7 Things I Learned From Amy Smilovic's "Almost Reckless"

Like many Tibi fans, I was eagerly awaiting Amy Smilovic’s book, Almost Reckless, and listened to it on Audible as soon as it came out. While I already knew many bits and pieces of Tibi’s history, the book provided the full story, starting from Amy’s childhood, and added a lot of color about what it takes to build a super-successful global brand. Here are some takeaways that resonated with me most.

Almost Reckless T-shirt, Tibi pants, Le Monde Beryl shoes, bag from a Morocco souk.

1. Amy Is an Exceptional Designer

Everyone knows that Amy is a savvy businesswoman, but in this book it is also obvious that she is a very good designer. She does not dwell on it much, but the first batch of her printed skirts sold out immediately, and her first collections sold through very quickly. It is presented as a matter of fact, but I think it is quite a big deal. Launching a brand from zero and getting it to sell immediately is noteworthy - it is nowhere near as easy as she makes it sound. Perhaps it is something she is naturally good at and does not pay much attention to? I found it quite amazing that she designed so well that even the first collections resonated with customers.

2. My Favorite Ruffles Top Is Probably Not Coming Back

In her book, Amy talks about designing by committee and miscommunication, which ends up in a top that no one on the team wants to wear. Too bad that I believe she is talking about my favorite top ever - the ruffles shirt, which I sold only because I could not pull off the color. It seems like it is not coming back - oh well! :)

Tibi top, Tibi skirt, Flattered bag, Flattered slides

3. Why Friction Matters Beyond Fashion

Friction is a topic in almost every style class, but in this book she dwells on how friction between people and in business is actually a desirable thing to have. She shares examples of how, because of communication issues with factories in Asia, they needed to think everything through very carefully and not assume that everyone was on the same page.

I still do not know if this is true - being on the same page usually helps people move faster and be more efficient. However, if you need multiple perspectives to arrive at the right outcome, deliberately seeking friction might make the process less efficient but ultimately more interesting. In the long term, it can also create greater alignment, because people are forced to explain things explicitly rather than assume everyone just gets it - especially in decisions that are hard to reverse.

4. Tibi Rejects Data in Design - But Not in Business

Amy often speaks with disdain about algorithms or data-based design, preferring instead to design in a way that reflects her principles. But in business, she is very data-driven, and many of her decisions are highly rational. For example, she describes hiring a salesperson instead of paying for a showroom, along with other choices that went against industry norms but were, dare I say, highly data-driven. She does not make this distinction explicitly, but you can see in the book that there are areas where data can genuinely help, while in creative fields they often just produce average results.

5. Never Waste a Good Crisis

The pivotal moments in the company’s history came during times of crisis. One was when print was going out of fashion and Tibi, then primarily a print brand, had to completely rethink its ethos and the kinds of pieces it designed. Another was Covid, when Amy and the team decided to move to direct-to-consumer, bypass department stores, and build the business on their own terms.

Yes, the feeling that something was off had been lingering for a while, but the real impulse to act came when the market shifted in a major way. That was what pushed Tibi to move away from prints and toward the clothes they actually wanted to make, and later, during Covid, to commit to selling directly to customers rather than relying on department stores.

I have seen this strategic philosophy play out many times in my own career. It really is true that periods of disruption often create the conditions for badly needed change - but only if you are ready for it and are clear on what you actually want.

6. Launching a Brand You Do Not Even Like

In the book, Amy recalls how they launched a secret dress brand during Covid to finance the pivot away from the print brand and toward a version of Tibi that was more in line with their aesthetic. I did some digging and found an old Facebook page for a similar brand, showing designs that could not be further from Tibi’s brand essence. Is that the one? I am not really sure, but the name matches.

Source: 4.collective Facebook page. This is purely speculation - I have no idea whether this is the actual brand the Tibi team launched, but it does seem broadly in line with what they describe.

Still, it is amazing that they managed to pull it off. In business, launching a new product is never a guarantee of success, but the Tibi team seems to know exactly what they are doing and could probably print money if they were willing to compromise on their values and design philosophy - which makes their insistence on doing business on their own terms even more impressive.

7. Living on Your Own Terms

Ultimately, what the book is really about is living on your own terms. Through many tribulations, Amy has arrived at a version of Tibi that feels true to herself and her team. She could have grown Tibi into a much bigger business - even if it already generates a massive $70 million a year - but that would have required compromising either her design vision or her process, and she chose not to do that.

It takes courage, clarity, and a real willingness to think for yourself to live that way. That, to me, is where true leadership and true inspiration emerges.

It also made me think about my own life: which principles I compromise on, and how to more consciously design the life I actually want, rather than the one the industry, society, or simply “it-was-always-done-that-way” quietly expects me to live. Ultimately, the biggest risk - or perhaps the greatest recklessness - is wasting your life, and Amy clearly wants no part in that.

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