Lessons in success from The Apprentice’s Linda Plant

Raised in a “very happy and humble home” in Yorkshire, Linda’s passion for business started early. At just 11 years old, she began helping on her mother’s stall in Dewsbury Market, selling women’s hosiery. By 14, they had moved to the Castle Market in Sheffield. By 16, they had grown to 14 market stalls across Yorkshire, plus a wholesale outlet. Linda left formal education and made the markets her full-time career.

“I realised how much I loved the art of buying and selling and watching other businesses,” she says.

At 23, she boarded her first flight to Hong Kong. Her fashion brand, Honeysuckle, became a full-blown reality.

It was a time when women were rarely seen in the front lines of business, but confidence was not an issue for her in a male-dominated arena; if anything, being a woman has been a driving factor.

“Men did not intimidate me. I didn’t let them intimidate me, because I had a hunger, I had a drive, I had a goal and I had tunnel vision. You’ve just got to get on with it.”

Describing herself as proudly Jewish and Zionist, she credits her work ethic and values to her Jewish upbringing. Her mother, Regina, 99, who worked as a secretary at their local synagogue and was awarded an MBE for over four decades of charity work, was a major influence.

“As a Jewish daughter, mother and grandmother, family is very important to me,” she says. “If you have strong values, that will carry you through your business life.”

She met fellow Jewish businessperson Alan Sugar back in the 1970s, in the Far East. Then in 2015, Lord Sugar called to say he needed a new interviewer for the final five on The Apprentice. “He said, ‘I’m looking for someone who’s going to expose the weaknesses, dig deep and give me good television. Can you do it?’ And he gave me an audition. He phoned me three weeks later and said, ‘don’t let me down.’” She’s been on the hit show ever since.

The first word that comes to mind when she thinks of Lord Sugar is “authentic”. “What you see on the television is what you get. I think Jewish people can be quite proud of Alan – he’s a good role model.”

Despite her decades of business experience, Linda admits she was nervous stepping into TV. That she jumped at the opportunity is down to her enduring mantra that you should always say yes. “If you don’t buy a ticket, you’re not going to win the lottery. So when he phoned me, I thought, ‘I’ve never done anything like this, but if you don’t have a go, you’re not going to know.’ It was frightening, but you’ve got to get over anxieties if you want to move forward. If new opportunities come along, seize them. Walk through every door.”

That mindset has powered her through her journey. In an era increasingly dominated by artificial intelligence and digital isolation, Linda is now launching the Linda Plant International Academy (LPIA), a face-to-face workshop programme designed to mentor aspiring entrepreneurs, especially women, with human insight.

“I believe in tech,” she says, “but right now, there’s nothing better than being in a room, interacting, brainstorming, guiding. There’s no substitute for energy and connection.”

It’s important to love what you do for work, she says. “If you want to go into business, what are you really passionate about? Because that’s how you succeed.”

And it’s never too late to pursue your goals, she says, pointing out that she joined The Apprentice at the age of 60. “Age is no barrier to success. If you’re older, you’ve got experience. Use those transferable skills, use the experiences you’ve had in life. You’re never too old.”

So what makes a successful entrepreneur? “You have to have curiosity, hunger, and motivation, not just for money, but for success. That drive, that belief that you can, is everything.”

Gaby Hersham

When Gaby Hersham was a tiny tot in her Jewish primary school reception class, her teacher told her parents that she suffered from laziness. Later, at secondary school, she and her friends were written off as the “naughty ones who were probably never going to amount to much”.

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“These things stay in the back of your mind and propel you to disprove that theory,” says Hersham, who has certainly done so as the CEO of thriving co-working business Huckletree.

The foundations for Hersham’s outstanding entrepreneurial career were laid at university in London, where she studied business and became fascinated with how the economy works. A spell at acting school in New York steered her drive to be an entrepreneur.

“Acting is an industry where you’re not in control of your own destiny, so it made me realise that I wanted to do something that I could build and be in control of myself,” she says.

Discovering the early WeWork spaces in New York gave her the dream of establishing something similar in London, to create inspiring offices to bring like-minded entrepreneurs together to build their businesses.

