How Devon Montgomery Pasha Took the Leap into Full-Time Entrepreneurship

On this episode of Adventures in Business, Amani and Mandi interview Devon Montgomery Pasha, a dynamic Event Emcee, Facilitator, and "Experience Engineer" who brings over two decades of expertise to the events industry. Devon recently made the bold decision to go all-in on her own business, DMP Creative, at the start of 2025 – and she has a lot of wisdom to share about that choice, how she serves clients, and the questions she uses to spark transformation.

H2: Why She Went Full-Time

Although Devon technically launched DMP Creative back in July 2022, she didn’t take the full leap into solopreneurship until January 2025. Before that, she partnered with another organization where she served as U.S. Director. But over time, that role started to bump up against some of the boundaries she had intentionally set for herself.

She revisited an old executive performance exercise focused on boundary boxes and “anti-goals” – things you don’t want to tolerate in your life or work – and realized something had to change. Her energy was off. Her health was suffering. And the work no longer aligned.

So, she hit pause, got clear on what she truly wanted, and decided to go all in on herself. As she put it, “While I was figuring that out, it just meant I needed the flexibility to have control over my time and my life.”

H2: What DMP Creative Actually Does

Devon says she’s an event strategist and designer by trade, a trained MC, facilitator, and professional speaker. What she likes to do is get to know you and your problems – and then figure out how she can bring value.

Whether it’s helping a client rethink the flow of their event, designing a stage program, facilitating a course, or delivering a compelling keynote, Devon approaches every project with curiosity. She asks questions like “What’s the goal here?” “What’s getting in your way?” and “What do you actually want this experience to feel like?”

H2: The Surprise Benefits of Asking Better Questions

One of Devon’s favorite moments with clients is when they say something like, “Well, this is how we’ve always done it.”

Instead of accepting that as the end of the conversation, she gently moves the proverbial plate off the table and responds with: “Since the last time you changed it.”

It’s a simple but powerful reframing that opens the door to innovation – especially in organizations steeped in tradition. That one-liner, she says, has taken her 20 years to perfect, and it never fails to shift the conversation.

H2: Devon Montgomery Pasha’s Top Strategies for Building a Business from Scratch

H3: 1. Admit You Don’t Know Everything 

Devon’s first and perhaps most powerful strategy is admitting that she didn’t know what she didn’t know.

“I have never been in business before. I’ve worked for businesses where other people handled the business side – but I didn’t know how to do any of it.”

Rather than letting that uncertainty stop her, she asked questions – even when they felt basic or “stupid.” She Googled everything from how to track business expenses to what a sales funnel even was. The key was moving past the embarrassment and into action.

She also pointed out a hard truth: you’re going to make mistakes, and you’re probably going to waste some money along the way.

“You’re going to try something, spend money on it, and realize it’s not for you. Feel bad for five seconds, eat a brownie, drink some coffee, and move on.”

H3: 2. Build Your Support Squad: Coaches, Mentors, and Your “Board of Directors”

No one builds a business alone, and Devon is a strong advocate for surrounding yourself with support.

“Find your tribe. Some of them will be coaches – those are the best investments I’ve made. Hands down.”

She credits two coaches with significantly impacting her life and business within just two years. One of those coaches is Courtney Stanley, who helped Devon establish the structure she desperately needed in the early days of entrepreneurship.

Beyond formal coaching, Devon also leans on a personal “board of directors” – people she meets with monthly to get support in different areas: emotional, strategic, technical.

“You need people who will speak your name in rooms you’re not in. And you need people you can call when you’re stuck.”

H3: 3. Structure Your Time

One of Devon’s biggest early struggles was time management. With complete freedom over her schedule, she found herself frozen by indecision.

“I asked my coach, ‘What do I do every day?’ Like, what do I do on Monday versus Tuesday? I didn’t have any structure.”

Courtney helped her build a weekly rhythm: 

• Mondays for admin tasks – emails, invoices, to-do list cleanup

• Afternoons for meetings, since that’s when she’s less productive but more social

• Mornings for deep, focused work – her “golden hour”

• Fridays as a wellness and catch-up day, with space for therapy, yoga, or lunch with a friend

With that kind of structure, Devon can now differentiate between working in her business (getting things done) and working on her business (long-term strategy and growth).

H2: Connect with Devon Montgomery Pasha

🔗 Connect with Devon Montgomery Pasha on her website and on LinkedIn