I’m focused on supporting your journey.

Hi, I’m Chris Caldwell. I work with founders in software startups and digital agencies who are passionate, driven, motivated, ambitious, creative, and forward thinking. They have big dreams and are willing to meet obstacles head-on and work through an overwhelming number of challenges to see their dreams realized.

These people are smart, create their own path, challenge the status quo, and seek to make a positive impact on the world and those around them. I’m here to help these people, people like you, make their dreams a reality.

An image of Chris Caldwell in a hero pose in a cyberpunk environment that was generated by AI.

My purpose

I’ve been on my own journey and through self-discovery and collaboration with others, a consistent thread has emerged in my work. This thread encompasses the a quality that inspires and motivates me everyday. It’s a quality that others have pointed out, benefited from, and has helped create exceptional value by working with me.

Before I tell you what this quality is, let me tell you a short story.

I once interviewed at Amazon. The hiring process focuses on identifying individuals who embody the company's core values. Amazon has a set of leadership principles they use to find people who will thrive in their culture and continue driving the company forward in a cohesive way. It’s a great approach to ensuring a long-term competitive advantage through cultural quality assurance. During the process, everyone is given feedback on their greatest strength as it relates to their leadership principles. Having undergone this rigorous process myself, they eventually did the big reveal at the end about what my "superpower" is...

Thinking Big. Amazon summarizes this as “Thinking small is a self-fulfilling prophecy. Leaders create and communicate a bold direction that inspires results. They think differently and look around corners for ways to serve customers.”

To think big is to create an inspiring vision that motivates action, connecting the present work to future outcomes. It involves holistic problem-solving, collaborating with others to chart a path forward and overcome obstacles. By supporting and inspiring others, we build their confidence and self-belief, enabling them to become the best version of themselves and achieve their dreams and goals.

Your dream isn’t a reflection of your current situation. You want to put in the work to get your idea or business to where it will be down the road, whether that’s a year, five years, or ten years into the future, and I’d like to help you realize your dream.

I want to use my ability to think big to support you in your journey towards creating an exceptional company, team, and digital products — just like I’ve helped these founders and teams created greater success.

Chris has an incredible ability to think expansively about problems, constantly providing new perspectives about how organizations can operate better.

He is patient, humble and dedicated with those he works with, maintaining a safe space for debate and molding ideas. As a founder, he has used his strengths to unlock high leverage opportunities, and shows support and encouragement for my strengths.

Brian Ragone

Chris is a great systems thinker, and he knows how to lead a team holistically to tackle a problem.

Bethani Jade

Chris actively helps others succeed and was instrumental for change in the senior team and strategy.

Lanny McNie

Chris takes the necessary time to weave into your team and truly understand what is needed, then he finds effective ways to fill the gaps.

David Johnston

I feel like I am working with a true consultant that wants to understand our company's needs, my needs and is making a great effort to help us achieve our goals as opposed to just shaking the trees.

Derek Kadis

Chris is a deep thinker. He’s also a rare combination: a craftsperson turned team leader, someone who actually knows the power of true, people-focused leadership and can execute on that. I’ve seen him transform culture and efficiency while building rapport within an organization – often, outcomes that are at odds with one another.

Jeff Archibald

My Story

I have a 20+ year track record of working in the tech industry, during which I have gained experience in a variety of areas. I have owned and operated my own company, collaborated with founders to develop teams and departments from the ground up, and assisted businesses in creating exceptional products and experiences. Throughout the majority of my career, I have specialized in leading small teams that use cutting-edge technologies to create software, including mobile and web applications, SaaS platforms, VR, TV, and consumer robotics. I have worked with businesses and teams at all stages of development, from pre-seed startups to post-IPO companies and global enterprises that have been operating for over 50 years, with customers worldwide.

One of the most memorable moments in my career was visiting L.A. for a project I worked on that celebrated Atari's 40th Anniversary. I had the privilege of appearing in a promotional video alongside Nolan Bushnell, the founder of Atari and Chuck E. Cheese.

Throughout my career, I have had the opportunity to work with some of the most prominent technology companies, including Microsoft, Google, and Shopify, and have contributed to successful projects for brands like PGA Tour and Atari. In addition to working with established companies, I have also supported the growth of early-stage startups such as Puzzle, and Omnee, For these ventures, I have focused on helping founders establish a strong organizational culture and develop digital products while coaching and mentoring their teams to navigate the challenges of building new products and improving existing ones.

