Damon Flowers | Modern Operators
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Short Bio
Damon has spent the last 22 years building, scaling, and exiting companies across diverse niches like Saas, eCommerce, Training/Coaching, and Real Estate, taking his last company from $3.5M to $30M in two years. His real obsession though is unlocking human potential…knowing that our inner world shapes our outer results. Today, he combines proven business growth strategies with deep inner work to help entrepreneurs rewire their minds for growth and transition from being the glue that holds their business together to becoming the leader their company needs. His latest venture, Modern Operators, helps entrepreneurs reach their vision faster through a unified Company OS that leverages custom trained AI and aligns staff to unlock 2-5x productivity gains.
Long Bio
Over the last 22 years, Damon has started, failed, licensed, and exited multiple businesses across real estate, training, SaaS, private lending, coaching, and e-commerce. In his last two ventures, he scaled a training/coaching company from zero to $12M in five years and then grew an ecommerce co from $3.5M to $30M in just two years. He’s also led mindset workshops and personally coached thousands of entrepreneurs, plus helped countless real estate investors build their portfolios.
But beyond the numbers, his real obsession has always been unlocking human potential.
He’s spent the past 20 years studying the mind…why we do what we do and how to rewire ourselves for growth. Mediation and his spiritual walk are at the center of his daily practice now. This has helped him stay grounded through the highs and lows of entrepreneurship and life. He believes our inner world shapes our outer results…and that personal transformation is the secret weapon of happiness and sustainable business growth.
He’s a husband of 25 years, father of three, lifelong reader (thousands of books and counting), and an avid outdoorsman. Nature is his reset button. It's where he reconnects, reflects, and remembers what really matters.
If you could write an intro to the podcast, what would it be?
Today's guest has spent 22 years in the trenches of entrepreneurship…building, scaling, and exiting multiple companies, including taking an eCommerce business from $3.5 million to $30 million in just two years. But what makes Damon Flowers truly unique is that he's spent an equal amount of time, over 20 years, studying something most entrepreneurs ignore: the mind itself.
While most founders are chasing the next growth hack or productivity tool, Damon discovered the real secret hiding in plain sight. Through thousands of hours in meditation, deep inner work, and studying human potential, he unlocked a counterintuitive truth: discipline isn't about forcing yourself to do hard things. It's about bringing yourself into such deep alignment that discipline stops being a burden and becomes a gift.
Today, through Modern Operators, Damon helps founder-led businesses in the $2M to $30M range break through the chaos and build companies that execute predictably without the founder holding everything together. But he doesn't do it with more tactics or tools. He does it by helping leaders rewire their relationship with themselves first…because sustainable growth on the outside always begins with transformation on the inside.
If you've ever felt like you're working harder than ever but getting diminishing returns, or if you've wondered why some business moves feel effortless while others drain you completely, this conversation will change how you think about discipline, growth, and what it really takes to scale.
Welcome, Damon Flowers.
Questions & Answers…
Please list five topics you would love to discuss during the interview that are relevant to our audience (Founders & entrepreneurs running businesses in the $1M to $50M range).
- How to transition from stuck in the day-to-day to leading a business that executes predictably and without you as the glue that holds it all together.
- From firefighting to leading
- From stuck in the weeds to back in control
- From doing everything to leading a business that executes like you would
- From heroic effort to solid team execution
- What makes a founder great at getting the business going is the biggest roadblock that holds back scale and how to overcome it
- Why slapping on AI tools, workflows, etc is proven not to work and what to do instead
- Why Operational Leverage is the new marketing
- How the inner game is ultimately what drives outer results
- The phases that a company must go through to grow long term or sell for a premier exit
What’s your area of expertise?
I operate at the intersection of modern operations and human potential. I've spent 22 years scaling companies while spending equal time studying the mind, meditation, and inner transformation. My expertise is in helping founder led companies transition to predictable, rapid, and sustainable growth while removing themselves as the bottleneck that holds everything together..
How are these topics specifically valuable for founders, entrepreneurs and owners of small businesses?
