I was poached by a startup but had to sell my business of 14 years to join. I don’t regret my decision.

Samantha Shih.

This as-told-to essay is based on a conversation with Samantha Shih, a 43-year-old chief brand officer from Boston. It’s been edited for length and clarity.

After graduating from Brown University in 2003, I worked as a consultant at Deloitte for three years before spending a year in China. There, I started making custom clothing, which inspired me to open a custom suiting and shirting company. I founded 9Tailors in Boston in 2008.

Launching a business was challenging because I had little experience in retail and fashion and had to learn everything from scratch. I had some business strategy knowledge from working at Deloitte but didn’t have operational knowledge.

I learned and grew the company for 14 years. In 2022, I sold 9Tailors and jumped ship to work for a startup.

Launching a company in 2008 was tough

I had a lot of friends who were getting laid off, but I was optimistic. You can only go up from the bottom, so I thought it was an excellent time to start a business.

The company started online, keeping no inventory and making everything to order. This allowed us to identify our target customer — young professional males looking to dress up for work or weddings.

We’ve been profitable since year two, winning awards and garnering press until the pandemic threw everything off track. Running a high-touch custom clothing company that needed in-person contact and relationships was stressful. We pivoted toward making masks and sold out immediately.

Around this time, my brother called me one day out of the blue

My brother told me his former boss was advising LookSky — an Asian direct-to-consumer fashion brand looking to enter the US market — and they wanted to speak to a fashion industry expert. I had no set expectations for these calls — I enjoy helping people and sharing industry and fashion insights.

What started as one call turned into three or four calls. I met with the chairman, CEO, and the rest of the C-suite team. The company’s chairman asked if I was interested in joining them.

I had to think about it. 9Tailors was never busier after the pandemic; there was so much pent-up demand for suits, shirts, and dressing up, and our revenue kept growing.

Two things made the decision easy for me

LookSky allowed me six months to transition out of my business and design my dream job description from scratch. Although I suggested the position of creative director, they offered to hire me as the chief brand officer. I was pleasantly surprised they wanted me at the C-suite level.

I loved running my own business but wanted to make more impact, so the opportunity arose at the optimal time. At LookSky, I would have the opportunity to scale a personalized experience to potentially millions of users.

Also, I had my first child in 2017 and wanted to spend more time with him instead of working crazy retail hours. I had started feeling worn down.

I accepted their offer and nearly doubled my salary at 9Tailors.

Balancing both jobs for a while was tough

During the six-month transition, I worked about eight hours daily, six days a week on 9Tailors. Then, after my son went to bed, I dedicated time to LookSky, often for team meetings or marketing and branding projects. I thrive on being busy, so it was manageable.

LookSky asked me to sell my business, but I couldn’t talk about it until we signed the papers and closed because it could destabilize my clients and team if it didn’t go through.

The final sale was to my CMO. Even though several businesses expressed interest in buying, I preferred to sell to someone who knew the company, our clients, and how we operate.

My last day at 9Tailors was the same day I announced my departure and the sale of the business to the team. To help transition, my husband, who worked at the company for a good chunk of the 14 years that I did, stayed on for another six months.

I work remotely for LookSky, as most of my team is in Asia

Working remotely was initially a shock because I’m an extrovert who loves being around people, but one of the biggest advantages is having more control over my schedule.

Mornings and evenings are typically dedicated to team calls. Afternoons provide a window for productive personal time — I might work out, dive into a business book (I’m reading “Good to Great” by James C. Collins), or listen to a startup or tech podcast like Lenny’s Podcast, Hard Fork, or How I Built This. Best of all, I can attend my son’s events and activities.

Last summer, I was diagnosed with breast cancer, which was a shock

After hearing of my diagnosis, my team could not have been more supportive, telling me to take as much time as needed. I like being busy and productive, and work actually allowed me some reprieve.

I’ve found a company that nurtures my strengths and encourages and supports me in learning new skills. I’m surrounded by bright people who motivate me to do my best work. I’ve grown and developed tremendously.

I don’t miss running 9Tailors, though I’m incredibly grateful for the experience. While I might consider running another startup in the distant future, I’m genuinely happy with where I’ve landed.