Business of Home Podcast: How Ashley Montgomery Survived a Stressful Split and Came Out Stronger

Host: Dennis Scully
Guest: Ashley Montgomery, Toronto-based interior designer
Date: August 18, 2025

Episode Overview

In this candid and insightful episode, Dennis Scully speaks with Ashley Montgomery about her journey navigating a personal and professional split from her husband and former business partner, emerging stronger and more confident in both life and business. Ashley shares lessons learned about business structure, personal growth, the challenges of motherhood as an entrepreneur, and how she’s reimagined her firm post-divorce. The conversation ranges from Canadian vs. American clients to her business strategies, and culminates with her new outlook on success, creativity, and community support in the design industry.

Key Discussion Points & Insights

1. Starting Out: Early Career, Family Influence, and Building a Firm

• Ashley was born into a family of home builders and was exposed to construction and design from a young age ([12:28]).
• Her path included early jobs at architectural firms, a chaotic small design firm (“a bouquet of red flags”—[14:33]), and a pivotal stint in a Toronto design retail store where she discovered her skill and market value as a designer ([15:52]).
• "I worked at American Eagle in high school. I can do this all over again." ([15:52])
• Ashley launched her own firm in 2014, starting small, taking on all kinds of projects, and learning business basics along the way.

2. Entrepreneurship & Motherhood: Juggling Growth and Family

• Discusses the realities of building a business while starting a family: “Look at me. No energy, no sleep, breastfeeding in my car… I can do it all.” ([04:37])
• Realization of needing separation between work and family life led to getting her first studio space: “I need a separation. I need to get dressed. I need to leave this house.” ([17:52])

3. The Business Partnership and the Split

• Ashley’s husband Eric joined the business, bringing crucial systems and operational structure ([03:15], [23:39]).
• Initial enthusiasm gave way to tension as their roles overlapped and communication broke down.
• Attempted to keep the business partnership after their marital split but found it unworkable: “Personal messes into business. Business messes into personal.” ([05:57])
• Learned the importance of understanding all aspects of her business, especially the financial side ([07:21]).
• Ashley cautions against 50/50 business splits: "I've learned never go into business with somebody 50/50… 51/49 every single day, never, ever, ever down 50/50." ([08:39])

4. Lessons in Business Operations and Growth

• After the separation, Ashley rebuilt her business structure, hiring an operations manager and bringing bookkeeping in-house ([28:09]).
• She shared the challenges of keeping the business afloat during a tumultuous period: "There was about a year where I was basically running a sinking ship, but trying to keep everything cool on the outside." ([28:11])
• Importance of setting clear boundaries in work/personal relationships, especially when family is involved: “…those conversations didn't end in this office. And that's the hardest part…” ([26:03])

5. Evolving the Business Model: Pricing, Markup, and Fees

• Describes the transition from not marking up product to instituting markups and hybrid billing models: “When I first started, I didn’t mark up anything… Everyone told me I was crazy.” ([30:27])
• Now employs a mixture of hourly and flat fees, and a transparent markup structure for furnishings and custom/vintage items ([29:15]-[30:27]).
• Recognizes that years of experience and a strong portfolio justify higher fees, even as her efficiency increases: “I don't spend nearly as many hours on projects anymore... but that's because we've built years and years of perfecting a craft.” ([34:57])

6. Navigating the Canadian & American Design Markets

• Ashley is often mistaken for being American, but is proud of her Canadian roots. She points out the practical differences between markets:
  • “Our American projects are easier to do than our Canadian projects… can’t get those tiles here...” ([41:51])
  • “Our appliances are double the price. Our plumbing fixtures are double the price. Our lighting fixtures are double the price.” ([41:54])
• Tariffs and limited Canadian manufacturing have led her to source globally, including from Europe and Turkey ([44:47]).
• On Canadian nationalism and sourcing: “Canadians, we're very proud of our country and what we do. And have we taken the easy route of going across the border for a lot of things in life? 100%… But now we're paying a lot more.” ([44:47])