SMB owners are dealing with what has become a more difficult business environment (uncertainty, increased risk, more competition/noise, faster pace of innovation, and more). This requires companies to move faster, adjust to higher risk thresholds, be more adaptable, and meet the needs of the market quicker.
We are operational experts who deeply understand how to drive growth. We’re also business owners who have founded, scaled, licensed, failed, and exited multiple businesses over the last 20+ years and deeply understand what it takes to build and grow a business successfully.
Questions to Pull From that Damon can answer
Modern Operating System Questions
- What exactly is a Modern Operating System, and how is it different from just having good processes or using project management tools?
- Walk us through how a Modern Operating System actually works in a real business—what does it look like day-to-day for a founder and their team?
Founder Journey & Mindset Questions
- You've scaled multiple companies. What was the pivotal moment when you realized the skills that made you successful launching the business were actually holding you back when scaling the business?
- You talk about spending 15+ years studying the mind, meditation, and inner transformation alongside building businesses. How has your "inner game" changed over time, and what's one practice that's been most transformational?
- It seems most founders hit a ceiling between $2M and $10M where growth starts creating more chaos instead of more freedom. What's the root cause of this pattern, and what should they do to break through?
Operational Strategy Questions
- You say "operational leverage is the new marketing." That's a bold statement. Can you unpack what that means and why operations has become the competitive advantage?
- Everyone's talking about AI agents and automation, but you've said that just "slapping on AI tools" doesn't work. What's the prerequisite work that has to happen before AI can actually deliver leverage in a business?
Work-Life Integration Questions
- As a husband and father of three who's built multiple successful companies, how do you think about work-life balance differently now versus when you were in your 20s or 30s building your first ventures?
- Founder burnout is epidemic—60 to 80 hour weeks, chronic decision fatigue, health declining. You help founders escape this pattern. What's the counterintuitive move that creates the most immediate relief?
Strategic Wisdom Question
- If you could sit down with a founder doing $5M in revenue who wants to 3x in the next 24 months, what are the diagnostic questions you'd ask them to help identify whether they're ready to scale or if they need to fix their foundation first?
What makes you the perfect guest for Us?
I bring 20+ years of in-the-trenches experience scaling my own ventures and now helping founder-led businesses in the $2M to $30M space grow more rapidly and predictably. Your audience won't get theory. They'll get battle-tested frameworks I use daily with real companies.
I'm not a consultant selling advice I've never executed. In my last venture, I took over a struggling ecommerce company and grew it from $3.5M to $30M in 2 years and optimized it for a premier exit.
I talk about the unsexy truth…that operations is the new competitive advantage. I challenge the hustle-and-grind mentality and show founders how to lead instead of firefight.
Escaping founder dependency, building teams that execute the way the founder would, turning operational chaos into predictable growth, structuring an organization for AI agents that deliver organizational leverage
I challenge business owners to think differently about how they're building their companies.
What is your starting story? How, when, and why did you start Modern Operators?
The idea for Modern Operators hit me after 20+ years of building and scaling companies and watching the same pattern repeat everywhere I looked.
I'd grown a training company from zero to $12 million in 5 years. Scaled an e-commerce business from $3.5 million to $30 million in just two years. I'd been the operator, the strategist, the therapist, the guy called in to fix what was broken. And across every industry—real estate, SaaS, coaching…I kept seeing the same ceiling.
Founders stuck between $2 million and $10 million, working themselves into the ground.
They'd figured out sales. They had customers. But everything ran through them. Their teams waited for decisions. Systems lived in people's heads. Growth meant more chaos, not more freedom.
I'd cracked this problem…building the playbooks, installing the systems, getting founders out of the weeds. But every time, it was custom. Expensive. Took 12 to 24 months or more..
Then in early 2025, my co-founder Mark and I were collaborating on another project and had this realization: What if we could codify all of this? Take the frameworks that work at $50 million companies and make them accessible to founders doing $2 to $10 million. Not through 1-1 six-figure consulting. Through a modern operating system they could actually use.
We launched Modern Operators in May 2025 with a simple mission: help founder-led businesses transition from firefighting to leading…from complexity to predictable, sustainable growth.
