We caught up with the brilliant and insightful Ashley Deland a few weeks ago and have shared our conversation below.

Hi Ashley , thanks for joining us today. Can you talk to us about a risk you’ve taken – walk us through the story?

One of the most defining and earliest risks was walking away from a very successful corporate career to become an entrepreneur.

At the time, I was working in a high-level marketing role, managing major portfolios and building campaigns and putting on events for million-dollar organizations. From the outside, it looked like the kind of career people spend decades trying to build. The stability was there, the income was there, the prestige was there.

But…

What wasn’t there was the alignment.

I had this growing sense that the work I was meant to do in the world was much bigger than the role I was holding. I was surrounded by brilliant leaders, visionaries, and thinkers through my work with global conferences and thought leaders, and it constantly reminded me that the most extraordinary impact comes from people who are willing to step out and build something of their own.

Still, leaving that environment meant walking away from security into complete uncertainty.

And coming from years in business school, this felt completely opposite of how I was “supposed” to move towards success.

I had no guarantees that the businesses I wanted to build would work. At the time, there was no roadmap, no safety net, and little income to self-invest.

The only thing I had was a conviction that betting on myself was the only path that felt intuitively and deeply right.

So I took the leap.

And truthfully, the early years were far from glamorous.

Like many founders, I experienced failures, pivots, reinventions, and moments where the outcome could have gone either way. I built companies from the ground up, sometimes with very little except belief, incredible work ethic, and the willingness to adapt and learn quickly.

But that decision; that single moment of choosing uncertainty over comfort shaped the entire trajectory of my life.
Since then, I’ve gone on to build and exit multiple businesses across industries, advise thousands of founders in more than 17+ countries, help generate tens of millions in revenue for women-led companies, and step into roles I never could have imagined at the beginning.

Every one of the milestones that I’ve achieved on this journey traces back to the same fundamental decision…

To always trust my own vision, passion and purpose enough to act on it.

That’s why “risk” for me, has never been about recklessness.

It’s always been about alignment.

Because when you know the direction you’re meant to go, staying where you are becomes the greater risk of all.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m a business advisor, multi-business founder, and investor who has spent the last decade helping founders build companies that are both profitable and deeply aligned with the impact they want to create.

Over the years, my work has grown into a global advisory practice within a wide range of industries, from hospitality and wellness to consulting, fashion, media, and education. What I’ve always been fascinated by is the intersection between the vision of a founder and the structure of a business. When those two things align properly, companies scale in powerful ways.

Today my work lives across several platforms all designed for female founders.

I’m the CEO of Maison De Land, a luxury marketing agency where we help visionary women architect brands that are positioned for long-term growth and influence. I also founded BMA Certifications, an ICF-accredited business coaching certification for women who want to step into leadership as advisors, consultants, and coaches themselves.

Alongside that, I host the She Wears the Pants podcast, where we explore the deeper leadership and identity conversations shaping modern entrepreneurship. Most recently, I stepped into the role of Executive Producer, Judge, and Master Mentor of a television series designed to bring mentorship, capital, and visibility directly to women-led businesses across the United States. I’m also the author and visionary behind Unreserved, a published anthology that brings together the stories of 24 women who are rewriting the narrative of success and leadership in their own lives and industries.

Across all of these platforms, my work centers on one core idea: helping women turn powerful ideas into sustainable and scalable companies.

What tends to set my work apart is that I approach business through both strategy and identity. Systems, marketing, and revenue models are of course, incredibly important but the founder behind the company matters just as much, if not more.

I spend a lot of time helping entrepreneurs expand their leadership capacity so their businesses can grow with them.

If there’s one thing I hope people understand about my work, it’s that I believe business can be one of the most powerful vehicles for impact. When founders are supported with the right strategy and the right environment to grow, their companies become forces that influence industries, communities, and future generations.

And personally, I want to see far more power, ownership, and capital in the hands of women

How’d you build such a strong reputation within your market?

If I had to point to one thing that has helped me build my reputation, it would be integrity.

When a founder invites you into their business, they are trusting you with something incredibly personal. A company often represents years of risk, sacrifice, and belief and I’ve always taken that responsibility very seriously.

My role isn’t just to celebrate what’s working or guide them towards next steps, it’s also to help founders see what they may be too close to recognize themselves. Sometimes that means offering encouragement and validation, and most other times it means having very honest conversations about the changes required for the business to grow.

I believe clients deserve both.

Another thing that has shaped my work is the level of care I bring into every engagement. I genuinely feel honored when someone opens the doors to their company and allows me to see the inner workings of what they’ve built. Because of that, I approach every client relationship with a mindset of going above and beyond.

Most of my business has always grown through referrals and that has always meant a lot to me because it reflects trust.
When a founder recommends you to someone else, they’re essentially putting their own reputation behind your work.

At the end of the day, I’ve never approached business purely from a financial perspective. My deeper motivation has always been impact.

When you focus on the service, the transformation, and the genuine privilege of helping someone build something meaningful, the reputation tends to take care of itself.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

One lesson I’ve had to unlearn over the years is the idea that life should feel any sort of “balanced”.

As someone who runs multiple businesses and is also a wife and mother to a three-year-old, life moves quickly. For a long time I believed that success meant being able to keep everything running at full capacity at the same time – career, family, health, friendships, and personal growth.

Eventually I realized that expectation simply isn’t realistic.

The biggest shift for me came when I started recognizing that time is my most valuable currency. It matters to me far more than money or any other external measures of success.

And, once you see time that way, you start making very different decisions about where your energy goes.

I’ve also realized that balance is rarely static.

I like to think of life as four main burners on a stove: family, career, health, and social life. In different seasons of life, certain burners naturally require more attention. When one or two burners are turned up to a higher level, the others need to be turned down for a while.

Trying to keep all four burners on full heat all the time eventually leads to burnout.

What I’ve learned instead is that life moves in seasons. There are moments when business requires deep focus, seasons where family needs more of your presence, and times when your health or personal life becomes the priority.

And seeing it all like that – gave me grace, permission and allowed me to see life through a whole new lens.

So now, for me, success has become less about achieving perfect balance and more about being intentional and aligned with where I place my energy, time and presence.

Contact Info:

• Website: https://www.ashleydeland.com
• Instagram: https://www.instagram.com/ashleydeland/
• Linkedin: https://www.linkedin.com/in/ashleydeland/
• Youtube: https://www.youtube.com/@ashleydeland