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.
• I built three schools in Laos (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).
• I was a fitness model with my poster outside of a gym in Tanjong Pagar for 2022 and 2023. Don’t believe? 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 more than pivot tables.
• 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).
• I eat exactly two brazil nuts every day. It is an excellent source of selenium.
• 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.