We recently connected with Ryan Cobbins and have shared our conversation below.

Ryan, thanks for joining us, excited to have you contributing your stories and insights. We’d love to have you retell us the story behind how you came up with the idea for your business, I think our audience would really enjoy hearing the backstory.

Momentum Advisory really came from the accumulation of years of entrepreneurial experience, leadership, operational growth, community building, and helping people solve problems in real time. It wasn’t one single moment, it was the realization that throughout my career, people consistently came to me for guidance, clarity, strategy, and support around building something meaningful.

One of the biggest chapters that shaped this journey was founding Coffee at The Point in Denver’s historic Five Points neighborhood. At the time, I didn’t come from a traditional coffee background, but I had a vision for creating something much larger than a coffee shop. We built a 3,000-square-foot community-centered coffee and wine lounge that eventually became one of the most recognized coffee shops in the state. Over 12 years, we built a team, developed systems, created culture, won 13 local and national awards, and built a business that became a gathering place for entrepreneurs, leaders, artists, students, and the broader community.

What fascinated me most wasn’t just coffee, it was leadership, systems, growth, operations, culture, and helping people move ideas into reality.

That experience eventually led into broader leadership opportunities, including directing more than $17 million in grants and loans for small businesses across Colorado, helping entrepreneurs navigate uncertainty and growth, and later working nationally with No Labels, where I helped cultivate leadership, coalition-building, fundraising strategy, and organizational growth across all 435 congressional districts.

Over time, I began to notice a consistent pattern:
many incredibly capable people were stuck.

Not because they lacked intelligence or work ethic, but because they lacked:
• clarity
• structure
• strategic guidance
• accountability
• or someone who could help them organize complexity into momentum.

Sometimes people needed inspiration and encouragement to keep moving. Other times they needed someone to step into the weeds with them, to help solve operational problems, think strategically, structure ideas, identify blind spots, or simplify what felt overwhelming.

That’s where the evolution into Momentum Advisory really happened.

I realized the work I naturally did sat somewhere between coaching and consulting. The coaching side helped people reconnect to confidence, vision, and momentum. The consulting side helped take fragmented pieces of ideas, businesses, leadership challenges, and opportunities and turn them into more organized systems, strategies, and actionable next steps.

What excited me most was that the framework worked across industries because the underlying human challenges were often the same:
uncertainty, lack of clarity, inconsistent systems, fear of taking action, or difficulty translating experience into meaningful growth.

Momentum Advisory became the formalization of years of helping people think more clearly, move more strategically, and build with greater confidence and intention.
What makes it different is that it’s grounded in real-world execution, not theory. I’ve built businesses, led teams, deployed capital, navigated uncertainty, cultivated partnerships, and operated inside both entrepreneurial and national leadership environments. The work is deeply human, strategic, and implementation-focused.

At its core, Momentum Advisory exists to help capable people stop feeling stuck and start building meaningful momentum around what’s next.

Ryan, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

For most of my career, I’ve found myself drawn toward building things, solving problems, helping people navigate uncertainty, and creating environments where growth and momentum could happen. Long before Momentum Advisory formally existed, I was already doing the work, helping entrepreneurs, leaders, and organizations think more clearly, organize complexity, and move ideas into action.

One of the defining experiences in my journey was founding Coffee at The Point in Denver’s historic Five Points neighborhood. What started as an idea eventually became a 3,000-square-foot coffee and wine lounge that operated for more than a decade and became one of the most recognized coffee shops in the state. We built culture, systems, operations, partnerships, and a community-centered business that ultimately received 13 local and national awards.

What fascinated me most wasn’t simply the coffee business itself, it was the leadership, operational strategy, systems development, relationship-building, and the process of taking an idea and turning it into something real and sustainable.

That entrepreneurial journey opened doors into broader leadership work. I later directed more than $17 million in grants and low-interest loans supporting small businesses across Colorado, helping entrepreneurs navigate uncertainty, growth, operational challenges, and recovery. I also worked nationally with No Labels, where I helped cultivate leadership, fundraising strategy, coalition-building, and organizational growth efforts spanning all 435 congressional districts.

Throughout all of those experiences, one thing became increasingly clear to me:
Many incredibly capable people feel stuck.

Not because they lack talent, intelligence, or ambition, but because they lack clarity, structure, accountability, strategic guidance, or someone who can help them simplify complexity into meaningful momentum.

Over the years, people consistently came to me with questions:
• How do I move this idea forward?
• How do I organize all these moving pieces?
• How do I transition out of my current career?
• How do I monetize what I already know?
• How do I stop overthinking and actually build something?

Sometimes people needed encouragement and perspective. Other times they needed someone to step directly into the operational or strategic side of what they were struggling with and help them untangle it.

That’s really where Momentum Advisory came from.

I realized my work naturally existed somewhere between coaching and consulting. The coaching side helped people reconnect with confidence, vision, and momentum. The consulting side helped identify practical next steps, systems, strategy, structure, and implementation.

Over time, that evolved into a broader advisory model rooted in real-world execution, leadership, entrepreneurship, systems thinking, and human-centered growth.
Today, Momentum Advisory helps entrepreneurs, professionals, nonprofit leaders, and builders create clarity, structure, strategy, and momentum around what they’re building next.

The work blends:
• strategic advisory
• leadership development
• accountability
• operational thinking
• implementation support
• entrepreneurial guidance
• and systems development

What sets the work apart is that it’s grounded in lived experience — not abstract theory or internet entrepreneurship culture. I’ve had the opportunity to build businesses, lead teams, deploy capital, navigate uncertainty, cultivate partnerships, and help organizations grow through both opportunity and adversity.

I also believe deeply that many people already possess far more value than they realize.