Although my career has been rewarding, I have experienced difficult moments, failures, and setbacks along the way. I founded my first business at the age of 24, which turned profitable, but I rushed to scale it before it was adequately prepared, resulting in collapse. At times, I was unaware of my blind spots or areas where I was letting my team down, resulting in significant turnover, leaving me in a precarious position of fulfilling customer commitments, rebuilding the team, and growing as a leader to avoid similar situations in the future. There were occasions where the path forward was unclear, problems weren’t visible to me, and I needed the help and perspectives of others to see the situation I was unintentionally creating. In these moments of growth, I shored up my knowledge, developed systems, and implemented frameworks to collaborate with my team, enabling us to figure things out together and navigate the business towards a brighter future. Instead of stressing about having all the the answers or being solely responsible for navigating teams through challenges, we trusted and supported each other to overcome our individual and collective challenges to develop the business and each other.

Apart from the evident challenges, I have encountered subtle and complex issues that I did not foresee earlier in my career. As an owner, boss, or individual in a position of authority, it can be challenging to obtain candid feedback that is critical to developing as a leader, making effective decisions, and building a winning strategy. Falling into traps that make you the bottleneck, create a low-trust environment, alienate your team, or waste valuable time and resources focused on the wrong problems can hinder your ability to realize your dreams. It is crucial to remain vigilant and actively seek feedback, engage with your team, and regularly reflect on your leadership approach to avoid these pitfalls.

Throughout my career, I have developed a leadership and coaching approach that is grounded in human-centered design and design thinking principles. These methodologies are highly effective problem-solving frameworks that prioritize identifying the right problems, for the right people, and solving them in the right ways. They involve listening to people, understanding their needs, exploring solutions, and iterating until a solution is created that effectively addresses problems in a valuable way across all stakeholders connected to your business. It's important to learn from both what works and what doesn't to continuously improve. This approach fosters a culture of collaboration, empathy, and continuous improvement, which is essential for building successful products, high-performing teams, and exceptional businesses.

I integrate design thinking principles with fundamentals in strategy, systems thinking, organizational design, systems and process development, collaborative problem-solving, leadership, and management. By applying these concepts, I assist founders like you in guiding your business, teams, and products towards success in a faster, more effective, and collaborative way.

Together, we will:

My values


When ideas can be openly challenged and discussed, regardless of position or tenure, innovation, diversity, inclusion, and positive feedback thrive. z is key to creating high-trust, high-support structures within teams that empower individuals to take ownership, leadership, and accelerate their growth. This requires creating a psychologically safe environment that fosters high-functioning teams and allows everyone to shine.


Valuing ownership empowers individuals to shape themselves, their work, and their environment with a proactive mindset. By focusing on areas within their control, they create positive outcomes and move towards a brighter future with determined optimism. This concept, coined as 'definite optimism' by Peter Theil in his book Zero to One, drives individuals towards success.


Leaders bridge the gap between current reality and an inspiring future by creating strategies for change. Anyone can practice leadership, regardless of position or tenure. Teams that practice self-leadership and self-management drive personal growth and clarity of purpose, empowering each individual to become a leader.


Celebrating small victories is essential for overcoming challenges and inspiring people. It motivates us, maintains a positive outlook, and builds momentum towards larger goals. Reflecting on progress helps us learn and grow, stay motivated, overcome obstacles, and achieve success.

Making &

Creating and sharing help us learn and master new skills, fostering a growth mindset focused on overcoming challenges. By deliberately practicing and incorporating play, seeking and receiving feedback, we become better versions of ourselves with each intentional effort.

Diversity &

By embracing different perspectives, we improve our ability to think, solve problems, and make decision as individuals and teams. Inclusive problem-exploration and problem-solving help us identify and minimize bias, dogmatic thinking, and faulty assumptions, freeing us to do our best work.

Who I serve

There are a few things I look for in a potential collaboration that are indicators of a relationship that will be successful and produce great outcomes for everyone while we work together: Leadership, Motivation, Candor, and Coach-ability.