align Business Advisory Services, for a deep dive into the world of mergers and acquisitions (M&A) for founders and family-owned businesses. Dena unpacks the emotional and strategic challenges of selling a business, stressing the importance of planning ahead, staying true to core values, and finding the right buyer.

The conversation goes beyond numbers, touching on the evolving M&A landscape and the power of intentionality in business transitions. Madeleine and Dena explore the role of integrity, trust, and the joy of helping clients succeed. Madeleine shares her passion for negotiation and the balancing act of staying authentic, while Dena emphasizes the value of "entrepreneurial street smarts."

Together, they reflect on lessons learned—shifting from corporate to entrepreneurial hiring, redefining success beyond financial gain, and the importance of service, diversity, and innovation in business. The episode wraps up with a powerful takeaway: success isn’t one-size-fits-all—it's about defining it on your own terms.

Key Takeaways

• Mergers and acquisitions (M&A) in the context of founder and family-owned businesses.
• The unique characteristics and significance of the middle market in business transactions.
• The emotional challenges faced by business owners when selling their companies.
• The generational shift in business ownership and its implications for exit strategies.
• The importance of planning for value extraction well in advance of a sale.
• Aligning personal values with potential buyers during the M&A process.
• The role of specialized guidance in navigating business transitions.
• The evolution of M&A practices and the focus on smaller deals post-financial crisis.
• Viewing M&A as an opportunity for growth rather than an endpoint.
• The necessity of strategic planning and exploring diverse exit options for business owners.

In This Episode

• [00:00:58]   Introduction to Dena  
• [00:04:52]   Shifts in M&A focus  
• [00:06:52]   Understanding transactions  
• [00:09:35]   Impact on families  
• [00:10:18]   Planning for retirement  
• [00:12:08]   Value extraction importance  
• [00:13:05]   Planning for a successful exit   
• [00:15:06]   Concerns about ownership change  
• [00:16:04]   Finding the right partner     
• [00:20:00]   Emotional turmoil in M&A   
• [00:21:30] M&A misconceptions  
• [00:22:43] Evolution of M&A practices  
• [00:22:56]  Access to resources   
• [00:25:51] The Cheesecake Factory metaphor   
• [00:27:20] Challenges of entrepreneurship  
• [00:35:39] Defining success
• [00:44:45] Final thoughts and call to action

Notable Quotes

• (00:12:08) "I saw, I observed it happen again and again and again, where I said, 'Oh, whoa, whoa, whoa, like that can't be the case, right? We have to get the good word out there that it does take a little bit more planning.'" — Madeleine
• (00:17:08) "You didn't have a partner, and partnership is an active verb in this case, not just an individual. You have to take active engagement in that, and so it's strategic, it's not by accident." — Dena
• (00:17:54) "I want someone who knows me deeply to help me when I'm ready. I'm not going to start drilling my own teeth, so why would I not entrust my life's work to a specialist?" — Dena
• (00:24:22) "Nobody starts a business hoping that one day they will walk away without realizing its value. If you don't plan to maximize the value of that asset, it just dies on the shelf." — Dena

Our Guest

​Dena Jalbert is the founder and CEO of Align Business Advisory Services. With nearly 20 years in "Big 4" public accounting and executive roles at Fortune 500 companies, she has facilitated over $3 billion in transactions involving firms like Visa and Google.

Resources and Links

Dena Jalbert

• Website
• LinkedIn

Madeleine MacRae

• Website
• LinkedIn
• Instagram

What if the secret to building a thriving business wasn’t about cutting-edge strategies or flashy marketing—but something much simpler, yet profoundly powerful? What if the key to customer loyalty, team satisfaction, and even personal fulfillment could be summed up in one word: love?

In this episode of Scaling the Gap, host Madeleine MacRae sits down with Janie Sandberg, co-owner of Floor Coverings International in Henderson, Nevada. Janie shares her inspiring journey of building a business with her husband, Jeremy, while balancing the chaos of family life with three kids in different schools. Together, they’ve created a flooring business that’s not just about floors—it’s about creating meaningful connections and delivering a "white glove experience" to their customers.

Key Takeaways

• The importance of customer service and creating positive client experiences.
• Balancing family life with the demands of running a business.
• The significance of building strong relationships with customers.
• Strategies for navigating challenges in the construction industry.
• The emotional aspects of entrepreneurship and managing stress.
• Redefining success beyond financial metrics to include personal fulfillment.
• The impact of a caring business culture on customer loyalty and community.

