My mom was a single mom and an entrepreneur. She founded a company called Consumer Card Marketing Inc (CCMI), which was a pioneer in the loyalty marketing space, and then served as CEO of InStream Media, a marketing services company.
That’s why, growing up, I swore I would never start a business myself.
Each day, I saw firsthand how emotionally taxing running a company can be. I watched my mom experience the financial ups and downs that come with foregoing a stable paycheck; I witnessed the late nights and early mornings that building a company requires. And, frankly, it scared me. It seemed so hard and I wanted nothing to do with it.
But after a few years in the professional world, I was bitten by the bug, too. It started with Warby Parker, when my good friend presented me with the idea to create a new brand of eyewear at revolutionary prices that would do good in the world. I couldn’t stop thinking about starting a company that improved the eyewear experience for myself and lots of other people out there. I experienced the same feeling starting Harry’s a few years later: an unceasing need to build something that has real impact in the world. Since founding Warby Parker and Harry’s, I’ve developed a newfound appreciation for my mom’s work, her tenacity, and the lessons she taught me about entrepreneurship.
1. There’s no such thing as a traditional workday
My mom worked long nights and early mornings so she could be with her kids during the days. She’d take a call from her car phone on the way to dropping me off at school; she’d work from vacation or from our dining room table after my brother and I went to bed. Her approach to what people today call “work-life balance” might not have been traditional, but she made time for both her children and her career. I’ve tried to adopt the same principles and malleability in my own life by prioritizing the things that really matter — such as bedtime with my kids and going to the gym a couple days every week — while working around and through the rest of my life.
2. Perseverance is paramount
My mom experienced major challenges in launching and running her first company. There were times when she wasn’t sure if the technology would work, or how buyers would respond to the product. She endured that stress, while navigating the surreal challenge that is raising a family and providing for us. It wasn’t always easy, and we worried together. Yet, she persevered, and believed in her goals and capabilities, and that’s always inspired me to do the same. She willed her company to work — for herself and for us.
3. Business is all about people
Growing up, I’d always hear my mom talk about the people she worked with — her team, her clients, and her counterparts at other companies. She instilled in me a deep acknowledgement that the “who” is often the “how.” People matter, strong relationships matter, kindness matters, and you must bring integrity to your interactions. When our women’s brand, Flamingo, launched last year, we looked to two of our first Harry’s hires to run the business. After years of working with them and seeing them grow in their careers, I never doubted whether they’d be able to pull it off. Being a successful leader and entrepreneur means investing deeply in your team and people overall.
4. Startups are rollercoasters
I remember the highs my mom experienced when she’d sign a new business deal, and the lows she felt when she had product issues that could impede her company’s ability to serve customers. I’ve had those same ups and downs at Harry’s — early on, when we raised enough money to buy a hundred-year-old blade factory, it felt like I could take on any challenge. At other moments, like when we realized how difficult it would be to run that factory, I questioned my abilities. I try to remind myself that the highs are never as high as they seem and the lows are never as low — what’s important is to keep moving forward.
5. It’s possible to have a family and a successful business
Throughout my mom’s career, she always remained my mom. She raised her family, provided us with a rich childhood, and was a present and loving force in our lives. She was at every sports game, and was home every evening to ask about my day at school. As a dad to three kids myself now, I’m heartened by the example my mom set and I’m grateful for her influence on my life and my career, and for ultimately teaching me the importance of balance.
Now that I’ve had a chance to build and run a company, I’ve come to appreciate what my mom felt for so long: that while running your own companies can be all-consuming, it’s also invigorating, and incredibly gratifying to build something from nothing that is both meaningful and impactful. As I write this late at night while my kids are all asleep in the room next door, I realize I wouldn’t want it any other way.
Jeff Raider is the co-founder and CEO of Harry’s (and previously Warby Parker).