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

Maximilian, appreciate you joining us today. One of our favorite things to brainstorm about with friends who’ve built something entrepreneurial is what they would do differently if they were to start over today. Surely, there are things you’ve learned that would allow you to do it over faster, more efficiently. We’d love to hear how you would go about setting things up if you were starting over today, knowing everything that you already know.

Looking back, I would be less hard on myself and adopt the principles from the book The Gap and The Gain. Instead of constantly measuring myself against others and my ideal, I would focus on my own progress—comparing where I am today to where I started, rather than where others are. For much of my business journey, I fell into the trap of comparison, always looking at where I should be instead of recognizing how far I had already come. Early on, I believed success meant keeping up with industry leaders, growing as fast as possible, and proving my worth through external validation. That mindset created unnecessary pressure, making me feel like I was never doing enough, even when I was building something truly valuable.

Over time, I started realizing that real success wasn’t about how I measured up to others—it was about being aligned with my own goals and values and measuring backyards of my previous success. A turning point for me was recognizing that every win/gain, no matter how small, was a step forward. Instead of feeling frustrated about where I wasn’t, I began appreciating the progress I had made. If I could do it over again, I would have spent more time acknowledging my growth, trusting the process, and letting go of the pressure to constantly push harder. I would have also been more intentional about celebrating wins along the way rather than just moving to the next goal without taking a moment to appreciate what I had accomplished.

I now see how much I let self-judgment dictate my experience—always thinking I should be further along, always feeling like I needed to do more. Today, I’m learning to operate with more self-trust and perspective, embracing the fact that the journey itself is the reward. If I had internalized this earlier, I could have enjoyed the ride more, had more confidence in my decisions, and let go of the unnecessary stress of comparison. Now, my focus is on continuing to build a business and life that feels truly aligned, knowing that success comes from within—not from where I stand in relation to others.

2. Question:
I started focusing solely on my progress—looking back at my gains rather than where I thought I should be—and as a result, I’ve been able to move much faster in our business. If I were starting over, this is exactly what I would do differently from the beginning.

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

can you please tell our readers about yourself, how you got into your industry:
I grew up in a self-employed household, where I saw firsthand the financial tension that comes with running a business. My parents worked hard, but the unpredictability of income and financial stress were always present. Those experiences shaped my perspective early on—I knew I didn’t want that same uncertainty for myself, and I didn’t want others to experience it either.

That’s what ultimately led me to wealth management. I wanted to help business owners, entrepreneurs, and professionals gain control over their finances, so they could build a life of security, freedom, and opportunity—without the constant stress of wondering if they were making the right decisions. Over the years, I’ve seen how having a clear financial strategy can transform lives, giving people the confidence to grow their wealth while staying aligned with their personal and professional goals. My mission is to make sure my clients don’t just accumulate wealth, but that they build a financial foundation that supports the life they truly want to live.

what type of products/services/creative works you provide, what problems you solve for your clients and/or what you think sets you apart from others.
I co-founded Truly Aligned with my wife, creating a wealth management firm that goes beyond traditional financial planning. Our mission is to help business owners, entrepreneurs, and high-achieving professionals align their wealth with their life journey—because financial success isn’t just about numbers, it’s about creating a life of purpose, freedom, and fulfillment.

Many of our clients come to us overwhelmed by financial complexity—navigating tax optimization, investment strategy, business structuring, and long-term financial security. They don’t just want growth; they want clarity, confidence, and a financial strategy that supports the life they envision.

At Truly Aligned, we do things differently. We don’t just manage wealth—we align it with your values, goals, and vision so that every dollar serves a meaningful purpose.

We provide:

Comprehensive wealth management, integrating tax strategy, investments, estate planning, and business financial planning.
Strategic financial planning for business owners, helping them scale, optimize taxes, and build long-term, sustainable wealth.
Guidance through major financial transitions, including business exits, real estate investments, and retirement planning.
A mindset shift around money, ensuring clients build wealth in a way that supports their personal vision—not just traditional financial metrics.
At the heart of our work is the belief that true wealth is about more than just accumulation—it’s about alignment. When your financial strategy reflects your deepest values and priorities, you gain more than financial security—you gain the freedom to live life on your own terms.