In This Episode

• (00:00:00) Introduction to Janie Sandberg
• (00:06:59) Creating a customer-centric experience
• (00:08:41) Unexpected joys of business
• (00:10:53) Reciprocal customer relationships
• (00:12:53) Challenges in the flooring industry
• (00:14:44) Continuous improvement mindset
• (00:16:46) Defining success
• (00:19:19) Broader definition of success
• (00:22:04) Navigating business challenges
• (00:25:15) Connecting with Janie

Notable Quotes

• (00:07:52) "The first thing that we're always thinking about is how can we show love to our customers?" — Janie Sandberg
• (00:09:03) "I have found a lot of friends which I think is unusual; my husband sometimes looks at me and goes like I don't think this is normal that we have all these customers that send us Christmas cards." — Janie Sandberg
• (00:17:13) "If I'm defining my success by showing love to my customers, are we delivering an outstanding experience, or are we adding value to their lives, then yes, 100% we're doing that." — Janie Sandberg
• (00:18:43) "Success is defined by being able to boldly live your values, by adding value to people's lives, by making the time for the things that matter in life, by navigating your life with an element of grace, and by having space for more achievements still to come." — Madeleine MacRae
• (00:23:59) "At the end of the day, I would still have my marriage, I'd still have my family, I would still have the relationships I built. Those things don't change; the rest of it's just money and stuff." — Janie Sandberg

Our Guest

Janie Sandberg is a small business owner and co-founder of a flooring company in Henderson, Nevada. With a deep commitment to customer service, she prioritizes creating a supportive, family-like experience for clients. Janie believes in leading with love, building lasting relationships, and continuously improving her business. She balances entrepreneurship with family life, embracing both challenges and rewards.

Janie Sandberg

• Website
• LinkedIn
• Instagram
• For Las Vegas Locals: Reach out to Janie and Jeremy for your flooring needs!

Madeleine MacRae

• Website
• LinkedIn
• Instagram

Being a CEO means navigating constant pressure, especially when scaling your business. Now, imagine this: you're sitting on the edge with everything on the line. The stakes are high, and failure seems inevitable. So, what do you do? 

In this episode of Scaling the Gap, host Madeleine MacRae sits down with Matt Millsap, CEO of Build Co. 7, to explore how he not only weathered the tough times but built a thriving business rooted in leadership, integrity, and growth.

Matt’s journey wasn’t without its hurdles. After discovering he was $250,000 in debt, he turned to seasoned mentors and made bold moves that transformed his company—and his mindset. He shares the invaluable lessons he learned about leadership, company culture, and financial management, plus his “rule of two” approach that’s empowering his team to solve problems with solutions.

Join us as Matt reveals how turning a crisis into an opportunity became the foundation for his company’s success. Let’s dive in!

Key Takeaways

• Building a strong team and company culture is paramount to success
• Financial struggles can teach invaluable lessons in accountability and integrity
• Delegating effectively and empowering your team leads to better results
• Strong client relationships are the backbone of sustainable business growth
• Continuous learning and personal growth are integral to leadership success

In This Episode

• [00:00:00] Introduction to Matt Millsap
• [00:01:06] Importance of building a team
• [00:02:04] Refining leadership skills
• [00:03:00] Letting go of weaknesses
• [00:05:02] Inspiration behind starting the business
• [00:06:27] Navigating the 2008 recession
• [00:07:23] Focus on historic renovations
• [00:09:08] Choosing the right clients
• [00:11:01] Defining ideal clients
• [00:12:24] Learning from difficult clients
• [00:13:41] Monitoring financial metrics
• [00:14:29] Facing financial challenges
• [00:16:01] Overcoming financial challenges
• [00:16:46] Learning and growth
• [00:17:17] Honoring obligations
• [00:19:33] Building trust with bankers
• [00:21:57] Unexpected team loyalty
• [00:23:37] Creating Construction Coach
• [00:26:37] The rule of two
• [00:29:22] Success reflection

