Cassandra Droogan | Founder, PYSIS Overboots

"I always say: Dream big—and take baby steps! Don’t focus on the leap, just focus on the first step."

How do you start your day?

Without fail, I check my phone first thing. I’m naturally not much of a routine person and my days consist of everything from design and working on factory floors, to developing and executing ad campaigns and media outreach, to customer service and accounting. I’m always ready and willing to shift. From that perspective, taking on something completely new and unknown suits me.


Who inspires you?

I draw inspiration from so many different people and places: Brian Smith, the original founder of UGG Australia, for persistence and vision; Sara Blakely, the founder of Spanx, for salesmanship; Tamara Mellon, the founder of Jimmy Choo, for scrappiness and embodying her brand; and Phil Knight, the founder of Nike, for EVERYTHING.

I always remember, though, that no other founder or brand’s story will be PYSIS’s story. I’ve found that it can be dangerous to become too focused on someone else’s path.


What do you need to get you through each day?

A positive attitude. Even when you take a hit, with a positive outlook, you can always find opportunity in every failure. What’s critical is to keep moving forward.


What are you reading?

I actually happen to be on an entrepreneurial kick. I just read The Birth of a Brand by Brian Smith, the original founder of UGG Australia. I’ve also just started Richard Branson’s Losing My Virginity.


Briefly describe your business and inspiration for it. 

PYSIS (pronounced like the water sign, Pisces) is a fashion-forward line of overboots, designed to be worn OVER women’s dress shoes to protect them in rain, slush and snow.

The inspiration is simple: I hate to ruin my shoes. I always remembered my Dad’s goofy, rubber galoshes from the 80s that he wore over his dress shoes in bad weather, and wanted to create something that would accommodate a woman’s heels and match her sense of style.


While our Posh Galoshes are lighter and easier to carry than heavy, bulky rain or snow boots, they’re constructed just like a regular boot – lined and insulated, with a reinforced rubber sole and they actually make walking in skinny heels more sturdy and comfortable. Each pair rolls up and comes with a convenient carry bag for storage, and the elastic closure has been a big hit with our customers.


How has your passion fueled your business?

It’s EVERYTHING. If you’re thinking about starting a business from scratch, I would honestly reconsider if you could possibly be as happy doing something else.

The early days can be anything but glamorous. I envisioned myself sitting on Oprah’s couch describing the full line of PYSIS available at stores nationwide and my ascent to the cover of Forbes.


Of course, I still have those dreams. But, first comes grinding it out – working on factory production lines, learning the nitty gritty details of warehousing and fulfillment, developing and refining advertising and media strategy—and staying up until 5am to find the correct website code to properly display five tiny thumbnails on your website! That’s a small sampling of the things I never imagined I’d be doing. But, if you have passion, you love it because you realize that those are the baby steps that ultimately bring success.


What made you decide to become an entrepreneur?

I developed the itch while at my first job in banking where I worked with a lot of smaller, privately owned businesses. And I can still remember the day I first came across Sara Blakely’s story of creating Spanx – the fact that she went to panty hose factories and commissioned them to make “footless panty hose” (Spanx) was a huge eye opener for me.


What was the tipping point for realizing you had a good business?

It was a long road of product development for PYSIS and then I essentially did a soft launch with an email to friends and family while I was learning and working out the kinks of e-commerce and fulfillment. It was only after I worked out some operational and product issues and launched more broadly that sales really started rolling in that my confidence was validated.


That all sounds pretty obvious. But shortly after the initial soft launch, PYSIS was featured as “The Next Great Thing” by FOX 5 news in DC, which was really exciting. And it was also very validating to start selling on Amazon and Shoebuy.com. It wasn’t until year two, however, when sales really took off at all the distribution points and positive customer testimonials started to roll in. That’s where everything became much clearer.


What has been the key to your success?

I’d like to say it’s a good product, but that’s simply the price of entry. Learning how to successfully reach prospective customers has been the key for us. This is something that I totally underestimated before I launched. It took a lot of trial and error and connecting with customers and prospective customers to learn what the right imagery, messaging and outreach strategy would be.


For us, Facebook advertising has really been the key. No one is searching for overboots on the internet (yet!) but Facebook allows you to push your message in front of your target consumer—hopefully when she’s in a receptive mode. It actually took me a while to come around to this, but digital advertising can be very efficient, effective and measurable. Of course, editorial media mentions are fantastic, but for a start-up brand, it’s often more difficult and can be more costly than you realize to develop a strong and consistent PR strategy that leads to sales.


What lessons have you learned along the way that you wish you would have known at the beginning of your start-up career?

