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According to The Sunday Times Rich List in 2020, Dolan is worth £200 million.

On 1 May 2020, Dolan started proceedings to challenge the British Government's lockdown decision, suggesting the Government had acted illegally and disproportionately over the COVID-19 lockdown. A crowdfunded campaign to fund the proposed action achieved its £30,000 target within two days.

Outside of the accountancy and contractor industries, his investments include PHA Group Ltd, Oneserve, Jota Aviation, BajaBoard, Coast Autonomous and Jota Sport. His most recent investment in March 2019 was in Snag Tights.

After selling SJD Accountancy for £67m in 2014, Dolan re-entered the contractor accountancy market on 18 September 2017 with the launch of Dolan Accountancy. In 2019 Dolan Contractor Group was established to include Contractor Umbrella.

Following a landmark sponsorship deal with Russian energy company Gazprom, the team competed as G-Drive Racing for the 2016 European Le Mans Series following a transfer of naming rights. Racing in a Gibson 015S, Dolan and G-Drive's season got underway at Silverstone Circuit, United Kingdom, in April, where they recorded their opening win of the season in the LMP2 category. The victory was followed up with a runners-up finish at the following race at Imola, in May 2016. The team's good performance continued throughout the season and was capped with a victory in the final race of the season at Estoril, in Portugal. The victory secured the 2016 European Le Mans Series title for G-Drive Racing. Dolan topped the Drivers' classification alongside team mates Giedo Van Der Garde and Harry Tincknell, all securing 105 points.

In June 2014 Dolan bought Mandalay Estate on the West Indian island of Mustique. Once owned by English rock legend David Bowie who had the villa built in 1989, the estate had previously been owned by Felix Dennis who died in June 2014.

Dolan's career highlight was 1st place in the LMP2 class at Le Mans in 2014 with Harry Tincknell and Oliver Turvey, who replaced Marc Gené after he was recalled to Team Joest Audi Sport LMP1 team following an accident in practice for Loic Duval.

Dolan was the focus of a 2014 British documentary, directed by Charlotte Fantelli, that followed Jota Sport on their quest to win the 24 Hours of Le Mans in the LMP2 category in 2014. The film followed Dolan and his Jota Sport team mates and captured the highs and lows the team encountered on their way to victory. Journey to Le Mans was released in a number of cinemas across the United Kingdom in October 2014, and released on DVD in November 2014.

Dolan began investing in new start-up companies via Twitter in 2010, initially offering a £5 million investment pot for successful business pitches on the social networking site, earning himself the nickname "Twitter Dragon". Dolan's investments via Twitter have included Global Moguls, and mental health magazine Uncovered.

Dolan's autobiography How To Make Millions Without A Degree: And How to Get by Even If You Have One was published in 2010. It tells the story of how he built his empire after leaving school at 15. In the book, Dolan offers advice to business owners and those considering starting their own business instead of going to university.

Dolan's interest in motor racing began in March 2007 before creating his own racing team, Jota Sport, in 2008. In 2010 Jota Sport signed a multi-year agreement to become an Aston Martin official partner team in motorsports. Jota initially competed in an Aston Martin V8 Vantage at the 2010 24 Hours of Spa where the team won their class. Dolan and co-driver Sam Hancock participated in the VdeV series with a best finish of third at Circuit Paul Ricard. Dolan made his debut at the 24 Hours of Le Mans in 2011.

Dolan's first major business was SJD Accountancy, which was among the first accounting firms to offer a money back guarantee. It is the only accounting firm in the UK top 100 owned by an individual rather than a partnership. In 1999 Dolan also set up Contractor Umbrella Ltd. SJD Accountancy was acquired in 2014 along with accounting practice Nixon Williams by Sovereign Capital for over £100m .

Simon Dolan (born 20 May 1969) is a British businessman and entrepreneur.