The "why" is personal. I've lived the grind. I know what it's like to be the bottleneck. And I've seen what happens when you get the systems right. Your business doesn't just grow…it transforms. You get your time back. Your team executes without you. And you finally get to lead instead of survive.
That's the company we're building.
Articles, podcasts, interviews, or social media. What are some of the best sources we can visit to learn more about your thinking, story and achievements?
- Modern Operators Newsletter Archive - https://modernoperators.com/archive
- The Modern Operators subreddit - https://www.reddit.com/r/ModernOperators/
- LinkedIn Damon - https://www.linkedin.com/in/damonflowers/
- How to Build a Company that Runs Without You - https://www.youtube.com/watch?v=7iCPDcIsyeU
Briefly describe the system, framework, and/or methodology you could share during an interview. Here are just a few
- VTEC™️ - Helping business owners translate what makes them great in the early stages into an organization with teams and staff who execute the way they wood (and better)
- The Modern Identity - How to structure information in your business so your staff and AI have the context to win
- Rhythm Cycles - How to build feedback loops into your business so lessons continue strengthening your foundation and help prepare your org for exponential growth
- First Principles Thinking - How to think about growth so you are are prepared to experience it within your company
- Modern Day Operational Organization - How a modern day AI enabled company looks different from a traditional company to drive AI deployment that yields highest results
What’s one proven strategy, framework, or lesson you’ve used that has directly driven results in your business or life?
It's really hard to pick just one...
One that helps founders make the transition from selling products/services to growing a sustainable business is understanding what I call VTEC or Vision to Execution Cycle. This is the drive that got them where they are in businenss but also reveals why most business owners become their biggest bottleneck in their business. Backed by Mckinsey and HBR case studies, it's a method I developed to transition a team towards “Aligned Ownership” so that the founder can confidently move to leading the business and no longer acting as the glue holding it all together.
What area of your expertise do you feel you’ve truly “unlocked,” and how can listeners apply it to their own growth?
Personally, it is understanding how our inner game determines our outer results and how to change if you don’t like it. Professionally, I help founding teams make the transition from working in their business to leading and growing predictably. We do that by redesigning Operations as the hub and growth engine of modern day companies, bringing teams into alignment and unlocking 2-5x growth through AI agents. To reach the scale stage, we must go through foundation building and optimization. Getting that right unlocks predictable and sustainable scale that doesn't break the business along the way.
What was a major challenge or turning point that shaped the way you operate or lead today?
Watching how some things in business and life were easy for me and others weren't. Seeing how action I wanted to take was easy for others and not me. Then, spending the next 20+ years learning how our mind works and how to reprogram it for the results we want.
About Modern Operators
Modern Operators is a systems-first growth partner for founder-led companies doing $500k–$10M who want to scale with clarity, calm, and predictable momentum. Instead of relying on heroic founders, scattered tools, or reactionary decision-making, MO equips teams with a modern operating system…a unified layer of vision, planning, execution, automation, and AI that allows the business to run smoother, faster, and more intelligently.
Co-founded by Damon Flowers and Mark Malian, Modern Operators brings together decades of deep operating experience, brand strategy, and systems design to help companies move from reactive growth to a stable, scalable rhythm.
- Damon Flowers has spent 20+ years building and scaling companies from early-stage to eight-figure outcomes. He is known for architecting operating systems, transforming chaotic teams into aligned execution machines, and mentoring founders and leaders through the transition from “doing everything” to building a company that grows beyond them. His work blends strategic clarity, operational structure, and the practical integration of AI into day-to-day workflows.
- Mark Malian brings 7+ years of experience in growth strategy, brand positioning, and systems automation inside agencies and product companies. His expertise lies in turning complex processes into clean, scalable systems…especially in marketing, sales, and customer operations, so teams can produce consistent pipeline, shorten deal cycles, and unlock predictable growth.
Together, Damon and Mark built Modern Operators to guide founders through a new era of business…one where clear structure replaces chaos, AI amplifies human capability, and a modern Company OS becomes the foundation for long-term, scalable success.
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Need to Contact Me Directly?
Email Beatrice, Modern Operators PR Agent
…at hello AT mail dot modernoperators dot com