What they often need is not another motivational quote or another online course.
They need clarity.
They need structure.
They need accountability.
They need strategic guidance.
And they need momentum.

That belief ultimately led to the creation of the NYOP Access Model™, a flexible “Name Your Own Price” advisory structure designed to make meaningful strategic guidance more accessible to people in different financial seasons of life.

At its core, Momentum Advisory exists to help capable people move from uncertainty into meaningful execution.

The focus is not just inspiration.

The focus is momentum.

Do you have any stories of times when you almost missed payroll or any other near death experiences for your business?

Absolutely. Entrepreneurship has a way of humbling you very quickly, and I think almost every meaningful business journey has moments where things feel uncertain, fragile, or even impossible.

When I founded Coffee at The Point in Denver’s historic Five Points neighborhood, I wasn’t coming from a traditional coffee background. I had a vision for building something larger than a coffee shop, a community-centered gathering place that brought people together through culture, conversation, entrepreneurship, and connection. But vision alone doesn’t pay rent, cover payroll, or solve operational problems.

There were definitely moments where things felt incredibly tight financially. Moments where we were trying to figure out how to keep momentum moving while balancing payroll, vendors, growth, staffing, construction costs, operational challenges, and the unpredictability that comes with entrepreneurship.

I remember periods where one delayed payment, one slow month, or one unexpected expense could create real pressure. There were moments where I genuinely didn’t know exactly how everything would come together, but somehow, through persistence, creativity, relationships, and continued movement, solutions would begin to appear.

One of the biggest lessons I learned is that entrepreneurship often requires you to keep taking the next right step before the entire pathway is visible.

Sometimes the breakthrough came through:
• a conversation
• a partnership
• an unexpected opportunity
• community support
• creative problem-solving
• or simply refusing to quit when things felt uncertain.

I’ve learned that resilience in business is not always loud or dramatic. Sometimes resilience is quietly continuing to move forward while carrying uncertainty that no one else sees.

Later, while helping deploy more than $17 million in grants and loans to small businesses across Colorado, I realized how universal those experiences really are. So many entrepreneurs were carrying the same pressures:
• making payroll
• navigating cash flow
• uncertainty around growth
• fear of failure
• operational overwhelm
• and trying to hold everything together while still leading others.

That experience deepened my empathy for entrepreneurs tremendously.

What I’m most proud of is not that every season was easy, because it absolutely wasn’t. What I’m proud of is continuing to build through uncertainty, continuing to learn, continuing to adapt, and continuing to help other people move through difficult seasons as well.

I think one of the greatest misconceptions about entrepreneurship is that successful people always know exactly what they’re doing. In reality, many entrepreneurs are simply learning how to stay resourceful long enough for momentum to eventually catch up to their vision.

And in many ways, that realization became one of the foundations of Momentum Advisory.
A little resilience, a little patience, strategic thinking, strong relationships, and a willingness to keep moving often create openings that weren’t visible at the beginning.

How about pivoting – can you share the story of a time you’ve had to pivot?

One of the biggest lessons I’ve learned throughout my life and career is that pivoting does not mean starting over. A pivot often means carrying your experience, frameworks, leadership, and systems into a new environment and learning how to apply them differently.

I’ve had several major pivots throughout my journey.

When I founded Coffee at The Point in Denver’s historic Five Points neighborhood, I wasn’t coming from a traditional coffee industry background. On paper, it probably didn’t make much sense. But what I realized quickly was that building a successful coffeehouse was not simply about coffee. It was about leadership, systems, culture, operations, relationship-building, customer experience, strategic growth, and creating something meaningful for people.

Over more than a decade, we built one of the most recognized coffee shops in the state, operated a 3,000-square-foot community-centered space, built a team, developed systems, cultivated partnerships, and won 13 local and national awards.

That experience taught me something incredibly important:
the frameworks behind growth often transfer across industries.

Later, I co-founded Pure Hospitality, which expanded my understanding of hospitality, development, partnerships, operational scaling, and long-term business strategy. From there, I pivoted again into Energize Colorado, where I helped direct more than $17 million in grants and loans to small businesses across the state during one of the most difficult periods many entrepreneurs had ever faced.

At first glance, hospitality and statewide economic recovery work may seem completely unrelated. But I realized I was still solving many of the same problems:
• helping people navigate uncertainty
• creating systems
• building momentum
• solving operational challenges
• leading through complexity
• and helping organizations and entrepreneurs move forward strategically.
Later, I transitioned again into national leadership work with No Labels, helping cultivate fundraising strategy, coalition-building, organizational growth, and leadership development efforts across all 435 congressional districts.

And now, Momentum Advisory is really the culmination of all of those experiences coming together.

What became increasingly clear over the years is that I was never simply building coffee shops, leading programs, or helping organizations grow. At the core, I was helping people create clarity, strategy, systems, leadership, and momentum.

That realization changed how I viewed pivoting entirely.

Many people think pivoting means abandoning your past experience. I’ve learned the opposite is often true. The most successful pivots happen when you recognize that your greatest value may not be tied to one specific industry, it may be tied to the frameworks, leadership abilities, systems thinking, and problem-solving approaches you’ve developed over time.

For me, each pivot wasn’t really starting over.

It was carrying forward the lessons, systems, resilience, leadership, and strategic thinking from one chapter into the next.

And in many ways, that philosophy became one of the foundations of Momentum Advisory itself:
helping people recognize that they are often far more transferable, capable, and valuable than they realize.

Contact Info:

• Website: https://www.ryancobbins.com/
• Instagram: https://www.instagram.com/ryancobbins/
• Facebook: https://www.facebook.com/ryancobbins
• Linkedin: https://www.linkedin.com/in/ryancobbins/
• Youtube: https://www.youtube.com/@RyanCobbins