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How Jennifer Tsay Scaled Shoott to $10M Without Additional Funding

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Jason Kirby
May 15, 2025

 

Raised $2.7M. Built a $10M biz. Never raised again.

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Most founders chase funding as if it were a badge of honor.
In this week's episode, I talk to Jennifer Tsay, who raised $2.7M and walked away.
No more funding rounds. No exit. Just profitable growth.

What you can expect:

  • 00:00 – Death Threats, Disruption & The Origin Story of Shoott.com
  • 05:45 – Why Creatives Hated Us And How We Won Them Over
  • 12:08 – From $80K to $10M: The Fundraising + Growth Playbook
  • 17:52 – How We Hit Profitability (And 20x’d It)
  • 21:26 – Cash Flow Roulette: Paying Creators Before Clients Pay Us
  • 22:57 – The $300K Mistake That Nearly Sank Us
  • 25:57 – Should You Raise, Sell, or Stay the Course?
  • 27:32 – The Brutal Truth About Valuations in Today’s Market
  • 30:38 – Founders: Before You Build a Marketplace, Watch This

Watch it Now

ABOUT JENNIFER TSAY

Jennifer Tsay is the founder and CEO of Shoott, a photography marketplace operating in over 60 U.S. cities. With a background in investment banking and a decade-long stint as a working actor, she launched Shoott to help creatives earn a sustainable living doing what they love. After raising $2.7M in early funding, Jennifer scaled the business to $10M in revenue without taking another dime, proving that profitable growth is still possible in a venture-obsessed world.

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Growing Your Startup Without Additional VC Capital with Jennifer Tsay

Jennifer [00:00]: we first came on the market, we got a lot of death threats from photographers actually. It was just really intense. What tactics are you doing to convince customers to be like, you should do an Easter shoot? We floated the idea of getting more funding, but everyone was like, no one's going to give you anything. Like, there's just no way. So what did you do to turn the business into a profit generating machine? I had so many friends that were so talented, but were so poor. No matter how talented they were, they couldn't cobble together enough work to stay the artist they wanted to be. I was like, this is sad because the arts make the world a better place. The only thing that I would have changed is I...
Jennifer [00:43]: you
Jason [00:47]: Everyone welcome back to Fundraising Demystified—today we have Jennifer Tsai with us, founder and CEO of Shoot.com (that's Shoot with two T's). Jennifer, I'm really excited because this business is close to my heart. I used to be a professional photographer, and my first tech startup was almost identical to yours five years ago. Let’s dive in—what is Shoot.com?
Jennifer [01:35]: Shoot is a professional marketplace for photographers to fill supplemental time with gigs. Clients book free mini photo shoots and only pay for the photos they want. By aggregating demand, photographers get back-to-back sessions. We handle the business—customer service, sales, marketing, gallery delivery—so they focus on shooting. We’ve been around nearly seven years, 4.9 stars on Google, and live in 60 U.S. cities.
Jason [03:21]: Marketplace pushback is famous—did photographers resist your standardized pricing?
Jennifer [03:21]: Tons of pushback. Artists felt they deserved 100% of revenue. We had to educate them on the cost/time we save them—marketing, sales, support. Early on, we even got death threats. It forced us to hone our pitch: “If you have extra capacity, let us fill it and guarantee you at least $100/hour, plus fees if clients cancel or are late.”
Jason [05:12]: I got death threats too for my photo marketplace! Artists can be brutal.
Jennifer [05:12]: Exactly. Many thought we were a scam. We countered with a minimum guarantee and strict cancellation/late fees.
Jason [06:52]: How did you fill calendars?
Jennifer [06:52]: We launched in 2018 when Facebook ads were cheap. Early targeting guessed millennials, but the real growth came from millennial & Gen Z moms capturing life’s milestones—engagements, babies, weddings. Facebook + Google ads + guerrilla marketing scaled demand.
Jason [08:40]: Then you raised $2.7M—how?
Jennifer [08:51]: One co-founder tapped his network for a friends & family round—no pitching needed. We hit hockey-stick growth: $80K→$500K→$1M+ in year one, so the capital flowed.
Jason [10:27]: Why start Shoot?
Jennifer [10:27]: I was an actor and investment banker. I saw talented artists struggling. I reconnected with my old boss, and together we built a platform to help gig-economy creatives thrive.
Jason [11:48]: Then iOS 14.5 hit, and your CAC spiked from $20 to $50–200—panic attack?
Jennifer [11:48]: Absolutely. None of us were marketing experts, so we learned from scratch: built attribution spreadsheets, cut experimental spend, and tested ruthlessly—10-day cutoffs for campaigns that didn’t work.
Jason [13:38]: Supply & demand across 60 cities—how?
Jennifer [15:52]: We monitor city-by-city capacity, hire year-round, and identify micro-moments (Mother’s Day, graduations, Easter) to smooth seasonality beyond Q4.
Jason [17:52]: Real numbers—revenue, profitability?
Jennifer [19:55]: Year 1: $80K. 2023: $8.8M (breakeven). 2024: $10.2M revenue & ~$1M profit (20× profit growth). We only know final numbers in January due to “pay for photos you want” lag.
Jason [21:26]: Cash-flow roulette—paying photographers up front?
Jennifer [21:34]: We guarantee $100/hr and pay whichever is higher (guarantee vs. commission). We lean hard on email journeys to convert sales before calendar year end.
Jason [22:57]: The $300K mistake?
Jennifer [24:29]: We skimped on accounting early—lost ~$300K due to rule changes. Lesson: hire great accountants.
Jason [25:57]: What’s next—raise, sell, or stay bootstrapped?
Jennifer [25:27]: I’m honest—I’ve never exited. Debating VC, acquisition, or running forever. I want the best outcome for everyone involved.
Jason [27:32]: Valuations & capital strategy 101—EBITDA vs. revenue multiples, liquidation prefs, recaps, and engineering an exit.
Jason [30:38]: Advice for marketplace founders?
Jennifer [38:19]: Obsess over process, logistics, and optimization. Treat your marketplace like a game—test, measure, iterate on the details every day.
Jason [39:45]: Thanks for joining, Jennifer. For more, visit shoott.com or connect on social @shootphotos / @JenjenTSAY.
Jason [40:56]: I’m Jason Kirby, MD at Thunder.vc—if you need capital strategy help, go to join.thunder.vc. See you next week!
Jason Kirby
Jason Kirby

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