Leo Gestetner: My Life & Entrepreneurship Journey

Leo Gestetner headshot

“I’ve been an entrepreneur for as long as I can remember, starting my first business at the age of 13”

About Me

I’ve been an entrepreneur for as long as I can remember, starting my first business at the age of 13. What began as a simple desire to upgrade my family’s computer soon turned into selling new computers and writing software.

Business became my escape from school, which I did not enjoy—I was a terrible student! I quickly realised that entrepreneurship allowed me to channel my energy and ideas in ways that traditional education never did.

I continued my entrepreneurship journey by both creating, and buying businesses. I have acquired and sold 6 businesses and launched over 14 – to varying degrees of success!

Married at 25, became a father at 29, and made a significant move from London (UK) to Los Angeles (USA) at 36. Each of these milestones shaped my personal life and my approach to business. The balance between work and family became increasingly important, especially as my family grew and my priorities shifted.

It wasn’t until about 20 years ago that I began to understand the importance of health in my life. In the last 8 years, I’ve embraced a more serious commitment to physical, mental, and spiritual well-being. This shift towards the balance of health (mind and body), family, work, and fun – has profoundly influenced how I now approach life.

For me, success is not just measured by professional accomplishments but by a thriving sense of overall wellness and fulfillment.

My Journey

Scans of Leo’s school reports and A Level certificate, including a teacher’s note calling him resistant to learning and a Business Studies result of grade N with no passes

Terrible at education

I always struggled at school. Both socially and academically. I failed most exams - The traditional education system was a terrible fit.

1984

1986

Letterhead for Leopard Technology, Leo’s first company, advertising Acorn, Commodore Amiga and PC hardware, software and consultancy

My First Company

Start at 13 - First selling second hand computers and then becoming a major dealer in North London, and writing bespoke software.

Leo Gestetner’s university yearbook photograph

University in the US

Attended University in New England.
A great experience to learn differently and be in another country. I wasn't healthy, fit or a very good student.
Education was always a challenge for me!

1991-5

1996

Screenshot of the Unicorn Computer Solutions website, a London based IT services provider

2nd Business - 1st Website

Launched my second business (1st website!) after returning to the UK,
providing IT services to SMEs.

Leo and his wife on their wedding day, seated in an open vintage car

Getting Married

We were so young!
Married at 25 in a very British wedding!

1998

1999

Logo for ShopSmart.com with the tagline “The smarter way to shop online”

Internet 1.0

Started working with my brother to build a market leading shopping portal across
UK, Germany, Sweden and France.

Two audiogram charts, one per ear, showing hearing loss deepening from about 25 dB at low frequencies to 90 dB at high frequencies

Hard of Hearing

My hearing deteriorated rapidly with
sudden sensorineural hearing loss.
The drop continued over the next few years.

2001

2002

Logo for the charity ORT UK with the strapline “Impact Through Education”

First Major Charity Involvement

Joined the board of ORT UK. ORT was founded in 1880 and is a global charity focused on providing education and skills training.

Chart of the consumer brand portfolio, grouped into sports brands, sports retail, premium lifestyle and accessories

Active Private Equity​

I moved from creating businesses from scratch to buying and building - Building a portfolio of consumer brands with my brother.

2003

2010

Screenshot of the Heath Capital website homepage over a photograph of a beach lifeguard tower

Starting US Journey

New decade new continent!
Left everything behind to start a new life with my wife and kids in the US.

Architectural rendering of a modern hillside spec home built in Los Angeles

Property Development

After moving to the US, I built some large spec homes in Los Angeles.

2011

2012

Screenshot of the Zenvoy website homepage, headlined “Building workforce engagement and community tools”

Going Fully Remote & Global

Building enterprise AI tools and moving to my first fully remote, global workforce.

A student pitching to a panel of four judges at an NFTE semi finals event

Giving Back

Falling in love with teaching entrepreneurial skills to kids in underserved communities, as Chairman of NFTE West Region.
Learn More

2014

2016

Leo holding a back extension on a hyperextension bench at home, arms outstretched

Physical & Spiritual

Starting a journey of learning and growing with physical, mental, emotional and spiritual personal development.

Thankz Global Recruitment website screenshot showing remote staffing platform for U.S. companies

Building Global Remote Teams

Leveraging 20+ years experience of hiring and managing skilled remote teams around the world to help US companies.

2019

2023

Leo in sunglasses on a beach boardwalk with the ocean behind him

Evolving My Health Journey

My health was stagnating and stress was mounting so I needed a change.
I completely changed my diet and it sparked the idea for Livio.

Livio healthy living app screenshot displaying fasting, nutrition, and fitness tracking features

Launching Healthy Living App

Decided to share my health journey and help others. My Co-Founders also have their health journeys. Exciting to partner with my daughter!

2024

2024

Screenshot of the leogestetner.com homepage headlined “Thriving success is rooted in building a balanced foundation of family, health, work, and fun”

Launching Personal Brand

Sharing some of my philosophies
and ideas for a balanced life,
along with ideas from others I resonate with.

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