“I became very passionate about it,” she says. “It was all about creating spaces that could serendipitously lead to conversations. I’m a big believer that you don’t want to sit at your desk all day.”

She added classrooms and auditorium spaces where workers could be inspired by panel discussions and presentations, thereby leading the way for curated co-working spaces in the UK at a time when the startup scene was exploding with new entrepreneurs.

“We were not thinking about the spaces in terms of how can we maximise the revenue potential of each square foot. We were thinking: how can we design spaces that make people happy to come to work? That was my driving motivation.”

Although Hersham did not start out as an “obvious” candidate for entrepreneurship, her ambition and self-belief have grown along with her business which is now in ten locations.

“Over the years, I have become more comfortable accepting the fact that I am ambitious and being proud of the fact that I am very ambitious,” she says. “My business growing has given me agency to believe that I can be successful and have the right to be ambitious.”

She doesn’t know if at the beginning she believed she could build Huckletree to the size that it is now. “It has been a journey of learning to believe that actually I can. I’m a completely different person today to when I started it. I’ve got so much more self-assuredness.”

As for what’s required for a career in business, she says she is grateful for the naivety and ability to ignore anything that could possibly go wrong that she had at the beginning of her venture. Now, with a firmly established business, she says the most useful skills are being structured and organised, and resilience. Above all, it’s showing up every single day, good or bad.

“That’s something you see in the best entrepreneurs – it’s a non-negotiable. It becomes more about that ability to be resilient, to still show up every day, to have thick skin, and to believe in yourself enough to not need daily reinforcement that you’re doing the right thing.”

Her greatest Jewish inspiration remains her parents, for their persistent work ethic. When at university, she would return late from Mayfair night clubs and see the light on in the office of her father Gary Hersham, founder and co-director of Beauchamp Estates, and him at his desk. “That’s given me a sense of duty to also work hard and make something for myself and not rely on him or others.”

She gained the same drive from her mother, who fled Iran when the Jews left at the time of the revolution and came to the UK as a refugee, had two children very young, and then divorced. “Throughout it, I saw a very strong woman. I saw her always working. That gives you a sense of commitment and obligation to do the same.”

She hopes to hand on that same work ethic to her two sons, aged six and nine, the eldest of whom is already showing signs of entrepreneurship. As a successful working mother, Hersham often wonders about the fact she is unable to pick up her children and take them to school and to all their activities. “But the thought process that reassures me is remembering that I am showing boys that women can go out and work and leave a legacy, just like a man. For me, that’s really important to teach to my children, because they’re boys.”

She feels it is “underestimated” just how challenging it is for a woman running a business. “Because we’re always going to be slightly more scrutinised, and slightly more susceptible to that feeling of being scrutinised. It’s not as easy for us to be the complete bulldozer at work that it seems easy for many men to be.”

As she and her women entrepreneur peers try to keep it all together and balance their working and family lives, she feels not enough of a light is shone upon the difficulty of it all.

“We can’t actually have it all, but we really try, and I think it needs to be spoken about. Having it all doesn’t always look seamless, and balls will be dropped. Obviously we’re doing it for our own sense of purpose. But it’s not easy to be a mother who works.”

Hersham grew up in a kosher household where Shabbat was kept and the family attended St John’s Wood shul. That Orthodox element of her upbringing has woven its way into how she has built her business; the entirety of Huckletree’s 300,000 sq ft of workspace is vegetarian. “I never wanted anyone to serve any non-kosher food in my spaces,” she says. “It’s funny how your background influences what you’re building.”

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Emma Sinclair

From the age of three, Emma Sinclair was driven to school by her father, during which time he would quiz her on times tables, capital cities – and “guess the share price”.

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“In the backseat of the car I used to read share prices from the Financial Times,” says Sinclair, who now co-leads global software company EnterpriseAlumni. “I grew up talking to him about business, thinking that talking about stock markets was entirely normal – and what you do for fun.”

Those skills Sinclair picked up on journeys to school were first put to use when she started Leeds University as part of the first cohort to have a student loan, and “immediately” began trading with it. She would buy a copy of the FT on her way into the café to meet friends; the shop got it in just for her. “I was a terrible student,” she says. “What I mainly did at university was trading.”