Notable Quotes

• [00:02:04] "Once I realized that the focus needed to be on a healthy company culture, things really started to blossom." — Matt Millsap
• [00:06:27] "I remember I wrote it out with him as long as I could and I looked at him one day finally and I just said, 'Boss, you know the captains got to go down with the ship, but the first mate doesn't.'" — Matt Millsap
• [00:16:01] "I owed a lot of people a lot of money, and I never dodged a call. I would just pick up the phone and say, 'I can't pay you today, but I'm going to pay you.' It was one of the toughest times of my life." — Matt Millsap
• [00:17:37] "I had a situation where I couldn’t pay my taxes. We lost a key client, and I couldn’t afford my bills. But I honored my obligations, and I paid it anyway. The owner of that company wrote me the most heartwarming email when I paid the last payment." — Madeleine MacRae
• [00:21:57] "An unexpected delight has been the team that I’ve built over the past years. They support me because they see the value in what I do for the company. That’s probably one of the surprises I would say." — Matt Millsap

Our Guest

Matt Millsap is the founder of Build Co. 7, a Nashville-based contracting company with over 16 years of experience in design, construction, and investment. The company specializes in remodeling and renovating older and historic homes, as well as undertaking small-to-medium commercial and retail projects. Their services include kitchen and bathroom remodeling, detached garages, additions, and new constructions. Build Co. 7 has been recognized with multiple awards for client satisfaction and is known for its meticulous pre-construction and construction processes.

Matt Millsap

• Website
• LinkedIn

Madeleine MacRae

• Website
• LinkedIn
• Instagram

In this episode of Scaling the Gap, host Madeleine MacRae welcomes Gabe Lullo, CEO of Alleyoop, a leading sales development agency. Gabe shares insights into his company's approach to sales, which focuses on prospecting and appointment setting for various businesses. 

The conversation explores the importance of mastering language and communication in sales, the integration of AI and technology, and the value of maintaining human interaction in sales processes. Gabe also discusses his personal journey, including early influences and the concept of 'leadership duplication'—the practice of magnifying specific talents within a team. 

This episode is filled with practical advice and inspirational stories for leaders and entrepreneurs aiming to scale their organizations and build lasting legacies.

Key Takeaways

• Recognizing the magic of words and their potential to earn financial success
• Drawing inspiration and elaborating a packaging sales strategy akin to a sports team’s dynamics through using competitive, gamified environments to cultivate high-performing sales teams
• The role of AI and technology in sales and how sales professionals should embrace it as a tool to enhance their capabilities
• Why building a sales team should naturally follow business growth rather than precede it
• The concept of leadership duplication, focusing on elevating different slices of excellence in team members rather than creating carbon copies of oneself
• The importance of using language as a tool to create reality, whether it’s shaping one’s identity or building a thriving business

In This Episode:

• 00:00 - Introduction to Gabe Lullo
• 01:35 - The Concept of Sales Development and Its Importance
• 04:04 - The Art of Prospecting and Overcoming Rejection
• 09:27 - Gabe's Journey: From Fundraising to Sales Leadership
• 12:46 - Leadership Duplication and Personality Types
• 17:53 - Challenges and Technological Advancements in Sales
• 22:39 - Defining Success and Personal Reflections
• 26:28 - Closing Thoughts and How to Connect

Notable Quotes

• [00:08:01] " You have to really be in the habit of collecting the no's because the no is the doorway to the yes." — Madeleine MacRae

• [00:11:08] " Communication is a way of generating wealth. And that is just such a beautiful way to look at it." — Madeleine MacRae
• [00:12:37] “If I can start teaching people what I was doing, then [I] could build an army.” — Gabe Lullo

• [00:14:41] “Your job is really to be the octopus or the chameleon. It's to change colors, not as a manipulation or as a way of hiding anything, but as a way to relate to the person you're talking to.” — Gabe Lullo

• [00:24:16] " Success is just a decision that I've chosen. I just decided that I was going to be, and as soon as I made that decision to do it, everything else started just happening." — Gabe Lullo

• [00:27:14] “Language is a really powerful vehicle that you can master to speak into reality things that don't exist yet, whether it's who you decide you're becoming or what you decide you're building, or even the team that you're curating, creating.” — Madeleine MacRae

Our Guest

Gabe Lullo is the CEO of Alleyoop, a premier firm dedicated to transforming the Sales Development Representative (SDR) function for top-tier clients. As Chief Business Officer, Gabe leverages AI and cutting-edge technologies to revolutionize sales processes, enhancing efficiency and delivering outsourced SDR solutions that have fueled the pipelines of industry leaders like Adobe and ZoomInfo. His visionary leadership and deep expertise in sales strategy underscore the critical role of SDRs and the transformative power of AI in modern sales operations.

