Resources:
“And I remember I was like ‘If I just work hard enough, if I work like 20 hours a day like maybe that will make a difference’ and I had to unlearn that.”
On this episode of Startups in Stilettos, host Carlyn Bushman sits down with Jennifer Tsay, founder and CEO of Shoot, a photography company operating in more than 60 cities with nearly 2,800 five-star reviews. With a unique business model that offers free photography sessions and allows clients to pay only for the photos they love, Jennifer is helping photographers build sustainable careers while making professional photography more accessible.
Jennifer shares her unconventional journey from investment banking and the performing arts to entrepreneurship, explaining how curiosity, self-awareness, and a willingness to take risks helped her discover her path. She also opens up about the realities of building a business, from navigating changing digital marketing strategies and the impact of AI to making difficult decisions, prioritizing profitability over hypergrowth, and learning to lead as a CEO.
What We Talked About:
From Investment Banking To Photography [2:18]
Risk, Immigrant Parents, And Living Without Fear [8:45]
The Surprise Pregnancy And Miscarriage [16:22]
Unlearning Guilt And Knowing Your Business Fundamentals [23:59]
Building A Trusted Circle [33:37]
Connect with Jennifer:
@jenjentsay on Instagram
Jennifer Tsay on LinkedIn
Connect with Ingrid:
@itsingridsworld on Instagram
Ingrid Zapata-Read on Linkedin
Connect with Carlyn:
@carlynbushmanconsulting on Instagram
Carlyn Bushman on LinkedIn
Members of our Entreprenista League get access to live Office Hours with top founders that have been on our show! Join the Entreprenista League today! We can’t wait to welcome you, support you, and be part of your business journey!
Get Featured on Startups in Stilettos
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Grow Your Startup with Startups in Stilettos
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Guests
Jennifer Tsay
Hosts
Carlyn Bushman
Carlyn Bushman is a seasoned business consultant, entrepreneur, and advocate for female founders. She founded POP Business Academy to empower women entrepreneurs with tools for building sustainable, profitable businesses. As CEO of Carlyn Bushman Consulting, she specializes in helping product- and service-based business owners navigate financials, marketing, and growth strategies. With extensive corporate experience, Carlyn, a mom in a blended family and lifelong learner, has been featured on Good Morning America and in Times Square. She's here to help you make money and stay in business.
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