And when she eagerly sent her trading sheets to no fewer than 14 CEOs who she had been reading about in the FT to ask for a summer job in finance, she was offered 12, of which she undertook two over the holidays. “It was a constant theme that’s maybe still in my life, which is, ‘don’t ask, don’t get’,” she says.

Sinclair, who lives in the capital with her family, became at 29 the youngest person to have floated a company on the London Stock Exchange. In 2016, she was awarded an MBE for services to entrepreneurship. She says the skills and qualities that make a good businesswoman evolve as things progress, but top of her list for success will always be persistence and resilience.

“Ninety-five per cent of the job is hanging in there,” she says, adding that as you move further along, “it becomes more about judgment and leadership being strategic and the ability to attract really great people to work with you.”

Firstly you need to identify clearly what it is you want from your business proposition, she says, “because there’s a big difference between what you need to build a globally scaled business and being able to do something that is three people and makes a very nice living.”

Sinclair is grateful to her father, who still works full-time, to whom she speaks several times a day and who remains her closest counsel on business topics.

“He’s my hero. He has not only given me everything, including the tools that I have, but he is my best friend. I wish that everybody would have somebody like him at their side.”

She also benefits from the advice of her fellow entrepreneurs and has a big network of Jewish entrepreneurs around the world. Sinclair is part of many founder networks, including a couple that have Judaism at their roots, so when she travels, there are always people from whom she can seek advice.

“I genuinely have a village, and I’ve needed different people for different advice at different times,” she says. “Following October 7, it has been so useful to have a Jewish network; it’s been absolutely essential for me to not just support Jewish peers, many of whom have had a mentally challenging time, or have had overt examples of antisemitism, but also for me reciprocally – to be able to feel a sense of allyship and community at a time when our community is being heavily attacked by some people.”

It’s important, too, for her to support and elevate young entrepreneurs to help them find their feet in the world of business. These include Andrii Cherkashyn, an 18-year-old refugee from Ukraine who was named young entrepreneur of the year by Wizo.

“One of the things I’m loving is supporting some of the most incredible, motivated and dynamic Jews from the diaspora,” she says. “That makes me very happy.”

She has also played a pivotal role in the women-in-business sphere, tackling the lack of investment in female-founded businesses. Last year she launched the crowdfunding campaign BeAnAngel, an initiative in which individuals could invest in female-founded businesses. EnterpriseAlumni became the world’s first software company at the venture stage to achieve a 50/50 shareholder gender balance. It also boasts a gender-balanced board and is WBENC-certified, which means an international, global organisation has certified that it is a female-controlled business. As Sinclair puts it: “There is female power in this organisation.”

Have things changed enough for women in the world of business? She rolls her eyes in exasperation.

“No, it’s glacial,” she says, censoring her language. In 2019 when she was about to sign the first major round of venture capital investment (“series A”) for a business, an investor said to her, “of course, you won’t be here in a couple of years. You’ll be having children.”

“At that moment, I decided I couldn’t take their money, which was substantial, and that I would launch the world’s first gender-balanced series A, and that was 2018 /2019 so quite a while ago. I spend a lot of time saying, ‘Please don’t invite women to speak on a panel at an event. It’s lovely and charming. But women need cash and deals’.”

That capable women have difficulty in reaching senior leadership roles, and the resulting discrepancy between men and women in the workplace, she calls “an absolute outrage”.

“I’m a very optimistic, positive person. It’s all unacceptable, and it’s all far too slow. And in things like technology, it’s gone backwards. It is staggering.”

She laments how, for example, some things previously put in place to support women, such as British businesses having to report on their gender-equality statistics, were removed during Covid. “It’s all not good enough and I think sometimes you’ve got to say that, as opposed to platitudes of progress.

“The percentage of investment going into women-led businesses has changed by a matter of less than one per cent and for all the effort, panels, taskforces, investing in women code, amplification about the problem and the financial and social benefits of investing in women, glacial is the most positive word I can use about the pace of progress.” t