Resources and Links

Gabe Lullo

• LinkedIn
• Alleyoop

Madeleine MacRae

• Website
• LinkedIn
• Instagram

In this episode of Scaling the Gap, host Madeleine MacRae sits down with Mary Kennedy Thompson, CEO of Business Network International (BNI) and a former Marine Corps officer, to explore the values-driven leadership that fuels business success.

Mary shares her journey through personal and professional challenges, from navigating the loss of a mentor to leading her organization through the uncertainty of the COVID-19 pandemic. She discusses the crucial difference between being brave—seizing opportunities in tough times—and being bold—leading others through transformational change.

With deep insights from her time in the Marine Corps, Mary reveals how discipline, integrity, and resilience have shaped her leadership philosophy. She also highlights the power of networking, the role of generosity in business, and how to create a legacy that aligns with core values.

Whether you're a leader navigating uncertainty or an entrepreneur striving for impact, this episode is packed with wisdom, inspiration, and actionable strategies to help you lead with confidence, build meaningful connections, and drive success.

Key Takeaways

• How grounding decisions in core values leads to stronger organizations
• Handling challenges and change as a team leader during personal losses or global events like the COVID-19 pandemic
• Why networking is seen as a vital business skill that fosters growth.
• The importance of being mindful about the legacy you create and ensuring it aligns with your values
• How to balance established traditions with innovative practices for organizational growth and resilience
• How the discipline and values from military influence emphasize integrity, responsibility, and centering oneself under stress
• The principle of “Givers Gain,” or the belief that starting with generosity often leads to receiving benefits in return
• The role of forming human connections in achieving business success
• The importance of having fun and finding joy in the process, which enhances resilience and team morale

In This Episode:

• 00:00 - Introduction to Mary Kennedy Thompson, CEO of BNI
• 01:35 - Understanding BNI: The World's Largest Business Referral Network
• 03:40 - The Importance of Values in Leadership
• 10:16 - Lessons from the Marine Corps
• 14:48 - Overcoming Personal and Professional Challenges
• 16:57 - Navigating the Challenges of COVID-19
• 18:09 - The Importance of Bold Leadership
• 18:22 - Thriving Through Adversity
• 20:45 - The Role of Networking in Business
• 21:41 - Leadership Responsibilities and Vision
• 23:53 - The Relationship Economy
• 29:09 - Defining Success and Significance
• 32:35 - Final Thoughts and Reflections

Notable Quotes

• [00:04:27] " What makes an organization really strong is diversity: diversity of thought, diversity of experience, diversity across the board.  And we bring this diverse group together that all say, yes, we agree to this set of values, how we're going to do things makes a difference." — Madeleine MacRae
• [00:06:48] " Your personality is what you show everybody, but your character is what you do when no one's watching." — Mary Kennedy Thompson
• [00:08:02] " You make a living by what you get, but you make a life by what you give." — Mary Kennedy Thompson
• [00:09:49] " I don't judge leaders by how the organization works when they're standing right there. I judge them by how it works when they're not there." — Mary Kennedy Thompson
• [00:20:23] " Confidence is a byproduct that most people wait for, but you don't get it without courage." — Madeleine MacRae
• [00:21:52] “ The root of the word inspire means to breathe life into,  but we are here to bring life into one another as a leader.  I'm here to breathe life into the team and serve them, help them be the best version of themselves.” — Mary Kennedy Thompson
• [00:28:28] “ You have to say no to the good so you can embrace the great. And when you're already doing the great things, you have to start to say no to the great so you can say yes to the excellent.” — Madeleine MacRae

Our Guest

Mary Kennedy Thompson is a highly accomplished and inspirational leader, currently serving as the CEO of BNI (Business Network International), the world's largest business referral networking organization. With an impressive track record in leadership roles, Mary has a unique background that spans military service as a Marine Corps officer, significant contributions in the 30 years in franchising, supporting business owners and entrepreneurs of all sizes, significant experience in global expansion & development, integrations, and a deep commitment to compassionate, effective & values-driven leadership. 

