Shooting for Success After 40!An EvolveMe Co-Founder Interview with Shoott

We're thrilled to share a story that resonates deeply with us as EvolveMe approaches its 5th anniversary this fall!

We recently had the pleasure of interviewing Jen Tsay and Jen Yeh the dynamic duo behind Shoott, an innovative photography company. Their story is a powerful testament to the potential of midlife entrepreneurship. As female cofounders ourselves, we feel a special connection to their journey and the unique challenges and opportunities it presents.

"As for starting in midlife, seeing if we could make Shoott successful became our 'midlife crisis'. We channeled all that energy of seeking fulfillment, purpose, and excitement into growing a business from scratch." - Jen Yeh

This quote beautifully captures the spirit of embracing a new chapter in midlife – transforming years of experience into business success. In our interview, these inspiring women share how they:

• Leveraged diverse career experiences to build a unique business model

• Balanced the risks of entrepreneurship with family responsibilities

• Used their age and life experience as assets in their business journey

• Overcame moments of doubt with resilience and mutual support
  

Their journey highlights that midlife entrepreneurship isn't just possible – it can give you a significant edge. With years of experience, a clearer sense of purpose, and a wealth of skills, midlife can be the ideal time to start a business!

Read on to gain insights into their journey and find inspiration for your own midlife adventure!

EvolveMe: How did you two meet and decide to become business partners?

Jen T: We met our freshman year at Cornell University and became instant friends. We were always together, very complimentary as people, and especially loved working on projects together.

Whether it was academic projects or ones for different student organizations, we would have so much fun staying up late, ordering takeout, and working until dawn organizing things or doing crafts. Even back in college, before I knew what work was, I was like - it’s my dream for us to work together when we grow up - wouldn’t that be awesome???

And when I had my whole long journey to get to Shoott I would sometimes remember that thought so when the circumstances lined up, she was my first call. To a very large degree, my impulse at 18 had been absolutely right - it makes the work not just bearable, but also fun.

EvolveMe: What were your careers like before founding Shoott? How did that experience inform your entrepreneurial journey?

Jen T: I started doing investment banking right out of college for three years, transitioned to a less intense but still corporate finance job after; then I was done with corporate life because I was so bored.

So I quit and took classes in everything from writing and acting to cooking and dancing. I helped produce a documentary film, I went to acting conservatory for 2 years, I came out and started auditioning which meant I needed a day job. So I then got a lot of experience in the world of part-time gig work - I did teeth whitening, babysitting, working the front desk, and stocking the fridge of a hedge fund.

I had settled into a flexible full-time role as a project administrator for a group of developers for about three years when the idea and opportunity for Shoott came up, and I jumped at the chance to build the concept out.

Jen Y: I was a stay-at-home mom freelancing as a web developer and graphic designer and running a handmade children’s clothing line on Etsy. After ten years, I found myself having to start back at square one after a stressful divorce that required me to go back into the corporate world while maintaining my freelance jobs in order to provide my children the life I wanted them to have.

After four years of that, Jen T approached me with this opportunity, and there was no way I was going to turn it down! My kids were older, and I loved the idea of tackling a challenge alongside an amazing friend that was sure to be intellectually stimulating and rewarding.

EvolveMe: What unique challenges or advantages did you face starting a company in midlife compared to younger entrepreneurs?

Jen Y: I think the biggest advantage is that of experience and skill. We may not have had startup experience, but we both had very solid technical and foundational skills that helped us pick up new things much faster.

As for starting in midlife, seeing if we could make Shoott successful became our “midlife crisis”. We channeled all that energy of seeking fulfillment, purpose, and excitement into growing a business from scratch.

EvolveMe: How did you balance the risks of entrepreneurship with family responsibilities or financial obligations?

Jen Y: As a single mom and being the sole provider of my household, taking on a large financial risk was a very calculated decision. I have always hustled and been disciplined with my finances, so I knew I had a safety net to tie me through finding another job if this didn’t work out. I also left my corporate job on very good terms and was invited to go back if circumstances ever changed for me. So, all in all, I felt “safe” to try something new, knowing that I had a solid backup plan.

As for family responsibilities, my kids were in upper elementary and middle school at the time and were fairly self-sufficient (we have a Montessori upbringing to thank for that!) On top of that, we work remotely which gave me the flexibility I needed to only work when they were in school or when I was waiting for them to finish up a music lesson.

With solid time management and planning, I definitely felt like I didn’t have to sacrifice spending the necessary time with my kids to make the job work.

EvolveMe: What skills or experiences from your previous careers proved most valuable in launching Shoott?

Jen T: Literally everything. Before I worked at Shoott, I was always somewhat embarrassed by how random my resume looked, but once I started Shoott, it was like everything came together in this beautiful, intuitive way.

My strong background in financial analysis, excel, and making so many presentations was foundational in my ability to manage financials and to create processes, trackers, and projections for Shoott. My vast performing arts background made it easy for me to transition into running our brand - it was intuitive for me to develop a brand voice and look, and I absolutely knew how to both give and receive notes from my team.

My time as a project administrator helped bridge my ability to work with a tech team. My time working so many gig jobs helped me architect solutions for gig photographers and take their pains into consideration. Literally, everything has been valuable and nothing was a waste of time or energy from my past.

Jen Y: I second what Jen T said! Years of time management and figuring out how to do things efficiently and be resourceful and tenacious were necessary to push past challenges. Most, if not all, of my technical and analytical skills came from not wanting to spend time doing unnecessary data entry and repetitive analysis and figuring out how to maximize tools and platforms to get the most use and “bang for our buck” out of them.

My time as a bid manager and having to read through a plethora of legal and SOW documents and put together appealing proposals has also contributed to reviewing vendor contracts and pulling together presentations and informational docs for Shoott.

My website development and design experience played a key role in enabling me to step in as our tech team’s project manager and UI designer. Bridging communication between tech and ops requires technical knowledge, so having that background was super helpful.

EvolveMe: How do you divide responsibilities and make decisions as co-founders? Has your age and experience influenced your working relationship?

Jen T: We have such an intuitive understanding of our strengths and weaknesses, and we really complement each other when we’re working. Overall, we have the same values and priorities, and for every task or skill, one of us is usually superior at something, and/or one of us enjoys doing something the other really hates, so it works out.

The great thing about age and experience is that, as adults in our 40s, we have amassed so many more skills and experiences than when we worked together when we were 18, so it just makes working together even more super-powered.

EvolveMe: Were there any moments of doubt? How did you push through them?

Jen T: We’ve had SO many moments of doubt! We can’t even count the times! There were stretches of time when we were absolutely petrified of whether we could make it as a business, especially in years 3-5 of our existence.

We were really lucky in the beginning - Shoott took off really quickly and also grew exponentially in the pandemic as one of the few socially distanced outdoor activities you could even do.

But like any business will tell you, the only constant is change, and we hit some major challenges from changes in the digital marketing landscape making our customer acquisition costs jump by 4-10x, investors telling us they didn’t believe in our business, photographers who didn’t understand our business nonstop harassing us as being “predatory” just based on our offer and other challenges from needing to improve our foundation as a business after growing so rapidly.

It was hard to work through that doubt, but we always refocus on problems we can address and once our mindset gets productive, we’re pretty good at staying in the domain of only focusing on things in our control and moving things forward that way.

I think it also really helps that we have each other to face things together. Entrepreneurship can be really lonely and challenges are always made better when somebody is walking the journey alongside you, even if you both don’t know what you’re doing; at least you’re not scared and alone.

success after 40