Its complicated.

Did you know Facebook has a relationship setting called "It's complicated"? Honestly, who decided that was a good idea? Why would anyone in a real relationship feel the need to shout to the digital world, "Oh my god! Everything is so confusing between us, and we must let Facebook know! Otherwise, I’d feel like we were living a lie. People deserve to know that our love is complicated. We must alert them to this new development!”

I just don’t get it. My husband and I have been married for 23 years, and let me tell you, we've had our fair share of complications. But why on earth would we broadcast that to the internet? We already see far too much of people’s private moments. Honestly, “It’s Complicated” feels like a redundant relationship status. If you didn’t already know, being in love is inherently complicated. That’s why you don’t see relationship statuses like Always peaceful with…” or “Harmonious living with” because complicated is almost a default of humans trying to align! Why the extra need to spell that out? Is it just extra, super-duper complicated? Would I not be able to grasp it otherwise?

If I needed to choose a status for the company I’ve been under due diligence with for the past two months, "It's complicated" would be spot on. Like, we like each other, we’re checking a lot of boxes, but we’re keeping our options open and we’re not entirely sure what the future holds.

In the interest of research, I googled what to do if your relationship is complicated. Here’s a gem from ‘Better Help’: “It can be important to remember that complications do not necessarily mean the relationship is doomed to fail. However, for the sake of your and your partner's mental health and well-being, such relationships might require work and persistence in order to shift from a difficult relationship to a healthy one.”

And that brings me to the roller-coaster world of entrepreneurship through acquisition (ETA). The internet is bursting at the seams with listicles, financial documentation checklists, and Walker Deibel's famed "target statement" formula. These resources offer seemingly solid blueprints for would-be acquirers. But what they often gloss over is the critical importance of intangible diligence—the murky waters of culture and broader market research.

Take my recent two-month deep dive into a 45-year-old fashion brand. My target statement, inspired by Deibel's template, was meticulously crafted: "I'm looking for a brand in the consumer goods or apparel space with a strong team and processes in place, needing modern marketing and Direct to Consumer (DTC) selling, and doing $300,000 to $600,000 in Seller Discretionary Earnings (SDE)." This brand checked all those boxes. On paper, it was perfect. But as Graham Greene aptly noted, "When we are not sure, we are alive." And man, have I been alive these last few months.

Uncertainty is the quintessential human condition. Intangible diligence is the messy, subjective, often deeply unsettling process of reading between the lines, understanding the soul of a business, and anticipating the undercurrents that can either propel you to success or drag you down.

With the enthusiasm of a too-eager racehorse, I plunged into the process, confident that my search parameters were foolproof and that this candidate would withstand scrutiny. My assumption? Barring any dark secrets, this would be a go, with a remarkable sponsor/company fit and goodwill aplenty.

However, my experience taught me otherwise. Anecdotal evidence, corporate reports, broader trend data, and specific comparative case studies—all this information needed to be gathered, absorbed, synthesized, and run through my personal decision-making filters. This wasn’t a mechanical process; it was more akin to detective work, requiring intuition, experience, and a healthy dose of skepticism.

I hadn’t been active in fashion for several years, so I reconnected with friends and contacts in the trenches. My trip to New York was a reality check. The badass designer/buyer I used to work with at Anthropologie commended my bravery and adventure. I tried to explain that this was a calculated move, not particularly brave. She insisted it was, comparing it to the risk of getting an STD at a secret spa party in a Brooklyn warehouse. Her point? In the unpredictable world of fashion, even the calculated can feel reckless.

Another friend, entrenched in the industry since 2012, gave me a look of incredulity when I asked if she could draw a salary yet from her venture. Her skepticism about my plan to buy this company was palpable. Then there was my new contact, who built a high-end menswear line. He wondered why, with such a long history and broad distribution, the revenue remained flat and unimpressive.

These interactions underscored a critical lesson: the stories behind the numbers matter. A company with strong sales and marketing processes on paper might still suffer from internal cultural issues, outdated market perceptions, or stagnant innovation. And while this may be where the opportunity lies, it needs to be priced accordingly. These are the insidious factors that can erode earning power, stifle growth, and sabotage a smooth transition.

In the end, intangible diligence is about embracing uncertainty and being alive to the nuances that make or break a business. It's about understanding that while target statements and financial metrics provide a necessary framework, the real work lies in uncovering the hidden truths. As I navigated this uncertain terrain, I realized that success in ETA is as much about understanding people and culture as it is about crunching numbers.

So, for anyone embarking on a similar journey, remember this: do your homework, but also trust your gut. Seek out the stories, the whispers, the unspoken dynamics. Because, the devil—and the angel—is in the details you can't see on a balance sheet. For me, I’m looking for peaceful integration with a clear path forward. “It's complicated” might sound sexy and alluring, but it's not the reliable, steady partner we all seek.