Resources and Links

Mary Kennedy Thompson

• LinkedIn

Madeleine MacRae

• Website
• LinkedIn
• Instagram

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 Level 10 Contractor, Rich and his team provide a comprehensive suite of services, including business coaching, marketing strategies, and operational consulting, all tailored to the unique needs of contracting businesses. Rich is also a sought-after speaker and author, sharing his insights and expertise through various platforms to empower contractors to reach their full potential.

Scaling the Gap

• Podcast

Rich Harshaw

• Website
• LinkedIn
• Podcast

Madeleine MacRae

• Website
• LinkedIn
• Instagram

Mentioned 

• Episode on The Level 10 Contractor Daily Podcast: 1902: Getting Serious About Scaling Your Business (Madeleine MacRae)

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.

Agata Olivieri

• Website
• LinkedIn

Madeleine MacRae

• Website
• LinkedIn
• Instagram

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

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.

James Hipkin

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Madeleine MacRae

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Running a family-owned business is no small feat, right? How do you keep the balance between family dynamics and professional growth? What happens when an economic downturn hits—do you fight or fold? In a competitive market, is it better to sacrifice quality for price, or is holding onto your values the real secret to success? And when it comes to your employees, how do you create a workplace where they feel valued, heard, and invested in?

In this episode of Scaling the Gap, host Madeleine MacRae interviews Vanessa Yates, co-owner and designer of Draped in Style, a family business specializing in window treatments and fabric products. Vanessa shares her entrepreneurial journey, starting the business with her mother, and the challenges they faced, including the 2008 housing market crash. They discuss the importance of maintaining quality over competing on price and fostering a supportive company culture. Vanessa emphasizes creating an equitable workplace and the significance of valuing employees, which has led to a loyal and dedicated team. Want to learn how to lead your family business with heart and strategy? Don’t miss this conversation!

Key Takeaways

• Vanessa Yates' entrepreneurial journey and the founding of Draped in Style
• The dynamics and challenges of running a family-owned business
• The impact of economic downturns on small businesses, particularly during the 2008 housing market crash
• The importance of maintaining quality and value over competing on price in a competitive market
• The significance of cultivating a strong company culture and employee engagement
• The difference between equality and equity in the workplace and its implications for team dynamics
• The disconnect between corporate environments and small businesses regarding customer connection and financial understanding
• Strategies for creating a supportive work environment that values employee input and well-being
• The broader definition of success beyond financial metrics, focusing on positive impacts on employees and communities
• The role of identity in defining personal and professional success

In This Episode

• [00:00:57] Vanessa's background
• [00:10:14] Building company culture and employee engagement
• [00:15:00] Creating a supportive work environment
• [00:17:51] Equality vs. equity in the workplace
• [00:19:38] The benefits of small business flexibility
• [00:21:07] Adapting big business strategies to small business
• [00:24:08] Measuring success beyond financials
• [00:26:01] Identity and financial success
• [00:27:57] Vanessa's definition of success

Notable Quotes

• [00:05:04] "To really take a step back sometimes and look at where we've come now, you know, to have two full-time installers, to have ten people in the office, the growth of that is what's really driving me these days." — Vanessa Yates

• [00:11:13] "One of the biggest compliments I feel like I've gotten as a boss is that, 'Vanessa, I feel very heard with you. I feel very seen with you. I feel like I'm valued and my opinion matters.'" — Vanessa Yates

• [00:23:58] "The fact that 12 people can make a good living, enjoy what they do, and go home to be better moms, better wives, better husbands, dads, friends, brothers—all the things—that is success because then you've affected not 12 lives, you've affected hundreds." — Vanessa Yates

• [00:24:08] "I love it so much. I've been asking people now for a whole year, 'Do you consider yourself to be successful?' and time after time, there's almost no mention of money." — Madeline McRae

• [00:27:57] "I feel in everything that we've built as a team and who our team is, I just... put my team against anybody in town and we're going to win every time." — Vanessa Yates

Our Guest

Vanessa Yates is the Lead Designer at Draped in Style, where she specializes in helping homeowners create personalized, stylish window treatments that enhance the look and feel of any room. Known for her enthusiasm and expert design knowledge, Vanessa makes every consultation both fun and informative. With years of experience, she has helped hundreds of clients achieve the perfect window treatments, always prioritizing quality and customer satisfaction.

Vanessa Yates

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Madeleine MacRae

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