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On Resilience: How Hitting Entrepreneurial Rock Bottom Gave Timbuk2's CEO New Life

This article is more than 7 years old.

Photo courtesy of Patti Cazzato and edited by Kendrick Daye

Patti Cazzato is the CEO of Timbuk2, the San Francisco originator of the iconic messenger bag and pioneer of digital customization. She’s the company’s first female CEO, making her a rarity in her industry, where only 3% of c-suite roles are occupied by women.

Since she’s assumed the title, the company has seen significant growth year to year: the number of brick and mortar stores has risen to 8 (soon to be 9), and Timbuk2’s commitment to ethical manufacturing remains tantamount – they’ve been manufacturing custom bags, backpacks, and accessories built to last a lifetime in the city’s Mission District since their inception in 1989.

The majority of Cazzato’s career reads like a retail industry fairytale: she started out at Ann Taylor and Esprit, then went to Sam & Libby; after 10 years, she parlayed her experience into leadership roles at Gap and Levi’s.

After another 15 years, she made the decision to leave behind her cushy job and start her own company, a hand-sewn organic San Francisco-made clothing line called Clary Sage Organics.

As she describes below, it was as an entrepreneur that she hit ‘rock bottom’. But the best part of hitting bottom, is that you can pick yourself back up and inspire those around you.

Allie Hoffman and Ally Bogard:What is the most surprising part of your professional journey, that even those who know you best might not know?

Patti Cazzato: I served as an executive assistant for many years, which is funny because if you knew my personality you would say, "What!? I can't see you doing that at all." I learned so much from being in service to more senior executives and absorbing a lot of their knowledge – listening to how they would make a decision, how they would interact with people, how they built relationships, and in some ways it was an osmosis training.

The other phase of my career (I don’t talk about much) is after I left Gap, I went to Levi's and coming out of Levi's, I really wanted to start my own business.

I took a year off, I wrote a business plan and I started my business. I thought for sure it was going to be a huge success. We opened the first store in July 2008. The credit markets crashed in October. Then the investors pulled out. I ended up in a very different situation where I had come from. Prior to that, I’d viewed myself as pretty lucky in my career path. I was optimistic and super confident in my abilities. I was coming off of working for great, strong businesses and was climbing the ladder quickly.

I had no reason to think that my company may or may not work, and that was really hard. I had my entire personal savings account and finances tied up in the business, and then something macro happens - I had to hold on tight for the next seven years.

For seven years it was blood, sweat, and tears - it was, ‘am I going to be able to make my mortgage payment?’ – that kind of blood, sweat, and tears. You’ll hear “no” a lot and as women entrepreneurs we can be incredibly hard on ourselves assuming that if we fail once, we are failures. It is important to remember to learn from each experience and take those lessons with you in your professional journey. We are strong and capable.

Hoffman and Bogard: What advice would you give a younger version of yourself, in those toughest of times, based on what you know now?

Cazzato: At times [when the business was failing] we were having strong stretches of momentum. When you are somebody who's more entrepreneurial and more optimistic in nature, whenever you get that glimmer of momentum, you follow your gut and keep pushing forward.

I think for me the biggest mistake was balancing being the creative leader and also being the banker. I was running the finances, trying to raise capital, on top of all the designing, store designing, running the store, doing all the things I needed to do to operate a start up. I wasn’t spending the proper amount of time out there hitting the pavement talking to bankers and trying to raise the investment capital.

To the young entrepreneurs that are out there reading this – my advice is to always stay in check with the day-to-day finances; I didn't raise capital in enough time, and that was my biggest mistake.

To hit rock bottom like that and then have to boost your spirit and confidence despite the hardships is no easy task. If I could advise my younger self, I’d challenge her to get back up quickly and find the next thing that you love. If you don’t, you can easily wallow in feelings of failure without finding the next great opportunity – for me, this led me to the opportunity to shape Timbuk2 into the global lifestyle brand that it is today.

Hoffman and Bogard: What lessons do you hope to pass onto those you mentor?

Cazzato: I always try to instill confidence in my mentees. I constantly tell them, "You can do it." A lot of mentees don't believe that they can make a difference, and I believe they can.

I want them to realize that their voice is important. I work with them to figure out how to build stronger relationships, and how to think bigger. It's really about getting them to be a stronger version of themselves.

I typically ask probing questions that challenge them; for me it's about really strong communications, and not holding back. Some leaders I know just talk at people: "This is me and this is my experience, and I went to this college, and I did this." To me, I don't think that helps anyone.

I ask them, "What makes you happy? What is it about that relationship that's tough? How do you think we can work on that to make it easier? Have you thought about X, Y, or Z with that person? Have you thought about X, Y, or Z with your career path? Really, why X? Why not Z?"

I show them that they can do more, and they really get a lot of energy from that, they fold into that.

They usually all get bigger jobs at some point and jobs they are truly passionate about.

Hoffman and Bogard: What would you say your big, audacious goal is?

Cazzato: I would like to help save the planet, so that my children and their children's children can survive. My big goal is to help sustain this earth.

After starting my own eco-conscious company and leaving that behind, I would never be able to work for a company that isn't a do-good company. I work for Timbuk2 because I believe in the sustainability side of the business – we improve the city through local manufacturing and build products made to last a lifetime.

I’m in a place where I come to work every day with a huge smile on my face. I can't wait to get out of bed, can't wait to go to work. It's not a job. For me, it’s bliss. It's the perfect place, and it was really a perfect combination of all the things that I've done in my past that led me to this job right here, building better products, communities, and cities with Timbuk2.