Tiff Willson Leading
What’s Next


Artist. Entrepreneur. Investor. DJ. 20+ companies. 3 exits. 

Hi, I am Tiff 🙂  I have built over twenty companies, sold three, and scaled two to hundreds of millions of users & revenue. 

At 8, I was selling handcrafted products at local craft shows. At 16, I was the largest Canadian eBay seller of the early 2000s — pretending to be ten different employees (yes, really — bill@ and janet@ were doing a lot of the heavy lifting). At 18, I was buying and selling domain names at auction. By 20, I’d already had my first exit.

Always following  my heart, even when it didn’t make sense at the time. I studied biology and chemistry in undergrad, then went to Parsons for interior design, and then to UC Berkeley for computer science. Three degrees, three disciplines nobody expected to see on the same resume — but every one of them has shown up in what I’ve built.

I’ve always been ahead of the curve — that instinct led me to write my first investor check in 2015, and since then I’ve invested in 20+ early-stage companies — including Anthropic, OpenAI, Crusoe, and OpenEvidence, among others.

Today, I’m the founder of four active ventures (Bold HQ, Roomhints, Hi Catalyst and Bow to the Bee)— each one at the intersection of something I love and a mission I believe in, building towards a more sustainable world. 

 

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A Journey Built On
Bold Ideas Forward

Early Start

Tiff began her entrepreneurial journey at 8, selling handcrafted products at local craft shows. By 16, she became the largest Canadian eBay seller of the early 2000s.

First Exit

At 20, she sold her first company, marking the beginning of her path as a repeat founder.

Award-Winning Innovation

Tiff co-founded and built Roomhints App using computer vision and interior design technology. The app grew to over 10 million users and earned her the Tech Innovation Award.

Building at Scale

She bootstrapped Roomhints to millions of users with minimal marketing spend and sold the application in 2018 while retaining the brand.

Expanding Portfolio​

Tiff launched multiple new ventures, blending design, tech, and sustainability. In 2020, she founded Bow to the Bee, a fully sustainable jewelry brand supporting bee conservation.

Leading Multiple Companies

Today, Tiff runs four active businesses: Roomhints, HiCatalyst, TStudio, and Bow to the Bee. She continues to build sustainable business ecosystems and combines technical, scientific, and creative skills to scale impactful ideas.

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