The Power of Due Diligence: Why Researching Your Relationships—Personal, Professional, and Beyond—Matters More Than Ever

/ Kevin O'Leary
The Power of Due Diligence: Why Researching Your Relationships—Personal, Professional, and Beyond—Matters More Than Ever

In an era where impulsive decisions, instant gratification, and surface-level connections dominate our lives, taking the time to dig deeper has become a lost art.

Yet, some voices, like that of Kevin O’Leary—entrepreneur, investor, and television personality—resonate clearly among the noise, reminding us of one timeless truth: due diligence is everything.

A recent post from Dose of Society sparked an important discussion on this very subject. Drawing inspiration from O’Leary’s perspective, it highlighted the critical need for evaluating not just potential romantic partners, but any relationship that demands your energy, time, and trust. Whether it’s about love, business, or a major life decision, aligning with the right people and opportunities requires more than just gut feelings—it calls for strategic research and honest introspection.

So, what does it really mean to “do your due diligence”? And why is it vital for building meaningful, aligned, and successful partnerships in any area of life? In this deep-dive, we explore the importance of informed decision-making, the role values play in compatibility, and the practical steps available to anyone aiming to forge connections that truly count.

Let’s begin.

Table of Contents

1. Understanding Due Diligence in Everyday Life

Due diligence is often a term we associate with mergers, acquisitions, and legal formalities. However, its principles extend far beyond boardrooms and financial audits. It’s a mindset—an approach that calls for intent, awareness, and scrutiny before engaging in any commitment that holds weight.

At its core, due diligence is about informed choices. Whether you’re about to start a new romantic relationship, enter into a business partnership, or accept a job offer, researching the background, values, and long-term implications should precede your final decision.

In personal contexts, we often see emotional desire take the front seat, and while emotions are important, they shouldn’t replace logic. Every meaningful commitment requires knowing who or what you’re getting involved with.

2. Relationships Through the Lens of Compatibility

Compatibility isn’t just about shared hobbies or mutual attraction. True compatibility speaks to alignment in values, long-term goals, and communication styles. It’s about how two people—or entities—interact on deeper levels.

Kevin O’Leary often says, “Money and emotions don’t mix.” While this typically applies to finances, it’s also relevant in choosing our relationships. Making choices based solely on surface-level appeal often leads to disappointment.

So, how do you evaluate compatibility?

First, know your non-negotiables. Whether it’s integrity, ambition, or family values—identify them. Then, look for alignment before diving into anything serious.

This doesn’t mean you’re being transactional—it means you respect your time and emotional bandwidth enough to demand something meaningful in return.

3. Kevin O’Leary’s Take: Business Principles Applied to Life

Kevin O’Leary’s career is built upon the ability to identify winning investments—financial and personal. At the heart of his wisdom is a pragmatic approach: assess risk, understand returns, and align with people whose visions match yours.

What stands out is his belief that relationships—whether personal or business—deserve the same vetting process. He often discusses how poor partnerships can destroy a business, consume valuable energy, and stall growth.

If we treated relationships with the same filters as we do when managing a portfolio—evaluating past performance, risk tolerance…