Deborah Kay

Cambridge, Wharton alum. Ex Bain, private equity and family office investments, now into all things digital. I love anything tech, geeky and health. Day dreamer, Stoic, Essentialist, bona fide geek on fleek.

Interests: Automation, app scripts, good design, search, data analytics, no code, NLP/NLG, chatbots, augmented reality filters, ashtanga, lifting heavy weight, cooking, baking. Obsessed about optimising my health and sleep. Currently pondering the meaning of life.

• I can type at 117wpm with 99% accuracy.
• I danced as a magic butterfly in a TV show called The Magic Durian.
• I performed in the 1990 National Day Parade as a flag twirler (youtube, 45:45 to 53:24)
• I was a tap dancer in a Cambridge version of the Broadway show 42nd Street.
• I founded the Newnham College Dance Club and taught hip hop dance classes at Cambridge in exchange for cash. We used the money to buy a stereo, CDs and hip hop clothing.
• I graduated second in my class at Cambridge with First Class Honours without attending a single lecture in my third year. Here’s how I did it.
• I directed a music video called Spice Bainees. It’s somewhere on youtube.
• I co-produced a short film in London called Night Lives. It’s even on IMDB so it must be legit.
• I have more than 20 Twitter accounts. Most of them are bots and at least 3 have been permanently banned by Twitter.
• I had one viral tweet which garnered >1.2M impressions, >28K engagements, >8,000 likes, >3,900 retweets. Data scientists loved it.
• I built an Instagram AR filter with 70M impressions, just for fun.
• I was an Airbnb superhost for 2 years.
• I also got a cease and desist from Airbnb’s lawyers after building an Airbnb chatbot and Twitter bot.
• I bought a 9 year old, manual Honda Civic in London and never had an accident in three years.
• I bought an automatic CLK convertible and crashed it three months later.
• The first website I built raised $75,000 for Pencils of Promise which went to building three schools in Laos.
• The three schools in Laos are in Som Sanouk, Mak Phouk, Huoay Yen. One school was dedicated to my favourite Econs teacher from RJC, Mr Jamie Reeves. Here is the plaque.
• I had lunch with Warren Buffett in Omaha. We went to his favourite steak restaurant, Gorat’s Steak House. He gave us a ride in his car. The licence plate read “THRIFTY”. Here’s a photo.
• I dated a Grammy award winning musician.
• I stood on stage in Glastonbury in front of 70,000 people.
• I met Adele at the Brit Awards, Lily Allen at O2 Festival and Duran Duran in Paris.
• I had dinner with Yoko Ono and went clubbing with Leonardo Di Caprio in New York.
• I went to a Jordanian billionaire’s house party in London (I was randomly invited on Facebook). There were ~500 women and about 20 men and 50 Cents rolled in at 1am.
• I worked with elite athletes for two years. Some of them were Olympians.
• I was a top writer in Artificial Intelligence on Medium in 2018.
• Steve Worswick, five time winner of the Loebner Prize Turing Test, wrote a chatbot tutorial based on a tutorial that I wrote. He even credits me in his blog post.
• I minted and sold a rare digital sneaker NFT for 99 SOL.
• I lost 26 kg in 15 months.
• I am a certified yoga teacher (RYT200) but have never taught a yoga class in my life.
• I can squat >1X my own bodyweight and deadlift > 1.5X bodyweight (60kg and 90kg respectively) and can do 3 pull-ups (sad).
• I was a fitness model with my poster outside of a gym in Tanjong Pagar for 2022 and 2023. Here are photos.
• I have an app on my phone called WeCroak that reminds me five times a day that I will die.
• I like query formulas a lot.
• I wake up at 5:30am every day.
• I don’t work past 3pm and happy hour starts at 4pm.
• I have gone dry (no alcohol) every year in February for the last four years (2019/2020/2021/2022), except in 2023, when I went dry for 30 days during Ramadan.
• I have never had bubble tea in my life.

• The Tim Ferriss Show
• The Drive by Dr Petter Attia, MD
• Huberman Lab by Dr Andrew Huberman
• Making Sense by Sam Harris
• People I (Mostly) Admire by Steve Levitt (Freakonomics)

Atomic Habits – James Clear
The Daily Stoic – Ryan Holiday
Essentialism – Greg McKweon
The Molecule of More – Daniel Z. Lieberman MD, Michael E. Long, et al.
Man’s Search for Meaning – Viktor E. Frankl
Show Your Work!: 10 Ways to Share Your Creativity and Get Discovered – Austin Kleon

Digital Discovery – where I write about social media and marketing
Medium – where most of my chatbot articles and tutorials reside, including those featured in Chatbot’s Life and Chatbot’s Magazine
Singapore Sailing Federation – redesigned in 2018
NTUC Health – grew traffic from 40K to >500K visitors over 4 years
Level – currently working on website, digital marketing, social media
ColorMeHappy Cosmetics – winner of SWA Website Award 2017 (depreciated)

Build A School With Me – one of the first websites I built using Weebly for my fundraising for Pencils of Promise
Debbie Discovers Github – the first website built writing code from scratch
Debbie Discovers Strikingly – another early personal website
Stuff I’ve Designed – a portfolio built on on Tumblr
My Swipe File – a swipe file built on Tumblr

If you know, you know.