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Diary of a CEO · 2021-08-09 · 1h 25m

NotOnTheHighStreet.com Founder: Rapid Success Lead To My Darkest Days - Holly Tucker | E92

Notonthehighstreet founder Holly Tucker on building a pioneering marketplace, the grief of leaving her business, and chasing a good life.

NotOnTheHighStreet.com Founder: Rapid Success Lead To My Darkest Days - Holly Tucker | E92
The guest

Holly Tucker — Entrepreneur, co-founder and ex-CEO of Notonthehighstreet.com, and founder of Holly & Co; bestselling author.

The gist

Holly Tucker tells Steven Bartlett the story of building Notonthehighstreet.com, one of the world's first online marketplaces, with no tech or retail experience and very little capital. She describes raising money as a woman in 2006 when VCs dismissed it as a craft website, launching with no checkout, and nearly running out of cash before securing investment. Holly also opens up about losing her identity twice, once after a divorce and brain tumour in her early twenties and again when she stepped away from Notonthehighstreet, which she experienced as grief. She now runs Holly & Co, a 'good life' business focused on serving small business founders, and has written a bestselling book.

Big reveals

  • Holly was diagnosed with a brain tumour in her early twenties, which she could not have operated on but which was livable with.
  • Notonthehighstreet launched on the third of April with no working checkout because the multi-partner single-basket technology had never been built.
  • By Christmas they were paying staff on their personal Egg credit card cheque books and parents had remortgaged houses; the business was on its last breath.
  • After leaving Notonthehighstreet around age 40 she had two to three dark years and at stages could not get out of bed.
  • Holly reframes that period not as depression but as grief, going through the seven stages of grief and getting counselling.
  • Steven Bartlett reveals he resigned from his own business last year because he no longer had the control to steer it where he wanted.

Things worth remembering

  • Holly was nicknamed 'Holly Hurricane' and got her first job cleaning a pub at 12, with her dad waiting in the car park at 5am.
  • She got an E in business studies A-level on the same day she started work, and celebrated her 18th birthday in the office.
  • She married her childhood sweetheart, whom she met at 14, at 21 and divorced by 24.
  • Before the marketplace, Holly made and sold vegetable wreaths and created the first Chiswick Christmas fair with 200 stalls.
  • She recruited co-founder Sophie, her old boss at Publicis, who said yes 24 hours after Holly emailed her.
  • In 2006 roughly one percent of VC money went to women; VCs told them their wives did the household shopping.
  • In the early days hiring was so casual she would consider offering a chatty taxi driver a job because they needed energy, not skill.
  • After leaving, Holly threw away every pair of high heels she owned and has worn glitter trainers for five years.

Recommended in this episode

Books, products and media the guest or host genuinely endorsed here — with the buy link.

Affiliate link — we may earn a commission at no extra cost to you.

Guest’s ownBook

Do What You Love, Love What You Do

Holly Tucker

“my new book is do what you love love what you do you know i brought up this business that i loved” — Holly Tucker 00:53:04
Find it on Amazon
RecommendedMedia

Cloudbusting

Kate Bush

“one of my favorite songs is cloud busting by kate bush and when i listen to that song i feel like i'm whipping up a storm” — Holly Tucker 00:40:28
Find it on Amazon