/8 Women Entrepreneurs on What They Wish Theyd Done Differently

8 Women Entrepreneurs on What They Wish Theyd Done Differently

Everything is clearer in hindsight. Here’s what these leading founders would change if they could go back in time.

8, 2019

4 min read

This story appears in the
October 2019

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We asked eight of the entrepreneurs featured on our 100 Powerful Women list: If you could go back and change one business decision you made, what would it be? 

“The most valuable use of my time was when I invested in recruiting and retaining great people. If I could go back, I’d literally double down: double the time I spent making sure we have and keep the incredible people that help our business be successful and grow.” — Katrina Lake; Founder and CEO, Stitch Fix, the $2 billion personal styling service

“There are mini moments that come to mind: I wish I’d fought harder when people wouldn’t pay me, pushed back on contract terms, been more demanding of my expectations and needs from the get-go. As a young entrepreneur, you can tend to back down. But you have to have the confidence to get your seat at the table.” — Jaclyn Johnson; Founder and CEO, Create & Cultivate, a platform and conference series for professional women

Related: From Bankruptcy to $87 Million in Funding: How Tamara Mellon Saved Her Namesake Brand

“I would have found ways to monetize sooner. As a social entrepreneur, I was conflicted with my desire to create change while ensuring the sustainability of my venture. I would have conducted a better assessment of my expenses, identified my goal revenue needs, and had a better understanding of how to price and grow a company. It’s hard to give to others when you have a model that burns out you and your bank account.” — Natalie Madeira Cofield; Founder and CEO, Walker’s Legacy, a platform and collective for women of color in business

“I spent too long doing the safe thing — the ‘right’ degree, the job I ‘should’ take — instead of following my natural talents. I would have made the jump from professional services into business sooner. When I finally made the leap, I got a job working for a CEO who let me run loose, and I found the power to back myself. Now I don’t hold back.” — Nisha Dua; Partner, BBG Ventures, an early-­stage fund for tech startups with female founders

“When building a two-sided marketplace, you’ve got the supply side (in our case, restaurants) and the demand side (business professionals buying catering for meetings). It is a chicken-and-egg problem. Which do you have to sign up more of first? In hindsight, I would have prioritized building the supply side first, and attracted a small number of customers on the demand side. Once they’re rabidly loyal, then you have a business.” — Stefania Mallett; Cofounder and CEO, ezCater, a $1.25 billion online catering marketplace

“I would make my mental and physical health more of a priority. Growing a company means investing emotional energy, time, and sweat, and too often I put the opportunities and needs of the company ahead of my health. But overall health is the key to success, and a company will thrive with a leader who can effectively balance both.” — Charlotte Cho; Cofounder and chief curator, Soko Glam, the Korean beauty marketplace 

Related: How This Founder Built a $90 Million Skincare Business With No Beauty-Industry Experience

“I would be more confident in my own knowledge of the market. Anytime I listened to investors or partners who had not operated in Africa but were strongly advising me on switching direction, the company faltered. Our local knowledge is our strongest advantage.” — Elizabeth Rossiello; Cofounder and CEO, BitPesa, a platform that uses blockchain to make financial transactions in frontier markets faster, cheaper, and easier 


“I wish I would have hired more senior leaders to help the business grow in parallel. I identify as a builder, so I’m always going to prefer to be in the trenches with the team as we scale, when my time might be best spent focusing on what moves the needle. Having senior leaders enables me to have strategic leverage.” — Nichole Mustard; Cofounder and chief revenue officer, Credit Karma, the $4 billion personal finance brand

Check out more stories from our October/November issue’s list of 100 Powerful Women.

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