Some of the biggest opportunities in life begin with a calculated leap into the unknown. In this episode of the Burning the Ships Podcast, Mike Cobb joins host Jason Seward to share the entrepreneurial journey that took him from the computer industry to building businesses throughout Latin America. Along the way, they discuss taking calculated risks in entrepreneurship, leadership, raising globally minded children, and why the most successful companies are built with a 100-year mindset rather than a short-term exit strategy.
Watch the full conversation below.
Taking Calculated Risk in Entrepreneurship and Building Businesses That Last
Leaving a secure corporate career to pursue entrepreneurship is often described as “burning the ships,” but Mike offers a more nuanced perspective. Looking back on the years he spent building an international mortgage company while still working in the computer industry, he argues that the best entrepreneurial decisions aren’t reckless leaps: they’re calculated ones. Success comes from understanding the real downside, developing a solid business plan, inviting others to challenge your assumptions, and recognizing that the fear of failure is often far greater than the reality.
Mike also reflects on the 14 years his family spent living in Nicaragua after what was originally intended to be a short-term move. Raising his daughters abroad introduced them to the concept of “third culture kids,” helping them understand from an early age that different countries have different customs, perspectives, and ways of life. For Mike, the experience reinforced the idea that a richer quality of life isn’t defined by geography alone, but by the experiences, relationships, and perspectives we gain along the way.
That long-term mindset extends beyond family life and into business. Rather than focusing solely on developing successful projects, Mike explains how ECI Development evolved into an organization built around creating communities (and companies) designed to thrive for generations. His philosophy is simple: lasting businesses aren’t built by founders alone. They’re built by leaders who invest in developing people, creating systems, and preparing the next generation to carry the mission forward.
Key takeaways from the episode
- Burning the ships should still involve careful planning. Mike believes bold action works best when it is supported by due diligence, realistic risk analysis, and a clearly written plan.
- The consequences of failure are often exaggerated in our minds. Fear can make a manageable risk feel like walking between skyscrapers when the board may only be a few feet above the ground.
- Entrepreneurs succeed by identifying unmet needs. Mike’s international career began after recognizing that overseas property buyers had no access to traditional mortgage financing.
- The people around us influence our tolerance for risk. Supportive peers, mentors, and fellow entrepreneurs can provide the encouragement needed to continue when building something becomes difficult.
- Taking calculated risk in entrepreneurship creates opportunities that fear alone never will. Mike explains that the best business decisions are built on careful planning, due diligence, and a clear understanding of the potential downside.
- Children learn resilience by being allowed to take appropriate risks. Mike and Jason discuss how good parenting includes letting children make mistakes, face consequences, and develop judgment through experience.
- Living abroad creates a deeper understanding of culture. Raising children across countries helped Mike’s daughters recognize that their own way of life was one perspective among many.
- Great leaders develop people who may eventually outgrow their original roles. Losing talented employees to bigger opportunities can be evidence that leadership and mentorship are working.
- Long-lasting companies require generational leadership. Building a 100-year business means preparing today’s leaders to develop the leaders who will follow them.
If you’re exploring a second home, residency, or investment overseas, here are a few places to start:
