1/ Spotting the red flags in dream clients
“I underestimated the importance of discernment. Early on, we had what seemed like a dream client—but red flags started to emerge. They were going through some internal strife, and their executives were contradicting each other, which bled onto our team. Winning the business took precedence over my intuition, and ultimately, the politics of our client pushed our work to the side. It taught me that winning can feel like losing if you aren’t careful who you help.” —LILLIAN MARSH, cofounder and managing principal, TinyWins
2/ Actively listening to customers
“I never imagined how important active listening would be. It means being attuned to additional context, what’s not being said, and refraining from attachments to what you want to be true. For example, I shared my cell phone number with our first 250,000 customers. It was daunting, but listening to them was how I discovered the trend of using social media for search and discovery purposes. This led us to base the entire company on social commerce.” —KONRAD WALISZEWSKI, cofounder and CEO, @hotel
3/ Stamina for the slog of leadership
“I’d worked in the trenches at other startups—doing everything from taking out the trash to managing marketing budgets. But the total accountability of owning your own business is different: making sure trademarks get filed and contractors are paid on time, answering every investor question, sending invoices, being the go-to customer service person. You have to ‘eat your vegetables’ before you can build a team that takes care of it for you.” —ANGELINE VUONG, cofounder and chief product officer, Cherub
4/ Having a sense of humor
“I severely underestimated the importance of finding lightness in all situations. Starting and scaling a business is a bumpy ride, so cultivating a sense of humor has been a powerful coping mechanism. It not only alleviated tension, but allowed me to truly enjoy the journey. Whether overcoming a logistical nightmare or navigating a difficult conversation, finding moments of lightness helped me maintain perspective and keep morale high on my team.”—MARINA MIDDLETON, CEO and co-owner, Create & Cultivate
5/ Seeing the details that matter to your customer
“In the pre-owned fashion business, I quickly realized the value of getting details like color names and styles exactly right. For example, posting a light blue Birkin as ‘Hermès Birkin bag - light blue’ might result in an $8,000 sale. But posting a “Hermès Togo Verso Birkin 35 Bleu Zanzibar Malachite” will help you find the right buyer who knows that the bag is actually worth $15,000, due to the limited release of that color and leather combination.” —BEN HEMMINGER, cofounder and CEO, Fashionphile
6/ Asking for help
“As a practicing physician, asking for help was not seen as a strength. Competent physicians are trained to handle issues within their specialty without much collaboration. But as an entrepreneur, asking for help is a good thing, so I had to retrain my brain. There are so many knowledgeable people. It’s my job to identify those people, build relationships with them, and ask for their help.” —DR. LYNDSEY HARPER, founder and CEO, Rosy
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