7. Defining Success & Rebuilding After Crisis

• Ashley’s definition of success: balancing being a present mom and a thriving business owner ([21:54]).
• Emerging from hardship, she feels more confident and creative: “I feel like I've spent the last two years building this business internally back up again… My goal is to let it thrive now.” ([46:53])
• On rediscovering her love of design: “I’m falling back in love with it again and being creative again…” ([46:53])

8. Achieving New Goals: Publishing a Book

• Achieved a major goal: landing a deal with Rizzoli for a coffee table book about “the little moments in life” and “attainable, achievable luxury in all sorts of homes” ([36:57]).
• “As a Canadian designer to be picked up by an American publisher is… really amazing. I don’t like to, like, overly talk about how cool this is, but it’s really frigging cool.” ([39:18])

9. Community, Transparency & Growth After Crisis

• Emphasizes the importance of being open about challenges: “What I have learned by speaking openly is I'm not the only one going through this. There's lots and lots of entrepreneurs…” ([49:48])
• Rejects the association of separation/divorce with failure: “You have to change your mindset on it… It’s not failure. You were able to stand up for yourself and say, this isn’t working.” ([49:48])
• Therapy played a key role in reframing her challenges: “Yeah, therapy therapist was pretty good at that one.” ([51:20])
• Community support—especially from female entrepreneurs—has been vital (“…thank her so much for picking up the phone and calling me… she gave me a boost of confidence, and she's like, you can do this.” [52:21])

Notable Quotes & Memorable Moments

• On entrepreneurship and motherhood:
  "Look at me. No energy, no sleep, breastfeeding in my car… I can do it all." – Ashley ([04:37])

• On understanding your business:
  "You need to know the ins and outs of your business… I had no idea. I was just like, sure, no problem. I do this, you do that. Well, you need to know the ins and outs of your business." – Ashley ([05:57])

• On business partnerships:
  "I've learned never go into business with somebody 50/50… 51/49 every single day, never, ever, ever down 50/50." – Ashley ([08:39])

• On surviving tough times:
  "There was about a year where I was basically running a sinking ship, but trying to keep everything cool on the outside." – Ashley ([28:11])

• On pricing evolution:
  "When I first started, I didn’t mark up anything… Everyone told me I was crazy. I might have been…" – Ashley ([30:27])

• On her upcoming book:
  "I want a coffee table book. I want to walk through Home Goods or Homesense or Indigo… and I got it… It's about the little moments in life. Little moments in your home. We look at these big, beautiful homes… there's something so beautiful about the moments in these homes." – Ashley ([36:57])

• On redefining failure:
  "You have to change your mindset on it… It’s not failure. You were able to stand up for yourself and say, this isn’t working." – Ashley ([49:48])

• On therapy and personal growth:
  “You learn most from failure in life. You learn from mistakes that you make… I think I'm a better person. I'm a better mom, I'm a better friend… from this experience.” – Ashley ([51:20])

Timeline of Significant Segments

• [03:15] – Ashley recounts the beginnings of the business partnership with her (now ex-)husband
• [05:57] – The importance of knowing the business beyond just the creative
• [08:39] – Lessons about 50/50 business ownership
• [17:52] – The turning point: first studio and separating work/home
• [23:39] – How business operations changed after the split
• [30:27] – Discussion of pricing, markups, and how her approach evolved
• [34:57] – Recognizing the value of experience in pricing
• [36:57] – The journey to publishing her first book with Rizzoli
• [41:51] – Challenges of sourcing and tariffs in the Canadian market
• [49:48] – On openness, failure, and support from the community
• [51:20] – Therapy and learning from failure

Conclusion & Takeaways

Ashley Montgomery’s story is one of resilience, adaptability, and self-discovery. Her willingness to share the messy, human side of business and personal upheaval offers inspiration for designers and entrepreneurs, especially women balancing multiple demanding roles. She underscores the importance of understanding one’s own business, setting boundaries in partnerships, evolving pricing structures, and being unafraid to chart a new course—personally and professionally. As Ashley summarizes:

"You have to trust yourself and you gotta grow from that... You learn most from failure in life."
— Ashley Montgomery ([51:20])

This episode is a must-listen for anyone interested in the real-life challenges (and victories) behind the scenes of the design industry.