We caught up with the brilliant and insightful Ryan Crownholm a few weeks ago and have shared our conversation below.
Ryan, thanks for taking the time to share your lessons with our community today. So, let’s jump right in – one of the most essential skills for unlocking our potential is self-discipline. Where does your self-discipline come from?
While I haven’t always been a disciplined individual, life has taught me the invaluable role that discipline plays in achieving long-term success and freedom. Over the years, I’ve come to appreciate the compounding effects of discipline in every facet of my life—whether it’s health, investing, education, or even personal relationships.
The beauty of discipline lies in its simplicity. For instance, dedicating just 15 minutes a day to a consistent effort—be it learning a new skill, exercising, or investing—can yield transformative results over time. This approach is far more effective and sustainable than pulling all-nighters to reach a goal or making drastic, unsustainable changes like crash dieting to lose 50 pounds.
When you adopt a disciplined approach, you’re not just aiming for immediate results; you’re setting the stage for long-term success. It’s like planting a seed and nurturing it every day, knowing that the harvest will come in due time. This is a lesson I’ve applied in my businesses as well. Consistency and discipline have been the bedrock upon which I’ve built ventures that not only generate revenue but also afford me the freedom and lifestyle I desire.
The key is to shift your perspective. When you start looking at life in terms of years and decades rather than days and weeks, you gain a profound understanding of the power of discipline. You realize that the small, consistent actions you take today will compound into significant outcomes in the future. And that’s liberating. Because ultimately, discipline doesn’t restrict your freedom; it buys it.
Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?
I’m a serial entrepreneur, investor, and U.S. Army Veteran based in Los Angeles, CA. I’m the driving force behind several ventures, including www.mysiteplan.com, www.dirtmatch.com, and Crown Capital Adventures Inc. But for me, entrepreneurship isn’t just about business; it’s a vehicle for creating freedom and autonomy in life.
What excites me the most about my work is the ability to solve real-world problems while optimizing for lifestyle. I firmly believe that your time is the most valuable asset you have, and my businesses are designed to support that philosophy. For instance, mysiteplan.com streamlines the planning process for construction projects, saving clients both time and money. On the other hand, dirtmatch.com connects people who have dirt to dispose of with those who need it, making the process efficient and eco-friendly.
But it’s not all business for me. I’m an avid lover of the outdoors, and I relish spending quality time with my family, whether we’re traveling in our motorhome or exploring backroads on a motorcycle. These experiences continually remind me why optimizing your business for lifestyle is so crucial.
I’m also deeply committed to helping others on their entrepreneurial journey. I work with Defy Ventures to empower the formerly incarcerated through book clubs, in-prison events, and halfway houses. It’s incredibly rewarding to help these individuals bring their business ideas to life, offering them a fresh start and a path to self-sufficiency.
As for what’s new, I recently released a book called ‘The Hustle Trap,’ which serves as a roadmap for achieving exactly that—more free time and increased cash flow. It’s a culmination of years of experience and insights, and I couldn’t be more excited to share it with the world.
So, whether you’re an aspiring entrepreneur, someone looking to optimize your life, or someone in need of a second chance, I invite you to join me on this journey. There’s always room for innovation, freedom, and, of course, a little adventure.
Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
Reflecting on my journey, three qualities stand out as particularly impactful: resilience, time management, and curiosity.
Resilience: As a U.S. Army Veteran and serial entrepreneur, I’ve faced my fair share of challenges. Resilience has been the backbone of my ability to adapt, learn, and grow. Whether it’s a failed venture or a personal setback, resilience allows you to bounce back stronger than before.
Advice: For those early in their journey, I’d say don’t fear failure. Embrace it as a learning opportunity. The road to success is paved with setbacks; what matters is how you recover and move forward. Remember that when you feel the urge to quit, so does everyone else. It’s those who push through those difficult times that succeed.
Time Management: I’ve always said that time is your most valuable asset. Effective time management has been crucial in balancing multiple ventures, family life, and even my passion for the outdoors. It’s not about being busy, it’s about being efficient and leveraging your time effectively.
Advice: Start by prioritizing your tasks and setting clear boundaries. Use tools and systems to automate repetitive tasks. Remember, the goal is to have a business that supports your lifestyle, not consumes it.
Curiosity: This has been the fuel for my entrepreneurial spirit. Curiosity leads to innovation, keeps you engaged, and opens doors to opportunities you might not have considered. It’s what drove me to explore various ventures and even extend my reach into social impact through Defy Ventures.
Advice: Never lose your sense of wonder. Be open to new ideas, industries, and perspectives. Curiosity will not only lead you to unexpected opportunities but also enrich your life in countless ways.
For those early in their entrepreneurial journey, my advice is to focus on these three areas. They won’t just make you a better entrepreneur; they’ll make you a better person.
Do you think it’s better to go all in on our strengths or to try to be more well-rounded by investing effort on improving areas you aren’t as strong in?
In my experience, the answer lies in a balanced approach, but with a heavier emphasis on leveraging your strengths.
Your strengths are your competitive edge; they’re what set you apart in a crowded marketplace. When you go all in on your strengths, you’re not just good at what you do—you’re exceptional. For example, my strength in understanding the value of time has been a cornerstone in all my ventures, from www.mysiteplan.com to www.dirtmatch.com. These businesses are designed to save people time, which is a direct reflection of what I excel at.
However, ignoring your weaknesses entirely can be a recipe for disaster. While you don’t have to become an expert in your weaker areas, having a basic understanding can save you from significant pitfalls. When I was starting out, I wasn’t as savvy about digital marketing as I am now. I could have outsourced it entirely, but I chose to learn the basics. This foundational knowledge helped me make more informed decisions when I did eventually bring in experts.
That said, there’s a time-saving strategy here too: delegate your weaknesses. Once you have a rudimentary understanding of your weaker areas, you can confidently delegate those tasks to people who excel in them. This allows you to focus on what you do best, thereby optimizing your time and resources.
So, my advice would be to go all in on your strengths while being mindful of your weaknesses. Learn enough about your weaker areas to manage them effectively, but don’t let them divert your focus from where you truly shine.
Contact Info:
- Website: https://www.ryancrownholm.com/
- Instagram: https://www.instagram.com/ryancrownholm/?hl=en
- Linkedin: https://www.linkedin.com/in/ryancrownholm/
- Twitter: https://www.twitter.com/Ryancrownholm

Image Credits
– Ryan Crownholm – Institute for Justice