What are you most proud of and what are the main things you want potential clients/followers/fans to know about you/your brand/your work/ etc.
I’m most proud of the impact we’ve had on our clients’ lives—helping them make confident financial decisions while building a life that reflects their deepest values. Seeing our clients gain clarity, security, and the freedom to live intentionally is what drives me every day.

I’m also proud of the way we’ve built Truly Aligned—a firm that reflects our values and allows us to serve people in a way that’s both meaningful and fulfilling. We’ve created a space where financial planning isn’t just about wealth accumulation—it’s about aligning money with purpose, growth, and long-term vision.

On a personal level, my journey has been just as transformative. I’ve learned to shift away from self-judgment and comparison, embracing a mindset that measures success by my own progress rather than external benchmarks. This shift has allowed me to move faster, make better decisions, and truly enjoy the process of building this business.

What I Want Potential Clients to Know
If you’re looking for more than just financial stability—if you want clarity, alignment, and a strategy that supports the life you truly want—we’re here to help. Financial planning isn’t just about numbers; it’s about creating a future that excites you and gives you the freedom to live life on your terms.

We take the time to understand what matters most to you and design a tailored wealth strategy that reflects your values, goals, and lifestyle. If that resonates with you, let’s connect and build a plan that feels truly aligned.

Let’s talk about resilience next – do you have a story you can share with us?

The Power of One More Day
When I started my business, the uncertainty felt unbearable. Setbacks piled up, progress felt slow, and quitting seemed like the easiest way out. In those moments, I developed a habit—a simple promise to myself: “If I still feel like quitting tomorrow, I can quit.”

Every morning, I’d wake up with just enough energy to try again. Maybe I didn’t have all the answers, but I had one more push, one more effort to give. Over time, those small decisions to keep going—one day at a time—became the foundation of everything I’ve built.

Resilience isn’t about never wanting to quit; it’s about trusting that tomorrow holds the potential for a breakthrough, a fresh perspective, or just a little more clarity. Looking back, I see that every time I chose to wake up and show up, I was moving forward—even when I couldn’t see it. As long as you keep showing up, you’re still in the game—and that’s where transformation happens.

What’s a lesson you had to unlearn and what’s the backstory?

For most of my career, I believed that success was something to be earned through relentless effort—that the harder I worked, the more successful I’d become. I also tied my identity to external validation, measuring my worth by achievements, numbers, and how others perceived my progress. If I wasn’t growing fast enough, making enough, or reaching the next milestone quickly, I felt like I was falling behind.

This mindset fueled me for years, pushing me to work harder, take on more, and constantly chase the next level. But no matter how much I achieved, it never felt like enough. The breaking point came when I realized that no amount of effort would ever fill the void I was trying to satisfy. That’s when I started to unlearn the idea that working harder always leads to better results and that external success defines self-worth.

What I’ve learned is that real success comes from alignment and living out my core values, not just effort. It’s about focusing on the right things and leveraging my business effectively, not just doing more. It’s about measuring my progress based on my own vision, not someone else’s version of success. Now, I define success by how aligned I feel, how much freedom I have, and whether my work energizes me rather than drains me.

Unlearning these beliefs hasn’t been easy, but it’s allowed me to build a business and a life that truly feel fulfilling—not just impressive on paper.

Contact Info:

• Website: https://trulyalignedinc.com/
• Linkedin: https://www.linkedin.com/in/maxclifford/
• Youtube: https://www.youtube.com/@TrulyAlignedWealthManagment
• Other: https://www.google.com/search?q=truly+aligned+boulder&rlz=1C1ONGR_enUS1049US1049&oq=truly&gs_lcrp=EgZjaHJvbWUqCAgCEEUYJxg7MgYIABBFGDwyBggBEEUYPDIICAIQRRgnGDsyEAgDEC4YxwEYsQMY0QMYgAQyBggEEEUYPDIGCAUQRRhBMgYIBhBFGEEyBggHEEUYPNIBCDI0MjZqMGo3qAIAsAIA&sourceid=chrome&ie=UTF-8