The Inadvertent Way to Oprah

Dear Jaime,

Jaime Windau with her son, “Bubby,” who is sporting one of the company’s best-selling styles.

Your graduation day at the Fashion Institute of Technology in NYC will be a memory you will never forget. As you sit there ready to embark on your future, you think of Maya Angelou’s words of wisdom, “You will be challenged mightily, and you will fall many times.” You will learn over time that highs and lows are a part of life and it’s how you handle them that will set you apart from the crowd and lead you to success.

Over the next decade, your experience in cultivating brands through marketing and visual merchandising will set you up for your ultimate dream—building a brand of your own. Your biggest foci throughout your corporate retail career are building strong partnerships and collaborating with others. You will inspire others, build a team and have so much fun.

Good things continue to come your way. After many years of wonder, you have a baby and he changes your world in so many ways. You and your partner call him Bubby. From the day you find out you are pregnant, this is his nickname. You spend the next few years continuing to climb the corporate ladder and appreciate your amazing nanny. But then something changes. Your company shifts its direction and you decide it’s time to create a new chapter.

You will spend many months in creation mode building this new baby empire. Product development, branding and LLC are your new buzzwords. You never could have  imagined how much you had to learn. You will put in the work and you will never stop learning as you build, tweak and evolve this brand. Love Bubby is the name. Your goal is to be THE go-to brand for statement designs for little ones. Your values on premium quality fabric, compliment-provoking statements and being socially responsible is critical as you create the final touches. These values will stay true throughout the tenure of your growth.

You are ready to launch, and life hits you with your biggest challenge yet. Your milestone birthday sends you for normal tests and within weeks you will be diagnosed with Stage 2 breast cancer. You are shook. You take the necessary treatments to beat the hell out of it. You realize during this time that women—especially mothers, really get it done.

Over the next few years, Love Bubby continues to grow. You make strategic decisions to focus on the wholesale channel and you attract shop owners who love your designs and motto “You are never too young to make a statement.” The brand stands out in the market as a strong player with a modern black and white color palette against a very pink and blue childrenswear scene.  You land a spot on Oprah’s Favorite Things. Your “Speaker of the House” design becomes a best seller overnight and everyone (especially parents) love its cheeky wit and double meaning.

You continue to focus on the social responsibility aspect of your business. You partner exclusively with a non-profit printer that employs young adults with autism. You become a top client for them and they love working with you. During a global pandemic, you choose to eliminate any single use packaging from your wholesale shipments.

As you embark on this journey here is some advice:

• Support other small businesses (especially female led). They will be so grateful and they will always have something to teach you.

• Understand what works for one brand will not always translate to your brand.

• Hire slow, fire fast and when you find great employees – take care of them.

• When others see great work, they will try to imitate. You WILL get knocked off. Balance when to make it a big deal and when to just let it go.

• Enjoy the journey. Success takes time.

Cheers to your future. Your resilience will battle highs and lows. Get ready to empower the next generation of statement makers.