I wish I had understood that advertising is so much more than $100,000 spreads in glossy magazines and million dollar Super Bowl commercials. But, more broadly:

I’ve learned that everything is a process.


Of course, you hope to find quick success, but you can’t expect it or rely on it – for your business in general, or for any individual aspect of running your business. You have to go through the process of launching an effort, monitoring it, refining it and possibly revising or pivoting. It’s critical to never make decisions in haste. And be very observant, open minded and thoughtful every step of the way.


What challenges did you face in the early days of being the Founder of your own business?

Product development was a huge barrier to entry for me. While I was armed with an inquisitive mind, a can-do attitude and probably just the right amount of naiveté, my finance degree and 10-year career in banking didn’t get me very far on the development and manufacturing fronts.


What is the biggest mistake you have made in your business to date and how have you moved past it?

I think I committed to buying too much inventory upfront. Ideally, I would have liked to move on to revising the original “Posh Galosh” style and developing new styles sooner. But, when starting out, you often have few options and no leverage. It has worked out because we’ll now be in a much more informed position when it is time to develop new styles. There really is opportunity in every pitfall and mistake if you work to find it.


What would you have done differently?

All progress and every success comes out of what came before, whether it was a strategy that was an instant smash hit or a total flop. You learn from every flop and they really are a necessary part of growth. So, the only thing that I would actually change is to hesitate less and move through all obstacles much more quickly. I’ve heard talk of analysis paralysis and it’s definitely real – the really valuable analysis actually comes after you launch a strategy or effort.


What is the biggest challenge you have had in your business to date and how did you pull through it?

After working with various product developers, agents and many false starts with countless factories, when I finally did find a factory that would work and spent three weeks essentially camped out in their sample room, the final cost quote came back at more than double the initial quote they had provided. At the time this was really crushing.


But, there were a whole host of reasons that it wasn’t practical to walk away from the arrangement and look for a new factory. So, I went for it. And, as a result, when I initially launched e-commerce, the price point was much higher than it is now. But, the quality of the product was good and over time I was able to make the right connections, improve my sourcing options, and bring the price down. I think we have the price point right now, but stay tuned for more product improvements and new styles to come!


When self-doubt hits, what do you do?

I focus on ONLY the successes to date! And reconnect with the larger vision and why I started the business in the first place. For a consumer-facing business, it always helps to revisit positive customer feedback and testimonials.


What aspects of being a start-up entrepreneur do you love and/or hate?

In the spirit of keeping it positive, I’ll focus on what I love.

It’s so easy to get bogged down in minutia of the day to day, but when I step back and think about how many women are walking around in something that I dreamed up and created from scratch, the feeling of accomplishment can be pretty amazing. And I really do love communicating with customers and hearing their feedback. I also had absolutely no clue how much I would love the design and development process.


What do you think the most important attribute a female entrepreneur/ business owner can possess?

I’ve actually never been one to focus on gender – neither during my 10-year career in banking, nor while launching PYSIS and negotiating with male factory owners or making connections with potential partners or investors.

I would say just be true to your authentic self, focus on doing good work and stay positive and opportunistic. And definitely avoid the blame game – when you launch a new business, everything is your responsibility. And I think that if, for example, you walk into an investor pitch feeling like you’re disadvantaged because you’re a woman, you’ll be dead in the water. Assume that you 100% deserve everything that you can dream up, and then go get it.


What do you do outside the office to help you stay creative/productive? 

I like to run, which can be a great way to step away when necessary and also to be alone with only your thoughts—especially in this age of crazy mass media. I actually don’t run with any music or headphones.


Other than running, I just try to stay connected to friends and family and not get too inwardly focused. You really never know when inspiration or creativity can strike, so I say just be there for others and stay open all the time. Sometimes I have to remind myself of that, especially when things get busy or stressful or I’m trying to cut back on personal spending. Your personal relationships really are everything.


What would you say to another woman who asked you if they should take the leap and start their own business?

I always say: Dream big—and take baby steps! Don’t focus on the leap, just focus on the first step. Through the process of getting that first prototype made, you’ll actually work out what needs to happen next. And that prototype may be a suite of consulting services or your signature spa treatment. Figure out exactly what product you plan to sell and how you’ll get it to your first paying customer.


I also think that it’s dangerous to create artificial deadlines. In my experience, if you set some sort of ultimatum for yourself, you’ll almost certainly be setting yourself up for failure. Instead, be diligent about honestly evaluating your endeavor and realistic about whether you’re continuing to make positive progress.

Finally, when you decide to take that first step: Don’t hesitate. Go for it! Take one step at a time and run FAST in the direction of your dream.

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